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Method for preparing geranyl acetate under catalysis of acidic functionalized ionic liquid

A technology of geranyl acetate and ionic liquids, which is applied in the preparation of carboxylic acid esters, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of non-recyclability, environmental pollution, etc., and achieve less side reactions, environmental friendliness, Simple operation effect

Inactive Publication Date: 2017-07-04
SHANGYU NHU BIOCHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that the use of chromium derivatives as catalysts will pollute the environment, while acetic anhydride is an esterification reagent and cannot be recycled.

Method used

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  • Method for preparing geranyl acetate under catalysis of acidic functionalized ionic liquid
  • Method for preparing geranyl acetate under catalysis of acidic functionalized ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～5

[0029] Take 14.48g of acetic acid and 30.84g of geraniol, mix them evenly and add them into a three-necked flask, add 5g of acidic functionalized ionic liquid catalyst I, heat and reflux and stir, use a water separator to separate water, react at 110°C for 2h, cool it with diethyl ether Extraction, the raffinate is the recovered catalyst, ether is recovered under reduced pressure, and geranyl acetate is obtained by distillation. The yield is shown in Table 1.

[0030] The reaction condition and reaction result of table 1 embodiment 1~5

[0031] Example temperature reflex yield purity 1 90℃ 84％ 98.2％ 2 100℃ 95％ 98.4％ 3 110℃ 97％ 99.1％ 4 120℃ 92％ 98.0％ 5 130℃ 91％ 97.5％

[0032] Wherein, the preparation method of acidic functionalized ionic liquid catalyst I is as follows:

[0033] Mix 1,3-propane sultone and methylethylbutylamine at a molar ratio of 1:1, react at 40°C for 10 hours to obtain a white solid, wash and dry the wh...

Embodiment 6～9

[0035] Catalyst recycling: the catalyst in Example 3 was not treated in any way, and 14.48g of acetic acid and 30.84g of geraniol were added, reacted at 110°C for 2h, extracted with ether after cooling, recovered ether, and distilled under reduced pressure to obtain acetic acid aroma. Leaf ester, the yield is shown in Table 2.

[0036] The catalyst application process is as follows:

[0037] The reaction conditions and reaction result of embodiment 6~9

[0038] Example repeat times yield 3 0 97.0％ 6 1 96.8％ 7 2 95.9％ 8 3 95.5％ 9 4 95.2％

Embodiment 10～11

[0040] Different acidic ionic liquid catalysts were used to conduct experiments under the same other conditions. The experimental method was consistent with that of Example 3. The yield and content data are shown in the table below.

[0041] Catalyst type and reaction result of embodiment 10~11

[0042] Example catalyst yield content 10 Ionic Liquid II 95.4％ 97.5％ 11 Ionic liquid III 92.4％ 96％

[0043] The preparation method of ionic liquid II is as follows:

[0044] Mix 1,3-propane sultone and triethylamine at a molar ratio of 1:1, react at 40°C for 10 hours to obtain a white solid, wash and dry the white solid with ethyl acetate. Take 1 equivalent of the above-mentioned white solid and slowly add it to a reaction kettle containing 1 molar equivalent of p-toluenesulfonic acid under an ice-water bath, stir for 2 hours, then raise the temperature to 80°C for 8 hours, wash with ethyl acetate, and distill under reduced pressure to remove Ethy...

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Abstract

The invention discloses a method for preparing geranyl acetate under the catalysis of acidic functionalized ionic liquid. The method comprises the following steps: subjecting acetic acid and geraniol to esterification under the catalysis of the acidic functionalized ionic liquid; and after complete reaction, subjecting a reaction solution to after-treatment so as to obtain geranyl acetate. The structure of the acidic functionalized ionic liquid is as shown in a formula (II), i.e., [X(CH<2>)<n>SO<3>H]<+>Y<->. In the formula (II), X is R<1>(R<2>)(R<3>)N-, and R<1>, R<2> and R<3> are independently selected from C1-C5 alkyl groups; n is an integer in a range of 1 to 5; and Y<-> is a hydrosulfate radical, a sulfonate radical, a methanesulfonate radical, a trifluoromethanesulfonate radical, a benzenesulfonate radical or a p-toluenesulfonate radical. The method provided by the invention is high in conversion rate, few in side reactions, high in product yield and purity and simple in after-treatment, and has important industrial application value.

Description

technical field [0001] The invention belongs to the field of preparation of flavors and fragrances, and in particular relates to a method for preparing geranyl acetate by catalyzing an acidic functionalized ionic liquid. Background technique [0002] Geranyl acetate, whose structure is shown in formula (I), is also known as geranyl acetate. It is a colorless to light yellow liquid with aroma of rose and lavender. It can be used to prepare rose, orange blossom, osmanthus, etc. essence. [0003] [0004] Industrially, geranyl acetate is prepared by reacting acetic anhydride and geranyl ester in the presence of concentrated sulfuric acid. This traditional method has many disadvantages. For example, concentrated sulfuric acid has the functions of esterification, dehydration and oxidation at the same time, leading to a series of side reactions, which brings difficulties to the purification of products; the post-treatment process is complicated and the environment is seriously...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/145C07C69/007B01J31/02
CPCB01J31/0278B01J2231/49C07C67/08C07C69/145C07C69/007
Inventor 田金金牛少凤管敏虾刘祥洪李小军姜恒菊刘阳
Owner SHANGYU NHU BIOCHEM IND
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