CN107759627A - The synthesizer and its synthetic method of the NCO propyl-triethoxysilicane of high-purity 3 - Google Patents
The synthesizer and its synthetic method of the NCO propyl-triethoxysilicane of high-purity 3 Download PDFInfo
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- 238000010189 synthetic method Methods 0.000 title claims description 40
- 239000007788 liquid Substances 0.000 claims abstract description 30
- 230000001681 protective effect Effects 0.000 claims abstract description 27
- 239000002994 raw material Substances 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 238000000926 separation method Methods 0.000 claims abstract description 14
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- 230000035484 reaction time Effects 0.000 claims abstract description 8
- -1 [3-(triethoxysilyl) propyl] ethyl Chemical group 0.000 claims abstract description 5
- 238000004227 thermal cracking Methods 0.000 claims abstract description 5
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 4
- 230000015572 biosynthetic process Effects 0.000 claims abstract 2
- 239000007789 gas Substances 0.000 claims description 72
- 239000007787 solid Substances 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 239000011521 glass Substances 0.000 claims description 13
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 11
- 229910052710 silicon Inorganic materials 0.000 claims description 11
- 239000010703 silicon Substances 0.000 claims description 11
- 229910001220 stainless steel Inorganic materials 0.000 claims description 6
- 239000010935 stainless steel Substances 0.000 claims description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052573 porcelain Inorganic materials 0.000 claims description 3
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 3
- 230000006837 decompression Effects 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical group [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims 1
- 238000001514 detection method Methods 0.000 abstract description 7
- 238000004817 gas chromatography Methods 0.000 abstract description 3
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000001816 cooling Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- 239000000758 substrate Substances 0.000 description 14
- PKDCQJMRWCHQOH-UHFFFAOYSA-N triethoxysilicon Chemical compound CCO[Si](OCC)OCC PKDCQJMRWCHQOH-UHFFFAOYSA-N 0.000 description 14
- 150000003673 urethanes Chemical class 0.000 description 14
- 239000004579 marble Substances 0.000 description 8
- 238000003763 carbonization Methods 0.000 description 7
- 230000033228 biological regulation Effects 0.000 description 6
- 238000007689 inspection Methods 0.000 description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- 238000007599 discharging Methods 0.000 description 5
- 238000000197 pyrolysis Methods 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005086 pumping Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000007701 flash-distillation Methods 0.000 description 2
- 230000008676 import Effects 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QJHOWMKBGGKETF-RGMNGODLSA-N C(CC)N[C@@H](CCO)C(=O)O.[Pt] Chemical compound C(CC)N[C@@H](CCO)C(=O)O.[Pt] QJHOWMKBGGKETF-RGMNGODLSA-N 0.000 description 1
- WBBAJOWRWNEUNX-UHFFFAOYSA-N CCCC(NCCC[SiH-](OCC)(OCC)OCC)=O Chemical compound CCCC(NCCC[SiH-](OCC)(OCC)OCC)=O WBBAJOWRWNEUNX-UHFFFAOYSA-N 0.000 description 1
- 125000006519 CCH3 Chemical group 0.000 description 1
- 0 CCO*(CCCN)(OCC)OCC Chemical compound CCO*(CCCN)(OCC)OCC 0.000 description 1
- 229910001018 Cast iron Inorganic materials 0.000 description 1
- 239000004593 Epoxy Chemical group 0.000 description 1
- 229910004721 HSiCl3 Inorganic materials 0.000 description 1
- 229910018540 Si C Inorganic materials 0.000 description 1
- 229910018557 Si O Inorganic materials 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- UPHIPHFJVNKLMR-UHFFFAOYSA-N chromium iron Chemical compound [Cr].[Fe] UPHIPHFJVNKLMR-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000110 cooling liquid Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000012774 insulation material Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- 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 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
