DOCSLIB.ORG

United States Patent (19) 11 Patent Number: 4,696,773 Lukenbach Et Al

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
United States Patent (19) 11 Patent Number: 4,696,773 Lukenbach Et Al United States Patent (19) 11 Patent Number: 4,696,773 Lukenbach et al. 45 Date of Patent: Sep. 29, 1987 54) PROCESS FOR THE PREPARATION OF (56) References Cited SETHONCACID U.S. PATENT DOCUMENTS (75) Inventors: Elvin R. Lukenbach, Somerset; 4,499,028 2/1985 Longley .............................. 260/513 Prakash Naik-Satam, East Windsor, both of N.J.; Anthony M. Schwartz, FOREIGN PATENT DOCUMENTS Rockville, Md. 0151934 11/1981 Fed. Rep. of Germany ...... 260/513 (73) Assignee: Johnson & Johnson Baby Products Primary Examiner-Alan Siegel Company, New Brunswick, N.J. Attorney, Agent, or Firm-Steven P. Berman 21) Appl. No.: 882,660 57) ABSTRACT Fied: Jul. 7, 1986 A process for the preparation of isethionic acid involv 22 ing the reaction of sodium isethionate and hydrogen 51 Int. Cl. ............................................ C07C 143/02 chloride in an alcoholic solvent is described. (52) U.S.C. ................................................ 260/513 R 58) Field of Search ........................ 260/513 R, 513 B 3 Claims, No Drawings 4,696,773 1 2 These and other objects of the present invention will PROCESS FOR THE PREPARATION OF become apparent to one skilled in the art from the de SETHONCACD tailed description given hereinafter. FIELD OF INVENTION SUMMARY OF THE INVENTION This invention relates to a process for the preparation This invention relates to a novel process for the prep of isethionic acid involving the reaction of sodium ise aration of isethionic acid. thionate and hydrogen chloride in an alcoholic solvent. BACKGROUND OF THE INVENTION 10 DETALED DESCRIPTION OF THE This invention relates to a process for the preparation INVENTION ofisethionic acid. Isethionic acid can also be referred to The present invention relates to a process comprising as 2-hydroxyethane sulfonic acid and is of the formula reacting sodium isethionate with hydrogen chloride in HOCH2CH2SO3.H. Numerous processes have been the presence of a suitable alcohol resulting in the forma suggested in the literature for the preparation of isethi 15 tion of isethionic acid. onic acid and the related isethionate salts. This reaction should be carried out in an alcoholic A number of these methods are disclosed in C. M. solvent system wherein the alcohol is a straight or Suter, "The Organic Chemistry of Sulfur", John Wiley branched chain lower alkanol containing from 1 to 4 & Sons, Inc. New York, 1944 (reprinted 1969), pps. carbon atoms. A preferred alcohol solvent is ethanol. 130-132. An early preparation involved the action of 20 In the process of the present invention it is important sulfur trioxide upon ethyl alcohol or ether to yield ethi that anhydrous sodium isethionate and anhydrous hy onic acid which can then be hydrolyzed to isethionic drogen chloride are utilized to prevent contamination acid. The sulfonation of barium ethyl sulfate produces and insure the purity and yield of the desired product. similar results. Another preparation involves the action The reaction is preferably carried out at room tem of sulfur trioxide upon ethylene to form crystals of 25 perature but may be carried out at elevated tempera carbyl sulfate that hydrolyze first to ethionic acid and tures up to the boiling point of the solvent, if the rate of then to isethionic acid. The hydrolysis of ethionic acid reaction requires. After completion, the resultant prod to produce isethionic acid and sulfuric acid has also uct is filtered to remove the insoluble solids, and then been described in Wooten and Lloyd, J. Org. Chem. 39, the alcohol and axcess hydrogen chloride is distilled off 2112 (1974) and Weinreich and Jufreso, Bull. Soc. 30 yielding substantially pure isethionic acid. The yields Chem. France 1965 (3) 787; which indicate that the approach 100% bases on the sodium isethionate pro hydrolysis readily occurs under aqueous acid condi vided that equimolar amounts of sodium isethionate and tions. These processes all have in common the require hydrogen chloride or an excess of hydrogen chloride is ment of the use of sulfur trioxide, a violent reagent utilized. requiring careful and special handling techniques, and 35 Isethionic acid is useful in electroplating; in the manu the intermediacy of carbyl sulfate or ethionic acid, facture of inks; in the preparation of resins; as a reaction which must then be hydrolyzed in aqueous solution to catalyst, for example, isethionic acid serves as a catalyst isethionic acid resulting in the production of sulfuric in the condensation reaction of aniline with formalde acid as a by-product. Due to the use of water as a sol hyde to prepare diaminodiphenylmethanes; and as a vent the resulting isethionic acid is obtained in a dilute reagent in the preparation of surfactants which are use solution and of