CN112480161A - Aminopropyl trimethoxy silane and preparation method thereof - Google Patents
Aminopropyl trimethoxy silane and preparation method thereof Download PDFInfo
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- CN112480161A CN112480161A CN201910860612.0A CN201910860612A CN112480161A CN 112480161 A CN112480161 A CN 112480161A CN 201910860612 A CN201910860612 A CN 201910860612A CN 112480161 A CN112480161 A CN 112480161A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
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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
- 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 aminopropyl trimethoxysilane, which comprises the steps of taking allylamine and hexamethyldisilazane as raw materials, reacting to generate N-allyl-N, N-bis (trimethylsilyl) amine so as to protect amino; carrying out addition reaction on N-allyl-N, N-bis (trimethylsilyl) amine and trimethoxy silane to generate a silane intermediate; hydrolyzing the silane intermediate to prepare aminopropyl trimethoxy silane. The method has the advantages of high product yield, high purity, simple process, safety and environmental protection.
Description
Technical Field
The invention belongs to the field of fine chemical engineering, and particularly relates to aminopropyl trimethoxysilane and a preparation method thereof.
Background
The aminopropyl trimethoxy silane is a silane coupling agent product with wide application, has the functions of tackifying, cross-bonding, coupling and the like, can improve the strength, wear resistance, moisture resistance, ageing resistance and other properties of the product, is widely applied to the industrial fields of coatings, glass fibers, sealants, electronics, casting, rubber, plastics, paints, machinery, amino silicone oil, polyimide end-capping agents and the like, and has better market prospect.
Currently, there are three main methods for synthesizing aminopropyltrimethoxysilane:
(1) one-step addition method. The aminopropyl trimethoxy silane can be obtained by the addition reaction of trimethoxy silane and allylamine under the condition of a catalyst and then by distillation, and the product yield is about 85 percent. However, when the aminopropyltrimethoxysilane is synthesized by a one-step addition method, the allylamine activity is high, a beta addition byproduct is generated in the reaction process, the boiling point difference between the beta addition byproduct and the alpha addition product which is the main product is not obvious, the separation and purification difficulty is high, the selectivity of the catalyst is difficult to control, and no mature process can be used for industrial production at present.
(2) And (4) performing an ammonolysis method. The aminopropyl trimethoxy silane product can be obtained by reacting liquid ammonia with chloropropyl trimethoxy silane at high temperature and high pressure, and filtering and distilling, wherein the yield is about 75%. The ammonolysis method is the most main way for industrially producing aminopropyl trimethoxysilane at present, but the method needs to react under the condition of high pressure of 5-10MPa, has higher requirements on equipment and has high process risk. The ammonolysis method needs to be provided with an ammonia compression recovery system, the by-product ammonium chloride is difficult to treat, the corrosion to equipment is high, the production environment is poor, and the production efficiency is low.
(3) Hydrogenation reduction method. Cyanoethyl trimethoxy silane is subjected to reduction reaction with hydrogen under the pressure and the catalyst to obtain aminopropyl trimethoxy silane product, and the yield is about 95%. This method is commonly found in foreign patents and has the following main disadvantages: the cost of the required raw materials is very high, the synthesis of cyanoethyl trimethoxy silane has high technological requirements, and the hydrogenation reduction process has strict requirements on equipment and technology, so that the requirements of industrial production are difficult to meet.
Disclosure of Invention
The invention aims to solve the technical problem of providing aminopropyl trimethoxy silane and a preparation method thereof, aiming at the defects in the prior art, and the aminopropyl trimethoxy silane has the advantages of high product yield, high purity, simple process, safety and environmental protection.
According to one aspect of the present invention, the technical scheme adopted in the present invention for solving the above technical problems is as follows:
a process for preparing aminopropyl trimethoxy silane includes such steps as,
amino protection: taking allylamine (also called allylamine, CH)2＝CHCH2NH2) Hexamethyldisilazane ((CH)3)3SiNHSi(CH3)3) As raw material, reacting to generate N-allyl-N, N-bis (trimethylsilyl) amine (CH)2＝CHCH2N(Si(CH3)3)2) To protect the amino group;
preparing a silane intermediate: adding a trimethoxy silane as a raw material to the resulting N-allyl-N, N-bis (trimethylsilyl) amine to perform an addition reaction to give a silane intermediate ((CH)3O)3SiCH2CH2CH2N(Si(CH3)3)2)；
Hydrolysis: hydrolyzing the silane intermediate to prepare aminopropyl trimethoxy silane.
Preferably, the method specifically comprises the following steps,
s1, adding allylamine and hexamethyldisilazane as raw materials into a first reactor according to a certain molar ratio, adding a first catalyst, heating to a first temperature, and maintaining for a sufficient time to enable the raw materials to react to generate N-allyl-N, N-bis (trimethylsilyl) amine to form the para-amino protection;
wherein the structural formula of the N-allyl-N, N-bis (trimethylsilyl) amine is as follows:
in the formula: alpha, beta and alpha respectively represent alpha carbon, beta carbon and alpha carbon.
Compared with raw material allylamine or hexamethyldisilazane, the steric hindrance effect of the beta addition site of N-allyl-N, N-bis (trimethylsilyl) amine is increased, and the beta addition reaction activity can be inhibited, so that only alpha addition is carried out in the subsequent addition reaction to obtain a target intermediate product, and no beta addition, namely no side product is generated.
S2, adding the N-allyl-N, N-bis (trimethylsilyl) amine generated by the reaction into a second reactor, adding a second catalyst, heating to a second temperature to activate the second catalyst, adding the raw material trimethoxy silane, and continuously maintaining the second temperature to generate a silane intermediate through the reaction, thereby completing the preparation of the silane intermediate;
wherein the structural formula of the silane intermediate is as follows:
s3, adding the silane intermediate into a third reactor, heating to a third temperature, adding water, maintaining the third temperature, and hydrolyzing the silane intermediate to generate aminopropyl trimethoxysilane (NH in the molecular formula)2CH2CH2CH2Si(OCH3)3)；
S4, adding a dehydrating agent into the hydrolysate, filtering to remove filter residue, and distilling to obtain the product aminopropyl trimethoxysilane.
