CN105669739B - A kind of synthetic method of aminopropyl triethoxysilane - Google Patents
A kind of synthetic method of aminopropyl triethoxysilane Download PDFInfo
- Publication number
- CN105669739B CN105669739B CN201610142413.2A CN201610142413A CN105669739B CN 105669739 B CN105669739 B CN 105669739B CN 201610142413 A CN201610142413 A CN 201610142413A CN 105669739 B CN105669739 B CN 105669739B
- Authority
- CN
- China
- Prior art keywords
- aminopropyl triethoxysilane
- acetone
- hours
- triethoxysilane
- magnesium sulfate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000010189 synthetic method Methods 0.000 title claims abstract description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 54
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000009835 boiling Methods 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 239000002994 raw material Substances 0.000 claims abstract description 13
- 229910001868 water Inorganic materials 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 239000008367 deionised water Substances 0.000 claims abstract description 9
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 9
- 238000001914 filtration Methods 0.000 claims abstract description 9
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 6
- 239000006096 absorbing agent Substances 0.000 claims abstract description 5
- 230000008929 regeneration Effects 0.000 claims abstract description 5
- 238000011069 regeneration method Methods 0.000 claims abstract description 5
- BCDGQXUMWHRQCB-UHFFFAOYSA-N glycine methyl ketone Natural products CC(=O)CN BCDGQXUMWHRQCB-UHFFFAOYSA-N 0.000 claims abstract description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 46
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 20
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 19
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 18
- 229910000077 silane Inorganic materials 0.000 claims description 18
- 239000002262 Schiff base Substances 0.000 claims description 17
- 150000004753 Schiff bases Chemical class 0.000 claims description 16
- 230000032683 aging Effects 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 8
- 238000010792 warming Methods 0.000 claims description 7
- 238000009413 insulation Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 238000013019 agitation Methods 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 29
- 239000000706 filtrate Substances 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000007259 addition reaction Methods 0.000 abstract description 2
- 239000006227 byproduct Substances 0.000 abstract description 2
- 238000005265 energy consumption Methods 0.000 abstract 1
- 238000003912 environmental pollution Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 9
- 239000013078 crystal Substances 0.000 description 7
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000003760 magnetic stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- GBQYMXVQHATSCC-UHFFFAOYSA-N 3-triethoxysilylpropanenitrile Chemical compound CCO[Si](OCC)(OCC)CCC#N GBQYMXVQHATSCC-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000005915 ammonolysis reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 229910052564 epsomite Inorganic materials 0.000 description 2
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 2
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- ZGBSOTLWHZQNLH-UHFFFAOYSA-N [Mg].S(O)(O)(=O)=O Chemical compound [Mg].S(O)(O)(=O)=O ZGBSOTLWHZQNLH-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- -1 machinery Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
Classifications
-
- 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 Table
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The present invention relates to a kind of synthetic methods of aminopropyl triethoxysilane, belong to technical field of fine.The present invention is that first acetone and allyl amine are put in proportion into reactor, add in water absorbing agent, by reactant distillating filtering after stirring temperature reaction, it is reused after filter residue regeneration, filtrate carries out addition reaction with triethoxysilane with Karst catalyst, product after distilation reacts again with deionized water, and aminopropyl triethoxysilane product is obtained after distilling out low boiling point acetone.The aminopropyl triethoxysilane product yield of the present invention is high, and low energy consumption, and production cost is low, and by-product and raw material can be recycled, non-environmental-pollution.
Description
Technical field
The present invention relates to a kind of synthetic methods of aminopropyl triethoxysilane, belong to technical field of fine.
Background technology
Aminopropyl triethoxysilane is a kind of very extensive silane coupling agent product of purposes, be mainly used for coating,
The industrial circles such as rubber, plastics, paint, machinery, glass, electronics, casting, be currently on the market most widely used silane it
One, it plays thickening, hand over the effects that viscous, coupling, and the application performances such as wear-resisting, ageing-resistant of product can be increased.The product developing history
It is long, domestic and international Jun You big companies production, such as the KH-550 of the Chinese Academy of Sciences, the Z-6011 of Dow corning, Germany Di Gaosha
AMEO, the KBM-903 of Japanese SHIN-ETSU HANTOTAI, the U.S. step A-1100 of figure and the GF-93 of Germany watt gram etc., also have both at home and abroad much about
The patent and report of aminopropyl triethoxysilane synthesis, according to available data, the synthetic method of aminopropyl triethoxysilane
It is broadly divided into three kinds：
The first：Addition process.With triethoxysilane and allyl amine addition reaction under catalyst, ammonia is obtained after distillation
Propyl-triethoxysilicane product, product yield about 85%.
