Volume 80, Issue 1 Spring/Summer 2003

Call for Manuscripts and Peer-reviewers Ethical Behavior President’s Message Highlights from the AIC Board of Directors Meeting List of Contributors Cobalt (I) Salt Formation in Hydroformylation Using the Senses to Turn Students Onto : A Comparison Between The United States and Japan

Book Reviews Books Available for Review Manuscript Style Guide AIC Board of Directors and Committee Chairs

ETHICAL BEHAVIOR A Story

Mr. Albert C. Holler, FAIC

As CEO of a large company, do I take stock • Your accountants and outside options, my high salary, etc., for my consultants will not “cook the books.” compensation for the year? This total will be • Why not divide the 120 million dollars 120 million dollars. As the CEO, I know that among your employees? It may not be the company is “bleeding” with a debt of 26 very much for each but you will have billion dollars! their respect for an ethical leader. They will do anything for you! I have over the years “wined” and “dined” ethics. Now knocking at the door is “greed.” Greed Which do I choose? The door has no latch on Does “greed” overshadow “ethics”? Only you the outside. Do I open it for my “greedy” self or can help your employees bring back a healthy keep it shut for my loyal employees? Is the life to your company. Your “greed” will not do word “ethics” still to be my goal and behavior it! Help them! now and in the future or does “greed” keep • A couple of asterisk remarks: knocking at the door and I in a moment of o It all comes out even at the end weakness let him in? of the day! (Winston Churchill) o The mills of the god’s grind Let’s look briefly at each for a moment: slowly but exceedingly fine! (A Chinese proverb) Ethics “Greed” leads its distrust and disgust for you. Since childhood, I (ACH) have learned about Ethical behavior leads to a well-lived fair play, sportsmanship, honesty, integrity and respectable life for you. to be trustworthy, believe in God are the ways to go through life. Treat other people, your Do you as a member of the American Institute of employees, and associates the way you would Chemists subscribe and put into practice the AIC like to be treated. Nice things happen to ethical Code of Ethics? persons. • You can sleep at nights! Reread it and give it some deep thought. Note • No federal agents or other people will especially the items 1 thru 11. Don’t let “greed” come to you with subpoenas to open into your life! your books and financial files.

AIC PRESIDENT’S MESSAGE…

EVOLVING PERCEPTIONS

David Riley

Communications is an important aspect of the that we have. Or it may be due to some Institute. One aspect of this is the desire of our experience that we have had. This is why we members to search for answers to the complex need to have technical articles in The Chemist. topic of professionalism. We attempt to do this Otherwise, the journal would simply be called in many different forms, one of which being The “The Thought.” After all, even though we may Chemist. Yes, we have some technical papers in have widely divergent interests and activities, our journal because there must be a connection we are all chemists. between the ethereal aspect of professionalism and the real scientific world of activity; The premise, then, is a conceivably pertinent however, we must also set the pattern for idea or direction. How do we judge the value of interpretation of all elements of our technical a premise? We inspect the various aspects of the life. The professional aspect of the American premise and try to ascertain if it might have Institute of Chemists is copied by many others some reason for further thought. In mathematics, (this is the leadership quality of professionalism) it is quite clear that an exact answer can then be and involves not only our Code of Ethics and the derived. This is why, in scientific terms, the quality of our professional life, but also how rigor of mathematics is desired and needed. This well we apply the Scientific Method to all our is also why it is necessary for someone skilled in endeavors. How, you say, does the Method the art to develop the simplest terms for become our way of life (look at the means by expressing the relationships involved in a which we run our lives)? Do we take what we premise. Mathematics also allows us to express see for granted (and make unreasonable errors as these relationships in measurable terms, such as a consequence)? Or, do we look to see if there levels of uncertainty or, more commonly, by are other sides to all questions? Indeed, the standard deviations. latter case is our mode for life—it is to our inane curiosity. Furthermore, we also test what we do For example; 40 years ago, I was employed by a and ask for pertinent information that applies to branch of AT&T known as Western Electric. each subject, no matter how trivial it is. Some of Western Electric hired me to study its extruders us have a penchant for measuring how well an and the processing of poly(vinyl chloride), or answer represents what we want to do with it. PVC. PVC is the primary insulation for wires and cables. No one had been able to get Since it is near and dear to our hearts, let us look consistent processing of PVC or even run a melt at the basis of the Scientific Method. Our every flow test on PVC because it was inherently day activity might be clearer if we looked at this unstable. I bought $150,000 worth of equipment technique. How do we start? A premise (or including an Instron capillary rheometer, an figment of our imagination) occurs to us. This infrared spectrometer, a gas chromatograph, a premise can be world-shaking or simply a new roll mill, and a melt indexer. I also joined the venture in a usually technical topic. It usually American Society of Testing and Materials requires some rational thought or direction. It is (ASTM) to learn as much as I could. After a few conceivably untenable after we think about it; months of study, I concluded that, with the hence, the premise is discarded as useless. In Instron Capillary rheometer and information contrast, there usually is some basis of reasoning from the infrared spectrophotometer, the most as to why we initially conjured up the premise. meaningful information I could get was from the Frequently, the reason for the thought is some melt indexer. I could, with this simple tool, technical program, need, or basic knowledge determine the degree of instability with a long land die and a low temperature (175°C), a high tetrahydrofuran (a good solvent for PVC) weight on the ram (20 kg), and a low charge in decreased directly as the temperature increase the bore (2.15 g). I found that the PVC, after (QED). Of course, the definition of a polymer being sheared in an extruder, first decreased in being crosslinked is that the polymer be totally molecular weight (increase in flow in the melt insoluble in a good solvent. Therefore, I indexer) and then significantly increased in developed the term “incipient crosslinking” to molecular weight through more shearing indicate this progressively increasing measure of (decreased flow in the melt indexer). My basic molecular growth. premise was that the shearing initially caused the of PVC to be broken apart into In conjunction with this increasing insolubility, I smaller pieces, then eventually, the free radicals observed a progressive change in the color I of the broken fragments would recombine into could associate with the increase in consecutive larger, more complex but stable molecules. formation in the PVC structure that Everything I tested gave me the same results; so is indicative of the controlled selective process after a few thousand of these tests, I concluded I of removing HCl from adjacent vinyl chloride was right and began to publish my results, segments of the polymer. After the double bond expounding the data as a purported hypothesis. formation reaches six to ten members, a This is the next step of building a theory. But progressive color formation occurs, indicating a even with this remarkable amount of data, I selective and controlled process of molecular knew I needed additional corroboration. As a change. This fit with my theory of molecular new technique, I extracted the plasticizer and shifting and potential growth. found the viscosity of the extract increased over that of the original plasticizer. If I dissolved For 30 years, I observed this same phenomenon PVC in the plasticizer, I found that a small with tens of thousands of samples and thought percentage increased the viscosity over that of my theory was secure. Only two flies appeared the original plasticizer by the amount equal to in the ointment. When the plasticizer content got that of the extracted material. I therefore to be almost 50% of the formulation, the plastic concluded the hypothesis proven. I now had a could be sheared as much as one could apply to real theory. it without change in molecular structure. And, when one of my clients used specific fire I went to ASTM and developed the technique retardants aluminum oxide trihydrate combined for running both the melt indexer and the with molybdenum disulfide, the molecular extraction as standard methods; the importance structure had no severe crosslinking; only some of this was that it employed a round robin increase in the rate of flow, indicating that the system to prove others could get the same fire retardants were capable of controlling the answers. After adequate round robins, proving free radicals that were so effective in unmodified that others could duplicate my results, I PVC in creating higher and higher molecular established two new methods: The Standard structures. Method for Determining the Melt Flow of PVC and other Unstable Polymers, designated ASTM Therefore, the theory had to be modified to D 3364, and the Standard Method for Measuring indicate that, if the level of plasticizer were high the Logarithmic Viscosity Number on Processed enough (50% or more of the composition), the PVC, designated ASTM D-3591. softness of the compound protected the molecules of PVC from the effects of shear. Furthermore, by testing the solubility of the Also, if the free radicals were protected by PVC after being exposed to various adequate stabilization such as the fire retardants temperatures from 175 to 190 to 200 to 210 to listed above, only small fragments could be 220°C, I developed a picture of increase in formed in a stable manner, probably by molecular weight through progressive reforming into stable coupled fragments. crosslinking that demonstrated, with temperature, the solubility of PVC in Meanwhile, other experimentalists verified my might not know how to handle the data. At any theory. Roger Pinette, in an independent study at rate, I decided to publish the results and ran into Belden Wire Corporation, using the same a hornet’s nest. The reviewers would not accept technique, ASTM D 3364, found that at low my extrapolation. temperatures and low shear, small fragments were formed and that increased molecular Imagine my additional shock too, when pursuing weight materials were formed as the temperature the structural investigation further, that extracts and shear rate increased in Brabender studies of rigid PVC by the method ASTM D 3591 made independently. The molecular specie that studied using NMR displayed no evidence of was still part of the PVC main frame without chlorine in the sample. Subsequent investigation resulting in a gel had an average molecular indicated the extract was actually fragments of weight of four million determined by size the high molecular weight processing aid, exclusion (SEC). polymethlyl methacrylate, that also was sheared in the process in a manner that I had assumed Subsequent to that, in a court case, a study of an was the action on PVC. In a sense, this verified over-worked PVC film was found by SEC to the technique of the theory because the PMMA have the same average molecular weight of four was selectively sheared rather than the PVC. million found by Mr. Pinette, confirming that that level of molecular weight growth was As a matter of reference, we have independently duplicable. observed this phenomenon of shear to be present in other polymers as well. Polypropylene is Based on this theoretical background, I somewhat susceptible to this (about half the attempted to extrapolate my data with known susceptibility of PVC) and to a less degree, high- molecules of sizes similar to the fragments that density polyethylene and polybutylene. might be formed by the shear process. I found that the linear relationship existed on a log-log Therefore, we conclude that even though a scale from one to nine for theory can be quite advanced it must be hydrocarbon molecules for both saturated and continuously inspected for flaws and unsaturated linear structures. Based on this, I shortcomings before being accepted. extrapolated chlorine-modified structures like PVC and surmised that the extracts from sheared Dr. David W. Riley, FAIC CPC CChE is the PVC should lie in the four to eight regions of President of the American Institute of Chemists. vinyl chloride type molecules. Some extracts, He can be reached at [email protected]. however, measured closer to 10, indicating that I

