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1. 发明申请

US20060116535A1 Method of deuteration 审中-公开
标题翻译：氘化方法
公开(公告)号：US20060116535A1
公开(公告)日：2006-06-01
申请号：US10539188
申请日：2003-11-07
申请人： Nobuhiro Ito , Tsuneaki Maesawa , Kazushige Muto , Kosaku Hirota , Kosaku Hirota , Hironao Sajiki
发明人： Nobuhiro Ito , Tsuneaki Maesawa , Kazushige Muto , Kosaku Hirota , Kosaku Hirota , Hironao Sajiki
IPC分类号： C07C35/22
CPC分类号： C07B59/00 , C07B2200/05 , C07C29/00 , C07C45/00 , C07C2601/14 , C07C2602/42 , C07C2603/68 , C07C31/125 , C07C35/08 , C07C35/29 , C07C35/37
摘要： 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.
摘要翻译：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

US20080045724A1 Deuterated Polyimides and Derivatives Thereof 审中-公开
公开(公告)号：US20080045724A1
公开(公告)日：2008-02-21
申请号：US11569463
申请日：2005-05-17
申请人： Kazushige Muto , Tsuneaki Maesawa , Nobuhiro Ito , Tsutomu Watahiki , Kosaku Hirota , Hironao Sajiki
发明人： Kazushige Muto , Tsuneaki Maesawa , Nobuhiro Ito , Tsutomu Watahiki , Kosaku Hirota , Hironao Sajiki
IPC分类号： C07C229/54 , C07D487/04
CPC分类号： C07D487/04 , C07D209/48 , C08G73/10 , C08G73/1007 , G02B6/1221
摘要： 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.

3. 发明授权

US08093422B2 Method for deuteration of an aromatic ring 有权
标题翻译：芳环的氘化方法
公开(公告)号：US08093422B2
公开(公告)日：2012-01-10
申请号：US10521531
申请日：2003-07-10
申请人： Nobuhiro Ito , Tsuneaki Maesawa , Kazushige Muto , Kosaku Hirota , Hironao Sajiki
发明人： Nobuhiro Ito , Tsuneaki Maesawa , Kazushige Muto , Kosaku Hirota , Hironao Sajiki
IPC分类号： C07C63/04 , C07C39/28 , C07C13/00
CPC分类号： C07C5/00 , C07B59/00 , C07B59/001 , C07B2200/05 , C07C37/00 , C07C51/00 , C07C51/347 , C07C209/68 , C07C315/04 , C07C63/08 , C07C63/06 , C07C317/14 , C07C211/46 , C07C211/51 , C07C39/04 , C07C39/28
摘要： The present invention relates to a method for deuteration of a compound having an aromatic ring, using an activated catalyst, and the method comprises reacting a compound having an aromatic ring with heavy hydrogen source in the presence of an activated catalyst selected from a platinum catalyst, a rhodium catalyst, a ruthenium catalyst, a nickel catalyst and a cobalt catalyst.
摘要翻译：本发明涉及使用活化催化剂对具有芳香环的化合物进行氘化的方法，该方法包括在活性催化剂存在下使具有芳环的化合物与重氢源反应，所述催化剂选自铂催化剂，铑催化剂，钌催化剂，镍催化剂和钴催化剂。

