A kind of preparation method of gamma-substituted hexadienoic acid

A technology of hexadienoic acid and catalyst, applied in the preparation of carboxylate, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problems of many side reactions, difficult separation, long process flow, etc., to reduce energy consumption and cost, reduce Consumption and emissions, the effect of reducing process flow

Active Publication Date: 2022-04-19
ANHUI JINGHE IND
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Problems solved by technology

[0007] 4) Crotonaldehyde and acetaldehyde condensation method, that is, crotonaldehyde and acetaldehyde are condensed under the action of dilute alkali to obtain sorbaldehyde, and sorbaldehyde is oxidized with oxygen under the action of silver oxide to obtain sorbic acid. There are many side reactions, and the products are complex and difficult to separate. low yield;
[0011] Although some of these process routes have been industrialized, the common disadvantages are low yield, many side reactions, and more pollution of three wastes. Some process routes have long process flow, complicated operation, rare raw materials, and some raw materials and intermediates are toxic.

Method used

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  • A kind of preparation method of gamma-substituted hexadienoic acid

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Experimental program
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Embodiment 1

[0032] (1) Add 0.09mg of palladium chloride (0.0005mmol) into a 15ml pressure reaction tube, add 1.5ml of potassium dihydrogen phosphate buffer solution adjusted to pH 3 by phosphoric acid, add 1.0ml of tert-butanol and 0.1 mg of tetrabutyl chloride ammonium chloride, stirred evenly, replaced with 99% oxygen, then added 0.03 ml 1-(2-furyl)-1-methylmethanol (0.3 mmol), sealed the reaction tube, and heated in a water bath at 60°C Stir for 24 hours;

[0033] (2) Release gas after the reaction, cool the pressure reaction tube to room temperature, add 3 mL of ethyl acetate to the reaction solution for extraction, and carry out vacuum distillation on the upper layer of ethyl acetate to obtain 2,4-hexadienedioic acid (γ - position is hydrogen), and ethyl acetate is recovered, and analyzed by gas chromatography: 1-(2-furyl)-1-methylmethanol conversion rate is 100%, 2,4-hexadienedioic acid (γ-position is Hydrogen) yield greater than 92%.

Embodiment 2

[0035] (1) Add 4.5mg of palladium acetate (0.02mmol) into a 1L autoclave, add 300ml of sodium acetate buffer solution adjusted to pH 2.6 with hydrochloric acid, add 200ml of tert-butanol and 5mg of tetrabutylammonium chloride, and stir After uniformity, replace it with oxygen with a concentration of 98%, then add 10ml 1-(2-furyl)-1-methylmethanol (0.1mol), seal the high-pressure reactor, and react at a temperature of 60°C for 48 hours to control the oxygen pressure 0.3MPa;

[0036] (2) Release the gas after the reaction, cool the autoclave to room temperature, add 100ml ethyl acetate to the reaction solution and extract three times, combine the ethyl acetate phase, and carry out vacuum distillation on the ethyl acetate phase to obtain 2,4-hexyl acetate Dienoic acid (the γ-position is hydrogen), and ethyl acetate was recovered, and analyzed by gas chromatography: the conversion rate of 1-(2-furyl)-1-methylmethanol was 99.9%, and 2,4-hexadienoic acid ( The γ-position is hydroge...

Embodiment 3

[0038] 0.23mg of Pd(NO 3 ) 2 ·nH 2Add O (0.001mmol) into a 1L autoclave, add 300ml of sodium hydrogen phosphate buffer solution adjusted to pH 2.3 by phosphoric acid, add 100ml of ethyl acetate and 5mg of triphenylphosphine, stir well and use a concentration of 99% Then add 10ml of 1-(2-furyl)-1-ethylmethanol (0.1mol), seal the autoclave, and react at 80°C for 12 hours under temperature control, and control the oxygen pressure to 0.5MPa;

[0039] (2) Release the gas after the reaction, cool the autoclave to room temperature, add 100ml ethyl acetate to the reaction solution and extract three times, combine the ethyl acetate phase, and carry out vacuum distillation on the ethyl acetate phase to obtain 2,4-heptyl Dienoic acid (the γ-position is a methyl group), and ethyl acetate was recovered, and analyzed by gas chromatography: the conversion rate of 1-(2-furyl)-1-ethylmethanol was 98%, and the conversion rate of 2,4-heptadienoic acid (The γ-position is a methyl group) and th...

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Abstract

The invention relates to a preparation method of γ-substituted hexadienoic acid, which is characterized in that: (1) at 10-40°C, add a solvent, a catalyst, and a catalyst assistant to a reaction vessel, stir, and introduce oxygen, and add 1-( 2-furyl)-1-alkylcarbinol, control catalyst: catalytic promoter: the molar ratio of 1-(2-furyl)-1-alkylcarbinol is 0.0001~5:0.0001~3:100, and the reaction temperature is 0~200℃, pressure 0.1~20MPa, reaction 1~74h; solvent is a mixture of water phase and organic phase with a volume ratio of 1:0.01~3, the water phase is a phosphate acid solution, and the organic phase is a reaction inert solvent , the catalyst is a palladium compound, and the catalytic assistant is an amine or a phosphine compound; (2) cooling the reaction vessel to room temperature, adding an organic solvent for extraction, and performing vacuum distillation on the organic phase. The invention has the advantages of avoiding technical and economic disadvantages in the existing synthetic route, simplifying the technological process, reducing consumption and emission, reducing energy consumption and cost, and being suitable for industrialized production with expanded production capacity.

Description

technical field [0001] The invention belongs to the field of fine chemical preparation, and relates to a method for preparing gamma-substituted hexadienoic acid by catalytic oxidation of 1-(2-furyl)-1-alkylmethanol as a raw material. Background technique [0002] 2,4-Hexadienoic acid, commonly known as sorbic acid, molecular formula CH 3 -CH=CH-CH=CH-COOH, the molecular structure contains a carboxyl group and a conjugated double bond, the carboxyl group makes it more acidic and can inhibit the growth of microorganisms; the conjugated double bond can be combined with the sulfhydryl group of the microbial enzyme (pH< 6), thereby destroying the structure of the enzyme system, inactivating the enzyme, and finally inhibiting the reproduction of microorganisms to achieve the antiseptic and fresh-keeping effect. Therefore, sorbic acid and its sodium salt and potassium salt are a new type of food additive, which can inhibit the growth of bacteria, molds, yeasts, etc., with remar...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/21C07C51/48C07C51/44C07C57/03
CPCC07C51/21C07C51/48C07C51/44C07C57/03
Inventor 陶长文陈朝晖颜作标
Owner ANHUI JINGHE IND
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