Preferably, in step S1,
the molar ratio of allylamine to hexamethyldisilazane is 1: 1.1 to 1.3;
the dosage of the first catalyst is 2-5 per mill of the weight of the allylamine;
the first temperature is 30-50 ℃, and the first temperature is maintained for 5-6 h.
Preferably, the first catalyst is p-toluenesulfonic acid.
Preferably, in the step S2,
the dosage of the second catalyst is 2-5 per mill of the weight of the N-allyl-N, N-bis (trimethylsilyl) amine;
the second temperature is 75-85 ℃, and the activation time of the second catalyst is 30-60 min;
the molar ratio of the trimethoxy silane to the N-allyl-N, N-bis (trimethylsilyl) amine is 1.01-1.05: 1;
and continuously maintaining the second temperature for 1-2 hours.
Preferably, the trimethoxy silane is added in a dropwise manner, and the dropwise adding speed of the trimethoxy silane is 5-10 ml/min.
Preferably, the second catalyst is a platinum-containing catalyst, and the preparation method of the platinum-containing catalyst comprises the following steps:
s201, taking chloroplatinic acid and tetrahydrofuran as raw materials, heating and refluxing for a period of time under the protection of nitrogen to obtain a mixture;
s202, distilling and concentrating the mixture, adding a dehydrating agent for dehydration and drying, and filtering to obtain a filtrate;
and S203, adding triphenylphosphine into the filtrate to react to generate a platinum-containing catalyst.
Preferably, in the step S3,
the third temperature is 50-60 ℃, and the time for maintaining the third temperature is 1-2 h;
the molar ratio of the silane intermediate to the water is 1:1.01 to 1.03.
Preferably, the water is deionized water, the water is added in a dropwise manner, and the dropwise adding speed of the water is 1-5 ml/min.
Preferably, in the step S4, the amount of the dehydrating agent is 10 to 15% by weight of the silane intermediate, and the dehydrating agent is anhydrous sodium sulfate.
In another aspect of the present invention, there is provided aminopropyltrimethoxysilane, which is prepared by the above-mentioned method.
The preparation method of aminopropyl trimethoxysilane provided by the invention adopts three steps of reaction, firstly protects amino, then performs addition reaction, and finally hydrolyzes to obtain the aminopropyl trimethoxysilane product, and has the advantages of simple process, high product yield (more than 90 percent) and high purity (99 percent), and the specific beneficial effects are as follows:
(1) the amino group is protected by first reacting allylamine with hexamethyldisilazane to synthesize N-allyl-N, N-bis (trimethylsilyl) amine. Compared with raw material allylamine or hexamethyldisilazane, the N-allyl-N, N-bis (trimethylsilyl) amine is generated, the steric hindrance effect of a beta addition site can be increased, and the activity of the beta addition reaction is inhibited, so that only alpha addition is carried out in the subsequent addition reaction to obtain a target intermediate product, and no beta addition is carried out, namely no by-product is generated, thereby improving the product yield and purity of aminopropyltrimethoxysilane.
(2) The three reactions can be carried out under the conditions of lower temperature and normal pressure, the ammonia gas released by the reaction can be absorbed by water, the process is simple, and the operation is safe.
(3) The highly toxic raw material allylamine is converted into non-toxic N-allyl-N, N-bis (trimethylsilyl) amine in the reaction process, so that the danger in the production process can be reduced.
(4) No by-product is generated, the process is safe and environment-friendly, and the dehydrating agent anhydrous sodium sulfate can be baked for 24 hours at the high temperature of 200 ℃ for regeneration after being used and can be reused. The raw material hexamethyldisilazane which does not participate in the reaction can be recovered from the effluent for reuse.
Detailed Description
In order to make the technical solutions of the present invention better understood, the present invention will be further clearly and completely described below with reference to specific embodiments of the present invention.
Example 1
This example discloses a method for preparing aminopropyltrimethoxysilane,
step 1: taking allylamine and hexamethyldisilazane as raw materials, reacting to generate N-allyl-N, N-bis (trimethylsilyl) amine to protect amino, absorbing ammonia gas generated by the reaction with water, and obtaining the reaction formula as follows:
CH2＝CHCH2NH2+(CH3)3SiNHSi(CH3)3→
CH2＝CHCH2N(Si(CH3)3)2+NH3↑
compared with raw material allylamine or hexamethyldisilazane, the N-allyl-N, N-bis (trimethylsilyl) amine can increase the steric hindrance effect of beta addition position and inhibit the activity of beta position addition reaction, so that only alpha position addition is carried out in subsequent addition reaction to obtain a target intermediate product, and no beta position addition, namely no side product is generated.
Step 2: the N-allyl-N, N-bis (trimethylsilyl) amine and trimethoxy silane are subjected to addition reaction to generate a silane intermediate (CH)3O)3SiCH2CH2CH2N(Si(CH3)3)2The reaction formula is as follows:
CH2CHCH2N(Si(CH3)3)2+HSi(OCH3)3→
(CH3O)3SiCH2CH2CH2N(Si(CH3)3)2
and step 3: hydrolyzing the silane intermediate to prepare aminopropyl trimethoxy silane, wherein the reaction formula is as follows:
(CH3O)3SiCH2CH2CH2N(Si(CH3)3)2+H2O→
NH2CH2CH2CH2Si(OCH3)3+(CH3)3SiOSi(CH3)3
wherein: the molar ratio of allylamine to hexamethyldisilazane is 1: 1.1 to 1.3; the molar ratio of the trimethoxy silane to the N-allyl-N, N-bis (trimethylsilyl) amine is 1.01 to 1.05: 1; the molar ratio of silane intermediate to water is 1:1.01 to 1.03.
The preparation method of aminopropyl trimethoxysilane adopts three steps of reaction, firstly protects amino, then performs addition reaction, and finally hydrolyzes to obtain the aminopropyl trimethoxysilane product, and has the advantages of simple process, high product yield and high purity.
The aminopropyl trimethoxysilane disclosed in this example was prepared by the above-described method.
Example 2
The embodiment discloses a preparation method of aminopropyltrimethoxysilane, which specifically comprises the following steps:
s1, the allylamine and hexamethyldisilazane are charged to a first reactor, a first catalyst is added, and the mixture is heated to a first temperature and for a time sufficient to react the raw materials to form N-allyl-N, N-bis (trimethylsilyl) amine.
