Chloroacetyl chloride
Chloroacetyl chloride
CAS: 79-04-9
Molecular Formula: C2H2Cl2O
Chloroacetyl chloride - Names and Identifiers
Chloroacetyl chloride - Physico-chemical Properties
| Molecular Formula | C2H2Cl2O |
| Molar Mass | 112.94 |
| Density | 1.419g/mLat 20°C |
| Melting Point | −22°C(lit.) |
| Boling Point | 105-106°C(lit.) |
| Flash Point | >100°C |
| Water Solubility | reacts |
| Solubility | Miscible with ethyl ether, acetone, benzene and carbon tetrachloride. |
| Vapor Presure | 60 mm Hg ( 41.5 °C) |
| Vapor Density | 3.9 (vs air) |
| Appearance | Liquid |
| Color | Clear colorless to slightly yellow |
| Exposure Limit | ACGIH: TWA 0.05 ppm; STEL 0.15 ppm (Skin)NIOSH: IDLH 1.3 ppm; TWA 0.05 ppm(0.2 mg/m3) |
| Merck | 14,2067 |
| BRN | 605439 |
| Storage Condition | Store at RT. |
| Stability | Stable. Incompatible with strong bases, alcohols, strong oxidizing agents. May react violently on exposure to water or moisture. |
| Sensitive | Moisture Sensitive |
| Refractive Index | n20/D 1.453(lit.) |
| Physical and Chemical Properties | Characteristics of colorless or yellowish liquid, there is a strong irritation. melting point boiling point 107 ℃ freezing point -22.5 ℃ relative density 1.4202 refractive index 1.4530 solubility: soluble in benzene, carbon tetrachloride, ether and chloroform. |
| Use | Used in medicine, pesticide, can also be used as extraction solvent, refrigerant, dye aid and lubricating oil additives |
Chloroacetyl chloride - Risk and Safety
| Risk Codes | R14 - Reacts violently with water R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R35 - Causes severe burns R48/23 - R50 - Very Toxic to aquatic organisms R29 - Contact with water liberates toxic gas |
| Safety Description | S9 - Keep container in a well-ventilated place. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S7/8 - |
| UN IDs | UN 1752 6.1/PG 1 |
| WGK Germany | 3 |
| RTECS | AO6475000 |
| TSCA | Yes |
| HS Code | 29159000 |
| Hazard Class | 6.1 |
| Packing Group | I |
Chloroacetyl chloride - Upstream Downstream Industry
| Raw Materials | sulfur dichloride Sulfur(α) Sulfur(α) Chlorine Chloroacetic acid diketene |
| Downstream Products | Metolachlor Pretilachlor Anilofos diclofenac sodium nitrazepam methanol solution lidocaine hydrochloride |
Chloroacetyl chloride - Nature
Open Data Verified Data
This product is a colorless or yellowish liquid, which is highly irritating and decomposes in water. Freezing point -22.5 °c. Boiling Point 107 °c. The relative density was 1.4202. Refractive index 4530. Soluble in benzene, carbon tetrachloride, ether and chloroform.
Last Update：2024-01-02 23:10:35
Chloroacetyl chloride - Preparation Method
Open Data Verified Data
Chloroacetyl Chloride was prepared by the reaction of chloroacetic acid with chlorine and dichloromethane.
Last Update：2022-01-01 10:32:14
Chloroacetyl chloride - Use
Open Data Verified Data
for the synthesis of medicines and pesticides, can also be used as extraction solvents, refrigerants, dyeing aids and lubricating oil additives.
Last Update：2022-01-01 10:32:14
Chloroacetyl chloride - Safety
Open Data Verified Data
- This product is a strong irritating liquid, rat oral LD50 120mg/kg, mouse intravenous injection ld5032 mg/kg. Operators should wear protective equipment, and the production site should have good ventilation conditions. The equipment should be closed.
- glass bottles or ceramic cans are packaged in wooden boxes for external use. Pay attention to sealing, moisture, sun protection, according to the provisions of the transport of toxic chemicals.
Last Update：2022-01-01 10:32:15
Chloroacetyl chloride - Reference Information
| freezing point | -22.5 ℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Application | Chloroacetyl Chloride is an important intermediate of pesticide, which can produce insecticide dimethoate, omethoate, fungicide imazalil, metalaxyl, oxalachlor, herbicide alachlor, acetochlor, alachlor, butachlor, clachlor, trimethoprim, metolachlor, metolachlor, salbutamol, mefenozamide, etc, at the same time, it is also an important pharmaceutical intermediate, which can be used for the synthesis of chlordiazepoxide, diazepam, nitrazepam, lidocaine, praziquantel, mesocaine, thiazide, piperacillin, fluconazole, econazole and the like. It is used in the production of pesticide Dimethoate, fluoroacetamide, medicine, solvent, refrigerant, fire extinguishing agent, dyeing aid, lubricating oil additive, etc. Chloroacetyl Chloride is widely used, only herbicides have 3 series of more than 40 varieties need to consume Chloroacetyl Chloride. Chloroacetyl Chloride is a kind of active acylating agent and important organic synthesis intermediates, widely used in amino acids, pesticides, pharmaceuticals, dyes, additives, extraction solvents, refrigerants, fire extinguishing agents, lubricating oil additives, the synthesis of military toxic gases, especially in the most widely used pesticides, the amount is also the largest. It is an important intermediate for the synthesis of pesticide Oxadiazole, acetochlor, omethoate and so on. it can be used in organic synthesis, such as medicine, pesticide, extraction solvent, refrigerant, dyeing aid and lubricant additive. . Production of chloroacetophenone (tear gas), the preparation of amino acids. |
