CN104610197A - Method for synthesizing acryloyl morpholine based on anhydride - Google Patents
Method for synthesizing acryloyl morpholine based on anhydride Download PDFInfo
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- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
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Abstract
The invention discloses a method for synthesizing acryloyl morpholine based on anhydride. The acryloyl morpholine monomer is generated by performing a reaction of the acrylate trichloroacetic anhydride and the morpholine, and the acrylate trichloroacetic anhydride is obtained by performing a reaction of the acrylic acid and the trichloroacetic acid. The method for synthesizing acryloyl morpholine provided by the invention is simple in process route, easy for reaction control, mild in reaction condition, cheap in raw material, stable in product structure and low in cost; and besides, the method also increases the purity and yield of the product and has an industrial application prospect.
Description
Technical field
The present invention relates to the synthetic method of acryloyl morpholine, be specifically related to a kind of method of acid anhydride-based synthesizing propylene morpholide, belong to compou nd synthesis field.
Background technology
Acryloyl morpholine (ACMO) is a kind of water-soluble cpds with carbon carbon unsaturated double-bond, and be colourless or light yellow transparent liquid, its structural formula is:
Because acryloyl morpholine self is nontoxic, and have good biocompatibility, its homopolymer Chang Zuowei medicinal slow release agent, beauty treatment propping agent etc., acryloyl morpholine replaces poisonous acrylamide in water purification process field and applies as water conditioner in recent years.Acryloyl morpholine is also excellent auxiliary agent and the properties-correcting agent of synthetic resins, for the reaction diluent of ultraviolet curable resin, it easily and the material generation copolyreaction such as vinylformic acid, acrylamide, gelatin, significantly can improve the performance such as visco-elasticity, resistant to shearing of product, be widely used in the fields such as oilfield additive, ink addition agent, paper making additive and tackiness agent.
Chinese patent CN101293880B discloses a kind of method of acylation reaction legal system for acryloyl morpholine utilizing acrylate chloride, acrylate chloride is generated after phosphorus trichloride and vinylformic acid acylation reaction, carry out acylation reaction with morpholine after acrylate chloride solvation and obtain crude product acryloyl morpholine, then under vacuum rectifying is carried out to reaction solution, just highly purified acryloyl morpholine can be obtained, yield and purity are all higher, but operational path is longer, intermediate product acrylate chloride poor stability, its double bond is more active, the multiple side reaction of easy generation, yield and purity lower, byproduct of reaction is hydrochloric acid in addition, reactor is corrosive larger, product aftertreatment is complicated, add production cost.
Japanese Patent JP11100375A (JP19970279395) discloses a kind of method by pyrolysis method synthesizing propylene morpholide, raw material is that alkyl replaces propionyl morpholine (4-morpholinyl propionyl morpholine), add an acidic catalyst and under the condition of 390 DEG C of high temperature, carry out vacuum thermal cracking, generate acryloyl morpholine.The operational path of the method is simple, but product is easily polymerized, and yield is low, is generally 29%, and expensive starting materials production cost is high.
The people such as Song Yan disclose in " study on the synthesis of N-acryloyl morpholine " literary composition, with morpholine and methyl acrylate for main raw material, acryloyl morpholine is obtained: first methyl acrylate is under the catalysis of sodium alkoxide (sodium methylate), obtains 3-methoxy methyl propionate with methyl alcohol generation addition reaction through the process such as double bond protection, catalysis aminolysis, catalytic pyrolysis; Then under the effect of transesterification catalyst, then 3-methoxy propyl morpholide is obtained by reacting with morpholine generation catalysis aminolysis; Eventually pass catalytic pyrolysis and obtain acryloyl morpholine.Whole reaction process operational path is longer, and reaction process is wayward.
Summary of the invention
For the defect of prior art, the invention provides a kind of method of acid anhydride-based synthesizing propylene morpholide.Vinylformic acid Trichloroacetic anhydride and morpholine react and generate acryloylmorpholine monomer.Preparation process is:
(1) secondary amine group in vinylformic acid Trichloroacetic anhydride and morpholine reacts and generates secondary amide.