Alternatively, the hexamethyldisilazane is kept in excess with respect to the allylamine to ensure that the allylamine is sufficiently reacted, the molar ratio of allylamine to hexamethyldisilazane preferably being 1: 1.1 to 1.3.
Optionally, the amount of the first catalyst is 2 to 5 per mill of the weight of the allylamine.
Optionally, the first temperature is 30 to 50 ℃ and the first temperature is maintained for a sufficient time of 5 to 6 hours to allow sufficient reaction to increase the yield of N-allyl-N, N-bis (trimethylsilyl) amine.
In this example, the molar ratio of allylamine to hexamethyldisilazane was 1:1.01, i.e. 57g of allylamine and 177.1g of hexamethyldisilazane; the first catalyst is p-toluenesulfonic acid, and the dosage of the first catalyst is preferably 2 per thousand of the weight of allyl amine, namely 0.114g of p-toluenesulfonic acid; the first temperature was 35 ℃ and the first temperature was maintained for 5 hours (i.e., the incubation time).
In this example, a four-neck flask equipped with a stirrer, a constant pressure dropping funnel, a reflux condenser and a thermometer is preferably used as the first reactor, but it is needless to say that other types of reactors capable of achieving the same function may be used, and the present example is not limited to this. Similarly, in the second reactor and the third reactor in the subsequent steps S2 and S3 of this embodiment, a four-neck flask equipped with a stirrer, a constant pressure dropping funnel, a reflux condenser and a thermometer is preferably used, or other types of reactors capable of achieving the same functions are used, and the details are not repeated here.
Specifically, 57g of allylamine and 177.1g of hexamethyldisilazane were added to a first reactor, 0.114g of p-toluenesulfonic acid was added as a catalyst, the mixture was stirred, and the first reactor was heated to 35 ℃ (i.e., a first temperature) and maintained for 5 hours, so that the allylamine and the hexamethyldisilazane were sufficiently reacted under the conditions of the catalyst and heating, and a mixture containing N-allyl-N, N-bis (trimethylsilyl) amine and hexamethyldisilazane was obtained.
Distilling the mixture under the vacuum degree of-0.098 MPa, collecting the distillate at 70-75 deg.C to obtain 24.15g (0.15 mol) hexamethyldisilazane, and recovering excessive hexamethyldisilazane which does not participate in the reaction for further use as raw material; the fractions were collected at 110 ℃ and 120 ℃ to obtain 190.95g (i.e., 0.95mol) of N-allyl-N, N-bis (trimethylsilyl) amine with a purity of 99.0% or more.
S2, adding N-allyl-N, N-bis (trimethylsilyl) amine into a second reactor, adding a second catalyst, heating to a second temperature to activate the second catalyst, adding trimethoxysilane, and continuously maintaining the second temperature to react to generate a silane intermediate.
Optionally, the amount of the second catalyst is 2-5 per mill of the weight of the N-allyl-N, N-bis (trimethylsilyl) amine; the second catalyst is a platinum-containing catalyst.
The platinum-containing catalyst in this embodiment is preferably prepared by the following steps, but may be prepared by other methods for achieving the same purpose, and is not limited to the following methods:
s201, taking chloroplatinic acid (also called hexachloroplatinic acid) and tetrahydrofuran as raw materials, adding the raw materials into a reactor which can be heated and refluxed, such as a flask provided with a condenser.
In the embodiment, the dosage of the chloroplatinic acid is preferably 5-10 g, the tetrahydrofuran is 500ml, and the chloroplatinic acid is added into the tetrahydrofuran and stirred to completely dissolve the chloroplatinic acid.
S202, heating under the protection of nitrogen, and refluxing for a period of time to fully perform a complexing reaction on the raw materials; then carrying out distillation concentration until proper residual materials are left, and stopping the distillation concentration; adding dehydrating agent, dehydrating, drying, and filtering to obtain filtrate.
In the embodiment, the heating temperature is higher than or equal to the boiling point (66 ℃) of tetrahydrofuran, and the reflux time is 3-5 hours, preferably 4 hours; preferably, concentration by distillation is stopped when 200ml of the residue is left. The dehydrating agent in the step S202 is preferably anhydrous sodium sulfate, and the dosage of the dehydrating agent is preferably 10-20 g.
And S203, adding triphenylphosphine into the filtrate to react to generate a platinum-containing catalyst.
In this embodiment, the amount of triphenylphosphine used is preferably 2 to 5 g.
Optionally, the second temperature is 75-85 ℃, and the activation time of the second catalyst is 30-60 min.
Optionally, the molar ratio of trimethoxy silane to N-allyl-N, N-bis (trimethylsilyl) amine is 1.01 to 1.05: 1.
optionally, the time for continuously maintaining the second temperature is 1-2 h.
In this example, the amount of the second catalyst used was 2% by weight of N-allyl-N, N-bis (trimethylsilyl) amine, i.e. 0.3818g of platinum-containing catalyst; the second temperature is 75 ℃, and the activation time of the second catalyst is 30 min; the molar ratio of trimethoxysilane to N-allyl-N, N-bis (trimethylsilyl) amine was 1.01: 1, i.e. the trimethoxysilane is 0.9595mol (117.095 g); the second temperature was maintained for 1 h.
Specifically, 190.95g of N-allyl-N, N-bis (trimethylsilyl) amine was added to the second reactor, 0.3818g of a platinum-containing catalyst was added, and stirring was carried out; heating to 75 deg.C for 30min to activate the platinum-containing catalyst to strengthen the catalystThe catalytic activity of (a); then 0.9595mol of trimethoxy silane is dripped into N-allyl-N, N-bis (trimethylsilyl) amine in a second reactor within 30min at the speed of 5-10 ml/min, so that the N-allyl-N, N-bis (trimethylsilyl) amine and the trimethoxy silane are subjected to addition reaction under the conditions of platinum catalyst and heating to generate a silane intermediate (CH)3O)3SiCH2CH2CH2N(Si(CH3)3)2B, carrying out the following steps of; after the addition of trimethoxysilane, the reaction was continued (i.e., aged) by maintaining the temperature at 75 ℃ for 1 hour. After the reaction was complete, the amount of silane intermediate weighed 306.85g (i.e., 0.95 mol).