Second：Ammonolysis process.It is reacted at high temperature under high pressure with liquefied ammonia with chloropropyl triethoxysilane, filters, distill
To aminopropyl triethoxysilane product, product yield about 70%.
The third：Hydrogenating reduction method.With cyanoethyl triethoxysilane, in pressurization, similarly hereinafter hydrogen is restored with catalyst
Reaction, obtains aminopropyl triethoxysilane product, product yield about 95%.
The shortcomings that addition process synthesis aminopropyl triethoxysilane is the production that addition is caused to go out because allyl amine activity is higher
Object is the isomer product of a certain proportion of γ and β, it is difficult to detach and purify, product yield is very low, so now
Do not have to the method substantially industrially to produce.Ammonolysis process is the main way of industrial production aminopropyl triethoxysilane at present
Diameter, the disadvantages of this method are very high to equipment requirement, need a whole set of reaction under high pressure and recovery system, in addition can also be generated
By-product.There are two the shortcomings that hydrogenating reduction method：First, the synthesis of raw material cyanoethyl triethoxysilane is very high to technological requirement,
Production cost is very high；Second is that hydrogenating reduction process has equipment and technique certain requirement.
Invention content
It is an object of the invention to：It is easy to provide a kind of technological operation, raw material is easy to get, and can effectively ensure that product quality and receipts
The synthetic method of the aminopropyl triethoxysilane of rate.
The technical scheme is that：
A kind of synthetic method of aminopropyl triethoxysilane；It is characterized in that：It includes the following steps：
1）, by acetone and allyl amine in molar ratio 1.1~1.5：1 rate of charge is put into reaction vessel；By being thrown
The 45% of allyl amine weight adds in water absorbing agent；After the completion of feeding intake, it is warming up to 50 under 120~150 revs/min of mixing speed~
55 DEG C, then insulation reaction is warming up to 60~70 DEG C and distills out the complete raw material acetone of unreacted again after 5~6 hours；
2）, acetone distillation after be cooled to less than 30 DEG C filterings, obtain schiff bases ketimide；Filter residue is aqueous sulfuric acid
Magnesium, magnesium sulfate are reused after can heating regeneration；The complete raw material acetone of unreacted can be recycled；
3）, the schiff bases ketimide being obtained by filtration put into the reactor with magnetic agitation, at 60~90 revs/min
70~75 DEG C are warming up under mixing speed, adds in Karst catalyst, then triethoxysilane was added dropwise in 4 hours, three ethoxies
Base silane is 1 with schiff bases ketimide molar ratio：1.01~1.05, triethoxysilane be added dropwise after at 75~80 DEG C
Lower aging is distilled after 1~2 hour under the conditions of -0.098MPa, obtains silane intermediate；
4）, silane intermediate put into the reactor with magnetic agitation, risen under 60~90 revs/min of mixing speed
Temperature is to 60~70 DEG C, then deionized water was added dropwise in 2 hours, and the molar ratio of silane intermediate and deionized water is 1.01：
1, aging is distilled 2 hours under -0.098MPa again after 1~2 hour at 70~80 DEG C after being added dropwise, and steams low-boiling point material
Acetone；Then reactor is cooled down, obtains aminopropyl triethoxysilane finished product；The low-boiling point material acetone distilled out, which is recycled, to be made
With.
The aqueous magnesium sulfate that the water absorbing agent is anhydrous magnesium sulfate or quality is 55%-65% circular regenerations.