concentrated is obtained as the monohy ful in the formulation of personal care and cleaning drate. Generally, these processes are not used to obtain products. isethionic acid perse but rather the hydrolysis mixture Specific embodiments of the present invention are is neutralized with alkaline earth bases such as calcium illustrated by the following representative examples. It or barium salts to precipitate the insoluble sulfate fol 45 will be understood, however, that the invention is not lowed by the addition of alkali thereby forming the confined to the specific limitations set forth in the indi isethionate salt. vidual examples, but rather to the scope of the ap U.S. Pat. No. 4,499,028 discloses a process for the pended claims. preparation of isethionic acid by treating alkali metal 50 EXAMPLE I isethionate with hydrochloric acid in aqueous medium. In a suitable reaction apparatus equipped with con This process requires excess hydrochloric acid which is denser, stirrer and cooling means and protected from not easily recovered for reuse. This process results in atmospheric moisture, are combined 78 g of dry sodium yields of about 80% isethionic acid containing alkali isethionte and 100 ml anhydrous ethanol. Excess dry metalisethionates and water. 55 hydrogen chloride gas is introduced by a suitable dis None of the methods of preparing isethionic acid persion means into the stirred mixture with cooling for disclosed in the prior art yield isethionic acid substan about hour, such that the temperature does not exceed tially free of contaminants such as chloride ion, sodium 60° C. After removal of precipitated sodium chloride by ion, sulfuric acid and water nor are they economical. filtration, the alcohol and excess hydrogen chloride are It is therefore an object of the present invention to distilled off under vacuum. The residue of 123 g of provide a novel process for the preparation ofisethionic liquid isethionic acid solidifies on cooling. It has an acid. equivalent weight (sodium hydroxide titration) of 135, It is a further object of the invention to provide a and is free of chloride ion. process for the preparation of isethionic acid which avoids undesirable contaminants. 65 EXAMPLE II It is a still further object of the invention to provide In a suitable reactor equipped with condenser, stirrer an economically desirable process for the preparation of and cooling means protected from atmospheric mois isethionic acid. ture is placed 505 g of ethanol. Dry hydrogen chloride 4,696,773 3 4 gas is introduced by a suitable dispersion means until EXAMPLE V 154 g (3.44 mole) is absorbed. In a suitable reaction apparatus equipped with stir To the above solution is added with stirring 503 g (3.4 ring, vacuum and heating utilities, and equipped with moles) of sodium isethionate in portions over 1 hour. distillation condenser are combined lauric acid (200 The mixture is stirred for an additional 30 min. It is then parts) and isethionic acid (150 parts, 20% excess). The reaction mixture is heated under < 1 mmHg pressure to filtered and the solvent removed by distillation to pro 125 C. over 2 hours, to produce lauroylisethionic acid duced 435 g ofisethionic acid (quantitative yield, equiv of 87% activity. After cooling to 75° C., the reaction alent weight 126, with negligible chloride content). 10 mass is transferred to a solution of 175 parts of trietha nolamine in 1000 parts of water. The mixture is vigor EXAMPLE III ously stirred at 45 C. to produce a homogeneous solu In a suitable reactor is placed 2-propanol (500g) and tion at pH 6.2 of the triethanolamine salt of lauroyl isethionic acid of 24.4% activity (96% conversion) HCl gas is introduced with cooling until 141 g (3.91 15 which is useful as a surfactant. moles) is absorbed. In addition to the preferred embodiments described Sodium isethionate (193g, 1.3 moles) is added, and herein, other embodiments, arrangements and varia the mixture stirred at room temperature for 16 hours. tions within the scope of the invention and the scope of the appended claims will be apparent to those skilled in After filtration and evaporation of HC/alcohol 164 g of 20 the art. isethionic acid (quantitative yield) is obtained. What is claimed is: 1. A process for the preparation of isethionic acid EXAMPLE IV under anhydrous conditions comprising contacting an In a suitable reactor are combined 1000 ml of isopro hydrous sodium isethionate with anhydrous hydrogen panol solution of hydrogen chloride (HCl content 111 25 chloride in the presence of an alcohol solvent. 2. The process of claim 1 wherein the solvent is a g, 3.08 moles) and sodium isethionate (228 g, 1.54 lower alkanol containing from 1 to 4 carbon atoms. moles). The mixture is heated at the boil for two hours. 3. The process of claim 2 wherein the solvent is etha After cooling, filtration and evaporation, 194g ofisethi nol. onic acid (quantitative yield) is recovered. 30 se k sk s s 35 40 45 50 55 60 65 .
