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    • 1. 发明申请
    • Method of deuteration
    • 氘化方法
    • US20060116535A1
    • 2006-06-01
    • US10539188
    • 2003-11-07
    • Nobuhiro ItoTsuneaki MaesawaKazushige MutoKosaku HirotaKosaku HirotaHironao Sajiki
    • Nobuhiro ItoTsuneaki MaesawaKazushige MutoKosaku HirotaKosaku HirotaHironao Sajiki
    • C07C35/22
    • C07B59/00C07B2200/05C07C29/00C07C45/00C07C2601/14C07C2602/42C07C2603/68C07C31/125C07C35/08C07C35/29C07C35/37
    • The present invention relates to a method for deuteration of a compound represented by the general formula [1]: R1—X—R2  [1] wherein, R1 represents an alkyl group or an aralkyl group, which may have a carbon-carbon double bond and/or triple bond; R2 represents an alkyl group which may have a carbon-carbon double bond and/or triple bond, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group or a hydroxyl group; X represents a carbonyl group or a hydroxylmethylene group, R1 and R2 may form an alicyclic ring together with a carbon atom contained in X; provided that R2 represents an alkyl group which may have a carbon-carbon double bond and/or triple bond, an aryl group or an aralkyl group when X is a hydroxylmethylene group, comprising reacting the compound represented by the general formula [1] with a heavy hydrogen source in the co-presence of an activated catalyst selected from a palladium catalyst, a platinum catalyst, a rhodium catalyst, a ruthenium catalyst, a nickel catalyst and a cobalt catalyst. The method of the present invention can significantly improve working environment because the deuteration, which has been conventionally carried out under severe conditions such as basic condition, can be carried out under neutral condition. Further, even when the compound represented by the general formula [1] is one having a carbon-carbon double bond or triple bond, the method for deuteration of the present invention enables to efficiently carry out objective deuteration without reduction of said double bond or triple bond.
    • 本发明涉及由通式[1]表示的化合物的氘化方法:<?in-line-formula description =“In-line Formulas”end =“lead”?> R&lt; 1& SUP> -XR <2> <1 in-line-formula description =“In-line Formulas”end =“tail”?>其中,R 1表示 烷基或芳烷基,其可以具有碳 - 碳双键和/或三键; R 2表示可以具有碳 - 碳双键和/或三键,芳基,芳烷基,烷氧基,芳氧基或羟基的烷基; X表示羰基或羟基亚甲基,R 1和R 2可以与X中包含的碳原子一起形成脂环族环; 条件是当X是羟基亚甲基时,R 2表示可以具有碳 - 碳双键和/或三键的烷基,芳基或芳烷基,包括使由 在活性催化剂共催化剂中选择钯催化剂,铂催化剂,铑催化剂,钌催化剂,镍催化剂和钴催化剂,具有重氢源的通式[1]。 本发明的方法可以显着地改善工作环境,因为通常在诸如碱性条件的苛刻条件下常规进行的氘化可以在中性条件下进行。 此外,即使当由通式[1]表示的化合物是具有碳 - 碳双键或三键的化合物时,本发明的氘化方法能够有效地进行目标氘化而不会减少所述双键或三重键 键。
    • 2. 发明申请
    • Deuterated Polyimides and Derivatives Thereof
    • US20080045724A1
    • 2008-02-21
    • US11569463
    • 2005-05-17
    • Kazushige MutoTsuneaki MaesawaNobuhiro ItoTsutomu WatahikiKosaku HirotaHironao Sajiki
    • Kazushige MutoTsuneaki MaesawaNobuhiro ItoTsutomu WatahikiKosaku HirotaHironao Sajiki
    • C07C229/54C07D487/04
    • C07D487/04C07D209/48C08G73/10C08G73/1007G02B6/1221
    • The object of the present invention is to provide a polyimide compound useful as a raw material of a polymer for an optical waveguide that has excellent transparency and heat resistance, low moisture absorption, a small optical transmission loss, a high refractive index and good adhesion to a base material or a substrate. The present invention is inventions of a method for producing a deuterated polyamic acid compound represented by the general formula [2]: wherein R1 indicates a tetravalent alicyclic hydrocarbon group or a tetravalent aromatic