CN108586516B - Preparation method of carbamate alkoxy silane and isocyanate alkoxy silane - Google Patents
Preparation method of carbamate alkoxy silane and isocyanate alkoxy silane Download PDFInfo
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- alkoxy silane
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- 125000003545 alkoxy group Chemical group 0.000 title claims abstract description 34
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 229910000077 silane Inorganic materials 0.000 title claims abstract description 32
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000012948 isocyanate Substances 0.000 title abstract description 10
- 150000002513 isocyanates Chemical class 0.000 title abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 33
- -1 chloropropyl Chemical group 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical group COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 7
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 claims description 5
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- 230000008569 process Effects 0.000 abstract description 11
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 239000002994 raw material Substances 0.000 abstract description 9
- 239000007787 solid Substances 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 238000005336 cracking Methods 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 231100000252 nontoxic Toxicity 0.000 abstract description 4
- 230000003000 nontoxic effect Effects 0.000 abstract description 4
- 150000002894 organic compounds Chemical class 0.000 abstract description 3
- 230000002194 synthesizing effect Effects 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 238000005260 corrosion Methods 0.000 abstract description 2
- 230000007797 corrosion Effects 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 3
- 238000010907 mechanical stirring Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- AZDDBRPDIWQGEK-UHFFFAOYSA-N 3-chloropropyl-diethoxy-ethylsilane Chemical compound CCO[Si](CC)(OCC)CCCCl AZDDBRPDIWQGEK-UHFFFAOYSA-N 0.000 description 2
- KNTKCYKJRSMRMZ-UHFFFAOYSA-N 3-chloropropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCCl KNTKCYKJRSMRMZ-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 2
- 150000003377 silicon compounds Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- NOKSMMGULAYSTD-UHFFFAOYSA-N [SiH4].N=C=O Chemical compound [SiH4].N=C=O NOKSMMGULAYSTD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- XNRHTMDHGDWBGP-UHFFFAOYSA-N carbamic acid;hydrochloride Chemical compound Cl.NC(O)=O XNRHTMDHGDWBGP-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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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
- C07F7/12—Organo silicon halides
- C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
- C07F7/127—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions not affecting the linkages to the silicon atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
The application relates to a preparation method of carbamate alkoxy silane and a preparation method of isocyanate alkoxy silane. Specifically, according to the application, firstly, environment-friendly and non-toxic raw materials of carbamate and chloropropyl alkoxy silane are used for synthesizing carbamate alkoxy silane, and then the carbamate alkoxy silane is cracked under mild conditions to obtain isocyanate alkoxy silane. The method has the beneficial effects that the synthesis process route is simple, and the method belongs to a green and clean production mode. The raw material carbamate is a non-toxic organic compound, is easy to transport and store and has no leakage. The reaction condition is mild, and the reaction process has no corrosion to equipment and no pollution to the environment. No solid and other wastes are generated in the cracking process, and the operation is easy.
Description
Technical Field
The application relates to the technical field of organic compound synthesis, in particular to a preparation method of carbamate alkoxy silane and isocyanate alkoxy silane.
Background
The isocyanate group alkoxy silane is mainly used in silane sealant and modified polyurethane resin. In the traditional synthesis process of isocyanate, the phosgene method is used more frequently. It has been reported at home and abroad that the isocyanate is prepared by the reaction of amine compounds and phosgene. However, the phosgene method has complex technology, extremely toxic raw materials, and serious environmental pollution caused by a large amount of corrosive chemicals such as HCl, chlorine and the like. With the increasing environmental protection requirements, the development of non-phosgene methods is becoming a very important direction in the chemical field.
Chinese patent publication No. CN1631893A discloses a preparation method, which comprises using aminosilane and carbonate as raw materials, generating a mixture containing silicon-based organic carbamate under the action of an alkaline catalyst, neutralizing with acid, filtering, and finally performing reduced pressure rectification cracking on the filtrate at the temperature of 100-200 ℃ to obtain the isocyanato alkoxy silane.
Chinese patent publication No. CN 101161657a discloses another preparation method, which is to prepare an isocyanate silane coupling agent in an organic solvent under the action of a catalyst by using amino silane and carbonyl diimidazole as raw materials.
Chinese patent publication No. CN101307067A discloses a preparation method, which comprises using carbamate alkoxy silane as raw material, adjusting pH to 0-7, thermally cracking at 300-500 deg.C under normal pressure to obtain a mixture containing alcohol, carbamate alkoxy silane and isocyanate alkoxy silane, distilling under reduced pressure, and collecting the fraction to obtain isocyanate alkoxy silane.