COBALT(I) SALT itself, or with the coaddition of are of FORMATION IN extreme industrial importance, while also being to a considerable degree the exclusive domain of HYDROFORMYLATION homogeneous catalysis. For example, the CATALYSIS hydroformylation of olefins is conducted on a 7 million ton/year scale using cobalt and rhodium J. W. Rathke,* R. J. Klingler, M. J. Chen, carbonyl, and carbonyl phosphine complexes R.E. Gerald II, and K. W. Kramarz (1). Other than anchored homogeneous catalysts, however, there do not appear to be any heterogeneous analogs for the hydroformylation Abstract reaction. Cobalt carbonyl catalysts and their High-pressure in-situ nuclear magnetic phosphine modified analogues are remarkable resonance (NMR) was used to among carbonylation catalysts, not only for their study reactions of with overall economic value and for their relatively cobalt complexes of the type, [Co(CO)3L]2, low cost, but also for their versatility. Thus, where L = tertiary phosphine, that are used HCo(CO)4 is active for the oxo and Reppe as catalysts in the phosphine-modified carbonylations of olefins to yield and hydroformylation of olefins. For the case , and (in the case of the Reppe where L is the relatively basic phosphine, carbonylation) to yield carboxylic acids (2). It is also active both for the homologation of P(n-C4H9)3, high pressures of carbon monoxide cause CO addition and methanol in nonaqueous solvents to produce higher alcohols and for the aqueous-phase disproportionation of the catalyst to produce carbonylation of methanol to produce acetic acid a catalytically inactive cobalt(I) salt with the + - in the BASF process (3-5). Cobalt carbonyl composition [Co(CO)3L2] [Co(CO)4] . The catalyzed carbonylations of formaldehyde and reaction is exothermic in benzene solution ethylene oxide have been studied for use in the with ∆H = -14.1 ± 0.1 Kcal/mol and ∆S = production of ethylene and propylene glycols (6- -48.6 ± 0.2 eu. Salt formation is favored by 8). While certainly not competitive with the polar solvents, and for the case where L is commercial heterogeneous methanol synthesis the water soluble phosphine, catalysts, HCo(CO)4 and its phosphine modified analogs are active in CO hydrogenation (9). Of P(CH2CH2CH2OH)3, cobalt(I) salt formation proceeds essentially to completion in water. particular relevance to this article, phosphine For the case where L is the weakly basic modified cobalt catalysts are used in the Shell Process for the large-scale production (400,000 phosphine, P(C H CF ) , high pressures of 6 4 3 3 tons/year) of long-chain alcohols via carbon monoxide do not result in salt hydroformylation and further reduction of formation; instead, displacement of the terminal/internal olefin substrates (1). Here we phosphine ligand occurs with the formation describe reactions of CO at high pressures with of mixtures of [Co(CO)4L]2, Co2(CO)7L, phosphine-modified catalysts of the Shell-type, and Co2(CO)8 i.e., [Co(CO)3L]2, where L = tertiary phosphine. Dependent upon the choice of L, solvent, and Introduction reaction temperature, CO reacts with the Although homogeneous catalysts are often catalysts to produce a cobalt (I) salt by CO associated with the production of addition and disproportionation as shown in pharmaceuticals and other fine chemicals, they Eqn. 1. are also important in a number of large-scale + - industrial processes. Most notably, catalytic [Co(CO)3L]2 + CO = [Co(CO)3L2] + [Co(CO)4] reactions involving the addition of CO, either by (1)

* Author to whom correspondence should be addressed. Or, it reacts by displacement of one or both where L = P(CH2CH2CH2OH)3 using an inert phosphines in the catalyst as shown in Eqns. 2 atmosphere glove box. The equilibrium and 3. constants used in the van't Hoff plots were measured as Kp values with Kp = -1 [Co(CO)3L]2 + CO = Co2(CO)7L + L (2) [salt]/[catalyst]·PCO and have units of atm . For the typical case of equilibrium measurements of [Co(CO)3L]2 + 2 CO = Co2(CO)8 + 2 L (3) the conversion of [Co(CO)3P(n-C4H9)3]2 to the + - salt [Co(CO3(P(n-C4H9)3)2] [Co(CO)4] in Both the disproportionation and the ligand benzene solution, the NMR probe was loaded substitution reactions shown in these equations with 125 mg of the catalyst and 6.0 ml of lower the efficiency of the desired catalytic benzene. The probe was then placed into the process. Disproportionation decreases the NMR magnet and was purged with CO and then o catalyst available for reaction with H2 to form pressurized with CO (77.7 atm at 22.4 C). the necessary hydridic species, HCo(CO)3L, Equilibrium data obtained by measurement of required in the catalytic process. Displacement the CO pressure and integration of the 31P NMR of the phosphine ligand, to the extent that the signals of the catalyst at δ = 53.1 PPM and the products of Eqns. 2 and 3 lead to the formation salt at δ = 51.9 PPM were collected at 75, 100, o of unsubstituted HCo(CO)4, decreases the 125, 150, and 175 C. Data for the equilibrium selectivity of the process to produce the more constant at 75 oC was compared as a function of desirable linear product favored by the increasing and decreasing temperature (and at steric bulk of the tertiary phosphine ligand. 100 oC, as a function of increasing and decreasing pressure) to ensure that the reaction The in-situ high-pressure NMR measurements measured was reversible. Similarly, described here provide some insight into thermodynamic data were also obtained for salt mitigating the effects of these detrimental formation in 1,4-dioxane solution. reactions, not only in the Shell Process, but also Displacement of the P(n-C4H9)3 by CO (via in potential phosphine-modified versions of the Eqns. 2 and 3) did not occur to an appreciable aforementioned assortment of catalytic extent in either solvent with this ligand as shown processes for which HCo(CO)4 is active. by monitoring the free ligand signal at δ = -32.5 PPM. Salt formation did not occur with the Experimental Section catalyst, [Co (CO)3P(C6H4CF3)3]2; instead, 31P NMR spectra were recorded at 121.4 MHz significant displacement of the phosphine with chemical shifts relative to 85% phosphoric ligand by CO as exhibited via the monitoring of acid at 0.0 PPM using a General Electric GN the 31P NMR signals for 300 spectrometer equipped with an 89-mm [Co(CO)3P(C6H4CF3)3]2, Co2(CO)7P (C6H4CF3)3, Oxford magnet. Measurements of equilibrium and P(C6H4CF3)3 at δ = 67.2 PPM, δ = 64.1 PPM data employed a variable temperature high- and δ = -5.8 PPM, respectively. In experiments pressure Be-Cu NMR probe containing an with aqueous solutions containing the ligand, internal toroid detector that was designed in- P(CH2CH2CH2OH)3 (δ = -29.5 PPM), salt house and has been described previously (9). formation was complete, and only the signal for + - The ligands P(n-C4H9)3, P(C6H5CF3)3, and [Co(CO)3(P(CH2CH2CH2OH)3)2] [Co(CO)4] at P(CH2CH2CH2OH)3 were purchased from Strem δ = 53.1 PPM could be observed after Chemical Company. The catalysts, equilibration with CO. [Co(CO)3L]2, were prepared by reaction of Co2(CO)8 with the phosphorus ligand, similar to Results and Discussion a literature procedure but adapted to the tertiary The van't Hoff plot for the conversion of phosphines used here (10). In each case the [Co(CO)3P(n-C4H9)3]2 to [Co(CO)3(P(n- + - pressure probe was charged with preformed C4H9)3)2] [Co(CO)4] by reaction with CO in catalyst, where L = P(n-C4H9)3 and P(C6H5CF3)3, benzene solution is shown in Fig. 1. or with the ingredients for the catalyst Thermodynamic results calculated from the ((Co2(CO)8 and P(CH2CH2 CH2OH)3) in the case slope and intercept of this plot indicate that the reaction is favorable and exothermic even in relatively non polar benzene solution. The large Acknowledgments negative entropy change measured is consistent We thank Professor J. Halpern of the University with the consumption of one equivalent of gas. of Chicago for useful discussions. Support for Also, as expected for a reaction that produces this work was provided by the Office of Basic charged species from uncharged reactants, the Energy Sciences, Division of Chemical thermodynamic parameters, ∆H = -21.5 ± 0.6 Sciences, U.S. Department of Energy. Kcal/mol and ∆S = -65 ± 1.4 eu., measured in the more polar solvent, 1,4-dioxane, are even References more favorable than in benzene. Consistent with 1. Billig, E. and Inchalik, E. J., Oxo Process. this interpretation, formation of the Co(I) salt In Encyclopedia of Chemical Technology, using the water soluble ligand 4th ed., Wiley, New York, 1996,Vol 17, pp P(CH2CH2CH2OH)3 in aqueous solution could 902-919. not be measured because salt formation was 2. Weissermel, K. and Arpe, H.-J., Industrial complete in this highly polar solvent even at low Organic Chemistry, 2nd ed., VCH CO pressures. In contrast, salt formation with Publishers, Inc., New York, 1993. the weakly basic ligand, P(C6H4CF3)3, was 3. Walker, W. E., U. S. Patent 4,277,634, immeasurably low, at least for determinations 1981. made in toluene solution. Large excesses of free 4. Doyle, G. J., J. Mol. Catal., 13, 237, 1981. ligand (as high as 6 moles of ligand per mole of 5. Koermer, G. S. and Slinkard, W. E., Ind. catalyst) were needed to mitigate the extensive Eng. Chem. Prod. Res. Dev., 17, 231, 1978. displacement of the phosphine from the metal 6. Gresham, W. F. and Brooks, R. E., U. S. center in the presence of CO. Patent 2,451,222, 1948. 7. Rathke, J. W. and Feder, H. F., Ann. N. Y. Conclusions Acad. Sci., 333, 45, 1980. For the phosphine-modified cobalt catalyst, 8. James, B. R., Homogeneous Hydrogenation, based on relatively basic tri-n-butylphosphine, Wiley, New York, 1973. formation of the Co(I) salt by CO addition and 9. Klingler, R. J. and Rathke, J. W., Progress disproportionation is thermodynamically in , Wiley, New York, favorable and exothermic even in nonpolar Vol 39, pp. 113-180, 1991. benzene solution. With use of this ligand, salt 10. Kramarz, K. W.; Klingler, R. J.; Fremgen, formation is more favorable in the more polar D. E. and Rathke, J. W., Catalysis Today, solvent 1,4-dioxane. In contrast, displacement of 49, 339-352, 1999. the tri-n-butylphosphine with CO to form free ligand is not significant even at relatively high Biographies CO pressures. For this relatively basic ligand, Dr. Jerome W. Rathke is a senior chemist and salt formation can most effectively be group leader in Argonne National Laboratory's minimized at high temperatures. Salt formation Chemical Technology Division, 9700 S Cass is disfavored due to the reaction's exothermicity Ave, Argonne, IL 60439, P: 630-252-4549 F: plus the application of as low a CO pressure and 630-252-9373, [email protected]. His current the least polar solvent available. On the other research activities encompass fundamental hand, for catalysts using the weakly basic studies of homogeneous catalytic processes in P(C6H4CF3) ligand, salt formation is not supercritical fluids, olefin hydroformylation significant, even at high CO pressures, in catalysis, NMR studies of gas-phase micelles, toluene solution. Large excesses of added ligand methane activation catalysis, transport in are needed to avoid facile displacement of the advanced batteries, and the development of in phosphine by CO. For the catalyst system based situ spectroscopic techniques for studies of on water soluble P(CH2CH2CH2OH)3, salt gas-phase chemistry at high temperatures and formation is complete in aqueous solution and high pressures. no other complexes were detected in this highly polar solvent even at low pressures of CO. Dr. Robert J. Klingler is a staff chemist and Technology Division at Argonne National principal investigator in the Chemical Laboratory, P: 630-252-5258 F: 630-972-4453, Technology Division at Argonne National chenm@cmt. anl.gov. Laboratory, P: 630-252-9960 F: 630-252-9373, klingler@ cmt.anl.gov. Dr. Klingler's research Dr. Rex E. Gerald II is a staff chemical interests lie in the determination of reaction physicist in the Chemical Technology Division mechanisms, in situ spectroscopic techniques, at Argonne National Laboratory, P: 630-252- and catalyst design. In current work, the 4214 F: 630-972-4458, [email protected]. mechanisms of ion transport in polymer electrolyte battery materials are being Dr. Kurt W. Kramarz is a senior chemist in the investigated by an in situ NMR imaging Plasticizer Group at Sunoco Chemicals' technique that was developed by Drs. Rathke Research and Technology Center, 550 and Klingler at Argonne. Technology Drive, Pittsburgh, PA 15219, P: 412-208-8169, F: 866-560-0372, Dr. Michael J. Chen is a staff chemist and [email protected]. principal investigator in the Chemical

