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Method for preparing 3- bornylene

A technology of bornyl and bornylidene, which is applied in the field of preparation of 3-borneol-2-butanol, and can solve the problem of unstable aroma quality, incomplete or over-reaction, and rough finished product. Woody aroma and other problems, reaching the end of the reaction is easy to control, avoiding incomplete reaction, and good aroma effect

Active Publication Date: 2008-02-20
格林生物科技股份有限公司
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  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the past preparation methods, simple hydrogen reduction (US4052341) was mostly used. This method is difficult to control the end point of the reaction, and the reaction is incomplete or over-reacted.
If the reaction is not complete, there will be a large amount of intermediate products (I and II below), and the presence of I and II in the finished product will cause the finished product to have a rough woody aroma; more by-products (III and IV below) will be produced during excessive reactions. ), III and IV do not have the characteristic aroma of sandalwood, so containing III and IV in the finished product will cause the sandalwood aroma of the finished product to weaken or even disappear. As a result, though the method has the characteristics of simple operation, the aroma quality of the prepared product is not Stablize

Method used

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  • Method for preparing 3- bornylene
  • Method for preparing 3- bornylene

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Experimental program
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Effect test

Embodiment 1

[0017] Embodiment 1: Preparation of 3-bornylidene-2-butanone

[0018] Add 350g (4.86mol) butanone, 800ml methyl alcohol, 350ml water and 30gKOH in the reaction kettle, add 200g (1.315mol) borneolenal under stirring, the reaction temperature is kept at room temperature, continue to react at room temperature for 8h after dropping, until The reaction is complete; the reactant is neutralized with acetic acid, and then washed with water until neutral. Remove solvent methanol and unreacted raw material butanone, distill under reduced pressure, collect fractions at 90-120°C / 2.5mmHg to obtain 243.8g of product with a yield of 90%.

Embodiment 2

[0019] Embodiment 2: the preparation of 3-borneolenyl-2-butanol crude product

[0020] Add 200g (0.97mol) 3-bornylidene-2-butanone, 160ml isopropanol, 0.06gKOH, 20g copper / chromium catalyst in the autoclave, the mixture is stirred and heated under 1~3MPa hydrogen pressure, and the temperature is maintained at Between 100°C and 200°C, react until gas chromatography shows that the content of raw materials or intermediates is 4.5%, stop the reaction, remove the solvent isopropanol in the reactant, distill under reduced pressure, and collect fractions at 103°C to 106°C / 133Pa, 185.4 g of product were obtained, a 91% yield.

Embodiment 3

[0021] Embodiment 3: the preparation of 3-borneolenyl-2-butanol crude product

[0022] Add 200g (0.97mol) 3-bornylidene-2-butanone in the autoclave, 180ml sec-butanol, 20g copper / chromium catalyst, 0.06gKOH, the mixture is stirred and heated under 1~3MPa hydrogen pressure, and the temperature is maintained at Between 110°C and 200°C, react until gas chromatography shows that the content of raw materials or intermediates is 4.3%, stop the reaction, remove the solvent sec-butanol in the reactant, distill under reduced pressure, collect fractions at 103°C to 106°C / 133Pa, 187 g of product was obtained, yield 91.5%.

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Abstract

The invention discloses a synthesis method of organic chemical industry field, in particular to the preparation method of 3-Campholenyl-2-Butanol. 3-campholenyl-2-Butanol is prepared by three continuous reaction steps: firstly, campholenic aldehyde is used as raw material to do an aldol condensation with butanone; secondly, 3-Subcampholenyl-2-Butanone, fatty alcohols with 2 to 4 carbon atoms, solid base and copper / chromium catalyst are reacted with each other; finally crude 3-Campholenyl-2-Butanol is added with solvent and reductant, and the finished product is prepared. The invention has the advantages of mild reaction condition, safe operation, and complete reaction, easy control of reaction endpoint as well as colorless and good fragrance of obtained sandalwood 210, etc. The invention avoids a technical obstacle of incomplete reaction or over-reduction which is existed in other technologies. The product of the invention can be widely used in makeup essence, soap essence, detergent essence and household essence.

Description

technical field [0001] The invention belongs to the synthesis field of organic chemical industry, and specifically refers to a preparation method of 3-borneolenyl-2-butanol. technical background [0002] 3-Campholenyl-2-butanol (3-Campholenyl-2-butanol, CAS accession number 65113-99-7; EINECS accession number 265-453-0) in my country is called sandalwood 210, also known as Sandalore; Sandasweet, Also known as 5-(2,2,3-trimethylcyclopent-3-enyl)-3-methylpentan-2-ol, it has a strong woody aroma, which resembles natural sandalwood, and is finely It is an important fragrance in chemical industry, widely used in cosmetic essence, soap essence, detergent essence and household essence. [0003] 3-Borneneyl-2-butanol is obtained by aldol condensation with butanone and then by catalytic hydrogenation (US4052341, CA97198416). [0004] [0005] The previous preparation method mostly adopts simple hydrogen reduction (US4052341), which is difficult to control the reaction end point, a...

Claims

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Application Information

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IPC IPC(8): C07C33/12C07C29/145
Inventor 胡建良王盈华黄旺生陈伟琴陆文聪
Owner 格林生物科技股份有限公司
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