DOCSLIB.ORG

JUN I 13998 Scienct LIBRARIES This Doctoral Thesis Has Been Examined by a Committee of the Department of Chemistry As Follows

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
JUN I 13998 Scienct LIBRARIES This Doctoral Thesis Has Been Examined by a Committee of the Department of Chemistry As Follows THE DEVELOPMENT OF ORGANOTIN REAGENTS FOR ORGANIC SYNTHESIS by David Scott Hays B. S. Chemistry, University of Illinois Submitted to the Department of Chemistry in Partial Fulfillment of the Requirements for the Degree of DOCTOR OF PHILOSOPHY IN ORGANIC CHEMISTRY at the Massachusetts Institute of Technology June 1998 © Massachusetts Institute of Technology, 1998 All rights reserved Signature of Author Department of Chemistry May 14, 1998 Certified by Gregory C. Fu t' Thesis Supervisor Accepted by Dietmar Seyferth Chairman, Departmental Committee on Graduate Students JUN I 13998 scienct LIBRARIES This doctoral thesis has been examined by a committee of the Department of Chemistry as follows: Professor Peter H. Seeberger I_ _ /1 Chairman Professor Gregory C. Fu J _J Thesis Supervisor Professor Rick L. Danheiser THE DEVELOPMENT OF ORGANOTIN REAGENTS FOR ORGANIC SYNTHESIS by David Scott Hays Submitted to the Department of Chemistry on May 14, 1998 in partial fulfillment of the requirements for the Degree of Doctor of Philosophy at the Massachusetts Institute of Technology ABSTRACT A method for the intramolecular pinacol coupling of dialdehydes and ketoaldehydes is described. The method was found to be useful for synthesizing 1,2-cyclopentanediols with very high degrees of diastereoselectivity in favor of the cis stereochemistry. 1,2- Cyclohexanediols were generated with lower degrees of stereoselection. This free radical chain process involves as the key steps: 1) an intramolecular addition of a tin ketyl radical to a pendant carbonyl group, followed by 2) a rapid intramolecular homolytic displacement by an oxygen radical at the tin center to liberate an alkyl radical. The development of a Bu 3 SnH-catalyzed carbon-carbon bond forming reaction (the reductive cyclization of enals and enones) is described, followed by a catalytic variant of the Barton-McCombie deoxygenation reaction. Both of these methods rely on the reduction of an intermediate Sn-O species to a Sn-H species by a silicon hydride reagent in the turnover step. A new fundamental reaction of organotin compounds is described: the generation of Sn-H bonds by treatment of tin amides with silicon hyrdides. The scope of organotin hydride catalysis was broadened to include reactions which generate Sn-N bonds, and in this context, a new Bu3SnH-catalyzed reduction of azides to amines was developed. Thesis Supervisor: Gregory C. Fu Title: Assistant Professor of Chemistry ACKNOWLEDGMENTS Throughout my educational career, I have been fortunate to have been taught by some of the best, and they deserve a special thanks. Most notably: Miss Woolard (6th grade); Ms. Whitis (7th grade English); Mr. Wilken (8th grade math); Mr. Leech (9th grade science; Mr. Wenner (Jr. High instructor, high school spiritual advisor); Ken Johnston (Jr. High instructor). The teachers in the Newark High English Department stand out for encouraging me to state my opinion and not minding too much that it differed from their own: Mrs. Jones; Ms. Harriman; and Ms. Anderson. Without my experiences in the sciences at Newark High, I probably wouldn't be writing this Thesis. Mr. MacGregor, Mr. Miller, and Dr. Doyle all deserve recognition for their excellent curricula which prepared me so well for college. And of course, Mr. Holekamp, who went far above and beyond the call of duty in taking me under his wing. He is truly a star. A number of individuals have had a significant impact on my professional career. I will always be indebted to my friends and mentors at the Eastman Kodak Company who took unselfish interests in my success. First, Ms. Jeanne Kaeding, who taught me the difference between labwork and bookwork. I will always be deeply indebted to Dr. (Professor) Mike Detty for his