S3, adding the silane intermediate into a third reactor, heating to a third temperature, adding water, and maintaining the third temperature to hydrolyze the silane intermediate to generate aminopropyl trimethoxysilane.
Optionally, the third temperature is 50-60 ℃; the third temperature is maintained for 1-2 h.
Optionally, the molar ratio of silane intermediate to water is 1:1.01 to 1.03.
In the embodiment, the third temperature is preferably 50 ℃, and the time for maintaining the third temperature is preferably 2 h; the molar ratio of silane intermediate to water is preferably 1:1.01, i.e. water is 0.9595mol (i.e. 17.721 g); the water is preferably deionized water to reduce or avoid other impurities from being brought in; the preferable dropping mode of the water is dropping, and the dropping speed of the water is 1-5 ml/min.
Specifically, 306.85g (0.95mol) of silane intermediate is added into a third reactor, heated to 50 ℃, 17.271g (0.9595 mol) of deionized water is added into the silane intermediate in a dropwise manner within 1 hour at a dropwise adding speed of 1-5 ml/min, and the silane intermediate is hydrolyzed to generate aminopropyltrimethoxysilane; after the deionized water is added dropwise, the temperature of 50 ℃ is continuously maintained for 2h to ensure complete reaction.
And S4, adding a dehydrating agent into the hydrolysate, filtering to remove filter residues, and distilling to obtain the product.
Optionally, the amount of dehydrating agent is 10-15% of the weight of the silane intermediate.
In this example, anhydrous sodium sulfate is preferably used as the dehydrating agent, and the amount of the dehydrating agent used is preferably 10% by weight of the silane intermediate, that is, 30.685g of anhydrous sodium sulfate.
Specifically, 30.685g of anhydrous sodium sulfate was added to the hydrolyzate in step S3 to subject the hydrolyzate to dehydration treatment; further, filtration was carried out to remove the residue, and the obtained filtrate, i.e., a crude aminopropyltrimethoxy product containing hexamethyldisiloxane (by-product), was weighed to 320.0 g. Hexamethyldisiloxane is a by-product that can be separated by collecting fractions at different temperatures due to its different boiling point from aminopropyltrimethoxysilane.
Then, distilling the filtrate under the condition that the vacuum degree is-0.098 MPa, and collecting fractions at 90-100 ℃ to obtain hexamethyldisiloxane (a byproduct) so as to remove impurities and improve the product purity; and collecting fractions at 130-140 ℃ to obtain the aminopropyltrimethoxysilane product.
By weighing, the aminopropyl trimethoxy silane accounts for 163.4g, the product mass yield is 91.3%, and the purity is 99.2%; 148.2g hexamethyldisiloxane, 99.0% purity. In the embodiment, the filter residue is the hydrous sodium sulfate after the anhydrous sodium sulfate absorbs water, and the hydrous sodium sulfate is baked and dehydrated for a period of time (24 hours) at high temperature (preferably equal to or more than 200 ℃) and then is regenerated into the anhydrous sodium sulfate which can be repeatedly used, so that the cost is reduced.
The aminopropyl trimethoxysilane disclosed in this example was prepared by the method described above.
Example 3
The embodiment discloses a preparation method of aminopropyltrimethoxysilane, which specifically comprises the following steps:
s1, the allylamine and hexamethyldisilazane are charged to a first reactor, a first catalyst is added, and the mixture is heated to a first temperature and for a time sufficient to react the raw materials to form N-allyl-N, N-bis (trimethylsilyl) amine.
In this example, the molar ratio of allylamine to hexamethyldisilazane was 1:1.02, i.e. 57g of allylamine and 193.2g of hexamethyldisilazane; the first catalyst is p-toluenesulfonic acid, preferably used in an amount of 3% by weight, i.e. 0.171g, based on the weight of allylamine; the first temperature was 40 ℃ and the first temperature was maintained for 5 h.
Specifically, 57g of allylamine and 193.2g of hexamethyldisilazane were charged into a four-necked flask (i.e., a first reactor) equipped with a stirrer, a constant pressure dropping funnel, a reflux condenser and a thermometer, 0.171g of p-toluenesulfonic acid was added as a catalyst, the mixture was stirred, the first reactor was heated to 40 ℃ and maintained for 5 hours, and the allylamine and the hexamethyldisilazane were sufficiently reacted with each other in the presence of the catalyst under heating to obtain a mixture containing N-allyl-N, N-bis (trimethylsilyl) amine and hexamethyldisilazane.
Distilling the mixture under the vacuum degree of-0.098 MPa, collecting fractions at 70-75 deg.C to obtain 35.42g (0.22 mol) hexamethyldisilazane, which can be recovered and used as raw material; then the fractions were collected at 110 ℃ and 120 ℃ to obtain 196.98g (i.e., 0.98mol) of N-allyl-N, N-bis (trimethylsilyl) amine having a purity of 99.0% or more.
S2, adding N-allyl-N, N-bis (trimethylsilyl) amine into a second reactor, adding a second catalyst, heating to a second temperature to activate the second catalyst, adding trimethoxysilane, and continuously maintaining the second temperature to react to generate a silane intermediate.
In this example, the second catalyst was a platinum-containing catalyst, and the platinum-containing catalyst obtained in example 2 using chloroplatinic acid and tetrahydrofuran as raw materials was used. In an amount of 3 ‰ (i.e., 0.5909g) based on the weight of N-allyl-N, N-bis (trimethylsilyl) amine; the second temperature is 75 ℃, and the activation time of the second catalyst is 30 min; the molar ratio of trimethoxysilane to N-allyl-N, N-bis (trimethylsilyl) amine was 1.03: 1, namely the trimethoxy silane is used in an amount of 1.0094mol (namely 123.146 g); the second temperature was maintained for 1 h.
