DOCSLIB.ORG

United States Patent Office Patented Apr

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
United States Patent Office Patented Apr 3,576,860 United States Patent Office Patented Apr. 27, 1971 2 3,576,860 Further objects, aspects and advantages of the inven PREPARATION OF CHLOROACETYL CHLORIDE . tion will be apparent from the description which follows. Dimitri A. Zazaris, Belleville, Ill., assignor to Chlorination of acetic acid alone in the absence of a Monsanto Company, St. Louis, Mo. catalyst by prior art processes usually requires relatively No Drawing. Filed Dec. 20, 1967, Ser. No. 691,975 5 high temperatures, 110 to 120° C., in order for the re Int, C. C07c53/20 action to occur. Temperature in this range, however, re U.S. C. 260-539 9 Claims Sult in a high yield of dichloroacetic acid. In order to re duce the reaction temperature, acetic anhydride, acetyl chloride, inorganic salts or combination of the three have ABSTRACT OF THE DISCLOSURE O been added to the acetic acid. Reaction ompositions of 85 weight percent acetic anhydride and 15 weight percent Chlorination of acetic anhydride and acetic anhydride acetic acid have been utilized. In the chlorination of this acetic acid mixtures in the presence of lithium chloride to mixture, the product obtained was predominantly mono yield a mixture of monochloroacetyl chloride and mono chloroacetic acid. This is contrary to what would be ex chloroacetic acid having a small concentration of the poly pected since theoretically acetic anhydride should give 1 chlorinated derivatives. mole of acid and 1 mole of acid halide per mole of an hydride. The use of many inorganic salts did not mate rially change this result. Many of the present commercial herbicides, such as the It has previously been determined that the low yield of chloroacetamides and "2,4-D,' utilize a monochloroacetyl 20 monochloroacetyl chloride is due to the interactions of chloride or monochloroacetic acid as an intermediate. the acid chloride and any free acid, resulting in the for Inclusion of the polychlorinated acids or acid chlorides in mation of predominantly the monochloroacetic acid. the intermediate, yields a product which has decreased When acetic anhydride alone is chlorinated, the product biological activity and different physical properties which contains more chloro acids than chloro acid halides and interfere in the formulation of the herbicide. The mono 25 the concentration of dichlorinated derivatives is higher chloroacetic acid and monochloroacetyl chloride should, than when a mixture with acetic acid is chlorinated. These therefore, have a minimum of the polychlorinated deriva side reactions are disadvantageous if the product desired tives, which should not exceed about 2%, in order to is the acid halide. obtain maximum biological activity and ease of formula It has now been found that the introduction of lithium tion. 30 chloride alone or in combination with hydrogen chlo Separation of the monochloro acids and acid chlorides ride to a reaction mixture containing 0 to about 17 per from the polychlorinated derivatives by conventional cent of acetic acid and about 83 to 100 percent of ace means is an expensive and difficult operation due to the tic anhydride yields a mixture of monochloroacetic acid close similarities in physical properties. As an alternate, and monochloroacetyl chloride, which contains less than the preparation of monochloroacetic acid and acid chlo 35 1.5 percent of the dichloro derivative in the acid halide, rides was modified to decrease the amount of the poly in a weight ratio which approaches theory (1.19 for ace chlorinated derivatives formed to an acceptable level. tic anhydride and 0.89 for the 83/17 mixture). In the prior art, acetic anhydride and/or acetyl chlo In the chlorination of acetic anhydride or acetic acid ride have been added to catalyze the chlorination of acetic acetic anhydride mixtures, it is generally held that many acid and partially suppresses the formation of the poly 40 different reactions are occurring simultaneously, but not chlorinated derivatives. The chlorination of acetic anhy in the same degree or rate, among which are: dride alone results in the formation of a large concentra tion (9 to 11%) of the polychlorinated derivatives. The (1) CHCsoO -- Cl2 --> Cicirc-soO addition of inorganic salts also only partially suppresses / M the formation of the polychlorinated derivatives, even in 45 CH3C=O CH3CO the presence of acetic anhydride. These modifications of the chlorination reaction do not reduce the concentration of polychlorinated derivatives to -- CHit-Cl -- CCH3COOH an acceptable level unless the reaction is stopped when CH3C=O O only approximately 80 to 85% of the acetic acid-acetic anhydride has been converted. This requires the separa (2) o -- HCl -- CH3COOH -- OH, -ci tion and recycling of a large amount of unreacted start CH3C=O ing material. 