CN100334096C - 有机官能硅烷的制备方法 - Google Patents
有机官能硅烷的制备方法 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic 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
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
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Abstract
可通过使相应的单烯基二氯硅烷，即烯丙基二氯硅烷与一种一元醇，即甲醇反应，制备烯基烷氧基硅烷，例如烯丙基三甲氧基硅烷。不需要催化剂，且这些反应可在室温下完成。
Description
本发明涉及通过烷氧基化作用、特别是甲氧基化作用，来制备某些有机官能硅烷的方法，
有机官能硅烷可用于许多应用领域，包括用作还原剂、甲硅烷化剂、防水剂、偶联剂、交联剂以及作为制备不同稠度的聚硅氧烷的单体。因此，一直需要更有效的制备它们的方法，和一直需要制备这些硅烷的更简单且更廉价的方法。
虽然现有技术包括通过三氯硅烷的烷氧基化制备硅烷的已知方法，例如美国专利2,927,938(1960年3月8日)，但是在公用领域，没有涉及通过不饱和二氯硅烷的烷氧基化制备含不饱和基团的有机官能硅烷的方法。典型的，通过Grignard反应制备这种烯基官能的烷氧基硅烷，所述Grignard反应涉及烯丙基氯与镁和四烷氧基硅烷例如四甲氧基硅烷和四乙氧基硅烷反应，这些内容例如在美国专利3,403,050(1968年9月24日)中描述。
本发明涉及通过使单烯基二氯硅烷与一元醇反应形成烯基烷氧基硅烷，来制备有机官能硅烷的方法。
在反应组分当中，最优选单烯基二氯硅烷例如烯丙基二氯硅烷，和一元醇例如甲醇。由此，将获得烯丙基三甲氧基硅烷。
通过以下详细描述，将使本发明的这些和其它特征变得显而易见。
发明详述
本发明的方法涉及，通过使单烯基二氯硅烷与一元醇反应，来制备有机官能硅烷，例如烯基烷氧基硅烷。该方法可以用下式表示：
在上式中，R1表示氢或具有1-6个碳原子的烷基，例如甲基、乙基、丙基、异丙基、丁基、异丁基、戊基和己基，或者R1可以是环烷基，例如环丁基、环戊基和环己基；R2代表氢；R3代表含1-6个碳原子的烷基，例如甲基、乙基、丙基、异丙基、丁基、异丁基、戊基和己基，环烷基，例如环丁基、环戊基和环己基，或者烯丙基；x为0-4；y为3。
合适的单烯基二氯硅烷的一些代表性实例包括：乙烯基二氯硅烷CH2＝CHSiHCl2，烯丙基二氯硅烷CH2＝CHCH2SiHCl2，2-丁烯基二氯硅烷CH3CH＝CHCH2SiHCl2，3-丁烯基二氯硅烷CH2＝CHCH2CH2SiHCl2和5-己烯基二氯硅烷CH2＝CH(CH2)4SiHCl2。
可采用的一元醇的一些代表性实例包括：甲醇、乙醇、丙醇、异丙醇、环丁醇、环戊醇、环己醇和烯丙醇。
这些组分能产生烯基烷氧基硅烷，例如乙烯基三甲氧基硅烷、乙烯基三乙基硅烷、乙烯基三丙氧基硅烷、乙烯基三丁氧基硅烷、乙烯基三戊氧基硅烷、乙烯基三己氧基硅烷、烯丙基三甲氧基硅烷、烯丙基三乙氧基硅烷、烯丙基三丙氧基硅烷、烯丙基三丁氧基硅烷、烯丙基三戊氧基硅烷、烯丙基三己氧基硅烷、2-丁烯基三甲氧基硅烷、2-丁烯基三乙氧基硅烷、2-丁烯基三丙氧基硅烷、2-丁烯基三丁氧基硅烷、2-丁烯基三戊氧基硅烷、2-丁烯基三己氧基硅烷、5-己烯基三甲氧基硅烷、5-己烯基三乙氧基硅烷、5-己烯基三丙氧基硅烷、5-己烯基三丁氧基硅烷、5-己烯基三戊氧基硅烷和5-己烯基三己氧基硅烷。
取决于使用的醇，可制备另外一些烯基烷氧基硅烷，包括：烯丙基三环丁氧基硅烷、烯丙基三环戊氧基硅烷、烯丙基环己烯氧基硅烷、烯丙基三烯丙氧基(trialloxy)硅烷、3-丁烯基三丁氧基硅烷、3-丁烯基三戊氧基硅烷、3-丁烯基三己氧基硅烷、3-丁烯基三丁氧基硅烷、3-丁烯基三戊氧基硅烷、3-丁烯基三己氧基硅烷、3-丁烯基三烯丙氧基硅烷、2-丁烯基三丁氧基硅烷、2-丁烯基三戊氧基硅烷、2-丁烯基三己氧基硅烷、2-丁烯基三烯丙氧基硅烷、5-己烯基三环丁氧基硅烷、5-己烯基三环戊氧基硅烷、5-己烯基三环己烯氧基硅烷和5-己烯基三烯丙氧基硅烷。
因此，在本发明优选实施方案的一个具体方案中，使烯丙基二氯硅烷与甲醇反应，产生烯丙基三甲氧基硅烷、氯化氢和氢，如下式所示：
起始单体烯丙基二氯硅烷可商购，或可例如按美国专利5,338,876(1994年8月16)中所述，按下式，通过使元素硅同时与烯丙基氯和盐酸反应而制备：
