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1. 发明授权

US07598413B2 Process for producing fluorine-containing alkylsulfonylaminoethyl α-substituted acrylate 有权
标题翻译：含氟烷基磺酰氨基乙基α-取代丙烯酸酯的制备方法
公开(公告)号：US07598413B2
公开(公告)日：2009-10-06
申请号：US12187823
申请日：2008-08-07
申请人： Takeo Komata , Ryo Nadano , Makoto Matsuura
发明人： Takeo Komata , Ryo Nadano , Makoto Matsuura
IPC分类号： C07C69/52
CPC分类号： C07C303/38 , C07C311/09
摘要： There is provided a process for producing a fluorine-containing alkylsulfonylaminoethyl α-substituted acrylate of the formula [3] by reaction of an aminoethyl α-substituted acrylate of the formula [1a] with a fluorine-containing alkylsulfonic fluoride of the formula [2], or by reaction of an aminoethyl a-substituted acrylate salt of the formula [1b] with a fluorine-containing alkylsulfonic fluoride of the formula [2] in the presence of a base, wherein a fluorine-containing compound is used as a reaction solvent: where R1 is a hydrogen atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tertbutyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group or perfluoroethyl group; R2 is a fluorine-containing alkyl group having a carbon number of 1 to 6; Xn− is a counter anion (n is a positive integer); and Y is a fluorine atom, chlorine atom or bromine atom.
摘要翻译：提供了通式[1a]的α-氨基乙基α取代丙烯酸酯与式[2]的含氟烷基磺酸氟化物反应制备式[3]的含氟烷基磺酰氨基乙基α-取代丙烯酸酯的方法，或通过式[1b]的氨基乙基α-取代的丙烯酸盐与式[2]的含氟烷基磺酸氟化物在碱的存在下反应，其中使用含氟化合物作为反应溶剂：其中R1是氢原子，甲基，乙基，正丙基，异丙基，正丁基，仲丁基，叔丁基，氟甲基，二氟甲基，三氟甲基或全氟乙基; R2是碳数为1〜6的含氟烷基; Xn-为抗衡阴离子（n为正整数）; Y是氟原子，氯原子或溴原子。

2. 发明授权

US07115771B2 Process for producing fluorine-containing alkylsulfonylaminoethyl α-substituted acrylate 有权
标题翻译：含氟烷基磺酰氨基乙基α-取代丙烯酸酯的制备方法
公开(公告)号：US07115771B2
公开(公告)日：2006-10-03
申请号：US11068824
申请日：2005-03-02
申请人： Takeo Komata , Ryo Nadano , Makoto Matsuura
发明人： Takeo Komata , Ryo Nadano , Makoto Matsuura
IPC分类号： C07C69/52
CPC分类号： C07C303/38 , C07C311/09
摘要： The present invention provides a process for producing a fluorine-containing alkylsulfonylaminoethyl α-substituted acrylate represented by general formula [3]: which comprises reacting an aminoethyl α-substituted acrylate represented by general formula [1a] or a salt thereof: with a fluorine-containing alkylsulfonyl halide represented by general formula [2a] or a fluorine-containing alkylsulfonic anhydride represented by general formula [2b]:
摘要翻译：本发明提供由通式[3]表示的含氟烷基磺酰基氨基乙基α-取代丙烯酸酯的制备方法：其包括使通式[1a]表示的α-取代的氨基乙基α-取代的丙烯酸酯或其盐与氟 - 由通式[2a]表示的含烷基磺酰卤或由通式[2b]表示的含氟烷基磺酸酐：

