CN107778325B - Preparation method of N- [3- (trimethoxysilyl) propyl ] N-butylamine - Google Patents

Preparation method of N- [3- (trimethoxysilyl) propyl ] N-butylamine Download PDF

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CN107778325B
CN107778325B CN201610744018.1A CN201610744018A CN107778325B CN 107778325 B CN107778325 B CN 107778325B CN 201610744018 A CN201610744018 A CN 201610744018A CN 107778325 B CN107778325 B CN 107778325B
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butylamine
reaction
trimethoxysilyl
propyl
ethylenediamine
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CN107778325A (en
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卢云龙
岳立
王剑
时二波
刘磊
陈晓华
戴建才
刘祖峰
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Zhangjiagang Guotai Huarong New Chemical Materials Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888

Abstract

The invention discloses a preparation method of N- [3- (trimethoxysilyl) propyl ] N-butylamine, which comprises the following steps: (1) adding N-butylamine and chloropropyltrimethoxysilane into a reaction kettle, stirring and reacting at 80-90 ℃ to obtain a reaction solution containing N- [3- (trimethoxysilyl) propyl ] N-butylamine, N-butylamine hydrochloride and excessive N-butylamine; (2) adding ethylenediamine at the temperature of 40-80 ℃, stirring to enable the ethylenediamine and N-butylamine hydrochloride to perform sufficient displacement reaction to generate ethylenediamine hydrochloride, then keeping the temperature at the temperature of 40-70 ℃, standing, and separating liquid to obtain an upper layer reaction liquid containing N- [3- (trimethoxysilyl) propyl ] N-butylamine and a lower layer reaction liquid containing the ethylenediamine hydrochloride; (3) and (3) carrying out reduced pressure distillation on the upper layer reaction liquid obtained from the liquid separation in the step (2) to obtain N- [3- (trimethoxysilyl) propyl ] N-butylamine. The invention has simple process, and the obtained product has the yield of more than 88 percent and the purity of more than 99 percent.

Description

Preparation method of N- [3- (trimethoxysilyl) propyl ] N-butylamine
Technical Field
The invention relates to the field of organic chemical industry, in particular to a preparation method of N- [3- (trimethoxysilyl) propyl ] N-butylamine.
Background
Silane coupling agents are a class of compounds with great features in organic silicon chemistry, and are widely applied to various fields of national economy because the silane coupling agents not only contain carbon functional groups capable of reacting with organic polymers, but also have the characteristics of easy hydrolysis and polycondensation, and simultaneously can form silicon functional groups chemically bonded with the surface of inorganic materials. N- [3- (trimethoxysilyl) propyl ] N-butylamine serving as a novel amino silane coupling agent can replace KH-550 to be used for treating products such as inorganic powder, glass fiber and the like, can obviously improve the mechanical properties such as hardness, toughness and the like of a composite material, can also be applied to the fields of textile auxiliary agents, adhesives, tackifiers of coatings and the like, and improves the properties such as cohesiveness, weather resistance, yellowing resistance, flexibility and the like of the products.
Currently, there are two general methods for preparing N- [3- (trimethoxysilyl) propyl ] N-butylamine: one is the hydrosilylation by a hydroalkoxysilane with n-butyltomiline, which has the disadvantages: the adopted raw materials and the catalyst are expensive, and the obtained product has two isomers which are not easy to separate, so that the purity of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is low, and the purity of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is lower than 97 percent. Another is the reaction of haloalkylalkoxysilanes with n-butylamine, which has the disadvantage that: in the reaction liquid of the method, the solubility of N-butylamine hydrochloride in N-butylamine is very high, the treatment of the reaction liquid is a relatively big problem, at present, a sodium alkoxide treatment process is generally adopted to treat the N-butylamine hydrochloride, but the process can cause more solid waste and is not friendly to the environment, when the sodium alkoxide is introduced, in order to ensure that the N-butylamine hydrochloride in the reaction liquid is thoroughly treated, the addition amount of the sodium alkoxide is generally excessive, the excessive sodium alkoxide is not easy to remove and affects rectification, a filtrate has an obvious decomposition impurity peak next to a main peak during rectification, the rectification separation is difficult to carry out, the purity of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is low, the purity of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is lower than 97 percent, the sodium alkoxide treatment is simultaneously used, the solid-liquid separation is involved, but filter residues have certain moisture content, further, the yield of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is low, and the yield of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is lower than 80 percent.