2 o It is, therefore, an object of this invention to provide a O O ClCH2C novel synthetic process for the preparation of monochlo 55 N HCl roacetic acid and monochloroacetyl chloride which elimi (3) CH3C-OH -- ClCH2C Cl-) yo - nates the above disadvantages. CH3C=O It is another object of this invention to provide a proc ClCHCOOH ess for preparing monochloroacetic acid and monochloro -- acetyl chloride having less than 4.0 and 1.5 weight per 60 cent of dichloroacetic acid or dichloroacetyl chloride in CH,8-ci the acid and acid chloride fractions, respectively. It is a further object of this invention to provide a proc g ess for preparing monochloroacetic acid and the mono (4) CH3C Cl -- Cl2 ---> ClCHCCl chloroacetyl chloride in which at least 95% of the start 65 O O O ing compound is converted to the desired monochloro derivative. (5) ClCH2C-Cl -- CH3COOH -- ClCH2COH -- CHC-Cl It is a still further object of this invention to provide (6) CH3COOH + Cl2 - ClCH2COOH -- HCl a process for the preparation of monochloroacetic acid As can be seen from Reactions 1, 3 and 5, the forma and monochloroacetyl chloride from acetic anhydride in 70 tion of monochloroacetic acid is favored over the forma which the weight ratio of monochloroacetyl chloride to tion of monochloroacetyl chloride, and thus more acid monochloroacetic acid approaches the theoretical 119:100. is formed than acid halide. 3,576,860 3 4 In accordance with the present invention, the chloride In a suitable vessel, equipped with a temperature ion probably interacts with the monochloric anhydride measuring means, a reflux condenser, an off-gas outlet (Equations 1 and 3) to give the products monochloroacetyl fitted with a reflux condenser, and a chlorine sparger con chloride and acetic acid. The formation of the acid halide nected to a gas measuring means, was added the acetic is thus favored and the acid halide/acid weight ratio ap anhydride or acetic anhydride-acetic acid mixture and proaches theory. the required amount of lithium chloride, and the batch In the prior art, chlorination reactions were terminated heated to about 90° C. Chlorine was introduced into the after about 80 to 85% of the reaction mixture was con mixture at a slow rate for the first 1/2 hours. During this verted to the chlorinated product in order to reduce the induction period, only small amounts of chlorine were quantity of dichlorinated compounds. The unreacted acid absorbed and the reaction mixture attained the typical or anhydride thus had to be separated from the reaction l O yellowish-green coloration of chlorine. After the reac medium. In the present invention, chlorination of the tion was initiated, the coloration disappeared and the reaction composition to a conversion of at least 95% is chlorine was absorbed as it was added. The chlorine rate possible without any material increase in dichloro forma was increased and adjusted to provide a reaction time of tion. In actual practice, quantitative conversions have 5 about 8 to 9 hours. The temperature was controlled with been obtained. in the approximate range of 80 to 90° C. during the Reaction temperature for the procedure of the present reaction time. Chlorine addition was discontinued when invention is in the approximate range of 70 to 100° C., the off-gas attained the chlorine coloration. The specific with the preferred temperature range being about 80 to gravity of the mixture at this period was approximately 90° C. Temperatures outside this range can be utilized 20 1.3607 at 75° C. but lead to an increase in dichlorinated derivatives at the The results obtained from this procedure using various higher temperature and longer reaction times and increase mixtures of acetic anhydride and acetic acid and various in dichlorinated products at lower temperatures. amounts of lithium chloride is reported in Table I. Chlorine is initially introduced into the reaction mix It will be noted that in some runs hydrogen chloride ture, during the induction period, at a relatively slow rate. 25 is added as a co-catalyst. The use of hydrogen chloride re During this period of the reaction, the mixture attains the duces the induction time from about 1/2 hours to about coloration of chlorine. After the reaction has started, this 15 minutes. Hydrogen chloride, when utilized, is added to coloration will disappear. The chlorine rate is then in the reaction mixture prior to the chlorine addition. Hy creased and adjusted to a rate that will provide complete drogen chloride is added to the reaction medium in an chlorination in about 8 to 9 hours. Completion of chlori 30 amount up to about 15 percent by weight of the reaction nation is evidenced by the presence of free chlorine in medium with the optimum amount being about 5 to 10 the off gas. percent. The procedure with hydrogen chloride is as provi The amount of lithium chloride added to the reaction ously described with the exception that the induction mixture is in the range of about 0.1 to 2.5 percent by period is reduced to about 15 minutes.