本发明使用的单烯基二氯硅烷和一元醇的相对量可以变化。尽管不要求反应在化学计量条件下进行，但优选使用化学计量过量的一元醇进行反应。因此，最优选，使用约0.1-10％化学计量过量的一元醇进行反应。此反应不需要催化剂，且虽然可以间歇、半连续或连续方式进行此方法，但最优选间歇法。
在-80-350℃，优选在20-250℃，最优选在约室温(即20-25℃/68-77)下，使单烯基二氯硅烷和一元醇接触。
最佳反应时间可根据反应物、反应温度以及单烯基二氯硅烷和一元醇的浓度改变。通常，反应物的接触时间延长超过约24小时是没有益处的，但通常同样也没有害处，除非采用极低的温度。对于本文所使用的具体反应物而言，可在约4个小时内获得实用的产率。
反应可以在常压、低于常压或高于常压下进行。此外，基于反应物的性能和可用设备，合理地选择反应条件。非挥发性反应物尤其适合于在有或没有回流装置的情况下、于常压下加热。常温下是气态的反应物优选在自生或诱导压力下、以基本恒定的体积进行反应。通过将所有反应物保留在液相中，将获得最好的结果。
提出以下实施例以便更详细地说明本发明。
在本实施例中使用的设备由安放在加热罩上的100mL三颈圆底烧瓶、具有磁搅拌棒的支架(jack)、加料漏斗、回流冷凝器、温度计和氮引入系统组成。
将12.6克/0.9摩尔的烯丙基二氯硅烷装入烧瓶中。向加料漏斗中装入8.57克/0.26摩尔的甲醇。然后在室温下，将甲醇滴加到装在烧瓶里的烯丙基二氯硅烷中。完成向烧瓶滴加甲醇需要约20分钟。可观察到反应轻微放热。产生氯化氢并通过鼓入氮气从烧瓶中将其除去。使用气相色谱(GC)分析反应混合物，分析结果显示：它含有约40％GC面积的烯丙基三甲氧基硅烷，其余为未反应的甲醇和3-甲氧基丙基三甲氧基硅烷CH3O(CH2)3Si(OCH3)3。经气相色谱/质谱分析(GC/MS)确认反应混合物中存在烯丙基三甲氧基硅烷。
在不背离本发明基本特征的前提下，可对本申请所描述的化合物、组合物和方法作出其它改变。本申请中具体说明的实施方案只是示范、例性的，无意用其限定本发明的范围，本发明的范围由所附权利要求书限定。
Claims (3)
1.一种制备有机官能硅烷的方法，包括在没有催化剂的情况下仅使单烯基二氯硅烷与具有1-6个碳原子的一元醇反应，生成烯基三烷氧基硅烷。
2.根据权利要求1的方法，其中所述单烯基二氯硅烷选自乙烯基二氯硅烷、烯丙基二氯硅烷、2-丁烯基二氯硅烷、3-丁烯基二氯硅烷和5-己烯基二氯硅烷。
3.根据权利要求1的方法，其中所述烯基三烷氧基硅烷选自乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、乙烯基三丙氧基硅烷、乙烯基三丁氧基硅烷、乙烯基三戊氧基硅烷、乙烯基三己氧基硅烷、烯丙基三甲氧基硅烷、烯丙基三乙氧基硅烷、烯丙基三丙氧基硅烷、烯丙基三丁氧基硅烷、烯丙基三戊氧基硅烷、烯丙基三己氧基硅烷、2-丁烯基三甲氧基硅烷、2-丁烯基三乙氧基硅烷、2-丁烯基三丙氧基硅烷、2-丁烯基三丁氧基硅烷、2-丁烯基三戊氧基硅烷、2-丁烯基三己氧基硅烷、5-己烯基三甲氧基硅烷、5-己烯基三乙氧基硅烷、5-己烯基三丙氧基硅烷、5-己烯基三丁氧基硅烷、5-己烯基三戊氧基硅烷、5-己烯基三己氧基硅烷、烯丙基三环丁氧基硅烷、烯丙基三环戊氧基硅烷、烯丙基环己烯氧基硅烷、烯丙基三烯丙氧基硅烷、3-丁烯基三丁氧基硅烷、3-丁烯基三戊氧基硅烷、3-丁烯基三己氧基硅烷、3-丁烯基三烯丙氧基硅烷、2-丁烯基三丁氧基硅烷、2-丁烯基三戊氧基硅烷、2-丁烯基三己氧基硅烷、2-丁烯基三烯丙氧基硅烷、5-己烯基三环丁氧基硅烷、5-己烯基三环戊氧基硅烷、5-己烯基三环己烯氧基硅烷和5-己烯基三烯丙氧基硅烷。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/269,241 US6878839B2 (en) | 2002-10-11 | 2002-10-11 | Method for preparing organofunctional silanes |
| US10/269,241 | 2002-10-11 |
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| Publication Number | Publication Date |
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| CN1684969A CN1684969A (zh) | 2005-10-19 |
