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Process for producing salicylic esters

A manufacturing method and technology of salicylate, applied in chemical instruments and methods, preparation of organic compounds, reaction preparation of ester groups and hydroxyl groups, etc., can solve the problems of easy deactivation, difficult catalyst reuse, increased viscosity of distillation residue, etc. question

Inactive Publication Date: 2006-03-15
KAO CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the titanium-based catalyst is easily deactivated in the reaction system, it is difficult to realize the reuse of the catalyst, and the production cost cannot be avoided, and the viscosity of the distillation residue after the reaction increases, and operations such as precipitation of solids in the distillation residue will occur. sexual problems

Method used

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  • Process for producing salicylic esters
  • Process for producing salicylic esters
  • Process for producing salicylic esters

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] 228.50 g (1.5 moles) of methyl salicylate and 165.24 g (1.65 moles) of cyclohexanol were added to a four-necked flask made of glass, and 2.65 g (0.0075 moles / mole) of di-n-butyl tin diacetate was added under stirring. 0.5 mol% relative to methyl salicylate). Under normal pressure, the temperature was raised slowly from 140°C to 170°C, during which free methanol was distilled out of the reaction system. After the temperature of the reaction liquid reached 170°C, the pressure was reduced to 93.3kPa, and the temperature was kept at 160-170°C by heating, and the reaction was continued for 2 hours while continuing to distill free methanol. The cyclohexyl salicylate in the reaction-finished solution was quantitatively analyzed by gas chromatography, and the reaction yield was 86.7%.

[0060] Use a distillation column with 10 plates to distill the reaction end liquid, first distill off 9.27g of unreacted cyclohexanol at 1.3kPa, 95-145°C, and a circulation ratio of 1, and then...

Embodiment 2

[0063]Only 228.58 g (1.5 moles) of methyl salicylate and 165.59 g (1.65 moles) of cyclohexanol were added to 18.26 g of the distillation residue obtained in Example 1, and the temperature was slowly raised from 140° C. to 170° C. while stirring, Free methanol was distilled off. After the liquid temperature reaches 170°C, reduce the pressure to 93.3kPa, heat and keep at 160-170°C, and continue to distill free methanol while reacting for about 2 hours. The cyclohexyl salicylate in the reaction-finished liquid was quantitatively analyzed by gas chromatography, and the amount of cyclohexyl salicylate in the distillation residue was subtracted to determine the reaction yield, which was 88.8%.

Embodiment 3

[0065] 228.20 g (1.5 moles) of methyl salicylate and 166.49 g (1.66 moles) of cis-3-hexenol were added to a four-necked glass flask, and 2.64 di-n-butyl tin diacetate was added under stirring. g (0.0075 mol / 0.50 mol% relative to methyl salicylate). Under normal pressure, the temperature was raised slowly from 140°C to 170°C, during which free methanol was distilled out of the reaction system. After the temperature of the reaction liquid reached 170°C, the pressure was reduced to 93.3kPa, and the temperature was kept at 160-170°C by heating, and the reaction was continued for 2 hours while continuing to distill free methanol. Quantitative analysis of cis-3-hexenyl salicylate in the reaction-finished liquid was carried out by gas chromatography, and the reaction yield was 92.2%.

[0066] Use a distillation column with 10 plates to distill the reaction end liquid, first distill off 18.24 g of unreacted cis-3-hexenol at 1.3kPa, 87-130°C, and a circulation ratio of 1, and then dis...

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Abstract

There is provided a noble process for producing a salicylic ester for perfumes which comprises the step of transesterifying a salicylic lower alkyl ester with an alcohol having at least one carbon atom which is located adjacent to a hydroxyl-bonded carbon atom and has one or more hydrogen atoms bonded thereto, in the presence of a tin-based catalyst. The process of the present invention enables the salicylic ester to be produced at a high yield and is free from handling problems such as precipitation of solids in a distillation residue obtained after the reaction, and the catalyst used therein is reusable.

Description

technical field [0001] The present invention relates to a method for producing salicylate, and more specifically, to an improved method for producing salicylate used as a fragrance ingredient. Background technique [0002] Salicylates can be used in a variety of applications, one of which is as a fragrance. For example, methyl salicylate, ethyl salicylate, butyl salicylate, isobutyl salicylate, amyl salicylate, isopentyl salicylate, hexyl salicylate, cis salicylate -3-Hexenyl ester, cyclohexyl salicylate, phenethyl salicylate, etc. are put into practical use as fragrances. [0003] As the production method of salicylic acid ester, the production method of the direct esterification reaction of salicylic acid and alcohol, and the production method of transesterification reaction of salicylic acid lower alkyl esters, such as methyl salicylate, and alcohol are known. [0004] Salicylic acid lower alkyl esters, such as methyl salicylate and ethyl salicylate, are easily esterifi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/84C07C67/03
CPCB01J31/4015B01J31/122C07C67/03B01J2531/42C07C2101/14Y02P20/584C07C2601/14C07C69/84
Inventor 上原武文大野哲小刀慎司田中成佳
Owner KAO CORP
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