Figure 1 + - Van't Hoff plot for the conversion of [Co(CO)3P(n-C4H9)3]2 to [Co(CO3(P(n-C4H9)3)2] [Co(CO)4] by reaction with CO in benzene solution.

USING THE SENSES TO TURN Sponsors for this project include Suzuka National College of Technology in Japan and the STUDENTS ONTO CHEMISTRY: Northern New York Section of the American A COMPARISON BETWEEN Chemical Society. THE UNITED STATES AND JAPAN Project Description Materials used in this project include a music tape, overhead transparencies, pictures to serve Dana M. Barry*, Hideyuki Kanematsu, as visual aids, hands-on chemical experiments Tatsumasa Kobayashi, and Hiroshi and evaluation forms. The music tape, Chemical Shimofuruya Sensation with the Barry Tones, contains songs that address many topics in high school / college Abstract chemistry curriculums (1). These songs were Chemistry researchers/educators in the United part of the science education television series States and Japan have developed a method that Sensational Science, which aired in New York uses the senses to turn students onto chemistry. State in 1996 and 1997. Most students are This approach, known as the “Chemical interested in music, so it is a great way to Sensation Project,” incorporates diverse learning capture their attention and turn them onto styles to meet the needs of all students. It chemistry. The words to the science songs are combines music, pictures, and hands-on on overhead transparencies and handouts that experiments to provide multi sensory lessons are distributed to the class. that complement existing college / high school chemistry curriculums. Dr. Barry composed the music, wrote the lyrics for the science songs, and prepared the pictures Introduction and hands-on experiments for the program. Chemistry educators / researchers in the United Professor Kanematsu translated everything into States and Japan have developed a multi sensory Japanese for the students in Japan. method for teaching college and high school chemistry. Their creative approach, known as Below are the titles of songs and activities used the “Chemical Sensation Project,” uses diverse to provide multi sensory lessons which learning styles to meet the needs of all students. complement existing high school / college It combines music, pictures, and hands-on chemistry curriculums. experiments to provide multi sensory lessons. These lessons are intended to be incorporated Song: Organic Chemistry into the lecture component of existing chemistry Activities: (Hydrocarbons) and (Functional courses. Groups) Song: Acid Verses In addition the program, which relates chemistry Activities: (pH and Indicators) and (Acids and to daily life, gives students positive and Bases) meaningful experiences in science. Song: Chemicals Activities: (Chemicals) and (Bonds) This collaborative effort to promote and enhance Song: Fission and Fusion is of great interest in Japan, Activities: (Half - Life) and (Helium and other where most students are taught by the face-to- Gases) face lecture method. The authors of this paper Song: Science Is have already been invited, by prestigious Activities: (Cooking) and (Walking) Japanese organizations, to give presentations Song: Matter and Energy and to write journal features about this program. Activities:(Mixtures) and (Surface Tension) Song: * Author to whom correspondence should be Activities: (The Human ) and (Periodic addressed. Table of Items) Evaluations has horizontal rows called periods. The The teachers/instructors complete simple elements in each period have the same number evaluation forms describing the use of the of principal energy levels. The periodic table program in their classes. Also students answer also has vertical rows called groups or families. questions accompanying each chemical activity The elements in any group have similar physical to provide educational outcome results. In and chemical properties. Elements on the left addition, both students and instructors complete side of the table are metals. Metals tend to shine a form, which makes use of a semantic with a metallic luster when polished. Also they differential method. are good conductors of heat and electricity. Elements on the right side of the table are Procedure nonmetals. Nonmetals are mainly gases and dull Participants begin by viewing the activity solids. Also they are poor conductors of heat picture and words to the selected chemistry and electricity. song, while listening to the song. Next they perform an exciting hands-on activity that Activity: Use paper and a pencil to design a complements the song. Finally they answer “Periodic Table of Items.” Obtain the following activity questions and complete the evaluation ten items or other available items (toothpaste, forms. shampoo, cracker, fruit, pencil, coin, aluminum foil, paper, water, and a paper clip). Closely Multi Sensory Lesson examine each item. Look for similarities and The following song and activity provide a multi differences. (Hint: Food items in a grocery store sensory lesson to complement material in a high are arranged according to similar properties. For school chemistry unit about the Periodic Table. example, dairy products are grouped together in PERIODIC TABLE the same aisle or the same section of an aisle.) (music style: soft rock) Refer to the “Periodic Table of the Elements” as First Verse a model to obtain design ideas for your S stands for sulfur and is B. “Periodic Table of Items.” On the back of your Cl stands for chlorine and carbon is C. table, write a brief description about its layout Na stands for sodium and helium’s He. and organization. Al’s aluminum and phosphorus is P. Extension: Obtain samples of three elements Second Verse that are in the same group of the “Periodic Table Metals are found on the table’s left side. of the Elements.” Examine them closely. Then Nonmetals are on the right where they hide. briefly explain (in a short paragraph) why the Metals include sodium, copper, and gold. three elements have been grouped together. Nonmetals are mainly gases I’m told. Chorus Pick your favorite element and write a report Periodic Table, Periodic Table. about it. Mendelev is given credit for the Periodic Table, Periodic Table. Results It contains elements with a symbol for each The “Chemical Sensation Project,” which is a label, symbol for each label. multi sensory approach to learning, is intended to complement material in existing high school / Periodic Table Of Items college chemistry curriculums. The program Question: Can you design a periodic table for a was carried out at both the college and high given set of items? school levels. Participant organizations include Clarkson University, Edwards-Knox High Information: The elements in the modern School and Canton High School in the United periodic table are arranged in order of increasing States and Suzuka National College of atomic number (number of protons). Each Technology, Takada High School, and Kanbe element has its own symbol. The periodic table High School in Japan. Evaluation results are composer gave the songs a very high rating. The provided. data show that the overall Japanese student reaction to the program is a little lower than that Overall the class instructors participating in of the students in the U.S. However 94 % of all the program gave it a high rating. 100 % of the student participants had a neutral -very the teachers and professors participating in the positive reaction to the activities and 84 % of program had a neutral - very positive reaction to them had a neutral - very positive reaction to the its theme (the combined use of songs and songs. activities). They really liked the hands-on Conclusion activities and the multi sensory approach to The “Chemical Sensation Project,” carried out learning. They said that the chemical by Professors Kanematsu, Kobayashi, and experiments were exciting, useful, and Shimofuruya (of Suzuka National College of meaningful to the students. The instructors also Technology in Japan) and Dr. Barry (of liked the music component and believed it to be Clarkson University in the U.S.), has been educational, entertaining, and relaxing. A successful at both national and international constructive comment made by several Japanese levels. This unique method, which combines instructors was that the songs might be more music and chemical activities, provides multi helpful to their students if they were sung in sensory lessons that complement existing Japanese. (These students viewed the words in chemistry courses. Students, who learn by Japanese, while listening to the songs in seeing, view pictures and the words to the English.) science songs. Also listening, writing, and hands-on activities are incorporated into the Organic Chemistry Professor Hiroshi program. Student participants using this Shimofuruya, of Suzuka National College of approach learned chemistry. After each lesson, Technology, said that his students learned a lot they were required to answer chemistry of chemistry by carrying out the exciting hands- questions. Over 96 % of the U.S. participants on activities using hydrocarbons and functional answered the questions correctly. In addition, groups. He was also impressed that the the instructors and students found the program to experiments included commodities used in daily be useful, challenging, and fun. life. References Edwards-Knox chemistry and physics teacher 1. Chemical Sensation with the Barry Tones, Amy Carr said that her class very much enjoyed Copyright 1996 by Dr. Dana M. Barry. the multi sensory lesson on acids and bases. She 2. Kanematsu, H., Shimofuruya, H., felt that it was very appealing to all students of Kobayashi, T., and Barry, D. M., “Using all learning styles, including students with Hands-On Activities to Teach Chemistry,” disabilities. Also she agreed that it would be Proceedings of the Annual Meeting for the wonderful to incorporate as many learning styles Japanese Society of Engineering Education as possible. in Tokyo, Japan, 473 (July 2002). 3. Kanematsu, H., Shimofuruya, H., One can say that the student participants as a Kobayashi, T., and Barry, D. M., “Hands- whole very much enjoyed the program. They On Activities to Turn Students on to gave the songs a high rating and the hands-on Science: A Comparison Between the U.S. activities a very high rating. See the chart at end and Japan,” Proceedings of the Faculty of paper entitled “ Chemistry Activities and Workshop for National Colleges in Ibaragi, Songs: U.S. Versus Japan.” The lower rating of Japan, 209 (August 2002). the songs by some of the Japanese students may 4. Barry, Dana M., “Chemical Sensation be due to cultural differences, such as being Project,” The Journal of Suzuka National accustomed to very different teaching styles. It College of Technology in Japan, (September is interesting to note that the Japanese students 2002). (at Takada High School) taught by the music’s 5. Barry, Dana M., “International Chemical About the Authors Sensation Project,” The Bulletin of the Tokai Dr. Dana M. Barry, a Certified Professional Kagaku Kougyoukai (The Society of Chemist, is an External Professor for Ansted Midland Chemical Industries in Japan), University in Malaysia and Editor/Technical (January 2003). Writer for Clarkson University’s Center for 6. Barry, D. M., Kanematsu, H., Shimofuruya, Advanced Materials Processing. (For more H., and Kobayashi, T., “Multi-Sensory information you may contact her at Box 5665 Approach to Teaching Science,” The CAMP at Clarkson University in Potsdam, NY Science Teacher’s Idea Bank, (accepted for 13699 or send email to her at publication). [email protected]). 7. Barry, Dana, “Innovative Hands-On Activities for Middle School Science,” The other authors are Professor Hideyuki Resources in Education (1999). Kanematsu, Professor Hiroshi Shimofuruya, and 8. Barry, Dana, “Delicious Chemicals,” Professor Tatsumasa Kobayashi. They are Resources in Education (July 1999). members of the and Engineering Department at Suzuka National Note: The program components (evaluation College of Technology in Japan. forms, songs, activities, etc.) are the property of the authors.