Among the above synthetic methods, the first method generates solid salt waste, the second method uses expensive carbonyldiimidazole, and the third method has an excessively high cracking temperature. For this reason, there is still a need in the art to develop an environmentally friendly method for synthesizing isocyanatoalkoxysilanes with mild reaction conditions.
Disclosure of Invention
The present application aims to provide a method for preparing a carbamatoalkoxysilane and a method for preparing an isocyanatoalkoxysilane, thereby solving the above-mentioned problems of the prior art. Specifically, according to the application, firstly, environment-friendly and non-toxic raw materials of carbamate and chloropropyl alkoxy silane are used for synthesizing carbamate alkoxy silane, and then the carbamate alkoxy silane is cracked under mild conditions to obtain isocyanate alkoxy silane.
In order to achieve the above object, the present application provides the following technical solutions.
In a first aspect, the present application provides a process for the preparation of a carbamoylalkoxysilane, said process comprising reacting a carbamate with chloropropylalkoxysilane at a temperature of 90-150 ℃ for a predetermined time, and purifying to obtain a colorless or pale yellow clear liquid carbamoylalkoxysilane.
In one embodiment of the first aspect, the carbamate has a structure represented by the following general formula (I):
wherein R is1Is a saturated alkyl group with a carbon chain length of C1-C6。
In one embodiment of the first aspect, the chloropropylalkoxysilane has a structure represented by the following general formula (II):
CI-(CH2)3-SiX(3-a)R2 aa compound of the general formula (II),
wherein R is2Is a saturated alkyl radical having a carbon chain length of C1-C6(ii) a a is an integer of 0 to 3; x is a saturated alkoxy group with a carbon chain length of C1-C6。
In one embodiment of the first aspect, the carbamatoalkoxysilane has a structure represented by the following general formula (III):
wherein R is1Is a saturated alkyl group with a carbon chain length of C1-C6；R2Is a saturated alkyl radical having a carbon chain length of C1-C6(ii) a a is an integer of 0 to 3; x is a saturated alkoxy group with a carbon chain length of C1-C6。
In one embodiment of the first aspect, the carbamate is methyl carbamate or ethyl carbamate.
In one embodiment of the first aspect, the chloropropylalkoxysilane is one of chloropropyltrimethoxysilane, chloropropyltriethoxysilane, chloropropylmethyldimethoxysilane and chloropropylethyldiethoxysilane.
In one embodiment of the first aspect, the reaction of the carbamate with the chloropropylalkoxysilane is carried out in an anhydrous or low moisture (moisture mass content less than 0.1%) environment.
In one embodiment of the first aspect, the chloropropylalkoxysilane is added dropwise via a constant pressure dropping funnel.
In one embodiment of the first aspect, the molar ratio of carbamate to chloropropylalkoxysilane is from 1:10 to 10: 1.
In a second aspect, the present application provides a method for preparing an isocyanatoalkoxysilane, which comprises subjecting a carbamatoalkoxysilane prepared by the method for preparing a carbamatoalkoxysilane according to the first aspect to reduced pressure distillation at a temperature of 100 ℃ to 200 ℃ in the presence of a catalyst to obtain an isocyanatoalkoxysilane.
In one embodiment of the second aspect, the vacuum during the reduced pressure distillation is from 0 to 100 mmHg.
In one embodiment of the second aspect, the catalyst used in the reduced pressure distillation is one of a metal or metal oxide, an organic sulfonate or a silicon compound.
In one embodiment of the second aspect, the metal catalyst comprises iron powder, zinc powder, or tin powder.
Compared with the prior art, the method has the beneficial effects that the process route is simple, and the method belongs to a green clean production mode. The raw material carbamate is a non-toxic organic compound, is easy to transport and store and has no leakage. The reaction condition is mild, and the reaction process has no corrosion to equipment and no pollution to the environment. No solid and other wastes are generated in the cracking process, and the operation is easy.
Drawings
FIG. 1 shows an infrared spectrum of isocyanatopropyltrimethoxysilane according to example 1.
FIG. 2 shows an infrared spectrum of isocyanatopropyltriethoxysilane according to example 2.
Detailed Description
Unless otherwise indicated, implied from the context, or customary in the art, all parts and percentages herein are by weight and the testing and characterization methods used are synchronized with the filing date of the present application. Where applicable, the contents of any patent, patent application, or publication referred to in this application are incorporated herein by reference in their entirety and their equivalent family patents are also incorporated by reference, especially as they disclose definitions relating to synthetic techniques, products and process designs, polymers, comonomers, initiators or catalysts, and the like, in the art. To the extent that a definition of a particular term disclosed in the prior art is inconsistent with any definitions provided herein, the definition of the term provided herein controls.