Load more

Recommended publications
  • APPENDIX G Acid Dissociation Constants
    harxxxxx_App-G.qxd 3/8/10 1:34 PM Page AP11 APPENDIX G Acid Dissociation Constants §␮ ϭ 0.1 M 0 ؍ (Ionic strength (␮ † ‡ † Name Structure* pKa Ka pKa ϫ Ϫ5 Acetic acid CH3CO2H 4.756 1.75 10 4.56 (ethanoic acid) N ϩ H3 ϫ Ϫ3 Alanine CHCH3 2.344 (CO2H) 4.53 10 2.33 ϫ Ϫ10 9.868 (NH3) 1.36 10 9.71 CO2H ϩ Ϫ5 Aminobenzene NH3 4.601 2.51 ϫ 10 4.64 (aniline) ϪO SNϩ Ϫ4 4-Aminobenzenesulfonic acid 3 H3 3.232 5.86 ϫ 10 3.01 (sulfanilic acid) ϩ NH3 ϫ Ϫ3 2-Aminobenzoic acid 2.08 (CO2H) 8.3 10 2.01 ϫ Ϫ5 (anthranilic acid) 4.96 (NH3) 1.10 10 4.78 CO2H ϩ 2-Aminoethanethiol HSCH2CH2NH3 —— 8.21 (SH) (2-mercaptoethylamine) —— 10.73 (NH3) ϩ ϫ Ϫ10 2-Aminoethanol HOCH2CH2NH3 9.498 3.18 10 9.52 (ethanolamine) O H ϫ Ϫ5 4.70 (NH3) (20°) 2.0 10 4.74 2-Aminophenol Ϫ 9.97 (OH) (20°) 1.05 ϫ 10 10 9.87 ϩ NH3 ϩ ϫ Ϫ10 Ammonia NH4 9.245 5.69 10 9.26 N ϩ H3 N ϩ H2 ϫ Ϫ2 1.823 (CO2H) 1.50 10 2.03 CHCH CH CH NHC ϫ Ϫ9 Arginine 2 2 2 8.991 (NH3) 1.02 10 9.00 NH —— (NH2) —— (12.1) CO2H 2 O Ϫ 2.24 5.8 ϫ 10 3 2.15 Ϫ Arsenic acid HO As OH 6.96 1.10 ϫ 10 7 6.65 Ϫ (hydrogen arsenate) (11.50) 3.2 ϫ 10 12 (11.18) OH ϫ Ϫ10 Arsenious acid As(OH)3 9.29 5.1 10 9.14 (hydrogen arsenite) N ϩ O H3 Asparagine CHCH2CNH2 —— —— 2.16 (CO2H) —— —— 8.73 (NH3) CO2H *Each acid is written in its protonated form.