Chemistry Activities and Songs: US vs. Japa n Organization Total Hands-On Activities Songs Number Category: Positive Category: Positive S tudents Number of % Number of % Neutral-Very (Nearest Whole Neutral- (Nearest Positive %) Very Whole %) Reaction Positive Responses Reaction Clarkson University (US) 2 8 2 8 1 00 2 6 9 3 Edwards-Knox High School (US) 2 0 2 0 100 1 8 9 0 Canton High School (US) 21 18 86 17 81 Total for 3 US Organizations 6 9 6 6 9 6 6 1 8 8 Suzuka National College of 43 42 98 28 65 Technology, Japan Takada High School, Japan 56 51 91 55 98 Kanbe High School, Japan 3 9 3 6 9 2 3 0 7 7 Total for 3 Japanese Organizations 138 129 93 113 82

Total for Both US and Japanese 207 195 94 174 84 Organizations

BOOK REVIEWS

Advances in , Vol 27 Dogonadze-Kuznetsov-Levich (DKL) Model, Editors: Douglas C. Neckers, William S. Borgis-Hynes (BH) Model, and Lee-Hynes (LH) Jenks, and Thomas Wolff Model. The parameters controlling the dynam- Publisher: John Wiley & Sons, Inc. ics of proton-transfer processes were described ISBN# 0-471-21451-5 with comparison of Semiclassical and Quantum Price: $135.00 Models. A survey of the experimental studies in This is the most recent volume of the well- the author’s own lab was then presented. Fi- known Advances in Photochemistry series. As nally, the comparison of benzophenone/N,N- stated by the editors in the preface, the purpose Dimethylaniline with other proton transfer mo- of the series is to ‘explore the frontiers of photo- lecular systems was briefly reviewed with focus chemistry through the medium of chapters writ- on the latest studies. ten by pioneers who are experts’ and ‘have strong personal points of view’. Each chapter Chapter 3 discusses the functional molecular provides not just a simple literature survey, but glasses as building blocks for future optoelec- more importantly, some critical discussions and tronics. It was written by Thomas Fuhrmann evaluations of existing data. and Josef Salbeck at Kassel University, Ger- many. After a brief introduction of the low- The first chapter is about the supramolecularly molecular glass and molecular materials for op- organized luminescent dye molecules in the toelectronics, the authors gave a through discus- channels of zeolite L. It was written by Gion sion on structural concepts for molecular glasses Calzaferri and colleagues in the Department of (including chelate complexes, twin molecules, Chemistry and , University of starbust molecules, spiro molecules, tetrahedral Bern, Switzerland. In this chapter, the authors molecules, and others). The optical (absorption described the design and important properties of and emission) properties of molecular glasses supramolecularly organized dye molecules in the and doped systems were surveyed according to channels of hexagonal zeolite L nanocrystals. material types and their color ranges. The au- The chapter showed that zeolite L is a very suit- thors then presented a wide range of applications able host for the arrangement of a wide variety for thin-film devices from these materials with of chromophores. The chromophores can be focus on the applications based on the interac- aligned in a certain direction inside the channels tion with light and electricity (including organic and the formation of non-fluorescent dimers can electroluminescent devices, solar cells, photo- be prohibited. This host-guest system can be chromic and photorefractive materials). used to make very efficient nanoscale two- directional photonic antenna systems. The Overall, this book provided an authoritative re- preparation of the dye-zeolite systems was not source on the current research achievements in covered in this chapter although references were some of the important areas in photochemistry. provided. The introductory material is concise and the ap- plications are up to data. All the chapters have Chapter 2, written by Kevin Peters at University references up to 2001 (some even to 2002) of Colorado, is a excellent review on the photon- which enhances the merit of the book and also transfer reactions in benzophenone/N,N- allow the readers to carry on further researches Dimethylaniline photochemistry. After a brief on these topics. This book and the series of introduction of the proton transfer process, the which it is a part are of continuing value to the author presented an in-depth view of the mecha- photochemistry community and should be a re- nism for the photochemical reduction of benzo- quired acquisition for most libraries. Both re- phenone by N,N-dimethylaniline. This discus- searchers and graduate students interested in sion is followed by an general introduction of photochemistry will benefit from this book. various theoretical models, including Classical Reviewed by Yushen Guo, Ph.D., FAIC Model, Semiclassical Model, Proton Tunneling, Applications of Inorganic Flight Secondary Ion Mass Spectrometry (TOF- Author: John R. DeLaeter SIMS), and Laser Ablation Microprobe- Publisher: John C. Wiley and Sons Inductively Coupled Plasma Mass Spectrometry ISBN # : 047-134-5393 (LAM-ICPMS) is meritorious. Discussions sur- Price: Unknown rounding the application of inorganic mass spec- Since its discovery, mass spectrometry has trometry to forensic, biomedical and biological evolved into a powerful analytical technique be- studies were limited in scope but served as a ba- ing used effectively in both stand alone and hy- sis for further investigation for potential applica- phenated configurations. Applications of this tion to contemporary challenges outside of the technology currently span from academic, indus- scope of discussions presented in this chapter. trial, and pharmaceutical research laboratories to clinical and forensic laboratories. The hallmark This textbook is strongly recommended as a feature of this technique is its analytical ability supplementary edition in academic programs to present unequivocal molecular fingerprints of teaching nuclear science and , chemical entities of organic, biochemical, and geo-environmental science, and inorganic origins. Inorganic mass spectrometry material sciences. It will certainly show utility is an area that is not common or well understood in programs embarking on studies in medical by many practicing analytical specialists and as and especially forensic areas. The interesting such, the important utility of this analytical in- examples presented underscoring inorganic MS strumentation remains unrecognized. Therefore, renders this book useful to the generalist in the the presence of “Applications of Inorganic Mass area of mass spectrometry in addition to the spe- Spectrometry” by DeLaeter is a welcomed addi- cialist who desires a basis of further develop- tion to this wealth of information. ment in this intriguing scientific area. Reviewed by Peter D. Frade, Ph.D., FAIC The content of the text presented by DeLaeter is divided into an overview of instrumentation and Applied : The Uses of Power applications of inorganic mass spectrometry. Ultrasound in Chemistry and Processing Each section is enriched with introductory mate- Author: Timothy J. Mason and John P. rial, tables, diagrams, and lucent discussion per- Lorimer tinent to a clear understanding of the topics de- Publisher: John Wiley & Sons, Inc. veloped. Complementary to text discussion are ISBN# 3-527-30205-0 appendices of standard atomic weights and iso- Price: $ 125.00 topic compositions of the elements under con- Applied Sonochemistry: The Uses of Power Ul- sideration in the body of the text. Where appro- trasound in Chemistry and Processing, by priate, each chapter begins with a historical per- Timothy J. Mason and John P. Lorimer, is a spective and is interwoven throughout the book. book for several audiences. Power ultrasound Mathematical development is minimized focus- has been used for many years in two specific in- ing on fundamental relationships and equations. dustrial areas, cleaning and plastic welding. This point will be greatly appreciated by reader- Many of the applications depend on generation ship of limited exposure to advanced mathemat- of acoustic cavitation in liquid media. This book ics as applied in this area. Plots and diagrams are focuses on the application of the technology. truly reflective of the material present in the There are brief sections on the historical, theo- body of the text. DeLaeter incorporates his own retical and equipment of sonochemistry. research in this offering. This book is divided into seven chapters. Chap- This reviewer was impressed with the diversity ter 1 entitled Introduction to Applied Ultrasonics of applications addressed by this premier ana- has sections on background, sound frequency lytical technique. DeLaeter’s incorporation of ranges, some of the current industrial uses of ul- the contemporary instrumentation and applica- trasound and ultrasound in cleaning. Chapter 2 is tions of Fourier Transform Ion Cyclotron Reso- entitled General Principles. The six subsections nance Mass Spectrometry (FTICRMS), Time-of- of this title cover an introduction, intensity and pressure amplitude, sound absorption, bubble Although the book is supposed to be cloth- formation and the factors affection cavitation bound, my copy was precariously held together threshold, motion of the bubble in the applied with a clear plastic front cover and a soft back acoustic field and a summary section. The sum- cover. Whether a result of haste or a non- mary sections covers frequency, solvent, tem- conformist author, the book is unusual in many perature, gas type and content, external applied other respects: The number of pages (xv+345) pressure, and intensity. For this chapter there are is approximate and pagination is arbitrary (some 6 Appendices and an operational computer pro- pages are unnumbered, others missing), e.g. gram. Chapter 3 is entitled Synthesis. The syn- page 43 is followed by an unnumbered page and thesis chapter subsections are The Various Sites then by page 46. All figures are in black and for Sonochemical Reactions, An Attempt to De- white, and the claimed “16 full-color plates”, I fine the Laws of Sonochemistry, Homogeneous could not find. Though written in prose, the au- Reactions, Heterogeneous Sonochemistry, thor used poetic license extensively. The “Con- Sonochemical Preparation of Ultrafine Powders tents” listing the “sections” and “essays”, gives and Nanostructured Materials. Chapter 4 is enti- as page number 00 in all cases. tled Sonochemistry in Environmental Protection and Remediation. The subsections include an in- In spite of these imperfections, the book is troduction, water purification, biological decon- highly entertaining and informative. We are told tamination, sonication of water, surface decon- that Margarita Philosophica, published in 1503, tamination, the control of air-borne contamina- is the first modern encyclopedia of any impor- tion and the treatment of sewage sludge. Chapter tance, and was printed less than fifty years after 5 is entitled Polymers. The subsections include Johannes Gutenberg printed his first books in an introduction, degradation of polymers, factors 1455. The Margarita Philosophica (Philosophi- affecting polymer degradation, degradation cal Pearls) reflects the university curriculum at mechanisms, polymer synthesis, and ultrasonic the end of the fifteenth century, and it covers: processing of polymers. Chapter 6 is entitled grammar, logic, rhetoric, mathematical topics, Sonoelectrochemistry. The subsections include astronomy, music, childbirth, astrology, and hell an introduction, electrolytic discharge, electro- (yes, hell). plating in the presence of ultrasound, sonoelec- Figures in The Art of Chemistry include: troorganic synthesis and a summary. Chapter 7 • Mundus Subterraneus is entitled Ultrasonic Equipment and Chemical • ßs (the basilisk or cockatrice) Reactor Design. The subsections include meth- • Liber de arte destillandi (book on the art of ods for the generation of power ultrasound, ul- distillation) trasonic apparatus, and large-scale applications. • Coelum Philosophorum (heaven of the phi- Each chapter has a list of references for that losophers) chapter. The book has a subject index and is 303 • A Compendious Body of Chymistry (by Le pages in length. Févre) Reviewed by Anne T. Sherren, Ph.D., FAIC • La Chymie Charitable et Facile, en Faveur de Dames The Art of Chemistry • (written by the feminine hand of Marie Author: Arthur Greenberg Meurtrac) Publisher: John Wiley & Sons, Inc Figures 11b, 11c, and 12a-d are depictions of ISBN: 0-471-07180-3 gods and goddesses in triumphal chariots herald- Price: $59.95 ing the six ancient metals besides gold: Venus The Art of Chemistry (subtitle: Myths, Medi- (copper), Jupiter (tin), Saturn (lead), Mercury, cines, and Materials) is a collection of photo- Luna (silver), and Mars (iron). graphs related to the , and On page 18 we find a sixteenth century recipe accompanying narrative (70 “essays” in eight for “Le Toothpaste”: “sections”) plus Epilogue consisting of 2 essays.