The Karst catalyst is chloroplatinic acid and the mixed solution of t etram-ethyltetravinylcyclotetrasiloxane；
The schiff bases ketimine structure formula is：（CH3）2C=NCH2CH=CH2
The silane intermediate structural formula is：（CH3）2C=NCH2CH2CH2Si(OC2H5)3
The present invention composition principle be：
CH3COCH3+NH2CH2CH=CH2---（CH3）2C=NCH2CH=CH2+H2O
（Schiff bases ketimide）
MgSO4 +H2O----MgSO4·7H2O
（CH3）2C=NCH2CH=CH2+HSi(OC2H5)3—
（CH3）2C=NCH2CH2CH2Si(OC2H5)3
(silane intermediate)
（CH3）2C=NCH2CH2CH2Si(OC2H5)3 +H2O-----
N2CH2CH2CH2Si(OC2H5)3 + CH3COCH3
(aminopropyl triethoxysilane product)
Water absorbing agent anhydrous magnesium sulfate regenerates：
MgSO4·7H2O Heating MgSO4·2H2O
The beneficial effects of the present invention are：
1. the present invention first with acetone and allyl amine synthesis schiff bases ketimide, protects the amino group of allyl amine,
The activity and structure of allyl amine are changed, makes it in the generation that same triethoxysilane addition is no isomer, only
There is the appearance of γ addition compound products, the quality and yield of addition compound product are improved, so as to ensure that aminopropyl triethoxysilane
The quality and yield of product；
2. pair equipment requirement is not high, technological operation is easy, and raw material is easy to get；
3. no coupling product generates, safety and environmental protection, raw material acetone can be recycled, after anhydrous magnesium sulfate use can 100~
120 DEG C of dryings regenerate after removing water 4 hours, reuse.
Specific embodiment
Embodiment 1：
2.2mol is added in 1L four-hole boiling flasks（127.8 gram）Acetone and 2 mol（114.2 gram）Allyl amine adds
51.0 grams of anhydrous magnesium sulfates after the completion of feeding intake, open stirring, and speed of agitator is 120 revs/min, and it is anti-that kettle temperature is raised to 55 DEG C of heat preservations
After answering 5 hours, then temperature is raised to 70 DEG C of distillations, obtains 0.17mol（9.8 gram）The complete raw material acetone of unreacted.It will finally burn
Bottle is cooled to less than 30 DEG C filterings, filtrate 1.95mol（189.4 gram）Schiff bases ketimide, filter residue are 92.7 grams of aqueous sulphur
Sour magnesium crystal.92.7 grams of aqueous magnesium sulfate crystals of filter residue obtain 66.8 grams containing two molecules after being toasted 4 hours in 110 DEG C of baking ovens
The regenerated magnesium sulfate of water, keeps reuse.
1.95mol is added in 1L four-hole boiling flasks（189.4 gram）Above-mentioned filtrate schiff bases ketimide and 1 microlitre of Karst are urged
Agent opens magnetic stirring apparatus, and rotating speed is 60 revs/min, and kettle temperature is raised to 1.99 mol in 75 DEG C, 4 hours（326.9 gram）Three
Ethoxysilane is added drop-wise in flask, and aging is distilled after 2 hours under -0.098MPa at 75 DEG C after being added dropwise, and is obtained
1.95mol（508.8 gram）Silane intermediate.
1.95mol is added in 1L four-hole boiling flasks（508.8 gram）The silane intermediate that above-mentioned distillation obtains is opened magnetic force and is stirred
Device is mixed, rotating speed is 60 revs/min, and kettle temperature is raised to 1.94 mol in 70 DEG C, 2 hours（34.7 grams）Deionized water is added drop-wise to flask
In, after being added dropwise at 80 DEG C after aging 1 hour, then distill out under -0.098MPa the low-boiling point material third of reaction generation
Ketone 1.94mol（112.8 gram）, after cooling in flask be 1.93 mol（428.6 gram）Aminopropyl triethoxysilane product, gas phase
It is 98.8% that chromatography, which detects its content, product yield about 96%.
Embodiment 2：
9.8 grams and 112.8 grams of the acetone that embodiment 1 is distilled to recover is added in 1L four-hole boiling flasks, adds new acetone 5.2
Gram common 2.2mol（127.8 gram）With 2 mol（114.2 gram）Allyl amine adds after embodiment 1 regenerates and contains two molecules for 68.8 grams
The magnesium sulfate of water after the completion of feeding intake, opens stirring, and speed of agitator is 120 revs/min, and kettle temperature is raised to 55 DEG C of insulation reactions 5 hours
Afterwards, then by temperature 60 DEG C of distillations are raised to, obtain 0.16mol（9.2 gram）The complete raw material acetone of unreacted.Finally flask is cooled to
Less than 30 DEG C filterings, filtrate 1.95mol（189.7 gram）Schiff bases ketimide, the filter residue magnesium sulfate aqueous for 110.4 grams are brilliant
Body.
