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6-hydroxy-8-chloro ethyl caprylate preparation method thereof

A technology of ethyl chlorooctanoate and hydroxyl, which is applied in the field of boron-containing wastewater treatment and the preparation of ethyl 6-hydroxy-8 chlorooctanoate, achieving the effects of simple synthesis steps, avoiding direct discharge, and reducing the use of organic solvents

Active Publication Date: 2017-07-21
JIANGSU TOHOPE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But boron is not recycled as a resource

Method used

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  • 6-hydroxy-8-chloro ethyl caprylate preparation method thereof
  • 6-hydroxy-8-chloro ethyl caprylate preparation method thereof
  • 6-hydroxy-8-chloro ethyl caprylate preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Dissolve 100Kg ethyl 6-oxo-8-chlorooctanoate in 500Kg dichloroethane, keep the temperature at 10-30°C, add 1Kg tetrabutylammonium bromide, add dropwise 17% sodium borohydride containing 5Kg Ammonia solution 100Kg, react for 4 hours, filter and separate layers, adjust the pH of the organic layer to 5-6 with hydrochloric acid, heat and concentrate under reduced pressure at 0.1MPa until the temperature is 110°C, and obtain 6-hydroxy-8-chlorooctanoic acid ethyl alcohol with a purity of 92%. Ester concentrate 98Kg. The water layer passes through the filter to obtain the precipitated sodium metaborate, the filtrate is concentrated and recovered 75Kg of 10% ammonia water for reuse, cooled and crystallized, filtered to obtain sodium metaborate, the mother liquor is returned to the sleeve, and the obtained sodium metaborate is combined to 13.8Kg, and dried at 100°C to obtain 7.6Kg, 95% purity.

Embodiment 2

[0040] Dissolve 100Kg ethyl 6-oxo-8-chlorooctanoate in 500Kg dichloroethane, keep the temperature at 10-30°C, add 1Kg tetrabutylammonium bromide, add dropwise 10% sodium borohydride containing 8Kg Ammonia solution 100Kg, of which 75Kg ammonia water is recovered from Example 1, reacted for 2 hours, filtered and separated, the organic layer was adjusted to pH=5-6 with hydrochloric acid, concentrated under reduced pressure at 0.1MPa until the temperature was 110°C, and the purity was 90%. 99Kg of 6-hydroxy-8-chlorooctanoic acid ethyl ester concentrate. The water layer was passed through a filter to obtain the precipitated sodium metaborate, the filtrate was combined with the mother liquor of Example 1, concentrated and recovered 60Kg of 7% ammonia water, cooled and crystallized, filtered to obtain sodium metaborate, and the combined sodium metaborate 21.5Kg was dried at 100°C 11Kg was obtained with a purity of 98%.

Embodiment 3

[0042] Dissolve 100Kg of ethyl 6-oxo-8-chlorooctanoate in 500Kg of dichloroethane, keep the temperature at 10-30°C, add 5Kg of tetrabutylammonium bromide, add dropwise 5% of sodium borohydride containing 8Kg Ammonia solution 100Kg, react for 4 hours, filter and separate layers, adjust the pH of the organic layer to 5-6 with hydrochloric acid, heat and concentrate under reduced pressure at 0.1MPa until the temperature is 110°C, and obtain 6-hydroxy-8-chlorooctanoic acid ethyl alcohol with a purity of 94%. Ester concentrate 95Kg. The water layer was passed through the filter to obtain the precipitated sodium metaborate, and the filtrate recovered 50Kg of 4% ammonia water. At the same time, the mother liquor was concentrated, cooled and crystallized, and then filtered to obtain sodium metaborate. The sodium metaborate was combined to obtain 20.7Kg, and dried at 100°C to obtain 11.1Kg. The purity is 94%.

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Abstract

The present invention discloses a preparation method of a lipoic acid key intermediate 6-hydroxy-8-chloro ethyl caprylate having a structure formula represented by a formula (I), wherein 6-oxo-8-chloro ethyl caprylate having a structure represented by a formula (II) is adopted as a starting raw material and is reduced to prepare the 6-hydroxy-8-chloro ethyl caprylate. Compared to the preparation method in the prior art, the preparation method of the present invention mainly has the following advantages that the synthesis steps are simple, the use of the organic solvent is reduced, the direction discharging of the wastewater is avoided, the generated sodium metaborate is easily separated and cannot react with other substances, the sodium metaborate solid is successfully recovered, and the ammonia water is recovered and utilized; particularly by recovering the sodium metaborate, the possibility is created for the recycling of the boron element through the sodium borohydride preparation with the further industrial recovery of the boron element; and the whole process meets the green synthesis and cleaning production technology requirement, and is suitable for the large-scale industrial production. The formulas (I) and (II) are defined in the specification.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis route design and industrial wastewater treatment, and in particular relates to a preparation method of 6-hydroxy-8-chlorooctanoic acid ethyl ester and a boron-containing wastewater treatment method. Background technique [0002] [0003] 6-Hydroxy-8-chlorooctanoic acid ethyl ester is one of the intermediates for the preparation of lipoic acid starting from adipic acid, in which 6-oxo-8-chlorooctanoic acid ethyl ester is used to prepare 6-hydroxy-8- Ethyl chlorooctanoate. Lipoic acid has a strong antioxidant capacity, and is mainly used in the treatment of diabetic peripheral neuropathy in China; in addition to being used as a medicine, it is also widely used as a dietary supplement and cosmetic raw material abroad. [0004] The reduction of 6-oxo-8-chlorooctanoic acid ethyl ester to prepare 6-hydroxy-8-chlorooctanoic acid ethyl ester mainly uses 6-oxo-8-chlorooctanoic acid ethyl es...

Claims

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Application Information

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IPC IPC(8): C07C67/31C07C69/675C02F9/10
CPCC02F1/001C02F1/04C02F9/00C02F2301/08C07C67/31C07C69/675
Inventor 钱振青邹振荣陆惠刚殷屹峰龚利锋
Owner JIANGSU TOHOPE PHARMA
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