Take blood of Dragon and Cinnamon three 1999), a collection of protocols, detailing the use ounces, calcined alum two ounces; reduce all to of biotransformations in synthetic organic chem- a very fine powder, and polish your teeth twice istry. Since the early 1990s biotransformations each day. have become accepted as powerful methodolo- gies in synthetic organic chemistry, and the pur- Liber Mineralium Alberti Magni – we are in- pose of this volume is “to cover the panoply of formed – deals: catalytic methods available to the synthetic “De metallorum origine et inventione, genera- chemist, incorporating biocatalytic procedures tione…….colore…..virtute, transmutatione” where appropriate”.

In Chaucerian English (p. 22) an alchemist an- For the “newcomer”, Chapter 1 (The Integration nounces he will transform mercury (a base of Biotransformations into the Catalytic Portfo- metal) to silver (a noble metal): lio) is a brief but excellent introduction to the For here shul ye se by experience, use of purified enzymes or whole cells as bio- That this quicksilver I wol mortifye catalysts covering: hydrolysis of esters, amides, Right in your sight anon withouten lye, nitriles, and oxiranes reduction reactions oxida- And make it as good Sylver and as fine, tive transformations carbon-carbon bond form- As there is any in your purse or myne. ing reactions Part II, consisting of chapters 2-12 describes “procedures”; while the crowning The Epilogue, the author admits, consists of two Chapter 13 discusses “Employment of Catalysts brief, more personal essays. One is about a Working in Tandem”, a one-pot sequential friend from adolescent years, a quirky and in- asymmetric hydrogenation utilizing Rh(I) and genious butterfly collector and mischief-maker, Ru(II) – catalysts, and other tandem procedures. who became a world renown entomology pro- fessor at Harvard. The second is a brief essay The following is only a sampling of microorgan- whimsically visiting the author’s own chemistry isms (enzymes) used in biotransformations: genealogy, and insists that these may appear to Acinetobacter sp., Baker’s yeast (for asymmetric be exercises in self-indulgence and self- reduction), Baeyer-Villiger monooxygenases, aggrandizement, but they are not meant to be. Beauvaria sulfurescens (epoxide hydroxylase), This book is not intended as a refresher of your Brevibacterium sp., Burkholderia cepacia (li- knowledge of Greek or Roman mythology, me- pase), Caldariomyces fumago, Candida Antarc- dieval Latin, or Old English; but reading this tica (lipase), Comamonas acidovorans, Cun- book may give you cause to brag about your ninghamella echinulata, Culvularia lunata, Cyto- knowledge of these subjects, or make you feel chrome P450, D-threonine aldolase, Escherichia deficient, as the case may be. coli, Galactosyl transferase, Lactobacillus sp, Reviewed by Spyros A. Lazaris, Ph.D., FAIC Mucor sp., Pichla fasinosa, pig liver esterase, porcine pancreatic lipase, Rhizopus sp., Sac- Catalysts for Fine , Vol- charomyces sp., Lithreonine aldolase, Xantho- ume 1 Hydrolysis, Oxidation and Reduction monas oryzae, etc. Some enzymes, e.g. sy- Editors: Stan M. Roberts and Geraldine droxynitrile lyase (from Hevea brasiliensis) have Poignant been cloned and overexpressed. Publisher: John Wiley & Sons, Ltd ISBN: 0-471-62381-4 Chapters 2, 3, 4, 5, and 6 present an overview Price: $149.95 and a comparison between various existing Hydrolysis, Oxidation and Reduction constitutes strategies for asymmetric epoxidation of unfunc- Volume 1 in the Series: Catalysts for Fine tionalized , , -unsaturated ketones and Chemical Synthesis, with Volumes 2 and 3 being allylic alcohols. Chapter 7 discusses asymmetric in the planning stage. dihydroxylation and aminohydroxylation. Chap- ter 8 discusses asymmetric sulfoxidation. Chap- In this volume frequent reference is made to ter 9 deals with asymmetric reduction of ketones Preparative Biotransformations (Wiley-VCH, using organometallic catalysts. Chapter 10 is on asymmetric reduction of ketones using Baker’s new book on Chemical Technology. This book yeast. Chapter 11 covers asymmetric reduction deals with some typical traditional chemical of ketones using non-metallic catalysts process technologies with additional applica- (oxazaborolidine reduction of acetophe- tions to processes in biotechnology. It is a wel- none, asymmetric reduction of bromoketone come addition to books on chemical technology. catalyzed by cis-aminoindanol oxazaborolidine, etc). Chapter 12 presents asymmetric hydro- The book consists of 13 Chapters divided among genation of carbon-carbon double bonds with petrochemical, synthesis gas and chemicals from organometallic catalysts. synthesis gas, inorganic chemicals, homogene- ous and heterogeneous catalysis, fine chemicals, In Part II of the book titled “Procedures” you biotechnology, and process development. One find detailed expositions of reaction procedures, chapter is devoted to the production of polyeth- eg: Title: 5.2.3 Epoxidation of [E]-2-hexen-1-ol ylene. structural formulas of starting material and product, and conditions; Materials and equip- Chapters 1 and 2 discuss general issues pertain- ment; Procedure-step by step; Table of related ing to chemical industries and give a general alcohols with yield %, ee% (configuration) upon idea of what to expect in the late chapters. epoxidation; Conclusion; and References These are important and individual instructors can build their own presentations around these While biocatalysts may only provide viable and questions and ideas. For instance one can update reliable methods in about 5-10% of all transfor- the figures for energy consumption as it is mations of interest to synthetic organic chemists, known that the world energy consumption from in some cases the biotransformation will provide 1990 to 2020 would nearly double {International the key step in the best method in going from a Energy Outlook, 2000. Energy Information cheap substrate to a high value, optically active Agency (EIA), [Report#: DOE/EIA-0484 fine chemical: Acylase from E.coli is used to (2000)]}. cleave the side chain amide function of fer- mented penicillins to provide 6-aminopenicilloic Chapter 3 gives a general outline of a number of acid en route to semisynthetic penicillins; also, processes in crude oil refining. The authors have hydroxylation of aromatic compounds using mi- blended process technology, chemistry and croorganisms is used to prepare 6- thermodynamics in an elegant manner. The hydroxyisoniootinic acid and (R)-2-(4-hydro flow diagrams in this and other chapters will be xyphenoxy) propanoic acid, important interme- very useful in a design course. Caution has to be diates to pesticides and herbicides respectively. exercised on certain items such as MTBE. EPA in 1999 has recommended that MTBE be re- This volume, in conjunction with the more spe- duced because of its toxic effect on human cific references given, should be of great value health. Thus the shortage of isobutene men- to synthetic organic chemists, especially those tioned on P. 92 might not be relevant with the contemplating to exploit the advantages of in- decreased production of MTBE. corporation biotransformations into their syn- thetic work. Chapters 4 and 5 are well thought out and well Reviewed by Spyros A. Lazaris, Ph.D., FAIC written. The chapters cover topics from funda- mental thermodynamic concepts to reaction rates Chemical Process Technology and mechanism to practical aspects of steam Author: Jacob A. Moulijn cracking in Chapter 4 and the production of syn- Publisher: John Wiley & Sons thesis gas in Chapter 5. ISBN: 0-471-63062-4 Books on chemical processes and process tech- Chapters 6 and 7 deal with bulk inorganic nologies have become rare due to the fact that chemicals: ammonia, urea, sulfuric and nitric ac- most chemical engineering departments no ids. In addition to these inorganic chemicals, longer teach this course. It was good to read a Chapter 6 includes processes for methanol pro- duction. The authors have dealt with homogene- Applications are provided for both physico- ous and heterogeneous catalysis in Chapters 8 chemical processes and analytical methods. and 9. Processes in these chapters could have been included in other chapters as the titles of This book is divided into two sections with the chapters are misleading, as this is not a book twelve chapters. The first section covers the on catalysis. These chapters do not contain fundamentals of chemistry in non-aqueous solu- characterization of catalysts, Langmuir- tion as applied to electrochemical aspects. There Hinshelwood (who mention this mechanism on are four chapters in this section. Chapter 1 is en- pp. 284, 293) or other rate laws, and other topics titled "Properties of Solvents and Solvent Classi- normally found in books on catalysis. In spite of fication". Chapter 2 is entitled "Solvation and this criticism, the processes described are good Complex Formation of and Behavior of examples of catalytic processes. Electrolytes". Chapter 3 is entitled "Acid-base Reactions in Non-Aqueous Solvents". Chapter 4 Chapters 10 and 12 describe the manufacturing is entitled "Redox Reactions in Non-aqueous of important fine chemicals and biochemicals. Solvents". Section 2 is entitled "Electrochemical The authors describe novel methods used in in- Techniques and Their Applications in Non- dustry and include some important considera- Aqueous Solutions". Chapter 5 is entitled tions of batch reactors. In these chapters, the au- "Overview of Electrochemical Techniques". thors describe novel developments in reactor Chapter 6 is entitled "Potentiometry in Non- technology. Chapter 11 is devoted to the produc- Aqueous Solutions". Chapter 7 is entitled "Con- tion of polyethylene, and Chapter 13 focuses on ductimetry in Non-Aqueous Solutions". Chapter process development. 