Load more

Recommended publications
  • Thesis, Dissertation
    THE COENZYME M BIOSYNTHETIC PATHWAY IN PROTEOBACTERIUM XANTHOBACTER AUTOTROPHICUS PY2 by Sarah Eve Partovi A dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Biochemistry MONTANA STATE UNIVERSITY Bozeman, Montana January 2018 ©COPYRIGHT by Sarah Eve Partovi 2018 All Rights Reserved ii DEDICATION I dedicate this dissertation to my family, without whom none of this would have been possible. My husband Ky has been a part of the graduate school experience since day one, and I am forever grateful for his support. My wonderful family; Iraj, Homa, Cameron, Shireen, Kevin, Lin, Felix, Toby, Molly, Noise, Dooda, and Baby have all been constant sources of encouragement. iii ACKNOWLEDGEMENTS First, I would like to acknowledge Dr. John Peters for his mentorship, scientific insight, and for helping me gain confidence as a scientist even during the most challenging aspects of this work. I also thank Dr. Jennifer DuBois for her insightful discussions and excellent scientific advice, and my other committee members Dr. Brian Bothner and Dr. Matthew Fields for their intellectual contributions throughout the course of the project. Drs. George Gauss and Florence Mus have contributed greatly to my laboratory technique and growth as a scientist, and have always been wonderful resources during my time in the lab. Members of the Peters Lab past and present have all played an important role during my time, including Dr. Oleg Zadvornyy, Dr. Jacob Artz, and future Drs. Gregory Prussia, Natasha Pence, and Alex Alleman. Undergraduate researchers/REU students including Hunter Martinez, Andrew Gutknecht and Leah Connor have worked under my guidance, and I thank them for their dedication to performing laboratory assistance.
    [Show full text]
  • NON-HAZARDOUS CHEMICALS May Be Disposed of Via Sanitary Sewer Or Solid Waste
    NON-HAZARDOUS CHEMICALS May Be Disposed Of Via Sanitary Sewer or Solid Waste (+)-A-TOCOPHEROL ACID SUCCINATE (+,-)-VERAPAMIL, HYDROCHLORIDE 1-AMINOANTHRAQUINONE 1-AMINO-1-CYCLOHEXANECARBOXYLIC ACID 1-BROMOOCTADECANE 1-CARBOXYNAPHTHALENE 1-DECENE 1-HYDROXYANTHRAQUINONE 1-METHYL-4-PHENYL-1,2,5,6-TETRAHYDROPYRIDINE HYDROCHLORIDE 1-NONENE 1-TETRADECENE 1-THIO-B-D-GLUCOSE 1-TRIDECENE 1-UNDECENE 2-ACETAMIDO-1-AZIDO-1,2-DIDEOXY-B-D-GLYCOPYRANOSE 2-ACETAMIDOACRYLIC ACID 2-AMINO-4-CHLOROBENZOTHIAZOLE 2-AMINO-2-(HYDROXY METHYL)-1,3-PROPONEDIOL 2-AMINOBENZOTHIAZOLE 2-AMINOIMIDAZOLE 2-AMINO-5-METHYLBENZENESULFONIC ACID 