The numerical ranges in this application are approximations, and thus may include values outside of the ranges unless otherwise specified. A numerical range includes all numbers from the lower value to the upper value, in increments of 1 unit, provided that there is a separation of at least 2 units between any lower value and any higher value. For example, if a compositional, physical, or other property (e.g., molecular weight, melt index, etc.) is recited as 100 to 1000, it is intended that all individual values, e.g., 100, 101,102, etc., and all subranges, e.g., 100 to 166,155 to 170,198 to 200, etc., are explicitly recited. For ranges containing a numerical value less than 1 or containing a fraction greater than 1 (e.g., 1.1, 1.5, etc.), then 1 unit is considered appropriate to be 0.0001, 0.001, 0.01, or 0.1. For ranges containing single digit numbers less than 10 (e.g., 1 to 5), 1 unit is typically considered 0.1. these are merely specific examples of what is intended to be expressed and all possible combinations of numerical values between the lowest value and the highest value enumerated are to be considered to be expressly stated in this application.
When used with respect to chemical compounds, the singular includes all isomeric forms and vice versa (e.g., "hexane" includes all isomers of hexane, individually or collectively) unless expressly specified otherwise. In addition, unless explicitly stated otherwise, the use of the terms "a", "an" or "the" are intended to include the plural forms thereof.
The terms "comprising," "including," "having," and derivatives thereof do not exclude the presence of any other component, step or procedure, and are not intended to exclude the presence of other elements, steps or procedures not expressly disclosed herein. To the extent that any doubt is eliminated, all compositions herein containing, including, or having the term "comprise" may contain any additional additive, adjuvant, or compound, unless expressly stated otherwise. Rather, the term "consisting essentially of … …" excludes any other components, steps or processes from the scope of any of the terms hereinafter recited, except those necessary for performance. The term "consisting of … …" does not include any components, steps or processes not specifically described or listed. Unless explicitly stated otherwise, the term "or" refers to the listed individual members or any combination thereof.
In one embodiment, the present invention provides a novel process for the synthesis of isocyanatoalkoxysilanes. The method does not pollute the environment, and belongs to a clean production method.
The main principle of the method of the invention is as follows:
the method mainly comprises two steps: (a) taking carbamate and chloropropyl alkoxy silane as raw materials, reacting at a certain temperature to obtain a mixture of carbamate alkoxy silane and carbamate hydrochloride, and filtering salt to obtain colorless or light yellow clear liquid carbamate alkoxy silane. (b) And (3) carrying out reduced pressure rectification on the clear liquid under the action of a catalyst to obtain the product isocyanate group alkoxy silane.
The reaction equation is as follows:
in the above formula (a) (b): r1Is a saturated alkyl group with a carbon chain length of C1-C6；R2Is a saturated alkyl radical having a carbon chain length of C1-C6(ii) a a is an integer of 0 to 3; x is a saturated alkoxy group with a carbon chain length of C1-C6。
The carbamate in the step (a) is one of methyl carbamate and ethyl carbamate.
The chloropropyl alkoxysilane in the step (a) is one of chloropropyl trimethoxysilane, chloropropyl triethoxysilane, chloropropyl methyldimethoxysilane and chloropropyl ethyldiethoxysilane.
In the step (a), the chloropropyl alkoxysilane is easy to hydrolyze in water, so that the reaction of the carbamate and the chloropropyl alkoxysilane needs to be kept in an anhydrous or low-moisture environment (less than or equal to 0.1%).
And (b) dropwise adding the chloropropyl alkoxy silane in the step (a) by using a constant-pressure dropping funnel, wherein the dropwise adding time is 1-3 h.
The molar ratio of the carbamate to the chloropropylalkoxysilane in the step (a) is 1:10-10: 1. The reaction temperature is 90-150 ℃, and the reaction time is 1-10 h.
The reduced pressure distillation conditions in the step (b) are as follows: the temperature is 100 ℃ and 200 ℃, and the vacuum degree is 0-100 mmHg.
The catalyst used in the reduced pressure distillation in the step (b) is one of metal or metal oxide (iron powder, zinc powder and tin), organic sulfonate or silicon compounds.
