CN103588654B - A kind of synthetic method of 3-n-butyl amine base ethyl propionate - Google Patents
A kind of synthetic method of 3-n-butyl amine base ethyl propionate Download PDFInfo
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- CN103588654B CN103588654B CN201310493139.XA CN201310493139A CN103588654B CN 103588654 B CN103588654 B CN 103588654B CN 201310493139 A CN201310493139 A CN 201310493139A CN 103588654 B CN103588654 B CN 103588654B
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- Prior art keywords
- amine base
- butyl amine
- ethyl propionate
- butylamine
- base ethyl
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- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 title claims abstract description 52
- -1 3-n-butyl Chemical group 0.000 title claims abstract description 26
- 238000010189 synthetic method Methods 0.000 title claims abstract description 14
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims abstract description 22
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims abstract description 22
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- HSJPMRKMPBAUAU-UHFFFAOYSA-N cerium(3+);trinitrate Chemical compound [Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O HSJPMRKMPBAUAU-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 238000003756 stirring Methods 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 5
- 238000004508 fractional distillation Methods 0.000 claims description 5
- 238000009413 insulation Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 230000001988 toxicity Effects 0.000 abstract description 4
- 231100000419 toxicity Toxicity 0.000 abstract description 4
- 208000034809 Product contamination Diseases 0.000 abstract description 2
- 230000002349 favourable effect Effects 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 10
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 5
- 229960001826 dimethylphthalate Drugs 0.000 description 5
- 239000000077 insect repellent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZRKEAFHFMSHCD-UHFFFAOYSA-N Ethyl 3-(N-butylacetamido)propionate Chemical compound CCCCN(C(C)=O)CCC(=O)OCC VZRKEAFHFMSHCD-UHFFFAOYSA-N 0.000 description 1
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229960001673 diethyltoluamide Drugs 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses the synthetic method of a kind of 3-n-butyl amine base ethyl propionate selects n-butylamine and ethyl acrylate to be raw material, and with cerous nitrate as catalyst, reaction is prepared into 3-n-butyl amine base ethyl propionate, compared with prior art, operation is convenient, reaction condition is gentle, cerous nitrate catalyst has cheap and easy to get, favorable solubility in organic solvent, the advantage that toxicity is little, it it is a kind of environmentally friendly catalyst, the yield of product is added on the one hand under the premise ensureing purity, reduce the response time thus improve production efficiency, reduce production cost, commercial production can be largely used on the other hand, reduce the reaction addition product contamination hazard to environment.
Description
Technical field
The present invention relates to organic synthetic method, the synthetic method of especially a kind of 3-n-butyl amine base ethyl propionate.
Background technology
3-n-butyl amine base ethyl propionate is the intermediate of synthesis dimethyl phthalate, dimethyl phthalate is also known as dimethyl phthalate, Yi Moning, it is called for short BAAPE, it is colourless to light yellow clear liquid under room temperature, it it is a kind of wide spectrum, efficient insect repellent, compare with standard mosquito-repellent (DEET), there is toxicity lower, zest is less, safer, the repellent time is longer, to paint and some plastics and synthetic material infringement less, perspire the not distinguishing feature such as facile hydrolysis, it it is the desirable regeneration product of standard mosquito-repellent, its repellent action time is long, can use when Different climate.
Mao Haifang et al. specifically has the synthetic method of the intermediate 3-n-butyl amine base ethyl propionate of dimethyl phthalate in " fragrance flavor and cosmetic " December the 6th phase in 2005 " synthesis of dimethyl phthalate and applied research " test method 2.1, but its generated time is partially long, and be difficult to choose a kind of suitable catalyst that cost is low, environmental pollution is little, it is widely used in commercial production and causes certain obstacle.
Accordingly, it would be desirable to a kind of new technical scheme is to solve the problems referred to above.
Summary of the invention
Goal of the invention: in order to solve the problem existing for prior art, the invention provides a kind of adopt cheap and easy to get, toxicity is little, environmentally friendly catalyst, and the synthetic method of operation convenient 3-n-butyl amine base ethyl propionate.
