TW201602124A - 矽氮烷化合物的製造方法 - Google Patents
矽氮烷化合物的製造方法 Download PDFInfo
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- TW201602124A TW201602124A TW104110982A TW104110982A TW201602124A TW 201602124 A TW201602124 A TW 201602124A TW 104110982 A TW104110982 A TW 104110982A TW 104110982 A TW104110982 A TW 104110982A TW 201602124 A TW201602124 A TW 201602124A
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- 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
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
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Abstract
本發明解決手段為提供一種矽氮烷化合物的製造方法,其特徵為使下述一般式(1)所示之鹵矽烷化合物、R1nSiX(4-n) (1)(式中,R1係相同或相異為氫原子或碳數1~20之經取代或非經取代之1價烴基、X為鹵原子,n為0~3之整數,n為2或3時,R1係彼此鍵結而可與此等所鍵結之矽原子一起形成碳數2~20之環),與下述一般式(2)所示之含胺基之化合物、R2R3NH (2)(式中,R2、R3係氫原子或碳數1~20之經取代或非經取代之1價烴基),或下述一般式(3)所示之含胺基之化合物進行反應,
□
(R4係可含有雜原子之碳數1~20之2價有機基)。,以製造矽氮烷化合物之方法中,將與目的物相同之矽氮烷化合物作為溶劑使用。
本發明效果為根據本發明,可效率良好地製造作為塗料添加劑、高分子改質劑、醫藥品類或農藥類之合成中間物之有用的矽氮烷化合物。
Description
本發明係關於作為塗料添加劑、高分子改質劑、醫藥品類或農藥類之合成中間物有用之矽氮烷化合物的製造方法。
矽氮烷化合物係有用於作為塗料添加劑、高分子改質劑、醫藥品類或農藥類之合成中間物。
作為製造矽氮烷化合物之方法,周知有使鹵矽烷化合物與含胺基之化合物進行反應之方法。此反應中,除了作為目的之矽氮烷化合物之外,鹵化氫為副產物。此鹵化氫藉由與含胺基之化合物反應,含胺基之化合物的鹵化氫鹽為化學計算量生成。生成之含胺基之化合物的鹵化氫鹽通常為固體,不溶解於反應系統並於反應時析出,反應液成為泥漿狀而阻礙攪拌。因此反應時一般為以成為可攪拌的方式來添加、使用溶劑,例如美國專利第2429883號說明書(專利文獻1)中有記載使用二乙基醚、苯作為溶劑之矽氮烷化合物的製造方法。
[專利文獻1]美國專利第2429883號說明書
然而,為了維持攪拌必須使用大量的溶劑,又蒸餾單離作為目的之矽氮烷化合物時,必須有溶劑的分餾步驟,故煩雜的操作變為必要。因此,尋求更有效率地地的矽氮烷化合物的製造方法。
本發明因為回應該需求,以提供效率良好之矽氮烷化合物作為目的。
