CN106349079A - Preparation method of allyl amine mixture - Google Patents
Preparation method of allyl amine mixture Download PDFInfo
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- CN106349079A CN106349079A CN201610745072.8A CN201610745072A CN106349079A CN 106349079 A CN106349079 A CN 106349079A CN 201610745072 A CN201610745072 A CN 201610745072A CN 106349079 A CN106349079 A CN 106349079A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
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Abstract
The invention discloses a preparation method of an allyl amine mixture. The preparation method includes following steps: S1, pouring a catalyst into a reation kettle, adding a certain amount of ammonium hydroxide, rising temperature, and adding chloropropene for ammonolysis reaction; S2, holding the temperature of the step 1, and adding liquid caustic soda; S3, rectifying a reaction product to evaporate water and excessive ammonia; S4, at corresponding temperature, collecting fraction-monoallyl amine; S, at corresponding temperature, collecting fraction-diallyl amine; S6, at corresponding temperature, collecting fraction-trially amine; S7, adding caustic soda flakes into a collected fraction mixture, and performing liquid separation to obtain. The preparation method is mild in reaction condition, ammonium hydroxide is used to replace ammonia in existing methods, and complex ventilation equipment is not needed, so that production cost is saved; by adding the caustic soda flakes, water absorbing effect can be realized, purity of the allyl amine mixture prepared by the method can be effectively improved, and the preparation method is simple to operate, high in yield and worthy of popularization.
Description
Technical field
The present invention relates to chemosynthesis technical field, more particularly, to a kind of preparation method of allyl amine mixture.
Background technology
Allyl amine is colourless liquid, has strong ammonia taste and deeply worried taste, poisonous.Be applied to pharmaceutical intermediate processed and
The intermediate of agricultural chemicals, dyestuff and coating, organic synthesiss and resin modifying agent etc..Can be also used for preparing Amphiphatic high polymer
Polymer etc., is the very important compound of a class.How the preparation method of existing allyl amine, returned with ammonia with allyl chloride
It is obtained in the device of stream, isothiocyanic acid propylene and 20% hydrochloric acid need to be made to react 15h in reflux, product is dense
Add water dilution after sheepshank crystalline substance, then Deca liquid caustic soda steam allylamine, fractional distillation is obtained fine work again to collect crude product, and preparation section is loaded down with trivial details,
Long using equipment complex reaction time, high cost and purity is not high.Based on problem above, the present invention proposes a kind of allyl amine
The preparation method of mixture.
Content of the invention
The invention aims to shortcoming present in solution prior art, and a kind of allyl amine mixture proposing
Preparation method.
A kind of preparation method of allyl amine mixture, comprises the following steps:
S1, catalyst is poured in reactor, add quantitative ammonia, rise high reaction temperature to 35-40 DEG C, then to reactor
Middle interpolation chloropropene, carries out ammonolysis reaction；
S2, the ammonolysis reaction treated in step s1 are finished, and keep 35-40 DEG C temperature-resistant, after constant temperature 20-40min, then to
Add liquid caustic soda in product；
S3, distillation operation is carried out to product in step s2, remove excess of ammonia when rectification temperature is for 35-39 DEG C, in essence
Evaporating temperature is to steam water when 98-104 DEG C；
S4, when the rectification temperature in step s3 is 52-55 DEG C, collection fraction one allyl amine now；
S5, when the rectification temperature in step s3 is 105-110 DEG C, collection fraction diallylamine now；
S6, when the rectification temperature in step s3 is 152-156 DEG C, collection fraction triallylamine now；
S7, the mixture of an allyl amine, diallylamine and triallylamine of collection is added in solid-liquid separating equipment,
Then add piece alkali to carry out a point liquid operation in mixture, obtain final product more pure three kind mixture.
Preferably, the catalyst in described step s1 is lewis acid.
Preferably, the concentration of the ammonia in described step s1 is 28-35%.
Preferably, in described step s1 the addition of ammonia and the addition of catalyst than for 12-17:1.
Preferably, the concentration of the liquid caustic soda in described step s2 is 40-42%.
Preferably, the constant temperature time in described step s2 is 25-35min.