4. 发明授权

US07517990B2 Method for deuteration of a heterocyclic ring 有权
标题翻译：杂环的氘化方法
公开(公告)号：US07517990B2
公开(公告)日：2009-04-14
申请号：US10534344
申请日：2003-11-07
申请人： Nobuhiro Ito , Tsuneaki Maesawa , Kazushige Muto , Kosaku Hirota , Hironao Sajiki
发明人： Nobuhiro Ito , Tsuneaki Maesawa , Kazushige Muto , Kosaku Hirota , Hironao Sajiki
IPC分类号： C07D295/03 , C07D207/06
CPC分类号： C07D213/16 , C07B59/002 , C07D209/20 , C07D231/12 , C07D233/54 , C07D233/56 , C07D235/06 , C07D239/54 , C07D471/04 , C07D473/30 , C07H19/067 , C07H19/167 , Y02P20/544
摘要： The present invention relates to a method for deuteration of a heterocyclic ring, which comprises subjecting a compound having a heterocyclic ring to sealed refluxing state in a deuterated solvent in the presence of an activated catalyst selected form a palladium catalyst, a platinum catalyst, a rhodium catalyst, a ruthenium catalyst, a nickel catalyst and a cobalt catalyst. In accordance with a method of the present invention, a hydrogen atom belonging to a heterocyclic ring of a compound having a heterocyclic ring can be very efficiently deuterated because temperature of deuteration reaction can be maintained at higher than boiling point of the solvent.Further, a method for deuteration of the present invention can be applied widely to deuteration of various compounds having a heterocyclic ring which are liable to decomposition under supercritical conditions or acidic conditions, leading to industrial and efficient deuteration of a compound having a heterocyclic ring.
摘要翻译：本发明涉及杂环的氘化方法，该方法包括在选自钯催化剂，铂催化剂，铑的活化催化剂的存在下，使具有杂环的化合物在氘代溶剂中密封回流催化剂，钌催化剂，镍催化剂和钴催化剂。根据本发明的方法，具有杂环的化合物的杂环的氢原子可以非常有效地氘化，因为氘代反应的温度可以保持在高于溶剂沸点的温度。此外，本发明的氘化方法可以广泛地应用于具有杂环的各种化合物的猝灭，所述化合物在超临界条件或酸性条件下容易分解，导致具有杂环的化合物的工业和高效氘化。

5. 发明授权

US09255070B2 Method of deuteration using mixed catalyst 有权
标题翻译：使用混合催化剂的氘化方法
公开(公告)号：US09255070B2
公开(公告)日：2016-02-09
申请号：US10585629
申请日：2004-12-21
申请人： Nobuhiro Ito , Tsuneaki Maesawa , Kazushige Muto , Kosaku Hirota , Hironao Sajiki
发明人： Nobuhiro Ito , Tsuneaki Maesawa , Kazushige Muto , Kosaku Hirota , Hironao Sajiki
IPC分类号： C07D213/74 , C07B59/00 , C07C37/00 , C07C51/353 , C07C209/68 , C07D213/80
CPC分类号： C07D213/74 , C07B59/00 , C07B2200/05 , C07C37/00 , C07C51/353 , C07C209/68 , C07D213/80 , C07C57/30 , C07C63/04 , C07C39/06
摘要： The subject of the present invention is to provide a method for deuteration, which can obtain a compound having an aromatic ring and/or a heterocyclic ring at an improved deuteration ratio. The present invention relates to a method for deuteration of a compound having an aromatic ring and/or a heterocyclic ring, comprising reacting the compound having an aromatic ring and/or a heterocyclic ring with a heavy hydrogen source in the presence of an activated mixed catalyst of not less than two kinds of catalysts selected from among a palladium catalyst, a platinum catalyst, a rhodium catalyst, an iridium catalyst, a ruthenium catalyst, a nickel catalyst and a cobalt catalyst.
摘要翻译：本发明的主题是提供一种氘化方法，其可以以改善的氘化比获得具有芳环和/或杂环的化合物。本发明涉及一种具有芳环和/或杂环的化合物的氘化方法，包括在活化的混合催化剂存在下使具有芳环和/或杂环的化合物与重氢源反应选自钯催化剂，铂催化剂，铑催化剂，铱催化剂，钌催化剂，镍催化剂和钴催化剂中的不少于两种催化剂。

