| HS Code | 690077 |
| Product Name | Chloroacetic Acid |
| Chemical Formula | C2H3ClO2 |
| Molecular Weight | 94.50 g/mol |
| Cas Registry Number | 79-11-8 |
| Einecs Number | 201-178-4 |
| Appearance | Colorless to white crystalline solid |
| Odor | Pungent, vinegar-like |
| Melting Point | 61-63 °C |
| Boiling Point | 189 °C |
| Density | 1.58 g/cm³ at 20 °C |
| Solubility In Water | Approximately 858 g/L at 25 °C |
| Solubility In Organic Solvents | Soluble in ethanol, ether, chloroform, benzene |
| Pka | 2.87 at 25 °C |
| Vapor Pressure | 0.02 mmHg at 20 °C |
| Flash Point | 126 °C (closed cup) |
| Decomposition Temperature | Decomposes above 190 °C |
| Corrosivity | Corrosive to skin, eyes, and metals |
| Acute Oral Toxicity | LD50 rat 76 mg/kg |
| Logp | 0.22 |
| Ph | Strongly acidic in aqueous solution |
As an accredited Chloroacetic Acid factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | Chloroacetic acid packaged in 25 kg net polyethylene-lined fiber drums, sealed and labeled corrosive, with UN 1751, Class 8 markings. |
| Container Loading (20′ FCL) | Chloroacetic Acid loaded in a 20-foot FCL container: palletized drums, securely braced, with compliant hazardous-material placards and proper shipping documentation. |
| Shipping | Chloroacetic acid ships as a regulated toxic-corrosive substance, typically UN 1751 (solid) or UN 1750 (solution), Class 6.1 with Class 8 subsidiary risk. Use UN-approved, corrosion-resistant packaging, correct labels/placards, shipping papers, and trained personnel. Store cool, dry, and segregated from bases, oxidizers, and reactive metals. DOT/IMDG/IATA rules apply. |
| Storage | Store chloroacetic acid in a cool, dry, well-ventilated, secure area away from heat, direct sunlight, moisture, and incompatible materials such as bases, oxidizers, active metals, and foodstuffs. Keep containers tightly closed, clearly labeled, and upright in a corrosion-resistant cabinet with secondary containment. Use appropriate PPE and follow local regulations; prevent dust generation and spills. |
| Shelf Life | Chloroacetic acid typically has a shelf life of several years when stored sealed, cool, dry, and away from moisture, heat, and incompatible materials. |
The sodium chloroacetate charge in continuous carboxymethylation is adjusted against anhydroglucose unit (AGU) molar input across a 0.60–1.20 mol/mol range, producing a final degree of substitution between 0.65 and 1.20 depending on viscosity and clarity targets. Cellulose is first mercerized in a horizontal sigma-blade kneader with 35–50 wt% aqueous sodium hydroxide at 30–45°C for 45–90 min; the alkali cellulose is then etherified with an aqueous 40–60 wt% chloroacetic acid solution at 60–75°C for 2–3 h. The NaOH-to-chloroacetic acid molar ratio is maintained at 2.0–2.2:1 to neutralize the liberated carboxylic acid and suppress glycolic acid side reactions. In food-grade material, the addition level in frozen dairy systems is 0.2–0.4 wt% of total mix; in toothpaste binder systems, 0.5–1.5 wt%; in immediate-release tablets as a granulation binder, 2–6% w/w. For API drilling fluid-grade material, low-viscosity CMC or polyanionic cellulose is added at 0.5–3.0 lb/bbl to reduce filtrate loss to below 10 mL/30 min under API 13B-1 high-temperature filtration conditions. Terminal product types include frozen desserts, bakery films, toothpaste binders, pharmaceutical tablet granulations, and water-based drilling fluids. In acid media below pH 3.0, CMC loses viscosity and can precipitate; in high-hardness brines, multivalent cations above 100 mg/L Ca²⁺ reduce hydration efficiency unless the polymer is pre-solvated or converted to polyanionic CMC. Compliance for food-grade CMC is anchored to Commission Regulation (EU) No 231/2012 for E 466, the JECFA monograph, the USP/NF Sodium Carboxymethylcellulose monograph, and 21 CFR 182.1745; drilling-grade material is tested against API Specification 13A and API Recommended Practice 13B-1.