Preferably, the piece alkali addition in described step s6 is 0.2-0.6 times of three kinds of fraction mixture total amounts.
A kind of preparation method of allyl amine mixture proposed by the present invention, is primary raw material using chloropropene and ammonia,
Carry out ammonolysis reaction to be obtained, reaction condition is gentle, replace the ammonia in existing method with ammonia, set without using complicated ventilation
Standby, save production cost, the addition of piece alkali can play water sorption, can effectively improve prepared allyl amine mixture
Purity, simple to operate, yield is high, is worthy to be popularized.
Specific embodiment
With reference to specific embodiment, the present invention is explained further.
Embodiment one
A kind of preparation method of allyl amine mixture proposed by the present invention, comprises the following steps:
S1, lewis acid is poured in reactor, adds the ammonia that the concentration that consumption is 15 times of lewis acid consumption is 30%,
Rise high reaction temperature and add chloropropene to 38 DEG C, then in reactor, carry out ammonolysis reaction；
S2, the ammonolysis reaction treated in step s1 are finished, and keep 38 DEG C temperature-resistant, after constant temperature 25min, then produce to reaction
Adding concentration in thing is 40% liquid caustic soda；
S3, distillation operation is carried out to product in step s2, remove excess of ammonia when rectification temperature is 38 DEG C, in rectification temperature
Water is steamed when spending for 102 DEG C；
S4, when the rectification temperature in step s3 is 53 DEG C, collection fraction one allyl amine now；
S5, when the rectification temperature in step s3 is 108 DEG C, collection fraction diallylamine now；
S6, when the rectification temperature in step s3 is 152 DEG C, collection fraction triallylamine now；
S7, the mixture of an allyl amine, diallylamine and triallylamine of collection is added in solid-liquid separating equipment,
Then add the piece alkali of 0.4 times of mixture amount to carry out a point liquid operation in mixture, obtain final product more pure three kind mixture.
Embodiment two
A kind of preparation method of allyl amine mixture proposed by the present invention, comprises the following steps:
S1, lewis acid is poured in reactor, adds the ammonia that the concentration that consumption is 13 times of lewis acid consumption is 28%,
Rise high reaction temperature and add chloropropene to 36 DEG C, then in reactor, carry out ammonolysis reaction；
S2, the ammonolysis reaction treated in step s1 are finished, and keep 36 DEG C temperature-resistant, after constant temperature 30min, then produce to reaction
Adding concentration in thing is 42% liquid caustic soda；
S3, distillation operation is carried out to product in step s2, remove excess of ammonia when rectification temperature is 36 DEG C, in rectification temperature
Water is steamed when spending for 100 DEG C；
S4, when the rectification temperature in step s3 is 54 DEG C, collection fraction one allyl amine now；
S5, when the rectification temperature in step s3 is 106 DEG C, collection fraction diallylamine now；
S6, when the rectification temperature in step s3 is 154 DEG C, collection fraction triallylamine now；
S7, the mixture of an allyl amine, diallylamine and triallylamine of collection is added in solid-liquid separating equipment,
Then add the piece alkali of 0.2 times of mixture amount to carry out a point liquid operation in mixture, obtain final product more pure three kind mixture.
Embodiment three
A kind of preparation method of allyl amine mixture proposed by the present invention, comprises the following steps:
S1, lewis acid is poured in reactor, adds the ammonia that the concentration that consumption is 17 times of lewis acid consumption is 34%,
Rise high reaction temperature and add chloropropene to 35 DEG C, then in reactor, carry out ammonolysis reaction；
S2, the ammonolysis reaction treated in step s1 are finished, and keep 35 DEG C temperature-resistant, after constant temperature 40min, then produce to reaction
Adding concentration in thing is 41% liquid caustic soda；
S3, distillation operation is carried out to product in step s2, remove excess of ammonia when rectification temperature is 35 DEG C, in rectification temperature
Water is steamed when spending for 99 DEG C；
S4, when the rectification temperature in step s3 is 52 DEG C, collection fraction one allyl amine now；
S5, when the rectification temperature in step s3 is 105 DEG C, collection fraction diallylamine now；
S6, when the rectification temperature in step s3 is 153 DEG C, collection fraction triallylamine now；
S7, the mixture of an allyl amine, diallylamine and triallylamine of collection is added in solid-liquid separating equipment,
Then add the piece alkali of 0.6 times of mixture amount to carry out a point liquid operation in mixture, obtain final product more pure three kind mixture.