2-AMINOPURINE 2-ANILINOETHANOL 2-BUTENE-1,4-DIOL 2-CHLOROBENZYLALCOHOL 2-DEOXYCYTIDINE 5-MONOPHOSPHATE 2-DEOXY-D-GLUCOSE 2-DEOXY-D-RIBOSE 2'-DEOXYURIDINE 2'-DEOXYURIDINE 5'-MONOPHOSPHATE 2-HYDROETHYL ACETATE 2-HYDROXY-4-(METHYLTHIO)BUTYRIC ACID 2-METHYLFLUORENE 2-METHYL-2-THIOPSEUDOUREA SULFATE 2-MORPHOLINOETHANESULFONIC ACID 2-NAPHTHOIC ACID 2-OXYGLUTARIC ACID 2-PHENYLPROPIONIC ACID 2-PYRIDINEALDOXIME METHIODIDE 2-STEP CHEMISTRY STEP 1 PART D 2-STEP CHEMISTRY STEP 2 PART A 2-THIOLHISTIDINE 2-THIOPHENECARBOXYLIC ACID 2-THIOPHENECARBOXYLIC HYDRAZIDE 3-ACETYLINDOLE 3-AMINO-1,2,4-TRIAZINE 3-AMINO-L-TYROSINE DIHYDROCHLORIDE MONOHYDRATE 3-CARBETHOXY-2-PIPERIDONE 3-CHLOROCYCLOBUTANONE SOLUTION 3-CHLORO-2-NITROBENZOIC ACID 3-(DIETHYLAMINO)-7-[[P-(DIMETHYLAMINO)PHENYL]AZO]-5-PHENAZINIUM CHLORIDE 3-HYDROXYTROSINE 1 9/26/2005 NON-HAZARDOUS CHEMICALS May Be Disposed Of Via Sanitary Sewer or Solid Waste 3-HYDROXYTYRAMINE HYDROCHLORIDE 3-METHYL-1-PHENYL-2-PYRAZOLIN-5-ONE
    [Show full text]
  • United States Patent Office Patented Mar
    3,243,454 United States Patent Office Patented Mar. 29, 1966 2 time. A preferred method of carrying out our process 3,243,454 PROCESS OF PREPARING ALKAL METAL is to reflux an aqueous solution of an alkali metal is SETIONATES ethionate and then remove excess water by evaporation. Donald L. Klass, Barrington, and Thomas W. Martinek, The following non-limiting examples illustrate the scope Crystal Lake, ii., assignors, by mesne assignments, to of our invention and, to a limited extent, compare our Union Oil Corpany of California, Los Angeles, Calif., invention with the prior art. a corporation of California Example I No Drawing. Filed Apr. 4, 1962, Ser. No. 184,939 6 Claims. (C. 260-513) A 5.0-g. portion of sodium vinyl sulfonate was dis O Solved in 50 ml. of water and the solution was refluxed This invention relates to new and useful improvements for 6 hours, with air-blowing. Evaporation of the excess in methods for the preparation of alkali metal salts of Water gave sodium isethionate in quantitative yield. The isethionic acid. identification of the product was by elemental analysis: The preparation of the alkali metal salts of isethionic calculated C, 16.22% wt., H, 3.40% wt., S, 21.65% wt., acid from ethylene oxide and an alkali metal bisulfite using 15 Na, 15.53% wt. Found: C, 16.8% wt., H, 3.4% wt., S, high pressure equipment is known in the art (see Sexton 22.2% wt., Na, 15.3% wt. Infrared analysis indicated et al. U.S. Patent 2.810,747).