高纯度3‑异氰酸酯基丙基三乙氧基硅烷的合成装置及其合成方法，它属于化学合成领域。本发明合成方法包括如下步骤：加热固定床反应器到350℃～400℃并保持温度，待用；调节减压阀将固定床反应器中通入保护气体，通入保护气体3～30min后，采用计量泵将原料[3‐(三乙氧基硅基)丙基]氨基甲酸乙酯通入固定床反应器，进行热裂解反应，反应时间2～4h；步骤2反应后的混合物通过第一冷凝器冷却，所述的第一冷凝器采用80℃热水冷却，冷却后的混合物进入气液分离器分离，分离后的液体通过冷却器进入到产物接收罐。本发明得到高纯度3‑异氰酸酯基丙基三乙氧基硅烷97.5g，收率81.3％，气相色谱检测纯度99.19％生产过程更安全，工艺更简单，产品易分离，反应原料完全转化。
A high-purity 3-isocyanatopropyltriethoxysilane synthesis device and a synthesis method thereof belong to the field of chemical synthesis. The synthesis method of the present invention comprises the following steps: heating the fixed-bed reactor to 350° C. to 400° C. and maintaining the temperature for use; adjusting the pressure reducing valve to pass protective gas into the fixed-bed reactor, and after passing the protective gas for 3 to 30 minutes, The raw material [3-(triethoxysilyl) propyl] ethyl carbamate is passed into the fixed-bed reactor by a metering pump for a thermal cracking reaction, and the reaction time is 2 to 4 hours; the mixture after the reaction in step 2 passes through the first The condenser is cooled, and the first condenser is cooled with 80°C hot water. The cooled mixture enters the gas-liquid separator for separation, and the separated liquid enters the product receiving tank through the cooler. The invention obtains 97.5 g of high-purity 3-isocyanatopropyl triethoxysilane with a yield of 81.3 percent and a gas chromatography detection purity of 99.19 percent. The production process is safer, the process is simpler, the product is easy to separate, and the reaction raw materials are completely converted.
Description
Technical field
The invention belongs to the field of chemical synthesis, and in particular to a kind of high-purity 3- NCO propyl-triethoxysilicanes
Synthesizer and its synthetic method.
Background technology
Silane coupler is a kind of low molecule organo-silicon compound with special construction, and its formula is RSiX3, R in formula
Represent the groups such as amino, sulfydryl vinyl, epoxy radicals, chloropropyl, cyano group and methacryloxy, these groups and different
Matrix resin is respectively provided with stronger respond, and x represents the group that can be hydrolyzed, such as halogen, alkoxy, acyloxy.
Silane coupler is by trichlorosilane (HSiCl3) and unsaturated olefin with reactive group urged in platinum propylhomoserin
Change lower addition, then obtained through alcoholysis.Silane coupler can be with the length point in the hydroxyl and can in inorganic matter and organic polymer
Subchain interacts, and makes two kinds of material couplings of different nature, so as to improve the various performances of material.
Silane coupler containing isocyanates is a kind of new coupling agent, and it is in surface treatment organic material and inorganic gold
There is very excellent effect during category, composite, processing inorganic powdered filler and coating oil particularly in glass fiber reinforcement
There is significant effect in the tackifier of ink.3- isocyanatopropyl triethoxysilanes are most important of which containing isocyanates
Silane coupler, China is expensive mainly from Japanese import, and general both at home and abroad to use phosgenation, prepared by solid phosgene, no matter
Phosgenation, or the raw materials technology toxicity of solid phosgene method are all larger, and yield is relatively low.Obtained using diethyl carbonate two step method
To 3- isocyanatopropyl triethoxysilanes, technique is simple, more competitive method.Comprise the following steps that：
Step 1,1, APTES and diethyl carbonate react to obtain [3- (triethoxy silicon substrate) third
Base] urethanes, reaction equation is：
Step 2, by a certain amount of pumping fluid as in round-bottomed flask, be warming up to 320-340 DEG C, the production that the first step is obtained
Product [3- (triethoxy silicon substrate) propyl group] urethanes is slowly instilled in deep fat, and thermal cracking occurs, and high vacuum flashes to obtain
Crude product, again rectifying obtain target product, purity 98%.Reaction equation is：
The technique have two it is obvious the shortcomings that, using substantial amounts of pumping fluid or mineral oil, and need to regularly replace；Adopt
It is high vacuum flash distillation, the residual of raw material is had in product, need to be through handling to obtain product again.
