Chloroacetyl Chloride CAS 79-04-9

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  • Appearance: Clear colorless to slightly yellow liquid
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: Chloroacetyl Chloride Supplement

Basic Info of Chloroacetyl Chloride

What is Chloroacetyl Chloride?

Chloroacetyl chloride is active in chemical properties, decomposes in water and alcohol, and can be used as an acylation reagent, such as reacting with naphthalene, cyclopropane, ethylene and other reagents, and reducing it with tetrahydroaluminum lithium in ether to obtain 2-chloroethanol. Preparation method: It is prepared by the reaction of acetyl chloride and chlorine gas under the irradiation of a mercury lamp, or by the action of chloroacetic acid and phosphorus trichloride.

Chloroacetyl chloride is an important organic chemical intermediate, which is widely used in pesticides, medicines, dyes, various auxiliaries and other fields. As an acylating agent with excellent performance, the current commercial products are fine Chemicals and chemical reagents. However, the purity of chloroacetyl chloride produced in China is not high (95% ± 2%), which contains dichloroacetyl chloride that is difficult to remove, resulting in low quality of chloroacetyl chloride and limited application fields. Due to its low purity, it cannot be used for Semiconductor integrated circuit manufacturing and crystalline silicon solar cell manufacturing. The development of high-value-added and high-purity products not only meets the needs of high-tech industries, but also brings economic benefits to enterprises and promotes enterprise upgrading.

Chloroacetyl Chloride Uses

  1. Chloroacetyl chloride is generally used as a raw material for medicines as well as pesticides, especially for the manufacturing of herbicides such as butachlor as well as alachlor.
  2. Chloroacetyl chloride is an important intermediate of pesticides, which can produce pesticides dimethoate, omethoate, fungicides imazalil, metalaxyl, oxaxyl, herbicides alachlor, acetochlor, precochlor, butachlor, clochlor, chlorfenapyr, metolachlor, metolachlor, salinaphos, fenthiochlor, and so on, are likewise vital pharmaceutical intermediates, which can be used to manufacture chlordiazepoxide, diazepam, Nitrovalium, lidocaine, praziquantel, methoxaine, etimothiazide, pipampazepine, fluconazole, econazole, etc.
  3. Chloroacetyl chloride is made use of in the production of chemical dimethoate, fluoroacetamide, drugs, solvents, cooling agents, fire extinguishing representatives, dyeing accessories, lubricant ingredients, and so on. Chloroacetyl chloride has a vast array of uses. There are more than 40 ranges of 3 collection of herbicides that need to eat chloroacetyl chloride.
  4. Chloroacetyl chloride is an energetic acylating agent as well as an essential organic synthesis intermediate. It is extensively made use of in the synthesis of amino acids, pesticides, medicines, dyes, additives, removal solvents, cooling agents, fire snuffing out agents, lubricating substance additives, as well as army dangerous gases. In other facets, it is presently one of the most extensively made use of as well as the biggest amount, particularly in chemicals. It is the synthetic intermediate of crucial chemicals chloramine, acetochlor as well as omethoate.
  5. Chloroacetyl chloride is used in drugs, chemicals, as well as can additionally be utilized in natural synthesis for removal solvents, refrigerants, color accessories as well as lubricating oil ingredients. Manufacture of chloroacetophenone (tear gas), prep work of amino acids.

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The Purification Method of Chloroacetyl Chloride

  1. Adsorption: add 2 liters of crude chloroacetyl chloride to the ground glass flask, then add 30 grams of activated carbon, heat up to 70-80°C under stirring, keep the temperature for 2 hours, stir continuously for 4 hours, then naturally cool and let stand Overnight, the activated carbon precipitate was separated and removed to obtain a clear liquid of chloroacetyl chloride.