Example IV
A kind of preparation method of allyl amine mixture proposed by the present invention, comprises the following steps:
S1, lewis acid is poured in reactor, adds the ammonia that the concentration that consumption is 12 times of lewis acid consumption is 32%,
Rise high reaction temperature and add chloropropene to 39 DEG C, then in reactor, carry out ammonolysis reaction；
S2, the ammonolysis reaction treated in step s1 are finished, and keep 39 DEG C temperature-resistant, after constant temperature 35min, then produce to reaction
Adding concentration in thing is 40% liquid caustic soda；
S3, distillation operation is carried out to product in step s2, remove excess of ammonia when rectification temperature is 37 DEG C, in rectification temperature
Water is steamed when spending for 101 DEG C；
S4, when the rectification temperature in step s3 is 55 DEG C, collection fraction one allyl amine now；
S5, when the rectification temperature in step s3 is 109 DEG C, collection fraction diallylamine now；
S6, when the rectification temperature in step s3 is 155 DEG C, collection fraction triallylamine now；
S7, the mixture of an allyl amine, diallylamine and triallylamine of collection is added in solid-liquid separating equipment,
Then add the piece alkali of 0.3 times of mixture amount to carry out a point liquid operation in mixture, obtain final product more pure three kind mixture.
Embodiment five
A kind of preparation method of allyl amine mixture proposed by the present invention, comprises the following steps:
S1, lewis acid is poured in reactor, adds the ammonia that the concentration that consumption is 16 times of lewis acid consumption is 35%,
Rise high reaction temperature and add chloropropene to 40 DEG C, then in reactor, carry out ammonolysis reaction；
S2, the ammonolysis reaction treated in step s1 are finished, and keep 40 DEG C temperature-resistant, after constant temperature 20min, then produce to reaction
Adding concentration in thing is 42% liquid caustic soda；
S3, distillation operation is carried out to product in step s2, remove excess of ammonia when rectification temperature is 39 DEG C, in rectification temperature
Water is steamed when spending for 103 DEG C；
S4, when the rectification temperature in step s3 is 53 DEG C, collection fraction one allyl amine now；
S5, when the rectification temperature in step s3 is 110 DEG C, collection fraction diallylamine now；
S6, when the rectification temperature in step s3 is 156 DEG C, collection fraction triallylamine now；
S7, the mixture of an allyl amine, diallylamine and triallylamine of collection is added in solid-liquid separating equipment,
Then add the piece alkali of 0.5 times of mixture amount to carry out a point liquid operation in mixture, obtain final product more pure three kind mixture.
The pi-allyl that a kind of preparation method of the allyl amine mixture being proposed according to above-mentioned five groups of embodiments is prepared
The purity of amine blends is compared, and result is as follows:
| Embodiment | Embodiment one | Embodiment two | Embodiment three | Example IV | Embodiment five |
| Purity | 99.3% | 98.6% | 99.9% | 99% | 99.5% |
A kind of preparation method of allyl amine mixture proposed by the present invention, is primary raw material using chloropropene and ammonia, carries out
Ammonolysis reaction is obtained, and reaction condition is gentle, replaces the ammonia in existing method with ammonia, without using complicated aeration equipments,
Save production cost, the addition of piece alkali can play water sorption, can effectively improve the pure of prepared allyl amine mixture
Degree, simple to operate, yield is high, is worthy to be popularized.
The above, the only present invention preferably specific embodiment, but protection scope of the present invention is not limited thereto,
Any those familiar with the art the invention discloses technical scope in, technology according to the present invention scheme and its
Inventive concept equivalent or change in addition, all should be included within the scope of the present invention.