Disclosure of Invention
The invention aims to provide a preparation method of N- [3- (trimethoxysilyl) propyl ] N-butylamine, which has the advantages of low cost, high yield, high purity, simple operation and environmental friendliness.
In order to achieve the purpose, the invention adopts the following technical scheme: the preparation method of the N- [3- (trimethoxysilyl) propyl ] N-butylamine comprises the following steps:
(1) adding N-butylamine and chloropropyltrimethoxysilane into a reaction kettle, slowly heating to 80-90 ℃ while stirring, stirring and reacting at the reaction temperature to obtain a reaction solution containing N- [3- (trimethoxysilyl) propyl ] N-butylamine, N-butylamine hydrochloride and excessive N-butylamine;
(2) controlling the temperature in the reaction kettle to be 40-80 ℃, adding ethylenediamine into the reaction kettle, stirring to enable the ethylenediamine and N-butylamine hydrochloride to perform sufficient displacement reaction to generate ethylenediamine hydrochloride, keeping the temperature at 40-70 ℃, standing, and separating liquid to obtain an upper layer reaction liquid containing N- [3- (trimethoxysilyl) propyl ] N-butylamine and a lower layer reaction liquid containing the ethylenediamine hydrochloride;
(3) and (3) carrying out reduced pressure distillation on the upper layer reaction liquid obtained from the liquid separation in the step (2) to obtain N- [3- (trimethoxysilyl) propyl ] N-butylamine.
Further, the aforementioned process for producing N- [3- (trimethoxysilyl) propyl ] N-butylamine, wherein: the molar ratio of n-butylamine to chloropropyltrimethoxysilane added in the step (1) is (3-5) to 1.
Further, the aforementioned process for producing N- [3- (trimethoxysilyl) propyl ] N-butylamine, wherein: in the step (1), the molar ratio of n-butylamine to chloropropyltrimethoxysilane is 4: 1.
Further, the aforementioned process for producing N- [3- (trimethoxysilyl) propyl ] N-butylamine, wherein: the reaction time of the step (1) is controlled to be 8-16 h.
Further, the aforementioned process for producing N- [3- (trimethoxysilyl) propyl ] N-butylamine, wherein: the reaction time of the step (1) is controlled to be 10-11 h.
Further, the aforementioned process for producing N- [3- (trimethoxysilyl) propyl ] N-butylamine, wherein: the molar ratio of the ethylenediamine added into the reaction kettle in the step (2) to the n-butylamine hydrochloride generated in the step (1) is (1-1.3): 1.
Further, the aforementioned process for producing N- [3- (trimethoxysilyl) propyl ] N-butylamine, wherein: the molar ratio of the ethylenediamine added into the reaction kettle in the step (2) to the n-butylamine hydrochloride generated in the step (1) is 1.1: 1.
Further, the aforementioned process for producing N- [3- (trimethoxysilyl) propyl ] N-butylamine, wherein: and (3) controlling the temperature of the heat preservation and standing in the step (2) to be 60-65 ℃, and controlling the time of the heat preservation and standing in the step (2) to be 3-6 h.
Further, the aforementioned process for producing N- [3- (trimethoxysilyl) propyl ] N-butylamine, wherein: and (3) adding ethylenediamine into the step (2) and stirring for 1-2 hours.
Further, the aforementioned process for producing N- [3- (trimethoxysilyl) propyl ] N-butylamine, wherein: after the reaction in the step (1) is finished, distilling out not less than 30% of n-butylamine in the reaction liquid under a slight negative pressure, and then performing the step (2).
