CN114394898A - Preparation method of 5-oxohexanoate - Google Patents

Preparation method of 5-oxohexanoate Download PDF

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CN114394898A
CN114394898A CN202210291643.0A CN202210291643A CN114394898A CN 114394898 A CN114394898 A CN 114394898A CN 202210291643 A CN202210291643 A CN 202210291643A CN 114394898 A CN114394898 A CN 114394898A
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propionate
catalyst
methyl
acrylate
oxohexanoate
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侯永生
张强
李盼盼
朱素娟
吴国军
张立滨
潘光辉
马华青
武海鹏
刘恒
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Shandong Zhiyong Chemical Industry Technology Research Institute Co ltd
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Shandong Zhiyong Chemical Industry Technology Research Institute Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0237—Amines
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0271—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds also containing elements or functional groups covered by B01J31/0201 - B01J31/0231
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
    • C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds

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Abstract

The invention discloses a preparation method of 5-oxohexanoate, belonging to the technical field of oxohexanoate preparation, comprising the steps of preparing a catalyst and carrying out catalytic reaction; the preparation method comprises the steps of adding secondary amine and acrylic ester into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 0.1-0.5MPa, heating to the reaction temperature of 50-150 ℃, preparing the catalyst at the temperature of 50-150 ℃, and cooling the temperature in a kettle to be below 30 ℃ after the preparation is finished, and discharging to obtain the catalyst; the catalytic reaction comprises the steps of adding acetone, acrylic ester and a catalyst into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of nitrogen to be 1-2MPa, heating to perform catalytic reaction, and discharging after the catalytic reaction is finished; the preparation method of the invention can reduce the raw material cost of the product and improve the purity and yield of the 5-oxohexanoate.

Description

Preparation method of 5-oxohexanoate
Technical Field
The invention relates to the technical field of oxohexanoate preparation, and in particular relates to a preparation method of 5-oxohexanoate.
Background
The 5-oxohexanoate compound is an important organic intermediate and has important application in the fields of spices, pesticides, medicines, polymerization catalysis and the like. The existing production technology for preparing 5-oxo caproic acid ester is to react methyl acetoacetate with acrylic ester at 20-200 ℃, and CO needs to be removed in the production process2The atom utilization rate is low, and the yield can only reach 70 percent. Therefore, it is an urgent problem to find a method capable of improving the yield and reaction rate and preventing the reactant from self-polymerization.
The 4-acetylbutyrate compound prepared by the Chinese patent CN112661639A has low yield and long reaction time, and the 5-oxomethyl hexanoate is recovered by an extraction method, so that the whole treatment process is long, the equipment investment is large, and the yield is low (the yield is lower than 70%). And the patent does not specify the recovery mode of the unreacted raw materials and the catalyst, which are important factors affecting the product cost.
In the chinese patent CN113336629A, acetylacetone is used as a raw material, sodium methoxide is used as a catalyst to perform michael addition reaction, deacetylation is required in the production process, and the atom utilization rate is low.
Disclosure of Invention
Aiming at the technical problems, the invention provides a preparation method of 5-oxohexanoate, which comprises the steps of preparing a catalyst by secondary amine, catalyzing acetone to react with acrylic ester to generate the 5-oxohexanoate, and then recovering the catalyst, raw materials and other substances in a rectification mode, so that the raw material cost of the product is reduced, and the purity and yield of the 5-oxohexanoate are improved.
The invention is realized by the following technical scheme:
a process for preparing 5-oxohexanoate ester includes preparing catalyst and catalytic reaction.
The preparation method comprises the steps of adding secondary amine and acrylic ester into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 0.1-0.5MPa, heating to the reaction temperature of 50-150 ℃, preparing the catalyst at the temperature of 50-150 ℃, and cooling the temperature in a kettle to be below 30 ℃ after the preparation is finished, and discharging to obtain the catalyst.
The secondary amine is one or more of diethylamine, dipropylamine, tetrahydropyrrole, piperidine, morpholine, piperazine and pyrrole.
The acrylate in the preparation catalyst is one of methyl acrylate, ethyl acrylate and butyl acrylate.