Technical scheme: for reaching above-mentioned purpose, the synthetic method of the present invention a kind of 3-n-butyl amine base ethyl propionate can adopt the following technical scheme that the synthetic method of a kind of 3-n-butyl amine base ethyl propionate, select n-butylamine to react with ethyl acrylate and be prepared into 3-n-butyl amine base ethyl propionate, specifically comprise the following steps that
(1) in the container with agitating device, reflux, thermometer and two constant pressure funnels, n-butylamine and catalyst cerous nitrate are added；
(2) after being heated to reflux 2-4h, drip a certain amount of ethyl acrylate when stirring, after dropwising, continue stirring insulation reaction 4-8h；
(3) after question response terminates, air-distillation goes out unnecessary n-butylamine, then controls pressure and obtain 3-n-butyl amine base ethyl propionate in 0.67-1.33KPa fractional distillation.
Further, the reaction equation of preparation method is as follows:
Being more highly preferred to, the mol ratio of described n-butylamine and ethyl acrylate is 4:1-5:1.
For accelerating response speed, the molal quantity of described cerous nitrate is the 10% of ethyl acrylate.
Being more highly preferred to, in step (2), the speed of stirring is 100-1000r/min.
Beneficial effect: the synthetic method of a kind of 3-n-butyl amine base ethyl propionate of the present invention selects n-butylamine and ethyl acrylate to be raw material, and with cerous nitrate as catalyst, reaction is prepared into 3-n-butyl amine base ethyl propionate, compared with prior art, operation is convenient, reaction condition is gentle, cerous nitrate catalyst has cheap and easy to get, favorable solubility in organic solvent, the advantage that toxicity is little, it it is a kind of environmentally friendly catalyst, the yield of product is added on the one hand under the premise ensureing purity, reduce the response time thus improve production efficiency, reduce production cost and can be largely used to commercial production on the other hand, reduce the reaction addition product contamination hazard to environment.
Detailed description of the invention
Embodiment 1:
The synthetic method of a kind of 3-n-butyl amine base ethyl propionate, selects n-butylamine to react with ethyl acrylate and is prepared into 3-n-butyl amine base ethyl propionate, and reaction equation is as follows:
Concrete reactions steps is as follows: add n-butylamine and catalyst cerous nitrate in the 500mL four-necked bottle with agitating device, reflux, thermometer and constant pressure funnel；After being heated to reflux 2h, the dropping ethyl acrylate when the speed of 100r/min stirs, after dropwising, continues stirring insulation reaction 4h；Wherein n-butylamine is 4:1 with the mol ratio of ethyl acrylate, and the addition of cerous nitrate is the 10% of ethyl acrylate molal quantity；After question response terminates, air-distillation goes out unnecessary n-butylamine, then controls pressure fractional distillation under 0.67KPa and obtain 3-n-butyl amine base ethyl propionate, and yield is 92.6%, and purity is 99.6%, and the response time is 5h.
Embodiment 2:
The synthetic method of a kind of 3-n-butyl amine base ethyl propionate, selects n-butylamine to react with ethyl acrylate and is prepared into 3-n-butyl amine base ethyl propionate, and reaction equation is as follows:
Concrete reactions steps is as follows: add n-butylamine and catalyst cerous nitrate in the 500mL four-necked bottle with agitating device, reflux, thermometer and constant pressure funnel；After being heated to reflux 4h, the dropping ethyl acrylate when the speed of 1000r/min stirs, after dropwising, continues stirring insulation reaction 8h；Wherein n-butylamine is 3:1 with the mol ratio of ethyl acrylate, and the addition of cerous nitrate is the 10% of ethyl acrylate molal quantity；After question response terminates, air-distillation goes out unnecessary n-butylamine, then controls pressure fractional distillation under 1.33KPa and obtain 3-n-butyl amine base ethyl propionate, and yield is 93.8%, and purity is 99.7%, and the response time is 5h.