Through the implementation of the technical scheme, the invention has the beneficial effects that: the yield of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is more than 88 percent, the purity of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is more than 99 percent, the cost is low, the operation is simple, and the method is environment-friendly.
Detailed Description
The present invention will be further described with reference to the following specific examples.
Example one
The preparation method of N- [3- (trimethoxysilyl) propyl ] N-butylamine comprises the following steps:
(1) firstly, 2740g of N-butylamine and 1489g of chloropropyl trimethoxy silane are added into a reaction kettle according to the feeding proportion that the molar ratio of the N-butylamine to the chloropropyl trimethoxy silane is 5:1, then the temperature is slowly raised to (85-90) ℃ while stirring, the mixture is stirred at the reaction temperature and reacts for 8 hours to obtain a reaction solution containing N- [3- (trimethoxysilyl) propyl ] N-butylamine, N-butylamine hydrochloride and excessive N-butylamine, and 1923g of N-butylamine in the reaction solution is distilled under a slight negative pressure after the reaction is finished;
(2) controlling the temperature in the reaction kettle at 70 ℃, adding 540g of ethylenediamine into the reaction kettle according to the feeding proportion that the molar ratio of the ethylenediamine to the N-butylamine hydrochloride generated in the step (1) is 1.2:1, stirring for 1h to enable the ethylenediamine and the N-butylamine hydrochloride to perform sufficient displacement reaction to generate ethylenediamine hydrochloride, keeping the temperature at 65 ℃ after stirring is finished, standing for 6h, and separating liquid to obtain 1943 g of an upper layer reaction liquid containing N- [3- (trimethoxysilyl) propyl ] N-butylamine, N-butylamine and ethylenediamine and 865 g of a lower layer reaction liquid containing the ethylenediamine hydrochloride;
(3) then, the upper layer reaction solution obtained by fractionating in step (2) was distilled under reduced pressure to obtain 1612 g of N- [3- (trimethoxysilyl) propyl ] N-butylamine.
In the embodiment, after the reaction in the step (1) is finished, not less than 30% of n-butylamine in the reaction solution is distilled under a slight negative pressure, and then the operation procedure in the step (2) is performed, so that the displacement reaction in the step (2) can be more thorough, and the purity and yield of the product can be improved; and when the upper layer reaction liquid obtained by the liquid separation in the step (2) is subjected to reduced pressure distillation, no obvious impurity decomposition peak exists, so that the purity and yield of the N- [3- (trimethoxysilyl) propyl ] N-butylamine distilled under reduced pressure are greatly improved, in the embodiment, the purity of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is 99.6%, and the yield of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is 91.5%.
Example two
The preparation method of N- [3- (trimethoxysilyl) propyl ] N-butylamine comprises the following steps:
(1) adding 1645g of N-butylamine and 1489g of chloropropyl trimethoxy silane into a reaction kettle according to the molar ratio of the N-butylamine to the chloropropyl trimethoxy silane being 3:1, slowly heating to 80-85 ℃ while stirring, stirring at the reaction temperature, reacting for 16 hours to obtain a reaction solution containing N- [3- (trimethoxysilyl) propyl ] N-butylamine, N-butylamine hydrochloride and excessive N-butylamine, and distilling 873 g of N-butylamine in the reaction solution under a slight negative pressure after the reaction is finished;
(2) controlling the temperature in the reaction kettle at 45 ℃, adding 495g of ethylenediamine into the reaction kettle according to the feeding proportion that the molar ratio of the ethylenediamine to the N-butylamine hydrochloride generated in the step (1) is 1.1:1, stirring for 2 hours to enable the ethylenediamine and the N-butylamine hydrochloride to perform sufficient displacement reaction to generate ethylenediamine hydrochloride, keeping the temperature at 65 ℃ after stirring is finished, standing for 3 hours, and separating liquid to obtain 1896 g of upper layer reaction liquid containing N- [3- (trimethoxysilyl) propyl ] N-butylamine, ethylenediamine and N-butylamine and 823 g of lower layer reaction liquid containing the ethylenediamine hydrochloride;
(3) then, the upper layer reaction solution obtained from the separation in the step (2) was distilled under reduced pressure to obtain 1558g of N- [3- (trimethoxysilyl) propyl ] N-butylamine.