chemistry lessons, friendship, and advice, and I hope we have the chance to work together again. The experience I gained while working with Dr. Doug Bugner will always stand out as some of the most valuable: in particular, his early confidence that I could handle much more responsibility than I'm sure I had earned. At the University of Illinois, I was fortunate to have the opportunity to work with a model scientist and academician: Professor Scott Denmark. I couldn't have been given a better undergraduate project, nor could I have asked for a better balance of guidance and freedom. My collaboration with Dr. David Forbes led to some of the most productive 12-hour days (and 12-ounce curls) I've ever known. I will always be grateful to my thesis advisor, Professor Greg Fu, for allowing me to help start up his lab and his projects, and I expect to hear lots of great chemistry from him over the course of what will certainly be a long academic career. My blood brothers and sisters (fellow Fu group pioneers Chris Garrett, Diego Hoic, Mike Amendola, and Matthias Scholl) deserve a recognition which couldn't be accommodated between the covers of this Thesis. I hope that my future coworkers are as talented, honest, dedicated, responsible, trustworthy, and open to discussion as they have been, as well as the remaining Fu group members: Shuang Qiao, Adam Littke, Dr. Ken Stockman, Dr. Jordi Tormo, Dr. Rosa Lopez, Jack Liang, Dr. Hallie Latham, Beata Tao, and Michael Lo. My parents have always served as an endless source of inspiration, and I only hope I can do the same for my own children. They, as well as Jack and Phoebe Harden, helped to make the last 5 years a success. And finally my wife Jennifer, the most natural and capable mother on the planet, who earned this degree as much as I did. It would not have been possible without her unconditional optimism and support. She, along with our children Samuel and Brooke, taught me everything that is important. DEDICATION To my beautiful wife Jennifer, and to our spectacularchildren Samuel, Brooke, and those not yet conceived. PREFACE Parts of this thesis have been adapted from the following articles co-written by the author. Hays, D. S.; Fu, G. C. "Metal Hydride Mediated Intramolecular Pinacol Coupling of Dialdehydes and Ketoaldehydes," J. Am. Chem. Soc. 1995, 117, 7283-7284. Hays, D. S.; Fu, G. C. "Organotin Hydride Catalyzed Carbon-Carbon Bond Formation: Radical-Mediated Reductive Cyclization of Enals and Enones," J. Org. Chem. 1996, 61, 4-5. Hays, D. S.; Scholl, M.; Fu, G. C. "Organotin Hydride-Catalyzed Conjugate Reduction of a,x,-Unsaturated Ketones," J. Org. Chem. 1996, 61, 6751-6752. Lopez, R. M.; Hays, D. S.; Fu, G. C. "Bu 3 SnH-Catalyzed Barton-McCombie Deoxygenation of Alcohols," J. Am. Chem. Soc. 1997, 119, 6949-6950. Hays, D. S.; Fu, G. C. "A New Method for Generating Sn-H Bonds: Reactions of Tin Amides with Silicon Hydrides," J. Org. Chem. 1997, 62, 7070-7071. Tormo, J.; Hays, D. S.; Fu, G. C. "Diastereoselective Synthesis of P-Amino Alcohols via Bu 3 SnH-Mediated Reductive Cyclization of Carbonyl-Oxime Ethers," J. Org. Chem. 1998, 63, 201-202. Hays, D. S.; Fu, G. C. "The Development of Bu 3 SnH-Catalyzed Processes: Efficient Reduction of Azides to Amines," J. Org. Chem., 1998, 63, 2796-2797. TABLE OF CONTENTS ABBREVIATIONS INTRODUCTION CHAPTER 1. Bu 3SnH-MEDIATED INTRAMOLECULAR PINACOL COUPLING OF DIALDEHYDES AND KETOALDEHYDES Background Results and Discussion Experimental References CHAPTER 2. DEVELOPMENT OF ORGANOTIN HYDRIDE- CATALYZED PROCESSES I. SYNTHETIC TRANSFORMATIONS INVOLVING Sn-O INTERMEDIATES Part 2.1 Introduction Part 2.2 Organotin Hydride Catalyzed Carbon-Carbon Bond Formation: Radical-Mediated Reductive Cyclization of Enals and Enones Background Results and Dicussion Experimental Part 2.3 Discovery and Optimization of the Bu3SnH-Catalyzed Barton-McCombie Deoxygenation of Alcohols Background Results and Discussion Experimental 104 Part 2.4 References 108 CHAPTER 3. DEVELOPMENT OF ORGANOTIN HYDRIDE- CATALYZED PROCESSES II. SYNTHETIC TRANSFORMATIONS