The catalyst in the preparation of the catalyst is methyl 3- (diethylamino) propionate, ethyl 3- (diethylamino) propionate, butyl 3- (diethylamino) propionate, methyl 3- (dipropylamino) propionate, ethyl 3- (dipropylamino) propionate, butyl 3- (dipropylamino) propionate, methyl 3- (pyrrolidin-1-yl) propionate, ethyl 3- (pyrrolidin-1-yl) propionate, butyl 3- (pyrrolidin-1-yl) propionate, methyl 3- (piperidin-1-yl) propionate, ethyl 3- (piperidin-1-yl) propionate, butyl 3- (piperidin-1-yl) propionate, methyl 3-morpholinopropionate, ethyl 3-morpholinopropionate, 3-morpholinyl butyl propionate, 3-piperazinyl methyl propionate, 3-piperazinyl ethyl propionate, 3-piperazinyl butyl propionate, 3-pyrrolyl methyl propionate, 3-pyrrolyl ethyl propionate, or 3-pyrrolyl butyl propionate;
when the secondary amine is diethylamine and the acrylate in the preparation catalyst is methyl acrylate, the catalyst is methyl 3- (diethylamino) propionate;
when the secondary amine is diethylamine and the acrylate in the preparation catalyst is ethyl acrylate, the catalyst is ethyl 3- (diethylamino) propionate;
when the secondary amine is diethylamine and the acrylate in the preparation catalyst is butyl acrylate, the catalyst is 3- (diethylamino) butyl propionate;
when the secondary amine is dipropylamine and the acrylate in the catalyst is methyl acrylate, the catalyst is 3- (dipropylamino) methyl propionate;
when the secondary amine is dipropylamine and the acrylate in the prepared catalyst is ethyl acrylate, the catalyst is 3- (dipropylamino) ethyl propionate;
when the secondary amine is dipropylamine and the acrylate in the catalyst is butyl acrylate, the catalyst is 3- (dipropylamino) butyl propionate;
when the secondary amine is pyrrolidine and the acrylate in the catalyst is methyl acrylate, the catalyst is 3- (pyrrolidine-1-yl) methyl propionate;
when the secondary amine is pyrrolidine and the acrylate in the prepared catalyst is ethyl acrylate, the catalyst is 3- (pyrrolidine-1-yl) ethyl propionate;
when the secondary amine is pyrrolidine and the acrylate in the catalyst is butyl acrylate, the catalyst is 3- (pyrrolidine-1-yl) butyl propionate;
when the secondary amine is piperidine and the acrylate in the catalyst is methyl acrylate, the catalyst is 3- (piperidine-1-yl) methyl propionate;
when the secondary amine is piperidine and the acrylate in the catalyst is ethyl acrylate, the catalyst is 3- (piperidine-1-yl) ethyl propionate;
when the secondary amine is piperidine and the acrylate in the catalyst is butyl acrylate, the catalyst is 3- (piperidine-1-yl) butyl propionate;
when the secondary amine is morpholine and the acrylate in the preparation catalyst is methyl acrylate, the catalyst is 3-morpholinyl methyl propionate;
when the secondary amine is morpholine and the acrylate in the catalyst is ethyl acrylate, the catalyst is 3-morpholinyl ethyl propionate;
when the secondary amine is morpholine and the acrylate in the preparation catalyst is butyl acrylate, the catalyst is 3-morpholinyl butyl propionate;
when the secondary amine is piperazine and the acrylate in the preparation catalyst is methyl acrylate, the catalyst is 3-piperazinyl methyl propionate;
when the secondary amine is piperazine and the acrylate in the catalyst is ethyl acrylate, the catalyst is 3-piperazinylpropionic acid ethyl ester;
when the secondary amine is piperazine and the acrylate in the preparation catalyst is butyl acrylate, the catalyst is 3-piperazinyl butyl propionate;
when the secondary amine is pyrrole and the acrylate in the preparation catalyst is methyl acrylate, the catalyst is 3-pyrrolyl methyl propionate;
when the secondary amine is pyrrole and the acrylate in the catalyst is ethyl acrylate, the catalyst is 3-pyrrolyl ethyl propionate;
when the secondary amine is pyrrole and the acrylate in the preparation of the catalyst is butyl acrylate, the catalyst is 3-pyrrolyl butyl propionate.
Wherein the molar ratio of the secondary amine to the acrylate in the preparation catalyst is 1: 1-3.
Preferably, the reaction temperature in the preparation of the catalyst is 80 to 100 ℃.
The reaction time in the preparation of the catalyst is 1-5 h.
The catalytic reaction comprises the steps of adding acetone, acrylic ester and a catalyst into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 1-2MPa, heating to 100-170 ℃, carrying out catalytic reaction at the temperature of 100-170 ℃, and discharging after the catalytic reaction is finished and the temperature in the kettle is reduced to below 30 ℃ to obtain a feed liquid;
feeding the feed liquid into a rectifying tower, controlling the extraction temperature at the top of the rectifying tower to be 88 ℃ and the pressure in a kettle to be normal pressure, and recovering acetone and acrylic ester to obtain a mixture of acetone and acrylic ester; controlling the temperature of the rectifying tower to be 100-108 ℃, and controlling the pressure to be 266-665Pa, and recycling and reusing the catalyst; controlling the temperature of the rectifying tower to be 112-130 ℃ and the pressure to be 665Pa, distilling out the product 5-oxohexanoate, wherein the yield of the prepared 5-oxohexanoate is 80-90 percent and the purity is 98-99 percent.
The acrylic ester in the catalytic reaction is one of methyl acrylate, ethyl acrylate and butyl acrylate;
in the catalytic reaction, 5-oxohexanoate is one of methyl 5-oxohexanoate, ethyl 5-oxohexanoate and butyl 5-oxohexanoate;
when the acrylate in the catalytic reaction is methyl acrylate, the 5-oxohexanoate is methyl 5-oxohexanoate; when the acrylate in the catalytic reaction is ethyl acrylate, the 5-oxohexanoate is 5-oxohexanoate ethyl ester; when the acrylate in the catalytic reaction is butyl acrylate, the 5-oxohexanoate is butyl 5-oxohexanoate.
When the acrylic ester in the catalytic reaction is methyl acrylate, distilling out a product in a rectifying tower, controlling the temperature of the rectifying tower to be 112 ℃ and controlling the pressure to be 665 Pa; when the acrylic ester in the catalytic reaction is ethyl acrylate, distilling out a product in a rectifying tower, controlling the temperature of the rectifying tower to 118 ℃ and controlling the pressure to 665 Pa; when the acrylic ester in the catalytic reaction is butyl acrylate, the product is distilled out by using a rectifying tower, the temperature of the rectifying tower is controlled to 130 ℃, and the pressure is controlled to 665 Pa.
In the catalytic reaction step, the molar ratio of acetone, acrylate and catalyst is 1-10: 1: 0.05-1.
The reaction time of the catalytic reaction is 3-5 h.
