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Preparation method for delta-decalactone

A technology of decanolactone and butyl-position, which is applied in the field of preparation of butyl-decalactone, can solve the problems of low total yield, long reaction route, and difficulty in industrial production, and achieve fewer steps, lower energy consumption, and simple operation Effect

Active Publication Date: 2014-12-10
HUAIAN WAN BANG SPICE IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the first method, the source of starting materials is difficult, serial production is not possible, or some reaction routes are too long, the total yield is low, and it is difficult to realize industrial production
In the second synthetic method, the method for obtaining the 2-pentylcyclopentanone intermediate is different. Among them, the method of obtaining 2-pentylcyclopentanone through aldol condensation and catalytic hydrogenation followed by oxidation and ring expansion is more suitable for industrialization. , but the step-by-step process is relatively complicated, and the number of washings in this process step is large, and the energy consumption is large

Method used

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  • Preparation method for delta-decalactone

Examples

Experimental program
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Effect test

Embodiment 1

[0019] (1) Synthesis of 2-pentylcyclopentanone

[0020] 890g 1.2% sodium hydroxide solution, 4.5gPd / C are added in the 5L reactor, N 2 Replace three times, raise the temperature to 80°C, pass in hydrogen to keep the pressure at 3.0Mpa, add dropwise a mixture of 540g (6.42mol) cyclopentanone and 450g (5.22mol) n-valeraldehyde, dropwise add in 4-5h, continue to keep warm after dropwise Pressure-holding reaction for 0.5h, the reaction is over, release the pressure, N 2 Replaced three times, filtered after cooling down to 60-70°C, recovered the catalyst and used it mechanically, separated the layers, and distilled the oil layer under reduced pressure to obtain 696g of 2-pentylcyclopentanone, the content of which was analyzed by GC was 95%.

[0021] (2) Synthesis of butyl-decalactone

[0022] Add 300g of toluene to the three-necked flask as a solvent, then add 696g of the above-mentioned 2-pentylcyclopentanone, and slowly add 1630g of 20% peroxyacetic acid dropwise under stirring...

Embodiment 2

[0024] (1) Synthesis of 2-pentylcyclopentanone

[0025] 1633g 0.5% potassium hydroxide solution and 40.8g Raney nickel were added to the 5L reactor, N 2 Substitute three times, raise the temperature to 100°C, pass in hydrogen to keep the pressure at 2.0Mpa, add dropwise a mixture of 540g (6.42mol) cyclopentanone and 276.5g (3.21mol) n-valeraldehyde, dropwise add in 4-5h, continue to Heat preservation and pressure reaction for 3h, the reaction is over, release the pressure, N 2 Replaced three times, filtered after cooling down to 60-70°C, recovered the catalyst and used it mechanically, separated the layers, and distilled the oil layer under reduced pressure to obtain 375.8 g of 2-pentylcyclopentanone, the content of which was analyzed by GC was 95%.

[0026] (2) Synthesis of butyl-decalactone

[0027] Add 751.6g of xylene as a solvent to the three-necked flask, then add 375.8g (2.44mol) of the above-mentioned 2-pentylcyclopentanone crude product, and slowly add 179.4g (2.68m...

Embodiment 3

[0029] (1) Synthesis of 2-pentylcyclopentanone

[0030] Add 334.8g 2.0% lithium hydroxide solution, 0.67gPd / C into the 2L reactor, N 2 Substitute three times, raise the temperature to 50°C, pass in hydrogen to keep the pressure at 5.0Mpa, add dropwise a mixture of 219.6g (2.61mol) cyclopentanone and 450g (5.22mol) n-pentanal, dropwise add in 4-5h, continue to Heat preservation and pressure reaction for 15min, the reaction is over, release the pressure, N 2 Replaced three times, filtered after cooling down to 60-70°C, recovered the catalyst and used it mechanically, separated the layers, and distilled the oil layer under reduced pressure to obtain 301.9 g of 2-pentylcyclopentanone, the content of which was analyzed by GC was 95%.

[0031] (2) Synthesis of butyl-decalactone

[0032] Add 15.1g of xylene as a solvent into the three-necked flask, then add 301.9g (1.96mol) of the above-mentioned 2-pentylcyclopentanone, and slowly add 406.1g (2.94mol) of peroxybenzoic acid under st...

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Abstract

The invention discloses a preparation method for delta-decalactone. The preparation method comprises the steps of serving cyclopentanone and n-valeraldehyde as original raw materials, simultaneously carrying out the two steps of aldol condensation and catalytic hydrogenation, synthesizing a 2-amyl cyclopentanone midbody by one-pot reaction, then carrying out oxidation ring enlargement, embedding an oxygen atom between keto and amyl, and synthesizing the delta-decalactone. The preparation method for the delta-decalactone is easy to do, simple and convenient to operate, and few in procedure. The product yield is improved by 3-4 percent compared with the method for preparation of the aldol condensation, the catalytic hydrogenation and oxidation step by step, only two steps of rectification are required, power consumption is reduced, and the preparation method for the delta-decalactone is applied to industrial production.

Description

technical field [0001] The invention relates to the field of perfume preparation technology, in particular to a preparation method of butyl decalactone. Background technique [0002] Butyl-decalactone, also known as 5-hydroxydecalactone, δ-decalactone, CAS No. 705-86-2, molecular formula C10H18O2, English name δ-Decalactone. Butydecalactone is an edible flavor that is allowed to be used in GB 2760-96. It has a strong and long-lasting creamy aroma. It is the main spice for making milk and cream flavors. It is also widely used for making coconut, strawberry, peach, etc. Fragrance, butyl decalactone is widely used in margarine, soft drinks, ice cream, candy, condiments and baked goods, and the market demand is great. [0003] There are two main routes for synthesizing butyl-decalactone: one is to synthesize δ-hydroxy acid through various routes, and then esterify and close the ring to obtain lactone; the other is to first synthesize 2-pentylcyclopentanone intermediate, and th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D309/30
Inventor 华建军刘晓涛张健安利民万猛续文文
Owner HUAIAN WAN BANG SPICE IND CO LTD
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