    [Show full text]
  • Safety Data Sheet
    SAFETY DATA SHEET Creation Date 15-Feb-2011 Revision Date 10-Dec-2020 Revision Number 7 SECTION 1: IDENTIFICATION OF THE SUBSTANCE/MIXTURE AND OF THE COMPANY/UNDERTAKING 1.1. Product identifier Product Description: Chloroacetic acid Cat No. : 108510000; 108510010; 108510025; 108510040; 108512500 Synonyms MCA CAS-No 79-11-8 EC-No. 201-178-4 Molecular Formula C2 H3 Cl O2 Reach Registration Number 01-2119459589-18 1.2. Relevant identified uses of the substance or mixture and uses advised against Recommended Use Laboratory chemicals. Sector of use SU3 - Industrial uses: Uses of substances as such or in preparations at industrial sites Product category PC21 - Laboratory chemicals Process categories PROC15 - Use as a laboratory reagent Environmental release category ERC6a - Industrial use resulting in manufacture of another substance (use of intermediates) Uses advised against No Information available 1.3. Details of the supplier of the safety data sheet Company UK entity/business name Fisher Scientific UK Bishop Meadow Road, Loughborough, Leicestershire LE11 5RG, United Kingdom EU entity/business name Acros Organics BVBA Janssen Pharmaceuticalaan 3a 2440 Geel, Belgium E-mail address [email protected] 1.4. Emergency telephone number For information US call: 001-800-ACROS-01 / Europe call: +32 14 57 52 11 Emergency Number US:001-201-796-7100 / Europe: +32 14 57 52 99 CHEMTREC Tel. No.US:001-800-424-9300 / Europe:001-703-527-3887 SECTION 2: HAZARDS IDENTIFICATION 2.1. Classification of the substance or mixture CLP Classification
    [Show full text]
  • Safety Data Sheet MCAA
    SAFETY DATA SHEET MONOCHLOROACETIC ACID 80% - 90% AQ Solution Revision Date: September 2019 Previous date: May 2014 Print Date: September 2019 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE AND OF THE COMPANY/UNDERTAKING 1.1 Product information Commercial Product Name Monochloroacetic Acid Chemical Formula CICH2CO2H Molecular wt. 94.50 80-90% Solution 1.2 Relevant identified uses of the substance or mixture and uses advised against Use of the Substance/Mixture Recommended restrictions on use Reserved for industrial and professional use. 1.3 Details of the supplier of the safety data sheet Niacet Corporation 400 47th Street Niagara Falls, NY 14304 U.S.A. Telephone +1 716-285-1474 Telefax +1 716-285-1497 [email protected] 1.4 Emergency telephone number For Niacet Corporation, Niagara Falls, U.S.A. products: Chemtrec: +1 (800) 424 9300, +1 (703) 527-3887 2. HAZARDS IDENTIFICATION 2.1 Classification of the substance or mixture Classification according to OSHA Hazards Target Organ Effect (Central Nervous System, Heart, Skeletal Muscle, Kidney), Toxic by ingestion, Toxic by skin absorption, Corrosive Rapidly absorbed through skin Classification according to GHS Classification Acute toxicity, Oral (Category 3) Acute toxicity, Inhalation (Category 3) Skin corrosion (Category 1B) Serious eye damage (Category 1) 1/12 SAFETY DATA SHEET MONOCHLOROACETIC ACID 80% - 90% AQ Solution Revision Date: September 2019 Previous date: May 2014 Print Date: September 2019 Acute aquatic toxicity (Category 1) 2.2 Label elements Labeling according to GHS Label elements, including precautionary statements Pictogram Signal word Danger Hazard statement(s) H301 + H311 Toxic if swallowed or in contact with skin H314 Causes severe skin burns and eye damage.
