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A kind of preparation method and application of solid condensation catalyst

A condensation catalyst and solid technology, applied in the field of spices, can solve the problems of low conversion rate of raw materials, low product selectivity, large amount of waste water, etc., and achieve the effects of high catalytic activity, high product purity and energy saving

Active Publication Date: 2021-05-04
SHANDONG NHU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The problem to be solved in the present invention is aimed at the shortcomings such as low raw material conversion rate, low product selectivity and large amount of waste water in the preparation process of α-pentyl cinnamaldehyde and α-hexyl cinnamaldehyde in the prior art; a kind of solid condensation catalyst is provided, Reduce the amount of waste water, reduce post-processing steps, and save resources; when the ratio of benzaldehyde to n-heptanal or n-octylaldehyde is less than 5, the selectivity of condensation is increased to more than 90%, and the self-condensation of n-heptanal or n-octylaldehyde is reduced The generation of by-products reduces the difficulty of separation and improves the purity of α-pentyl cinnamaldehyde or α-hexyl cinnamaldehyde in the product. The ratio of E-type isomer and Z-type isomer in the product can reach 97:3~99: 1

Method used

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  • A kind of preparation method and application of solid condensation catalyst
  • A kind of preparation method and application of solid condensation catalyst
  • A kind of preparation method and application of solid condensation catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 1) Preparation of N-Cbz-4-(2-triethoxysilylethylcarbamoyl)oxa-L-proline benzyl ester IX

[0032] Triethoxysilylethyl isocyanate VII 23.3g and N-Cbz-4-hydroxy-L-proline benzyl ester Ⅷ 35.5g in dichloromethane solvent; stirred and reacted at 10°C for 15h, evaporated the solvent to dryness Purified directly for next step reaction;

[0033] 2) Preparation of 4-(2-triethoxysilylethylcarbamoyl)oxa-L-proline X

[0034] Step 1) Add 59 g of product IX to a mixed solution of 200 ml of ethanol and 70 ml of cyclohexane, add 59 mg of palladium carbon, feed hydrogen gas to 1.0 MPa, heat up to 100 ° C for 2 hours, cool down and filter to remove the catalyst, and distill off the solvent to obtain a light yellow color The solid X was directly used in the next reaction without purification.

[0035] 3) Preparation of condensation catalyst

[0036] Add 500ml of toluene to 30g of MCM-41 and stir; Step 2) Dissolve X3g of the product in 100ml of toluene, then add it to the suspension of MCM...

Embodiment 2

[0040] 1) Preparation of N-Cbz-4-(2-triethoxysilylethylcarbamoyl)oxa-L-proline benzyl ester IX

[0041] 11.8 g of triethoxysilylethyl isocyanate VII and 17.8 g of N-Cbz-4-hydroxy-L-proline benzyl ester VIII in toluene as a solvent. React at 70°C for 4 hours, evaporate the solvent to dryness and use it directly for the next reaction;

[0042] 2) Preparation of 4-(2-triethoxysilylethylcarbamoyl)oxa-L-proline X

[0043] Step 1) Add 72g of product IX to a mixed solution of 210ml of methanol and 80ml of toluene, add 59mg of Raney nickel, feed hydrogen to 1.6MPa, heat up to 60°C and react for 4 hours, cool down and filter to remove the catalyst, distill off the solvent to obtain a light yellow solid X, directly used in the next reaction without purification.

[0044] 3) Preparation of condensation catalyst

[0045] Add 500ml of toluene to 30g of MCM-41 and stir; Step 2) Dissolve X3g of the product in 100ml of toluene, then add it to the suspension of MCM-41 under stirring, heat a...

Embodiment 3

[0049] 1) Preparation of N-Cbz-4-(2-triethoxysilylethylcarbamoyl)oxa-L-proline benzyl ester IX

[0050] Triethoxysilylethyl isocyanate VII 11.8 g and N-Cbz-4-hydroxy-L-proline benzyl ester VIII 17.8 g in the solvent cyclohexane. React at 50°C for 7h, evaporate the solvent to dryness and directly use in the next reaction;

[0051] 2) Preparation of 4-(2-triethoxysilylethylcarbamoyl)oxa-L-proline X

[0052] Step 1) Add 100 g of product IX to a mixed solution of 350 ml of ethanol and 120 ml of toluene, add 100 mg of palladium carbon, feed hydrogen gas to 0.8 MPa, heat up to 75 ° C for 2 hours, cool down and filter to remove the catalyst, and distill off the solvent to obtain a light yellow solid X , directly used in the next reaction without purification.

[0053] 3) Preparation of condensation catalyst

[0054] Add 500ml of toluene to 30g of MCM-41 and stir; Step 2) Dissolve X3g of the product in 100ml of toluene, then add it to the suspension of MCM-41 under stirring, heat a...

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Abstract

The invention belongs to the technical field of spices, and specifically relates to a preparation method and application of a solid condensation catalyst. Modification is carried out to prepare a solid condensation catalyst; the solid condensation catalyst of the present invention is used to catalyze the reaction of benzaldehyde with n-heptanal or n-octyl aldehyde to obtain α-pentyl cinnamaldehyde or α-hexyl cinnamaldehyde. The solid condensation catalyst of the present invention has a high conversion rate of catalyzed condensation reaction, the conversion rate of n-heptanal and n-octylaldehyde can reach 99%, is easy to separate, has high product purity, high selectivity, and α-pentyl cinnamaldehyde and α-hexyl cinnamaldehyde The condensation selectivity can reach more than 98%, and the ratio of E-type isomer to Z-type isomer can reach 97:3-99:1.

Description

technical field [0001] The invention belongs to the technical field of fragrances, and in particular relates to a preparation method and application of a solid condensation catalyst. The solid condensation catalyst of the invention is used to catalyze the preparation of fragrance intermediates. Background technique [0002] α-Amyl cinnamaldehyde and α-Hexyl cinnamaldehyde are two very widely used fragrances. α-Amyl cinnamaldehyde has gardenia, jasmine, tuberose fragrance, the fragrance is close to the real flower, it is an important synthetic fragrance, it is an indispensable fragrance for the preparation of jasmine essence, and it is also widely used in the preparation of other floral essences, in soap It is used in a large amount in fragrances and detergents. α-Hexylcinnamaldehyde has a long-lasting aroma of jasmine, gardenia and herbs, and the aroma is better after dilution. It is one of the most abundant spices in foreign countries, and it is also one of the most floral...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/02C07C45/74C07C47/232C07F7/18
CPCB01J31/0275C07B2200/09C07C45/74C07C47/232
Inventor 张金钟马啸方万军黄冬郑海东王正帅
Owner SHANDONG NHU PHARMA
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