CN109651156A - A method of benzylamine is prepared using micro passage reaction serialization - Google Patents
A method of benzylamine is prepared using micro passage reaction serialization Download PDFInfo
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- CN109651156A CN109651156A CN201910044755.4A CN201910044755A CN109651156A CN 109651156 A CN109651156 A CN 109651156A CN 201910044755 A CN201910044755 A CN 201910044755A CN 109651156 A CN109651156 A CN 109651156A
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- micro passage
- passage reaction
- benzylamine
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- benzyl chloride
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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
Abstract
The invention discloses a kind of methods for preparing benzylamine using micro passage reaction serialization, comprising the following steps: benzaldehyde and benzyl chloride are mixed evenly, it is spare；The mixture of benzaldehyde and benzyl chloride, ammonium hydroxide are passed through in micro passage reaction simultaneously, carry out reacting to obtain intermediate product；Hydrochloric acid is added into intermediate product, is mixed evenly, and stands acidification layering, takes lower layer's substance；Caustic soda is added into lower layer's substance, is mixed evenly, and stands alkalization layering, takes upper layer substance benzylamine crude product, rectification and purification benzylamine crude product obtains pure benzylamine.The invention has the benefit that the method for the present invention for preparing benzylamine is reacted using micro passage reaction, because the heat-transfer capability of micro passage reaction is strong, mixing uniformity is good, substantially reduce the reaction time, the internal diameter of micro passage reaction is small, large specific surface area, material were uniformly mixed with precise proportions moment, improve the efficiency of reaction and the quality of product, keep the selectivity of products therefrom high, yield is high.
Description
Technical field
The present invention relates to the methods for preparing benzylamine, and in particular to a kind of to prepare benzylamine using micro passage reaction serialization
Method.
Background technique
Benzylamine is the important source material chemical intermediate of the chemicals such as some medicine of synthesis, pesticide, dyestuff.It is by the end of at present
Some benzylamine synthesis technologies have only been had developed, but can be used for the few of industrialized production.Current synthetic route mainly can be with
Be classified as several classes: directly from benzaldehyde ammonification, high-pressure hydrogenation is made；Benzaldehyde and benzyl chloride combine ammoniation process；Benzyl chloride and
Methenamine synthetic method.These types of method and process route is long and yield is between 80~86%, the direct ammoniation process yield of benzyl chloride
It between 40~45%, and is both needed to by high pressure ammoniated, high-pressure hydrogenation operation.
Benzyl chloride belongs to Huffman alkylated reaction with reacting for ammonium hydroxide, since the nucleophilicity of reaction product benzylamine is stronger,
Many side reactions are had during the reaction to occur, this not only lowers the yield of benzylamine, and the more difficult purification of product, in benzyl chloride
More benzylamines can be just obtained with needing to consume a large amount of ammonium hydroxide in the traditional synthesis of ammonium hydroxide.And it is the production for improving benzylamine
Rate, it will usually add phase transfer catalyst, even if but traditional handicraft in the case where ammonium hydroxide is excessive and addition phase transfer catalyst,
The yield of benzylamine is also relatively low, which generates that wastewater flow rate is bigger, and cost is relatively high there are ammonium hydroxide consumption is bigger, and
The multistage amine reaction generated in reaction process causes purification of products, separation more difficult, and the yield of benzylamine is lower.
Traditional benzylamine preparation process mainly uses stirred-tank reactor, and there are the reaction time, long, raw material disappears the process
Consumption is big, mixing plant energy consumption is high, more set reaction kettle simultaneous reactions security presence problems, and yield is low, side reaction multi-product content is low
The problems such as separation is difficult, and the pollutant discharge that some pairs of environment and human body damage, therefore one are had during the reaction
Kind improves its reaction yield and product quality, and is badly in need of researching and developing to the synthetic method of the benzylamine of environment and no damage to human body.
Summary of the invention
That the object of the present invention is to provide a kind of production costs is low, yield is high and no pollution to the environment utilizes microchannel plate
The method for answering device serialization to prepare benzylamine.