110.4 grams of aqueous magnesium sulfate crystals of filter residue obtain 74.2 grams containing two molecules after being toasted 4 hours in 110 DEG C of baking ovens
The magnesium sulfate of water keeps reuse.
1.95mol is added in 1L four-hole boiling flasks（189.7 gram）Above-mentioned filtrate schiff bases ketimide and 1 microlitre of Karst are urged
Agent opens magnetic stirring apparatus, and rotating speed is 60 revs/min, and kettle temperature is raised to 1.99 mol in 70 DEG C, 4 hours（326.9 gram）Three
Ethoxysilane is added drop-wise in flask, and aging is distilled after 2 hours under -0.098MPa at 80 DEG C after being added dropwise, and is obtained
1.93mol（505.7 gram）Silane intermediate.
1.93mol is added in 1L four-hole boiling flasks（505.7 gram）The silane intermediate that above-mentioned distillation obtains is opened magnetic force and is stirred
Device is mixed, rotating speed is 60 revs/min, and kettle temperature is raised to 1.93 mol in 60 DEG C, 2 hours（34.4 grams）Deionized water is added drop-wise to flask
In, after being added dropwise at 70 DEG C after aging 1 hour, then distill out under -0.098MPa the low-boiling point material third of reaction generation
Ketone 1.92mol（111.2 gram）, after cooling in flask be 1.92 mol（425.7 gram）Aminopropyl triethoxysilane product, gas phase
It is 99.0% that chromatography, which detects its content, product yield about 96%.
Embodiment 3：
22mol is added in 10L four-hole boiling flasks（1278 grams）Acetone and 20mol（1142 grams）Allyl amine adds 510
Gram anhydrous magnesium sulfate after the completion of feeding intake, opens stirring, and speed of agitator is 120 revs/min, and it is small that kettle temperature is raised to 55 DEG C of insulation reactions 5
Shi Hou, then temperature is raised to 65 DEG C of distillations, obtain 1.92mol（112 grams）The complete raw material acetone of unreacted.Finally flask is cooled down
To less than 30 DEG C filterings, filtrate 19.6mol（1908 grams）Schiff bases ketimide, filter residue are 907 grams of aqueous magnesium sulfate crystals.
907 grams of aqueous magnesium sulfate crystals of filter residue obtain 665 grams containing two molecular waters after being toasted 4 hours in 110 DEG C of baking ovens
Regenerated magnesium sulfate, keep reuse.
19.6mol is added in 10L four-hole boiling flasks（1908 grams）Above-mentioned filtrate schiff bases ketimide and 10 microlitres of Karst
Catalyst opens magnetic stirring apparatus, and rotating speed is 60 revs/min, and kettle temperature is raised to 20.0 mol in 73 DEG C, 4 hours（3286 grams）
Triethoxysilane is added drop-wise in flask, after being added dropwise at 78 DEG C after aging 2 hours, then is distilled, is obtained under -0.098MPa
To 19.6mol（5123 grams）Silane intermediate.
19.6mol is added in 10L four-hole boiling flasks（5123 grams）The silane intermediate that above-mentioned distillation obtains is opened magnetic force and is stirred
Device is mixed, rotating speed is 60 revs/min, and kettle temperature is raised to 19.4 mol in 65 DEG C, 2 hours（349 grams）Deionized water is added drop-wise to flask
In, aging distills out the low-boiling point material acetone of reaction generation under -0.098MPa at 75 DEG C after 1 hour after being added dropwise
19.3mol（1121 grams）, after cooling in flask be 19.6 mol（4348 grams）Aminopropyl triethoxysilane product, gas-chromatography
It is 98.9% to detect its content, product yield about 98%.
Embodiment 4：
112 grams and 1121 grams of the acetone that embodiment 3 is distilled to recover is added in 10L four-hole boiling flasks, adds new acetone 45
Gram common 22mol（1278 grams）With 20 mol（1142 grams）Allyl amine adds after embodiment 3 regenerates and contains two molecular waters for 665 grams
Magnesium sulfate, after the completion of feeding intake, open stirring, speed of agitator is 120 revs/min, and kettle temperature is raised to 55 DEG C of insulation reactions 5 hours
Afterwards, then by temperature 68 DEG C of distillations are raised to, obtain 1.90mol（110 grams）The complete raw material acetone of unreacted.Finally flask is cooled to
Less than 30 DEG C filterings, filtrate 19.5mol（1894 grams）Schiff bases ketimide, filter residue are 1077 grams of aqueous magnesium sulfate crystals.