本發明者們為了達成上述目的經努力研討的結果,發現在使鹵矽烷化合物與含胺基之化合物反應以製造矽氮烷化合物之方法中,將藉由上述反應所生成之矽氮烷化合物本身作為溶劑使用時,提昇所生成之含胺基之化合物的含鹵化氫鹽之泥漿的流動性,其結果可減低溶劑的使用量,而且由於溶劑為矽氮烷化合物本身,不需要蒸餾時的溶劑之分餾步驟,可更有效率地地製造矽氮烷化合物,而終至完成本發明。
據此,本發明係提供下述所示之矽氮烷化合
物的製造方法。
一種矽氮烷化合物的製造方法,其特徵為使下述一般式(1)所示之鹵矽烷化合物、R1 nSiX(4-n) (1)(式中,R1係相同或相異為氫原子或碳數1~20之經取代或非經取代之1價烴基、X為鹵原子,n為0~3之整數,n為2或3時,R1係彼此鍵結而可與此等所鍵結之矽原子一起形成碳數2~20之環),與下述一般式(2)所示之含胺基之化合物、R2R3NH (2)(式中,R2、R3係氫原子或碳數1~20之經取代或非經取代之1價烴基),或下述一般式(3)所示之含胺基之化合物進行反應,
(式中,R4係可包含雜原子之碳數1~20之2價有機基),以製造矽氮烷化合物之方法中,將與目的物相同之矽氮烷化合物作為溶劑使用。
如[1]之矽氮烷化合物的製造方法,其中,前述矽氮烷化合物係下述一般式(4)、(5)、(6)或(7)所示之矽氮烷化合物,
R1 nSi(NR2R3)(4-n) (4)(式中,R1、R2、R3、n係與上述相同),
(式中,R1、R4、n係與上述相同),
(式中,R1、R3係與上述相同,n為3),
(式中,R1、R3係與上述相同、a為2~20之整數,n為2)。
如[1]或[2]之矽氮烷化合物的製造方法,其中,上述一般式(2)之R2及R3係碳數1~20之經取代或非經取代之1價烴基。
如[1]~[3]中任一項之矽氮烷化合物的製造方法,其係至少包含:反應後,將生成之含胺基之化合物的鹵化氫鹽由鹼水溶液溶解之步驟、將該含胺基之化合物從包含矽氮烷化合物之有機層分離之步驟。
根據本發明,可有效率地地製造有用於作為塗料添加劑、高分子改質劑、醫藥品類或農藥類之合成中間物之矽氮烷化合物。
本發明之矽氮烷化合物的製造方法係使下述一般式(1)所示之鹵矽烷化合物、R1 nSiX(4-n) (1)(式中,R1係相同或相異為氫原子或碳數1~20之經取代或非經取代之1價烴基,X為鹵原子,n為0~3之整數,n為2或3時、R1係彼此鍵結而可與此等所鍵結之矽原子一起形成碳數2~20之環)。與下述一般式(2)所示之含胺基之化合物、R2R3NH (2)(式中,R2、R3係氫原子或碳數1~20之經取代或非經取代之1價烴基)。或下述一般式(3)所示之含胺基之化合物進行反應,
(式中,R4係可含有雜原子之碳數1~20之2價有機基)。
以製造矽氮烷化合物之方法中,將藉由上述反應所生成之矽氮烷化合物本身作為溶劑使用者。
於此,在上述一般式(1)、(2)之R1、R2、R3為氫原子或碳數1~20,較佳為碳數1~10,更佳為碳數1~5之經取代或非經取代之1價烴基,可列舉直鏈狀、分支鏈狀或環狀之烷基、烯基、芳基、芳烷基等。具體而言,例示有甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、癸基、十二烷基、十四烷基、十六烷基、十八烷基、二十烷基等之直鏈狀之烷基、異丙基、異丁基、sec-丁基、tert-丁基、三甲基丙基(Thexyl)、2-乙基己基等之分支鏈狀之烷基、環戊基、環己基等之環狀之烷基、乙烯基、烯丙基、丙烯基等之烯基、苯基、甲苯基等之芳基、苄基等之芳烷基等,尤其是以甲基、乙基、異丙基、sec-丁基、tert-丁基為佳。又,烴基之氫原子之一部分或全部可被取代,作為該取代基,具體而言,例如可列舉甲氧基、乙氧基、(異)丙氧基等之烷氧基;氟原子、氯原子、溴原子、碘原子等之鹵原子;氰基;胺基、碳數2~10之醯基、三氯矽烷基、各烷基或各烷氧基為碳數1~5之三烷基矽烷基、二烷基單氯矽烷基、單烷基二氯矽烷基、三烷氧基矽烷基、二烷基單烷氧基矽烷基或單烷基二烷氧基矽烷基。