Between chlorination and final esterification, the phenoxyacetic acid condensation stage consumes chloroacetic acid as the carboxylate alkylating agent; this step is distinct from chlorophenol production and from subsequent formulation blending. In a typical 5,000–20,000 L glass-lined batch reactor, molten or dissolved 2,4-dichlorophenol is reacted with sodium chloroacetate generated in situ from chloroacetic acid and sodium hydroxide, with pH controlled at 9.0–10.0 and temperature held at 90–105°C. The charge mole ratio of chloroacetic acid to 2,4-dichlorophenol is retained at 1.02–1.08:1; ratios below 1.02:1 increase residual unreacted chlorophenol above 0.3% w/w in the crude acid cake, while ratios above 1.08:1 raise sodium glycolate and diglycolic acid impurities that depress technical acid purity below 95%. The condensation mass is then cooled to 60–70°C, acidified with 30–32% hydrochloric acid to pH 1.5–2.0, and filtered; the wet cake is washed with chilled water at 5–15°C to reduce chloride carry-over. Technical-grade 2,4-D acid is subsequently converted into dimethylamine salt by reaction with 40–60% aqueous dimethylamine at 50–70°C, or into 2-ethylhexyl ester by acid-catalyzed esterification with 2-ethylhexanol at 110–130°C under azeotropic water removal. Downstream formulated products include 480 g/L dimethylamine salt soluble concentrates, 960 g ae/L 2-ethylhexyl ester emulsifiable concentrates, and granular or tablet formulations for aquatic and pasture use. The active substance and formulations are evaluated under EU Regulation (EC) No 1107/2009, Commission Implementing Regulation (EU) No 540/2011, and 40 CFR 180.142. The major operational boundary is pH: below pH 8.5 the reaction rate drops sharply, while above pH 10.5 chloroacetic acid hydrolysis to sodium glycolate becomes the dominant side reaction, reducing yield to below 85% of theoretical esterification basis.
The reaction of chloroacetic acid with sodium hydrosulfide or sodium polysulfide proceeds through a bimolecular nucleophilic substitution pathway in which thiol sulfur displaces chloride; this route is performed in glass-lined or 316L stainless steel agitated vessels because of the corrosive chloride-rich liquor. In a typical high-yield process, 80% chloroacetic acid solution is added dropwise to 15–20% sodium hydrosulfide solution at 70–90°C while the reaction pH is maintained between 8.0 and 9.5; the molar input of sodium hydrosulfide to chloroacetic acid is 1.03–1.08:1. At pH below 7.5, hydrogen sulfide gas formation increases sharply; at pH above 10.0, thiodiglycolic acid and dithiodiglycolic acid byproducts rise above 2.0% w/w. Crude thioglycolic acid is released by acidification to pH 1.0–2.0, extracted with methyl ethyl ketone or ethyl acetate, and purified by vacuum distillation at 70–90°C under 5–20 mbar absolute pressure. The distilled acid or its 2-ethylhexyl ester is then reacted with organotin intermediates to produce methyltin, butyltin, or octyltin mercaptide heat stabilizers. In rigid PVC extrusion and injection molding, the mercaptide stabilizer is typically metered at 0.8–2.5 phr, with 1.0–1.5 phr common for twin-screw extrusion of pipe with L/D ratio 30–40 and melt temperature 185–205°C. Below 0.8 phr, early color formation during dynamic heat stability testing approximating DIN 53381 or ISO 182-3 appears within 10–15 min; above 2.5 phr, plate-out and die lip build-up increase without proportional thermal stability gains. Terminal product types include rigid PVC pipes tested under ISO 1452-1, PVC window profiles under EN 12608, leather unhairing and liming auxiliaries, and thioglycolate hair-wave products regulated under Annex III of Regulation (EC) No 1223/2009. Iron contamination above 2 mg/kg in the mercaptide or ester imparts a pink discoloration to clear PVC, while exposure to strong oxidizers must be excluded because of exothermic decomposition of the thiol group.
