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Preparation method for optically-pure citronellol

A citronellol and optical technology, applied in the field of preparation of optically pure citronellol, can solve the problems of no cost advantage, high equipment investment, complicated process and the like, and achieve the effect of improving chemical selectivity and stereoselectivity

Active Publication Date: 2016-02-17
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the raw material geraniol used is industrially obtained by selective hydrogenation of citral and purified by rectification, the product obtained through two-step hydrogenation has the disadvantages of complicated process and high equipment investment, and is not cost-effective. Advantage

Method used

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  • Preparation method for optically-pure citronellol
  • Preparation method for optically-pure citronellol
  • Preparation method for optically-pure citronellol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] 41.4mg1,1'-Bis[(2R,5R)-dimethylphospholane-1-yl]-ferrocene, 40.6mgRh(cod) 2 BF 4 , 16.58mg of potassium iodide was dissolved in 40mL of methanol, and transferred to a 100mL autoclave, 15.22g of neral (neral / geranial=99.1:0.9(mol), substrate / catalyst=1000(mol)) Inject into the autoclave, and adjust the pressure to 50 bar after passing through hydrogen to replace the gas in the autoclave three times. Stirring was started, and after reacting at 40° C. for 10 h, the conversion rate was measured by gas chromatography to be 99.9%, the product was L-citronellol, the yield was 99.8%, and the optical purity was 99ee%.

Embodiment 2

[0066] 41.4mg1,1'-Bis[(2R,5R)-dimethylphospholane-1-yl]-ferrocene, 40.6mgRh(cod) 2 BF 4 16.58 mg of potassium iodide was dissolved in 130 mL of methanol, and transferred to a 200 mL autoclave, with 15.22 g of neral (the ratio of neral / geranial isomers was 95:5 (mol), and the ratio of substrate / catalyst = 1000 (mol)) was injected into the autoclave, and the pressure in the autoclave was adjusted to 50 bar after being introduced into the hydrogen for three times. Stirring was started, and after reacting at 40° C. for 10 h, the conversion rate was measured by gas chromatography to be 99.9%, the product was L-citronellol, the yield was 99.8%, and the optical purity was 89ee%.

Embodiment 3

[0068] 41.4mg1,1'-Bis[(2S,5S)-dimethylphospholane-1-yl]-ferrocene, 40.6mgRh(cod) 2 BF 4 82.9 mg of potassium iodide was dissolved in 9.7 mL of methanol, and transferred to a 50 mL autoclave, 7.61 g of neral (the ratio of neral / geranial double bond isomers was 99.1:0.9 (mol), the substrate / catalyst ratio=500 (mol)) was injected into the autoclave, and the pressure was adjusted to 60 bar after passing through the hydrogen displacement autoclave for three times. Stirring was started, and after reacting at 40°C for 12 hours, the conversion rate was measured by gas chromatography to be 99.8%, the product was d-citronellol, the yield was 99.7%, and the optical purity was 90ee%.

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Abstract

The invention discloses a method for preparing optically-pure citronellol from neral or geranial. According to the method, an optically-pure transition metal catalyst is used, and neral or geranial is subjected to selective asymmetric hydrogenation for obtaining the optically-pure citronellol, the chemical selectivity reaches 98%-99.9%, and the stereoselectivity reaches 96%-99%, and the defects that raw materials are limited, the synthesis route is long, cost is high and the like in the process for synthesizing optically-pure citronellol in the prior art are solved.

Description

technical field [0001] The invention relates to a method for preparing optically pure citronellol, in particular to preparing optically pure citronellol through selective asymmetric hydrogenation of neral or geranial under the action of an optically pure transition metal catalyst, It belongs to the field of asymmetric catalysis. Background technique [0002] Citronellol has a fresh rose fragrance and is a very important spice raw material. It is usually used as a spice to be formulated into various floral essences and has a wide range of uses. Citronellol has two optical isomers, left-handed and right-handed. L-citronellol is usually called rose alcohol. It is mainly found in rose oil and essential oils of geranium plants. It has a rose-like special aroma, and the aroma of L-citronellol More elegant than d-citronellol, it is the main fragrance of rose flavor and can also be used in food flavor. Optically pure L-citronellol has higher economic value than racemic citronellol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/025C07C29/17
CPCC07C29/175C07C33/025
Inventor 董菁鲍元野张永振黎源陈建中张振锋张万斌
Owner WANHUA CHEM GRP CO LTD
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