在上述一般式(3)之R4係可包含雜原子之碳數1~20之2價有機基,具體而言,例示有亞甲基、伸乙基、甲基伸乙基、伸丙基、甲基伸丙基、四亞甲基、六亞
甲基、八亞甲基、十亞甲基、異伸丁基等之伸烷基、伸苯基等之亞芳基、亞甲基伸苯基、亞甲基伸苯基亞甲基等之亞芳烷基、3-氧雜伸戊基、3-氮雜伸戊基、3-甲基-3-氮雜伸戊基等之含氧原子、氮原子等之雜原子之伸烷基。
在上述一般式(1)之鹵原子,具體而言,可列舉氟原子、氯原子、溴原子、碘原子。
作為上述一般式(1)所示之鹵矽烷化合物的具體例,例示有二甲基氯矽烷、三甲基氯矽烷、二乙基氯矽烷、乙基二甲基氯矽烷、二乙基甲基氯矽烷、三乙基氯矽烷、乙烯基二甲基氯矽烷、三丙基氯矽烷、三異丙基氯矽烷、三丁基氯矽烷、t-丁基二甲基氯矽烷、二t-丁基甲基氯矽烷、三t-丁基氯矽烷、三異丁基氯矽烷、三sec-丁基氯矽烷、己基二甲基氯矽烷、三甲基丙基(Thexyl)二甲基氯矽烷、辛基二甲基氯矽烷、癸基二甲基氯矽烷、十八烷基二甲基氯矽烷、環戊基二甲基氯矽烷、環己基二甲基氯矽烷、三環戊基氯矽烷、三環己基氯矽烷、二甲基苯基氯矽烷、甲基二苯基氯矽烷、三苯基氯矽烷、t-丁基二苯基氯矽烷、二t-丁基苯基氯矽烷、苯乙烯基二甲基氯矽烷、2-氰乙基二甲基氯矽烷、乙醯氧基丙基二甲基氯矽烷、3-丙烯醯氧基丙基二甲基氯矽烷、3-甲基丙烯醯氧基丙基二甲基氯矽烷、氯甲基二甲基氯矽烷、3-氯丙基二甲基氯矽烷、3,3,3-三氟丙基二甲基氯矽烷、3,3,4,4,5,5,6,6,6-九氟己基二甲基氯矽烷、3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-十七氟癸基二甲基氯矽烷、二氯矽烷、甲基二氯矽烷、二
甲基二氯矽烷、乙基二氯矽烷、二乙基二氯矽烷、乙烯基甲基二氯矽烷、二乙烯基二氯矽烷、丙基甲基二氯矽烷、二丁基二氯矽烷、t-丁基甲基二氯矽烷、二t-丁基二氯矽烷、二異丁基二氯矽烷、二sec-丁基二氯矽烷、己基甲基二氯矽烷、三甲基丙基(Thexyl)甲基二氯矽烷、辛基甲基二氯矽烷、癸基甲基二氯矽烷、十八烷基甲基二氯矽烷、環戊基甲基二氯矽烷、環己基甲基二氯矽烷、二環戊基二氯矽烷、二環己基二氯矽烷、甲基苯基二氯矽烷、二苯基二氯矽烷、t-丁基苯基二氯矽烷、苯乙烯基甲基二氯矽烷、2-氰乙基甲基二氯矽烷、乙醯氧基丙基甲基二氯矽烷、3-丙烯醯氧基丙基甲基二氯矽烷、3-甲基丙烯醯氧基丙基甲基二氯矽烷、氯甲基甲基二氯矽烷、3-氯丙基甲基二氯矽烷、3,3,3-三氟丙基甲基二氯矽烷、3,3,4,4,5,5,6,6,6-九氟己基甲基二氯矽烷、3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-十七氟癸基甲基二氯矽烷、三氯矽烷、甲基三氯矽烷、乙基三氯矽烷、乙烯基三氯矽烷、丙基三氯矽烷、異丙基三氯矽烷、丁基三氯矽烷、t-丁基三氯矽烷、異丁基三氯矽烷、sec-丁基三氯矽烷、己基三氯矽烷、三甲基丙基(Thexyl)三氯矽烷、辛基三氯矽烷、癸基三氯矽烷、十八烷基三氯矽烷、環戊基三氯矽烷、環己基三氯矽烷、苯基三氯矽烷、苯乙烯基三氯矽烷、2-氰乙基三氯矽烷、乙醯氧基丙基三氯矽烷、3-丙烯醯氧基丙基三氯矽烷、3-甲基丙烯醯氧基丙基三氯矽烷、氯甲基三氯矽烷、3-氯丙基三氯矽烷、3,3,3-三氟丙基三氯矽烷、3,3,4,4,5,5,6,6,6-九氟