In surfactant batch reactors, the quaternization of cocamidopropyl dimethylamine with sodium chloroacetate is terminated when residual tertiary amine falls below 1.0% w/w and residual sodium chloroacetate is below 10 mg/kg in the 28–35% active matter product. The charging ratio is set at 1.02–1.08 mol sodium chloroacetate per mole of tertiary amine, with the reaction mass held at 70–85°C and pH 7.5–8.5 for 6–10 h under nitrogen blanketing; the pH is initially adjusted with 30% sodium hydroxide and later corrected with citric acid or lactic acid after quaternization. Because chloroacetic acid is corrosive in aqueous solution, the reactor and condenser are specified in 316L stainless steel or glass-lined construction, and the cooling loop must handle a reaction exotherm of approximately 80–120 kJ/mol amine without exceeding 85°C; above this temperature, amine oxide and amide hydrolysis impurities increase, shifting color to more than 150 Hazen. In finished rinse-off personal-care formulations, cocamidopropyl betaine is added at 2–12% w/w as supplied at 30% active matter; final formulation pH is adjusted to 4.5–5.5 with citric acid, and viscosity is modified with 0.5–1.5% sodium chloride. Terminal product types include sulfate-free shampoos, baby washes, hand soaps, and micellar cleansers. The ingredient is listed on the EU CosIng inventory and is subject to Regulation (EC) No 1223/2009; manufacturing hygiene follows ISO 22716. Ready biodegradability is assessed according to OECD 301F. For export-grade material, the residual sodium chloroacetate limit of 10 mg/kg is a critical toxicological specification because higher levels are treated as a potential impurity of concern under current EU cosmetic safety assessment practice.
Integrated glyphosate complexes that use chloroacetic acid-derived glycine operate with a direct feedstock to the glycine–dimethyl phosphite–paraformaldehyde route, avoiding the iminodiacetic acid oxidation and nitrile handling associated with the IDAN route. Chloroacetic acid is reacted with ammonia and ammonium bicarbonate in the presence of hexamethylenetetramine at 70–90°C for 3–6 h; the molar input of ammonia to chloroacetic acid is 1.4–1.8:1, and urotropine catalyst is charged at 0.5–2.0 wt% relative to chloroacetic acid. The reactor is a jacketed 316L or titanium-clad vessel because the liquid contains high chloride and ammonium salt concentrations; off-gas is scrubbed with dilute sulfuric acid to recover ammonia and reduce amine emissions. Crude glycine is isolated by cooling crystallization at 5–15°C, followed by centrifugation and washing with methanol or deionized water; impurity control focuses on iminodiacetic acid and nitrilotriacetic acid, which must remain below 0.5% w/w and 0.1% w/w, respectively, to avoid later glyphosate quality penalties. In the subsequent synthesis, glycine reacts with paraformaldehyde and dimethyl phosphite in methanol or triethylamine-mediated media, producing glyphosate acid that is converted to the 41% isopropylamine salt soluble concentrate containing 356 g/L glyphosate acid equivalent. The formulation loading of the 480 g/L isopropylamine salt active ingredient is adjusted according to target concentration; the final SL typically contains 10–15% surfactant wetter. Terminal product types include non-selective herbicide water-soluble concentrates, pre-harvest vegetation management formulations, and industrial vegetation control products. Technical material is assessed under FAO/WHO specification 284/TC, soluble concentrate under 284/SL, and maximum residue levels are established in 40 CFR 180.364 and EU Regulation (EC) No 396/2005 as amended. Operational boundaries include the need to manage formaldehyde release from both urotropine decomposition and the glyphosate condensation stage; inadequate scrubbing permits formaldehyde above 1 mg/m³ in working-area air, exceeding common occupational exposure limits.