INVOLVING Sn-N INTERMEDIATES 111 Part 3.1 Introduction 112 Part 3.2 A New Method for Generating Sn-H Bonds: Reactions of Tin Amides with Silicon Hydrides 114 Background 114 Results and Discussion 116 Experimental 123 Part 3.3 Bu3SnH-Catalyzed, Silicon Hydride-Mediated Reduction of Azides to Amines 146 Background 146 Results and Discussion 146 Experimental 155 Part 3.4 Organotin-Catalyzed, Silicon Hydride-Mediated Room Temperature Reduction of Azides to Amines 174 Background 174 Results and Discussion 176 Experimental 179 Part 3.5 References 184 APPENDIX 186 ABBREVIATIONS ACHN 1,1'-Azobis(cyclohexnanecarbonitrile) AIBN 2,2'-Azobisisobutyronitrile d doublet DBATO bis(dibutylacetoxytin) oxide eq equation equiv equivalent(s) GC gas chromatography h hour(s) HRMS high resolution mass spectroscopy IR infrared min minute(s) NMR nuclear magnetic resonance PMHS polymethylhydrosiloxane PMHS dimer 1,3-bis(trimethylsiloxy)-1,3-dimethyldisiloxane ppm parts per million q quartet quint quintet r.t. room temperature s singlet t triplet THF tetrahydrofuran TLC thin-layer chromatography Introduction Over the last 30-40 years, organotin reagents have become indispensible tools for synthetic organic chemists.1 Their utility can largely be attributed to the unmatched ability with which organotin species participate in radical chain reactions, thus carving out a niche distinct from polar chemistry. As a consequence, modes of reactivity which cannot be accessed in the polar realm are readily available in a mild, neutral, often chemo- and stereoselective manner 2 by using organotin reagents. As a testimony to the synthetic utility of organotin reagents, chemists continue to widely use them despite two significant drawbacks: toxicity3-5 and difficulty in removal of organotin residues from crude reaction mixtures.6 Both of these issues could be addressed by a protocol which requires less than stoichiometric quantities of the organotin reagent.7-10 Thus, the development of organotin catalysis is the central focus of this thesis. The development of a new catalytic cycle can be envisioned as occurring in three stages. In the first stage, a mechanism for catalysis must be proposed.
Load more

Recommended publications
  • Chemistry Department 32.Pdf (10.36Mb)
    THE FABRICATION OF NANOMETRIC METAL SULFIDES FROM XANTHATE PRECURSORS By ALAN PIQUETTE Bachelor of Arts Western State College of Colorado Gunnison, Colorado 2002 Submitted to the Faculty of the Graduate College of the Oklahoma State University In partial fulfillment of The requirements for The Degree of DOCTOR OF PHILOSOPHY December, 2007 THE FABRICATION OF NANOMETRIC METAL SULFIDES FROM XANTHATE PRECURSORS Thesis Approved: _______________ __Allen Apblett___ ______________ Thesis Advisor ________________ Nicholas Materer_____ __________ _____________ __LeGrande Slaughter___ __________ _______________ ____Jim Smay___ _______________ _____________ __A. Gordon Emslie___ ____________ Dean of the Graduate College ACKNOWLEDGEMENTS It is with my utmost sincere appreciation that I acknowledge my thesis advisor, Dr. Allen W. Apblett, for his support, guidance, and motivation. He provided a research environment that was both friendly and challenging, which made my years in his group enjoyable and rewarding. His broad range of knowledge was something of which I was happy to take advantage. His dedication to teaching and research is something that will be a positive influence on me for the rest of my scientific career. I would like to express gratitude to my committee members: Dr. Nicholas Materer, Dr. LeGrande Slaughter, and Dr. Jim Smay, for their assistance, advice, guidance, and support throughout the years. I am deeply grateful to all my colleagues and friends in the chemistry department. I would specifically like to thank Sulaiman Al-Fadul, Mohammed Al-Hazmi, Zeid Al- Othmann, Mohamed Chehbouni, Satish Kuriyavar, and Tarek Trad for showing me the ropes, for their valuable discussions, continuous encouragement, and for all the help they extended during the course of my stay in the Apblett Group.