己基三氯矽烷、3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-十七氟癸基三氯矽烷、四氯矽烷、1,2-雙(二甲基氯矽烷基)乙烷、1,2-雙(甲基二氯矽烷基)乙烷、1,2-雙(三氯矽烷基)乙烷、1,6-雙(二甲基氯矽烷基)己烷、1,6-(甲基二氯矽烷基)己烷、1,6-雙(三氯矽烷基)己烷、雙(二甲基氯矽烷基)降莰烷、雙(甲基二氯矽烷基)降莰烷、雙(三氯矽烷基)降莰烷、二甲基溴矽烷、三甲基溴矽烷、二乙基溴矽烷、乙基二甲基溴矽烷、二乙基甲基溴矽烷、三乙基溴矽烷、乙烯基二甲基溴矽烷、三丙基溴矽烷、三異丙基溴矽烷、三丁基溴矽烷、t-丁基二甲基溴矽烷、二t-丁基甲基溴矽烷、三t-丁基溴矽烷、三異丁基溴矽烷、三sec-丁基溴矽烷、己基二甲基溴矽烷、三甲基丙基(Thexyl)二甲基溴矽烷、辛基二甲基溴矽烷、癸基二甲基溴矽烷、十八烷基二甲基溴矽烷、環戊基二甲基溴矽烷、環己基二甲基溴矽烷、三環戊基溴矽烷、三環己基溴矽烷、二甲基苯基溴矽烷、甲基二苯基溴矽烷、三苯基溴矽烷、t-丁基二苯基溴矽烷、二t-丁基苯基溴矽烷、苯乙烯基二甲基溴矽烷、2-氰乙基二甲基溴矽烷、乙醯氧基丙基二甲基溴矽烷、3-丙烯醯氧基丙基二甲基溴矽烷、3-甲基丙烯醯氧基丙基二甲基溴矽烷、溴甲基二甲基溴矽烷、3-溴丙基二甲基溴矽烷、3,3,3-三氟丙基二甲基溴矽烷、3,3,4,4,5,5,6,6,6-九氟己基二甲基溴矽烷、3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-十七氟癸基二甲基溴矽烷、二溴矽烷、甲基二溴矽烷、二甲基二溴矽烷、乙基二溴矽烷、二乙基二溴矽烷、乙烯基甲基
二溴矽烷、二乙烯基二溴矽烷、丙基甲基二溴矽烷、二丁基二溴矽烷、t-丁基甲基二溴矽烷、二t-丁基二溴矽烷、二異丁基二溴矽烷、二sec-丁基二溴矽烷、己基甲基二溴矽烷、三甲基丙基(Thexyl)甲基二溴矽烷、辛基甲基二溴矽烷、癸基甲基二溴矽烷、十八烷基甲基二溴矽烷、環戊基甲基二溴矽烷、環己基甲基二溴矽烷、二環戊基二溴矽烷、二環己基二溴矽烷、甲基苯基二溴矽烷、二苯基二溴矽烷、t-丁基苯基二溴矽烷、苯乙烯基申基二溴矽烷、2-氰乙基甲基二溴矽烷、乙醯氧基丙基甲基二溴矽烷、3-丙烯醯氧基丙基甲基二溴矽烷、3-甲基丙烯醯氧基丙基甲基二溴矽烷、溴甲基甲基二溴矽烷、3-溴丙基甲基二溴矽烷、3,3,3-三氟丙基甲基二溴矽烷、3,3,4,4,5,5,6,6,6-九氟己基甲基二溴矽烷、3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-十七氟癸基甲基二溴矽烷、三溴矽烷、甲基三溴矽烷、乙基三溴矽烷、乙烯基三溴矽烷、丙基三溴矽烷、異丙基三溴矽烷、丁基三溴矽烷、t-丁基三溴矽烷、異丁基三溴矽烷、sec-丁基三溴矽烷、己基三溴矽烷、三甲基丙基(Thexyl)三溴矽烷、辛基三溴矽烷、癸基三溴矽烷、十八烷基三溴矽烷、環戊基三溴矽烷、環己基三溴矽烷、苯基三溴矽烷、苯乙烯基三溴矽烷、2-氰乙基三溴矽烷、乙醯氧基丙基三溴矽烷、3-丙烯醯氧基丙基三溴矽烷、3-甲基丙烯醯氧基丙基三溴矽烷、溴甲基三溴矽烷、3-溴丙基三溴矽烷、3,3,3-三氟丙基三溴矽烷、3,3,4,4,5,5,6,6,6-九氟己基三溴矽烷、3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-十七
