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Chloroacetic Acids

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Chloroacetic Acids Chloroacetic Acids GU¨ NTER KOENIG, Hoechst Aktiengesellschaft, Augsburg, Germany ELMAR LOHMAR, Hoechst Aktiengesellschaft, Koln,€ Germany NORBERT RUPPRICH, Bundesanstalt fur€ Arbeitsschutz, Dortmund, Germany MARTIN LISON, CABB GmbH, Sulzbach, Germany ALEXANDER GNASS, CABB GmbH, Gersthofen, Germany 1. Introduction........................ 473 3.6. Derivatives......................... 481 2. Chloroacetic Acid ................... 473 3.6.1. Dichloroacetyl Chloride. ............... 481 2.1. Physical Properties .................. 473 3.6.2. Dichloroacetic Acid Esters.............. 481 2.2. Chemical Properties ................. 474 4. Trichloroacetic Acid ................. 482 2.3. Production ......................... 475 4.1. Physical Properties .................. 482 2.3.1. Hydrolysis of Trichloroethylene ...... 476 4.2. Chemical Properties ................. 482 2.3.2. Chlorination of Acetic Acid . .......... 476 4.3. Production ......................... 482 2.4. Quality Specifications................. 478 4.4. Quality Specifications................. 482 2.5. Uses .............................. 478 4.5. Uses .............................. 482 2.6. Derivatives......................... 478 4.6. Derivatives......................... 483 2.6.1. Sodium Chloroacetate . ............... 478 4.6.1. Trichloroacetyl Chloride ............... 483 2.6.2. Chloroacetyl Chloride . ............... 479 4.6.2. Trichloroacetic Acid Esters . .......... 483 2.6.3. Chloroacetic Acid Esters ............... 479 4.6.3. Trichloroacetic Acid Salts .............. 484 2.6.4. Chloroacetamide . ................... 480 5. Environmental Protection ............. 484 3. Dichloroacetic Acid .................. 480 6. Chemical Analysis ................... 485 3.1. Physical Properties .................. 480 7. Containment Materials, Storage, and 3.2. Chemical Properties ................. 480 Transportation...................... 485 3.3. Production ......................... 480 8. Economic Aspects ................... 486 3.4. Quality Specifications................. 481 9. Toxicology and Occupational Health ..... 486 3.5. Uses .............................. 481 References ......................... 488 1. Introduction acid [79-11-8] (ClCH2COOH, Mr 94.50, mono- chloroacetic acid, chloroethanoic acid) is the Chloroacetic acid and its sodium salt are the most most industrially significant [1]. It does not occur industrially and economically important of the in nature and was first discovered as a chlorina- three chlorination products of acetic acid. The tion product of acetic acid by N. LEBLANC in 1841. sections on physical and chemical properties, It was synthesized in 1857 by R. HOFFMANN, who production, quality specifications, uses, and de- chlorinated acetic acid by using sunlight to initi- rivatives are reported separately for each of these ate the reaction. Discovery of other reaction three acids, whereas those on environmental accelerators, such as phosphorus, iodine, sulfur, protection, chemical analysis, containment ma- or acetic anhydride, followed rapidly. Develop- terials, storage, transportation, and economic ment of commercial processes, based mainly on aspects are considered together. acetic acid chlorination and later on acid hydro- lysis of trichloroethylene, followed. 2. Chloroacetic Acid 2.1. Physical Properties Chlorinated acetic acids have become important intermediates in organic synthesis because of the Pure chloroacetic acid is a colorless, hygro- ease of substitution of the Cl atoms. Chloroacetic scopic, crystalline solid, which occurs in Ullmann’s Fine Chemicals Ó 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Boschstr. 12, 69469 Weinheim, Germany ISBN: 978-3-527-33477-3 / DOI: 10.1002/14356007.a06_537.pub3 474 Chloroacetic Acids Vol. 2 Table 1. Common physical data of chloroacetic acid Parameter Form abgd fp 62–63 C 55–56 C 50–51 C 43.8 C Latent heat of fusion, DHf 19.38 kJ/mol 18.63 kJ/mol 15.87 kJ/mol – 65 Density d4 1:3703 (liquid) 20 d20 1:58 (solid) 20 Refractive index nD 1:4297 Surface tension, s (100 C) 35.17 mN/m Viscosity, h 70 C 2.16 mPa s 100 C 1.32 mPa s 130 C 1.30 mPa s Degree of dissociation in water (potentiometric) (25 C) 1.52 Â 10À3 Dielectric constant (100 C) 16.8 Electrical conductivity, lowest value measured (70 C) 3.1 mS/cm* Specific heat capacity, cp Solid, 15–45 C 144.02 J molÀ1 KÀ1 Liquid, 70 C 180.45 J molÀ1 KÀ1 Liquid, 130 C 187.11 J molÀ1 KÀ1 Heat of combustion, DHc 715.9 kJ/mol Heat of evaporation, DHv 50.09 kJ/mol Heat of formation, DHf (100 C): À490.1 kJ/mol Heat of sublimation, DHsubl (25 C): 88.1 kJ/mol Heat of solution in H2O, DHsolv (16 C) Solid À14.0 kJ/mol Liquid 1.12 kJ/mol Flash point (DIN 51 758) 126 C Ignition temperature (DIN 51 794) 460 C Lower explosion