    [Show full text]
  • I the Synthesis of Papyracillic Acids: Application of the Tandem Chain
    University of New Hampshire University of New Hampshire Scholars' Repository Doctoral Dissertations Student Scholarship Winter 2011 I The synthesis of papyracillic acids: Application of the tandem chain extension-acylation reaction II Diastereoselective synthesis of beta-methyl-gamma-keto esters through the utility of an L- serine auxiliary Jennifer R. Mazzone University of New Hampshire, Durham Follow this and additional works at: https://scholars.unh.edu/dissertation Recommended Citation Mazzone, Jennifer R., "I The synthesis of papyracillic acids: Application of the tandem chain extension- acylation reaction II Diastereoselective synthesis of beta-methyl-gamma-keto esters through the utility of an L-serine auxiliary" (2011). Doctoral Dissertations. 644. https://scholars.unh.edu/dissertation/644 This Dissertation is brought to you for free and open access by the Student Scholarship at University of New Hampshire Scholars' Repository. It has been accepted for inclusion in Doctoral Dissertations by an authorized administrator of University of New Hampshire Scholars' Repository. For more information, please contact [email protected]. I. THE SYNTHESES OF PAPYRACILLIC ACIDS: APPLICATION OF THE TANDEM CHAIN EXTENSION-ACYLATION REACTION II. DIASTEREOSELECTIVE SYNTHESIS OF p-METHYL-y-KETO ESTERS THROUGH THE UTILITY OF AN L-SERINE AUXILIARY BY Jennifer R. Mazzone B.A., Assumption College, 2006 DISSERTATION Submitted to the University of New Hampshire in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy in Chemistry December, 2011 UMI Number: 3500790 All rights reserved INFORMATION TO ALL USERS The quality of this reproduction is dependent upon the quality of the copy submitted. In the unlikely event that the author did not send a complete manuscript and there are missing pages, these will be noted.
    [Show full text]
  • Catalytic Pyrolysis of Plastic Wastes for the Production of Liquid Fuels for Engines
    Electronic Supplementary Material (ESI) for RSC Advances. This journal is © The Royal Society of Chemistry 2019 Supporting information for: Catalytic pyrolysis of plastic wastes for the production of liquid fuels for engines Supattra Budsaereechaia, Andrew J. Huntb and Yuvarat Ngernyen*a aDepartment of Chemical Engineering, Faculty of Engineering, Khon Kaen University, Khon Kaen, 40002, Thailand. E-mail:[email protected] bMaterials Chemistry Research Center, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, 40002, Thailand Fig. S1 The process for pelletization of catalyst PS PS+bentonite PP ) t e PP+bentonite s f f o % ( LDPE e c n a t t LDPE+bentonite s i m s n HDPE a r T HDPE+bentonite Gasohol 91 Diesel 4000 3500 3000 2500 2000 1500 1000 500 Wavenumber (cm-1) Fig. S2 FTIR spectra of oil from pyrolysis of plastic waste type. Table S1 Compounds in oils (%Area) from the pyrolysis of plastic wastes as detected by GCMS analysis PS PP LDPE HDPE Gasohol 91 Diesel Compound NC C Compound NC C Compound NC C Compound NC C 1- 0 0.15 Pentane 1.13 1.29 n-Hexane 0.71 0.73 n-Hexane 0.65 0.64 Butane, 2- Octane : 0.32 Tetradecene methyl- : 2.60 Toluene 7.93 7.56 Cyclohexane 2.28 2.51 1-Hexene 1.05 1.10 1-Hexene 1.15 1.16 Pentane : 1.95 Nonane : 0.83 Ethylbenzen 15.07 11.29 Heptane, 4- 1.81 1.68 Heptane 1.26 1.35 Heptane 1.22 1.23 Butane, 2,2- Decane : 1.34 e methyl- dimethyl- : 0.47 1-Tridecene 0 0.14 2,2-Dimethyl- 0.63 0 1-Heptene 1.37 1.46 1-Heptene 1.32 1.35 Pentane,
    [Show full text]
  • Title Crystallization of Stereospecific Olefin Copolymers (Special Issue on Physical Chemistry) Author(S) Sakaguchi, Fumio; Kita