In the embodiment, after the reaction in the step (1) is finished, not less than 30% of n-butylamine in the reaction solution is distilled under a slight negative pressure, and then the operation procedure in the step (2) is performed, so that the displacement reaction in the step (2) can be more thorough, and the purity and yield of the product can be improved; and when the upper layer reaction liquid obtained by the liquid separation in the step (2) is subjected to reduced pressure distillation, no obvious impurity decomposition peak exists, so that the purity and yield of the N- [3- (trimethoxysilyl) propyl ] N-butylamine obtained by reduced pressure distillation are greatly improved, in the embodiment, the purity of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is 99.1%, and the yield of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is 88.4%.
EXAMPLE III
The preparation method of N- [3- (trimethoxysilyl) propyl ] N-butylamine comprises the following steps:
(1) adding 2190g of N-butylamine and 1489g of chloropropyl trimethoxy silane into a reaction kettle according to the feeding proportion that the molar ratio of the N-butylamine to the chloropropyl trimethoxy silane is 4:1, slowly heating to (85-90) DEG C while stirring, stirring at the reaction temperature, reacting for 8 hours to obtain a reaction solution containing N- [3- (trimethoxysilyl) propyl ] N-butylamine, N-butylamine hydrochloride and excessive N-butylamine, and distilling 1423 g of N-butylamine in the reaction solution under a slight negative pressure after the reaction is finished;
(2) controlling the temperature in the reaction kettle at 60 ℃, adding 495g of ethylenediamine into the reaction kettle according to the feeding proportion that the molar ratio of the ethylenediamine to the N-butylamine hydrochloride generated in the step (1) is 1.1:1, stirring for 2 hours to enable the ethylenediamine and the N-butylamine hydrochloride to perform sufficient displacement reaction to generate ethylenediamine hydrochloride, keeping the temperature at 60 ℃ after stirring is finished, standing for 4 hours, and separating liquid to obtain 1914 g of upper-layer reaction liquid containing N- [3- (trimethoxysilyl) propyl ] N-butylamine, N-butylamine and ethylenediamine and 816g of lower-layer reaction liquid containing the ethylenediamine hydrochloride;
(3) then, the upper layer reaction solution obtained by fractionating in step (2) was distilled under reduced pressure to obtain 1575g of N- [3- (trimethoxysilyl) propyl ] N-butylamine.
In the embodiment, after the reaction in the step (1) is finished, not less than 30% of n-butylamine in the reaction solution is distilled under a slight negative pressure, and then the operation procedure in the step (2) is performed, so that the displacement reaction in the step (2) can be more thorough, and the purity and yield of the product can be improved; and when the upper layer reaction liquid obtained by the liquid separation in the step (2) is subjected to reduced pressure distillation, no obvious impurity decomposition peak exists, so that the purity and yield of the N- [3- (trimethoxysilyl) propyl ] N-butylamine distilled under reduced pressure are greatly improved, in the embodiment, the purity of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is 99.3%, and the yield of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is 89.4%.