A method of benzylamine is prepared using micro passage reaction serialization, comprising the following steps:
(1) benzaldehyde and benzyl chloride are mixed evenly, it is spare；
(2) mixture of benzaldehyde and benzyl chloride, ammonium hydroxide are passed through in micro passage reaction simultaneously, react intermediate
Product；
(3) hydrochloric acid is added into intermediate product, is mixed evenly, and stands acidification layering, takes lower layer's substance；Upper layer substance
Matter is benzaldehyde, can be recycled and reused；
(4) caustic soda is added into lower layer's substance, is mixed evenly, and stand alkalization layering, take upper layer substance benzylamine thick
Product, rectification and purification benzylamine crude product obtain pure benzylamine.
Further, in step (1), the benzyl chloride, benzaldehyde, ammonium hydroxide the mass ratio of the material be 1:1-5:5-15.
Further, in step (2), the micro passage reaction is stainless steel micro passage reaction.
Further, in step (2), the internal diameter of the micro passage reaction is 100um-1000um.
Further, in step (2), the length of the micro passage reaction is 1-3m.
Further, in step (2), reaction of the mixture, ammonium hydroxide of benzaldehyde and benzyl chloride in micro passage reaction
Temperature is 50-150 DEG C.
Further, in step (2), reaction of the mixture, ammonium hydroxide of benzaldehyde and benzyl chloride in micro passage reaction
Pressure is 0.2-1.5MPa.
Further, the mixture of benzaldehyde and benzyl chloride, reaction time of the ammonium hydroxide in micro passage reaction are 20-
300s。
Further, in step (3), the volume of added hydrochloric acid is 1.1-1.2 times of intermediate product, added hydrochloric acid it is dense
Degree is 30%.
Further, in step (4): the volume of added caustic soda is 1.1-1.2 times of lower layer's substance, added caustic soda it is dense
Degree is 30%.
The invention has the benefit that a kind of method for preparing benzylamine using micro passage reaction serialization of the present invention
It is reacted using micro passage reaction, because the heat-transfer capability of micro passage reaction is strong, mixing uniformity is good, it is anti-to substantially reduce
Between seasonable, the internal diameter of micro passage reaction is small, large specific surface area, material are uniformly mixed with precise proportions moment, improves reaction
Efficiency and product quality, keep the selectivity of products therefrom high, yield is high.
Furthermore a kind of method for preparing benzylamine using micro passage reaction serialization of the present invention, the raw material used is chlorine
Change benzyl, benzaldehyde, ammonium hydroxide and do not contain Elements in Organic Solvents, and benzaldehyde can with recycling and reusing, by benzyl chloride, benzaldehyde,
Ammonium hydroxide, which is passed through in micro passage reaction, to be reacted, and is then acidified to reaction product, basification, then is purified and can be obtained
Benzylamine, simple production process, and contamination-free and poisonous and harmful substance discharge in process of production, no environment and human body do not cause
Injury.
Specific embodiment
Embodiment one
A method of benzylamine is prepared using micro passage reaction serialization, comprising the following steps:
(1) benzaldehyde and benzyl chloride are mixed evenly, it is spare；
(2) mixture of benzaldehyde and benzyl chloride, ammonium hydroxide are passed through in micro passage reaction simultaneously, react intermediate
Product；
(3) hydrochloric acid is added into intermediate product, is mixed evenly, and stands acidification layering, takes lower layer's substance；
(4) caustic soda is added into lower layer's substance, is mixed evenly, and stand alkalization layering, take upper layer substance benzylamine thick
Product, rectification and purification benzylamine crude product obtain pure benzylamine.
