A kind of preparation method of lilial

A technology of lily of the valley aldehyde and methacrolein, applied in the field of preparation of lily of the valley aldehyde, can solve the problems of affecting the quality, quality and application effect of lily of the valley aldehyde, insufficient reaction of reactants, and many by-products of reaction products, etc. High yield, sufficient reaction, and the effect of inhibiting polymerization

Active Publication Date: 2019-07-23
SHANDONG NHU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] (1) The process route requires multi-step continuous reaction, and the cost of raw materials is high;
[0008] (2) Insufficient reaction of reactants, resulting in waste of raw materials;
[0009] (3) The yield of the reaction is low, the side reactions are difficult to control, there are many by-products, and the impurities are not easy to remove;
[0010] (4) The target product and unreacted raw materials and auxiliary materials are not easy to separate, and the separation cost is high, and the recovery cost of unreacted raw materials and auxiliary materials is high;
[0011] (5) There are many by-products in the reaction products, which affect the quality, quality and application effect of lilial as a fragrance

Method used

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  • A kind of preparation method of lilial

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] 1) In a 2L reaction flask, add tert-butylbenzene (805g, 6mol) and dichloromethane (510g, 6mol), place it in a low-temperature reaction bath at -20°C, and add tin tetrachloride (261g, 1mol) and sulfonic acid resin (amberlyst15) 10g, stirring and mixing for 5min;

[0059] 2) At -20°C, add 2-methacrolein (140g, 2mol) drop by drop, after 2.5h the dropwise addition is completed, and continue to keep warm for 1.5h;

[0060] 3) Add 400g of 2N hydrochloric acid to quench the reaction, wash with water 3 times, each time with 10mL of water; dry the organic phase with anhydrous MgSO4, moisture ≤ 1.0%. Distill the organic phase at 25°C under reduced pressure of 350mmHg to remove dichloromethane; obtain the crude lyral; carry out rectification on the crude product, collect 89°C / 1mmHg fraction, the fraction quality is 286g, GC content ≥ 98%, water content < 0.3 %, the lyral productive rate is 73%; the methylene chloride recovery rate is 96%, and the tert-butylbenzene recovery rate i...

Embodiment 2

[0062] 1) In a 2L reaction flask, add tert-butylbenzene (805g, 6mol) and 1,2-dichloroethane (390mL, 6mol), place it in a low-temperature reaction bath at -10°C, and add titanium tetrachloride (190g, 1mol) and sulfonic acid resin (amberlyst15) 10g, stir and mix for 30min;

[0063] 2) At -10°C, add 2-methacrolein (140g, 2mol) drop by drop, after 2.5h the dropwise addition is completed, and continue to keep warm for 3h;

[0064] 3) Add 200g of 2N sulfuric acid to quench the reaction, wash three times with 10mL each time; dry the organic phase with anhydrous MgSO4, the moisture content is ≤1.0%. The organic phase was evaporated at 35°C and 350mmHg under reduced pressure to remove 1,2-dichloroethane; the crude lyral was obtained; the crude product was rectified, and the 89°C / 1mmHg fraction was collected. The fraction quality was 204g, and the GC content was ≥98%. The water content is less than 0.3%, and the yield of lilial is 50%; the recovery rate of 1,2-dichloroethane is 98%, an...

Embodiment 3

[0066] 1) In a 2L reaction flask, add tert-butylbenzene (805g, 6mol) and chloroform (390mL, 6mol), place it in a low-temperature reaction bath at -10°C, add titanium tetrachloride (190g, 1mol) and formaldehyde Sulfuric acid (38.4g, 0.4mol), stirred and mixed for 10min;

[0067] 2) At -10°C, add 2-methacrolein (140g, 2mol) drop by drop, after 2.5h the dropwise addition is completed, and continue to keep warm for 3h;

[0068] 3) Add 200g of 2N sulfuric acid to quench the reaction, wash three times with 10mL each time; dry the organic phase with anhydrous MgSO4, the moisture content is ≤1.0%. The organic phase was at 38°C, and the chloroform was evaporated under reduced pressure at 350mmHg; the crude lyral was obtained; the crude product was rectified, and the fraction at 89°C / 1mmHg was collected. The yield of lanaldehyde is 67%; the recovery rate of chloroform is 98%, and the recovery rate of tert-butylbenzene is 97%.

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Abstract

The invention provides a preparation method of lily aldehyde. The method comprises steps as follows: tert-butylbenzene, a solvent and a catalyst are combined and stirred and mixed at a certain temperature; the solvent is any one of dichloromethane, chloroform, nitrobenzene and 1,2-dichloroethane; the catalyst is composition of Lewis acid and an acidic substance providing protons; the certain temperature ranges from subzero 60 DEG C to 40 DEG C; 2-methacrylaldehyde is dropwise added after mixing, and the mixture is kept at the constant temperature continuously after 2-methacrylaldehyde is dropwise added; 2-methacrylaldehyde is dropwise added for 2.5-3.5 h. By means of the method, the yield of lily aldehyde is high and can reach 50%-73%; the recovery rates of the solvent and tert-butylbenzene are high, the cost is saved, and the recovery rate of the solvent is 95%-98% while the recovery rate of tert-butylbenzene is 93%-98%.

Description

technical field [0001] The invention relates to a preparation method of lilial, which belongs to the field of fine chemical industry. Background technique [0002] Lilial (molecular formula: C 14 h 20 O, CAS No.: 80-54-6) Colorless to light yellow liquid, insoluble in water, soluble in ethanol. Spices with fresh floral aromas such as lily of the valley, lily, lilac and cyclamen. The fragrance is fresh and elegant, with a long-lasting fragrance. Its fragrance is gentle, delicate and elegant. It is less irritating to skin and stable to alkali. Because lyral is widely used in soaps and various floral and fantasy flavors, the amount used in spices is up to 20%; another wide application is the synthesis of pesticides for the control of cereal plant pathogens. [0003] Lilial was first successfully developed by Soviet chemist Academician Logionov in 1952. In the late 1950s, Givaudan in Switzerland and UOP in the United States began industrial production and developed rapidly. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/69C07C47/228
CPCC07C45/69C07C47/228
Inventor 冯传密马啸都荣强赵文乐陈为超方万军张金钟
Owner SHANDONG NHU PHARMA
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