Example four
The preparation method of N- [3- (trimethoxysilyl) propyl ] N-butylamine comprises the following steps:
(1) firstly, 2740g of N-butylamine and 1489g of chloropropyl trimethoxy silane are added into a reaction kettle according to the feeding proportion that the molar ratio of the N-butylamine to the chloropropyl trimethoxy silane is 5:1, then the temperature is slowly raised to (85-90) ℃ while stirring, the mixture is stirred at the reaction temperature and reacts for 8 hours to obtain a reaction solution containing N- [3- (trimethoxysilyl) propyl ] N-butylamine, N-butylamine hydrochloride and excessive N-butylamine, and 1830 g of N-butylamine in the reaction solution is distilled under a slight negative pressure after the reaction is finished;
(2) controlling the temperature in the reaction kettle to be 80 ℃, adding 586g of ethylenediamine into the reaction kettle according to the feeding proportion that the molar ratio of the ethylenediamine to the N-butylamine hydrochloride generated in the step (1) is 1.3:1, stirring for 2 hours to enable the ethylenediamine and the N-butylamine hydrochloride to carry out sufficient displacement reaction to generate ethylenediamine hydrochloride, keeping the temperature at 70 ℃ after stirring is finished, standing for 6 hours, and then separating liquid to obtain 2110g of upper layer reaction liquid containing N- [3- (trimethoxysilyl) propyl ] N-butylamine, N-butylamine and ethylenediamine and 875g of lower layer reaction liquid containing the ethylenediamine hydrochloride;
(3) then, the upper layer reaction solution obtained by fractionating in step (2) was distilled under reduced pressure to obtain 1567g of N- [3- (trimethoxysilyl) propyl ] N-butylamine.
In the embodiment, after the reaction in the step (1) is finished, not less than 30% of n-butylamine in the reaction solution is distilled under a slight negative pressure, and then the operation procedure in the step (2) is performed, so that the displacement reaction in the step (2) can be more thorough, and the purity and yield of the product can be improved; and when the upper layer reaction liquid obtained by the liquid separation in the step (2) is subjected to reduced pressure distillation, no obvious impurity decomposition peak exists, so that the purity and yield of the N- [3- (trimethoxysilyl) propyl ] N-butylamine obtained by reduced pressure distillation are greatly improved, in the embodiment, the purity of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is 99.23%, and the yield of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is 88.9%.
EXAMPLE five
The preparation method of N- [3- (trimethoxysilyl) propyl ] N-butylamine comprises the following steps:
(1) adding 1645g of N-butylamine and 1489g of chloropropyl trimethoxy silane into a reaction kettle according to the molar ratio of the N-butylamine to the chloropropyl trimethoxy silane being 3:1, slowly heating to 80-85 ℃ while stirring, stirring at the reaction temperature, reacting for 15 hours to obtain a reaction solution containing N- [3- (trimethoxysilyl) propyl ] N-butylamine, N-butylamine hydrochloride and excessive N-butylamine, and distilling 873 g of N-butylamine in the reaction solution under a slight negative pressure after the reaction is finished;
(2) then controlling the temperature in the reaction kettle at 40 ℃, adding 451g of ethylenediamine into the reaction kettle according to the feeding proportion that the molar ratio of the ethylenediamine to the N-butylamine hydrochloride generated in the step (1) is 1:1, stirring for 1h to enable the ethylenediamine and the N-butylamine hydrochloride to perform sufficient displacement reaction to generate ethylenediamine hydrochloride, after stirring is finished, keeping the temperature and standing for 3h at 40 ℃, and then separating liquid to obtain 1981g of upper-layer reaction liquid containing N- [3- (trimethoxysilyl) propyl ] N-butylamine and 731g of lower-layer reaction liquid containing the ethylenediamine hydrochloride;
(3) then, the upper layer reaction solution obtained by fractionating in step (2) was distilled under reduced pressure to obtain 1560g of N- [3- (trimethoxysilyl) propyl ] N-butylamine.
In the embodiment, after the reaction in the step (1) is finished, not less than 30% of n-butylamine in the reaction solution is distilled under a slight negative pressure, and then the operation procedure in the step (2) is performed, so that the displacement reaction in the step (2) can be more thorough, and the purity and yield of the product can be improved; and when the upper layer reaction liquid obtained by the liquid separation in the step (2) is subjected to reduced pressure distillation, no obvious impurity decomposition peak exists, so that the purity and yield of the N- [3- (trimethoxysilyl) propyl ] N-butylamine obtained by reduced pressure distillation are greatly improved, in the embodiment, the purity of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is 99.3%, and the yield of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is 88.5%.