The content of the invention
The invention aims to solve the mistake of diethyl carbonate two step synthetic method 3- isocyanatopropyl triethoxysilanes
The problems such as residual and the substantial amounts of pumping fluid of consumption or mineral oil of raw material are had in journey, and it is different to provide a kind of high-purity 3-
The synthesizer and its synthetic method of cyanic acid ester group propyl-triethoxysilicane.
The present invention is achieved through the following technical solutions：
A kind of synthesizer of high-purity 3- NCO propyl-triethoxysilicanes, described high-purity 3- isocyanic acids
The synthesizer of ester group propyl-triethoxysilicane includes fixed bed reactors, and described fixed bed reactors are arranged on heating furnace
In, solid carrier is housed, the top of described fixed bed reactors is provided with charging aperture, protection in described fixed bed reactors
Gas access, the charging aperture of described fixed bed reactors connect measuring pump by pipeline, and described measuring pump is connected by pipeline
Hopper is tapped into, the gas atmosphere inlet of described fixed bed reactors connects pressure-reducing valve by pipeline, and described pressure-reducing valve passes through
Pipeline connects gas cylinder, and the bottoms of described fixed bed reactors is provided with discharging opening, and described discharging opening passes through pipeline connection the
The entrance of one condenser, the entrance of the outlet connection gas-liquid separator of the first described condenser, described gas-liquid separator
Outlet connect the second condenser, cooler respectively, described cooler connection product receiving tank, the second described condenser
Outlet connects ethanol receiving tank, gas flowmeter respectively.
The synthesizer of high-purity 3- NCO propyl-triethoxysilicanes of the present invention, described heating furnace
By SCR control, described controllable silicon connection thermocouple, described thermocouple is inserted inside described fixed bed reactors.
The synthesizer of high-purity 3- NCO propyl-triethoxysilicanes of the present invention, described solid carry
Body is upper and lower two layers, and described lower floor's solid carrier is carbonization silicon ball, and described upper strata solid carrier is glass marble, porcelain ball, glass
One kind in glass ball, alumina balls or stainless steel ball.
The synthesizer of high-purity 3- NCO propyl-triethoxysilicanes of the present invention, described lower floor consolidates
A diameter of 4mm~16mm of a diameter of solid carrier of body carrier, a diameter of solid carrier of described upper strata solid carrier
A diameter of 4mm~16mm.
The synthesizer of high-purity 3- NCO propyl-triethoxysilicanes of the present invention, described lower floor consolidates
A diameter of 4mm, 6mm, 10mm, 12mm of body carrier, a diameter of 4mm, 6mm, 8mm of described upper strata solid carrier.
The synthesizer of high-purity 3- NCO propyl-triethoxysilicanes of the present invention, heating furnace add for electricity
Hot stove, it is that two semicircles are pressed into by stainless sheet steel (surface favin), both ends assembling cast iron chromium plating end cap forms two semicircles
Bucket, then one side of two and half drum bodies of heater is connected with stainless steel hinge, another side is combined into import stainless steel up to button installation
Body of heater, the outer opening and closing place of body of heater are simultaneously furnished with stainless steel handle, can freely open or close Liang Geban gardens stove, installed in stove and seal in conjunction
Golden resistance wire and the carborundum tile for tamping the material of thermostable heat-conductive insulation, and ceramic wool insulation material, shell be equipped with
Terminal box (having two kinds of modes of connection in parallel and serial between the stove of two halves garden) and body of heater the installation fixed triangle frame of power supply wiring.Its
Technical parameter is that body of heater size is external diameter 500mm, internal diameter 105mm, height 700mm；Power error scope：± 5%；Insulation is strong
Degree：≥5MΩ；The gap of tile and reactor：2-3mm；Operating temperature：200-1200℃.The application method of electric furnace：Will
The mounting and fixing support of body of heater correctly installs (vertical)；Reactor is arranged in stove and stove is shut after stove is opened and is closed
Hasp；The wiring on each section of control plant-grid connection body of heater is closed respectively by each section of heating distribution of stove, and inserts thermocouple；
Check the insulation degree of body of heater, and effective grounding, determine it is errorless after can start shooting work.