Embodiment two
A method of benzylamine is prepared using micro passage reaction serialization, comprising the following steps:
(1) benzaldehyde and benzyl chloride are mixed evenly, it is spare；
(2) mixture of 10mol benzyl chloride and 10mol benzaldehyde, 50mol ammonium hydroxide are passed through stainless steel microchannel plate simultaneously
Answer in device, and the internal diameter of micro passage reaction is 1000um, the length of micro passage reaction is 1m, reaction time control producing benzaldehyde and
The mixture of benzyl chloride, reaction temperature of the ammonium hydroxide in micro passage reaction are 50 DEG C, control the mixing of benzaldehyde and benzyl chloride
The reaction pressure of object, ammonium hydroxide in micro passage reaction is 0.2MPa, the mixture of control benzaldehyde and benzyl chloride, ammonium hydroxide are micro-
Reaction time in channel reactor is 20s, to the end of reacting intermediate product；
(3) hydrochloric acid that concentration is 30% is added into intermediate product, the volume of added hydrochloric acid is 1.1 times of intermediate product,
It is mixed evenly, and stands acidification layering, take lower layer's substance, and recycle the recycling of upper layer substance benzaldehyde；
(4) caustic soda that concentration is 30% is added into lower layer's substance, the volume of added caustic soda is 1.1 times of lower layer's substance,
It is mixed evenly, and stands alkalization layering, take upper layer substance benzylamine crude product, rectification and purification benzylamine crude product obtains pure benzylamine.
In this reaction process, the use of organic solvent-free, directly simultaneously by the mixture of benzaldehyde and benzyl chloride, ammonium hydroxide
It is passed through in micro passage reaction, is reacted, is then acidified reaction product, basification, then purify to obtain benzylamine, technique
Simply, the utilization rate of raw material is relatively high, and contamination-free and pernicious gas discharge during the reaction, is computed turning for benzyl chloride
Rate 90.0% is changed, is 86.9% by the ultimate yield that benzyl chloride calculates benzylamine.
Embodiment three
A method of benzylamine is prepared using micro passage reaction serialization, comprising the following steps:
(1) benzaldehyde and benzyl chloride are mixed evenly, it is spare；
(2) mixture of 10mol benzyl chloride and 20mol benzaldehyde, 80mol ammonium hydroxide are passed through stainless steel microchannel plate simultaneously
Answer in device, and the internal diameter of micro passage reaction is 800um, the length of micro passage reaction is 2m, reaction time control producing benzaldehyde and
The mixture of benzyl chloride, reaction temperature of the ammonium hydroxide in micro passage reaction are 80 DEG C, control the mixing of benzaldehyde and benzyl chloride
The reaction pressure of object, ammonium hydroxide in micro passage reaction is 0.6MPa, the mixture of control benzaldehyde and benzyl chloride, ammonium hydroxide are micro-
Reaction time in channel reactor is 100s, to the end of reacting intermediate product；
(3) hydrochloric acid that concentration is 30% is added into intermediate product, the volume of added hydrochloric acid is 1.12 times of intermediate product,
It is mixed evenly, and stands acidification layering, take lower layer's substance, and recycle the recycling of upper layer substance benzaldehyde；
(4) caustic soda that concentration is 30% is added into lower layer's substance, the volume of added caustic soda is 1.12 times of lower layer's substance,
It is mixed evenly, and stands alkalization layering, take upper layer substance benzylamine crude product, rectification and purification benzylamine crude product obtains pure benzylamine.
In this reaction process, the use of organic solvent-free, directly simultaneously by the mixture of benzaldehyde and benzyl chloride, ammonium hydroxide
It is passed through in micro passage reaction, is reacted, is then acidified reaction product, basification, then purify to obtain benzylamine, technique
Simply, the utilization rate of raw material is relatively high, and contamination-free and pernicious gas discharge during the reaction, is computed turning for benzyl chloride
Rate 85.5% is changed, is 82.0% by the ultimate yield that benzyl chloride calculates benzylamine.