The advantages of the invention include the following:
(1) according to the preparation method of the 5-oxohexanoate, the novel catalyst is obtained by reacting the secondary amine with the acrylate, so that the selectivity and yield of the reaction are effectively improved, the yield of the 5-oxohexanoate prepared by the method is 80-90%, and the purity is 98-99%;
(2) according to the preparation method of the 5-oxohexanoate, the raw materials and the catalyst are recovered by rectification, so that the production cost is effectively reduced, and the product has a relatively high competitive advantage.
Drawings
FIG. 1 is a gas chromatogram of the feed solution prepared by the catalytic reaction in example 10;
FIG. 2 is a gas chromatogram of a methyl 5-oxohexanoate standard;
FIG. 3 is a gas chromatogram of the feed solution prepared by the catalytic reaction in example 11;
FIG. 4 is a gas chromatogram of ethyl 5-oxohexanoate standard;
FIG. 5 is a gas chromatogram of the feed solution prepared by the catalytic reaction in example 12;
FIG. 6 is a gas chromatogram of butyl 5-oxohexanoate standard.
Detailed description of the invention
The following description of the preferred embodiments of the present invention is provided for the purpose of illustration and description, and is in no way intended to limit the invention.
Example 1
A preparation method of methyl 5-oxohexanoate comprises the following steps:
1. preparing a catalyst: adding diethylamine and methyl acrylate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen gas to 0.1MPa, heating to the reaction temperature of 50 ℃, preparing a catalyst at 50 ℃, reacting for 1h, cooling the temperature in the reactor to below 30 ℃, and discharging to obtain the methyl 3- (diethylamino) propionate.
Wherein the mol ratio of the diethylamine to the methyl acrylate is 1: 1.
2. and (3) catalytic reaction: adding acetone, methyl acrylate and 3- (diethylamino) methyl propionate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 1MPa, heating to 100 ℃, carrying out catalytic reaction at 100 ℃, cooling the temperature in the reactor to be below 30 ℃ after reacting for 3 hours, and discharging to obtain a feed liquid;
feeding the feed liquid into a rectifying tower, controlling the extraction temperature at the top of the rectifying tower to be 88 ℃ and the pressure in a kettle to be normal pressure, and recovering acetone and methyl acrylate to obtain a mixture of acetone and methyl acrylate; controlling the temperature of the rectifying tower to 100 ℃ and the pressure to 266Pa, and recycling and reusing the methyl 3- (diethylamino) propionate; controlling the temperature of the rectifying tower to 112 ℃ and the pressure to 665Pa, distilling out the product of methyl 5-oxohexanoate, wherein the yield of the prepared methyl 5-oxohexanoate is 81.7 percent, the purity is 98 percent, and the density is 0.996g/cm3The boiling point was 202 ℃ and the flash point was 78.6 ℃.
The molar ratio of the acetone, the methyl acrylate and the methyl 3- (diethylamino) propionate is 1: 1: 0.05.
example 2
A preparation method of methyl 5-oxohexanoate comprises the following steps:
1. preparing a catalyst: adding diethylamine and ethyl acrylate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of nitrogen gas to 0.2MPa, heating to the reaction temperature of 60 ℃, preparing a catalyst at 60 ℃, reacting for 1.5h, cooling the temperature in the reactor to below 30 ℃, and discharging to obtain the ethyl 3- (diethylamino) propionate.
Wherein the mol ratio of the diethylamine to the ethyl acrylate is 1: 1.2.
2. and (3) catalytic reaction: adding acetone, methyl acrylate and ethyl 3- (diethylamino) propionate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 1.1MPa, heating to 105 ℃, carrying out catalytic reaction at 105 ℃, reducing the temperature in the reactor to be below 30 ℃ after reacting for 3.5 hours, and discharging to obtain a feed liquid;
feeding the feed liquid into a rectifying tower, controlling the extraction temperature at the top of the rectifying tower to be 88 ℃ and the pressure in a kettle to be normal pressure, and recovering acetone and methyl acrylate to obtain a mixture of acetone and methyl acrylate; controlling the temperature of the rectifying tower to 101 ℃ and the pressure to 280Pa, and recycling and reusing the 3- (diethylamino) ethyl propionate; will be refinedThe temperature of the distillation tower is controlled to 112 ℃, the pressure is controlled to 665Pa, the product of methyl 5-oxohexanoate is distilled, the yield of the prepared methyl 5-oxohexanoate is 80.0 percent, the purity is 98.2 percent, and the density is 0.996g/cm3The boiling point was 202 ℃ and the flash point was 78.6 ℃.
The molar ratio of the acetone to the methyl acrylate to the ethyl 3- (diethylamino) propionate is 2: 1: 0.2.
example 3
A preparation method of methyl 5-oxohexanoate comprises the following steps:
1. preparing a catalyst: adding diethylamine and butyl acrylate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 0.3MPa, heating to the reaction temperature of 70 ℃, preparing a catalyst at 70 ℃, reacting for 1.5h, cooling the temperature in the reactor to be below 30 ℃, and discharging to obtain the butyl 3- (diethylamino) propionate.
Wherein the mol ratio of the diethylamine to the butyl acrylate is 1: 1.