| production method | obtained by chlorination of glacial acetic acid: primary chlorination: add glacial acetic acid into the chlorination Pan, slowly add chlorosulfonic acid, the temperature is raised to above 60 ℃, chlorine gas is introduced, the stirrer is started, and the temperature is kept at 98±3 ℃ for 8h (the amount of chlorine is 4-5kg/h), chlorine was stopped until a relative density of 1.37-1.40 was measured and cooling was performed. Secondary chlorination: put the dichlorodisulfide into the reaction Pan, wait for the temperature to drop to 50-60 ℃, start passing chlorine and stirring, control the reaction temperature at 48±3 ℃, pass chlorine until the reflux liquid is light yellow as the end point, the crude product was obtained. Finally, the product was obtained by distillation with a yield of about 80%. Secondary chlorination can also be by chloroacetic acid and benzoyl chloride reaction: In addition, with chloroacetic acid as raw material, by phosphorus trichloride chlorination, reaction temperature is 50-60 deg C; Or chloroacetic acid in sulfur powder, anhydrous zinc chloride in the presence, chloroacetyl Chloride can also be obtained by chlorination at 60 ℃, The yield was 85-93%. Chloroacetyl Chloride can also be obtained by the reaction of chloroacetic acid with chlorine and dichloromethane. There are several preparation methods. Chloroacetic acid as raw material chloroacetic acid in the presence of acid chlorinating agent slightly heated, can get Chloroacetyl Chloride, acid chlorinating agent phosphorus trichloride, phosgene, thionyl chloride, etc, the reaction temperature was 50 to 60 °c. The method has low cost and easy availability of raw materials. In industrial production, phosgene is also useful as acyl chlorinating agent, the reaction is convenient, no three wastes are produced, and the commonly used thionyl chloride in the laboratory is acyl chlorinating agent. In addition, the chloroacetic acid chlorine gas chlorination method can also be used, and the cost of the method is also low, but there is the formation of hypochlorous acid in the reaction process. ClCH2COOH + Cl2 → ClCH2COCl +[HOCl] glacial acetic acid is used as raw material to put glacial acetic acid into chlorination Pan, chlorosulfonic acid is slowly added, the temperature is raised to above 60 ℃, chlorine gas is introduced, stirring is started, and the temperature is continued, the reaction temperature was maintained at (98±3) ° C., and the reaction was carried out for 8 hours until the density of the reaction liquid phase reached 1.37 to 1.40, and the cooling with chlorine gas was stopped. Dichlorodisulfide was added to the above reaction solution, and chlorine gas was stirred until the temperature dropped to 50~60 ℃, and the reaction temperature was controlled (48±3)℃, chlorine gas time is about 5h, the reflux liquid shows light yellow as the end point to get the crude product, and finally by distillation to get the finished product. Reaction equation: CH3COOH + Cl2[HSO3Cl]→ ClCH2COOH + HCl4ClCH2COOH +3 Cl2[S2Cl2]→ 4ClCH2COCl +2SO2 ++ + 4HCl can also be used as catalyst with manganese dioxide and sulfur respectively, chloroacetyl Chloride can also be obtained by direct chlorination with acetic acid as raw material at secondary temperature. And acetic acid as raw material, and phosgene pipeline continuous reaction, can also produce Chloroacetyl Chloride. Reaction equation: CH3COOH + COCl2 → C1CH2COCl +}tCOOH acetyl chloride is added in a reaction pot with acetyl chloride as a raw material, and sulfuric acid is used as a catalyst, chlorine gas is introduced for chlorination to obtain Chloroacetyl Chloride. Reaction equation: CH3COCl + Cl2[H2SO4]→ ClCH2COCl + HCl the ketene and chlorine gas are respectively fed into the column reactor with ketene as raw material, and the reaction temperature is 15~30 ℃, the reaction is carried out in a certain solvent, and the reaction solution enters the storage tank, and then is distilled. The first fraction is acetyl chloride, then the solvent is distilled off, and then the product is obtained by distillation. Reaction equation: CH2C = O + Cl2 → ClCH2COCl this method is the most reasonable, Basically no three waste discharge, high product purity, high yield, purity of more than 99%, basically does not contain dichloroacetyl chloride, foreign montelukast company, Dow Chemical Company adopt this method to produce Chloroacetyl Chloride, the German BASF company uses phosgene chloroacetic acid method. The output of Chloroacetyl Chloride abroad is nearly 100,000 tons/a,40% ~ 60% for pesticides, 20% ~ 30% for medicine. |
| category | corrosive article |
| toxicity grade | high toxicity |
| Acute toxicity | oral-rat LD50: 208 mg/kg; Oral-mouse LD50: 220 mg/kg |
| flammability hazard characteristics | decomposition of toxic chloride gases by heat or water |
| storage and transportation characteristics | The warehouse was ventilated and dried at low temperature; With H pore forming agent, alkali, separate storage of cyanide |
| extinguishing agent | Sand, carbon dioxide; Do not use water! |
| Occupational Standards | TLV-TWA 0.05 PPM (0.2 mg/m3); Tel 0.15 PPM (0.6 mg/m3) |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
| immediate life-and health-threatening concentration | 1.3 ppm (6 mg/m3) |
Last Update：2024-04-10 22:29:15
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View History
Chloroacetyl chloride
Vinyl benzyl ether
右美沙芬杂质C
propan-2-yl chloroacetate
1-NAPHTHYL TRIFLATE
3-(三氟甲基)苯乙酸甲酯
3-氟-4-硝基嘧啶-N-氧化物
Vinyl benzyl ether
右美沙芬杂质C
propan-2-yl chloroacetate
1-NAPHTHYL TRIFLATE
3-(三氟甲基)苯乙酸甲酯
3-氟-4-硝基嘧啶-N-氧化物
Raw Materials for Chloroacetyl chloride
Downstream Products for Chloroacetyl chloride