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A kind of method that hydrogenation citral prepares citronellol

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: 2011-12-28
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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  • A kind of method that hydrogenation citral prepares citronellol
  • A kind of method that hydrogenation citral prepares citronellol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Metal cobalt, nickel, molybdenum, and aluminum are fused at high temperature in proportions of 25%, 30%, 5%, and 40%, respectively, the alloy is cooled to room temperature, crushed, and alloy particles of 400 meshes or more and 50 meshes are screened. Prepare 500 g of sodium hydroxide solution with 20% concentration, boil, slowly add 100 g of alloy particles, continue to boil for 4 hours, and cool. Pour the gray upper layer of turbid liquid, add clean 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 catalyst is stored under the water seal liquid surface for later use.

[0031] In a 500ml hydrogenation reaction autoclave, 58g of clear water, 2.0g of dipropylamine, 5g of M2 type catalyst with moisture and water, 25g of n-hexane, and 60g of citral (content 96%, the remaining 4% are impurities) were added successively. Seal the autoclave, replace wit...

Embodiment 2

[0034] Metal cobalt, nickel, molybdenum, and aluminum are fused at high temperature in proportions of 0.8%, 40%, 7%, and 52.2% respectively, the alloy is cooled to room temperature, crushed, and alloy particles of 400 meshes or more and 50 meshes are screened. Prepare 500 g of sodium hydroxide solution with 20% concentration, boil, slowly add 100 g of alloy particles, continue to boil for 4 hours, and cool. Pour the gray upper layer of turbid liquid, add clean 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 surface for later use.

[0035] In a 500ml hydrogenation reaction autoclave, 14g of clear water, 0.08g of n-heptylamine, 15g of M2 type catalyst moistened with water, 70g of benzene, and 50g of citral (content 96%, the remaining 4% are impurities) are added successively. Seal the autoclave, replace with ni...

Embodiment 3

[0038] Metal cobalt, nickel, molybdenum, and aluminum are fused at high temperature in proportions of 20%, 40%, 3.5%, and 36.5% respectively, the alloy is cooled to room temperature, crushed, and alloy particles of 400 meshes or more and 50 meshes are screened. Prepare 500 g of sodium hydroxide solution with 20% concentration, boil, slowly add 100 g of alloy particles, continue to boil for 4 hours, and cool. Pour the gray upper layer of turbid liquid, add clean 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 surface for later use.

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

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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 obtaining citronellol by directly reducing citral using a batch hydrogenation method. Background technique [0002] Citronellol is naturally present in many essential oils such as citronella oil, geraniol oil and rose oil. It has a fresh rose and bay leaf-like aroma and is widely used in perfume fragrances, soaps and cosmetic fragrance formulations. When formulating floral flavors, the dosage can be as high as 50%. [0003] Citronellol can be obtained by natural extraction and chemical synthesis. At present, there are many manufacturers of synthetic citronellol at home and abroad. Their production methods are mainly divided into two categories: one type uses citral or citronellal as raw materials to obtain citronellol by direct selective reduction, and the other type uses dihydrolaurel. Alkene is used as raw material to obtain citronellol through addition-hydrolysis m...

Claims

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Application Information

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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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