6. 发明申请

US20080234488A1 Method of Deuteration Using Mixed Catalyst 有权
标题翻译：使用混合催化剂的氘化方法
公开(公告)号：US20080234488A1
公开(公告)日：2008-09-25
申请号：US10585629
申请日：2004-12-21
申请人： Nobuhiro Ito , Tsuneaki Maesawa , Kazushige Muto , Kosaku Hirota , Hironao Sajiki
发明人： Nobuhiro Ito , Tsuneaki Maesawa , Kazushige Muto , Kosaku Hirota , Hironao Sajiki
IPC分类号： C07C51/00 , C07C209/00 , C07D213/02
CPC分类号： C07D213/74 , C07B59/00 , C07B2200/05 , C07C37/00 , C07C51/353 , C07C209/68 , C07D213/80 , C07C57/30 , C07C63/04 , C07C39/06
摘要： The subject of the present invention is to provide a method for deuteration, which can obtain a compound having an aromatic ring and/or a heterocyclic ring at an improved deuteration ratio. The present invention relates to a method for deuteration of a compound having an aromatic ring and/or a heterocyclic ring, comprising reacting the compound having an aromatic ring and/or a heterocyclic ring with a heavy hydrogen source in the presence of an activated mixed catalyst of not less than two kinds of catalysts selected from among a palladium catalyst, a platinum catalyst, a rhodium catalyst, an iridium catalyst, a ruthenium catalyst, a nickel catalyst and a cobalt catalyst.
摘要翻译：本发明的主题是提供一种氘化方法，其可以以改善的氘化比获得具有芳环和/或杂环的化合物。本发明涉及一种具有芳环和/或杂环的化合物的氘化方法，包括在活化的混合催化剂存在下使具有芳环和/或杂环的化合物与重氢源反应选自钯催化剂，铂催化剂，铑催化剂，铱催化剂，钌催化剂，镍催化剂和钴催化剂中的不少于两种催化剂。

7. 发明申请

US20070255076A1 Method for Deuteration of an Aromatic Ring 有权
标题翻译：芳香环的脱胶方法
公开(公告)号：US20070255076A1
公开(公告)日：2007-11-01
申请号：US10521531
申请日：2003-07-10
申请人： Nobuhiro Ito , Tsuneaki Maesawa , Kazushige Muto , Kosaku Hirota , Hironao Sajiki
发明人： Nobuhiro Ito , Tsuneaki Maesawa , Kazushige Muto , Kosaku Hirota , Hironao Sajiki
IPC分类号： C07B59/00 , C07C315/04 , C07C317/14 , C07C5/10
CPC分类号： C07C5/00 , C07B59/00 , C07B59/001 , C07B2200/05 , C07C37/00 , C07C51/00 , C07C51/347 , C07C209/68 , C07C315/04 , C07C63/08 , C07C63/06 , C07C317/14 , C07C211/46 , C07C211/51 , C07C39/04 , C07C39/28
摘要： The present invention relates to a method for deuteration of a compound having an aromatic ring, using an activated catalyst, and the method comprises reacting a compound having an aromatic ring with heavy hydrogen source in the presence of an activated catalyst selected from a platinum catalyst, a rhodium catalyst, a ruthenium catalyst, a nickel catalyst and a cobalt catalyst.
摘要翻译：本发明涉及使用活化催化剂对具有芳香环的化合物进行氘化的方法，该方法包括在活性催化剂存在下使具有芳环的化合物与重氢源反应，所述催化剂选自铂催化剂，铑催化剂，钌催化剂，镍催化剂，钴催化剂等。

8. 发明申请

US20060025596A1 Method for deuteration or tritiation of heterocyclic ring 有权
标题翻译：杂环氘化或氚化的方法
公开(公告)号：US20060025596A1
公开(公告)日：2006-02-02
申请号：US10534344
申请日：2003-11-07
申请人： Nobuhiro Ito , Tsuneaki Maesawa , Kazushige Muto , Kosaku Hirota , Hironao Sajiki
发明人： Nobuhiro Ito , Tsuneaki Maesawa , Kazushige Muto , Kosaku Hirota , Hironao Sajiki
IPC分类号： C07D211/00 , C07D207/00 , C07D205/00 , C07D203/04
CPC分类号： C07D213/16 , C07B59/002 , C07D209/20 , C07D231/12 , C07D233/54 , C07D233/56 , C07D235/06 , C07D239/54 , C07D471/04 , C07D473/30 , C07H19/067 , C07H19/167 , Y02P20/544
摘要： The present invention relates to a method for deuteration of a heterocyclic ring, which comprises subjecting a compound having a heterocyclic ring to sealed refluxing state in a deuterated solvent in the presence of an activated catalyst selected form a palladium catalyst, a platinum catalyst, a rhodium catalyst, a ruthenium catalyst, a nickel catalyst and a cobalt catalyst. In accordance with a method of the present invention, a hydrogen atom belonging to a heterocyclic ring of a compound having a heterocyclic ring can be very efficiently deuterated because temperature of deuteration reaction can be maintained at higher than boiling point of the solvent. Further, a method for deuteration of the present invention can be applied widely to deuteration of various compounds having a heterocyclic ring which are liable to decomposition under supercritical conditions or acidic conditions, leading to industrial and efficient deuteration of a compound having a heterocyclic ring.
摘要翻译：本发明涉及杂环的氘化方法，该方法包括在选自钯催化剂，铂催化剂，铑的活化催化剂的存在下，使具有杂环的化合物在氘代溶剂中密封回流催化剂，钌催化剂，镍催化剂和钴催化剂。根据本发明的方法，具有杂环的化合物的杂环的氢原子可以非常有效地氘化，因为氘代反应的温度可以保持在高于溶剂沸点的温度。此外，本发明的氘化方法可以广泛地应用于具有杂环的各种化合物的猝灭，所述化合物在超临界条件或酸性条件下容易分解，导致具有杂环的化合物的工业和高效氘化。