    Crystallization of Stereospecific Olefin Copolymers (Special Title Issue on Physical Chemistry) Author(s) Sakaguchi, Fumio; Kitamaru, Ryozo; Tsuji, Waichiro Bulletin of the Institute for Chemical Research, Kyoto Citation University (1966), 44(4): 295-315 Issue Date 1966-10-31 URL http://hdl.handle.net/2433/76134 Right Type Departmental Bulletin Paper Textversion publisher Kyoto University Crystallization of Stereospecifie Olefin Copolymers Fumio SAKAGUCHI,Ryozo KITAMARU and Waichiro TSUJI* (Tsuji Laboratory) Received August 13, 1966 The stereoregularity of isotactic poly(4-methyl-1-pentene) was characterized and isomorphism phenomena were examined for the copolymeric systems of 4-methyl-1-pentene with several olefins in order to study the crystallization phenomena in these olefin copoly- mers polymerized with stereospecific catalysts. The structural heterogeneity or the fine crystalline structure of poly(4-methyl-1-pentene) could be correlated with its molecular structure by viewing this stereoregular homopolymer as if it were a copolymer. Cocrystallization or isomorphism phenomenon was recognized for the copolymeric systems of 4-methyl-1-pentene with butene-1, pentene-1, decene-1 and 3-methyl-1-butene, while no evidence of the phenomenon was obtained for the copolymeric systems with styrene and propylene. The degree of the isomorphism of those copolymers was discussed with the informations on the crystalline phases obtained from the X-ray study, on the constitution of the copolymeric chains in the amorphous phases obtained from the viscoelastic studies and on the other thermodynamical properties of these systems. INTRODUCTION Many works have been made with regard to the homopolymerization of olefins with stereospecific catalysts, i. e. complex catalysts composed of the combination of organometallic compound and transitional metallic compound.
    [Show full text]
  • Process Synthesis
    PROCESS SYNTHESIS DALE F. RUDD University of Wisconsin Madison, Wisconsin 53706 INTRODUCTION In the words of Webster, synthesis is "the proper way to approach process development. In combining of often diverse conceptions into a co­ these theories of process development, each syn­ herent whole" and analysis is "an examination thesis step defines an analysis problem the solu­ of a complex, its elements and their relations." tion of which provides data required for further Synthesis refers to the more inventive aspects of synthesis steps. Further, it became apparent that engineering and analysis to the more scientific. this organization of alternating synthesis and Both are required in the development of industrial analysis steps begs the development of educational processes. material for the early stages of engineering edu­ Since World War II engineering education has cation. moved strongly towards analysis, with the intro­ In this report we examine the development of duction of courses which analyse individual pro­ a first course in engineering in which synthesis cess operations and phenome,na. rransport phe­ and analysis are taught simultaneously. Elemen­ nomena, unit operations, process control, thermo­ tary new principles of process synthesis are com­ dynamics and other engineering science courses bined with the classic analysis techniques of greatly strengthened engineering education by material and energy balancing. Emphasis is on showing how things are and how they work. the development of process technology rather than Unfortunately, there was not a parallel de­ on the analysis of existing processes. velopment in the teaching of synthesis. The teach­ ing of how things ought to be rather than how RESEARCH IN PROCESS SYNTHESIS they are.