8 is entitled "Polarography and Voltammetry in Non-Aqueous Solutions". Chapter 9 is entitled References at the end of each chapter are ade- "Other Electrochemical Techniques in Non- quate but should be supplemented with journal Aqueous Solutions". Chapter 9 includes electro- references. lytic and coulometric techniques as well as the combination of electrochemical and nonelectro- Overall, this is a welcome addition to books on chemical techniques. Chapter 10 is entitled "Pu- chemical technology. This is a valuable book rification of Solvents and Tests for Impurities". for students and practicing chemical engineers. Chapter 11 is entitled "Selection and Preparation Reviewed by Dabir S. Viswanath, Ph.D., FAIC of Supporting Electrolytes". Chapter 12 is enti- tled "Use of Non-Aqueous Solutions in Modern in Nonaqueous Solutions Electrochemical Technologies". Author: Kosuke Izutsu Publisher: John Wiley & Sons, Inc. Each chapter has a reference section at the end ISBN# 3-527-30516-5 of the chapter. The book has a subject index and Price of Book: $110.00 is 346 pages in length. Electrochemistry in Nonaqueous Solutions by Reviewed by Anne T. Sherren, Ph.D., FAIC Kosuke Izutsu is a book for both the person new to elctrochemistry in nonaqueous solutions and Handbook of Chemical and Environmental those with experience in the field. The book Engineering Calculations should prove useful to both the user and the spe- Author Joseph P. Reynolds, John S. cialist. The differences between electrochemical Jeris, Louis Theodore measurements in non-aqueous systems and those Publisher John Wiley & Sons in aqueous systems are identified. Attention is ISBN 0-471-40228-1 paid to the hazardous and toxic properties of the Price $150.00 solvents. A large number of tables are presented The authors describe the intent of this book as "a in appropriate places. The author focuses on the calculations handbook that could be used as a chemical information derived and the applica- self-teaching aid." That is an interesting and use- tions of the various electrochemical techniques. ful approach to the diverse background required in environmental engineering, but it has not been fully realized in this volume. The book delivers learning philosophy and including worked ex- the promise of a well-indexed reference to useful amples. calculations across the gamut of disciplines used in the environmental sciences. Preface, Contents, Answers to Problems, and Subject Index follow in that order. A structure is provided in the chapter topics and layout that progresses from the fundamentals The focus in this book is on the more common through the most common applications, ending four-, five-, and six-membered systems contain- up with a collection of peripheral topics that are ing one hetero atom (N,O, or S), and little at- normally scattered across a wide range of texts. tempt is made to extend the coverage to more This organization and availability of informa- complex heterocycles. tion, examples, and worked problems is indis- pensable for the practicing environmental tech- Chapter 1 (Introduction to Heterocyclic Chemis- nologist. Most of the topics are covered much try) is, as the title implies, a general one, and better in specific courses, and will be used pri- covers: Aims, Nomenclature, Importance of marily for a review by those trained in those top- Heterocyclic Compounds to Life and Industry, ics. However, the access to relevant calculations General Principles (, non- and applications in many peripheral areas, which aromaticity, and anti-aromaticity, ring strain in are poorly covered in traditional engineering cycloalkanes and their heterocyclic counter- course work, are particularly valuable. Profes- parts), Worked Problems, Summary of Key sionals who have migrated into different job re- Points, Problems, References, and Further Read- sponsibilities will find this reference an immedi- ing. The remaining seven chapters are more ate asset in their daily work. specific, e.g. Chapter 2 is on Pyridine, while Chapter 7 discusses Benzo [b]-, -furan, - As a novel form of textbook, this book is unim- thiophene, and again the approach, with some pressive, lacking the pedagogy necessary to variations, is similar: Aims, Introduction, Reac- really understand the engineering topics. It may tions, Synthesis, Important Derivatives, Worked be too expensive as a stand-alone reference for Problems, Summary of Key Points, Problems, students in addition to other textbooks. But it is Further Reading. ideally written and useful for working profes- sionals, and may also be valuable to senior level The level of discussion ranges from introductory students who are exploring the range of options to intermediate, and though the treatment is not in environmental engineering. It is not a re- comprehensive, it is “solid” and not as decep- placement for specialized discipline texts, but it tively plain as one might surmise from the size is an extremely helpful adjunct to a professional of the book (vi+142 pages); for example, Named engineering library. Reactions discussed include: Bischler- Reviewed by Steven J. Cooke, MChE, FAIC Napieraliski, Chichibabin, Leimgruber-Batcho, Mannich and Vilsmeier; Named-synthese in- Heterocyclic Chemistry clude: Conrad-Limpach-Knorr, Fisher Indole, Author M. Sainsbury Friedländer, Guareschi, Hantzsch, Knorr, Paal- Publisher: John Wiley & Sons, Inc. Knorr, Pictet-Spengler, Pomeranz-Fristsch, and ISBN: 0-471-28164-6 Wender Indole; Worked Problems include Price: $34.95 Problem 9.2: Provide a synthesis of stilbazole Heterocyclic Chemistry is one of the books in (structure given) from 2-Methylpyridine; Prob- the Basic Concepts in Chemistry series. This se- lem 3.1: Provide a synthesis of 1-benzyl-1,2,3,4- ries of books consists of short, single-topic or tetrahydroquinoline from quinoline; or suggest a modular texts, concentrating on the fundamental synthesis of chelidonic acid (structure given) areas of chemistry taught in undergraduate sci- from diethyl oxalate and acetone. Structures of ence courses. Each book “provides” a concise compounds included in the text are, among oth- account of the basic principles underlying a ers, the foul-smelling skatole, the Tyrian purple given subject, embodying an independent- (used to dye the robes of Roman emperors), strychnine (a poison of detective novel fame), factor, physiologically based pharmacokinetic Paraquat (an herbicide interfering with photo- (PBPK), Biologically Based Disposition, Two- synthesis), Nifedipine (a cardiovascular drug), Dimensional Uncertainty Analysis, Two-Stage etc. Clonal Expansion (TSCE), and Monte Carlo Analysis. The text indicates when each of these Although primarily an undergraduate text, the methodologies is appropriate and calls out when main principles that govern heterocyclic chemis- bias can be introduced into a study. try as a whole are addressed in this book, pro- viding a sure foundation for those wishing to Whether the reader is new to risk assessment or widen their interest in heterocyclic chemistry in has experience conducting a risk assessment, the later years. case studies presented in this book provide valu- Reviewed by Spyros A. Lazaris, Ph.D., FAIC able examples of thorough assessments that pre- sent a variety of ways to assess and get the same Human and Ecological Risk Assessment The- result. The discussion shows that there is a need ory and Practice to understand the dose to the majority of the Edited by: Dennis J. Paustenbach adult population and how dose response differs Publisher: John C. Wiley and Sons, Inc. in children. ISBN: 0-471-14747-8 Price: Unknown A broad analysis of risk assessments for con- Human and Ecological Risk Assessment Theory taminated water, contaminated soils, exposures and Practice is divided into 3 sections: Theory to air contaminants, evaluation of occupational (Chapters 1-6); Human Risk Assessment and hazards, risk to foods, risk associated with con- Ecology Risk Assessment Case Studies (Chap- sumer products, and risk to birds is presented. ters 7-24); and Life Cycle, Cost Benefit, Risk Chemicals evaluated in case studies are PAH Communications, and Evolving Issues (Chapters (polycyclic aromatic hydrocarbons), benzene, 25-32). There are 63 contributors. Multiple ref- radon, LET (linear energy transfer) radiation, re- erences are listed after each chapter. Reilly’s fractory ceramic fibers, dioxin, chlordane, forward presents eight valuable lessons from the TCDD, methylene chloride, vinyl chloride, real world of risk assessment. food-borne pathogens, hexavalent chromium, trivalent chromium, inorganic arsenic, beryl- The premise of the theory and practice is that “A lium, cobalt, lead, manganese, nickel, selenium, health risk assessment is a written document organophosphorus pesticides, isofenphos, para- wherein all pertinent scientific information, re- thion, iodine-131, cesium-137, radioactive lan- garding toxicology, human experience, envi- thanum, uranium, elemental mercury, PCBs, ronmental fate, and exposures, are assembled, DDT, natural rubber latex, cadmium, zinc, lead, critiqued, and interpreted.” Whereas “Risk chlorpyrifos, carbaryl, and deltamethrin. Ani- management is the process of evaluating alterna- mal, plant, insect, and water toxicity case studies tive regulatory actions and selecting among are also presented as well as a case study of them.” This book clearly shows that different comparative EIO-LCA steel versus reinforced agencies use differing characterization of risk concrete in bridges. and varied methodologies for risk assessment. The book clearly defines and illustrates the four Evolving issues include children’s health includ- steps of the assessment process through case ing developmental defects, childhood cancer, studies: Hazard Identification, Dose-Response and childhood asthma as well as biomarkers, Assessment, Exposure Assessment, and Risk chemical mixtures, POPs (persistent organic pol- Characterization. The case studies also demon- lutants), and genetically modified foods. strate the application of statistical models and probabilistic analysis including Relative Risk Human and Ecological Risk Assessment Theory Regression, Poisson Regression, Quantal- and Practice is an excellent reference volume on Response, Time-to-Response, Armistage-Doll health risk assessment for toxicologists, indus- Response, Benchmark Dose, uncertainty/safety trial hygienists, environmentalists, chemists, pol- icy analysts, and graduate students. Additions to the first edition include more ecological and Several chapters are dedicated to the analysis of evolving issues and chapters on life cycle analy- air, water, solid, and biological samples for or- sis and cost benefit analysis. ganic compounds, inorganic elements, general Reviewed by Helen Wythe, Ph.D., FAIC chemical properties, and physical characteristics. The descriptions of the analytical techniques Introduction to Environmental Analysis provide general information about how the in- Author: Roger Reeve struments function. In addition, advantages, dis- Publisher: John Wiley & Sons advantages, and limitations of the analytical ISBN: 0-471-49295-7 techniques are touched upon in the descriptions. Price: $45.00 This book, one of the Analytical Techniques in The reader would be disappointed if he/she were the