CN102241701A - 一种γ-巯丙基三乙氧基硅烷的合成方法 - Google Patents
一种γ-巯丙基三乙氧基硅烷的合成方法 Download PDFInfo
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- CN102241701A CN102241701A CN2011101369274A CN201110136927A CN102241701A CN 102241701 A CN102241701 A CN 102241701A CN 2011101369274 A CN2011101369274 A CN 2011101369274A CN 201110136927 A CN201110136927 A CN 201110136927A CN 102241701 A CN102241701 A CN 102241701A
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- mercaptopropyltriethoxysilane
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- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title abstract description 18
- 230000002194 synthesizing effect Effects 0.000 title abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 claims abstract description 31
- 238000003756 stirring Methods 0.000 claims abstract description 21
- 238000004821 distillation Methods 0.000 claims abstract description 18
- 239000012071 phase Substances 0.000 claims abstract description 17
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 claims abstract description 14
- 230000007062 hydrolysis Effects 0.000 claims abstract description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 10
- 239000003112 inhibitor Substances 0.000 claims abstract description 8
- 239000012074 organic phase Substances 0.000 claims abstract description 7
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 claims abstract description 6
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims abstract description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 16
- 239000007789 gas Substances 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 14
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 238000010189 synthetic method Methods 0.000 claims description 11
- 230000003750 conditioning effect Effects 0.000 claims description 8
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 8
- 235000019800 disodium phosphate Nutrition 0.000 claims description 8
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 8
- 229940059574 pentaerithrityl Drugs 0.000 claims description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- 229910000397 disodium phosphate Inorganic materials 0.000 claims description 5
- 239000003039 volatile agent Substances 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 32
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 238000005516 engineering process Methods 0.000 description 8
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- 239000003444 phase transfer catalyst Substances 0.000 description 6
- 239000005060 rubber Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
- 238000003408 phase transfer catalysis Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
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- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
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- 238000005728 strengthening Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- DMYOHQBLOZMDLP-UHFFFAOYSA-N 1-[2-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl]-3-phenylpropan-1-one Chemical compound C1CCCCN1CC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 DMYOHQBLOZMDLP-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 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
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- MCEBKLYUUDGVMD-UHFFFAOYSA-N [SiH3]S(=O)=O Chemical compound [SiH3]S(=O)=O MCEBKLYUUDGVMD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 229920003020 cross-linked polyethylene Polymers 0.000 description 1
- 239000004703 cross-linked polyethylene Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 229920005558 epichlorohydrin rubber Polymers 0.000 description 1
- HCFPRFJJTHMING-UHFFFAOYSA-N ethane-1,2-diamine;hydron;chloride Chemical compound [Cl-].NCC[NH3+] HCFPRFJJTHMING-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011521 glass 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
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- 229920003023 plastic Polymers 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
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- 238000007789 sealing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
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- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
指标名称 | 实施例1 | 实施例2 | 实施例3 |
外观 | 无色透明液体 | 无色透明液体 | 无色透明液体 |
颜色( Pt-Co比色),号 | 10 | 10 | 10 |
密度 (20℃,g/cm3) | 0.9983 | 0.9998 | 1.0002 |
纯度(GC), % | 99.06 | 99.12 | 99.16 |
Claims (6)
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CN201110136927.4A CN102241701B (zh) | 2011-05-25 | 2011-05-25 | 一种γ-巯丙基三乙氧基硅烷的合成方法 |
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CN102241701A true CN102241701A (zh) | 2011-11-16 |
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102659831A (zh) * | 2012-04-25 | 2012-09-12 | 潍坊沃尔特化学有限公司 | 一种γ-巯丙基三甲氧基硅烷的合成方法 |
CN103408582A (zh) * | 2013-09-04 | 2013-11-27 | 荆州市江汉精细化工有限公司 | 一种3-巯丙基三乙氧基硅烷偶联剂的制备方法 |
CN104926857A (zh) * | 2015-06-25 | 2015-09-23 | 嘉兴学院 | 3-巯丙基三乙氧基硅烷的合成方法 |
CN107522730A (zh) * | 2017-08-31 | 2017-12-29 | 永修县艾科普新材料有限公司 | 一种γ‑巯丙基三乙氧基硅烷的制备方法 |
CN107936053A (zh) * | 2017-12-25 | 2018-04-20 | 荆州市江汉精细化工有限公司 | 一种巯丙基烷氧基硅烷的制备方法 |
CN110483566A (zh) * | 2019-07-31 | 2019-11-22 | 湖南正量工程技术有限公司 | 一种利用相转移催化剂制备巯基硅烷偶联剂的方法 |
CN111675735A (zh) * | 2020-07-28 | 2020-09-18 | 荆州市江汉精细化工有限公司 | 一种硫脲法制备巯基硅烷的方法 |
CN115215898A (zh) * | 2022-07-29 | 2022-10-21 | 上海橡实化学有限公司 | 一种生产巯丙基三乙氧基硅烷的方法 |
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CN101885734A (zh) * | 2010-06-26 | 2010-11-17 | 丁爱梅 | 一种双-[丙基三乙氧基硅烷]-四硫化物的合成方法 |
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2011
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Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102659831A (zh) * | 2012-04-25 | 2012-09-12 | 潍坊沃尔特化学有限公司 | 一种γ-巯丙基三甲氧基硅烷的合成方法 |
CN103408582A (zh) * | 2013-09-04 | 2013-11-27 | 荆州市江汉精细化工有限公司 | 一种3-巯丙基三乙氧基硅烷偶联剂的制备方法 |
CN103408582B (zh) * | 2013-09-04 | 2015-12-09 | 荆州市江汉精细化工有限公司 | 一种3-巯丙基三乙氧基硅烷偶联剂的制备方法 |
CN104926857A (zh) * | 2015-06-25 | 2015-09-23 | 嘉兴学院 | 3-巯丙基三乙氧基硅烷的合成方法 |
CN104926857B (zh) * | 2015-06-25 | 2017-10-31 | 嘉兴学院 | 3‑巯丙基三乙氧基硅烷的合成方法 |
CN107522730A (zh) * | 2017-08-31 | 2017-12-29 | 永修县艾科普新材料有限公司 | 一种γ‑巯丙基三乙氧基硅烷的制备方法 |
CN107936053A (zh) * | 2017-12-25 | 2018-04-20 | 荆州市江汉精细化工有限公司 | 一种巯丙基烷氧基硅烷的制备方法 |
CN110483566A (zh) * | 2019-07-31 | 2019-11-22 | 湖南正量工程技术有限公司 | 一种利用相转移催化剂制备巯基硅烷偶联剂的方法 |
CN110483566B (zh) * | 2019-07-31 | 2022-03-25 | 湖南正量工程技术有限公司 | 一种利用相转移催化剂制备巯基硅烷偶联剂的方法 |
CN111675735A (zh) * | 2020-07-28 | 2020-09-18 | 荆州市江汉精细化工有限公司 | 一种硫脲法制备巯基硅烷的方法 |
CN111675735B (zh) * | 2020-07-28 | 2023-08-29 | 湖北江瀚新材料股份有限公司 | 一种硫脲法制备巯基硅烷的方法 |
CN115215898A (zh) * | 2022-07-29 | 2022-10-21 | 上海橡实化学有限公司 | 一种生产巯丙基三乙氧基硅烷的方法 |
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