1077 grams of aqueous magnesium sulfate crystals of filter residue obtain 708 grams containing two molecular waters after being toasted 4 hours in 110 DEG C of baking ovens
Magnesium sulfate, keep reuse.
19.5mol is added in 10L four-hole boiling flasks（1894 grams）Above-mentioned filtrate schiff bases ketimide and 10 microlitres of Karst
Catalyst opens magnetic stirring apparatus, and rotating speed is 60 revs/min, and kettle temperature is raised to 19.9 mol in 72 DEG C, 4 hours（3270 grams）
Triethoxysilane is added drop-wise in flask, after being added dropwise at 75~80 DEG C after aging 2 hours, then is steamed under -0.098MPa
It evaporates, obtains 19.4mol（5073 grams）Silane intermediate.
19.4mol is added in 10L four-hole boiling flasks（5073 grams）The silane intermediate that above-mentioned distillation obtains is opened magnetic force and is stirred
Device is mixed, rotating speed is 60 revs/min, and kettle temperature is raised to 19.2 mol in 68 DEG C, 2 hours（346 grams）Deionized water is added drop-wise to flask
In, after being added dropwise at 75 DEG C after aging 1 hour, then distill out under -0.098MPa the low-boiling point material third of reaction generation
Ketone 19.2mol（1116 grams）, after cooling in flask be 19.3 mol（4281 grams）Aminopropyl triethoxysilane product, gas phase color
It is 99.1% that spectrum, which detects its content, product yield about 97%.
Claims (3)
1. a kind of synthetic method of aminopropyl triethoxysilane；It is characterized in that：It includes the following steps：
1）, by acetone and allyl amine in molar ratio 1.1~1.5：1 rate of charge is put into reaction vessel；By thrown allyl
The 45% of base amine weight adds in water absorbing agent；After the completion of feeding intake, 50~55 DEG C are warming up under 120~150 revs/min of mixing speed,
After insulation reaction 5~6 hours, it is then warming up to 60~70 DEG C again and distills out the complete raw material acetone of unreacted；
2）, acetone distillation after be cooled to less than 30 DEG C filterings, obtain schiff bases ketimide；Filter residue is aqueous magnesium sulfate,
Magnesium sulfate is reused after can heating regeneration；The complete raw material acetone of unreacted can be recycled；
3）, the schiff bases ketimide being obtained by filtration put into the reactor with magnetic agitation, in 60~90 revs/min of stirring
70~75 DEG C are warming up under speed, adds in Karst catalyst, then triethoxysilane, triethoxysilicane were added dropwise in 4 hours
Alkane is 1 with schiff bases ketimide molar ratio：1.01~1.05, triethoxysilane is old at 75~80 DEG C after being added dropwise
It is distilled under the conditions of -0.098MPa after changing 1~2 hour, obtains silane intermediate；
4）, silane intermediate put into the reactor with magnetic agitation, be warming up under 60~90 revs/min of mixing speed
60~70 DEG C, then deionized water was added dropwise in 2 hours, the molar ratio of silane intermediate and deionized water is 1.01：1, drop
Aging is distilled 2 hours under -0.098MPa again after 1~2 hour at 70~80 DEG C after adding, and steams low-boiling point material third
Ketone；Then reactor is cooled down, obtains aminopropyl triethoxysilane finished product；The low-boiling point material acetone distilled out, which is recycled, to be made
With.
2. a kind of synthetic method of aminopropyl triethoxysilane according to claim 1；It is characterized in that：The suction
The aqueous magnesium sulfate that aqua is anhydrous magnesium sulfate or quality is 55%-65% circular regenerations.