The synthesizer of high-purity 3- NCO propyl-triethoxysilicanes of the present invention, using nitrogen steel
Bottle, is connected by silicone tube with fixed bed reactors.
The synthesizer of high-purity 3- NCO propyl-triethoxysilicanes of the present invention, gas flow are calculated as
Wet flow indicator.
The synthesizer of high-purity 3- NCO propyl-triethoxysilicanes of the present invention, using nitrogen steel
Bottle, is connected by silicone tube with fixed bed reactors, and the top of described fixed bed reactors is cylinder, the diameter of cylinder
It is highly 600mm for 60mm, solid carrier is placed in the Upper cylindrical body of described fixed bed reactors, described fixed bed
The bottom of reactor is circular cone halfpace, and the whole height of described fixed bed reactors is 800mm, and described thermocouple inserts institute
500mm in the fixed bed reactors stated, described charging aperture, described gas atmosphere inlet are respectively arranged at described fixed bed
The left and right sides on reactor top, the discharging openings of described fixed bed reactors are ground, ground diameter 24mm.
The synthesizer of high-purity 3- NCO propyl-triethoxysilicanes of the present invention, described gas-liquid point
It is vertical gas-liquid separator from device, described cooler is the glass spherical condenser pipe.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes of the present invention, including following step
Suddenly：
The air-tightness of the synthesizer of the described high-purity 3- NCO propyl-triethoxysilicanes of step 1, inspection,
Fixed bed reactors are heated to 350 DEG C~400 DEG C and keeping temperature, it is stand-by；
Step 2, regulation pressure-reducing valve will be passed through protective gas in fixed bed reactors, after being passed through 3~30min of protective gas,
Raw material [3- (triethoxy silicon substrate) propyl group] urethanes is passed through by fixed bed reactors using measuring pump, carries out thermal cracking
Reaction, 2~4h of reaction time；
The reacted mixture of step 3, step 2 is cooled down by the first condenser, and the first described condenser uses 80 DEG C
Hot water cools down, and the mixture after cooling enters gas-liquid separator separates, and the liquid after separation enters product by cooler and connect
Closed cans, the gas after separation enter the second condenser, and the second described condenser is cooled down using 5~15 DEG C of cold water, after cooling
Liquid enters ethanol receiving tank, and the gas after cooling is vented by gas flowmeter.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes of the present invention, described in step 2
Protective gas be nitrogen, shield gas flow rate is air speed 3000h-1~10000h-1。
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes of the present invention, raw material in step 2
The addition of [3- (triethoxy silicon substrate) propyl group] urethanes is 20g/h~150g/h.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes of the present invention, in step 3
Two condensers are cooled down using 5 DEG C of cold water.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes of the present invention, it is passed through in step 2
3~30min of protective gas, it is therefore an objective to all replace the air in reaction vessel.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes of the present invention, it is anti-using fixed bed
Answer device to substitute high vacuum flash distillation, the time of raw material thermal cracking is adjusted by the flow velocity of nitrogen, raw material is converted, do not had in product completely
The residual of raw material；Without using mineral oil or pumping fluid in technique, technique is simpler, easy to operate, and it is different to finally obtain high-purity 3-
Cyanic acid ester group propyl-triethoxysilicane 97.5g, yield 81.3%, gas chromatographic detection purity 99.19%.
Brief description of the drawings
Fig. 1 is the structural representation of the present invention；
Fig. 2 is the structural representation of fixed bed reactors of the present invention；
Fig. 3 is the infrared of high-purity 3- NCO propyl-triethoxysilicanes prepared by the method for embodiment two
Absorb spectrogram；
Fig. 4 is the nuclear-magnetism of high-purity 3- NCO propyl-triethoxysilicanes prepared by the method for embodiment two
Collection of illustrative plates；
Fig. 5 is the gas phase of high-purity 3- NCO propyl-triethoxysilicanes prepared by embodiment tripartite method
Chromatogram.
