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Method for preparing citronellol by using hydrogenating citral

A technology of citral and citronellol, applied in chemical instruments and methods, preparation of hydroxyl compounds, preparation of organic compounds, etc., can solve problems such as low conversion rate and selectivity, low reaction selectivity, and great environmental hazards of chromium. Achieve the effect of simple separation, simple and flexible operation, and low threshold for industrialization

Active Publication Date: 2013-09-18
ZHEJIANG NHU CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The shortcoming of this method is: 1, use the heavy metal composition that chromium, barium, copper etc. have serious harm to environment, three wastes problem is serious
2. Another problem is that the selectivity is low (about 90%), which is due to the high temperature of the reaction
But the shortcoming that this method exists: 1, reaction selectivity is relatively low
2. The use of chromium is more harmful to the environment
The problem of this method is that conversion rate and selectivity are lower (up to 93%), and the boiling point of raw material citral and product citronellol is close so that it is difficult to rectify and separate to obtain citronellol
[0013] The above literatures describe several catalysts and production methods with high selectivity, but the problems of high cost and low operability have not been completely solved.

Method used

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  • Method for preparing citronellol by using hydrogenating citral
  • Method for preparing citronellol by using hydrogenating citral

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Metal cobalt, nickel, molybdenum, and aluminum are fused at high temperature according to the proportions of 25%, 30%, 5%, and 40%, respectively, the alloy is cooled to room temperature, crushed, and the alloy particles of 400 mesh or more and 50 mesh or less are screened. Prepare 500 g of sodium hydroxide solution with a concentration of 20%, boil it, slowly add 100 g of alloy particles, continue to boil for 4 hours, and cool. Pour off the gray upper layer of turbid liquid, add water and wash it repeatedly at room temperature for 3 times. After standing still, the liquid layer is clear and transparent, and the pH value is less than 10. The prepared M2 type catalyst is stored under the water seal liquid level for subsequent use.

[0031] Add 58g of clear water, 2.0g of dipropylamine, 5g of wet M2 type catalyst, 25g of n-hexane, 60g of citral (content 96%, all the other 4% are impurities) in the hydrogenation reaction autoclave of 500ml successively. Seal the autoclave, r...

Embodiment 2

[0034] Metal cobalt, nickel, molybdenum, and aluminum are fused at a high temperature according to the proportions of 0.8%, 40%, 7%, and 52.2%, respectively, the alloy is cooled to room temperature, crushed, and the alloy particles of 400 mesh or more and 50 mesh or less are screened. Prepare 500 g of sodium hydroxide solution with a concentration of 20%, boil it, slowly add 100 g of alloy particles, continue to boil for 4 hours, and cool. Pour off the gray upper layer of turbid liquid, add water and wash it repeatedly at room temperature for 3 times. After standing still, the liquid layer is clear and transparent, and the pH value is less than 10. The prepared catalyst is stored under the water seal liquid level for subsequent use.

[0035] In a 500ml hydrogenation reaction autoclave, 14g of clear water, 0.08g of n-heptylamine, 15g of wet M2 type catalyst, 70g of benzene, and 50g of citral (96% of content, and 4% of impurities) were successively added into the hydrogenation r...

Embodiment 3

[0038] Metal cobalt, nickel, molybdenum, and aluminum are fused at high temperature according to the proportions of 20%, 40%, 3.5%, and 36.5%, respectively, the alloy is cooled to room temperature, crushed, and the alloy particles of 400 mesh or more and 50 mesh or less are screened. Prepare 500 g of sodium hydroxide solution with a concentration of 20%, boil it, slowly add 100 g of alloy particles, continue to boil for 4 hours, and cool. Pour off the gray upper layer of turbid liquid, add water and wash it repeatedly at room temperature for 3 times. After standing still, the liquid layer is clear and transparent, and the pH value is less than 10. The prepared catalyst is stored under the water seal liquid level for subsequent use.

[0039] In a 500ml hydrogenation reaction autoclave, 18g of clear water, 0.9g of diisohexylamine, 20g of wet M2 type catalyst, 75g of petroleum ether, and 47g of citral (content 96% and the remaining 4% are impurities) were successively added into ...

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Abstract

The invention relates to a method for preparing citronellol by directly reducing citral by an intermittent hydrogenation method. Multiple kinds of catalysts with high selectivity and production methods are disclosed in the prior art, but the problems of high cost, low operability and the like are not completely solved. In a reaction system, citral is used as a raw material and an M2 metal-skeleton-shaped alloy solid is used as a catalyst; the reaction system also comprises an aqueous solution of amine substances and a non-polar solvent; and the citral is selectively reduced to a citronellol crude product by hydrogen by the intermittent hydrogenation method, and the citronellol crude product is rectified under reduced pressure to form a citronellol fine product. In the method, the hydrogen, oil, water and catalyst four-phase reaction system is established, and the cheap M2 catalyst achieves high selectivity which can be achieved by a noble metal catalyst by adding the non-polar solventand the aqueous solution of amine substances and combining the molecular structure characteristics of citral; and reaction conversion rate reaches 99.3 percent, and reaction selectivity is over 96 percent.

Description

technical field [0001] The invention relates to the preparation of organic matter, in particular to a method for directly reducing citral to obtain citronellol by a batch hydrogenation method. Background technique [0002] Citronellol occurs naturally in many essential oils, including citronella, geranium, rose, and many others. It has a fresh rose and bay leaf-like aroma, and is widely used in perfume essence, soap and cosmetic essence formulations. In the preparation of floral fragrance, its dosage can be as high as 50%. [0003] There are two ways to obtain citronellol: natural extraction and chemical synthesis. At present, there are many manufacturers of synthetic citronellol at home and abroad, and their production methods are mainly divided into two categories: one is to obtain citronellol by direct selective reduction of citral or citronellal as raw material, and the other is to obtain citronellol by dihydrolauric Citronellol can be obtained by using alkenes as raw...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C33/025C07C29/141B01J23/883B01J35/10
Inventor 季根忠陈江陈海烽徐盛阮文兵郑常军
Owner ZHEJIANG NHU CO LTD
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