For cyanoacrylate monomer supply chains, the conversion of chloroacetic acid to sodium cyanoacetate introduces a nitrile group that later participates in Knoevenagel condensations and, after esterification and depolymerization, in cyanoacrylate monomer synthesis. Chloroacetic acid is neutralized with sodium carbonate to pH 7.5–8.5, then reacted with 30–35% aqueous sodium cyanide at 30–70°C; the mole ratio of sodium cyanide to chloroacetic acid is 1.03–1.08:1, and the reactor headspace is maintained under negative pressure with an alkaline hypochlorite or hydrogen peroxide scrubber to destroy hydrogen cyanide vapors. The resulting sodium cyanoacetate is acidified with sulfuric acid to pH 1.5–2.5, extracted with methyl isobutyl ketone or ethyl acetate, and concentrated; subsequent esterification with ethanol or methanol yields ethyl or methyl cyanoacetate. For cyanoacrylate adhesives, the cyanoacetate ester is subjected to Knoevenagel condensation with formaldehyde or paraformaldehyde, producing an oligomeric polycyanoacrylate that is thermally depolymerized at 150–200°C under vacuum, with the monomer distilled and stabilized with 10–500 mg/kg sulfur dioxide or methanesulfonic acid. Monomer purity above 99.5% w/w and water content below 100 mg/kg are common release criteria; higher residual water initiates premature anionic polymerization in storage. Terminal product types include industrial instant adhesives, medical tissue adhesives tested under ISO 10993-5 and ISO 10993-10, and pharmaceutical intermediates. Published data for specific depolymerization equipment configurations are limited because cyanoacrylate monomer synthesis is often proprietary; the general vacuum-distillation parameters are used for process design. Occupational exposure to cyanide and nitrile-bearing vapors is controlled in accordance with national occupational exposure limits, and the final medical adhesive device is subject to EU Medical Device Regulation (EU) 2017/745 or FDA 510(k) requirements depending on jurisdiction.
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Chloroacetic acid, CAS 79-11-8, is the monochlorinated derivative of acetic acid with the molecular formula ClCH2COOH and a molar mass of 94.49 g mol−1. Commercial product models are commonly designated CAA-Flake, CAA-Molten, and CAA-80 Liquid; the aqueous grade contains 80.0±1.0% chloroacetic acid. Solid material is supplied as white to off-white crystalline flakes or prills with a melting range of 61–63 °C and a boiling point of approximately 189 °C. The density of the solid is approximately 1.58 g cm−3 at 25 °C. The alpha-chloro substituent reduces the pKa from acetic acid’s 4.76 to 2.87 at 25 °C; this acidity increase, together with the polarizable carbon-chlorine bond, provides the nucleophilic displacement reactivity used in downstream etherification, amination, and thioether formation. The substance is hygroscopic. Flake product exposed to ambient moisture below 60 °C forms surface hydrate films and cakes rapidly. The EC number 201-178-4 identifies the substance under REACH.
Bulk monochloroacetic acid is not specified solely by assay. The relevant parameters are free acidity, dichloroacetic acid, acetic acid, water, iron, and appearance. Dichloroacetic acid is the most significant organic impurity because its higher acid strength and extra chlorine can increase byproduct formation in carboxymethylation and esterification. Table 1 lists typical specification ranges for flake or molten material and for aqueous 80% product.
| Parameter | Flake/molten grade | Aqueous 80% solution | Routine method |
|---|---|---|---|
| Chloroacetic acid content | ≥99.0% | 80.0±1.0% | Acid-base titration after hydrolysis/esterification |
| Dichloroacetic acid | ≤0.5% | ≤0.3% | GC after methyl ester formation |
| Acetic acid | ≤0.2% | ≤0.2% | GC after methyl ester formation |
| Water | ≤0.2% | 20.0±1.0% | Karl Fischer, ASTM E203 |
| Iron | ≤5 mg kg−1 | ≤3 mg kg−1 | ICP-OES |
| Appearance | White to off-white crystalline solid | Clear liquid | Visual inspection |
The ≤0.5% dichloroacetic acid ceiling is common for flake and molten grades. Water above 0.2% in solid product increases caking and can raise free chloride after neutralization. Iron is controlled because dissolved iron catalyses oxidative discoloration in surfactant esters and can precipitate in alkaline cellulose systems. Producers operating under ISO 9001:2015 maintain batch traceability for these parameters; the management standard does not alter specification limits but supports certificate-of-analysis reliability.
Industrial production of monochloroacetic acid is based on the catalytic chlorination of acetic acid. Sulfur or acetic anhydride is used as the halogenation catalyst, and the reaction is conducted in glass-lined or fluoropolymer-lined equipment at 100–140 °C. The crude product contains acetic acid, dichloroacetic acid, and trichloroacetic acid as byproducts. Crystallization at controlled cooling rates precipitates monochloroacetic acid while the higher-chlorinated homologues remain in the mother liquor. The temperature gradient and wash ratios determine residual dichloroacetic acid and trichloroacetic acid levels. This production route explains the typical flake assay of ≥99.0% with ≤0.5% dichloroacetic acid; tighter impurity ceilings require additional crystallization or solvent washing.