Embodiment
Embodiment one：
A kind of synthesizer of high-purity 3- NCO propyl-triethoxysilicanes, described high-purity 3- isocyanic acids
The synthesizer of ester group propyl-triethoxysilicane includes fixed bed reactors 1, and described fixed bed reactors are arranged on heating
In stove 5, solid carrier 18 is housed, the top of described fixed bed reactors is provided with charging aperture in described fixed bed reactors
17th, gas atmosphere inlet 16, the charging aperture of described fixed bed reactors connect measuring pump 12, described measuring pump by pipeline
Material feeding box 14 is connected by pipeline, the gas atmosphere inlet of described fixed bed reactors connects pressure-reducing valve 2 by pipeline, described
Pressure-reducing valve by pipeline connect gas cylinder 3, the bottom of described fixed bed reactors is provided with discharging opening 19, described discharging opening
The entrance of the first condenser 6 is connected by pipeline, the outlet of the first described condenser connects the entrance of gas-liquid separator 7,
The outlet of described gas-liquid separator connects the second condenser 11, cooler 8, described cooler connection product receiving tank respectively
9, the outlet of the second described condenser connects ethanol receiving tank 10, gas flowmeter 13 respectively.
The synthesizer of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, described adds
Hot stove is controlled by controllable silicon 4, described controllable silicon connection thermocouple 15, the described fixed bed reactors of described thermocouple insertion
It is internal.
The synthesizer of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, described consolidates
Body carrier is upper and lower two layers, and described lower floor's solid carrier is carbonization silicon ball, and described upper strata solid carrier is glass marble, porcelain
One kind in ball, glass marble, alumina balls or stainless steel ball.
The synthesizer of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, under described
A diameter of 4mm~16mm of a diameter of solid carrier of layer solid carrier, a diameter of solid of described upper strata solid carrier carry
A diameter of 4mm~16mm of body.
Embodiment two：
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes according to embodiment one,
Comprise the following steps：
The air-tightness of the synthesizer of the described high-purity 3- NCO propyl-triethoxysilicanes of step 1, inspection,
Fixed bed reactors are heated to 350 DEG C and keeping temperature, it is stand-by；
Step 2, regulation pressure-reducing valve will be passed through protective gas in fixed bed reactors, after being passed through protective gas 10min, use
Raw material [3- (triethoxy silicon substrate) propyl group] urethanes is passed through fixed bed reactors by measuring pump, carries out Pyrolysis
Should, reaction time 2h；
The reacted mixture of step 3, step 2 is cooled down by the first condenser, and the first described condenser uses 80 DEG C
Hot water cools down, and the mixture after cooling enters gas-liquid separator separates, and the liquid after separation enters product by cooler and connect
Closed cans, the gas after separation enter the second condenser, and the second described condenser is cooled down using 10 DEG C of cold water, the liquid after cooling
Ethanol receiving tank is entered, the gas after cooling is vented by gas flowmeter.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, in step 2
Described protective gas is nitrogen, and shield gas flow rate is air speed 4000h-1, the now flow 200L/h of nitrogen.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, in step 2
The addition of raw material [3- (triethoxy silicon substrate) propyl group] urethanes is 60g/h.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, under described
Layer solid carrier is carbonization silicon ball, and a diameter of 6mm, described upper strata solid carrier is glass marble, a diameter of 6mm.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, is finally obtained
High-purity 3- NCO propyl-triethoxysilicane 97.5g, yield 81.3%, gas chromatographic detection purity 99.19%.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, accompanying drawing 3 are
The infrared absorption spectra of high-purity 3- NCO propyl-triethoxysilicanes prepared by the method for embodiment two, Fourier
Leaf transformation infrared spectrum (FT-IR) is measured using Nicolet FT-IR200XB type infrared spectrometers.Abscissa
Wavenumber represents wave number, and ordinate represents transmitance.