Vinylformic acid Trichloroacetic anhydride is dissolved in organic solvent, drips the mixed solution of morpholine and acid binding agent, react 1 ~ 4 hour under the condition of 0 ~ 5 DEG C, namely obtain crude product acryloyl morpholine.Reaction formula is:
Wherein,
Described acid binding agent includes but not limited to one or more the combination in triethylamine, diethylamine, pyridine, N-methylmorpholine, tripropyl amine, three octyl tertiary amines, sodium bicarbonate, sodium carbonate.Preferred acid binding agent is triethylamine.
Described organic solvent includes but not limited to one or more the combination in ethyl acetate, acetone, toluene.
Described vinylformic acid Trichloroacetic anhydride and morpholine mol ratio are: 1:1 ~ 1:1.5.Preferably, described vinylformic acid Trichloroacetic anhydride and morpholine mol ratio are: 1:1.1.
The mol ratio of described acid binding agent and vinylformic acid Trichloroacetic anhydride is 1:0.9 ~ 1:1.1.Preferably, the mol ratio of acid binding agent and vinylformic acid Trichloroacetic anhydride is 1:1.
Preferably, described temperature of reaction is 2 ~ 4 DEG C, and the reaction times is 1.5 ~ 3 hours.
Preferably, described temperature of reaction is 3 DEG C, and the reaction times is 2 hours.
(2) use stopper in rectifying, prevent monomer polymerization reactions, to increase yield.The crude product acryloyl morpholine obtained in step (1) is joined rectifying in the vacuum rectification tower that stopper is housed, collects the cut of 140 ~ 160 DEG C, obtain final product acryloyl morpholine.
Described stopper is one or more the combination in Resorcinol, para benzoquinone, thiodiphenylamine, toluhydroquinone, oil of mirbane, picric acid, MEHQ, tert-butyl catechol, 2-Tert. Butyl Hydroquinone, 4-methoxyphenol, cuprous chloride, iron trichloride.Preferably, described stopper is Resorcinol, tert-butyl catechol, cuprous chloride form by the ratio combination of 10:10:1.
The present invention's vinylformic acid Trichloroacetic anhydride used can react obtained by vinylformic acid and trichoroacetic acid(TCA).With diacetyl oxide as dewatering agent, a part water is sloughed in two carboxylic acids reactions, generates acid anhydrides.Vinylformic acid is mixed with trichoroacetic acid(TCA), adds Vanadium Pentoxide in FLAKES and stopper, drip diacetyl oxide, react 3 ~ 6 hours under 95 ~ 100 DEG C of conditions.Reacted rear underpressure distillation, removing front-end volatiles, are vinylformic acid Trichloroacetic anhydride.Reaction formula is:
Wherein,
The mol ratio of described vinylformic acid, diacetyl oxide and trichoroacetic acid(TCA) is 1:1:0.5 ~ 1:1.1:2, and further, the mol ratio of vinylformic acid, diacetyl oxide and trichoroacetic acid(TCA) is 1:1:1.
Preferably, described temperature of reaction is 96 ~ 98 DEG C, and the reaction times is 4 ~ 5.5 hours.
Preferably, described temperature of reaction is 97 DEG C, and the reaction times is 5 hours.
The present invention compared with prior art has the following advantages:
(1) reaction conditions is gentle, reduces the polymerization of double bond, decrease side reaction in reaction process, ensure that the stable of quality product, feed stock conversion is higher, purity more than 98%, yield also higher than 75%, purity and yield have had raising by a relatively large margin.
(2) operational path is simple, easy and simple to handle, and reaction is easy to control.The mol ratio of direct control raw material and temperature of reaction can make reacting balance carry out, and do not produce intermediate and directly obtain object product.
(3) environmental friendliness, nontoxic, do not produce gas pollutant.
(4) low in raw material price, cost are low, and product structure is stablized, and has the prospect of industrial applications.