    [Show full text]
  • Chloroacetic Acid ≥99,5 %, P.A
    Safety data sheet according to Regulation (EC) No. 1907/2006 (REACH) Chloroacetic acid ≥99,5 %, p.a. article number: 9849 date of compilation: 2016-06-17 Version: 1.1 en Revision: 2021-02-17 Replaces version of: 2016-06-17 Version: (1) SECTION 1: Identification of the substance/mixture and of the company/ undertaking 1.1 Product identifier Identification of the substance Chloroacetic acid ≥99,5 %, p.a. Article number 9849 Registration number (REACH) It is not required to list the identified uses be- cause the substance is not subject to registration according to REACH (< 1 t/a). Index number in CLP Annex VI 607-003-00-1 EC number 201-178-4 CAS number 79-11-8 1.2 Relevant identified uses of the substance or mixture and uses advised against Relevant identified uses: Laboratory chemical Laboratory and analytical use Uses advised against: Do not use for squirting or spraying. Do not use for products which come into direct contact with the skin. Do not use for products which come in- to contact with foodstuffs. Do not use for private purposes (household). 1.3 Details of the supplier of the safety data sheet Carl Roth GmbH + Co KG Schoemperlenstr. 3-5 D-76185 Karlsruhe Germany Telephone:+49 (0) 721 - 56 06 0 Telefax: +49 (0) 721 - 56 06 149 e-mail: [email protected] Website: www.carlroth.de Competent person responsible for the safety data :Department Health, Safety and Environment sheet: e-mail (competent person): [email protected] 1.4 Emergency telephone number Name Street Postal Telephone Website code/city National Poisons Information Beaumont Road Dublin 9 01 809 2166 https:// Centre www.poisons.ie/ Beaumont Hospital Ireland (en) Page 1 / 17 Safety data sheet according to Regulation (EC) No.
    [Show full text]
  • Study on Gas-Phase Mechanism of Chloroacetic Acid Synthesis by Catalysis and Chlorination of Acetic Acid
    Asian Journal of Chemistry; Vol. 26, No. 2 (2014), 475-480 http://dx.doi.org/10.14233/ajchem.2014.15484 Study on Gas-Phase Mechanism of Chloroacetic Acid Synthesis by Catalysis and Chlorination of Acetic Acid * JIAN-WEI XUE , JIAN-PENG ZHANG, BO WU, FU-XIANG LI and ZHI-PING LV Research Institute of Special Chemicals, Taiyuan University of Technology, Taiyuan 030024, Shanxi Province, P.R. China *Corresponding author: Fax: +86 351 6111178; Tel: +86 351 60105503; E-mail: [email protected] Received: 14 March 2013; Accepted: 17 May 2013; Published online: 15 January 2014; AJC-14570 The process of acetic acid catalysis and chlorination for synthesizing chloroacetic acid can exist in not only gas phase but also liquid phase. In this paper, the gas-phase reaction mechanism of the synthesis of chloroacetic acid was studied. Due to the high concentration of acetic acid and the better reaction mass transfer in the liquid-phase reaction, the generation amount of the dichloroacetic acid was higher than that in the gas-phase reaction. Under the solution distillation, the concentration of acetyl chloride, whose boiling point is very low, was very high in the gas phase, sometimes even up to 99 %, which would cause the acetyl chloride to escape rapidly with the hydrogen chloride exhaust, so that the reaction slowed down. Therefore, series reactions occured easily in the gas-phase reaction causing the amount of the dichloroacetic acid to increase. Keywords: Gas phase, Catalysis, Chlorination, Chloroacetic acid, Acetic acid. INTRODUCTION Martikainen et al.3 summed up the reaction mechanism that was consistent with a mechanism found by Sioli according Chloroacetic acid is not only a fine chemical product but to the system condition experiment and systematic theoretical also an important intermediate in organic synthesis.