    [Show full text]
  • A Low Temperature Structure of Nonane-1,9-Diaminium Chloride Chloroacetate: Hydroxyacetic Acid (1:1)
    J Chem Crystallogr (2011) 41:703–707 DOI 10.1007/s10870-010-9957-6 ORIGINAL PAPER A Low Temperature Structure of Nonane-1,9-Diaminium Chloride Chloroacetate: Hydroxyacetic Acid (1:1) Agnieszka Paul • Maciej Kubicki Received: 24 February 2010 / Accepted: 31 December 2010 / Published online: 14 January 2011 Ó The Author(s) 2011. This article is published with open access at Springerlink.com Abstract The crystal structure of nonane-1,9-diaminium protons and to form salts with both, organic and inorganic chloride chloroacetate–hydroxyacetic acid (1:1) was deter- acids, together with a significant flexibility of the chain mined by X-ray diffraction at 100(1)K. The asymmetric fragment and tendency towards creation of the highly unit is composed of diaminium dication, chloroacetate and symmetric networks, can be used in so-called crystal chloride anions, and neutral hydroxyacetic acid molecule. engineering [2], i.e. in designing new materials with The aliphatic chain of 1,9-diamine is fully extended and it expected features. Such a predictable motifs in the crystal deviates only slightly from the perfect all-trans confor- structures, giving rise to a layer structure, were already mation. The two acidic residues are also nearly planar. The investigated in the series of hexane-1,6-diamine and layer structure is obtained as a consequence of hydrogen butane-1,4-diamine salts [3, 4]. bond interactions of a different lengths, with N–H and O–H Only five structures deposited in the Cambridge Struc- groups playing the role of donors and oxygen atoms and tural Database [5] (no multiple determinations, herein and chloride cations as acceptors.
    [Show full text]
  • Highly Efficient Olefin Isomerization Catalyzed by Metal Hydrides Derives from Dirhodium(Ii) Carboxylates and Catecholborane
    HIGHLY EFFICIENT OLEFIN ISOMERIZATION CATALYZED BY METAL HYDRIDES DERIVES FROM DIRHODIUM(II) CARBOXYLATES AND CATECHOLBORANE Gene A. Devora and Michael P. DoyleL' * Department of Chemistry, Trinity University, San Antonio, Texas 78212, USA Abstract. Dirhodium(ll) tetraacetate in combination with catecholborane catalyzes the iso- merization of alkenes and dienes. Effective isomerization occurs at 80-135°C with the use of only 0.1 mol % rhodium acetate. With 2-methyl-1,5-hexadiene the disubstituted double bond is prefer- entially isomerized. In addition, hydrogen transfer hydrogenation occurs with 1,4-cyclohexadienes. The mechanism of these reactions is proposed to involve organoborane addition across a Rh-0 bond which activates the catalyst for isomerization and hydrogenation. INTRODUCTION Catalytic isomerization of alkenes is a characteristic transformation of transition metal hy- drides that often accompanies hydrogenation1 and is one of the most thoroughly studied catalytic reactions.2"4 Compounds of cobalt, nickel, palladium, platinum, rhodium, and ruthenium are effective,2 but other transition metal compounds have also been employed for catalytic isomeriza- tions.2"4 Although the nature of this transformation is dependent on the catalyst, selectivity for alkene isomerization generally favors reactions with monosubstituted ethylenes over di- and tri-sub- stituted ethylenes. In the course of our investigations of the catalytic effectiveness of dirhodium(ll) tetrakis(carboxylates) we have uncovered a useful methodology for the generation of rhodium hydride species that, as we now report, are surprisingly effective for the isomerization of alkenes as well as for hydrogen transfer hydrogenation. MATERIALS AND METHODS Reactions were performed in a round bottom flask equipped with a screw cap that was fitted with a septum for convenient withdrawal of aliquots.