EXAMPLE six
The preparation method of N- [3- (trimethoxysilyl) propyl ] N-butylamine comprises the following steps:
(1) adding 2190g of N-butylamine and 1489g of chloropropyl trimethoxy silane into a reaction kettle according to the feeding proportion that the molar ratio of the N-butylamine to the chloropropyl trimethoxy silane is 4:1, slowly heating to (85-90) DEG C while stirring, stirring at the reaction temperature, reacting for 10 hours to obtain a reaction solution containing N- [3- (trimethoxysilyl) propyl ] N-butylamine, N-butylamine hydrochloride and excessive N-butylamine, and distilling 1401 g of N-butylamine in the reaction solution under a slight negative pressure after the reaction is finished;
(2) controlling the temperature in the reaction kettle at 60 ℃, adding 495g of ethylenediamine into the reaction kettle according to the feeding proportion that the molar ratio of the ethylenediamine to the N-butylamine hydrochloride generated in the step (1) is 1.1:1, stirring for 1h to enable the ethylenediamine and the N-butylamine hydrochloride to perform sufficient displacement reaction to generate ethylenediamine hydrochloride, keeping the temperature at 60 ℃ after stirring is finished, standing for 4h, and separating liquid to obtain 1925g of upper layer reaction liquid containing N- [3- (trimethoxysilyl) propyl ] N-butylamine, N-butylamine and ethylenediamine and 816g of lower layer reaction liquid containing the ethylenediamine hydrochloride;
(3) then, the upper layer reaction solution obtained by the separation in the step (2) was distilled under reduced pressure to obtain 1588g of N- [3- (trimethoxysilyl) propyl ] N-butylamine.
In the embodiment, after the reaction in the step (1) is finished, not less than 30% of n-butylamine in the reaction solution is distilled under a slight negative pressure, and then the operation procedure in the step (2) is performed, so that the displacement reaction in the step (2) can be more thorough, and the purity and yield of the product can be improved; and when the upper layer reaction liquid obtained by the liquid separation in the step (2) is subjected to reduced pressure distillation, no obvious impurity decomposition peak exists, so that the purity and yield of the N- [3- (trimethoxysilyl) propyl ] N-butylamine distilled under reduced pressure are greatly improved, in the embodiment, the purity of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is 99.35%, and the yield of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is 90.1%.
EXAMPLE seven
The preparation method of N- [3- (trimethoxysilyl) propyl ] N-butylamine comprises the following steps:
(1) adding 2190g of N-butylamine and 1489g of chloropropyl trimethoxy silane into a reaction kettle according to the feeding proportion that the molar ratio of the N-butylamine to the chloropropyl trimethoxy silane is 4:1, slowly heating to 80-85 ℃ while stirring, stirring at the reaction temperature, reacting for 13 hours to obtain a reaction solution containing N- [3- (trimethoxysilyl) propyl ] N-butylamine, N-butylamine hydrochloride and excessive N-butylamine, and distilling 1419g of N-butylamine in the reaction solution under a slight negative pressure after the reaction is finished;
(2) controlling the temperature in the reaction kettle to 65 ℃, adding 495g of ethylenediamine into the reaction kettle according to the feeding proportion that the molar ratio of the ethylenediamine to the N-butylamine hydrochloride generated in the step (1) is 1.1:1, stirring for 2 hours to enable the ethylenediamine and the N-butylamine hydrochloride to perform sufficient displacement reaction to generate ethylenediamine hydrochloride, keeping the temperature at 50 ℃ after stirring is finished, standing for 4 hours, and separating liquid to obtain 1917 g of upper-layer reaction liquid containing N- [3- (trimethoxysilyl) propyl ] N-butylamine, N-butylamine and ethylenediamine and 820 g of lower-layer reaction liquid containing the ethylenediamine hydrochloride;
(3) then, the upper layer reaction solution obtained by fractionating in step (2) was distilled under reduced pressure to obtain 1591g of N- [3- (trimethoxysilyl) propyl ] N-butylamine.