    [Show full text]
  • Safety Data Sheet (SDS) OSHA Hazcom Standard 29 CFR 1910.1200(G) and GHS Rev 03
    Page 1/12 Safety Data Sheet (SDS) OSHA HazCom Standard 29 CFR 1910.1200(g) and GHS Rev 03. Reviewed on 09/25/18 Issue date 06/11/15 * 1 Identification ꞏ Product identifier ꞏ Trade name: Monochloroacetic Acid Solution ꞏ Relevant identified uses of the substance or mixture and uses advised against No further relevant information available. ꞏ Product description Monochloroacetic Acid Solution ꞏ Details of the supplier of the safety data sheet ꞏ Manufacturer/Supplier: Dermatologic Lab & Supply, Inc. 608 13th Ave. Council Bluffs, IA USA 51501-6401 Voice: (800) 831-6273 or (712) 323-3269 Fax: (800) 320-9612 or (712) 323-1156 www.delasco.com ꞏ Emergency telephone number: Chemtrec 800-424-9300 * 2 Hazard(s) identification ꞏ Classification of the substance or mixture GHS06 Skull and crossbones Acute Tox. 3 H311 Toxic in contact with skin. Acute Tox. 3 H331 Toxic if inhaled. GHS05 Corrosion Skin Corr. 1B H314 Causes severe skin burns and eye damage. Eye Dam. 1 H318 Causes serious eye damage. GHS09 Environment Aquatic Acute 1H400Very toxic to aquatic life. GHS07 Acute Tox. 4 H302Harmful if swallowed. Label elements ꞏ 41.0 Page 2/12 Safety Data Sheet (SDS) OSHA HazCom Standard 29 CFR 1910.1200(g) and GHS Rev 03. Issue date 06/11/15 Reviewed on 09/25/18 Trade name: Monochloroacetic Acid Solution ꞏ GHS label elements The product is classified and labeled according to the Globally Harmonized System (GHS). ꞏ Hazard pictograms GHS05 GHS06 GHS09 ꞏ Signal word Danger ꞏ Hazard-determining components of labeling: Chloroacetic acid ꞏ Hazard statements Harmful if swallowed.
    [Show full text]
  • Dissociation Constants of Organic Acids and Bases
    DISSOCIATION CONSTANTS OF ORGANIC ACIDS AND BASES This table lists the dissociation (ionization) constants of over pKa + pKb = pKwater = 14.00 (at 25°C) 1070 organic acids, bases, and amphoteric compounds. All data apply to dilute aqueous solutions and are presented as values of Compounds are listed by molecular formula in Hill order. pKa, which is defined as the negative of the logarithm of the equi- librium constant K for the reaction a References HA H+ + A- 1. Perrin, D. D., Dissociation Constants of Organic Bases in Aqueous i.e., Solution, Butterworths, London, 1965; Supplement, 1972. 2. Serjeant, E. P., and Dempsey, B., Ionization Constants of Organic Acids + - Ka = [H ][A ]/[HA] in Aqueous Solution, Pergamon, Oxford, 1979. 3. Albert, A., “Ionization Constants of Heterocyclic Substances”, in where [H+], etc. represent the concentrations of the respective Katritzky, A. R., Ed., Physical Methods in Heterocyclic Chemistry, - species in mol/L. It follows that pKa = pH + log[HA] – log[A ], so Academic Press, New York, 1963. 4. Sober, H.A., Ed., CRC Handbook of Biochemistry, CRC Press, Boca that a solution with 50% dissociation has pH equal to the pKa of the acid. Raton, FL, 1968. 5. Perrin, D. D., Dempsey, B., and Serjeant, E. P., pK Prediction for Data for bases are presented as pK values for the conjugate acid, a a Organic Acids and Bases, Chapman and Hall, London, 1981. i.e., for the reaction 6. Albert, A., and Serjeant, E. P., The Determination of Ionization + + Constants, Third Edition, Chapman and Hall, London, 1984. BH H + B 7. Budavari, S., Ed., The Merck Index, Twelth Edition, Merck & Co., Whitehouse Station, NJ, 1996.
    [Show full text]
  • Chloroacetic Acid
    Chloroacetic Acid 79-11-8 Hazard Summary Exposure to chloroacetic acid is most likely to occur in the workplace. Acute (short-term) inhalation or dermal exposure may irritate or cause severe damage to the skin, eyes, respiratory tract, and mucous membranes and cause depression of the central nervous system in humans. No information is available on the chronic (long-term) effects of chloroacetic acid in humans. Damage to the respiratory tract has been observed in rodents chronically exposed to chloroacetic acid by inhalation, orally, and via gavage (experimentally placing the chemical in the stomach). EPA has not classified chloroacetic acid for potential carcinogenicity. Please Note: The main source of information for this fact sheet is EPA's Health and Environmental Effects Document for Chloroacetic Acid (2). Other secondary sources include the Hazardous Substances Data Bank (HSDB) (3), a database of summaries of peer-reviewed literature, and the Registry of Toxic Effects of Chemical Substances (RTECS) (6), a database of toxic effects that are not peer reviewed. Uses Chloroacetic acid is used in the manufacture of cellulose ethers (used mainly for drilling muds, detergents, food, and pharmaceuticals), as a post-emergence contact herbicide and defoliant, and in the manufacture of glycine and thioglycolic acid. (2) Chloroacetic acid is also used in the manufacture of various dyes, synthetic caffeine, and organic chemicals. (1,4) Sources and Potential Exposure Individuals are most likely to be exposed to chloroacetic acid in the workplace. (1) Chloroacetic acid may be released to the environment during its production and use. (2) Assessing Personal Exposure No information was located regarding the measurement of personal exposure to chloroacetic acid.
