CN103387586B - 一种端乙烯基硅氧烷的制备方法 - Google Patents
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- 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
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
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Abstract
本发明涉及一种端乙烯基硅氧烷的制备方法,将R2R3Si(OR4)2、R1 2(CH2=CH)SiOSi(CH=CH2)R1 2、有机酸、催化剂按照摩尔比1:1~1.5:1~2.5:0.005~0.01加入到反应瓶中,R1为烷基,R2、R3相同或不同为烷基、芳烃基或取代的烷基、取代的芳烃基,R4为烷基,搅拌下升温至50~80℃,在此温度搅拌反应5~30分钟,加入脱水剂,继续在50~80℃反应2~5小时;反应结束后降至室温,稀释,水洗至中性,收集有机相,干燥、过滤、浓缩,减压蒸馏,收集相应压力和温度下馏分,得到端乙烯基硅氧烷化合物产品。本发明工艺条件温和,简便易行,产物相对纯净,易于分离。
Description
技术领域
本发明涉及一种端乙烯基硅氧烷的制备方法,属于有机硅合成技术领域。
背景技术
端乙烯基硅氧烷化合物R2 1(CH2=CH)SiO(R2R3)SiOSi(CH=CH2)R2 1因其含有的乙烯基可参与硅氢加成反应,适用于生产液体硅橡胶、加成型硅橡胶、高温胶、生胶、硅凝胶和乙烯基硅油等系列产品,在许多橡胶制品中都占据这必不可少的地位,是一类重要的工业原料。尤其是近年来,随着LED封装用有机硅材料的发展,含有苯基的乙烯基硅氧烷化合物可提高硅胶折射率,降低粘度,有广泛的应用前景。
通常制备端乙烯基硅氧烷化合物的方法有两种,一种是乙烯基氯硅烷与R2R3SiCl2共水解缩合法;一种是乙烯基封端剂与直链聚硅氧烷催化平衡法。这两种方法得到的往往是具有不同聚合度的混合物,其中三硅氧烷化合物R1 2(CH2=CH)SiO(R2R3)SiOSi(CH=CH2)R1 2的含量较低(小于30%),分离困难。
发明内容
本发明的目的是克服上述不足而提供一种端乙烯基硅氧烷的制备方法,该方法条件温和,产物易分离。
一种端乙烯基硅氧烷的制备方法,包括步骤如下:
(1)选取原料R2R3Si(OR4)2和R1 2(CH2=CH)SiOSi(CH=CH2)R1 2,其中,R1为烷基,R2、R3相同或不同为烷基、芳烃基或取代的烷基、取代的芳烃基,R4为烷基;
(2)将R2R3Si(OR4)2、R1 2(CH2=CH)SiOSi(CH=CH2)R1 2、有机酸、催化剂按照摩尔比1:1~1.5:1~2.5:0.005~0.01加入到反应瓶中,搅拌下升温至50~80℃,在此温度搅拌反应5~30分钟,加入脱水剂,继续在50~80℃反应2~5小时;
(3)反应结束后降至室温,加入非极性有机溶剂稀释,用去离子水洗至中性,收集有机相,干燥、过滤、浓缩,浓缩液减压蒸馏,收集相应压力和温度下馏分,得到端乙烯基硅氧烷化合物产品。
产品结构为:
上述制备方法中步骤(1)所述的原料,R1优选为含C1~4的烷基,进一步优选为甲基或乙基;R2、R3优选为含C1~6的烷基、含一个苯环的芳烃基,进一步优选含C1~4的直链烷基、苯基、苯甲基、苯乙基;R4优选为含C1~4的烷基,进一步优选甲基。
上述步骤(2)中所述的脱水剂的加入量为R2R3Si(OR4)2摩尔量的0.5~1.5倍。所述的有机酸为甲酸、乙酸或丙酸。所述的催化剂为强酸催化剂,选自盐酸、浓硫酸、三氟甲磺酸、强酸性离子交换树脂、固体酸中的一种或几种。所用的脱水剂为浓硫酸、醋酸酐或N,N’-二环己基碳二亚胺。
上述步骤(3)所述的非极性有机溶剂为苯、甲苯、二甲苯、正己烷或正庚烷。
本发明以有机酸提供质子,通过控制有机酸和R2R3Si(OR4)2的投料比得到以R2R3Si(OH)2为主产物的中间体。脱水剂的加入使R2R3Si(OH)2与R1 2(CH2=CH)SiOSi(CH=CH2)R1 2可以在温和的条件下高效地反应生成三硅氧烷化合物R1 2(CH2=CH)SiO(R2R3)SiOSi(CH=CH2)R1 2。上述两个步骤使得本发明与以往技术相比,产物纯度和产率都有明显提高。
本发明的有益效果是:
(1)工艺方法:原料价廉易得,工艺条件温和,简便易行,适合于工业化生产,生产成本低;