氟癸基三溴矽烷、四溴矽烷、1,2-雙(二甲基溴矽烷基)乙烷、1,2-雙(甲基二溴矽烷基)乙烷、1,2-雙(三溴矽烷基)乙烷、1,6-雙(二甲基溴矽烷基)己烷、1,6-(甲基二溴矽烷基)己烷、1,6-雙(三溴矽烷基)己烷、雙(二甲基溴矽烷基)降莰烷、雙(甲基二溴矽烷基)降莰烷、雙(三溴矽烷基)降莰烷等。
又,作為上述一般式(2)所示之含胺基之化合物的具體例,例示有氨、甲基胺、乙基胺、丙基胺、異丙基胺、烯丙基胺、丁基胺、戊基胺、己基胺、辛基胺、2-乙基己基胺、苄基胺、環戊基胺、環己基胺、乙烯二胺、二乙烯三胺、三乙烯四胺、1,6-二胺基己烷、苯胺、甲苯胺、二甲苯胺、萘基胺、苯二甲基二胺、二甲基胺、二乙基胺、二丙基胺、二異丙基胺、二烯丙基胺、二丁基胺、二戊基胺、二辛基胺、二(2-乙基己基)胺、N-甲基苯胺、二苯基胺等。
又,作為上述一般式(3)所示之含胺基之化合物的具體例,例示有乙烯亞胺、吡咯烷、哌啶、甲基哌啶(pipecoline)、哌嗪、N-甲基哌嗪、N-乙基哌嗪、嗎啉、咪唑、三唑、吲哚等。
亦為在本發明之目的物,反應中作為溶劑使用之矽氮烷化合物,係下述一般式(4)、(5)、(6)或(7)所示之矽氮烷化合物。
R1 nSi(NR2R3)(4-n) (4)(式中,R1、R2、R3、n係與上述相同)。
本發明之鹵矽烷化合物的使用量雖並未特別限定,但從反應性、生產性方面,相對於含胺基之化合物的反應所使用之N-H鍵1莫耳,以鹵矽烷化合物之矽-鹵原子鍵換算為0.1~4.0莫耳,尤其是以0.2~3.0莫耳的範圍為佳。
本發明中,使上述一般式(1)所示之鹵矽烷化合物、與上述一般式(2)或上述一般式(3)所示之含胺基之化合物進行反應時,係將藉由反應所生成之矽氮烷化合物本身作為溶劑使用者。
作為溶劑使用之矽氮烷化合物,雖然由合成反應液去除鹽者、經蒸餾生成者皆可使用,但從所得之矽氮烷化合物的品質方面來看,使用以經蒸餾生成者為佳。
作為溶劑使用之矽氮烷化合物的使用量雖並未特別限定,但從反應性、生產性方面,相對於含胺基之化合物之反應所使用之N-H鍵1莫耳,為0.1~10莫耳,尤其以0.5~5莫耳的範圍為佳。
本發明之含胺基之化合物的矽烷基化反應中,雖鹵化氫為副產物,此係可捕捉上述一般式(2)或上述一般式(3)所示之含胺基之化合物本身作為鹼,亦可捕捉其他胺化合物作為鹼。作為其他胺化合物,除了上述一般式(2)或上述一般式(3)所示之含胺基之化合物之外,例示有三甲基胺、三乙基胺、三丙基胺、三丁基胺、乙基二異丙基胺、吡啶、二甲基胺基吡啶、二甲基苯胺、甲基咪唑、四甲基乙烯二胺、1,8-二氮雜二環[5.4.0]十一烯-7等。
其他胺化合物的使用量雖並未特別限定,但從反應性、生產性方面來看,相對於含胺基之化合物的反應所使用之N-H鍵1莫耳,為0.3~10.0莫耳,尤其以0.5~5.0莫耳的範圍為佳。
上述反應雖無觸媒亦可進行,但以提昇反應速度為目的亦可使用觸媒。作為所使用之觸媒,例示有硫酸、甲烷磺酸、苯磺酸、甲苯磺酸、十二烷基苯磺酸、三氟甲烷磺酸等之磺酸化合物、鹽酸、硝酸、及上述酸之鹽。