    [Show full text]
  • Chloroacetic Acid 100% Technical, Flakes
    CHLOROACETIC ACID 100% TECHNICAL, FLAKES TECHNICAL PRODUCT SPECIFICATION NUMBER MCAA/008/01 DATE 07.12.2017 CHEMICAL NAME Monochloroacetic acid 100% TECHNICAL REQUIREMENTS Appearance at 20-25°C.......Solid flakes, white to slightly yellowish (visual method) MCAA [% (w/w)] .................................................................... ≥ 99.0 (PB.32 – HPLC-UV ) DCAA [% (w/w)] ................................................................ max. 0.15 (PB.32 – HPLC-UV ) Acetic acid [% (w/w)] .......................................................... max. 0.2 (PB.32 – HPLC-UV ) Water [% (w/w)] .................................................................. max. 0.2 (PB.06 Karl Fischer Titration) Iron [mg/kg] ............................................................................ max. 5 (PB.18 – ICP-OES) Lead [mg/kg] .......................................................................... max. 1 (PB.18 – ICP-OES) INFORMATIVE DATA* Formula........................................................ H3C2O2Cl, CH2ClCO2H Molar mass ................................................................................ 94.5 Melting point [°C] .......................................................................... 63 Boiling point [°C] ......................................................................... 189 Biodegradability ..............................................readily biodegradable * These informative data are not technical requirements and cannot form the basis for any claims. USE MCAA is a bifunctional moiety, having both
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 6,326,514 B1 Klug Et Al
    USOO632651.4B1 (12) United States Patent (10) Patent No.: US 6,326,514 B1 Klug et al. (45) Date of Patent: Dec. 4, 2001 (54) PROCESS FOR THE PREPARATION OF 5,233,087 * 8/1993 Cripe. ETHER CARBOXYLIC ACIDS WITH LOW 5,420,315 * 5/1995 Uhrig et al. RESIDUAL ALCOHOL CONTENT 5,523,479 * 6/1996 Sanders et al. FOREIGN PATENT DOCUMENTS (75) Inventors: Peter Klug, Grossostheim; Rainer Kupfer, Hattersheim; Ignaz Wimmer, O 166958 1/1986 (EP). Winhöring; Ridiger Winter, Frankfurt, O 295-578 12/1988 (EP). all of (DE) OTHER PUBLICATIONS (73) Assignee: Clariant GmbH, Frankfurt (DE) EPO Search Report. Derwent Patent Family Abstract for EP 0 166958. (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 * cited by examiner U.S.C. 154(b) by 0 days. Primary Examiner Johann Richter Assistant Examiner Sikarl A. Winterspoon (21) Appl. No.: 09/596,418 (74) Attorney, Agent, or Firm-Susan S. Jackson; Scott E. Hanf (22) Filed: Jun. 19, 2000 (57) ABSTRACT (30) Foreign Application Priority Data The invention provides a process for the preparation of ether Jun. 19, 1999 (DE) .............................................. 19928 128 carboxylic acids or alkali metal or ammonium Salts thereof (51) Int. Cl." ...................... C07C 59/125; CO7C 59/305; with low residual alcohol content, which comprises firstly CO7C 59/58 converting a mono- or polyhydric alcohol into the corre (52) U.S. Cl. ........................... 562/583; 562/588; 568/620 sponding alkoxide using a SubStoichiometric amount (58) Field of Search ..................................... 562/583,588; between 5 and 95 mol % of a basic compound, and then 554/124; 568/620 reacting the alkoxide with alkylene oxides, and, if necessary after distilling off the residual alcohol which remains, alky (56) References Cited lating the highly alkaline reaction mixture, which comprises more than 5 mol % of alkoxylated alkoxides, directly with U.S.