Example IV
A method of benzylamine is prepared using micro passage reaction serialization, comprising the following steps:
(1) benzaldehyde and benzyl chloride are mixed evenly, it is spare；
(2) mixture of 10mol benzyl chloride and 50mol benzaldehyde, 100mol ammonium hydroxide are passed through stainless steel microchannel simultaneously
In reactor, and the internal diameter of micro passage reaction is 500um, and the length of micro passage reaction is 2m, reacts time control producing benzaldehyde
Be 120 DEG C with the mixture of benzyl chloride, reaction temperature of the ammonium hydroxide in micro passage reaction, control benzaldehyde and benzyl chloride it is mixed
Close object, mixture, the ammonium hydroxide that reaction pressure of the ammonium hydroxide in micro passage reaction is 1.1MPa, control benzaldehyde and benzyl chloride exist
Reaction time in micro passage reaction is 200s, to the end of reacting intermediate product；
(3) hydrochloric acid that concentration is 30% is added into intermediate product, the volume of added hydrochloric acid is 1.15 times of intermediate product,
It is mixed evenly, and stands acidification layering, take lower layer's substance, and recycle the recycling of upper layer substance benzaldehyde；
(4) caustic soda that concentration is 30% is added into lower layer's substance, the volume of added caustic soda is 1.15 times of lower layer's substance,
It is mixed evenly, and stands alkalization layering, take upper layer substance benzylamine crude product, rectification and purification benzylamine crude product obtains pure benzylamine.
In this reaction process, the use of organic solvent-free, directly simultaneously by the mixture of benzaldehyde and benzyl chloride, ammonium hydroxide
It is passed through in micro passage reaction, is reacted, is then acidified reaction product, basification, then purify to obtain benzylamine, technique
Simply, the utilization rate of raw material is relatively high, and contamination-free and pernicious gas discharge during the reaction, is computed turning for benzyl chloride
Rate 96.8% is changed, is 94.1% by the ultimate yield that benzyl chloride calculates benzylamine.
Embodiment five
A method of benzylamine is prepared using micro passage reaction serialization, comprising the following steps:
(1) benzaldehyde and benzyl chloride are mixed evenly, it is spare；
(2) mixture of 10mol benzyl chloride and 50mol benzaldehyde, 150mol ammonium hydroxide are passed through stainless steel microchannel simultaneously
In reactor, and the internal diameter of micro passage reaction is 100um, and the length of micro passage reaction is 3m, reacts time control producing benzaldehyde
Be 150 DEG C with the mixture of benzyl chloride, reaction temperature of the ammonium hydroxide in micro passage reaction, control benzaldehyde and benzyl chloride it is mixed
Close object, mixture, the ammonium hydroxide that reaction pressure of the ammonium hydroxide in micro passage reaction is 1.5MPa, control benzaldehyde and benzyl chloride exist
Reaction time in micro passage reaction is 300s, to the end of reacting intermediate product；
(3) hydrochloric acid that concentration is 30% is added into intermediate product, the volume of added hydrochloric acid is 1.2 times of intermediate product,
It is mixed evenly, and stands acidification layering, take lower layer's substance, and recycle the recycling of upper layer substance benzaldehyde；
(4) caustic soda that concentration is 30% is added into lower layer's substance, the volume of added caustic soda is 1.2 times of lower layer's substance,
It is mixed evenly, and stands alkalization layering, take upper layer substance benzylamine crude product, rectification and purification benzylamine crude product obtains pure benzylamine.
In this reaction process, the use of organic solvent-free, directly simultaneously by the mixture of benzaldehyde and benzyl chloride, ammonium hydroxide
It is passed through in micro passage reaction, is reacted, is then acidified reaction product, basification, then purify to obtain benzylamine, technique
Simply, the utilization rate of raw material is relatively high, and contamination-free and pernicious gas discharge during the reaction, is computed turning for benzyl chloride
Rate 98.3% is changed, is 95.6% by the ultimate yield that benzyl chloride calculates benzylamine.
The present invention is not limited to above-mentioned preferred forms, anyone can show that other are various under the inspiration of the present invention
The product of form, however, make any variation in its details, it is all that there is technical solution identical or similar to the present application,
It is within the scope of the present invention.
Claims (10)
1. a kind of method for preparing benzylamine using micro passage reaction serialization, which comprises the following steps:
(1) benzaldehyde and benzyl chloride are mixed evenly, it is spare；
(2) mixture of benzaldehyde and benzyl chloride, ammonium hydroxide are passed through in micro passage reaction simultaneously, carry out reacting to obtain intermediate production
Object；
(3) hydrochloric acid is added into intermediate product, is mixed evenly, and stands acidification layering, takes lower layer's substance；
(4) caustic soda is added into lower layer's substance, is mixed evenly, and stand alkalization layering, take upper layer substance benzylamine crude product, essence
It evaporates purification benzylamine crude product and obtains pure benzylamine.