2. and (3) catalytic reaction: adding acetone, methyl acrylate and 3- (diethylamino) butyl propionate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 1.3MPa, heating to 120 ℃, carrying out catalytic reaction at 120 ℃, reducing the temperature in the reactor to be below 30 ℃ after reacting for 3.8 hours, and discharging to obtain feed liquid;
feeding the feed liquid into a rectifying tower, controlling the extraction temperature at the top of the rectifying tower to be 88 ℃ and the pressure in a kettle to be normal pressure, and recovering acetone and methyl acrylate to obtain a mixture of acetone and methyl acrylate; controlling the temperature of the rectifying tower to 102 ℃ and the pressure to 290Pa, and recycling and reusing the 3- (diethylamino) butyl propionate; controlling the temperature of the rectifying tower to 112 ℃ and the pressure to 665Pa, distilling out the product of the methyl 5-oxohexanoate, wherein the yield of the prepared methyl 5-oxohexanoate is 86.8 percent, the purity is 98.5 percent, and the density is 0.996g/cm3The boiling point was 202 ℃ and the flash point was 78.6 ℃.
The molar ratio of the acetone, the methyl acrylate and the butyl 3- (diethylamino) propionate is 3: 1: 0.3.
example 4
A preparation method of ethyl 5-oxohexanoate comprises the following steps:
1. preparing a catalyst: adding dipropylamine and methyl acrylate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen gas to be 0.4MPa, heating to the reaction temperature of 80 ℃, preparing a catalyst at the temperature of 80 ℃, reacting for 1h, cooling the temperature in the reactor to be below 30 ℃, and discharging to obtain the methyl 3- (dipropylamino) propionate.
Wherein the molar ratio of dipropylamine to methyl acrylate is 1: 2.
2. and (3) catalytic reaction: adding acetone, ethyl acrylate and methyl 3- (dipropylamino) propionate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 1.4MPa, heating to 110 ℃, carrying out catalytic reaction at 110 ℃, reducing the temperature in the reactor to be below 30 ℃ after reacting for 3.9 hours, and discharging to obtain a feed liquid;
feeding the feed liquid into a rectifying tower, controlling the extraction temperature at the top of the rectifying tower to be 88 ℃ and the pressure in a kettle to be normal pressure, and recovering acetone and ethyl acrylate to obtain a mixture of acetone and ethyl acrylate; controlling the temperature of the rectifying tower to 103 ℃ and the pressure to 266Pa, and recycling and reusing the methyl 3- (dipropylamino) propionate; controlling the temperature of the rectifying tower to 118 ℃ and the pressure to 665Pa, distilling out the product of the ethyl 5-oxohexanoate, wherein the yield of the prepared ethyl 5-oxohexanoate is 85.2 percent, the purity is 98.6 percent, and the density is 0.9971g/cm3The boiling point was 221.5 ℃ and the flash point was 69.4 ℃.
The molar ratio of the acetone to the ethyl acrylate to the methyl 3- (dipropylamino) propionate is 8: 1: 0.4.
example 5
A preparation method of ethyl 5-oxohexanoate comprises the following steps:
1. preparing a catalyst: adding dipropylamine and ethyl acrylate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 0.5MPa, heating to the reaction temperature of 90 ℃, preparing a catalyst at the temperature of 90 ℃, reacting for 2.5 hours, cooling the temperature in the reactor to be below 30 ℃, and discharging to obtain the 3- (dipropylamino) ethyl propionate.
Wherein the molar ratio of dipropylamine to ethyl acrylate is 1: 2.2.
2. and (3) catalytic reaction: adding acetone, ethyl acrylate and ethyl 3- (dipropylamino) propionate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 1.5MPa, heating to 120 ℃, carrying out catalytic reaction at 120 ℃, cooling the temperature in the reactor to be below 30 ℃ after reacting for 4 hours, and discharging to obtain feed liquid;
feeding the feed liquid into a rectifying tower, controlling the extraction temperature at the top of the rectifying tower to be 88 ℃ and the pressure in a kettle to be normal pressure, and recovering acetone and ethyl acrylate to obtain a mixture of acetone and ethyl acrylate; controlling the temperature of the rectifying tower to 105 ℃ and the pressure to 350Pa, and recycling and reusing the 3- (dipropylamino) ethyl propionate; controlling the temperature of the rectifying tower to 118 ℃ and the pressure to 665Pa, distilling out the product of the ethyl 5-oxohexanoate, wherein the yield of the prepared ethyl 5-oxohexanoate is 90.0 percent, the purity is 98.9 percent, and the density is 0.9971g/cm3The boiling point was 221.5 ℃ and the flash point was 69.4 ℃.
The molar ratio of the acetone to the ethyl acrylate to the ethyl 3- (dipropylamino) propionate is 9: 1: 0.5.
example 6
A preparation method of ethyl 5-oxohexanoate comprises the following steps:
1. preparing a catalyst: adding dipropylamine and butyl acrylate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 0.5MPa, heating to the reaction temperature of 100 ℃, preparing a catalyst at the temperature of 100 ℃, after reacting for 3 hours, cooling the temperature in the reactor to be below 30 ℃, and discharging to obtain the butyl 3- (dipropylamino) propionate.
Wherein the molar ratio of dipropylamine to butyl acrylate is 1: 2.5.
2. and (3) catalytic reaction: adding acetone, ethyl acrylate and 3- (dipropylamino) butyl propionate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 1.6MPa, heating to 130 ℃, carrying out catalytic reaction at 130 ℃, cooling to below 30 ℃ after reacting for 4.2 hours, and discharging to obtain a feed liquid;
feeding the feed liquid into a rectifying tower, controlling the extraction temperature at the top of the rectifying tower to be 88 ℃ and the pressure in a kettle to be normal pressure, and recovering acetone and ethyl acrylate to obtain a mixture of acetone and ethyl acrylate; controlling the temperature of the rectifying tower to 106 ℃ and the pressure to 350Pa, and recycling and reusing the 3- (dipropylamino) butyl propionate; controlling the temperature of the rectifying tower to 118 ℃ and the pressure to 665Pa, distilling out the product of the ethyl 5-oxohexanoate, wherein the yield of the prepared ethyl 5-oxohexanoate is 88.5 percent, the purity is 98.6 percent, and the density is 0.9971g/cm3The boiling point was 221.5 ℃ and the flash point was 69.4 ℃.