It can be drawn in the infrared spectrum：- N=C=O characteristic absorption peak 2272.9cm-1；In 1081.3cm-1Place goes out
Existing strong broad peak is Si-O stretching vibration；In 1103.7cm-1,1166.7cm-1Symmetrical stretching vibration is Si-O-C feature
Peak；799(690-890)cm-1The strong peak for stretching vibration occur is Si-C.
Accompanying drawing 4 is the core of high-purity 3- NCO propyl-triethoxysilicanes prepared by the method for embodiment two
Magnetic chart is composed, and the molecular formula of 3- NCO propyl-triethoxysilicanes is C10H21NO4Si, shown as in nuclear magnetic spectrum1HNMR (300MHz, Chloroform-d) δ 3.84 (q, J=7.0Hz, 6H, C-CH2- O), 3.31 (t, J=6.8Hz, 2H, C-
CH2-N),1.83–1.66(m,2H,C-CH2- C), 1.25 (t, J=7.0Hz, 9H, C-CH3),0.77–0.61(m,2H,Si-
CH2-C)。
Accompanying drawing 5 is the gas of high-purity 3- NCO propyl-triethoxysilicanes prepared by embodiment tripartite method
Phase chromatogram, the gas chromatograph used is tested as Agilent Technologies 7820A, chromatographic column HP-5, program liter
Temperature, product is dissolved in methylene chloride and detected, first peak is that solvent peak needs to deduct in figure, retention time
It is within 5.116 minutes the peak of product, the integral result for deducting solvent peak is shown in Table 1：
The data from gas chromatography analytical table of the high-purity 3- NCO propyl-triethoxysilicanes of table 1
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, gas-chromatography
Testing result be product purity 99.19%.
Embodiment three：
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes according to embodiment one,
Comprise the following steps：
The air-tightness of the synthesizer of the described high-purity 3- NCO propyl-triethoxysilicanes of step 1, inspection,
Fixed bed reactors are heated to 370 DEG C and keeping temperature, it is stand-by；
Step 2, regulation pressure-reducing valve will be passed through protective gas in fixed bed reactors, after being passed through protective gas 10min, use
Raw material [3- (triethoxy silicon substrate) propyl group] urethanes is passed through fixed bed reactors by measuring pump, carries out Pyrolysis
Should, reaction time 2h；
The reacted mixture of step 3, step 2 is cooled down by the first condenser, and the first described condenser uses 80 DEG C
Hot water cools down, and the mixture after cooling enters gas-liquid separator separates, and the liquid after separation enters product by cooler and connect
Closed cans, the gas after separation enter the second condenser, and the second described condenser is cooled down using 10 DEG C of cold water, the liquid after cooling
Ethanol receiving tank is entered, the gas after cooling is vented by gas flowmeter.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, in step 2
Described protective gas is nitrogen, and shield gas flow rate is air speed 5000h-1, the now flow 250L/h of nitrogen.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, in step 2
The addition of raw material [3- (triethoxy silicon substrate) propyl group] urethanes is 60g/h.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, under described
Layer solid carrier is carbonization silicon ball, and a diameter of 4mm, described upper strata solid carrier is glass marble, a diameter of 4mm.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, is finally obtained
High-purity 3- NCO propyl-triethoxysilicane 80.3g, yield 67.0%, gas chromatographic detection purity 96.3%.
Embodiment four：
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes according to embodiment one,
Comprise the following steps：
The air-tightness of the synthesizer of the described high-purity 3- NCO propyl-triethoxysilicanes of step 1, inspection,
Fixed bed reactors are heated to 380 DEG C and keeping temperature, it is stand-by；
Step 2, regulation pressure-reducing valve will be passed through protective gas in fixed bed reactors, after being passed through protective gas 15min, use
Raw material [3- (triethoxy silicon substrate) propyl group] urethanes is passed through fixed bed reactors by measuring pump, carries out Pyrolysis
Should, reaction time 2h；
The reacted mixture of step 3, step 2 is cooled down by the first condenser, and the first described condenser uses 80 DEG C
Hot water cools down, and the mixture after cooling enters gas-liquid separator separates, and the liquid after separation enters product by cooler and connect
Closed cans, the gas after separation enter the second condenser, and the second described condenser is cooled down using 10 DEG C of cold water, the liquid after cooling
Ethanol receiving tank is entered, the gas after cooling is vented by gas flowmeter.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, in step 2
Described protective gas is nitrogen, and shield gas flow rate is air speed 6000h-1, the now flow 300L/h of nitrogen.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, in step 2
The addition of raw material [3- (triethoxy silicon substrate) propyl group] urethanes is 60g/h.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, under described
Layer solid carrier is carbonization silicon ball, and a diameter of 7mm, described upper strata solid carrier is glass marble, a diameter of 7mm.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, is finally obtained
High-purity 3- NCO propyl-triethoxysilicane 72.8g, yield 60.1%, gas chromatographic detection purity 95.6%.