| CN100334096C true CN100334096C (zh) | 2007-08-29 |
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| CNB038233045A Expired - Fee Related CN100334096C (zh) | 2002-10-11 | 2003-09-05 | 有机官能硅烷的制备方法 |
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| Country | Link |
|---|---|
| US (1) | US6878839B2 (zh) |
| EP (1) | EP1549657B1 (zh) |
| JP (1) | JP2006502222A (zh) |
| KR (1) | KR20050062774A (zh) |
| CN (1) | CN100334096C (zh) |
| AT (1) | ATE331724T1 (zh) |
| AU (1) | AU2003265945A1 (zh) |
| DE (1) | DE60306536T2 (zh) |
| TW (1) | TW200405895A (zh) |
| WO (1) | WO2004033469A1 (zh) |
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| BR0312883A (pt) * | 2002-07-23 | 2005-06-14 | Ppg Ind Ohio Inc | Composição de encolagem para fibras de vidro, cordão de fibras de vidro e composto de poliolefinas |
| JP2019504214A (ja) * | 2015-12-30 | 2019-02-14 | マックステリアル・インコーポレイテッドＭａｘｔｅｒｉａｌ， Ｉｎｃ． | 選択された表面特徴及び形状を有するコーティング及びコーティングが施された表面 |
| FR3084367B1 (fr) | 2018-07-27 | 2020-09-18 | Bostik Sa | Procede de preparation de composes a groupement alkoxysilyl |
| CN112745345B (zh) * | 2020-12-30 | 2022-09-27 | 江西晨光新材料股份有限公司 | 一种环氧基硅烷偶联剂的制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4268682A (en) * | 1975-09-05 | 1981-05-19 | Exxon Research & Engineering Co. | ω-Alkenyl silanes and αω-silyl alkanes |
| CN1107852A (zh) * | 1994-12-29 | 1995-09-06 | 曲阜市第三化工厂 | 中性乙烯基三乙氧基硅烷的制备方法 |
| CN1320600A (zh) * | 2000-04-21 | 2001-11-07 | 江苏日出(集团)公司 | 乙烯基三甲氧基硅烷的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2927938A (en) | 1956-11-02 | 1960-03-08 | Thiokol Chemical Corp | Preparation of chlorofluorosilanes by the selective fluorination of chloro-alkoxysilanes with boron trifluoride |
| US3403050A (en) | 1964-12-28 | 1968-09-24 | Stauffer Chemical Co | Water repellent compositions for porous substrates |
| US4173576A (en) * | 1975-07-23 | 1979-11-06 | Dynamit Nobel Aktiengesellschaft | Process for the esterification of chlorosilanes |