The molar ratio of the acetone to the ethyl acrylate to the butyl 3- (dipropylamino) propionate is 10: 1: 0.8.
example 7
A preparation method of 5-oxobutyl hexanoate comprises the following steps:
1. preparing a catalyst: adding pyrrolidine and methyl acrylate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 0.3MPa, heating to the reaction temperature of 95 ℃, preparing a catalyst at the temperature of 95 ℃, after reacting for 4 hours, cooling the temperature in the reactor to be below 30 ℃, and discharging to obtain the 3- (pyrrolidine-1-yl) methyl propionate.
Wherein the molar ratio of dipropylamine to butyl acrylate is 1: 2.8.
2. and (3) catalytic reaction: adding acetone, butyl acrylate and 3- (pyrrolidine-1-yl) methyl propionate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 1.7MPa, heating to 140 ℃, carrying out catalytic reaction at 140 ℃, cooling the temperature in the reactor to be below 30 ℃ after reacting for 4.5 hours, and discharging to obtain a feed liquid;
feeding the feed liquid into a rectifying tower, controlling the extraction temperature at the top of the rectifying tower to be 88 ℃ and the pressure in a kettle to be normal pressure, and recovering acetone and butyl acrylate to obtain a mixture of acetone and butyl acrylate; the temperature of the rectifying tower is controlled to be 108 DEG CThe pressure is controlled to be 400Pa, and the 3- (pyrrolidine-1-yl) methyl propionate is recycled and reused; controlling the temperature of the rectifying tower to 130 ℃ and the pressure to 665Pa, distilling out the product of the butyl 5-oxohexanoate, wherein the yield of the prepared butyl 5-oxohexanoate is 89.2 percent, the purity is 98.8 percent, and the density is 0.959g/cm3The boiling point was 260 ℃ and the flash point was 107.7 ℃.
The molar ratio of acetone, butyl acrylate and methyl 3- (pyrrolidine-1-yl) propionate is 8.5: 1: 0.9.
example 8
A preparation method of 5-oxobutyl hexanoate comprises the following steps:
1. preparing a catalyst: adding pyrrolidine and ethyl acrylate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 0.2MPa, heating to the reaction temperature of 110 ℃, preparing a catalyst at the temperature of 110 ℃, reacting for 5 hours, cooling the temperature in the reactor to be below 30 ℃, and discharging to obtain the ethyl 3- (pyrrolidine-1-yl) propionate.
Wherein the mole ratio of the tetrahydropyrrole to the ethyl acrylate is 1: 3.
2. and (3) catalytic reaction: adding acetone, butyl acrylate and ethyl 3- (pyrrolidine-1-yl) propionate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 1.8MPa, heating to 150 ℃, carrying out catalytic reaction at 150 ℃, cooling the temperature in the kettle to be below 30 ℃ after reacting for 5 hours, and discharging to obtain a feed liquid;
feeding the feed liquid into a rectifying tower, controlling the extraction temperature at the top of the rectifying tower to be 88 ℃ and the pressure in a kettle to be normal pressure, and recovering acetone and butyl acrylate to obtain a mixture of acetone and butyl acrylate; controlling the temperature of the rectifying tower to 106 ℃ and the pressure to 600Pa, and recycling and reusing the 3- (pyrrolidine-1-yl) ethyl propionate; controlling the temperature of the rectifying tower to 130 ℃ and the pressure to 665Pa, distilling out the product of the butyl 5-oxohexanoate, wherein the yield of the prepared butyl 5-oxohexanoate is 89.8 percent, the purity is 98.7 percent, and the density is 0.959g/cm3The boiling point was 260 ℃ and the flash point was 107.7 ℃.
The molar ratio of the acetone, the butyl acrylate and the 3- (pyrrolidine-1-yl) ethyl propionate is 7: 1: 0.1.
example 9
A preparation method of 5-oxobutyl hexanoate comprises the following steps:
1. preparing a catalyst: adding pyrrolidine and butyl acrylate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 0.2MPa, heating to the reaction temperature of 120 ℃, preparing a catalyst at the temperature of 120 ℃, reacting for 4.2 hours, cooling the temperature in the reactor to be below 30 ℃, and discharging to obtain the 3- (pyrrolidine-1-yl) butyl propionate.
Wherein the mole ratio of the tetrahydropyrrole to the butyl acrylate is 1: 3.
2. and (3) catalytic reaction: adding acetone, butyl acrylate and 3- (pyrrolidine-1-yl) butyl propionate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 1.2MPa, heating to 160 ℃, carrying out catalytic reaction at 160 ℃, cooling the temperature in the reactor to be below 30 ℃ after reacting for 4.5 hours, and discharging to obtain a feed liquid;
feeding the feed liquid into a rectifying tower, controlling the extraction temperature at the top of the rectifying tower to be 88 ℃ and the pressure in a kettle to be normal pressure, and recovering acetone and butyl acrylate to obtain a mixture of acetone and butyl acrylate; controlling the temperature of the rectifying tower to 107 ℃ and the pressure to 665Pa, and recycling and applying the 3- (pyrrolidine-1-yl) butyl propionate; controlling the temperature of the rectifying tower to 130 ℃ and the pressure to 665Pa, distilling out the product of the butyl 5-oxohexanoate, wherein the yield of the prepared butyl 5-oxohexanoate is 88.9 percent, the purity is 98.7 percent, and the density is 0.959g/cm3The boiling point was 260 ℃ and the flash point was 107.7 ℃.