Specifically, 196.98g (i.e., 0.98mol) of N-allyl-N, N-bis (trimethylsilyl) amine was added to the second reactor, and 0.5909g of a platinum-containing catalyst was added and stirred; heating to 75 deg.C, maintaining for 30min to activate platinum-containing catalyst,to enhance the catalytic activity of the catalyst; dropwise adding 1.0094mol (123.146 g) of trimethoxy silane into N-allyl-N, N-bis (trimethylsilyl) amine in a second reactor at a speed of 5-10 ml/min within 30min to perform addition reaction on the N-allyl-N, N-bis (trimethylsilyl) amine and the trimethoxy silane under the conditions of platinum catalyst and heating to generate a silane intermediate (CH)3O)3SiCH2CH2CH2N(Si(CH3)3)2(ii) a After the addition of trimethoxysilane, the reaction was continued (i.e., aged) by maintaining the temperature at 75 ℃ for 1 hour. After the reaction was complete, the amount of silane intermediate weighed 316.54g (i.e., 0.98 mol).
S3, adding the silane intermediate into a third reactor, heating to a third temperature, adding water, and maintaining the third temperature to hydrolyze the silane intermediate to generate aminopropyl trimethoxysilane.
In the embodiment, the third temperature is preferably 50 ℃, and the time for maintaining the third temperature is preferably 2 h; the molar ratio of silane intermediate to water is preferably 1:1.02, i.e., water is 0.9898mol (i.e., 17.816 g); the water is preferably deionized water to reduce or avoid other impurities from being brought in; the preferable dropping mode of the water is dropping, and the dropping speed of the water is 1-5 ml/min.
Specifically, 316.54(0.98mol) silane intermediate is added into a third reactor, heated to 50 ℃, 17.816g (0.9898 mol) deionized water is added into the silane intermediate in a dropwise manner within 1h at a dropwise adding speed of 1-5 ml/min, and the silane intermediate is hydrolyzed to generate aminopropyltrimethoxysilane; after the deionized water is added dropwise, the temperature of 50 ℃ is continuously maintained for 1h to ensure complete reaction.
And S4, adding a dehydrating agent into the hydrolysate, filtering to remove filter residues, and distilling to obtain the product.
In this example, anhydrous sodium sulfate is preferably used as the dehydrating agent, and the amount of the dehydrating agent used is 10% by weight based on the weight of the silane intermediate, that is, 31.654g of anhydrous sodium sulfate.
Specifically, 31.654g of anhydrous sodium sulfate was added to the hydrolyzate in step S3 to subject the hydrolyzate to dehydration treatment; then filtering is carried out, filter residue is removed, and the obtained filtrate, namely aminopropyl trimethoxy crude product, is weighed to be 330.0 g;
then, distilling the filtrate under the condition that the vacuum degree is-0.098 MPa, and collecting fractions at 90-100 ℃ to obtain hexamethyldisiloxane (a byproduct) so as to remove impurities and improve the product purity; and collecting fractions at 130-140 ℃ to obtain the aminopropyltrimethoxysilane product.
Weighing, wherein the aminopropyl trimethoxysilane is 166.6g, the mass yield of the product is 93 percent, and the purity is 99.5 percent; 155.6g of hexamethyldisiloxane, purity 99.3%.
Example 4
The embodiment discloses a preparation method of aminopropyltrimethoxysilane, which specifically comprises the following steps:
s1, the allylamine and hexamethyldisilazane are charged to a first reactor, a first catalyst is added, and the mixture is heated to a first temperature and for a time sufficient to react the raw materials to form N-allyl-N, N-bis (trimethylsilyl) amine.
In this example, the molar ratio of allylamine to hexamethyldisilazane was 1:1.03 g of allylamine and 209.30g of hexamethyldisilazane (preferably comprising 24.15g and 35.42g of hexamethyldisilazane recovered in examples 1 and 2, respectively, and 149.73g of originally charged hexamethyldisilazane); the first catalyst, p-toluenesulfonic acid, is preferably used in an amount of 5% by weight, i.e. 0.285g, based on the weight of allylamine; the first temperature was 45 ℃ and the first temperature was maintained for 5 hours (i.e., the incubation time).
Specifically, 57g of allylamine and 209.30g of hexamethyldisilazane were added to a first reactor, 0.285g of p-toluenesulfonic acid was added as a catalyst, the mixture was stirred, and the first reactor was heated to 45 ℃ for 5 hours, so that the allylamine and hexamethyldisilazane were sufficiently reacted under the conditions of catalyst and heating to obtain a mixture containing N-allyl-N, N-bis (trimethylsilyl) amine and hexamethyldisilazane.
Distilling the mixture under the vacuum degree of-0.098 MPa, collecting fractions at 70-75 deg.C to obtain 54.74g (0.34 mol) hexamethyldisilazane, which can be recovered and used as raw material; the fractions were collected at 110 ℃ and 120 ℃ to obtain 192.96g (i.e., 0.96mol) of N-allyl-N, N-bis (trimethylsilyl) amine with a purity of 99.0% or more.
S2, adding N-allyl-N, N-bis (trimethylsilyl) amine into a second reactor, adding a second catalyst, heating to a second temperature to activate the second catalyst, adding trimethoxysilane, and continuously maintaining the second temperature to react to generate a silane intermediate.
In this example, the second catalyst was a platinum-containing catalyst, and the platinum-containing catalyst obtained in example 2 using chloroplatinic acid and tetrahydrofuran as raw materials was used. The dosage of the N-allyl-N, N-bis (trimethylsilyl) amine is 5 per mill (0.9648 g) of the weight of the N-allyl-N, N-bis (trimethylsilyl) amine; the second temperature is 80 ℃, and the activation time of the second catalyst is 30 min; the molar ratio of trimethoxysilane to N-allyl-N, N-bis (trimethylsilyl) amine was 1.05: 1, i.e. the amount of trimethoxysilane used is 1.008mol (122.794 g); the second temperature was maintained for 2 h.
Specifically, 192.96g (0.96mol) of N-allyl-N, N-bis (trimethylsilyl) amine was added to the second reactor, 0.9648g of a platinum-containing catalyst was added thereto, and stirring was carried out; heating to 80 deg.C, maintaining for 30min, and activating platinum-containing catalyst to enhance catalytic activity of the catalyst; 122.794g (1.008mol) of trimethoxy silane is dripped into N-allyl-N, N-bis (trimethylsilyl) amine in a second reactor at the speed of 5-10 ml/min, so that the N-allyl-N, N-bis (trimethylsilyl) amine and the trimethoxy silane are subjected to addition reaction under the conditions of platinum catalyst and heating to generate a silane intermediate (CH)3O)3SiCH2CH2CH2N(Si(CH3)3)2(ii) a After the addition of trimethoxysilane, the reaction was continued (i.e., aged) by maintaining the temperature at 80 ℃ for 2 hours. After the reaction was complete, the amount of silane intermediate weighed 310.08g (i.e., 0.96 mol).