Examples
The present invention will be further described with reference to the following examples
Example 1
75g of methyl carbamate is weighed and added into a four-neck flask with a thermometer, a condenser, a constant-pressure low-liquid funnel and mechanical stirring, and the mixture is heated to 60 ℃ for melting. And introducing inert gas at the temperature, and dropwise adding 198g of chloropropyltrimethoxysilane for about 2 hours. After the dropwise addition, the temperature is raised to 120 ℃ and the temperature is kept for 3 hours. And (3) reducing the temperature, controlling the stirring speed, removing solid salt in the obtained mixture by filtration to obtain clear filtrate, and performing rectification under reduced pressure by using iron powder as a catalyst to collect 155g of 120 ℃/20mmHg fraction. By infrared spectroscopic analysis, as shown in FIG. 1, a strong and sharp absorption peak at 2210-2276cm-1 was observed, indicating that isocyanatopropyltrimethoxysilane was synthesized.
Example 2
150g of methyl carbamate was weighed, charged into a four-neck flask equipped with a thermometer, a condenser, a constant pressure low liquid funnel and mechanical stirring, and heated to 60 ℃ for melting. At the temperature, inert gas is introduced, and 99g of chloropropyltriethoxysilane is added dropwise for about 1.5 h. After the dropwise addition, the temperature is raised to 120 ℃ and the temperature is kept for 3 hours. And (3) reducing the temperature and controlling the stirring speed, removing solid salt in the obtained mixture by filtration to obtain clear filtrate, and performing reduced pressure rectification by using zinc powder as a catalyst to collect 70g of 130 ℃/20mmHg fraction. By infrared spectroscopic analysis, as shown in FIG. 2, a strong and sharp absorption peak at 2210-2276cm-1 was observed, indicating that isocyanatopropyltriethoxysilane was synthesized.
Example 3
30g of ethyl carbamate is weighed and added into a four-neck flask with a thermometer, a condenser, a constant-pressure low-liquid funnel and mechanical stirring, and the mixture is heated to 60 ℃ for melting. Introducing inert gas at the temperature, and dropwise adding 162g of chloropropyltrimethoxysilane for about 2 h. After the dropwise addition, the temperature is raised to 120 ℃ and the temperature is kept for 3 hours. And (3) reducing the temperature, controlling the stirring speed, removing solid salt in the obtained mixture by filtration to obtain clear filtrate, and performing reduced pressure rectification by using iron powder as a catalyst to collect 140g of 120 ℃/20mmHg fraction. By infrared spectroscopic analysis, a strong and sharp absorption peak was observed at 2210-2276cm-1, similarly to example 1, indicating the synthesis of isocyanatopropyltrimethoxysilane.
The embodiments described above are intended to facilitate the understanding and appreciation of the application by those skilled in the art. It will be readily apparent to those skilled in the art that various modifications to these embodiments may be made, and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present application is not limited to the embodiments herein, and those skilled in the art who have the benefit of this disclosure will appreciate that many modifications and variations are possible within the scope of the present application without departing from the scope and spirit of the present application.
Claims (3)
1. A preparation method of carbamate alkoxy silane comprises the steps of reacting carbamate with chloropropyl alkoxy silane in a low-moisture environment for a preset time at the temperature of 90-150 ℃, and purifying to obtain colorless or light yellow clear liquid carbamate alkoxy silane; wherein the carbamate is methyl carbamate or ethyl carbamate; the chloropropyl alkoxy silane is one of chloropropyl trimethoxy silane or chloropropyl triethoxy silane, and the low-moisture environment is an environment with the moisture mass content of less than 0.1%.
2. The method of preparing carbamatoalkoxysilane according to claim 1, wherein chloropropylalkoxysilane is added dropwise via a constant pressure dropping funnel.
3. The process for preparing carbamatoalkoxysilane according to claim 1 wherein the molar ratio of carbamate to chloropropylalkoxysilane is from 1:10 to 10: 1.
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|---|---|---|---|---|
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| CN1483038A (en) * | 2000-12-21 | 2004-03-17 | 电化学工业有限公司（国际） | Method for producing isocyanato-organosilanes |
| CN1631893A (en) * | 2003-12-22 | 2005-06-29 | 张家港市国泰华荣化工新材料有限公司 | Process for preparing silicane containing isocyanate group |
| CN1839140A (en) * | 2003-12-11 | 2006-09-27 | 电化学工业有限公司（国际） | Method for producing isocyanate-organosilanes |
| WO2009003956A2 (en) * | 2007-06-29 | 2009-01-08 | Rhodia Operations | Method of preparing hydrazo-silane compounds by nucleophilic substitution reaction |
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2018
- 2018-06-06 CN CN201810587039.6A patent/CN108586516B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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