The molar ratio of the acetone, the butyl acrylate and the 3- (pyrrolidine-1-yl) butyl propionate is 9: 1: 0.2.
example 10
A preparation method of methyl 5-oxohexanoate comprises the following steps:
1. preparing a catalyst: adding piperidine and methyl acrylate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 0.1MPa, heating to the reaction temperature of 90 ℃, preparing a catalyst at the temperature of 90 ℃, reacting for 1h, cooling the temperature in the reactor to be below 30 ℃, and discharging to obtain the 3- (piperidine-1-yl) methyl propionate.
Wherein the molar ratio of piperidine to methyl acrylate is 1: 2.
2. and (3) catalytic reaction: adding acetone, methyl acrylate and 3- (piperidine-1-yl) methyl propionate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 2MPa, heating to 170 ℃, carrying out catalytic reaction at 170 ℃, cooling the temperature in the reactor to be below 30 ℃ after reacting for 5 hours, and discharging to obtain feed liquid;
performing gas chromatography on the feed liquid to obtain a gas chromatogram shown in FIG. 1;
the gas chromatogram of the methyl 5-oxohexanoate standard is shown in FIG. 2;
feeding the feed liquid into a rectifying tower, controlling the extraction temperature at the top of the rectifying tower to be 88 ℃ and the pressure in a kettle to be normal pressure, and recovering acetone and methyl acrylate to obtain a mixture of acetone and methyl acrylate; controlling the temperature of the rectifying tower to 100 ℃ and the pressure to 300Pa, and recycling and applying the methyl 3- (piperidine-1-yl) propionate; controlling the temperature of the rectifying tower to 112 ℃ and the pressure to 665Pa, distilling out the product of the methyl 5-oxohexanoate, wherein the yield of the prepared methyl 5-oxohexanoate is 85.5 percent, the purity is 98.4 percent, and the density is 0.996g/cm3The boiling point was 202 ℃ and the flash point was 78.6 ℃.
The molar ratio of the acetone, the methyl acrylate and the methyl 3- (piperidine-1-yl) propionate is 5: 1: 0.35.
example 11
A preparation method of ethyl 5-oxohexanoate comprises the following steps:
1. preparing a catalyst: adding piperidine and ethyl acrylate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 0.2MPa, heating to the reaction temperature of 70 ℃, preparing a catalyst at 70 ℃, reacting for 1h, cooling the temperature in the reactor to be below 30 ℃, and discharging to obtain the 3- (piperidine-1-yl) ethyl propionate.
Wherein the molar ratio of piperidine to ethyl acrylate is 1: 2.5.
2. and (3) catalytic reaction: adding acetone, ethyl acrylate and ethyl 3- (piperidine-1-yl) propionate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 1.2MPa, heating to 150 ℃, carrying out catalytic reaction at 150 ℃, cooling the temperature in the reactor to be below 30 ℃ after reacting for 4 hours, and discharging to obtain a feed liquid;
performing gas chromatography on the feed liquid to obtain a gas chromatogram shown in FIG. 3;
the gas chromatogram of the ethyl 5-oxohexanoate standard is shown in FIG. 4;
feeding the feed liquid into a rectifying tower, controlling the extraction temperature at the top of the rectifying tower to be 88 ℃ and the pressure in a kettle to be normal pressure, and recovering acetone and ethyl acrylate to obtain a mixture of acetone and ethyl acrylate; controlling the temperature of the rectifying tower to 105 ℃ and the pressure to 320Pa, and recycling and reusing the 3- (piperidine-1-yl) ethyl propionate; controlling the temperature of the rectifying tower to 118 ℃ and the pressure to 665Pa, distilling out the product of the ethyl 5-oxohexanoate, wherein the yield of the prepared ethyl 5-oxohexanoate is 89.2 percent, the purity is 98.6 percent, and the density is 0.9971g/cm3The boiling point was 221.5 ℃ and the flash point was 69.4 ℃.
The molar ratio of the acetone to the ethyl acrylate to the ethyl 3- (piperidin-1-yl) propionate is 7: 1: 0.25.
example 12
A preparation method of 5-oxobutyl hexanoate comprises the following steps:
1. preparing a catalyst: adding piperidine and butyl acrylate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 0.3MPa, heating to the reaction temperature of 50 ℃, preparing a catalyst at the temperature of 50 ℃, reacting for 1h, cooling the temperature in the reactor to be below 30 ℃, and discharging to obtain the 3- (piperidine-1-yl) butyl propionate.
Wherein the molar ratio of piperidine to butyl acrylate is 1: 1.8.
2. and (3) catalytic reaction: adding acetone, butyl acrylate and 3- (piperidine-1-yl) butyl propionate into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 1.4MPa, heating to 150 ℃, carrying out catalytic reaction at 150 ℃, reducing the temperature in the kettle to be below 30 ℃ after reacting for 5 hours, and discharging to obtain a feed liquid;
performing gas chromatography on the feed liquid to obtain a gas chromatogram shown in FIG. 5;
the gas chromatogram of the butyl 5-oxohexanoate standard is shown in FIG. 6;
feeding the feed liquid into a rectifying tower, controlling the extraction temperature at the top of the rectifying tower to be 88 ℃ and the pressure in a kettle to be normal pressure, and recovering acetone and butyl acrylate to obtain a mixture of acetone and butyl acrylate; controlling the temperature of the rectifying tower to 102 ℃ and the pressure to 665Pa, and recycling and applying butyl 3- (piperidine-1-yl) propionate; controlling the temperature of the rectifying tower to 130 ℃ and the pressure to 665Pa, distilling out the product of the butyl 5-oxohexanoate, wherein the yield of the prepared butyl 5-oxohexanoate is 87.1 percent, the purity is 98.5 percent, and the density is 0.959g/cm3The boiling point was 260 ℃ and the flash point was 107.7 ℃.