    [Show full text]
  • COUMARONE [Benzofuran]
    A Publication of Reliable Methods for the Preparation of Organic Compounds Working with Hazardous Chemicals The procedures in Organic Syntheses are intended for use only by persons with proper training in experimental organic chemistry. All hazardous materials should be handled using the standard procedures for work with chemicals described in references such as "Prudent Practices in the Laboratory" (The National Academies Press, Washington, D.C., 2011; the full text can be accessed free of charge at http://www.nap.edu/catalog.php?record_id=12654). All chemical waste should be disposed of in accordance with local regulations. For general guidelines for the management of chemical waste, see Chapter 8 of Prudent Practices. In some articles in Organic Syntheses, chemical-specific hazards are highlighted in red “Caution Notes” within a procedure. It is important to recognize that the absence of a caution note does not imply that no significant hazards are associated with the chemicals involved in that procedure. Prior to performing a reaction, a thorough risk assessment should be carried out that includes a review of the potential hazards associated with each chemical and experimental operation on the scale that is planned for the procedure. Guidelines for carrying out a risk assessment and for analyzing the hazards associated with chemicals can be found in Chapter 4 of Prudent Practices. The procedures described in Organic Syntheses are provided as published and are conducted at one's own risk. Organic Syntheses, Inc., its Editors, and its Board of Directors do not warrant or guarantee the safety of individuals using these procedures and hereby disclaim any liability for any injuries or damages claimed to have resulted from or related in any way to the procedures herein.
    [Show full text]
  • Chloroacetyl Chloride
    Chloroacetyl chloride sc-239516 Material Safety Data Sheet Hazard Alert Code Key: EXTREME HIGH MODERATE LOW Section 1 - CHEMICAL PRODUCT AND COMPANY IDENTIFICATION PRODUCT NAME Chloroacetyl chloride STATEMENT OF HAZARDOUS NATURE CONSIDERED A HAZARDOUS SUBSTANCE ACCORDING TO OSHA 29 CFR 1910.1200. NFPA FLAMMABILITY0 HEALTH3 HAZARD INSTABILITY1 SUPPLIER Company: Santa Cruz Biotechnology, Inc. Address: 2145 Delaware Ave Santa Cruz, CA 95060 Telephone: 800.457.3801 or 831.457.3800 Emergency Tel: CHEMWATCH: From within the US and Canada: 877-715-9305 Emergency Tel: From outside the US and Canada: +800 2436 2255 (1-800-CHEMCALL) or call +613 9573 3112 PRODUCT USE Preparation of chloroacetophenone; intermediate; tear gas. SYNONYMS C2-H2-Cl2-O, ClCH2COCl, "acetyl chloride, chloro-", "chloroacetic acid chloride", "chloroacetic chloride", "monochloroacetyl chloride" Section 2 - HAZARDS IDENTIFICATION CANADIAN WHMIS SYMBOLS EMERGENCY OVERVIEW RISK Reacts violently with water. Causes severe burns. Risk of serious damage to eyes. Toxic: danger of serious damage to health by prolonged exposure through inhalation. Toxic by inhalation, in contact with skin and if swallowed. 1 of 20 Very toxic to aquatic organisms. POTENTIAL HEALTH EFFECTS ACUTE HEALTH EFFECTS SWALLOWED • The material can produce severe chemical burns within the oral cavity and gastrointestinal tract following ingestion. • Toxic effects may result from the accidental ingestion of the material; animal experiments indicate that ingestion of less than 40 gram may be fatal or may produce serious damage to the health of the individual. • Ingestion of acidic corrosives may produce burns around and in the mouth. the throat and esophagus. Immediate pain and difficulties in swallowing and speaking may also be evident.
    [Show full text]