3. 发明申请

US20110137073A1 Process for Producing Alpha-Substituted Norbornanyl Acrylates 有权
标题翻译：生产α-取代的降冰片烷基丙烯酸酯的方法
公开(公告)号：US20110137073A1
公开(公告)日：2011-06-09
申请号：US13058115
申请日：2009-08-27
申请人： Makoto Matsuura , Ryo Nadano , Takeo Komata
发明人： Makoto Matsuura , Ryo Nadano , Takeo Komata
IPC分类号： C07C67/04
CPC分类号： C07C67/04 , C07C2602/42 , C07C69/653
摘要： Disclosed is a process for producing α-substituted norbornanyl acrylates efficiently on an industrial scale while suppressing the formation of by-products derived from intramolecular cyclization, excessive addition to acrylic acid etc. The α-substituted norbornanyl acrylates are useful as norbornene resist monomers. In the disclosed process, an α-substituted acrylic acid is directly reacted with a substituted norbornene in the presence of at least one acid catalyst selected from methanesulfonic acid and camphorsulfonic acid. It is possible in this reaction to suppress the formation of the by-products derived from intramolecular cyclication, excessive addition of the acid to the reaction product etc.
摘要翻译：公开了在工业规模上有效生产α-取代的降冰片烷基丙烯酸酯的方法，同时抑制由分子内环化衍生的副产物的形成，过度添加到丙烯酸等中。α-取代的降冰片烷基丙烯酸酯可用作降冰片烯抗蚀剂单体。在所公开的方法中，在至少一种选自甲磺酸和樟脑磺酸的酸催化剂的存在下，α-取代的丙烯酸与取代的降冰片烯直接反应。在该反应中可以抑制由分子内环化产生的副产物的形成，向反应产物等过量加入酸。

4. 发明申请

US20090069595A1 Process for Producing Fluorine-Containing Alkylsulfonylaminoethyl Alpha-Substituted Acrylate 有权
标题翻译：制备含氟烷基磺酰基氨基乙基α-取代丙烯酸酯的方法
公开(公告)号：US20090069595A1
公开(公告)日：2009-03-12
申请号：US12187823
申请日：2008-08-07
申请人： Takeo KOMATA , Ryo Nadano , Makoto Matsuura
发明人： Takeo KOMATA , Ryo Nadano , Makoto Matsuura
IPC分类号： C07C221/00
CPC分类号： C07C303/38 , C07C311/09
摘要： There is provided a process for producing a fluorine-containing alkylsulfonylaminoethyl α-substituted acrylate of the formula [3] by reaction of an aminoethyl α-substituted acrylate of the formula [1a] with a fluorine-containing alkylsulfonic fluoride of the formula [2], or by reaction of an aminoethyl a-substituted acrylate salt of the formula [1b] with a fluorine-containing alkylsulfonic fluoride of the formula [2] in the presence of a base, wherein a fluorine-containing compound is used as a reaction solvent: where R1 is a hydrogen atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tertbutyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group or perfluoroethyl group; R2 is a fluorine-containing alkyl group having a carbon number of 1 to 6; Xn− is a counter anion (n is a positive integer); and Y is a fluorine atom, chlorine atom or bromine atom.
摘要翻译：提供了通式[1a]的α-氨基乙基α取代丙烯酸酯与式[2]的含氟烷基磺酸氟化物反应制备式[3]的含氟烷基磺酰氨基乙基α-取代丙烯酸酯的方法，或通过式[1b]的氨基乙基α-取代的丙烯酸盐与式[2]的含氟烷基磺酸氟化物在碱的存在下反应，其中使用含氟化合物作为反应溶剂：其中R1是氢原子，甲基，乙基，正丙基，异丙基，正丁基，仲丁基，叔丁基，氟甲基，二氟甲基，三氟甲基或全氟乙基; R2是碳数为1〜6的含氟烷基; Xn-为抗衡阴离子（n为正整数）; Y是氟原子，氯原子或溴原子。

5. 发明授权

US08466310B2 Process for producing α-substituted norbornanyl acrylates 有权
标题翻译：制备α-取代的降冰片烷基丙烯酸酯的方法
公开(公告)号：US08466310B2
公开(公告)日：2013-06-18
申请号：US13058115
申请日：2009-08-27
申请人： Makoto Matsuura , Ryo Nadano , Takeo Komata
发明人： Makoto Matsuura , Ryo Nadano , Takeo Komata
IPC分类号： C07C67/04 , C07C69/54 , C07B61/00
CPC分类号： C07C67/04 , C07C2602/42 , C07C69/653
摘要： Disclosed is a process for producing α-substituted norbornanyl acrylates efficiently on an industrial scale while suppressing the formation of by-products derived from intramolecular cyclization, excessive addition to acrylic acid etc. The α-substituted norbornanyl acrylates are useful as norbornene resist monomers. In the disclosed process, an α-substituted acrylic acid is directly reacted with a substituted norbornene in the presence of at least one acid catalyst selected from methanesulfonic acid and camphorsulfonic acid. It is possible in this reaction to suppress the formation of the by-products derived from intramolecular cyclication, excessive addition of the acid to the reaction product etc.
摘要翻译：公开了一种在工业规模上有效生产α-取代的降冰片烷基丙烯酸酯的方法，同时抑制由分子内环化衍生的副产物的形成，过度添加到丙烯酸等中。α-取代的降冰片烷基丙烯酸酯可用作降冰片烯抗蚀剂单体。在所公开的方法中，在至少一种选自甲磺酸和樟脑磺酸的酸催化剂存在下，将α-取代的丙烯酸与取代的降冰片烯直接反应。在该反应中可以抑制由分子内环化产生的副产物的形成，向反应产物等过量加入酸。