The molar ratio of the acetone, the methyl acrylate and the butyl 3- (piperidine-1-yl) propionate is 10: 1: 0.05.
example 13
A methyl 5-oxohexanoate was prepared in the same manner as in example 1, except that: in the step 1, morpholine and methyl acrylate are used as raw materials for preparing the catalyst, and the generated catalyst is 3-morpholinyl methyl propionate, wherein the molar ratio of morpholine to methyl acrylate is 1: 1; the catalytic reaction in the 2 nd step used 3-morpholinomethyl propionate as a catalyst, and the prepared methyl 5-oxohexanoate had a yield of 85.7%, a purity of 98.1% and a density of 0.996g/cm3The boiling point was 202 ℃ and the flash point was 78.6 ℃.
Example 14
A methyl 5-oxohexanoate was prepared in the same manner as in example 1, except that: in the step 1, morpholine and ethyl acrylate are used as raw materials for preparing the catalyst, and the generated catalyst is 3-morpholinyl ethyl propionate, wherein the mol ratio of morpholine to ethyl acrylate is 1: 2; step 2 catalytic reaction using 3-morpholinyl ethyl propionate as catalyst, preparation of 5-oxoThe yield of methyl caproate was 88.5%, the purity was 98.5%, and the density was 0.996g/cm3The boiling point was 202 ℃ and the flash point was 78.6 ℃.
Example 15
A methyl 5-oxohexanoate was prepared in the same manner as in example 1, except that: in the step 1, morpholine and butyl acrylate are used as raw materials for preparing the catalyst, and the generated catalyst is 3-morpholinyl butyl propionate, wherein the mol ratio of morpholine to butyl acrylate is 1: 3; the catalytic reaction in the 2 nd step used 3-morpholinobutyl propionate as a catalyst, and the prepared methyl 5-oxohexanoate had a yield of 89.0%, a purity of 98.7% and a density of 0.996g/cm3The boiling point was 202 ℃ and the flash point was 78.6 ℃.
Example 16
A methyl 5-oxohexanoate was prepared in the same manner as in example 1, except that: in the step 1, piperazine and methyl acrylate are used as raw materials for preparing the catalyst, and the generated catalyst is 3-piperazinylpropionic acid methyl ester, wherein the molar ratio of piperazine to methyl acrylate is 1: 1; the catalytic reaction in the 2 nd step used methyl 3-piperazinylpropionate as a catalyst, and the prepared methyl 5-oxohexanoate had a yield of 80.3%, a purity of 98.1% and a density of 0.996g/cm3The boiling point was 202 ℃ and the flash point was 78.6 ℃.
Example 17
A methyl 5-oxohexanoate was prepared in the same manner as in example 1, except that: in the step 1, the catalyst is prepared by using piperazine and ethyl acrylate as raw materials, and the generated catalyst is 3-piperazinylpropionic acid ethyl ester, wherein the molar ratio of the piperazine to the ethyl acrylate is 1: 2; the catalytic reaction in the 2 nd step used ethyl 3-piperazinylpropionate as a catalyst, and the prepared methyl 5-oxohexanoate had a yield of 83.6%, a purity of 98.5% and a density of 0.996g/cm3The boiling point was 202 ℃ and the flash point was 78.6 ℃.
Example 18
A methyl 5-oxohexanoate was prepared in the same manner as in example 1, except that: in the step 1, the catalyst is prepared by using piperazine and butyl acrylate as raw materials, and the generated catalyst is 3-piperazinyl butyl propionate, wherein the piperazine and the butyl acrylate areThe molar ratio is 1: 3; the catalytic reaction in the 2 nd step used 3-piperazinylpropionic acid butyl ester as a catalyst, and the prepared 5-oxohexanoic acid methyl ester had a yield of 88.7%, a purity of 98.7% and a density of 0.996g/cm3The boiling point was 202 ℃ and the flash point was 78.6 ℃.
Example 19
A methyl 5-oxohexanoate was prepared in the same manner as in example 1, except that: in the step 1, pyrrole and methyl acrylate are used as raw materials for preparing the catalyst, and the generated catalyst is 3-pyrrolyl methyl propionate, wherein the molar ratio of pyrrole to methyl acrylate is 1: 1; the catalytic reaction in the 2 nd step used methyl 3-pyrrolylpropionate as a catalyst, and methyl 5-oxohexanoate was prepared in a yield of 80.4%, a purity of 98.1% and a density of 0.996g/cm3The boiling point was 202 ℃ and the flash point was 78.6 ℃.
Example 20
A methyl 5-oxohexanoate was prepared in the same manner as in example 1, except that: in the step 1, pyrrole and ethyl acrylate are used as raw materials for preparing the catalyst, and the generated catalyst is 3-pyrrolyl ethyl propionate, wherein the molar ratio of pyrrole to ethyl acrylate is 1: 2; the catalytic reaction in the 2 nd step used ethyl 3-pyrrolylpropionate as a catalyst, and methyl 5-oxohexanoate was prepared in a yield of 85.7%, a purity of 98.6% and a density of 0.996g/cm3The boiling point was 202 ℃ and the flash point was 78.6 ℃.