    [Show full text]
  • Abstract Reports: Student-Originated Studies Projects, 1973. INSTITUTION National Science R0,4Dation, Washington, D.C
    DOCUMENT RESUME ED 100 708 SE 018 648 AUTHOR Hill, Berton F., Ed. TITLE Abstract Reports: Student-Originated Studies Projects, 1973. INSTITUTION National Science r0,4dation, Washington, D.C. REPORT NO NSF-74-33 PUB DATE Dec 73 NOTE .88p.; Presented at the Project Reporting Meeting (Washington, D.C., December 26-29, 1973) EDRS PRICE MF-$0.75 HC-$13.80 PLUS POSTAGE DESCRIPT(IRS *Abstracts; College Students; *Environmental Research; Health; *Research; Science Education; *Sciences; *Student Projects; Student Research; Water Pollution Control IDENTIFIERS National Science Foundation; NSF; Research. Reports ABSTRACT Presented is a collection of research reports of college-age investigators. The work of the students demonstrates one way in which reliable andilluminating data.on local problems of societal importance can be gathered and analyzed in relatively short time-spans for very little money. Water-related studies, health-related and basic environmental studies are prei,-nted in abstract form: Included in each paper are the college in which the student investigators were enrolled, the participants in each particular research endeavor, the student project director, and faculty advisor. (EB) I I U.S. DEPARTMENT OF HEALTH, EDUCATION & WELFARE NATIONAL INSTITUTE OF EDUCATION THIS DOCUMENT HAS BEEN REPRO DUCED EXACTLY AS RECEIVED FROM THE PERSON OR ORtiANIZATION ORIGIN ATING IT POINTS OF VIEW OR OPINIONS STUDENT-ORIGINATED STATED DO NOT NECESSARILY REPRE SENT OFFICIAL NATIONAL INSTITUTE OF STUDIES PROJECTS EDUCATION POSITION OR POLICY BEST COPY AVAILABLE 1973 Abstract Reports Presented at Meetings in Washington, D.C. December 26-29, 1973 NATIONAL SCIENCE FOUNDATION bo Washington, D.C. 20550 to NSF 74.33 STUDENT-ORIGINATED STUDIES PROJECTS 1973 Abstract Reports Presented at the Project Reporting Meeting December 26-29, 1973 Washington, D.C.
    [Show full text]
  • Cir Expert Panel Meeting June 10-11, 2013
    PINK Safety Assessment of Isethionate Salts as Used in Cosmetics CIR EXPERT PANEL MEETING JUNE 10-11, 2013 Commitment & Credibility since 1976 Memorandum To: CIR Expert Panel Members and Liaisons From: Christina L. Burnett Scientific Writer/Analyst Date: May, 2013 Subject: Draft Tentative Report on Isethionate Salts Way back in December 2008, the CIR Expert Panel re‐reviewed Sodium Cocoyl Isethionate and determined to re‐open the report to allow for the development and incorporation of new reproductive and developmental data from Industry. The data at the time were not ready and the Panel agreed to table the report until the data were ready. The data were supposed to be available by the end of 2009. Meanwhile, at the March 2009 meeting with the newest Panel members seated, the Panel agreed to expand the ingredient report to include additional isethionate salts to bring the total number of ingredients reviewed in this safety assessment to 12. Nearly 5 years have passed and we never received the promised data directly from Industry. We have been recently informed that the data were submitted for REACH and can be accessed through the European Chemicals Agency (ECHA) website (http://echa.europa.eu/en/information‐on‐chemicals). While we are waiting on legal clarification in general on how we can proceed with utilizing copyrighted material from the ECHA site for unknown third party data, we have been given permission to use the data on sodium isethionate (CAS # 1562‐00‐1) from all involved parties. These data have been incorporated into the report. In the time that has passed, the reported uses to the FDA VCRP database have doubled for sodium cocoyl isethionate.
    [Show full text]
  • United States Patent (10) Patent No.: US 6,537,532 B1 Torgerson Et Al
    USOO6537532B1 (12) United States Patent (10) Patent No.: US 6,537,532 B1 Torgerson et al. (45) Date of Patent: *Mar. 25, 2003 (54) SILICONE GRAFTED THERMOPLASTIC (52) U.S. Cl. ................ 424/70.12; 424/70.1; 424/70.11; ELASTOMERIC COPOLYMERS AND HAIR 424/70.15; 424/70.16; 424/78.08; 424/78.17; AND SKIN CARE COMPOSITIONS 424/78.24 CONTAINING THE SAME (58) Field of Search ............................. 424/70.12, 70.1, 424/70.11, 70.15, 70.16, 78.08, 78.17, 78.24 (75) Inventors: Peter Marte Torgerson, Washington Court House, OH (US); Sanjeev (56) References Cited Midha, Blue Ash, OH (US) U.S. PATENT DOCUMENTS (73) Assignee: The Procter & Gamble Company, 4.011,376 A 3/1977 Tomalia et al. ............. 528/392 Cincinnati, OH (US) 4,988,506 A * 1/1991 Mitra et al. ............ 424/70.122 5,106,609 A * 4/1992 Bolich, Jr. et al............. 424/70 (*) Notice: Subject to any disclaimer, the term of this 5,916,547 A * 6/1999 Torgerson et al. ....... 424/70.12 patent is extended or adjusted under 35 5,919,439 A * 7/1999 Torgenson et al. ..... 424/70.122 U.S.C. 154(b) by 0 days. * cited by examiner This patent is Subiect to a terminal dis- Primary Examiner Thurman- K. Page p ASSistant Examiner-Liliana Di Nola-Baron claimer. (74) Attorney, Agent, or Firm-Brent M. Peebles (21) Appl. No.: 09/342,726 (57) ABSTRACT (22) Filed: Jun. 29, 1999 The present invention relates to water or alcohol soluble or dispersible Silicone grafted thermoplastic elastomeric Related U.S.