    [Show full text]
  • SAFETY DATA SHEET 1,9-Dibromo-Nonane-2,8-Dione According to Regulation (EC) No 1907/2006, Annex II, As Amended
    Revision date: 03/01/2020 Revision: 1 SAFETY DATA SHEET 1,9-Dibromo-nonane-2,8-dione According to Regulation (EC) No 1907/2006, Annex II, as amended. Commission Regulation (EU) No 2015/830 of 28 May 2015. SECTION 1: Identification of the substance/mixture and of the company/undertaking 1.1. Product identifier Product name 1,9-Dibromo-nonane-2,8-dione Product number FD173289 CAS number 91492-76-1 1.2. Relevant identified uses of the substance or mixture and uses advised against Identified uses Laboratory reagent. Manufacture of substances. Research and development. 1.3. Details of the supplier of the safety data sheet Supplier Carbosynth Ltd 8&9 Old Station Business Park Compton Berkshire RG20 6NE UK +44 1635 578444 +44 1635 579444 [email protected] 1.4. Emergency telephone number Emergency telephone +44 7887 998634 SECTION 2: Hazards identification 2.1. Classification of the substance or mixture Classification (EC 1272/2008) Physical hazards Not Classified Health hazards Not Classified Environmental hazards Not Classified Additional information Caution. Not fully tested. 2.2. Label elements Hazard statements NC Not Classified 2.3. Other hazards No data available. SECTION 3: Composition/information on ingredients 3.1. Substances Product name 1,9-Dibromo-nonane-2,8-dione 1/8 Revision date: 03/01/2020 Revision: 1 1,9-Dibromo-nonane-2,8-dione CAS number 91492-76-1 Chemical formula C₉H₁₄Br₂O₂ SECTION 4: First aid measures 4.1. Description of first aid measures General information Get medical advice/attention if you feel unwell. Inhalation Remove person to fresh air and keep comfortable for breathing.
    [Show full text]
  • Chemistry Grade Span 9/10
    Chemistry Grade Span 9/10 Carbon and Carbon Compounds Subject Matter and Methodological Competencies • name the allotropes of carbon and use them to explain the relationship between its structure and properties • state the characteristics of the oxides of carbon • conduct experiments to o detect evidence of carbon dioxide o detect evidence of carbonates (using carbon dioxide detection) o describe the natural formation and decay processes of carbonates and hydrogen carbonates and use this to explain a simple model of the carbon cycle Natural Gas and Crude Oil Subject Matter and Methodological Competencies • identify natural gas, crude oil and coal as fossil fuels • explain the causes and consequences of increasing carbon dioxide concentrations in the atmosphere • discuss the economic and ecological consequences of the production and transport of natural gas and crude oil • apply knowledge of substance mixtures and substance separation using the example of fractional distillation of petroleum • describe the molecular structure of the gaseous alkanes using chemical formulas, structural formulas and simplified structural formulas • conduct experiments to o examine the flammability and solubility of selected alkanes o determine that water and carbon dioxide are the products of combustion o explain the relationship between the construction, properties and uses of important alkanes (e.g. methane - natural gas, propane and butane - liquid gas, octane - gasoline, decane - diesel, octadecane - paraffin candle wax) o explain the cohesion of alkane
    [Show full text]
  • September 17, 2007
    Pre-Feasibility Report M/s. Neogen Chemicals Ltd. 1 1. Introduction M/s. Neogen Chemicals Ltd. is a new unit located at Plot No. Z/96/B SEZ Dahej, District: Bharuch, Gujarat. Now, the unit proposes to manufacture different type of synthetic organic dyes and pesticide products at above sited address. 2. Cost of Project Cost of existing project is 55 crore &, out of which 5 crore will be used for Environment Management System. 3. Production Capacity Production capacity is prescribe below: List of Products Sr. Name of Products Quantity No. (MT/Year) (MT/month) 1 Bromination and Chlorination of Alcohols 1.1. Ethyl Bromide 3500 291.67 1.2. n-Propyl Bromide 1.3. Iso Propyl Bromide 1.4. n-Butyl Bromide 1.5. Iso Butyl Bromide 1.6. Sec-Butyl Bromide 1.7. n-Hexyl Bromide 1.8. n-Heptyl Bromide 1.9. n-Octyl Bromide 1.10. n-Decyl Bromide 1.11. Lauryl Bromide 1.12. Cetyl Bromide 1.13. Myristyl Bromide 1.14. Stearyl Bromide 1.15. 1,2 Dibromo Ethane 1.16. 1,3 Dibromo Propane 1.17. 1,4 Dibromo Butane 1.18. 1,5 Dibromo pentane M/s. Neogen Chemicals Ltd. 2 Sr. Name of Products Quantity No. (MT/Year) (MT/month) 1.19. 1,6 Dibromo Hexane 1.20. 1 Chloro 2 Ethyl Hexane 1.21. 6 Chloro 1 Hexanol 1.22. 3 Chloro Propanol 1.23. 1,6 Dichloro Hexane 1.24. Cyclo Propyl Methyl Bromide 1.25. Cyclo Pentyl Bromide 1.26. Cyclo Pentyl Chloride 2. Bromination of Organic Acids and Esterification thereof 2.1.