觸媒的使用量雖並未特別限定,但從反應性、生產性方面來看,相對於含胺基之化合物的反應所使
用之N-H鍵1莫耳為0.0001~0.1莫耳,尤其以0.001~0.05莫耳的範圍為佳。
上述反應之反應溫度雖並未特別限定,但為0~200℃,尤其以10~180℃為佳。
尚,於不損及本發明之目的之範圍內,可添加矽氮烷化合物本身以外的溶劑。作為可使用之溶劑,例示有戊烷、己烷、環己烷、庚烷、異辛烷、苯、甲苯、二甲苯等之烴系溶劑、二乙基醚、四氫呋喃、二噁烷等之醚系溶劑、乙酸乙酯、乙酸丁酯等之酯系溶劑、乙腈、N,N-二甲基甲醯胺等之非質子系極性溶劑、二氯甲烷、氯仿等之氯化烴系溶劑等。此等之溶劑雖可單獨1種使用,又亦可混合2種以上使用,但其使用量相對於矽氮烷化合物溶劑1莫耳為0.1~10莫耳,尤其以0.5~2莫耳為佳。
反應結束後產生含胺基之化合物之鹽酸鹽,此雖可藉由將反應液過濾、或添加水、氫氧化鈉水溶液、氫氧化鉀水溶液等之鹼水溶液,來進行分離等之方法進行去除,但添加鹼水溶液時,從含胺基之化合物的鹵化氫鹽游離含胺基之化合物,為了使含胺基之化合物成為可回收,以採用添加鹼水溶液之方法較佳。
從如以上般進行去除鹽之反應液,可用蒸餾等通常之方法回收目的物。
以下,雖顯示實施例與比較例具體說明本發
明,但本發明並非被限制於下述之實施例。
於具備攪拌機、迴流器、滴定漏斗及溫度計之燒瓶,投入二甲基二氯矽烷103.3g(0.8莫耳)、作為溶劑之雙(二乙基胺基)二甲基矽烷200g(0.99莫耳)、甲烷磺酸0.38g(0.004莫耳),並加熱至60℃。穩定內溫後,耗費3小時滴定二乙基胺245.6g(3.4莫耳),進而於其溫度攪拌1小時。冷卻至室溫後,加入400g之20質量%氫氧化鈉水溶液,分液、蒸餾有機層。得到336.7g之雙(二乙基胺基)二甲基矽烷作為沸點78℃/2.0kPa之餾分(以二甲基二氯矽烷換算的收率84%)。又,相對於燒瓶內最大質量(加入20質量%氫氧化鈉水溶液時之燒瓶內的總質量)之雙(二乙基胺基)二甲基矽烷的收量,係燒瓶內最大質量每1kg為144.0g。
除了將溶劑變更為甲苯200g之外,其他與實施例1同樣進行反應。藉由於二乙基胺滴定途中所生成之鹽變得無法攪拌,必須再追加200g甲苯。冷卻至室溫後,加入400g之20質量%氫氧化鈉水溶液,分液、蒸餾有機層。餾除甲苯後,得到133.9g之雙(二乙基胺基)二甲基矽烷作為沸點78℃/2.0kPa之餾分(以二甲基二氯矽烷換算的收率83%)。又,相對於燒瓶內最大質量(加入20質量%氫氧化
鈉水溶液時之燒瓶內的總質量)之雙(二乙基胺基)二甲基矽烷的收量,係燒瓶內最大質量每1kg為116.5g,與實施例1相比較成為生產性不良的結果。
於具備攪拌機、迴流器、滴定漏斗及溫度計之燒瓶,投入甲基苯基二氯矽烷152.9g(0.8莫耳)、作為溶劑之雙(二乙基胺基)甲基苯基矽烷150g(0.57莫耳)、甲烷磺酸0.38g(0.004莫耳),並加熱至60℃。穩定內溫後,耗費3小時滴定二乙基胺245.6g(3.4莫耳),進而於其溫度攪拌1小時。冷卻至室溫後,加入400g之20質量%氫氧化鈉水溶液,分液、蒸餾有機層。得到325.9g之雙(二乙基胺基)甲基苯基矽烷作為沸點126℃/0.4kPa之餾分(以甲基苯基二氯矽烷換算的收率83%)。