S3, adding the silane intermediate into a third reactor, heating to a third temperature, adding water, and maintaining the third temperature to hydrolyze the silane intermediate to generate aminopropyl trimethoxysilane.
In the embodiment, the third temperature is preferably 60 ℃, and the time for maintaining the third temperature is preferably 2 h; the molar ratio of silane intermediate to water is preferably 1:1.03, i.e., water is 0.9696mol (i.e., 17.452 g); the water is preferably deionized water to reduce or avoid other impurities from being brought in; the preferable dropping mode of the water is dropping, and the dropping speed of the water is 1-5 ml/min.
Specifically, 310.08(0.96mol) silane intermediate is added into a third reactor, heated to 60 ℃, 17.452g (0.9696 mol) deionized water is added into the silane intermediate in a dropwise manner within 1h at a dropwise adding speed of 1-5 ml/min, and the silane intermediate is hydrolyzed to generate aminopropyltrimethoxysilane; after the deionized water is added dropwise, the temperature of 60 ℃ is continuously maintained for 2h to ensure complete reaction.
And S4, adding a dehydrating agent into the hydrolysate, filtering to remove filter residues, and distilling to obtain the product.
In this example, anhydrous sodium sulfate is preferably used as the dehydrating agent, and the amount of the dehydrating agent used is 15% by weight of the silane intermediate, that is, 46.512g of anhydrous sodium sulfate.
Specifically, 46.512g of anhydrous sodium sulfate was added to the hydrolyzate in step S3 to subject the hydrolyzate to dehydration treatment; then filtering is carried out, filter residue is removed, and obtained filtrate, namely aminopropyl trimethoxy crude product, is weighed to be 318.0 g;
then, distilling the filtrate under the condition that the vacuum degree is-0.098 MPa, and collecting fractions at 90-100 ℃ to obtain hexamethyldisiloxane (a byproduct) so as to remove impurities and improve the product purity; and collecting fractions at 130-140 ℃ to obtain the aminopropyltrimethoxysilane product.
According to the weight, the aminopropyl trimethoxy silane accounts for 165.6g, the mass yield of the product is 92.5 percent, and the purity is 99.2 percent; 144.8g of hexamethyldisiloxane, 99.5% purity.
Example 5
The embodiment discloses a preparation method of aminopropyltrimethoxysilane, which specifically comprises the following steps:
s1, the allylamine and hexamethyldisilazane are charged to a first reactor, a first catalyst is added, and the mixture is heated to a first temperature and for a time sufficient to react the raw materials to form N-allyl-N, N-bis (trimethylsilyl) amine.
In this example, the molar ratio of allylamine to hexamethyldisilazane was 1:1.02, i.e. 57g of allylamine and 193.2g of hexamethyldisilazane; the first catalyst is p-toluenesulfonic acid, preferably used in an amount of 3% by weight, i.e. 0.171g, based on the weight of allylamine; the first temperature was 50 ℃ and the first temperature was maintained for 6 h.
Specifically, 57g of allylamine and 193.2g of hexamethyldisilazane were charged into a four-necked flask (i.e., a first reactor) equipped with a stirrer, a constant pressure dropping funnel, a reflux condenser and a thermometer, 0.171g of p-toluenesulfonic acid was added as a catalyst, the mixture was stirred, the first reactor was heated to 50 ℃ and maintained for 6 hours, and the allylamine and the hexamethyldisilazane were sufficiently reacted under catalyst and heating conditions to obtain a mixture containing N-allyl-N, N-bis (trimethylsilyl) amine and hexamethyldisilazane.
Distilling the mixture under the vacuum degree of-0.098 MPa, and collecting the distillate at 70-75 deg.C to obtain 37.03g (0.23 mol) hexamethyldisilazane which can be recovered and used as raw material; the fractions were collected at 110 ℃ and 120 ℃ to obtain 194.97g (i.e., 0.97mol) of N-allyl-N, N-bis (trimethylsilyl) amine with a purity of 99.0% or more.
S2, adding N-allyl-N, N-bis (trimethylsilyl) amine into a second reactor, adding a second catalyst, heating to a second temperature to activate the second catalyst, adding trimethoxysilane, and continuously maintaining the second temperature to react to generate a silane intermediate.
In this example, the second catalyst was a platinum-containing catalyst, and the platinum-containing catalyst obtained in example 2 using chloroplatinic acid and tetrahydrofuran as raw materials was used. In an amount of 3 ‰ (i.e., 0.5849g) based on the weight of N-allyl-N, N-bis (trimethylsilyl) amine; the second temperature is 75 ℃, and the activation time of the second catalyst is 45 min; the molar ratio of trimethoxysilane to N-allyl-N, N-bis (trimethylsilyl) amine was 1.03: 1, namely the trimethoxy silane is used in an amount of 0.9991mol (namely 121.89 g); the second temperature was maintained for 2 h.
Specifically, 194.97g (0.97mol) of N-allyl-N, N-bis (trimethylsilyl) amine was added to the second reactor, 0.5849g of a platinum-containing catalyst was added thereto, and stirring was carried out; heating to 75 deg.C, maintaining for 45min, and activating platinum-containing catalyst to enhance catalytic activity of the catalyst; adding 0.9991mol (121.89g) of trimethoxy silane dropwise into N-allyl-N, N-bis (trimethylsilyl) amine in a second reactor at a speed of 5-10 ml/min, and carrying out addition reaction on the N-allyl-N, N-bis (trimethylsilyl) amine and the trimethoxy silane under the conditions of platinum catalyst and heating to generate a silane intermediate (CH)3O)3SiCH2CH2CH2N(Si(CH3)3)2(ii) a After the trimethoxysilane addition was complete, the reaction was continued (i.e., aged) by maintaining the temperature at 75 ℃ for 2 h. After the reaction was complete, the amount of silane intermediate weighed 313.31g (i.e., 0.97 mol).