Quality control for monochloroacetic acid uses titration for total acidity, gas chromatography after methyl ester formation for organic impurities, Karl Fischer titration per ASTM E203 for water, and inductively coupled plasma optical emission spectroscopy for trace metals. The gas chromatographic method resolves monochloroacetic acid, dichloroacetic acid, and acetic acid esters and is calibrated with certified reference standards.
Compared with dichloroacetic acid and trichloroacetic acid, monochloroacetic acid has a single alpha-chlorine atom. The structural difference gives a monofunctional alkylation profile in Williamson etherification and amination reactions; dichloroacetic acid can introduce a second chlorine-bearing carbon and is not a direct substitute. The acid strengths follow inductive electron withdrawal: acetic acid 4.76, chloroacetic acid 2.87, dichloroacetic acid 1.25, and trichloroacetic acid 0.77 pKa. Boiling points of the chlorinated homologues are close, so industrial purification relies on crystallization rather than simple distillation.
| Property | Acetic acid | Chloroacetic acid | Dichloroacetic acid | Trichloroacetic acid |
|---|---|---|---|---|
| CAS No. | 64-19-7 | 79-11-8 | 79-43-6 | 76-03-9 |
| Molar mass | 60.05 g mol−1 | 94.49 g mol−1 | 128.94 g mol−1 | 163.38 g mol−1 |
| pKa at 25 °C | 4.76 | 2.87 | 1.25 | 0.77 |
| Boiling point | 118 °C | 189 °C | 194 °C | 196 °C |
| Typical role in carboxymethylation | No reactive C-Cl alkylation site | Monofunctional alkylating agent | Trace impurity; higher acid strength and lower selectivity | Trace impurity; strong acid and alkaline decarboxylation route |
Trichloroacetic acid is not a substitute in carboxymethylation; under alkaline heat it decarboxylates to chloroform and carbon dioxide. Acetic acid at ≤0.2% contributes no alpha-chloro leaving group and acts as a diluent. The higher acid strength of dichloroacetic acid also means that its residual presence accelerates acid-catalysed hydrolysis in aqueous formulations, which is why it is held to tight limits.
Industrial sodium carboxymethyl cellulose is produced by a two-stage alkalization-etherification sequence. Cellulose pulp is mercerized with aqueous sodium hydroxide in a horizontal sigma-arm kneader at 50–60 wt% NaOH on cellulose. Chloroacetic acid is separately neutralized with sodium hydroxide to sodium chloroacetate at pH 7.5–8.5 and then added at a molar ratio of 0.5–1.2 mol per anhydroglucose unit. The etherification temperature is maintained at 60–80 °C for 1–3 h. The competing hydrolysis of sodium chloroacetate to sodium glycolate increases with temperature and free-water content. In sigma-arm mixers with working volumes from 500 L to 1500 L, temperature overshoot above 85 °C produces higher sodium glycolate content and visible discoloration. The degree of substitution for commercial grades ranges from 0.4 to 1.2. Stoichiometric efficiency of chloroacetic acid incorporated as carboxymethyl groups is usually 60–75%; the remainder is hydrolyzed to sodium glycolate. Residual sodium glycolate in dried technical CMC is commonly controlled below 1.5 wt%, with lower limits for food-grade E466 material under Commission Regulation (EU) No 231/2012. Staged addition of sodium chloroacetate, reduced free water, and rapid discharge after the etherification plateau are used to limit glycolate formation.
After etherification, the paste is discharged to a belt or drum dryer at 80–120 °C and dried to a final moisture content below 10 wt%. Milling then produces the required particle size. The final polymer, not the chloroacetic acid intermediate, is subject to food-contact purity criteria. The difference between technical and purified grades of CMC therefore reflects washing efficiency, residual glycolate, and sodium chloride content rather than the initial monochloroacetic acid assay alone.
