CN108033976A - 一种以茂金属为催化剂的不饱和化合物硅氢加成反应 - Google Patents
一种以茂金属为催化剂的不饱和化合物硅氢加成反应 Download PDFInfo
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Abstract
本发明公开了一种以茂金属为催化剂的不饱和化合物硅氢加成反应,所述催化剂由一种茂金属配合物和一种金属粉末组成,所述茂金属配合物与金属粉末摩尔比为1:1~1:3,茂金属配合物为二氯二茂钛或二氯二茂锆,金属粉末为钐、镁、铝或锌中的任意一种。本发明制备的催化剂是非贵金属催化剂,具有成本低、操作简单等特点,同时也为硅氢加成反应催化剂增加了一个新品种,且所述催化剂针对不饱和烯烃的硅氢加成反应具有很好的催化效果,可以催化烯烃及酮类与多种含氢硅烷的加成反应,适用性广泛。
Description
技术领域
本发明涉及有机硅化学领域中的催化剂,尤其是涉及一种以茂金属为催化剂的不饱和化合物硅氢加成反应。
背景技术
催化硅氢加成反应在合成有机化学中占有重要的地位,是合成有机硅偶联剂和功能有机硅化合物及聚合物最重要的途径之一。通常直接使用铂、铑、铱等贵金属配合物作为硅氢加成反应的催化剂 (Ohtat T, Ito M, Tsuneto A ,J. Chem. Soc., Chem.Commun., 1994, 2525; Peng J, Bai Y, Li J, Lai G,Current Org. Chem.,2011, 15(16), 2802),虽然它们的催化活性比较好,但是这类催化体系昂贵的价格导致其工业应用受到限制,多数催化体系仅停留在研究层面。近年来,一些成本低廉,低毒,环保,制备简单,同时比较稳定的催化体系得到广泛关注。
发明内容
本发明是为了克服现有硅氢加成反应催化剂由于价格昂贵而使其工业应用受到限制的缺点,提供一种以茂金属为催化剂的不饱和化合物硅氢加成反应,该催化剂使用时反应条件温和,安全,有效。
为了实现上述目的,本发明采用以下技术方案:
一种以茂金属为催化剂的不饱和化合物硅氢加成反应,所述茂金属催化剂由一种茂金属配合物和一种金属粉末组成。金属粉末为具有还原能力的金属,其和茂金属配合物在反应条件下反应,得到低价态的钛或锆金属配合物作为催化中心。该催化剂体系在储存条件下可以长期保持稳定,避免了目前常用的贵金属催化剂需要预先制备且不易保存等缺点。
作为优选,茂金属配合物与金属粉末摩尔比为1:1~1:3。金属粉末用量过低,茂金属配合物前体还原不充分,降低催化活性;茂金属配合物与金属粉末摩尔比超过1:3,对提高催化活性作用不大,却增加产物分离难度。
作为优选,所述茂金属配合物为二氯二茂钛或二氯二茂锆。
作为优选,所述金属粉末为钐、镁、铝、锌、铁、钴或镍中的任意一种,优化条件下,选择钐、镁、铝、锌中的一种,其催化效果及保存性能优于其他金属粉末。
作为优选,茂金属配合物与金属粉末摩尔比为1:2。
作为优选,不所述饱和化合物为烯烃或酮类化合物。
作为优选,所述茂金属催化剂应用于不饱和化合物硅氢加成反应,其温度条件为80~100℃。在室温到100℃范围内,提高反应温度有利于提高烯烃或酮的转化率,进一步提高温度对转化率影响不大,但增加副反应,导致收率降低。优选为90℃。
因此,本发明具有如下有益效果:(1)催化剂是非贵金属催化剂,具有成本低、操作简单等特点;(2)为硅氢加成反应催化剂增加了一个新品种;(3)可以催化烯烃、酮类化合物和多种含氢硅烷的加成反应,适用性广泛。
具体实施方式
下面结合具体实施方式对本发明的技术方案做进一步的详细描述,如果无特殊说明,本发明的实施例中所采用的原料均为本领域常用的原料,实施例中所采用的方法,均为本领域的常规方法。硅氢加成反应后,采用气质联用仪和气相色谱仪进行分析检测不饱和化合物转化率和加成产物选择性。
实施例1:
一种应用茂金属催化剂催化不饱和化合物的硅氢加成反应:将二氯二茂钛(0.50 g,0.002 mol),金属钐粉(0.60 g,0.004 mol),己烯(3.36g,0.04 mol),Ph2SiH2(8.84 g,0.048 mol)加入25 mL烧瓶中,90℃下搅拌12 h,反应完成后,GC测得烯烃转化率为94.6%,β-加成产物选择性为98.5%。
实施例2:
一种应用茂金属催化剂催化不饱和化合物的硅氢加成反应:将二氯二茂钛(0.50 g,0.002 mol),金属钐粉(0.60 g,0.004 mol),辛烯 (4.48g,0.04 mol),Ph2SiH2(8.84 g,0.048 mol)加入25 mL烧瓶中,90℃下搅拌12 h,反应完成后,GC测得烯烃转化率为92.8%,β-加成产物选择性为99.2%。
实施例3:
一种应用茂金属催化剂催化不饱和化合物的硅氢加成反应:将二氯二茂钛(0.50 g,0.002 mol),金属钐粉(0.60 g,0.004mol),苯乙酮(12.0 g,0.10 mol),Ph2SiH2(22.1 g,0.12 mol)加入50mL烧瓶中,90℃下搅拌6 h,反应完成后,GC测得苯乙酮转化率为98.6%。
实施例4:
一种应用茂金属催化剂催化不饱和化合物的硅氢加成反应:将二氯二茂钛(0.50 g,0.002 mol),金属钐粉(0.60 g,0.004 mol),苯乙酮(12.0 g,0.10 mol),(EtO)3SiH (19.7g,0.12 mol)加入50mL烧瓶中,90℃下搅拌6 h,反应完成后,GC测得苯乙酮转化率为98.5%。
实施例5:
一种应用茂金属催化剂催化不饱和化合物的硅氢加成反应:将二氯二茂钛(0.50 g,0.002 mol),金属镁粉(0.096 g,0.004 mol),己烯(3.36g,0.04 mol),Ph2SiH2(8.84 g,0.048 mol)加入25 mL烧瓶中,90℃下搅拌12 h,反应完成后,GC测得烯烃转化率为74.6%,β-加成产物选择性为97.5%。
实施例6:
一种应用茂金属催化剂催化不饱和化合物的硅氢加成反应:将二氯二茂钛(0.50 g,0.002 mol),金属镁粉(0.048 g,0.002mol),辛烯 (4.48g,0.04 mol),Ph2SiH2(8.84 g,0.048 mol)加入25 mL烧瓶中,90℃下搅拌12 h,反应完成后,GC测得烯烃转化率为56.8%,β-加成产物选择性为98.2%。
实施例7:
一种应用茂金属催化剂催化不饱和化合物的硅氢加成反应:将二氯二茂钛(0.50 g,0.002 mol),金属锌粉(0.26 g,0.004 mol),辛烯 (4.48g,0.04 mol),Ph2SiH2(8.84 g,0.048 mol)加入25 mL烧瓶中,90℃下搅拌12 h,反应完成后,GC测得烯烃转化率为76.8%,β-加成产物选择性为97.1%。
实施例8:
一种应用茂金属催化剂催化不饱和化合物的硅氢加成反应:将二氯二茂钛(0.50 g,0.002 mol),金属铝粉(0.108 g,0.004 mol),辛烯 (4.48g,0.04 mol),Ph2SiH2(8.84 g,0.048 mol)加入25 mL烧瓶中,90℃下搅拌12 h,反应完成后,GC测得烯烃转化率为86.5%,β-加成产物选择性为97.3%。
实施例9:
一种应用茂金属催化剂催化不饱和化合物的硅氢加成反应:将二氯二茂钛(0.50 g,0.002 mol),金属钐粉(0.30 g,0.002 mol),辛烯 (4.48g,0.04 mol),Ph2SiH2(8.84 g,0.048 mol)加入25 mL烧瓶中,90℃下搅拌12 h,反应完成后,GC测得烯烃转化率为58.9%,β-加成产物选择性为98.5%。
实施例10:
一种应用茂金属催化剂催化不饱和化合物的硅氢加成反应:将二氯二茂钛(0.50 g,0.002 mol),金属钐粉(0.90 g,0.006 mol),辛烯 (4.48g,0.04 mol),Ph2SiH2(8.84 g,0.048 mol)加入25 mL烧瓶中,90℃下搅拌12 h,反应完成后,GC测得烯烃转化率为88.7%,β-加成产物选择性为98.8%。
实施例11:
一种应用茂金属催化剂催化不饱和化合物的硅氢加成反应:将二氯二茂钛(0.50 g,0.002 mol),金属钐粉(0.60 g,0.004 mol),正十二烯 (6.72g,0.04 mol),Ph2SiH2(8.84g,0.048 mol)加入25 mL烧瓶中,90℃下搅拌12 h,反应完成后,GC测得烯烃转化率为84.4%,β-加成产物选择性为97.9%。
实施例12:
一种应用茂金属催化剂催化不饱和化合物的硅氢加成反应:将二氯二茂锆(0.585 g,0.002 mol),金属钐粉(0.60 g,0.004 mol),己烯(3.36g,0.04 mol),Ph2SiH2(8.84 g,0.048 mol)加入25 mL烧瓶中,90℃下搅拌12 h,反应完成后,GC测得烯烃转化率为97.6%,β-加成产物选择性为98.8%。
实施例13:
一种应用茂金属催化剂催化不饱和化合物的硅氢加成反应:将二氯二茂锆(0.585 g,0.002 mol),金属钐粉(0.60 g,0.004 mol),辛烯 (4.48g,0.04 mol),Ph2SiH2(8.84 g,0.048 mol)加入25 mL烧瓶中,90℃下搅拌12 h,反应完成后,GC测得烯烃转化率为94.1%,β-加成产物选择性为98.7%。
实施例14:
一种应用茂金属催化剂催化不饱和化合物的硅氢加成反应:将二氯二茂锆(0.585 g,0.002 mol),金属钐粉(0.60 g,0.004 mol),苯乙酮(12.0 g,0.10 mol),Ph2SiH2(22.1 g,0.12 mol)加入50mL烧瓶中,80℃下搅拌6 h,反应完成后,GC测得苯乙酮转化率为98.6%。
实施例15:
一种应用茂金属催化剂催化不饱和化合物的硅氢加成反应:将二氯二茂钛(0.50 g,0.002 mol),金属钐粉(0.60 g,0.004 mol),己烯(3.36g,0.04 mol),Ph2SiH2(8.84 g,0.048 mol)加入25 mL烧瓶中,80℃下搅拌12 h,反应完成后,GC测得烯烃转化率为84.6%,β-加成产物选择性为98.7%。
实施例16:
一种应用茂金属催化剂催化不饱和化合物的硅氢加成反应:将二氯二茂钛(0.50 g,0.002 mol),金属钐粉(0.60 g,0.004 mol),己烯(3.36g,0.04 mol),Ph2SiH2(8.84 g,0.048 mol)加入25 mL烧瓶中,100℃下搅拌12 h,反应完成后,GC测得烯烃转化率为95.5%,β-加成产物选择性为97.8%。
实施例17:
一种应用茂金属催化剂催化不饱和化合物的硅氢加成反应:将二氯二茂钛(0.25 g,0.001 mol),金属钐粉(0.30 g,0.002 mol),己烯(3.36g,0.04 mol),Ph2SiH2(8.84 g,0.048 mol)加入25 mL烧瓶中,90℃下搅拌12 h,反应完成后,GC测得烯烃转化率为74.8%,β-加成产物选择性为98.9%。
实施例18:
一种应用茂金属催化剂催化不饱和化合物的硅氢加成反应:将二氯二茂锆(0.585 g,0.002 mol),金属钐粉(0.60 g,0.004 mol),对氯苯乙酮(15.4 g,0.10 mol),Ph2SiH2(22.1g,0.12 mol)加入50mL烧瓶中,80℃下搅拌6 h,反应完成后,GC测得对氯苯乙酮转化率为95.6%。
Claims (7)
1.一种以茂金属为催化剂的不饱和化合物硅氢加成反应,其特征在于,所述茂金属催化剂由一种茂金属配合物和一种金属粉末组成。
2.根据权利要求1所述的一种以茂金属为催化剂的不饱和化合物硅氢加成反应,其特征在于,茂金属配合物与金属粉末摩尔比为1:1~1:3。
3.根据权利要求1或2所述的一种以茂金属为催化剂的不饱和化合物硅氢加成反应,其特征在于,所述茂金属配合物为二氯二茂钛或二氯二茂锆。
4.根据权利要求1或2所述的一种以茂金属为催化剂的不饱和化合物硅氢加成反应,其特征在于,所述金属粉末为钐、镁、铝或锌中的任意一种。
5.根据权利要求2所述的一种以茂金属为催化剂的不饱和化合物硅氢加成反应,其特征在于,茂金属配合物与金属粉末摩尔比为1:2。
6.根据权利要求2所述的一种以茂金属为催化剂的不饱和化合物硅氢加成反应,其特征在于,不所述饱和化合物为烯烃或酮类化合物。
7.根据权利要求1、2、5或6所述的一种以茂金属为催化剂的不饱和化合物硅氢加成反应,其特征在于,所述茂金属催化剂应用于不饱和化合物硅氢加成反应,其温度条件为80~100℃。
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CN106831850A (zh) * | 2016-12-02 | 2017-06-13 | 杭州师范大学 | 一种硅氢加成反应 |
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