S3, adding the silane intermediate into a third reactor, heating to a third temperature, adding water, and maintaining the third temperature to hydrolyze the silane intermediate to generate aminopropyl trimethoxysilane.
In the embodiment, the third temperature is preferably 50 ℃, and the time for maintaining the third temperature is preferably 2 h; the molar ratio of silane intermediate to water is preferably 1:1.01, i.e. water is 0.9797mol (i.e. 17.6346 g); the water is preferably deionized water to reduce or avoid other impurities from being brought in; the preferable dropping mode of the water is dropping, and the dropping speed of the water is 1-5 ml/min.
Specifically, 313.31(0.97mol) silane intermediate is added into a third reactor, heated to 50 ℃, 17.6346g (0.9797 mol) deionized water is added into the silane intermediate in a dropwise manner within 1h at a dropwise adding speed of 1-5 ml/min, and the silane intermediate is hydrolyzed to generate aminopropyltrimethoxysilane; after the deionized water is added dropwise, the temperature of 50 ℃ is continuously maintained for 2h to ensure complete reaction.
And S4, adding a dehydrating agent into the hydrolysate, filtering to remove filter residues, and distilling to obtain the product.
In this example, anhydrous sodium sulfate is preferably used as the dehydrating agent, and the amount of the dehydrating agent used is 15% by weight of the silane intermediate, that is, 31.654g of anhydrous sodium sulfate.
Specifically, 31.654g of anhydrous sodium sulfate was added to the hydrolyzate in step S3 to subject the hydrolyzate to dehydration treatment; then filtering is carried out, filter residue is removed, and obtained filtrate, namely aminopropyl trimethoxy crude product, is weighed to be 318.0 g;
then, distilling the filtrate under the condition that the vacuum degree is-0.098 MPa, and collecting fractions at 90-100 ℃ to obtain hexamethyldisiloxane (a byproduct) so as to remove impurities and improve the product purity; and collecting fractions at 130-140 ℃ to obtain the aminopropyltrimethoxysilane product.
Weighing, wherein the mass yield of the aminopropyl trimethoxysilane is 168.0g, and the product has the mass yield of 93.8 percent and the purity of 99.4 percent; 155.8g of hexamethyldisiloxane, purity 99.4%.
Example 6
The embodiment discloses a preparation method of aminopropyltrimethoxysilane, which specifically comprises the following steps:
s1, the allylamine and hexamethyldisilazane are charged to a first reactor, a first catalyst is added, and the mixture is heated to a first temperature and for a time sufficient to react the raw materials to form N-allyl-N, N-bis (trimethylsilyl) amine.
In this example, the molar ratio of allylamine to hexamethyldisilazane was 1:1.02, i.e. 57g of allylamine and 193.2g of hexamethyldisilazane; the first catalyst is p-toluenesulfonic acid, preferably used in an amount of 3% by weight, i.e. 0.171g, based on the weight of allylamine; the first temperature is 30-50 ℃, and the first temperature is maintained for 5 hours.
Specifically, 57g of allylamine and 193.2g of hexamethyldisilazane are added into a four-neck flask (i.e., a first reactor) provided with a stirrer, a constant-pressure dropping funnel, a reflux condenser and a thermometer, 0.171g of p-toluenesulfonic acid is added as a catalyst, the mixture is stirred, the first reactor is heated to 30-50 ℃ and maintained for 5 hours, and the allylamine and the hexamethyldisilazane are fully reacted under the conditions of the catalyst and heating to obtain a mixture containing N-allyl-N, N-bis (trimethylsilyl) amine and the hexamethyldisilazane.
Distilling the mixture under the vacuum degree of-0.098 MPa, collecting fractions at 70-75 deg.C to obtain 35.42g (0.22 mol) hexamethyldisilazane, which can be recovered and used as raw material; then the fractions were collected at 110 ℃ and 120 ℃ to obtain 196.98g (i.e., 0.98mol) of N-allyl-N, N-bis (trimethylsilyl) amine having a purity of 99.0% or more.
S2, adding N-allyl-N, N-bis (trimethylsilyl) amine into a second reactor, adding a second catalyst, heating to a second temperature to activate the second catalyst, adding trimethoxysilane, and continuously maintaining the second temperature to react to generate a silane intermediate.
In this example, the second catalyst was a platinum-containing catalyst, and the platinum-containing catalyst obtained in example 2 using chloroplatinic acid and tetrahydrofuran as raw materials was used. In an amount of 3 ‰ (i.e., 0.5909g) based on the weight of N-allyl-N, N-bis (trimethylsilyl) amine; the second temperature is 85 ℃, and the activation time of the second catalyst is 60 min; the molar ratio of trimethoxysilane to N-allyl-N, N-bis (trimethylsilyl) amine was 1.04: 1, namely the trimethoxy silane is used in an amount of 1.0192mol (namely 124.342 g); the second temperature was maintained for 1 h.
Specifically, 196.98g (0.98mol) of N-allyl-N, N-bis (trimethylsilyl) amine was charged into the second reactor, and 0.5909g of a platinum-containing catalyst was added and stirred; heating to 85 deg.C, maintaining for 60min, and activating platinum-containing catalyst to enhance catalytic activity of the catalyst; 124.342g (1.0192mol) of trimethoxy silane is dropwise added into N-allyl-N, N-bis (trimethylsilyl) amine in a second reactor within 60min at the speed of 5-10 ml/min, so that the N-allyl-N, N-bis (trimethylsilyl) amine and the trimethoxy silane are subjected to addition reaction under the conditions of platinum catalyst and heating to generate a silane intermediate (CH)3O)3SiCH2CH2CH2N(Si(CH3)3)2(ii) a After the trimethoxysilane addition was complete, the reaction was continued (i.e., aged) by maintaining the temperature at 85 ℃ for 1 hour. After the reaction was complete, the amount of silane intermediate weighed 316.54g (i.e., 0.98 mol).
S3, adding the silane intermediate into a third reactor, heating to a third temperature, adding water, and maintaining the third temperature to hydrolyze the silane intermediate to generate aminopropyl trimethoxysilane.