    [Show full text]
  • Aldrich Phosphorus and Sulfur Compounds
    Aldrich Phosphorus and Sulfur Compounds Library Listing – 822 spectra Subset of Aldrich FT-IR Library related aldehydes and ketones. The Aldrich Material-Specific FT-IR Library collection represents a wide variety of the Aldrich Handbook of Fine Chemicals' most common chemicals divided by similar functional groups. These spectra were assembled from the Aldrich Collections of FT-IR Spectra Editions I or II, and the data has been carefully examined and processed by Thermo Fisher Scientific. Aldrich Phosphorus and Sulfur Compounds Index Compound Name Index Compound Name 245 ((1R)-(ENDO,ANTI))-(+)-3- 651 (2S)-(+)-GLYCIDYL 3- BROMOCAMPHOR-8- SULFONIC NITROBENZENESULFONATE,99% ACID, AMMONIUM SALT 649 (2S)-(+)-GLYCIDYL TOSYLATE, 246 ((1S)-(ENDO,ANTI))-(-)-3- 99% BROMOCAMPHOR-8- SULFONIC 352 (3,4-TOLUENEDITHIOLATO(2- ACID, AMMONIUM SALT ))ZINC HYDRATE 292 (+)-10- 402 (3- DICYCLOHEXYLSULFAMOYL-L- CHLOROPROPYL)DIPHENYLSULF ISOBORNEOL, 98% ONIUM TETRAFLUORO- BORATE, 242 (+/-)-10-CAMPHORSULFONIC ACID 97% MONOHYDRATE, 98% 295 (7R)-10,10-DIMETHYL-5-THIA-4- 243 (+/-)-10-CAMPHORSULFONIC ACID, AZATRICYCLO- (5.2.1.03,7)DEC-3- SODIUM SALT, 97% ENE-5,5-D 778 (-)-1-CHLORO-3-TOSYLAMIDO-7- 296 (7S)-10,10-DIMETHYL-5-THIA-4- AMINO-2- HEPTANONE AZATRICYCLO- (5.2.1.03,7)DEC-3- HYDROCHLORIDE, 98% ENE-5,5-D 291 (-)-10- 488 (PHENYLSULFINYL)(PHENYLSULF DICYCLOHEXYLSULFAMOYL-D- ONYL)METHANE, 95% ISOBORNEOL, 98% 439 (PHENYLSULFONYL)ACETONITRI 629 (-)-2,3-BUTANEDIOL DI-P- LE, 98% TOSYLATE, 99% 417 (R)-(+)-METHYL P-TOLYL 306 (-)-SINIGRIN MONOHYDRATE, 98% SULFOXIDE, 99%
    [Show full text]
  • Studies on the Physiological Role of Taurine in Mammalian Tissues'
    STUDIES ON THE PHYSIOLOGICAL ROLE OF TAURINE (2-aminoethane sulfonic acid) IN MAMMALIAN TISSUES by MOHAMED AKBERALI REMTULLA B.Sc, University of British Columbia, 1974 A THESIS SUBMITTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE.DEGREE OF DOCTOR OF PHILOSOPHY in THE FACULTY OF GRADUATE STUDIES in THE DEPARTMENT OF PATHOLOGY (Faculty of Medicine) We accept this thesis as conforming to the required standard THE UNIVERSITY OF BRITISH COLUMBIA AUGUST, 1979 (e) Mohamed Akberali Remtulla, 19 79 In presenting this thesis in partial fulfilment of the requirements for an advanced degree at the University of British Columbia, I agree that the Library shall make it freely available for reference and study. I further agree that permission for extensive copying of this thesis for scholarly purposes may be granted by the Head of my Department or by his representatives. It is understood that copying or publication of this thesis for financial gain shall not be allowed without my written permission. Department of The University of British Columbia 2075 Wesbrook Place Vancouver, Canada V6T 1W5 ii ABSTRACT 'Studies on the Physiological Role of Taurine in Mammalian Tissues' Mohamed A. Remtulla Ph.D. (Pathology) Taurine (2-aminoethane sulfonic acid) is one of the most abundant free amino acids found in mammalian brain, heart and muscle. Taurine levels have also been shown to be altered in certain disease states. A physiological role for taurine in the maintainance of excitatory activity in muscle and nervous tissues has been suggested; however its possible mechanism of action is still uncertain. Early work on the pharmacological actions of taurine involved its possible conversion to isethionic acid (2-hydroxyethane sulfonic acid), a strong anion.