| DE3236628C2 (de) * | 1982-10-04 | 1986-09-11 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur kontinuierlichen Herstellung von Alkoxysilanen |
| KR950002860B1 (ko) | 1992-06-13 | 1995-03-27 | 한국과학기술연구원 | 클로로알켄닐실란들과그제조방법 |
-
2002
- 2002-10-11 US US10/269,241 patent/US6878839B2/en not_active Expired - Fee Related
-
2003
- 2003-09-05 EP EP03808083A patent/EP1549657B1/en not_active Expired - Lifetime
- 2003-09-05 AT AT03808083T patent/ATE331724T1/de not_active IP Right Cessation
- 2003-09-05 WO PCT/US2003/027864 patent/WO2004033469A1/en active IP Right Grant
- 2003-09-05 AU AU2003265945A patent/AU2003265945A1/en not_active Abandoned
- 2003-09-05 DE DE60306536T patent/DE60306536T2/de not_active Expired - Lifetime
- 2003-09-05 CN CNB038233045A patent/CN100334096C/zh not_active Expired - Fee Related
- 2003-09-05 JP JP2004543272A patent/JP2006502222A/ja not_active Ceased
- 2003-09-05 KR KR1020057006155A patent/KR20050062774A/ko not_active Application Discontinuation
- 2003-09-17 TW TW092125639A patent/TW200405895A/zh unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4268682A (en) * | 1975-09-05 | 1981-05-19 | Exxon Research & Engineering Co. | ω-Alkenyl silanes and αω-silyl alkanes |
| CN1107852A (zh) * | 1994-12-29 | 1995-09-06 | 曲阜市第三化工厂 | 中性乙烯基三乙氧基硅烷的制备方法 |
| CN1320600A (zh) * | 2000-04-21 | 2001-11-07 | 江苏日出(集团)公司 | 乙烯基三甲氧基硅烷的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1549657A1 (en) | 2005-07-06 |
| EP1549657B1 (en) | 2006-06-28 |
| AU2003265945A1 (en) | 2004-05-04 |
| KR20050062774A (ko) | 2005-06-27 |
| ATE331724T1 (de) | 2006-07-15 |
| US6878839B2 (en) | 2005-04-12 |
| US20040073053A1 (en) | 2004-04-15 |
| DE60306536D1 (de) | 2006-08-10 |
| JP2006502222A (ja) | 2006-01-19 |
| TW200405895A (en) | 2004-04-16 |
| CN1684969A (zh) | 2005-10-19 |
| DE60306536T2 (de) | 2007-06-21 |
| WO2004033469A1 (en) | 2004-04-22 |
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