Embodiment five：
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes according to embodiment one,
Comprise the following steps：
The air-tightness of the synthesizer of the described high-purity 3- NCO propyl-triethoxysilicanes of step 1, inspection,
Fixed bed reactors are heated to 400 DEG C and keeping temperature, it is stand-by；
Step 2, regulation pressure-reducing valve will be passed through protective gas in fixed bed reactors, after being passed through protective gas 15min, use
Raw material [3- (triethoxy silicon substrate) propyl group] urethanes is passed through fixed bed reactors by measuring pump, carries out Pyrolysis
Should, reaction time 2h；
The reacted mixture of step 3, step 2 is cooled down by the first condenser, and the first described condenser uses 80 DEG C
Hot water cools down, and the mixture after cooling enters gas-liquid separator separates, and the liquid after separation enters product by cooler and connect
Closed cans, the gas after separation enter the second condenser, and the second described condenser is cooled down using 10 DEG C of cold water, the liquid after cooling
Ethanol receiving tank is entered, the gas after cooling is vented by gas flowmeter.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, in step 2
Described protective gas is nitrogen, and shield gas flow rate is air speed 3000h-1, the now flow 150L/h of nitrogen.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, in step 2
The addition of raw material [3- (triethoxy silicon substrate) propyl group] urethanes is 60g/h.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, under described
Layer solid carrier is carbonization silicon ball, and a diameter of 7mm, described upper strata solid carrier is glass marble, a diameter of 7mm.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, is finally obtained
High-purity 3- NCO propyl-triethoxysilicane 87.5g, yield 72.9%, gas chromatographic detection purity 97.8%.
Embodiment six：
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes according to embodiment one,
Comprise the following steps：
The air-tightness of the synthesizer of the described high-purity 3- NCO propyl-triethoxysilicanes of step 1, inspection,
Fixed bed reactors are heated to 360 DEG C and keeping temperature, it is stand-by；
Step 2, regulation pressure-reducing valve will be passed through protective gas in fixed bed reactors, after being passed through protective gas 5min, use
Raw material [3- (triethoxy silicon substrate) propyl group] urethanes is passed through fixed bed reactors by measuring pump, carries out Pyrolysis
Should, reaction time 2h；
The reacted mixture of step 3, step 2 is cooled down by the first condenser, and the first described condenser uses 80 DEG C
Hot water cools down, and the mixture after cooling enters gas-liquid separator separates, and the liquid after separation enters product by cooler and connect
Closed cans, the gas after separation enter the second condenser, and the second described condenser is cooled down using 10 DEG C of cold water, the liquid after cooling
Ethanol receiving tank is entered, the gas after cooling is vented by gas flowmeter.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, in step 2
Described protective gas is nitrogen, and shield gas flow rate is air speed 3000h-1, the now flow 150L/h of nitrogen.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, in step 2
The addition of raw material [3- (triethoxy silicon substrate) propyl group] urethanes is 60g/h.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, under described
Layer solid carrier is carbonization silicon ball, and a diameter of 10mm, described upper strata solid carrier is glass marble, a diameter of 10mm.
The synthetic method of high-purity 3- NCO propyl-triethoxysilicanes described in present embodiment, is finally obtained
High-purity 3- NCO propyl-triethoxysilicane 93.3g, yield 77.8%, gas chromatographic detection purity 98.8%.
Claims (8)
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