Embodiment
Below by specific embodiment, further technical scheme of the present invention is specifically described.Should be appreciated that, the following examples just as illustrating, and do not limit the scope of the invention, and the apparent change made according to the present invention of those skilled in the art simultaneously and modification are also contained within the scope of the invention.
Embodiment 1:
(1) in four-hole boiling flask, add 72g vinylformic acid to mix with 164g trichoroacetic acid(TCA), add 5g Vanadium Pentoxide in FLAKES, add stopper 2.6 grams, 110g diacetyl oxide is dropwise added drop-wise in above-mentioned mixed solution, react 5 hours under 97 DEG C of conditions.
(2) reacted rear underpressure distillation, removing front-end volatiles, obtain product 165g, are vinylformic acid Trichloroacetic anhydride.
(3) add in solvent by 165g acid anhydrides, be cooled to 0 DEG C, drip 72g morpholine, and add triethylamine 76.5g, maintaining temperature of reaction is 3 DEG C, drips off reaction 2 hours, namely obtains crude product acryloyl morpholine.
(4) crude product acryloyl morpholine is filtered, add stopper underpressure distillation, collect the cut of 140 ~ 160 DEG C, obtain product 96g, be final product acryloyl morpholine.Described stopper is formed by the ratio combination of 10:10:1 by Resorcinol, tert-butyl catechol, cuprous chloride.
Yield is 89.95%, and purity is 98.7%.
Embodiment 2:
(1) add 900g vinylformic acid in a kettle. to mix with 1025g trichoroacetic acid(TCA), add 50g Vanadium Pentoxide in FLAKES, add stopper 26 grams, 1100g diacetyl oxide is added drop-wise in above-mentioned mixed solution, react 3 hours under 100 DEG C of conditions after being added dropwise to complete.
(2) reacted rear underpressure distillation, removing front-end volatiles, obtain vinylformic acid Trichloroacetic anhydride 2071g.
(3) add in solvent by 2071g acid anhydrides, drip 826.5g morpholine, and add pyridine 682.5g, maintaining temperature of reaction is 5 DEG C, is added dropwise to complete rear reaction 1 hour, namely obtains crude product acryloyl morpholine.
(4) crude product acryloyl morpholine is filtered, add stopper underpressure distillation, collect the cut of 140 ~ 160 DEG C, obtain product 1193g, be final product acryloyl morpholine.Described stopper is tert-butyl catechol.
Yield is 79.06%, and purity is 98.8%.
Embodiment 3:
(1) in four-hole boiling flask, add 135g vinylformic acid to mix with 615g trichoroacetic acid(TCA), add 10g Vanadium Pentoxide in FLAKES, add stopper 5.2 grams, 200g diacetyl oxide is dropwise added drop-wise in above-mentioned mixed solution, react 5 hours under 97 DEG C of conditions.
(2) reacted rear underpressure distillation, removing front-end volatiles, obtain 311g vinylformic acid Trichloroacetic anhydride.
(3) add in solvent by 311g acid anhydrides, be cooled to 0 DEG C, drip 186g morpholine, and add N-methylmorpholine 158.5g, maintaining temperature of reaction is 0 DEG C, drips off reaction 4 hours, namely obtains crude product acryloyl morpholine.
(4) crude product acryloyl morpholine is filtered, add stopper underpressure distillation, collect the cut of 140 ~ 160 DEG C, obtain product 181g, be final product acryloyl morpholine.Described stopper is toluhydroquinone.
Yield is 82.98%, and purity is 99.1%.
Embodiment 4:
(1) in four-hole boiling flask, add 20g vinylformic acid to mix with 71.1g trichoroacetic acid(TCA), add 1.5g Vanadium Pentoxide in FLAKES, add stopper 3.8 grams, 30g diacetyl oxide is dropwise added drop-wise in above-mentioned mixed solution, react 3 hours under 95 DEG C of conditions.
(2) reacted rear underpressure distillation, removing front-end volatiles, obtain 56.52g vinylformic acid Trichloroacetic anhydride.