In the embodiment, the third temperature is preferably 50 ℃, and the time for maintaining the third temperature is preferably 2 h; the molar ratio of silane intermediate to water is preferably 1:1.01, i.e. water is 0.9898mol (i.e. 17.816 g); the water is preferably deionized water to reduce or avoid other impurities from being brought in; the preferable dropping mode of the water is dropping, and the dropping speed of the water is 1-5 ml/min.
Specifically, 316.54g (namely 0.98mol) of silane intermediate is added into a third reactor, the third reactor is heated to 50 ℃, 17.819g (namely 0.9898mol) of deionized water is added into the silane intermediate in a dropwise manner within 1h at a dropwise adding speed of 1-5 ml/min, and the silane intermediate is hydrolyzed to generate aminopropyltrimethoxysilane; after the deionized water is added dropwise, the temperature of 50 ℃ is continuously maintained for 2h to ensure complete reaction.
And S4, adding a dehydrating agent into the hydrolysate, filtering to remove filter residues, and distilling to obtain the product.
In this example, anhydrous sodium sulfate is preferably used as the dehydrating agent, and the amount of the dehydrating agent used is 15% by weight of the silane intermediate, that is, 47.481.
Specifically, 47.481g of anhydrous sodium sulfate was added to the hydrolyzate in step S3 to subject the hydrolyzate to dehydration treatment; then filtering is carried out, filter residue is removed, and the obtained filtrate, namely aminopropyl trimethoxy crude product, is weighed to be 325.0 g;
then, distilling the filtrate under the condition that the vacuum degree is-0.098 MPa, and collecting fractions at 90-100 ℃ to obtain hexamethyldisiloxane (a byproduct) so as to remove impurities and improve the product purity; and collecting fractions at 130-140 ℃ to obtain the aminopropyltrimethoxysilane product.
According to the weight, the aminopropyl trimethoxy silane accounts for 162.5g, the mass yield of the product is 90.7 percent, and the purity is 99.3 percent; 152.8g of hexamethyldisiloxane, 99.5% purity.
It will be understood that the foregoing is only a preferred embodiment of the invention, and that the invention is not limited thereto. It will be apparent to those skilled in the art that various changes and modifications may be made without departing from the spirit and scope of the invention, and these changes and modifications are to be considered as within the scope of the invention.
Claims (11)
1. A process for preparing aminopropyl trimethoxy silane includes such steps as,
amino protection: taking allylamine and hexamethyldisilazane as raw materials, and reacting to generate N-allyl-N, N-bis (trimethylsilyl) amine;
preparing a silane intermediate: adding a raw material trimethoxy silane into the generated N-allyl-N, N-bis (trimethylsilyl) amine to perform addition reaction to generate a silane intermediate;
hydrolysis: hydrolyzing the silane intermediate to prepare aminopropyl trimethoxy silane.
2. The method of claim 1, comprising the steps of,
s1, adding allylamine and hexamethyldisilazane as raw materials into a first reactor according to a certain molar ratio, adding a first catalyst, heating to a first temperature, and maintaining for a sufficient time to enable the raw materials to react to generate N-allyl-N, N-bis (trimethylsilyl) amine to form the amino protection;
s2, adding the generated N-allyl-N, N-bis (trimethylsilyl) amine into a second reactor, adding a second catalyst, heating to a second temperature to activate the second catalyst, adding the raw material trimethoxy silane, and continuously maintaining the second temperature to react to generate a silane intermediate to finish the preparation of the silane intermediate;
s3, adding the silane intermediate into a third reactor, heating to a third temperature, adding water, and maintaining the third temperature to hydrolyze the silane intermediate to generate aminopropyltrimethoxysilane;
s4, adding a dehydrating agent into the hydrolysate, filtering to remove filter residue, and distilling to obtain the product aminopropyl trimethoxysilane.
3. The method of claim 2, wherein in step S1,
the molar ratio of allylamine to hexamethyldisilazane is 1: 1.1 to 1.3;
the dosage of the first catalyst is 2-5 per mill of the weight of the allylamine;
the first temperature is 30-50 ℃, and the first temperature is maintained for 5-6 h.
4. A process according to claim 3, wherein the first catalyst is p-toluenesulfonic acid.
5. The method of claim 2, wherein in step S2,
the dosage of the second catalyst is 2-5 per mill of the weight of the N-allyl-N, N-bis (trimethylsilyl) amine;
the second temperature is 75-85 ℃, and the activation time of the second catalyst is 30-60 min;
the molar ratio of the trimethoxy silane to the N-allyl-N, N-bis (trimethylsilyl) amine is 1.01-1.05: 1;
and continuously maintaining the second temperature for 1-2 hours.
6. The method for preparing aminopropyl trimethoxysilane according to claim 5, wherein the trimethoxysilane is added dropwise at a rate of 5-10 ml/min.
7. The method of claim 5, wherein the second catalyst is a platinum-containing catalyst, and the method comprises the steps of:
s201, taking chloroplatinic acid and tetrahydrofuran as raw materials, heating and refluxing for a period of time under the protection of nitrogen to obtain a mixture;
s202, distilling and concentrating the mixture, adding a dehydrating agent for dehydration and drying, and filtering to obtain a filtrate;
and S203, adding triphenylphosphine into the filtrate to react to generate a platinum-containing catalyst.
8. The method of claim 2, wherein in step S3,
the third temperature is 50-60 ℃, and the time for maintaining the third temperature is 1-2 h;
the molar ratio of the silane intermediate to the water is 1:1.01 to 1.03.
9. The method for preparing aminopropyltrimethoxysilane according to claim 8, wherein the water is deionized water, the water is added dropwise at a speed of 1-5 ml/min.
10. The method of claim 2, wherein in step S4, the amount of the dehydrating agent is 10-15% by weight of the silane intermediate, and the dehydrating agent is anhydrous sodium sulfate.
11. Aminopropyltrimethoxysilane, characterized in that it is obtainable by a process according to any of claims 1 to 10.
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Application publication date: 20210312 Assignee: Xinte silicon based new materials Co.,Ltd. Assignor: XINTE ENERGY Co.,Ltd. Contract record no.: X2023990000586 Denomination of invention: Ammoniopropyl Trimethoxysilane and its preparation method Granted publication date: 20230228 License type: Common License Record date: 20230605 |