Sciences series of texts, is targeted at under- looking for a detailed explanation of instrumen- graduate students or professionals who possess a tal techniques or an encompassing reference of basic knowledge of instrumentation and a desire environmental sample collection and analytical to learn the basics of environmental analysis. techniques. In conjunction with a training The book includes a series of discussion and course for basic field sample collection and self-assessment questions, which allow the laboratory analytical techniques; however, this reader to focus on the topic being presented. text offers all that an instructor or student would The questions also provide the reader with an desire to have in a text. This book is a good ref- opportunity to evaluate his/her knowledge and erence for environmental professionals because insight relative to the problems and issues being the entire environmental project process from discussed. planning through analysis is presented with enough detail to inform but not so much detail This book contains background information on that the reader is overwhelmed. general environmental contamination, why prob- Reviewed by Stephen T. Zeiner, CPC, MAIC lems exist, issues related to monitoring envi- ronmental contamination, and problems sur- LC/MS Applications in Drug Development rounding the regulation of industrial discharge. Editor: Mike S. Lee The background information is an accurate Publisher: Wiley-Interscience overview of the current environmental land- ISBN# 0-471-40520-5 scape. The information that addressed the con- Price: Unknown cept of bioaccumulation as part of the overall Over the past decade, LC/MS has become environmental pollution concern was especially widely accepted as an integral part in the drug well presented. development process. As one of the Wiley- Interscience Series on Mass Spectrometry (Se- One chapter discusses contaminant transporta- ries Editors, Dominic M. Desiderio and Nico M. tion in the environment, development of sample M. Nibbering), this book focuses on the roles of collection schemes, sample collection tech- LC/MS in the pharmaceutical industry and pro- niques, and sample storage; a well-presented in- vides perspectives on the significant changes in sight into the challenge associated with planning strategies for pharmaceutical analysis. Using se- and execution of sample collection events that lected examples, this book highlights unique ad- accurately define the extent of contamination at vantages of LC/MS and the interrelation be- a site is provided. Descriptions of some sample tween the drug development activities that gen- collection techniques provide the reader with a erate samples and the activities responsible for good representation of the issues surrounding analysis. Future application of LC/MS for ac- representative sample collection. Good informa- celerated drug development and industry trends tion is provided on the basic concepts behind the that deal with sample preparation, chromatogra- determination of where to collect samples and phy, mass spectrometry, and information man- how to preserve the samples once they have agement are also discussed. been collected. The book is comprised of five chapters. Chapter plosive growth and applications must by neces- 1 contains a general introduction on the current sity be brief. But readers should have no diffi- challenges on analytical needs in pharmaceutical culty to find additional information from a list of industry and how the LC/MS techniques are in- up-to-data references included at the end of the tegrated into the drug development process. A book. This book is useful not only for students brief history of LC/MS is also presented. and scholars of , but also for managers and other scientists working in phar- Chapter 2 offers an overview of the drug devel- maceutical industry. As another fine addition to opment process. The four stages of drug devel- the Wiley-Interscience Series on Mass Spec- opment (drug discovery, preclinical, clinical, trometry, it should be in the collections of all re- and manufacturing) are discussed which pro- search libraries. vides a good introduction to readers who are Reviewed by Yushen Guo, Ph.D., FAIC new to pharmaceutical industry. Molecular Modeling of Inorganic Com- Chapter 3 illustrates the accelerated drug devel- pounds, Second Edition opment strategies based on both quantitative and Author: Peter Comba and Trevor W. qualitative process pipelines. Several models Hambley (FTE, sample throughput, elimination, and rate- Publisher: John Wiley & Sons, Inc. determining event) are discussed in related to ISBN# 3-527-29915-7 opportunities for accelerated development. Price: $145.00 Molecular Modeling of Inorganic Compounds, Chapter 4 and chapter 5 provide a brief review Second Edition by Peter Comba and Trevor W. of the LC/MS development process. It also re- Hambley is a book for several audiences. Mo- viewed nine strategies consistently used in drug lecular mechanical modeling of chemical com- development process: standard methods, tem- pounds has been developing for the past 30 plate structure identification, databases, screen- years. This book discusses the recent develop- ing, integration, miniaturization, parallel proc- ments that permit the modeling of larger inor- essing, visualization, and automation. ganic compounds. Initially molecular modeling of inorganic compounds was limited to small Chapter 6, the major chapter of the book, is de- molecules and simple coordination complexes. voted to LC/MS applications. The applications Recent developments permit the extension of are organized according to general drug devel- this field to include organometallic compounds, opment cycles (i.e., drug discovery, preclinical catalysis and the interaction of metal ions with development, clinical development, and manu- biological macromolecules. The number of dif- facturing) to provide a “big picture” for a wide ferent metals and the variety of coordination community of scientists. This sequential ar- numbers, coordination modes, geometries and rangement provides a unique perspective on the electronic states they can adopt, complicate the contributions of LC/MS technique in drug de- application of molecular mechanics to coordina- velopment. tion compounds. For this reason the existing models used for metal containing compounds The last three chapters, all of them are fairly are more complex than those available for or- short, provide the perspectives and personal ganic molecules. Only a few of the commer- thoughts on the future direction of LC/MS appli- cially available packages are able to reliably deal cations in the pharmaceutical industry. Readers with even a small subset of the possible metal- might find less redundancy if the author could based systems. The goals of this book are to combine the three chapters into one. provide an understanding of molecular mechan- ics, to show that it can be applied successfully to Overall, the book provides enough information a wide variety of inorganic compounds. This for reader to understand pharmaceutical LC/MS book is divided into three parts. Part 1 is the the- applications as well as drug development proc- ory section. The theory section includes an in- ess. A book covering such a field of almost ex- troduction to molecular modeling and the his- torical background. Various molecular modeling The chemistry and applications to synthesis of methods are briefly discussed. The para- 1,3-dipolar cycloaddition reactions in the broad meterization, approximations and limitations of context of organic chemistry were first covered molecular mechanics are presented. Computa- in a widely cited two-volume treatise edited by tion and multiple mimima problems are also in- Prof. Albert Padwa and appeared in 1984. Since cluded. Section 2 includes 9 chapters related to then, substantial gains in the synthetic aspects of applications. The authors have attempted to give this chemistry have dominated the area, includ- a wide-ranging coverage of all the areas of inter- ing both methodology development and a body est to inorganic chemists. However, in each of creative and conceptually new applications of chapter, the authors selected the most instructive these [3+2]-cycloadditions in organic synthesis. studies and these are discussed in detail. The The heteroatom-containing cycloadducts may be aim is to show the types of problems and to in- transformed into a variety of other functional- dicate the directions being taken to avoid the ex- ized organic molecules, whether cyclic or isting limitations. The topics include structural acyclic. In recent years, numerous natural and aspects, and steroselectivities, metal ion selectiv- unnatural products have been prepared by syn- ity. Spectroscopy, electron transfer, electronic thetic routes that have 1,3-dipolar cycloaddition effects, , organometallics, as a critical step in their synthesis. and compounds with s-, p- and f-block elements. Part 3 is the practice of molecular mechanics. The 12 chapters of the book were written by sole One chapter effectively discusses the model, the or dual authors from the USA, the UK, and a rules and the pitfalls. The next chapter is a tuto- scattering from other countries (Germany, Japan, rial with 20 exercises. Included in the tutorial are Denmark, Switzerland, Poland, Argentina, and very clear specific directions for building the Taiwan). model with Hyperchem. The tutorials include both icons and screens for the various steps. The Nitrones (Chapt 1) are most useful through their tutorial uses Hyperchem to build the models and ability to generate N- and O-based functionality MOMEC to do the computations. There are four from cycloadducts as well as the potential to in- appendices divided into a glossary, fundamental troduce multiple chiral centers stereochemically. constants, units and conversion factors, software and force fields, and books on molecular model- Silyl and alkyl nitronates (Chapt 2) are discussed ing and reviews on inorganic molecular model- from the point of view of structure, preparation, ing. The list of references is long and there is physical, chemical and spectroscopic properties, also an index. This book includes a CD Disk for and the mechanistic aspects of the dipolar the tutorial and software needed. cycloaddition. Reviewed by Anne T. Sherren, Ph.D., FAIC Azomethine Ylides (Chapt 3) are discussed from 1,3-Dipolar Cycloaddition the point of view of their generation using sili- Editors: Albert Padwa and William H. con-based protocols or alternative