(3) add in solvent by 56.52g acid anhydrides, be cooled to 0 DEG C, drip 25.83g morpholine, and add tripropyl amine 35.5g, maintaining temperature of reaction is 3 DEG C, drips off rear reaction 3 hours, namely obtains crude product acryloyl morpholine.
(4) crude product acryloyl morpholine is filtered, add stopper underpressure distillation, collect the cut of 140 ~ 160 DEG C, obtain product 34.06g, be final product acryloyl morpholine.Described stopper is toluhydroquinone.
Yield is 83.17%, and purity is 98.6%.
Embodiment 5:
(1) in four-hole boiling flask, add 45g vinylformic acid to mix with 127.25g trichoroacetic acid(TCA), add stopper 1.4 grams, add 3g Vanadium Pentoxide in FLAKES, 65g diacetyl oxide is dropwise added drop-wise in above-mentioned mixed solution, react 4.5 hours under 96 DEG C of conditions.
(2) reacted rear underpressure distillation, removing front-end volatiles, obtain 126.43g vinylformic acid Trichloroacetic anhydride.
(3) add in solvent by 126.43g acid anhydrides, be cooled to 0 DEG C, drip 65.68g morpholine, and add three octyl tertiary amine 198.63g, maintaining temperature of reaction is 4 DEG C, drips off rear reaction 2.5 hours, namely obtains crude product acryloyl morpholine.
(4) crude product acryloyl morpholine is filtered, add stopper underpressure distillation, collect the cut of 140 ~ 160 DEG C, obtain product 74.77g, be final product acryloyl morpholine.Described stopper is toluhydroquinone.
Yield is 81.44%, and purity is 98.9%.
Embodiment 6:
(1) in four-hole boiling flask, add 56g vinylformic acid to mix with 205.11g trichoroacetic acid(TCA), add stopper 1.6 grams, add 4g Vanadium Pentoxide in FLAKES, 80g diacetyl oxide is dropwise added drop-wise in above-mentioned mixed solution, react 4 hours under 97 DEG C of conditions.
(2) reacted rear underpressure distillation, removing front-end volatiles, obtain 158.99g vinylformic acid Trichloroacetic anhydride.
(3) add in solvent by 158.99g acid anhydrides, be cooled to 0 DEG C, drip 73.17g morpholine, and add sodium bicarbonate 58.07g, maintaining temperature of reaction is 3 DEG C, drips off rear reaction 3.5 hours, namely obtains crude product acryloyl morpholine.
(4) crude product acryloyl morpholine is filtered, add stopper underpressure distillation, collect the cut of 140 ~ 160 DEG C, obtain product 89.96g, be final product acryloyl morpholine.Described stopper is toluhydroquinone.
Yield is 87.48%, and purity is 99.2%.
Claims (10)
1. a method for acid anhydride-based synthesizing propylene morpholide, its synthetic method is:
(1) vinylformic acid Trichloroacetic anhydride is dissolved in organic solvent, drips the mixed solution of morpholine and acid binding agent, react 1 ~ 4 hour under the condition of 0 ~ 5 DEG C, namely obtain crude product acryloyl morpholine; Its reaction formula is:
Wherein,
Described acid binding agent includes but not limited to one or more the combination in triethylamine, diethylamine, pyridine, N-methylmorpholine, tripropyl amine, three octyl tertiary amines, sodium bicarbonate, sodium carbonate;
Described organic solvent includes but not limited to one or more the combination in ethyl acetate, acetone, toluene;
Described vinylformic acid Trichloroacetic anhydride, morpholine and acid binding agent mol ratio are: 1:1:0.9 ~ 1:1.5:1.1.
(2) the crude product acryloyl morpholine obtained in step (1) is joined rectifying in the vacuum rectification tower that stopper is housed, collect the cut of 140 ~ 160 DEG C, obtain final product acryloyl morpholine;
Described stopper is one or more the combination in Resorcinol, para benzoquinone, thiodiphenylamine, toluhydroquinone, oil of mirbane, picric acid, MEHQ, tert-butyl catechol, 2-Tert. Butyl Hydroquinone, 4-methoxyphenol, cuprous chloride, iron trichloride.