6. 发明申请

US20050240052A1 Process for producing fluorine-containing alkylsulfonylaminoethyl a-substitued acrylate 有权
标题翻译：含氟烷基磺酰氨基乙基α-取代丙烯酸酯的制备方法
公开(公告)号：US20050240052A1
公开(公告)日：2005-10-27
申请号：US11068824
申请日：2005-03-02
申请人： Takeo Komata , Ryo Nadano , Makoto Matsuura
发明人： Takeo Komata , Ryo Nadano , Makoto Matsuura
IPC分类号： C07C303/38 , C07C311/09 , C07C321/00
CPC分类号： C07C303/38 , C07C311/09
摘要： The present invention provides a process for producing a fluorine-containing alkylsulfonylaminoethyl α-substituted acrylate represented by general formula [3]: which comprises reacting an aminoethyl α-substituted acrylate represented by general formula [1a]or a salt thereof: with a fluorine-containing alkylsulfonyl halide represented by general formula [2a] or a fluorine-containing alkylsulfonic anhydride represented by general formula [2b]: .
摘要翻译：本发明提供由通式[3]表示的含氟烷基磺酰基氨基乙基α-取代丙烯酸酯的制备方法：其包括使通式[1a]表示的α-取代的氨基乙基α-取代的丙烯酸酯或其盐与氟 - 由通式[2a]表示的含烷基磺酰卤或由通式[2b]表示的含氟烷基磺酸酐。

7. 发明申请

US20110237824A1 Process for Producing Fluoroalkylsulfonylaminoethyl Alpha-Substituted-Acrylate 审中-公开
标题翻译：制备氟烷基磺酰氨基乙基α-取代的丙烯酸酯的方法
公开(公告)号：US20110237824A1
公开(公告)日：2011-09-29
申请号：US13131487
申请日：2009-12-22
申请人： Takehisa Ishimaru , Ryo Nadano , Makoto Matsuura
发明人： Takehisa Ishimaru , Ryo Nadano , Makoto Matsuura
IPC分类号： C07C307/02
CPC分类号： C07C303/38 , C07C303/40 , C07C311/09
摘要： Aminoethanol is reacted with a fluoroalkylsulfonic anhydride to obtain a fluoroalkylsulfonylaminoethanol (first step: sulfonylamidation step). The fluoroalkylsulfonylaminoethanol is esterified with an α-substituted acrylate derivative to obtain a desired fluoroalkylsulfonylaminoethyl α-substituted-acrylate (second step: esterification step). Thus, the desired fluoroalkylsulfonylaminoethyl α-substituted-acrylate having a higher purity can be produced in higher yield with higher operating efficiency than in conventional techniques.
摘要翻译：氨基乙醇与氟烷基磺酸酐反应得到氟代烷基磺酰基氨基乙醇（第一步：磺酰胺化步骤）。氟代烷基磺酰基氨基乙醇用α-取代的丙烯酸酯衍生物酯化，得到所需的氟代烷基磺酰基氨基乙基α-取代的丙烯酸酯（第二步：酯化步骤）。因此，与常规技术相比，具有更高纯度的所需氟代烷基磺酰基氨基乙基α-取代的丙烯酸酯可以以更高的产率生产，具有更高的操作效率。