2. a kind of method for preparing benzylamine using micro passage reaction serialization according to claim 1, which is characterized in that step
Suddenly in (1), the benzyl chloride, benzaldehyde, ammonium hydroxide the mass ratio of the material be 1:1-5:5-15.
3. a kind of method for preparing benzylamine using micro passage reaction serialization according to claim 1, which is characterized in that step
Suddenly in (2), the micro passage reaction is stainless steel micro passage reaction.
4. a kind of method for preparing benzylamine using micro passage reaction serialization according to claim 1, which is characterized in that step
Suddenly in (2), the internal diameter of the micro passage reaction is 100um-1000um.
5. a kind of method for preparing benzylamine using micro passage reaction serialization according to claim 1, which is characterized in that step
Suddenly in (2), the length of the micro passage reaction is 1-3m.
6. a kind of method for preparing benzylamine using micro passage reaction serialization according to claim 1, which is characterized in that step
Suddenly in (2), the mixture of benzaldehyde and benzyl chloride, reaction temperature of the ammonium hydroxide in micro passage reaction are 50-150 DEG C.
7. a kind of method for preparing benzylamine using micro passage reaction serialization according to claim 1, which is characterized in that step
Suddenly in (2), the mixture of benzaldehyde and benzyl chloride, reaction pressure of the ammonium hydroxide in micro passage reaction are 0.2-1.5MPa.
8. a kind of method for preparing benzylamine using micro passage reaction serialization according to claim 1, which is characterized in that benzene
The mixture of formaldehyde and benzyl chloride, reaction time of the ammonium hydroxide in micro passage reaction are 20-300s.
9. a kind of method for preparing benzylamine using micro passage reaction serialization according to claim 1, which is characterized in that step
Suddenly in (3), the volume of added hydrochloric acid is 1.1-1.2 times of intermediate product, and the concentration of added hydrochloric acid is 30%.
10. a kind of method for preparing benzylamine using micro passage reaction serialization according to claim 1, which is characterized in that
In step (4): the volume of added caustic soda is 1.1-1.2 times of lower layer's substance, and the concentration of added caustic soda is 30%.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57174478A (en) * | 1981-04-22 | 1982-10-27 | Asahi Chem Ind Co Ltd | Electrolytically reducing method |
| US5210303A (en) * | 1990-04-20 | 1993-05-11 | Ihara Chemical Industry Co., Ltd. | Process for producing benzylamines |
| CN101370765A (en) * | 2005-12-15 | 2009-02-18 | 住友化学株式会社 | Method for selectively producing primary amine |
| CN101607914A (en) * | 2009-04-24 | 2009-12-23 | 江苏剑牌农药化工有限公司 | Simple method for preparing to tert-butyl benzyl amine |
| CN108623468A (en) * | 2018-06-22 | 2018-10-09 | 贵州微化科技有限公司 | The method that benzylamine is prepared using microchannel reaction unit |
-
2019
- 2019-01-17 CN CN201910044755.4A patent/CN109651156A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57174478A (en) * | 1981-04-22 | 1982-10-27 | Asahi Chem Ind Co Ltd | Electrolytically reducing method |
| US5210303A (en) * | 1990-04-20 | 1993-05-11 | Ihara Chemical Industry Co., Ltd. | Process for producing benzylamines |
| CN101370765A (en) * | 2005-12-15 | 2009-02-18 | 住友化学株式会社 | Method for selectively producing primary amine |
| CN101607914A (en) * | 2009-04-24 | 2009-12-23 | 江苏剑牌农药化工有限公司 | Simple method for preparing to tert-butyl benzyl amine |
| CN108623468A (en) * | 2018-06-22 | 2018-10-09 | 贵州微化科技有限公司 | The method that benzylamine is prepared using microchannel reaction unit |
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