(2)制得的产品:产物相对纯净,易于分离,产率可达50%以上;纯度高。
附图说明
图1为本发明具体实施例1所得产物的1H NMR(CDCl3)谱图。
具体实施方式
下面结合实施例对本发明进一步说明。
实施例1
(CH3)2(CH2=CH)SiO(C6H5)2SiOSi(CH=CH2)(CH3)2的制备方法:
将二苯基二甲氧基硅烷(61.09g),三氟甲磺酸(0.20g),1,3-二乙烯基-1,1,3,3-四甲基二硅氧烷(46.60g),乙酸(37.81g)加入四口圆底烧瓶中,升温至65℃,反应30分钟,然后加入醋酸酐(12.76g),在65℃下继续反应2小时。反应完毕后降至室温,加入甲苯稀释,用去离子水洗至中性。收集甲苯层,加入无水氯化钙干燥。滤去干燥剂,滤液浓缩除去甲苯。浓缩液减压蒸馏,收集165-170℃/4mmHg馏分,产率51.2%,纯度99%。产物结构经过1H NMR(CDCl3)谱图得到证实(附图1):δ(ppm):0.156(12H,-CH3),5.71-5.938(4H,=CH2),6.09-6.149(2H,-CH=),7.318-7.584(10H,-C6H5)。
实施例2
(CH3)2(CH2=CH)SiO(C6H5)(CH3)SiOSi(CH=CH2)(CH3)2的制备方法:
将甲基苯基二甲氧基硅烷(18.20g),三氟甲磺酸(0.10g),1,3-二乙烯基-1,1,3,3-四甲基二硅氧烷(18.64g),乙酸(15.13g)加入四口圆底烧瓶中,升温至70℃,反应30分钟,然后加入醋酸酐(5.10g),在70℃下继续反应1小时。反应完毕后降至室温,加入甲苯稀释,用去离子水洗至中性。收集甲苯层,加入无水氯化钙干燥。滤去干燥剂,滤液浓缩除去甲苯。浓缩液减压蒸馏,收集115-120℃/5mmHg馏分,产率54.0%,纯度96%。
实施例3
(CH3)2(CH2=CH)SiO(CH3)2SiOSi(CH=CH2)(CH3)2的制备方法:
将二甲基二甲氧基硅烷(24.00g),三氟甲磺酸(0.20g),1,3-二乙烯基-1,1,3,3-四甲基二硅氧烷(37.21g),乙酸(30.25g)加入四口圆底烧瓶中,升温至50℃,反应30分钟,然后加入醋酸酐(10.21g),在50℃下继续反应2小时。反应完毕后降至室温,加入甲苯稀释,用去离子水洗至中性。收集甲苯层,加入无水氯化钙干燥。滤去干燥剂,滤液浓缩除去甲苯。浓缩液减压蒸馏,收集77℃-82℃/20mmHg馏分,产率51.7%,纯度98%。
上述是对本发明的优选实施方案的描述,但并非对本发明保护范围的限制,在本发明的技术方案的基础上,本领域技术人员不需要付出创造性劳动即可做出的各种修改或变形仍在本发明的保护范围以内。
Claims (6)
1.一种端乙烯基硅氧烷的制备方法,其特征是,包括步骤如下:
(1)选取原料R2R3Si(OR4)2和R1 2(CH2=CH)SiOSi(CH=CH2)R1 2,其中,R1为甲基或乙基;R2、R3选含C1~4的直链烷基,R4为甲基;
(2)将R2R3Si(OR4)2、R1 2(CH2=CH)SiOSi(CH=CH2)R1 2、有机酸、催化剂按照摩尔比1:1~1.5:1~2.5:0.005~0.01加入到反应瓶中,搅拌下升温至50~80℃,在此温度搅拌反应5~30分钟,加入脱水剂,继续在50~80℃反应2~5小时;
(3)反应结束后降至室温,加入非极性有机溶剂稀释,用去离子水洗至中性,收集有机相,干燥、过滤、浓缩,浓缩液减压蒸馏,收集相应压力和温度下馏分,得到端乙烯基硅氧烷化合物产品。
2.根据权利要求1所述的一种端乙烯基硅氧烷的制备方法,其特征是,步骤(2)中所述的脱水剂的加入量为R2R3Si(OR4)2摩尔量的0.5~1.5倍。
3.根据权利要求1所述的一种端乙烯基硅氧烷的制备方法,其特征是,所述的有机酸为甲酸、乙酸或丙酸。
4.根据权利要求1所述的一种端乙烯基硅氧烷的制备方法,其特征是,所述的催化剂为强酸催化剂,选自盐酸、浓硫酸、三氟甲磺酸、强酸性离子交换树脂、固体酸中的一种或几种。
5.根据权利要求1所述的一种端乙烯基硅氧烷的制备方法,其特征是,所用的脱水剂为浓硫酸、醋酸酐或N,N’-二环己基碳二亚胺。
6.根据权利要求1所述的一种端乙烯基硅氧烷的制备方法,其特征是,步骤(3)所述的非极性有机溶剂为苯、甲苯、二甲苯、正己烷或正庚烷。
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