    [Show full text]
  • New Intermediates, Pathways, Enzymes and Genes in the Microbial Metabolism of Organosulfonates
    New intermediates, pathways, enzymes and genes in the microbial metabolism of organosulfonates Dissertation zur Erlangung des akademischen Grades des Doktors der Naturwissenschaften (Dr. rer. nat.) an der Universität Konstanz Fachbereich Biologie vorgelegt von Sonja Luise Weinitschke Konstanz, Dezember 2009 Tag der mündlichen Prüfung: 26.02.2010 1. Referent: Prof. Dr. Alasdair M. Cook 2. Referent: Prof. Dr. Bernhard Schink „In der Wissenschaft gleichen wir alle nur den Kindern, die am Rande des Wissens hier und da einen Kiesel aufheben, während sich der weite Ozean des Unbekannten vor unseren Augen erstreckt.“ Sir Isaac Newton Meiner Familie gewidmet Contributions during my PhD thesis to other projects than mentioned in the main Chapters: Denger, K., S. Weinitschke, T. H. M. Smits, D. Schleheck and A. M. Cook (2008). Bacterial sulfite dehydrogenases in organotrophic metabolism: separation and identification in Cupriavidus necator H16 and in Delftia acidovorans SPH-1. Microbiology 154: 256-263. Krejčík, Z., K. Denger, S. Weinitschke, K. Hollemeyer, V. Pačes, A. M. Cook and T. H. M. Smits (2008). Sulfoacetate released during the assimilation of taurine-nitrogen by Neptuniibacter caesariensis: purification of sulfoacetaldehyde dehydrogenase. Arch. Microbiol. 190: 159-168. Denger, K., J. Mayer, M. Buhmann, S. Weinitschke, T. H. M. Smits and A. M. Cook (2009). Bifurcated degradative pathway of 3-sulfolactate in Roseovarius nubinhibens ISM via sulfoacetaldehyde acetyltransferase and (S)-cysteate sulfo-lyase. J. Bacteriol. 191: 5648-5656. An erster Stelle möchte ich mich herzlich bei Prof. Dr. Alasdair M. Cook bedanken für die Betreuung und die Möglichkeit, an einem so interessanten Projekt forschen zu dürfen. Mein herzlicher Dank gilt außerdem… … Prof.