In the embodiment, after the reaction in the step (1) is finished, not less than 30% of n-butylamine in the reaction solution is distilled under a slight negative pressure, and then the operation procedure in the step (2) is performed, so that the displacement reaction in the step (2) can be more thorough, and the purity and yield of the product can be improved; and when the upper layer reaction liquid obtained by the liquid separation in the step (2) is subjected to reduced pressure distillation, no obvious impurity decomposition peak exists, so that the purity and yield of the N- [3- (trimethoxysilyl) propyl ] N-butylamine distilled under reduced pressure are greatly improved, in the embodiment, the purity of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is 99.31%, and the yield of the N- [3- (trimethoxysilyl) propyl ] N-butylamine is 90.3%.

Claims (1)

  1. A method for preparing N- [3- (trimethoxysilyl) propyl ] N-butylamine, which is characterized by comprising the following steps: the method comprises the following steps:
    (1) adding N-butylamine and chloropropyltrimethoxysilane into a reaction kettle, slowly heating to 80-90 ℃ while stirring, stirring at the reaction temperature, and reacting to obtain a reaction solution containing N- [3- (trimethoxysilyl) propyl ] N-butylamine, N-butylamine hydrochloride and excessive N-butylamine; the mol ratio of n-butylamine to chloropropyltrimethoxysilane added in the step (1) is 4: 1; controlling the reaction time of the step (1) to be 10-11 h; after the reaction is finished, distilling at a slight negative pressure to obtain not less than 30% of n-butylamine in the reaction solution, and then performing the step (2);
    (2) controlling the temperature in the reaction kettle to be 40-80 ℃, then adding ethylenediamine into the reaction kettle, stirring to enable the ethylenediamine and N-butylamine hydrochloride to perform sufficient displacement reaction to generate ethylenediamine hydrochloride, then keeping the temperature at 40-70 ℃, standing, and separating liquid to obtain an upper layer reaction liquid containing N- [3- (trimethoxysilyl) propyl ] N-butylamine and a lower layer reaction liquid containing the ethylenediamine hydrochloride; the molar ratio of the ethylenediamine added into the reaction kettle in the step (2) to the n-butylamine hydrochloride generated in the step (1) is 1.1: 1; controlling the temperature of the heat preservation and standing in the step (2) to be 60-65 ℃, and controlling the time of the heat preservation and standing in the step (2) to be 3-6 h; adding ethylenediamine into the mixture obtained in the step (2), and stirring for 1-2 hours;
    (3) and (3) carrying out reduced pressure distillation on the upper layer reaction liquid obtained from the liquid separation in the step (2) to obtain N- [3- (trimethoxysilyl) propyl ] N-butylamine.
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CN102093404A (en) * 2010-10-29 2011-06-15 华南理工大学 Method for recovering and treating waste materials in aminosilane preparation
CN103333200A (en) * 2013-07-22 2013-10-02 荆州市江汉精细化工有限公司 N-butyl aminopropyl trialkoxy silane synthesizing method
CN104926852A (en) * 2014-03-19 2015-09-23 张家港市国泰华荣化工新材料有限公司 Preparation method of n-butylamine propyl trimethoxy silane

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Publication number Priority date Publication date Assignee Title
CN102093404A (en) * 2010-10-29 2011-06-15 华南理工大学 Method for recovering and treating waste materials in aminosilane preparation
CN103333200A (en) * 2013-07-22 2013-10-02 荆州市江汉精细化工有限公司 N-butyl aminopropyl trialkoxy silane synthesizing method
CN104926852A (en) * 2014-03-19 2015-09-23 张家港市国泰华荣化工新材料有限公司 Preparation method of n-butylamine propyl trimethoxy silane

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