hydrocarbon group, which may have a heavy hydrogen atom; R2 indicates a divalent aromatic hydrocarbon group having a heavy hydrogen atom; and m indicates an integer not less than 1, which comprises reacting an acid anhydride represented by the general formula [3]: wherein R1 has the same meaning as above, with a deuterated diamine compound represented by the general formula [4]: H2N—R2—NH2  [4] wherein R2 has the same meaning as above; a method for producing a deuterated polyimide compound represented by the general formula [1]: wherein R1 indicates a tetravalent alicyclic hydrocarbon group or a tetravalent aromatic hydrocarbon group, which may have a heavy hydrogen atom; R2 indicates a divalent aromatic hydrocarbon group having a heavy hydrogen atom; and n indicates an integer not less than 1, which comprises subjecting thus obtained deuterated polyamic acid compound to a ring closure reaction; a method for producing a deuterated polyimide compound represented by the general formula [1] which comprises reacting an acid anhydride represented by the above general formula [3] with a deuterated diamine compound represented by the above general formula [4] and then subjecting the reaction product to a ring closure reaction; use of a deuterated polyimide compound obtained by the above production methods as a raw material polymer for an optical waveguide; a film for an optical waveguide containing said deuterated polyimide compound; a deuterated polyimide compound; and a deuterated polyamic acid compound.
    • 9. 发明申请
    • Method for Deuterating Haloacrylic Acid or its Salt
    • 卤代丙烯酸或其盐的氘化方法
    • US20080071107A1
    • 2008-03-20
    • US11630075
    • 2005-06-20
    • Tsuneaki MaesawaNobuhiro ItoKosaku HirotaHironao Sajiki
    • Tsuneaki MaesawaNobuhiro ItoKosaku HirotaHironao Sajiki
    • C07C69/63
    • C07B59/001C07B2200/05C07C51/347C07C57/54
    • The object of the present invention is to provide a method for efficiently and industrially deuterating a haloacrylic acid or salt thereof. The present invention is an invention of a deuteration method of a compound represented by the general formula [1]: wherein, R1 and R2 indicate each independently a light hydrogen atom or a heavy hydrogen atom and at least one of R1 and R2 indicates a light hydrogen atom; R3 indicates a light hydrogen atom, a heavy hydrogen atom, an alkaline metal atom or an alkaline earth metal atom; X indicates a halogen atom; and n indicates 1 or 2, which comprises reacting the compound represented by the general formula [1] with a heavy hydrogen source in the presence of a catalyst selected from a palladium catalyst, a platinum catalyst, a rhodium catalyst, a ruthenium catalyst, a nickel catalyst and a cobalt catalyst that are not subjected to activation processing; and an invention of a deuterated compound represented by the general formula [2]: wherein, R4 and R5 indicate each independently a light hydrogen atom or a heavy hydrogen atom and at least one of R4 and R5 indicates a heavy hydrogen atom; R3 indicates a light hydrogen atom, a heavy hydrogen atom, an alkaline metal atom or an alkaline earth metal atom; X indicates a halogen atom; and n indicates 1 or 2.
    • 本发明的目的是提供一种用于有效地和工业上氘化卤代丙烯酸或其盐的方法。 本发明是由通式[1]表示的化合物的氘代方法的发明:其中R 1和R 2各自独立地表示轻氢原子 或重氢原子,并且R 1和R 2中的至少一个表示轻氢原子; R 3表示轻氢原子,重氢原子,碱金属原子或碱土金属原子; X表示卤素原子; n表示1或2,它包括在选自钯催化剂,铂催化剂,铑催化剂,钌催化剂,钌催化剂的催化剂存在下使由通式[1]表示的化合物与重氢源反应 镍催化剂和不经过活化处理的钴催化剂; 和由通式[2]表示的氘代化合物的发明:其中R 4和R 5各自独立地表示轻氢原子或重氢原子, R 4和R 5中的至少一个表示重氢原子; R 3表示轻氢原子,重氢原子,碱金属原子或碱土金属原子; X表示卤素原子; n表示1或2。