Embodiment 3:
The synthetic method of a kind of 3-n-butyl amine base ethyl propionate, selects n-butylamine to react with ethyl acrylate and is prepared into 3-n-butyl amine base ethyl propionate, and reaction equation is as follows:
Concrete reactions steps is as follows: add n-butylamine and catalyst cerous nitrate in the 500mL four-necked bottle with agitating device, reflux, thermometer and constant pressure funnel；After being heated to reflux 3h, the dropping ethyl acrylate when the speed of 500r/min stirs, after dropwising, continues stirring insulation reaction 6h；Wherein n-butylamine is 5:1 with the mol ratio of ethyl acrylate, and the addition of cerous nitrate is the 10% of ethyl acrylate molal quantity；After question response terminates, air-distillation goes out unnecessary n-butylamine, then controls pressure fractional distillation under 1.0KPa and obtain 3-n-butyl amine base ethyl propionate, and yield is 93.2%, and purity is 99.6%, and the response time is 5h.
Should be understood that, above detailed description of the invention is merely to illustrate the present invention rather than restriction the scope of the present invention, after having read the present invention, the amendment of the various equivalent form of values of the present invention is all fallen within the application claims limited range by those skilled in the art.
Claims (1)
1. a synthetic method for 3-n-butyl amine base ethyl propionate, selects n-butylamine to react with ethyl acrylate and is prepared into 3-n-butyl amine base ethyl propionate, it is characterised in that specifically comprise the following steps that
(1) in the container with agitating device, reflux, thermometer and two constant pressure funnels, n-butylamine and catalyst cerous nitrate are added；
(2) after being heated to reflux 2-4h, drip a certain amount of ethyl acrylate when stirring, after dropwising, continue stirring insulation reaction 4-8h；
(3) after question response terminates, air-distillation goes out unnecessary n-butylamine, then controls pressure and obtain 3-n-butyl amine base ethyl propionate in 0.67-1.33KPa fractional distillation；
Wherein, the mol ratio of described n-butylamine and ethyl acrylate is 4:1-5:1, and the molal quantity of described cerous nitrate is the 10% of ethyl acrylate, and in step (2), the speed of stirring is 100-1000r/min.
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| CN103588654B true CN103588654B (en) | 2016-06-29 |
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| CN106565511B (en) * | 2016-10-28 | 2019-03-12 | 苏州健雄职业技术学院 | A kind of preparation method of dimethyl phthalate intermediate 3- n-butyl amine base ethyl propionate |
| CN111848425B (en) * | 2020-07-29 | 2023-03-28 | 中国科学院大学温州研究院(温州生物材料与工程研究所) | Method for selectively synthesizing N-alkyl amino propionate solution |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101613246A (en) * | 2009-07-16 | 2009-12-30 | 合肥工业大学 | A kind of preparation method of N-substituted ethylene diamine derivative |
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| JP2001253844A (en) * | 2000-03-10 | 2001-09-18 | Japan Science & Technology Corp | Method for michael reaction |
| GB0207028D0 (en) * | 2002-03-25 | 2002-05-08 | Charterhouse Therapeutics Ltd | A new synthetic method and novel chemical compounds |
| CN101781223B (en) * | 2009-12-25 | 2013-01-23 | 华东师范大学 | Method for catalytically synthesizing aminated compounds by using carbon-silicon solid acid as catalysts |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101613246A (en) * | 2009-07-16 | 2009-12-30 | 合肥工业大学 | A kind of preparation method of N-substituted ethylene diamine derivative |
Non-Patent Citations (2)
| Title |
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| 7H2O-NaI System Supported in Silica Gel.《J. Org. Chem.》.2001,第66卷9052-9055. * |
| Giuseppe Bartoli等.Conjugate Addition of Amines to α,β-Enones Promoted by CeCl3• * |
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Address after: 215400 No. 1, Jian Xiong Road, science and Education Town, Taicang, Suzhou, Jiangsu Patentee after: SUZHOU CHIEN-SHIUNG INSTITUTE OF TECHNOLOGY Address before: Jianxiong Vocational and Technical College, No.1 Jianxiong Road, Science and Education New City, Taicang City, Suzhou City, Jiangsu Province, 215411 Patentee before: CHIEN-SHIUNG INSTITUTE OF TECHNOLOGY |