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Method for preparing linalyl acetate from dehydrolinalool

A technology of dehydrolinalool and linalyl acetate, which is applied to the preparation of carboxylic acid esters, chemical instruments and methods, and the preparation of organic compounds, and can solve the problems of difficult to manufacture high-grade fragrances, long time required for esterification reaction, Difficulty in refining hydrogenation products, etc., to achieve ideal conversion rate and selectivity, high quality, and convenient removal

Inactive Publication Date: 2008-07-02
SINOPEC SHANGHAI PETROCHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The hydrogenation process of the method described in the above-mentioned U.S. Patent US 2,797,235 has adopted a hydrogenation catalyst similar to Lindlar catalyst. It not only needs to add quinoline as a catalyst accelerator, but also adds a large amount of cyclohexane as a solvent for the hydrogenation reaction, so In addition to the long time required for the esterification reaction, the method is also very difficult to refine the hydrogenation product, and it is difficult to meet the requirements for the manufacture of high-grade fragrances.

Method used

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  • Method for preparing linalyl acetate from dehydrolinalool
  • Method for preparing linalyl acetate from dehydrolinalool
  • Method for preparing linalyl acetate from dehydrolinalool

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～11

[0036] A 500ml three-necked flask with a stirring device is placed in a water bath, 152g of dehydrolinalool is added, nitrogen is purged for 20min, the temperature is raised to the reaction temperature with stirring, and acetic anhydride is dropped in according to the required molar ratio, and the The required amount of catalyst sulfosalicylic acid starts the reaction and is maintained for the required reaction time to complete the reaction. The product is cooled, washed with water, and statically layered to separate the oil and water phases until the oil phase material is neutral, and the oil phase material is taken to obtain the esterification product dehydrolinalyl acetate.

[0037] The specific esterification reaction conditions of Examples 1-11 are shown in Table 1, and the esterification reaction results are shown in Table 2.

[0038] Table 1.

[0039] temperature reflex

[0040] Note: 1) catalyst consumption is the weight percent of raw material feeding to...

Embodiment 12～23

[0046] Preparation of hydrogenation catalyst:

[0047] The starting materials of each active component are: palladium nitrate solution is used for Pd; lead nitrate solution is used for Pb; bismuth nitrate solution is used for Bi in component A, and zinc nitrate solution is used for Zn.

[0048] The above-mentioned starting materials are prepared into an impregnation solution according to the required ratio; a certain amount of calcium carbonate carrier is placed in the impregnation solution and impregnated to obtain a catalyst precursor. The amount of the impregnation solution is 95% to 110% of the water absorption value of the carrier. and 70°C for 1 hour; the catalyst precursor was dried and then roasted at 280°C for 5 hours; the roasted catalyst precursor was reduced with hydrazine hydrate; it was washed several times until the pH value in the washing liquid was close to Neutral, and finally dried at 75°C to obtain the finished catalyst for future use.

[0049] The active ...

Embodiment 24～31

[0058] Using the hydrogenation catalyst of Example 19, the hydrogenation reaction conditions were changed. The changed reaction conditions are shown in Table 5, and the rest are the same as in Examples 12-23. The results are shown in Table 6.

[0059] table 5.

[0060] temperature reflex

(℃)

hydrogen pressure

(Mpa)

Reaction time

(min)

Catalyst accounts for the reaction solution

(wt%)

Example 24

30

1.5

100

1.0

Example 25

20

3.0

240

0.2

Example 26

50

2.5

110

0.2

Example 27

80

2.5

60

5.0

Example 28

50

3.5

120

0.01

Example 29

90

5.5

90

2.0

Example 30

65

2.0

180

0.5

Example 31

150

10

30

0.1

[0061] Table 6.

[0062] Conversion rates

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Abstract

The invention relates to a method for preparing linalyl acetate from dehydrolinalool. The method comprises esterification between dehydrolinalool and acetic anhydride is carried out in the presence of catalyst. The catalyst is sulfosalicylic acid, dosage of which is 0.05-5wt percent of total amount of the raw material provided. Product of the esterification is washed till oil phase material is neutral, and the dehydrolinalyl acetate is obtained. The dehydrolinalyl acetate undertakes hydrogenation reaction with hydrogen in the presence of catalyst ; the catalyst adopts calcium carbonate as a carrier; active components loaded contain Pd, Pb and A component, A is Bi or Zn or mixture of Bi and Zn, total content of Pd and Pb is 0.1-4.0wt percent, mass ratio of Pd and Pb is (5-1):1, content of A is 0.5-3.0wt percent and dosage of the catalyst accounting for 0.01-5.0wt percent of reaction liquid. The catalyst is removed from the product of the hydrogenation reaction through solid and liquid separation, and linalyl acetate is obtained by rectifying and refining. The invention has the advantages that the catalyst of esterification and hydrogenation reaction has higher activity, and conversion and selectivity are ideal.

Description

technical field [0001] The present invention relates to a preparation method of acid-containing linalyl ester, in particular to a method in which dehydrolinalyl alcohol is subjected to an esterification reaction in the presence of an acidic catalyst to generate dehydrolinalyl acetate, and then hydrogenated to prepare linalyl acetate . Background technique [0002] Dehydrolinalyl acetate is an important fine chemical intermediate for the preparation of fragrances, and can be used to produce fine chemical products such as citral and ionone. Linalyl acetate can also be obtained through hydrogenation reaction of dehydrolinalyl acetate. Linalyl acetate is one of the main components of lavender oil. It has an elegant fragrance, similar to bergamot oil and lavender oil. An important raw material for spices or essences. In the prior art, linalyl acetate is mostly prepared by esterification of linalool and acetic anhydride, because linalool can be obtained from isoprene, the separa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C67/303C07C69/145
Inventor 郭世卓安源朱岳中华建英
Owner SINOPEC SHANGHAI PETROCHEMICAL CO LTD
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