    [Show full text]
  • Chapter 2: Alkanes Alkanes from Carbon and Hydrogen
    Chapter 2: Alkanes Alkanes from Carbon and Hydrogen •Alkanes are carbon compounds that contain only single bonds. •The simplest alkanes are hydrocarbons – compounds that contain only carbon and hydrogen. •Hydrocarbons are used mainly as fuels, solvents and lubricants: H H H H H H H H H H H H C H C C H C C C C H H C C C C C H H H C C H H H H H H CH2 H CH3 H H H H CH3 # of carbons boiling point range Use 1-4 <20 °C fuel (gasses such as methane, propane, butane) 5-6 30-60 solvents (petroleum ether) 6-7 60-90 solvents (ligroin) 6-12 85-200 fuel (gasoline) 12-15 200-300 fuel (kerosene) 15-18 300-400 fuel (heating oil) 16-24 >400 lubricating oil, asphalt Hydrocarbons Formula Prefix Suffix Name Structure H CH4 meth- -ane methane H C H H C H eth- -ane ethane 2 6 H3C CH3 C3H8 prop- -ane propane C4H10 but- -ane butane C5H12 pent- -ane pentane C6H14 hex- -ane hexane C7H16 hept- -ane heptane C8H18 oct- -ane octane C9H20 non- -ane nonane C10H22 dec- -ane decane Hydrocarbons Formula Prefix Suffix Name Structure H CH4 meth- -ane methane H C H H H H C2H6 eth- -ane ethane H C C H H H H C H prop- -ane propane 3 8 H3C C CH3 or H H H C H 4 10 but- -ane butane H3C C C CH3 or H H H C H 4 10 but- -ane butane? H3C C CH3 or CH3 HydHrydorcocaarrbobnos ns Formula Prefix Suffix Name Structure H CH4 meth- -ane methane H C H H H H C2H6 eth- -ane ethane H C C H H H H C3H8 prop- -ane propane H3C C CH3 or H H H C H 4 10 but- -ane butane H3C C C CH3 or H H H C H 4 10 but- -ane iso-butane H3C C CH3 or CH3 HydHrydoroccarbrobnsons Formula Prefix Suffix Name Structure H H
    [Show full text]
  • Supercritical Pyrolysis of N-Decane Sean Bagley Louisiana State University and Agricultural and Mechanical College, [email protected]
    Louisiana State University LSU Digital Commons LSU Doctoral Dissertations Graduate School 2010 Supercritical Pyrolysis of n-Decane Sean Bagley Louisiana State University and Agricultural and Mechanical College, [email protected] Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_dissertations Part of the Chemical Engineering Commons Recommended Citation Bagley, Sean, "Supercritical Pyrolysis of n-Decane" (2010). LSU Doctoral Dissertations. 4000. https://digitalcommons.lsu.edu/gradschool_dissertations/4000 This Dissertation is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Doctoral Dissertations by an authorized graduate school editor of LSU Digital Commons. For more information, please [email protected]. SUPERCRITICAL PYROLYSIS OF N-DECANE A Dissertation Submitted to the Graduate Faculty of the Louisiana State University Agricultural and Mechanical College in partial fulfillment of the requirements for the degree of Doctor of Philosophy in The Department of Chemical Engineering by Sean Bagley B.S., Louisiana State University, 2003 December 2010 Acknowledgements I gratefully acknowledge the Air Force Office of Scientific Research, for providing the necessary funding for this research. I would like to thank Dr. Arthur Lafleur and Ms. Elaine Plummer of the Massachusetts Institute of Technology and Dr. John Fetzer of Chevron Research for providing reference standards and/or UV spectra of polycyclic aromatic hydrocarbons to my professor. I would like to thank my professor, Dr. Judy Wornat, for her wisdom and patience. The members of my group, Elmer Ledesma, Jorge Oña, Shiju Thomas, Michelle Walker, Jerome Robles, Franz Ehrenhauser, and Nimesh Poddar, each of whom contributed to my project in innumerable ways.
    [Show full text]