9. 发明申请

US20080071107A1 Method for Deuterating Haloacrylic Acid or its Salt 审中-公开
标题翻译：卤代丙烯酸或其盐的氘化方法
公开(公告)号：US20080071107A1
公开(公告)日：2008-03-20
申请号：US11630075
申请日：2005-06-20
申请人： Tsuneaki Maesawa , Nobuhiro Ito , Kosaku Hirota , Hironao Sajiki
发明人： Tsuneaki Maesawa , Nobuhiro Ito , Kosaku Hirota , Hironao Sajiki
IPC分类号： C07C69/63
CPC分类号： C07B59/001 , C07B2200/05 , C07C51/347 , C07C57/54
摘要： 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.
摘要翻译：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。

10. 发明申请

US20080145303A1 Method for Producing Deuterium Gas and Catalytic Deuteration Method Using Deuterium Gas Obtained Thereby 审中-公开
标题翻译：使用由此获得的氘气生产氘气和催化氘化方法
公开(公告)号：US20080145303A1
公开(公告)日：2008-06-19
申请号：US11883193
申请日：2006-01-16
申请人： Kosaku Hirota , Hironao Sajiki , Nobuhiro Ito
发明人： Kosaku Hirota , Hironao Sajiki , Nobuhiro Ito
IPC分类号： C01B4/00 , C01B7/00 , C07D301/00 , C07C255/00 , C07C211/00 , C07C39/00 , C07C5/08 , C07C5/02
CPC分类号： C07C209/36 , B01J21/18 , B01J23/42 , B01J23/44 , B01J23/46 , B01J23/75 , B01J23/755 , C01B4/00 , C07B59/00 , C07B2200/05 , C07C57/30 , C07C209/48 , C07C211/46 , C07C211/48
摘要： [PROBLEMS] To provide a method for producing heavy hydrogen gas, which enables heavy hydrogen gas to be efficiently produced from a deuterated solvent as a reaction substrate.[MEANS FOR SOLVING PROBLEMS] (1) A method for producing heavy hydrogen gas, comprising bringing a deuterated solvent into contact with hydrogen gas under pressure in the coexistence with a catalyst selected from a palladium catalyst, a platinum catalyst, a nickel catalyst, a cobalt catalyst, an iridium catalyst, and a rhodium catalyst and a ruthenium catalyst which are not coordinated with a ligand, and (2) a catalytic deuteration method of a compound having a reducible functional group, comprising bringing the heavy hydrogen gas obtained by the above (1) into contact with the compound having a reducible functional group in the coexistence with a catalytic reduction catalyst.
摘要翻译：本发明提供一种生产重氢气的方法，其能够使重氢气从氘化溶剂作为反应基质有效地生成。（1）一种重氢气的制造方法，其特征在于，在与钯催化剂，铂催化剂，镍催化剂，镍催化剂等的催化剂共存的同时使氘化溶剂与氢气接触，钴催化剂，铱催化剂以及不与配位体配位的铑催化剂和钌催化剂，（2）具有可还原官能团的化合物的催化氘化方法，其特征在于，将上述得到的重氢气（1）在与催化还原催化剂共存的情况下与具有可还原官能团的化合物接触。

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