Claims (7)
1. a kind of preparation method of allyl amine mixture is it is characterised in that comprise the following steps:
S1, catalyst is poured in reactor, add quantitative ammonia, rise high reaction temperature to 35-40 DEG C, then to reactor
Middle interpolation chloropropene, carries out ammonolysis reaction；
S2, the ammonolysis reaction treated in step s1 are finished, and keep 35-40 DEG C temperature-resistant, after constant temperature 20-40min, then to
Add liquid caustic soda in product；
S3, distillation operation is carried out to product in step s2, remove excess of ammonia when rectification temperature is for 35-39 DEG C, in essence
Evaporating temperature is to steam water when 98-104 DEG C；
S4, when the rectification temperature in step s3 is 52-55 DEG C, collection fraction one allyl amine now；
S5, when the rectification temperature in step s3 is 105-110 DEG C, collection fraction diallylamine now；
S6, when the rectification temperature in step s3 is 152-156 DEG C, collection fraction triallylamine now；
S7, the mixture of an allyl amine, diallylamine and triallylamine of collection is added in solid-liquid separating equipment,
Then add piece alkali to carry out a point liquid operation in mixture, obtain final product more pure three kind mixture.
2. a kind of preparation method of allyl amine mixture according to claim 1 is it is characterised in that in described step s1
Catalyst be lewis acid.
3. a kind of preparation method of allyl amine mixture according to claim 1 is it is characterised in that in described step s1
Ammonia concentration be 28-35%.
4. a kind of preparation method of allyl amine mixture according to claim 1 is it is characterised in that in described step s1
The addition of the addition of ammonia and catalyst is than for 12-17:1.
5. a kind of preparation method of allyl amine mixture according to claim 1 is it is characterised in that in described step s2
Liquid caustic soda concentration be 40-42%.
6. a kind of preparation method of allyl amine mixture according to claim 1 is it is characterised in that in described step s2
Constant temperature time be 25-35min.
7. a kind of preparation method of allyl amine mixture according to claim 1 is it is characterised in that in described step s6
Piece alkali addition be 0.2-0.6 times of three kinds of fraction mixture total amounts.
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| CN201610745072.8A CN106349079A (en) | 2016-08-29 | 2016-08-29 | Preparation method of allyl amine mixture |
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| CN201610745072.8A CN106349079A (en) | 2016-08-29 | 2016-08-29 | Preparation method of allyl amine mixture |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114394975A (en) * | 2022-01-27 | 2022-04-26 | 黎常宏 | Preparation method of allylamine salt |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS632958A (en) * | 1986-06-20 | 1988-01-07 | Showa Denko Kk | Production of allyl type amine |
| JPH01246244A (en) * | 1988-03-28 | 1989-10-02 | Sumitomo Chem Co Ltd | Production of allylamine having high purity |
| JPH08283209A (en) * | 1995-04-11 | 1996-10-29 | Sumitomo Chem Co Ltd | Production of allylamine |
| CN1962607A (en) * | 2006-11-29 | 2007-05-16 | 杭州新成化学有限公司 | Method for synthesizing allylamine using transfer line reactor |
| CN101346345A (en) * | 2005-12-26 | 2009-01-14 | 住友化学株式会社 | Method for producing primary amine compound |
-
2016
- 2016-08-29 CN CN201610745072.8A patent/CN106349079A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS632958A (en) * | 1986-06-20 | 1988-01-07 | Showa Denko Kk | Production of allyl type amine |
| JPH01246244A (en) * | 1988-03-28 | 1989-10-02 | Sumitomo Chem Co Ltd | Production of allylamine having high purity |
| JPH08283209A (en) * | 1995-04-11 | 1996-10-29 | Sumitomo Chem Co Ltd | Production of allylamine |
| CN101346345A (en) * | 2005-12-26 | 2009-01-14 | 住友化学株式会社 | Method for producing primary amine compound |
| CN1962607A (en) * | 2006-11-29 | 2007-05-16 | 杭州新成化学有限公司 | Method for synthesizing allylamine using transfer line reactor |
Non-Patent Citations (2)
| Title |
|---|
| PAZDZIOCH, WALDEMAR等: "Ammonolysis of allyl chloride by ammonia solution", 《INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH》 * |
| 刘锋等: "烯丙基氯氨解制备烯丙基胺", 《精细化工》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114394975A (en) * | 2022-01-27 | 2022-04-26 | 黎常宏 | Preparation method of allylamine salt |
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