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Chemical method for synthesizing palmitoyl chloride

A palmitoyl chloride and chemical synthesis technology, applied in the field of chemical synthesis of palmitoyl chloride, can solve the problems of high sealing requirements of reaction equipment, difficult handling, pollution, etc., and achieve great implementation value and social and economic benefits, advanced process route, and simple operation. safe effect

Inactive Publication Date: 2009-09-09
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The product obtained by the phosphorus trichloride process contains a large amount of by-product phosphoric acid, and phosphorus oxychloride, as a chlorinated reagent, severely corrodes the equipment, and a large amount of phosphorus-containing wastewater is difficult to handle, causing serious pollution and environmental problems.
The tail gas of the thionyl chloride process contains a large amount of asphyxiating sulfur dioxide (one of the six indicators strictly controlled by the national environmental protection on the atmosphere), which is difficult to deal with. At present, the mixture of sodium sulfite and sodium chloride is mainly prepared by alkali absorption, but there are It is a big problem, and because it is an aqueous solution after being absorbed by alkali, it must be concentrated to obtain a mixture of sodium sulfite and sodium chloride, the production process consumes a lot of energy and the production cost is high
In addition, the transportation and use of thionyl chloride are strictly controlled, and the requirements for the tightness of the reaction equipment are high, and the investment is also large. At the same time, there are still problems such as low product yield and purity in the original process that need to be solved.

Method used

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  • Chemical method for synthesizing palmitoyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The amount ratio of feed material is palmitic acid: bis (trichloromethyl) carbonate: catalyzer is 1:0.34:0.01, and catalyzer is tetramethylguanidine, and organic solvent is toluene, and its consumption is 2 times of palmitic acid quality.

[0019] In a 250mL three-neck flask equipped with a thermometer, reflux condenser and mechanical stirring, add 25.6g (100mmol) of palmitic acid, 10.1g (34mmol) of bis(trichloromethyl)carbonate, 59.5ml of toluene and 0.1g of tetramethylguanidine g (1 mmol). After the addition, heat up to 80°C and react at 80-85°C for 7 hours. After the reaction is completed, evaporate the solvent under normal pressure and distill at a vacuum of 2.3kpa to collect fractions at 190-192°C to obtain 25.4g of palmitoyl chloride, with a product yield of 92.5 %, purity 98.5%. 1 H NMR (CDCl 3 )δ: 2.8(3,2H), 1.6~1.8(m,2H), 1.2~1.4(m,24H), 0.9(3,3H).

Embodiment 2

[0021] The amount ratio of feed material is palmitic acid: two (trichloromethyl) carbonates: catalyst is 1:0.7:0.01, and palmitic acid charging capacity is 25.6g (100mmol), two (trichloromethyl) carbonate charging capacity is 20.5 g (70mmol), the catalyst is 1,3-dimethyl-2-imidazolidinone, and its consumption is 0.1g (1mmol), and the organic solvent is toluene, and its consumption is 2 times of palmitic acid quality.

[0022] The reaction temperature was 80-85° C., and other operations were the same as in Example 1 to obtain 25.1 g of palmitoyl chloride with a product yield of 91.5% and a purity of 99.0%. 1 H NMR (CDCl 3 )δ: 2.8(3,2H), 1.6~1.8(m,2H), 1.2~1.4(m,24H), 0.9(3,3H).

Embodiment 3

[0024] The amount ratio of the feed material is palmitic acid: two (trichloromethyl) carbonates: the catalyst is 1:1:0.02, the amount of palmitic acid is 25.6g (100mmol), and the amount of bis(trichloromethyl) carbonates is 29.7 g (100mmol), the catalyst is pyridine, and its consumption is 0.2g (2mmol), and the organic solvent is tetrahydrofuran, and its consumption is 2 times of palmitic acid quality.

[0025] The reaction temperature was 60-65° C., and other operations were the same as in Example 1 to obtain 26.1 g of palmitoyl chloride with a product yield of 95.0% and a purity of 99.0%. 1 H NMR (CDCl 3 )δ: 2.8(3,2H), 1.6~1.8(m,2H), 1.2~1.4(m,24H), 0.9(3,3H).

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Abstract

The invention relates to a chemical synthesis method of palmitoyl chloride, in particular to a chemical synthesis method of preparing palmitoyl chloride by reacting bis(trichloromethyl)carbonate and palmitic acid. The palmitoyl chloride is prepared by using palmitic acid and bis(trichloromethyl)carbonate as raw materials and reacting in an organic solvent at 50-150° C. for 1-10 h under the action of an organic amine catalyst. The present invention uses bis(trichloromethyl)carbonate instead of thionyl chloride or phosphorus oxychloride to react with palmitic acid in an organic solvent under the action of a catalyst to prepare palmitoyl chloride. The process route is advanced, the process conditions are reasonable, and the operation is simple and safe. The reaction yield is high, the production cost is low, the three wastes are small, and it has great implementation value and social and economic benefits.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of palmitoyl chloride, in particular to a chemical synthesis method of preparing palmitoyl chloride by reacting bis(trichloromethyl)carbonate and palmitic acid. (2) Background technology [0002] Palmitoyl chloride is an important organic intermediate for the synthesis of alcohols and phenolic palmitic acid esters, such as the production of odorless chloramphenicol. [0003] Before the present invention is given, the chemical synthesis method of palmitoyl chloride in the prior art is mostly prepared by chlorination of palmitic acid and phosphorus oxychloride or thionyl chloride. As proposed in Functional Materials 2002, 33(6), it is prepared by reacting 18.2g (0.070mol) of palmitic acid and 10.4ml (0.035mol) of thionyl chloride for 4h. [0004] The product obtained by the phosphorus trichloride process contains a large amount of by-product phosphoric acid, and phosphorus oxychloride, as a chlori...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C53/42C07C51/60
Inventor 陈志卫苏为科徐之俊
Owner ZHEJIANG UNIV OF TECH
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