In 2,4-dichlorophenoxyacetic acid production, chloroacetic acid is converted to sodium chloroacetate and condensed with 2,4-dichlorophenol in aqueous alkaline solution at 100–140 °C for 2–6 h. The pH is held between 10 and 11; lower pH reduces phenolate ion concentration, while higher pH increases chloroacetate hydrolysis. A typical molar feed ratio of chloroacetic acid to 2,4-dichlorophenol is 1.05–1.15:1. The main yield losses are sodium glycolate formation and incomplete recovery of unreacted chlorophenol after acidification and solid-liquid separation. Glass-lined reactors are standard for the condensation. Acidic filtrate handling uses rubber-lined or fluoropolymer-lined steel because free chloride promotes pitting corrosion in 304L stainless steel.
Thioglycolic acid is manufactured from sodium chloroacetate and sodium hydrosulfide in aqueous medium at 40–60 °C under an inert nitrogen or argon blanket. Dissolved oxygen is a critical impurity; it oxidizes hydrosulfide to polysulfides, which reduce product purity and generate sulfur-containing byproducts. A molar charge ratio of NaSH to sodium chloroacetate of 1.05–1.20:1 is common. After reaction, the mixture is acidified with sulfuric or hydrochloric acid to pH 1–2 and the thioglycolic acid is recovered by extraction or distillation. In continuous plants, Hastelloy C-276 or glass-lined internals are preferred because combined chloride and sulfide ions attack 316L stainless steel. Vent lines require steam tracing and regular flushing; sulfur deposits and sodium chloride solids are known causes of pressure-drop excursions and blockages.
Residual chloroacetic acid in the crude thioglycolate is typically specified below 0.1% where the downstream use is a PVC organotin stabilizer intermediate, because unreacted alkylating agent consumes mercaptide functionality and alters tin-sulfur coordination. Published data for this specific threshold in all downstream ester types is limited, but the 0.1% limit appears in internal product transfer documents and supplier certificates of analysis.
Betaine-type amphoteric surfactants are produced by quaternizing tertiary fatty amines, such as cocamidopropyl dimethylamine, with sodium chloroacetate. The reaction is run at 80–95 °C in aqueous or water-ethanol media with pH controlled at 8.0–9.5. A molar excess of sodium chloroacetate of 1.05–1.10 is maintained to drive conversion, and residual chloroacetate is then hydrolyzed to glycolate. The final product typically contains 5–7 wt% sodium chloride from neutralization. Viscosity and gel-phase behavior are governed more by the fatty chain distribution and electrolyte content than by trace residual chlorinated acetic acid.
Cyanoacetic acid is produced from sodium chloroacetate and sodium cyanide at 60–90 °C in alkaline solution. Acidification must be conducted under closed venting because hydrogen cyanide is released below pH 7. Glycine is produced by ammonolysis of chloroacetic acid with excess aqueous ammonia and ammonium carbonate at 50–70 °C. Both routes release stoichiometric chloride. Glass-lined or fluoropolymer-lined reactors are standard in cyanide service; 316L stainless steel is avoided because chloride stress-corrosion cracking can initiate at weld heat-affected zones. In glycine plants, 316L may be acceptable for short-contact crystallizer bodies when chloride is diluted, but the ammonia-chloride mixture requires pH control to avoid corrosive ammonium chloride deposits. Cyanoacetic acid is subsequently hydrolyzed to malonic acid, which is one of the non-cellulose outlets for monochloroacetic acid.
Maintenance of molten chloroacetic acid in heat-traced transfer lines at 65–75 °C prevents solidification and flow restriction. Bulk storage tanks for molten grade are fabricated from carbon steel or 316L stainless steel with heating coils and dry-air blanketing. Aqueous 80% solution is more aggressive and is stored in lined vessels such as ebonite, polypropylene, or glass-fiber-reinforced plastic. Flake packaging must be kept sealed at ambient relative humidity below 60% to prevent caking. Chloroacetic acid vapour is corrosive to the respiratory tract and mucous membranes; the harmonised labelling under CLP Regulation (EC) No 1272/2008 includes acute toxicity and skin corrosion categories. Handling systems use closed pneumatic conveying for solid flake and dual mechanical seals or magnetically driven pumps for molten transfer.
Chloroacetic acid should not be combined with primary or secondary amines in closed reactors without provision for controlled heat removal; the amination reaction is exothermic and can generate localized pressure from ammonia displacement and carbon dioxide evolution.