generation Pearson procedures, asymmetric reactions, intramolecu- Publisher: John Wiley & Sons, Inc. lar cycloadditions, and metal-mediated reac- ISBN: 0-471-38726-6 tions. Price: $425.00 This book whose full title is: Synthetic Applica- Carbonyl Ylides (Chapt 4) in tandem with sub- tions of 1,3-Dipolar Cycloaddition Chemistry sequent cycloaddition reactions present a highly toward Heterocycles and Natural Products, con- efficient regio- and stereospecific way of ap- stitutes volume 59 in The Chemistry of Hetero- proaching many synthetic problems. cyclic Compounds series. This series, which started in 1950, attempts to make the extraordi- Thiocarbonyl Ylides (Chapt 5) have been recog- narily complex and diverse field of heterocyclic nized as valuable synthetic intermediates for 1,3- chemistry as organized and readily accessible as dipolar cycloaddition chemistry. possible. Chapter 6 describes some recent advances in the Edition will notice that four additional chapters generation and use of Nitrile Oxides as 1,3- have been added featuring the chemistry of tin, dipoles as well as progress in rationalizing the zinc, zirconium, chromium, and iron. Previous reactivity and stereoselectivity of their cycload- chapters have been extensively reworked and ditions. updated; for example the number of Tables to be found in the chapter covering alkali and alkali- With Nitrile Ylides and Nitrile Imines (Chapt 7), earth reagents has increased from 12 to 166. the major development of new chemistry has been the extensive exploration of intramolecular The Manual offers guidance in the form of reactions both in cycloaddition chemistry and in countless schemes, tables, and detailed experi- electrocyclization of 1,3-dipoles with extended mental procedures (substrate, reagents, tempera- conjugation. ture, yield, and ee where applicable) and proto- cols along with recommendations on associated Diazoalkanes (Chapt 8), Azides (Chapt 9) and equipment needs as well as practical advice at Mesoionic Ring Systems (Chapt 10) are fol- critical stages. Indispensable mechanistic in- lowed by more general topics: Effect of Exter- sight is provided, which is crucial to those who nal Reagents (Chapt 11) and Asymmetric Reac- wish to apply these existing tools rationally and tions (Chapt 12). to contribute to the further development of novel reagents and methodology. All contributions are A sampling of products to which 1,3-dipolar written with practical laboratory work in mind, cycloaddition can lead includes: antimalocrial “be it for undergraduate and graduate students alkaloids, adamantane-spirothiazolines, quino- learning the trade, or for the experienced indus- carcin, triquinane sesquiterpenes, heterocyclic trial synthetic chemist expanding his/her reper- dendrimers, epi-hippodamine, zaragozic acids, toire of additional versatile reagents and cata- A and B, phyllanthocin, papuamine, lysts.” and carzinophilin, to mention just a few. “Pro- tocols” discussed include: Ditami, Hashimoto, Organoalkali Chemistry, contributed by Man- Hodgson, Houk-Jäger, Padwa, Kanemasa, fred Schlosser (Univ. of Lausanne), takes up ap- Merck, etc. A non-chemist who casually opens proximately one third of the book; it is a treasure this book may become curious and want to read trove of facts and information with an astound- more about: facial selectivity, caged com- ing 2,100 references to the original literature. pounds, PM3 calculations, WIN inhibitor, Evan’s auxiliary, 5 or 6-exo-dig process, one-pot , by James Marshall (Univ. procedures, Oppolzer’s sultan, push-pull ylides, of Virginia), discusses preparation and reactions or LUMO. of tetraalkyltin compounds, stannates (acyl-, vi- nyl-, allylic-, allenic, etc.), and also - Printing errors are very rare, almost unnotice- catalyzed coupling of organostannates (stille able, and no more serious than desilyation (p. couplings) in over 100 pages (176 references). 170) instead of desilylation. For those in the field, this is an excellent reference. , by Keith Smith (Univ. Reviewed by Spyros A. Lazaris, Ph.D., FAIC of Wales), covers inter alia safety, handling, re- producibility and selection of reactions and re- Organometallics in Synthesis: A Manual 2nd agents (70 pages, 175 references). Edition Editor: Manfred Schlosser Organoaluminum Chemistry was written by Hi- Publisher: John Wiley & Sons, Ltd sashi Yamamoto (Nagoya Univ.) and covers re- ISBN: 0-471-98416-7 lated chemistry and topics such as the “Ate Price: $149.50 complex and its reactivity” and specialized top- This voluminous (x+1243 pages) book is an up- ics (Ziegler-Natta and related complexation dated (’02) and greatly enlarged edition of its chemistry) in 40 pages and 72 references. precursor that appeared in 1994. Users of the 1st Organozinc Chemistry, by Eiichi Nakamura All the contributing authors are experts in their (Univ. of Tokyo), discusses structures, reactiv- respective fields to which they contributed. In ity, and preparation of organozinc compounds, this collection of chapters, they have distilled addition to C-O, C-N, C-C double/ multiple and condensed all pertinent knowledge on or- bond, the Simmons-Smith reaction, and substitu- ganometallic use in synthetic organic chemistry. tion at carbon by organozinc reagents (70 pages, This is a very useful and practical compendium 193 references). indeed. Reviewed by Spyros A. Lazaris, Ph.D., FAIC Organocopper Chemistry, contributed by Bruce H. Lipshutz (Univ. of California), discusses Polymer Blends copper complexes derived from organolithium Editor: D. R. Paul, C. B. Bucknall and Grignard reagents, by transmetallation and Publisher: John Wiley & Sons, Inc. miscellaneous copper reagents (140 pages, 256 ISBN# 0-471-24825-8 references). Price: Unknown This two-volume set on polymer blends summa- Organotitanium Chemistry was written by Man- rizes both the science base and the progress in fred T. Reetz (Max-Plank-Institut) who puts the technological developments and the com- special emphasis on the use of titanium (IV) in mercial applications. Through contributions C-C bond formation, especially on the titanation from near sixty highly respected experts from of classical carbanions of C-H-acidic com- around the world, this book offers a coherent pounds, which generates selective reagents for presentation on this subject while the style and Grignard, aldol, and Michael additions, and sub- content of each chapter are coordinated to ensure stitution reactions (90 pages, 462 references). It a smooth and sensible transition from topic to took a “titanic” effort to assemble all this mate- topic. Each chapter provides enough back- rial. ground information without sacrificing the most important issues critically gleaned from the lit- Ei-ichi Negishi (Purdue Univ.) gave us Or- eratures, which makes this book useful for both ganozirconium Chemistry, systematically dis- the beginners as well as the experts. cussing the preparation of organozirconium compounds and their reactions of systemic util- Volume1 is devoted to the formulation aspect of ity, especially zirconocene and related deriva- polymer blends. It contains mainly the physics, tives (130 pages, 225 references). chemistry, and processing issues associated with the formation of polymer blends and the evalua- Martin F. Semmelthack of Princeton University tion and control of their structure. The chapters is the author of Organoiron and Organochro- are organized into three well-balanced sections: mium Chemistry, discussing each type of com- thermodynamics (including seven chapters on plex including preparation and handling, then statistical thermodynamics of polymer solution the mechanism and associated aspects of the and blends, polymer-polymer interactions based scope and limitations, and finally specific appli- on mean field approximations, hydrogen bond- cations with detailed procedures (120 pages, 300 ing systems, polymer blends as viewed by ana- references). logue , crystalline polymer blends, blends of rigid-chain polymers, thermodynamics Chemistry by Louis F. of polyolefin blends); characterization (includ- Hegedus (Colorado State Univ.) is the crowning ing chapters on morphology characterization by chapter of the book. Palladium complexes, we microscopy techniques, viscoelastic characteri- are told, have a very rich chemistry and are zation of polymer blends, optical characteriza- among the most readily available, easily pre- tion, and neutron scattering); and structure for- pared and easily handled of transition metal mation (formulation and characterization of complexes, and promote a very wide range of thermoset-thermoplastic blends, chemical reac- organic transformations. tions in blends based on condensation polymers, morphology and properties of blends containing block copolymers, factors influencing the mor- line polymer, from polymer blends to microfi- phology of immisiscible polymer blends in melt brillar reinforced composites); elastomeric processing, reactive compatibilization, and proc- blends (elastomer, thermoplastic vulcanizates); essing aids). and recycling of polymer blends and mixtures.

Volume 2 deals with the performance of poly- Overall, this set of books covers a broad range mer blends and primarily concerned with how of theoretical and experimental discussions and blends perform in practical situations. This vol- provides an authoritative resource on the struc- ume is divided into five sections: mechanical ture-property relationships for polymer blends. properties and fracture resistance (including The case studies are explained well and the in- chapters on quasielastic mechanical properties, troductory material is concise. A complete ref- application of fracture mechanics for characteri- erence list follows and enriches each chapter al- zation of toughness, characterizing toughness lowing the reader to use it as a starting point to using standard empirical tests, deformation carry on further researches on these topics. Both mechanisms in rubber-polymer interface, core- researchers and application engineers will bene- shell impact modifiers, toughening semicrystal- fit from this book. People will find this book line thermoplastics, toughening of epoxies, fa- indispensable as a reference for further devel- tigue-crack propagation); blending for specific opments on the subjects. performance (transmission and reflection of light Reviewed by Yushen Guo, Ph.D., FAIC in multiphase media, thermomechanical per- formance, barrier materials by blending); rein- force blends (reinforced polymer, liquid crystal-

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