limit in air (101.3 kPa) 8 vol% * Rises steeply if traces of water present. monoclinically prismatic structures existing in Chloroacetic acid has excellent solubility the a-, b-, g-, and also possibly the d-form. The in water and good solubility in methanol, a-form is the most stable and the most impor- acetone, diethyl ether, and ethanol, but is only tant industrially. sparingly soluble in hydrocarbons and chlori- Published physical data vary widely [1]. Some nated hydrocarbons. Chloroacetic acid forms of the most common values appear in Tables 1 azeotropes with a number of organic com- and 2. pounds [2]. The freezing points of various binary mixtures of chloroacetic acids are shown in Figure 1. Table 2. Vapor pressure and solubility in water of the a-form of chloroacetic acid Vapor pressure Solubility in water 2.2. Chemical Properties Temperature, Pressure, Temperature, g/100 g g/100 g The high reactivity of the carboxylic acid C kPa C solution H2O group and the ease of substitution of the a-Cl 189 101.3 0 71 245 atom are directly related. As a result, chloro- 160 40 10 76 317 acetic acid is a common synthetic organic 150 28 20 80.8 421 intermediate, either as the acid itself or as an 140 19 30 85.8 604 130 13 40 90.8 987 acid derivative (e.g., salt, ester, anhydride, acyl 100 4.3 50 95 1900 chloride, amide, hydrazide, etc.). Some impor- 90 2.6 60 99 – tant reactions that are used for industrial 80 1.1 applications are as follows. Vol. 2 Chloroacetic Acids 475 [79-14-1] (hydroxyacetic acid) and diglycolic acid [110-99-6] (2,20-oxydiacetic acid). Heating the salts gives glycolide, 1,4-diox- ine-2,5-dione [502-97-6]. Reaction with sodi- um or potassium hydrogensulfide forms thio- glycolic acid [68-11-1] and thiodiglycolic acid [123-93-3]. Reaction with ammonia gives either aminoa- cetic acid [56-40-6] (glycine) as the main product or, depending on reaction conditions, nitrilotria- cetic acid [139-13-9]. If methyl chloroacetate reacts with ammonia at low temperature, chlor- oacetamide [79-07-2] is obtained. By reaction with tertiary amines in alkaline solution various commercially important betaines are formed (e.g., N-lauryl betaine [683-10-3]). Aromatic compounds, such as naphthalene, undergo electrophilic substitution with chloroa- cetic acid over suitable catalysts to form aryla- Figure 1. Freezing points of binary mixtures cetic acids. a) Acetic acid (AA), chloroacetic acid (CAA), dichloroacetic Reaction with potassium cyanide in a neutral acid (DCA), trichloroacetic acid (TCA); b) Crystalline phase solution gives the commercially important cya- CAA; c) Crystalline phase AA noacetic acid [372-09-8], which is used as an intermediate in the production of synthetic caf- Reaction with inorganic bases, oxides, and feine [58-08-2]. Reaction with potassium iodide carbonates or with organic bases gives salts; forms iodoacetic acid [64-69-7]. some salts form adducts with chloroacetic acid. The corresponding phenoxyacetic acids, Sodium chloroacetate [3926-62-3] is an impor- some of which are of industrial importance, are tant commercial product. made by phenol etherification in the presence of Chloroacetic acid esters are obtained by reac- sodium hydroxide. Another industrially signifi- tion with alcohols or olefins; methyl chloroace- cant ether formation process gives carboxy- tate [96-34-4], ethyl chloroacetate [105-39-5], methyl derivatives with a relatively high degree and tert-butyl chloroacetate [107-59-5] are also of etherification by reacting polysaccharides, important industrially. such as cellulose, starch, guar, etc., in a strongly Chloroacetyl chloride [79-04-9] is produced alkaline sodium hydroxide medium. from the acid by reaction with POCl3, PCl3, PCl5, thionyl chloride (SOCl2), phosgene (COCl2), etc. (see Section 2.6.2). 2.3. Production Chloroacetic acid reacts with chloroacetyl chloride to form bis(chloroacetic)anhydride A multitude of methods have been proposed and [541-88-8], which can also be obtained by dehy- patented for the production of chloroacetic acid [1, 3–15]. Historically both the hydrolysis of dration of chloroacetic acid with P2O5 or by reaction of chloroacetic acid with acetic anhy- 1,1,2-trichloroethylene [79-01-6] catalyzed with dride. Chloroacetyl chloride forms mixed anhy- sulfuric acid (Eq. 1), and the catalyzed chlorina- drides with other carboxylic acids, e.g., acetic tion of acetic acid with chlorine (Eq. 2) were used chloroacetic anhydride [4015-58-1]. to produce chloroacetic acid on an industrial Nucleophilic substitution of the chlorine atom scale, however, only the latter (and older) process is an important reaction when the product is used is now used. as an intermediate in organic syntheses. For example, heating neutral or basic aqueous solu- tions hydrolyzes the chlorine atom. This is an industrial method of producing glycolic
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