3. a kind of synthetic method of aminopropyl triethoxysilane according to claim 1；It is characterized in that：The card
This special catalyst is chloroplatinic acid and the mixed solution of t etram-ethyltetravinylcyclotetrasiloxane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610142413.2A CN105669739B (en) | 2016-03-14 | 2016-03-14 | A kind of synthetic method of aminopropyl triethoxysilane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610142413.2A CN105669739B (en) | 2016-03-14 | 2016-03-14 | A kind of synthetic method of aminopropyl triethoxysilane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105669739A CN105669739A (en) | 2016-06-15 |
| CN105669739B true CN105669739B (en) | 2018-06-08 |
Family
ID=56308235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610142413.2A Active CN105669739B (en) | 2016-03-14 | 2016-03-14 | A kind of synthetic method of aminopropyl triethoxysilane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105669739B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111495429B (en) * | 2020-04-14 | 2023-11-10 | 南昌大学 | Preparation method of efficient composite catalyst and preparation method of silane coupling agent KH-560 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2185984B (en) * | 1986-01-30 | 1989-12-06 | Dow Corning | Preparation of primary aminosiloxanes |
| JPH03184983A (en) * | 1989-12-13 | 1991-08-12 | Toshiba Silicone Co Ltd | Amino group-containing silane |
-
2016
- 2016-03-14 CN CN201610142413.2A patent/CN105669739B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2185984B (en) * | 1986-01-30 | 1989-12-06 | Dow Corning | Preparation of primary aminosiloxanes |
| JPH03184983A (en) * | 1989-12-13 | 1991-08-12 | Toshiba Silicone Co Ltd | Amino group-containing silane |
Non-Patent Citations (2)
| Title |
|---|
| Alpha-amino silanes via metalated imines as an approach to the synthesis of silanediol protease inhibitors;Yingjian Bo等,;《Tetrahedron》;20130614;7779-7784页 * |
| Synthesis of Siloxanes Containing Reactive Side Chains;S. K. Duplock等,;《Journal of Inorganic Organometallic Polymers》;19910930;361-375页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105669739A (en) | 2016-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102532186B (en) | Method for preparing hydroxyimino organosilicon compounds | |
| CN104860977B (en) | A kind of siliceous aromatic diamine and preparation method thereof | |
| CN105669739B (en) | A kind of synthetic method of aminopropyl triethoxysilane | |
| CN102746161A (en) | Method for synthesizing 1,8-terpene diamine | |
| CN107936052A (en) | A kind of preparation method of different alkane alkenyloxy group silane | |
| CN102604070A (en) | Synthesis method for polyether polyol flame retardant | |
| CN104017017A (en) | Method for synthesizing phenyl-containing organosilicon monomers | |
| CN104945255B (en) | Preparation method of cyclohexyl methacrylate | |
| JPH0416476B2 (en) | ||
| US9783476B2 (en) | Method of producing 2′-trifluoromethyl group-substituted aromatic ketone | |
| WO1991019696A1 (en) | Process for producing n-substituted aziridine compound | |
| CN105732694A (en) | Method for adsorbing and purifying 1, 1, 1, 3, 5, 5, 5-heptamethyltrisiloxane | |
| CN103113400B (en) | The method of synthesis of phenyl methyl dioxane TMOS | |
| CN112480161B (en) | Aminopropyl trimethoxy silane and preparation method thereof | |
| JP5591856B2 (en) | (Meth) acrylamide compound precursor | |
| CN108409779A (en) | A kind of preparation method of γ-aminopropyl trisiloxane | |
| CN103342715A (en) | Preparation method of aminopropyl-containing organic oximido-silicon compound | |
| CN109824714B (en) | Synthetic method of cyclic silicon nitrogen amino silane | |
| CN101723965B (en) | Method for preparing gama-(acryloyloxy)-propyl trialkoxy silane monomer | |
| CN101845055B (en) | Method for purifying dichloromethyl phenylsilane by chemical coordination effect | |
| CN105622660A (en) | Preparation method of secondary amido silane coupling agent and preparation method of catalyst thereof | |
| CN100506826C (en) | Triphenylacetylene silane novle synthesis method | |
| CN105693758A (en) | Preparation method of trimerization isocyan urea acid ester silane | |
| CN105399763A (en) | Synthetic method for glycidyl ether oxysilane | |
| CN110172024A (en) | A method of anhydrous ethylenediamine is produced from diamine base silane by-product ethylenediamine-hydrochloride |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CP03 | Change of name, title or address | ||
| CP03 | Change of name, title or address |
Address after: Luochang Town, Shashi District, Jingzhou City, Hubei Province Patentee after: Hubei Jianghan New Material Co.,Ltd. Address before: 434000 No.2 Road, Shashi District Economic and Technological Development Zone, Jingzhou City, Hubei Province Patentee before: JINGZHOU JIANGHAN FINE CHEMICAL Co.,Ltd. |