  2. Replacement: put the chloroacetyl chloride clear liquid into a beaker, put in 50 grams of zinc particles, install a reflux device and heat to 85 ℃ ~ 100 ℃ reflux for 2 hours, let stand for cooling overnight, separate and remove the precipitate and unreacted The zinc particles were obtained, and the clear liquid was taken for the next step of rectification.
  3. Rectification for the first time: in the rectification device made of glass, add the clear liquid obtained after displacement filtration, add 6ml of glacial acetic acid, with the residual chloride in the crude product of esterification chloroacetyl chloride, heat to carry out rectification, The 102-106°C fraction was collected for the second rectification.
  4. Second rectification: In the rectification device made of quartz, add the fraction after the first rectification, continue the rectification, and collect the 104-106°C fraction for the third rectification.
  5. The third rectification: in the rectification device made of quartz, add the fraction after the second rectification, and continue the rectification. The part where the rectification device communicates with the atmosphere should be equipped with anhydrous calcium chloride. The drying facility is used to prevent moisture from entering the rectification system, and the fraction at 105 to 106 °C is collected, which is the finished product.

Preparation Method of Chloroacetyl Chloride

Chloroacetic acid is slightly heated in the presence of an acid chloride agent to obtain chloroacetyl chloride. The acid chloride agent includes phosphorus trichloride, phosgene, thionyl chloride, etc. Generally, phosphorus trichloride is commonly used as the acid chloride agent, and the reaction temperature is 50~ 60°C.

The method has low cost and readily available raw materials. In industrial production, phosgene is also used as acyl chloride agent, the reaction is convenient, no three wastes are generated, and thionyl chloride is commonly used as acyl chloride agent in laboratory. In addition, chloroacetic acid chlorine chlorination method can also be used, and the cost of this method is also lower, but hypochlorous acid is generated in the reaction process.

ClCH2COOH+Cl2→ClCH2COCl+[HOCl]

Put glacial acetic acid into the chlorination pot, slowly add chlorosulfonic acid, heat up to above 60°C, start to introduce chlorine gas, start stirring, continue to heat up, keep the reaction temperature at (98±3)°C, and react for 8 hours until the reaction solution The relative density reaches 1.37-1.40, and the chlorine gas is stopped for cooling. Put dichlorodisulfide into the above reaction solution, start stirring and pass chlorine gas when the temperature drops to 50-60 °C, control the reaction temperature at (48±3) °C, and pass chlorine gas for about 5h. The crude product is obtained, and finally the finished product is obtained by distillation.

Reaction equation: CH3COOH+Cl2[HSO3Cl]→ClCH2COOH+HCl4ClCH2COOH+3Cl2[S2Cl2]→4CChemicalbooklCH2COCl+2SO2↑+4HCl

Chloroacetyl chloride can also be obtained by using manganese dioxide and sulfur as catalysts, and using acetic acid as a raw material for secondary heating and direct chlorination. There is also a continuous pipeline reaction with phosgene using acetic acid as a raw material, which can also produce chloroacetyl chloride.

Reaction equation: CH3COOH+COCl2→C1CH2COCl+}tCOOH

Add acetyl chloride in the reaction pot, use sulfuric acid as a catalyst, and pass chlorine gas for chlorination to obtain chloroacetyl chloride.

Reaction equation: CH3COCl+Cl2[H2SO4]→ClCH2COCl+HCl

The ketene and chlorine gas are respectively introduced into the tower reactor, the reaction temperature is 15~30℃, the reaction is carried out in a certain solvent, the reaction liquid enters the storage tank, and then the distillation is carried out. The solvent is then rectified to obtain the product.

Reaction equation: CH2C=O+Cl2→ClCH2COCl

The method is the most reasonable, basically no three wastes are discharged, the product has high purity, high yield, the purity can reach more than 99%, and basically does not contain dichloroacetyl chloride. Foreign Monsanto Company and Dow Chemical Company use this method to produce chloroacetyl chloride. The German BASF company uses chloroacetic acid phosgene method. The output of chloroacetyl chloride in foreign countries is nearly 100,000 tons/a, 40% to 60% are used for pesticides, and 20% to 30% are used for medicine.

Renference

  1. Chloroacetyl Chloride – ChemicalBook
  2. Chloroacetyl Chloride – PubChem
  3. [Chinese invention] CN201110230898.8 A kind of purification method of chloroacetyl chloride

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