Example 21
A methyl 5-oxohexanoate was prepared in the same manner as in example 1, except that: in the step 1, pyrrole and butyl acrylate are used as raw materials for preparing the catalyst, and the generated catalyst is 3-pyrrolyl butyl propionate, wherein the molar ratio of pyrrole to butyl acrylate is 1: 2; the catalytic reaction in the 2 nd step used butyl 3-pyrrolylpropionate as a catalyst, and methyl 5-oxohexanoate was prepared in a yield of 89.7%, a purity of 99% and a density of 0.996g/cm3The boiling point was 202 ℃ and the flash point was 78.6 ℃.
Finally, it should be noted that: although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that changes may be made in the embodiments and/or equivalents thereof without departing from the spirit and scope of the invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (5)

1. The preparation method of the 5-oxohexanoate is characterized by comprising the steps of preparing a catalyst and catalyzing reaction;
the preparation method comprises the steps of adding secondary amine and acrylic ester into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 0.1-0.5MPa, heating to the reaction temperature of 50-150 ℃, preparing the catalyst at the temperature of 50-150 ℃, and cooling the temperature in a kettle to be below 30 ℃ after the preparation is finished, and discharging to obtain the catalyst;
the secondary amine is one or more of diethylamine, dipropylamine, tetrahydropyrrole, piperidine, morpholine, piperazine and pyrrole;
the acrylate in the catalyst is one of methyl acrylate, ethyl acrylate and butyl acrylate;
the molar ratio of the secondary amine to the acrylate in the preparation catalyst is 1: 1-3;
the catalytic reaction comprises the steps of adding acetone, acrylic ester and a catalyst into a reactor, replacing air in the reactor with nitrogen, controlling the pressure of the nitrogen to be 1-2MPa, heating to 100-170 ℃, carrying out catalytic reaction at the temperature of 100-170 ℃, and discharging after the catalytic reaction is finished and the temperature in the kettle is reduced to below 30 ℃ to obtain a feed liquid;
feeding the feed liquid into a rectifying tower, controlling the extraction temperature at the top of the rectifying tower to be 88 ℃ and the pressure in a kettle to be normal pressure, and recovering acetone and acrylic ester to obtain a mixture of acetone and acrylic ester; controlling the temperature of the rectifying tower to be 100-108 ℃, and controlling the pressure to be 266-665Pa, and recycling and reusing the catalyst; controlling the temperature of the rectifying tower to be 112-130 ℃ and the pressure to be 665Pa, and distilling out the product 5-oxohexanoate, wherein the yield of the prepared 5-oxohexanoate is 80-90 percent and the purity is 98-99 percent;
the acrylic ester in the catalytic reaction is one of methyl acrylate, ethyl acrylate and butyl acrylate;
in the catalytic reaction, the molar ratio of acetone to acrylic ester to the catalyst is 1-10: 1: 0.05-1.
2. The method of producing a 5-oxohexanoate ester according to claim 1, wherein the catalyst in the production of the catalyst is methyl 3- (diethylamino) propionate, ethyl 3- (diethylamino) propionate, butyl 3- (diethylamino) propionate, methyl 3- (dipropylamino) propionate, ethyl 3- (dipropylamino) propionate, butyl 3- (dipropylamino) propionate, methyl 3- (pyrrolidin-1-yl) propionate, ethyl 3- (pyrrolidin-1-yl) propionate, butyl 3- (pyrrolidin-1-yl) propionate, methyl 3- (piperidin-1-yl) propionate, ethyl 3- (piperidin-1-yl) propionate, butyl 3- (piperidin-1-yl) propionate, 3-morpholinyl methyl propionate, 3-morpholinyl ethyl propionate, 3-morpholinyl butyl propionate, 3-piperazinyl methyl propionate, 3-piperazinyl ethyl propionate, 3-piperazinyl butyl propionate, 3-pyrrolyl methyl propionate, 3-pyrrolyl ethyl propionate, and 3-pyrrolyl butyl propionate.
3. The method of claim 1, wherein the reaction time for preparing the catalyst is 1 to 5 hours.
4. The method of claim 1, wherein the reaction time of the catalytic reaction is 3 to 5 hours.
5. The method of claim 1, wherein the 5-oxohexanoate in the catalytic reaction is one of methyl 5-oxohexanoate, ethyl 5-oxohexanoate, and butyl 5-oxohexanoate.
CN202210291643.0A 2022-03-24 2022-03-24 Preparation method of 5-oxohexanoate Pending CN114394898A (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105693537A (en) * 2015-12-29 2016-06-22 四川光亚聚合物化工有限公司 N-alkyl acrylamide intermediate and preparation method thereof and preparation method of N-alkyl acrylamide
CN112125818A (en) * 2020-09-23 2020-12-25 山东瑞博龙化工科技股份有限公司 System and process for preparing N, N-diethylacrylamide
CN112661639A (en) * 2020-12-07 2021-04-16 浙江工业大学 Synthesis method of 4-acetylbutyrate compound

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105693537A (en) * 2015-12-29 2016-06-22 四川光亚聚合物化工有限公司 N-alkyl acrylamide intermediate and preparation method thereof and preparation method of N-alkyl acrylamide
CN112125818A (en) * 2020-09-23 2020-12-25 山东瑞博龙化工科技股份有限公司 System and process for preparing N, N-diethylacrylamide
CN112661639A (en) * 2020-12-07 2021-04-16 浙江工业大学 Synthesis method of 4-acetylbutyrate compound

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