8. 发明授权

US06340776B2 Process for producing 1,1,1-trifluoroacetone 失效
标题翻译：制备1,1,1-三氟丙酮的方法
公开(公告)号：US06340776B2
公开(公告)日：2002-01-22
申请号：US09789001
申请日：2001-02-21
申请人： Yoshihiko Goto , Ryo Nadano , Takashi Sakaya , Takayuki Nishimiya
发明人： Yoshihiko Goto , Ryo Nadano , Takashi Sakaya , Takayuki Nishimiya
IPC分类号： C07C4563
CPC分类号： C07C45/65 , C07C49/167
摘要： A process for producing 1,1,1-trifluoroacetone includes the step of conducting a hydrogenolysis of a halogenated trifluoroacetone, which is represented by the general formula (1), by a hydrogen gas in the presence of a catalyst containing a transition metal, where X represents a chlorine, bromine or iodine, and n represents an integer from 1 to 3. It is possible to obtain 1,1,1-trifluoroacetone with a high yield by using the special catalyst.
摘要翻译：制备1,1,1-三氟丙酮的方法包括在含有过渡金属的催化剂存在下，通过氢气进行由通式（1）表示的卤代三氟丙酮的氢解的步骤，其中 X表示氯，溴或碘，n表示1〜3的整数。通过使用特殊催化剂，可以获得高收率的1,1,1-三氟丙酮。

9. 发明授权

US08524941B2 Process for producing monomer for fluorinated resist 有权
标题翻译：制备氟化抗蚀剂单体的方法
公开(公告)号：US08524941B2
公开(公告)日：2013-09-03
申请号：US13257193
申请日：2010-04-26
申请人： Shinya Akiba , Ryo Nadano , Yutaka Katsuhara
发明人： Shinya Akiba , Ryo Nadano , Yutaka Katsuhara
IPC分类号： C07C69/653
CPC分类号： C07C67/04 , C07C69/653
摘要： According to the present invention, an α-substituted acrylic ester monomer for a fluorinated resist is produced by direct addition of an α-substituted acrylic acid to a fluorinated alkene in the presence of a specific acid catalyst having a sulfonyl group. By the use of such a specific acid catalyst, it is possible to achieve industrial-scale production of the α-substituted acrylic ester monomer for the fluorinated resist by carrying out the target addition reaction of the fluorinated alkene and the α-substituted acrylic acid efficiently during the occurrence of side reactions such as isomerization of the alkene, generation of a diol and excessive addition of the α-substituted acrylic acid.
摘要翻译：根据本发明，通过在具有磺酰基的特定酸催化剂的存在下，直接将α-取代的丙烯酸加入到氟化烯烃中，制备用于氟化抗蚀剂的α-取代的丙烯酸酯单体。通过使用这种特定的酸催化剂，可以通过有效地进行氟化烯烃和α-取代的丙烯酸的目标加成反应来实现氟代抗蚀剂的α-取代的丙烯酸酯单体的工业规模生产在发生副反应如烯烃的异构化，二醇的产生和过量的α-取代的丙烯酸的添加。

10. 发明申请

US20120004444A1 Process for Producing Monomer for Fluorinated Resist 有权
标题翻译：生产氟化抗体单体的方法
公开(公告)号：US20120004444A1
公开(公告)日：2012-01-05
申请号：US13257193
申请日：2010-04-26
申请人： Shinya Akiba , Ryo Nadano , Yutaka Katsuhara
发明人： Shinya Akiba , Ryo Nadano , Yutaka Katsuhara
IPC分类号： C07C67/04
CPC分类号： C07C67/04 , C07C69/653
摘要： According to the present invention, an α-substituted acrylic ester monomer for a fluorinated resist is produced by direct addition of an α-substituted acrylic acid to a fluorinated alkene in the presence of a specific acid catalyst having a sulfonyl group. By the use of such a specific acid catalyst, it is possible to achieve industrial-scale production of the α-substituted acrylic ester monomer for the fluorinated resist by carrying out the target addition reaction of the fluorinated alkene and the α-substituted acrylic acid efficiently during the occurrence of side reactions such as isomerization of the alkene, generation of a diol and excessive addition of the α-substituted acrylic acid.
摘要翻译：根据本发明，通过在具有磺酰基的特定酸催化剂存在下，直接向氟化烯中加入α-取代的丙烯酸，制备用于氟化抗蚀剂的α-取代的丙烯酸酯单体。通过使用这种特定的酸催化剂，可以有效地通过进行氟代烯烃和α-取代的丙烯酸的目标加成反应来实现氟化抗蚀剂的α-取代的丙烯酸酯单体的工业规模生产在发生副反应如烯烃的异构化，二醇的产生和过量的α-取代的丙烯酸的添加。

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