    [Show full text]
  • The Development and Improvement Of
    FLUORESCENT REAGENTS TO IMPROVE THE ANALYTICAL INFRASTRUCTURE OF CAPILLARY ELECTROPHORETIC SEPARATIONS A Dissertation by MING-CHIEN LI Submitted to the Office of Graduate Studies of Texas A&M University in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY May 2012 Major Subject: Chemistry FLUORESCENT REAGENTS TO IMPROVE THE ANALYTICAL INFRASTRUCTURE OF CAPILLARY ELECTROPHORETIC SEPARATIONS A Dissertation by MING-CHIEN LI Submitted to the Office of Graduate Studies of Texas A&M University in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY Approved by: Chair of Committee, Gyula Vigh Committee Members, Coran Watanabe Daniel Romo Victor Ugaz Head of Department, David H. Russell May 2012 Major Subject: Chemistry iii ABSTRACT Fluorescent Reagents to Improve the Analytical Infrastructure of Capillary Electrophoretic Separations. (May 2012) Ming-Chien Li, B.S., Tankang University; M.S., National Tsing Hua University Chair of Advisory Committee: Dr. Gyula Vigh Two types of fluorescent molecules had been designed and synthesized to improve the analytical infrastructure of capillary electrophoretic separations. First, a hydrophilic version of the permanently cationic acridine-based fluorophore, HEG2Me2-DAA was ex synthesized. HEG2Me2-DAA has a λ max of 490 nm which matches the 488 nm line of the commonly used argon ion laser. The emission spectra of HEG2Me2-DAA are pH- independent. HEG2Me2-DAA was used in capillary electrophoresis with an aqueous background electrolyte and was found to be free of the detrimental peak tailing of the acridine orange-based fluorophore that was caused by adsorption on the inner wall of the fused silica capillary. Bovine serum albumin was labeled with excess of the designed amine reactive reagent and the lowest concentration at which the tagged bovine serum albumin was tested was 15 nM.
    [Show full text]
  • Harry's Cosmeticology 9Th Edition Volume 2
    NINTH EDITION Harry’s Cosmeticology Harry’s Cosmeticology 9th Edition © 2015 Chemical Publishing Co., Inc. All rights reserved. No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning or otherwise, except as permitted under Sections 107 or 108 of the 1976 United Stated Copyright Act, without either the prior written permission of the Publisher. Requests to the Publisher for permission should be addressed to the Publisher, Chemical Publishing Company, through email at [email protected]. The publisher, editors and authors make no representations or warranties with respect to the accuracy or completeness of the contents of this work and specifically disclaim all warranties, including without limitation warranties of fitness for a particular purpose. Volume One - ISBN: 978-0-8206-01762 Volume Two - ISBN: 978-0-8206-01779 Volume Three - ISBN: 978-0-8206-01786 eBook - ISBN: 978-0-8206-01793 First Edition Chemical Publishing Company www.chemical-publishing.com Printed in the United States of America About the Editor-in-Chief Meyer R. Rosen CChem, CPC, CChE, CFEI, DABFE, DABFET, FAIC Meyer R. Rosen is President of Interactive Consulting, Inc. (www.chemicalconsult.com). He is a Thought-Leader and expert in the field of Technical Marketing and multi-industry Technology Transfer Applications including, but not limited to: cosmetics and personal care, applied rheology, applied surface and interfacial chemistry, polymers, organosilicones, professional editing and custom preparation of Mind-Maps® for the organization and presentation of complex information. Mr. Rosen is a Chartered Chemist and Fellow of the Royal Society of Chemistry (London); a Fellow of the American Institute of Chemists and both a Nationally Certified Professional Chemist and Certified Professional Chemical Engineer.
    [Show full text]
  • Chemical Safety and Waste Management Manual
    Chemical Safety and Waste Management Manual University of Alabama at Birmingham Department of Occupational Health & Safety Chemical Safety Division 2002 EDITION 1. INTRODUCTION In a comparatively short time, the University of Alabama at Birmingham has gained significant recognition as a center of excellence for teaching, medical services and research programs. This is a highly commendable achievement and one that could not have been realized without the continued support and dedication of faculty, staff members, and employees. Similar unfailing cooperation and support are necessary for the institution to be equally successful in its development of a comprehensive occupational health and safety program for the protection of University personnel, students, and the surrounding community. An important part of this program is concerned with the safe and prudent handling of chemicals and their proper legal disposal as regulated by the Environmental Protection Agency (EPA) and the Alabama Department of Environmental Management (ADEM). Almost every laboratory and many allied and support personnel at UAB use chemicals in their daily activities. It is the purpose of this manual to describe the operation of the Chemical Safety Program and to provide guidance in establishing safe work practices for the use of chemicals. This program applies to all work operations at this University where employees may be exposed to hazardous substances under normal working conditions or during an emergency. The Chemical Safety and Waste Management Manual combines both the Chemical Hygiene Plan for laboratories and the Hazard Communication Program for maintenance, environmental services, and other support personnel. The Occupational Safety and Health Administration (OSHA) Hazard Communication Standard may be found at : http://www.osha- slc.gov/OshStd_data/1910_1200.html.
    [Show full text]