2. the method for synthesizing propylene morpholide according to claim 1, it is characterized in that: described vinylformic acid Trichloroacetic anhydride preparation method is: mixed with trichoroacetic acid(TCA) by vinylformic acid, add Vanadium Pentoxide in FLAKES and stopper, drip diacetyl oxide, react 3 ~ 6 hours under 95 ~ 100 DEG C of conditions; Reacted rear underpressure distillation, removing front-end volatiles, are vinylformic acid Trichloroacetic anhydride; Its reaction formula is:
Wherein,
The mol ratio of described vinylformic acid, diacetyl oxide and trichoroacetic acid(TCA) is 1:1:0.5 ~ 1:1.1:2.
3. the method for synthesizing propylene morpholide according to claim 1 and 2, is characterized in that: described acid binding agent is triethylamine.
4. the method for synthesizing propylene morpholide according to claim 1 and 2, is characterized in that: described vinylformic acid Trichloroacetic anhydride, morpholine and acid binding agent mol ratio are: 1:1.1:1.
5. the method for synthesizing propylene morpholide according to claim 1 and 2, is characterized in that: the temperature of reaction in described vinylformic acid Trichloroacetic anhydride and morpholine reaction process is 2 ~ 4 DEG C, and the reaction times is 1.5 ~ 3 hours.
6. the method for synthesizing propylene morpholide according to claim 5, is characterized in that: described temperature of reaction is 3 DEG C, and the reaction times is 2 hours.
7. the method for synthesizing propylene morpholide according to claim 1 and 2, is characterized in that: described stopper be Resorcinol, tert-butyl catechol, cuprous chloride in mass ratio 10:10:1 combine.
8. the method for synthesizing propylene morpholide according to claim 2, is characterized in that: the mol ratio of described vinylformic acid, diacetyl oxide and trichoroacetic acid(TCA) is 1:1:1.
9. the method for synthesizing propylene morpholide according to claim 2, is characterized in that: the described temperature of reaction preparing vinylformic acid Trichloroacetic anhydride is 96 ~ 98 DEG C, and the reaction times is 4 ~ 5.5 hours.
10. the method for synthesizing propylene morpholide according to claim 9, is characterized in that: described temperature of reaction is 97 DEG C, and the reaction times is 5 hours.
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Cited By (4)
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| CN110483442A (en) * | 2019-08-27 | 2019-11-22 | 苏州双格新材料科技有限公司 | A kind of preparation method of N- acryloyl morpholine |
| CN112608248A (en) * | 2020-12-16 | 2021-04-06 | 无锡海特圣大光电材料科技有限公司 | Method for synthesizing N, N-dimethylaminopropyl acrylamide by decarboxylation |
| CN114989114A (en) * | 2022-06-02 | 2022-09-02 | 杭州福斯特电子材料有限公司 | Synthesis method of N-acryloyl morpholine and photocuring composition |
| CN115925652A (en) * | 2022-12-08 | 2023-04-07 | 南通沃兰化工有限公司 | Preparation method of acryloyl morpholine |
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Cited By (4)
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| CN110483442A (en) * | 2019-08-27 | 2019-11-22 | 苏州双格新材料科技有限公司 | A kind of preparation method of N- acryloyl morpholine |
| CN112608248A (en) * | 2020-12-16 | 2021-04-06 | 无锡海特圣大光电材料科技有限公司 | Method for synthesizing N, N-dimethylaminopropyl acrylamide by decarboxylation |
| CN114989114A (en) * | 2022-06-02 | 2022-09-02 | 杭州福斯特电子材料有限公司 | Synthesis method of N-acryloyl morpholine and photocuring composition |
| CN115925652A (en) * | 2022-12-08 | 2023-04-07 | 南通沃兰化工有限公司 | Preparation method of acryloyl morpholine |
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