A kind of synthetic method of pseudoionone

A pseudo-ionone and synthetic method technology, applied in the field of synthesis of pseudo-ionone, can solve the problems of long time, large amount of acetone, poor atom economy, etc., and achieve high production efficiency, few reaction steps and high selectivity Effect

Active Publication Date: 2021-06-01
ZHEJIANG NHU CO LTD +1
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Problems solved by technology

[0005] Chinese patents CN201180035713.6, CN201510936416.9 and CN201210581435.0 respectively introduce the method of preparing pseudo-ionone by catalyzing condensation of citral and acetone with lanthanum oxide, solid alkali and liquid alkali. Although the route is simple, the cost of raw material citral is high , a large amount of acetone, high energy consumption for recycling, and difficulty in the treatment of three wastes, etc.
Chinese patent CN201210580431.0 proposes a method for synthesizing pseudoionone and methyl pseudoionone with dehydrolinalool and acetoacetate under the action of aluminum isopropoxide, but there is a large amount of by-product carbon dioxide produced during the reaction , defects such as poor atom economy; in comparison, method (3) has good atom economy, high yield, less pollution, environmental friendliness, and very broad prospects for industrial application
[0006] Saucy et al. described in U.S. Patent No. 3,029,287 that dehydrolinalool and 2-methoxypropene were reacted under the action of p-toluenesulfonic acid for 15 hours to obtain the crude allenone, and then added an alcohol solution of alkali for isomerization treatment. , finally get the pseudo-ionone crude product, the reaction yield is low and the time is long
[0007] Chinese patent CN00129921.2 describes the use of aliphatic sulfonic acid or sulfonate to catalyze the Saucy-Marbet reaction and isomerization of dehydrolinalool and 2-methoxypropylene to obtain pseudo-ionone, with a yield of 92%, but The reaction time is long, more than 6 hours, and a large amount of solvent needs to be added, resulting in cumbersome post-processing and high recovery energy consumption

Method used

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  • A kind of synthetic method of pseudoionone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Dehydrolinalool, 2-methoxypropene and 2,2-dimethoxypropane solution of methanesulfonic acid with a mass content of 0.133% (molar ratio is 1:2.3:0.001) were prepared at 0.057ml / min, The flow rates of 0.070ml / min and 0.049ml / min are pumped into the microchannel reactor at 160°C (the pipe length is 28m*5, the inner diameter is 0.2*0.2mm, the pressure is about 0.8MPa, and the feed port (II) is set at 1 / 2 locations). The sample was taken from the sampling port of the pipeline, and through gas analysis, it was confirmed that the products were allenone and pseudopurple isomers. The collected solution was analyzed by gas phase, and the conversion rate of dehydrolinalool was 99.5%, and the selectivity for the products diketenone and pseudopurple was 96.5%.

[0030] Pass into the 2,2-dimethoxypropane solution (the mol ratio of dehydrolinalool and phosphoric acid is 1:0.002) of the phosphoric acid of 0.242% from the feed port (II), flow is 0.039ml / min. The collected solution ...

Embodiment 2

[0032] Dehydrolinalool, 2-methoxypropene and 2,2-dimethoxypropane solution of phosphoric acid with a mass fraction of 0.242% (molar ratio is 1:2.3:0.002), respectively at 0.057ml / min, 0.070 The flow rate of ml / min and 0.049ml / min is pumped into the microchannel reactor at 160°C (the tube length of the microchannel reactor is 28m*5, the inner diameter of the tube is 0.2*0.2mm, and the pressure inside the tube is maintained at 0.8MPa, Feed inlet (II) is set at 3 / 4).

[0033] Pass into the 2,2-dimethoxypropane solution (the mol ratio of dehydrolinalool and phosphoric acid is 1:0.002) of the phosphoric acid of 0.242% from the feed port (II), flow is 0.039ml / min. The collected solution was a yellowish brown transparent liquid, and the gas phase analysis was performed on the material within 1 hour. The conversion rate of dehydrolinalool was 66.3%, and the selectivity to the product pseudoionone was 79.6%. The measurement results are listed in Table 1.

Embodiment 3-17

[0035]With reference to the preparation method of Example 1, change the conditions such as the type and amount of the SM reaction catalyst, the type and amount of the isomerization catalyst, the reaction temperature, the residence time, the molar equivalent ratio of dehydrolinalool and 2-methoxypropene in the reaction In addition, other reaction conditions and detection methods were the same as in Example 1, and pseudoionone was prepared.

[0036] Catalyst equivalent is the ratio of the molar weight of catalyst and the molar weight of dehydrolinalool, and result is as shown in table 1:

[0037] Table 1 is the reaction condition and the result of embodiment 1-17

[0038]

[0039]

[0040] As can be seen from the test results of the examples in Table 1 above, in the examples that meet the conditions defined in the present application, the selectivity of the product and the conversion rate of the raw material are high, and the reaction can be completed quickly. In Example ...

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Abstract

The invention relates to a synthetic method of pseudoionone, which comprises the steps of sequentially performing Saucy-Marbet reaction and isomerization reaction in a microchannel reactor with dehydrolinalool and 2-methoxypropylene to prepare pseudoionone. Pseudo-ionone was prepared from dehydrolinalool through Saucy-Marbet reaction and isomerization reaction in a microchannel reactor, which realized the continuous production of pseudo-ionone with high efficiency, few reaction steps and high yield. High, high selectivity, less pollution, in line with the development concept of green chemical industry.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a synthetic method of pseudoionone. Background technique [0002] Pseudoionone (6,10-dimethyl-3,5,9-undecane-trien-2-one) is an important intermediate for the synthesis of vitamin A, vitamin E, carotene and spice compounds. It is widely used in flavors and fragrances, food additives, and pharmaceutical industries. [0003] At present, the main methods of its synthesis are: (1) citral is condensed with acetone Aldol under alkaline conditions; (2) dehydrolinalool and acetoacetate are reacted by Carroll under the action of a catalyst, and then undergo isomerization (3) Dehydrolinalool and 2-alkoxypropylene are generated by Saucy-Marbet reaction and isomerization under the action of acid. The reaction equations of these three methods are as follows: [0004] [0005] Chinese patents CN201180035713.6, CN201510936416.9 and CN201210581435.0 respectively introduce the meth...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/67C07C49/203
CPCC07C45/51C07C45/67C07C49/203
Inventor 王旭明曾瑞杰王钰王晓军白发明刘晓庆于明
Owner ZHEJIANG NHU CO LTD
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