除了將溶劑變更為二甲苯150g之外,其他與實施例2同樣進行反應。藉由於二乙基胺滴定途中所生成之鹽變得無法攪拌,必須再追加180g二甲苯。冷卻至室溫後,加入400g之20質量%氫氧化鈉水溶液,分液、蒸餾有機層。餾除甲苯後,得到174.0g之雙(二乙基胺基)甲基苯基矽烷作為沸點82℃/1.0kPa之餾分(以甲基苯基二氯矽烷換算的收率82%)。
於具備攪拌機、迴流器、滴定漏斗及溫度計之燒瓶,投入甲基乙烯基二氯矽烷112.9g(0.8莫耳)、作為溶劑之雙(二乙基胺基)甲基乙烯矽烷200g(0.93莫耳)、甲烷磺酸0.38g(0.004莫耳),並加熱至60℃。穩定內溫後,耗費3小時滴定二乙基胺245.6g(3.4莫耳),進而於其溫度攪拌1小時。冷卻至室溫後,加入400g之20質量%氫氧化鈉水溶液,分液、蒸餾有機層。得到344.7g之雙(二乙基胺基)甲基乙烯基矽烷作為沸點82℃/1.0kPa之餾分(以甲基乙烯基二氯矽烷換算的收率83%)。
除了將溶劑變更為甲苯200g之外,其他與實施例3同樣進行反應。藉由於二乙基胺滴定途中所生成之鹽變得無法攪拌,必須再追加200g甲苯。冷卻至室溫後,加入400g之20質量%氫氧化鈉水溶液,分液、蒸餾有機層。餾除甲苯後,得到140.4g之雙(二乙基胺基)甲基乙烯基矽烷作為沸點82℃/1.0kPa之餾分(以甲基乙烯基二氯矽烷換算的收率82%)。
於具備攪拌機、迴流器、滴定漏斗及溫度計之燒瓶,投入三乙基氯矽烷120.6g(0.8莫耳)、作為溶劑之二丁基胺基三乙基矽烷100g(0.41莫耳)、甲烷磺酸0.38g(0.004
莫耳),並加熱至60℃。穩定內溫後,耗費3小時滴定二丁基胺217.0g(1.7莫耳),進而於其溫度攪拌1小時。冷卻至室溫後,加入200g之20質量%氫氧化鈉水溶液,分液、蒸餾有機層。得到304.5g之二丁基胺基三乙基矽烷作為沸點86℃/0.4kPa之餾分(以三乙基氯矽烷換算的收率84%)。
除了將溶劑變更為己烷100g之外,其他與實施例4同樣進行反應。藉由於二丁基胺滴定途中所生成之鹽變得無法攪拌,必須再追加100g己烷。冷卻至室溫後,加入200g之20質量%氫氧化鈉水溶液,分液、蒸餾有機層。餾除甲苯後,得到161.1g之二丁基胺基三乙基矽烷作為沸點86℃/0.4kPa之餾分(以三乙基氯矽烷換算的收率83%)。
Claims (4)
- 一種矽氮烷化合物的製造方法,其特徵為使下述一般式(1)所示之鹵矽烷化合物、R1 nSiX(4-n) (1)(式中,R1係相同或相異為氫原子或碳數1~20之經取代或非經取代之1價烴基、X為鹵原子,n為0~3之整數,n為2或3時,R1係彼此鍵結而可與此等所鍵結之矽原子一起形成碳數2~20之環),與下述一般式(2)所示之含胺基之化合物、R2R3NH (2)(式中,R2、R3係氫原子或碳數1~20之經取代或非經取代之1價烴基),或下述一般式(3)所示之含胺基之化合物進行反應,
- 如請求項1之矽氮烷化合物的製造方法,其中,前述矽氮烷化合物係下述一般式(4)、(5)、(6)或(7)所示之矽氮烷化合物,R1 nSi(NR2R3)(4-n) (4) (式中,R1、R2、R3、n係與上述相同),
- 如請求項1或2之矽氮烷化合物的製造方法,其中,上述一般式(2)之R2及R3係碳數1~20之經取代或非經取代之1價烴基。
- 如請求項1或2之矽氮烷化合物的製造方法,其係至少包含:反應後,將生成之含胺基之化合物的鹵化氫鹽由鹼水溶液溶解之步驟、將該含胺基之化合物從包含矽氮烷化合物之有機層分離之步驟。
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