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1. 发明公开

EP1760064A1 METHOD FOR DEUTERATING HALOACRYLIC ACID OR ITS SALT 审中-公开
标题翻译： VERFAHREN ZUR DEUTERIERUNG EINERHALOGENACRYLSÄUREODER EINES SALZES DAVON
公开(公告)号：EP1760064A1
公开(公告)日：2007-03-07
申请号：EP05750962.2
申请日：2005-06-20
申请人： Wako Pure Chemical Industries, Ltd.
发明人： MAESAWA, Tsuneaki , ITO, Nobuhiro , HIROTA, Kosaku , SAJIKI, Hironao
IPC分类号： C07C51/347 , C07B59/00 , C07C57/54 , C07B61/00
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, R 1 and R 2 indicate each independently a light hydrogen atom or a heavy hydrogen atom and at least one of R 1 and R 2 indicates a light hydrogen atom; R 3 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, R 4 and R 5 indicate each independently a light hydrogen atom or a heavy hydrogen atom and at least one of R 4 and R 5 indicates a heavy hydrogen atom; R 3 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有效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，R 1和R 2中的至少一个 2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，其包括在催化剂存在下使通式[1]表示的化合物与重氢源反应，所述催化剂选自钯催化剂，铂催化剂，铑催化剂，钌催化剂，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。

2. 发明公开

EP1882672A1 METHOD FOR PRODUCING DEUTERIUM GAS AND CATALYTIC DEUTERATION METHOD USING DEUTERIUM GAS OBTAINED THEREBY 审中-公开
标题翻译：用于生产氘气AND METHOD FOR接触重氢化用这样得到的氘气LOW
公开(公告)号：EP1882672A1
公开(公告)日：2008-01-30
申请号：EP06711727.5
申请日：2006-01-16
申请人： Wako Pure Chemical Industries, Ltd.
发明人： HIROTA, Kosaku , SAJIKI, Hironao , ITO, Nobuhiro
IPC分类号： C01B4/00 , B01J23/44 , C07B59/00 , C07C51/36 , C07C57/30 , C07C209/36 , C07C211/48
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： [问题]提供一种生产重氢气的方法。这使重氢气从氘化溶剂作为反应底物来有效地生产。 [解决问题的手段（1）一种用于生产重氢气，包括使氘化溶剂与氢气接触压力下在共存与钯催化剂，铂催化剂，镍催化剂，所选择的催化剂的方法钴催化剂与铱催化剂，以及铑催化剂和钌催化剂，其不与配体配位，和（2）的化合物的催化解释定量方法具有还原性官能团，包括使由上述得到的重氢气（1）与具有在共存的还原性官能团的化合物与催化还原催化剂接触。

3. 发明公开

EP1577280A1 METHOD OF DEUTERIZATION 审中-公开
标题翻译：电解法
公开(公告)号：EP1577280A1
公开(公告)日：2005-09-21
申请号：EP03814536.3
申请日：2003-11-07
申请人： Wako Pure Chemical Industries, Ltd.
发明人： ITO, Nobuhiro , MAESAWA, Tsuneaki , MUTO, Kazushige , HIROTA, Kosaku , SAJIKI, Hironao
IPC分类号： C07B59/00 , C07C29/00 , C07C31/02 , C07C35/08 , C07C35/29 , C07C35/37 , C07C45/00 , C07C49/04 , C07C49/08 , C07C49/433 , C07C49/453 , C07C51/00 , C07C53/10 , C07C53/124 , C07C57/04
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]:

R 1 ―X―R 2 [1]

wherein, R 1 represents an alkyl group or an aralkyl group, which may have a carbon-carbon double bond and/or triple bond; R 2 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; R 1 and R 2 may form an alicyclic ring together with a carbon atom contained in X; provided that R 2 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：本发明涉及通式[1]所示化合物的重氢化方法：R 1 -X-R 2 [1]其中，R 1表示可具有碳 - 碳双键的烷基或芳烷基和/或三键; R2表示可具有碳 - 碳双键和/或三键的烷基，芳基，芳烷基，烷氧基，芳氧基或羟基; X代表羰基或羟亚甲基; R1和R2可以与X中含有的碳原子一起形成脂环; 条件是R2表示可具有碳 - 碳双键和/或三键的烷基，当X为羟基亚甲基时为芳基或芳烷基，所述方法包括使通式[1]代表的化合物与在选自钯催化剂，铂催化剂，铑催化剂，钌催化剂，镍催化剂和钴催化剂的活化催化剂的共存下重氢源。本发明的方法可以显着改善工作环境，因为在中性条件下可以在苛刻的条件如碱性条件下执行常规进行的氘化。此外，即使通式[1]所示的化合物为具有碳 - 碳双键或三键的化合物，本发明的重氢化方法也能够在不使所述双键或三重还原的情况下有效地进行目标重氢化键。

4. 发明公开

EP1561741A1 METHOD FOR DEUTERATION OR TRITIATION OF HETEROCYCLIC RING 审中-公开
标题翻译： VERFAHREN ZUR DEUTERIERUNG ODER TRITIIERUNG EINES HETEROCYCLUS
公开(公告)号：EP1561741A1
公开(公告)日：2005-08-10
申请号：EP03811499.7
申请日：2003-11-07
申请人： Wako Pure Chemical Industries, Ltd.
发明人： ITO, Nobuhiro , MAESAWA, Tsuneaki , MUTO, Kazushige , HIROTA, Kosaku , SAJIKI, Hironao
IPC分类号： C07B59/00 , C07D209/08 , C07D209/20 , C07D213/06 , C07D231/12 , C07D233/58 , C07D235/08 , C07D239/47 , C07D239/54 , C07D471/04 , C07D473/30 , C07D473/34 , C07H19/067 , C07H19/167
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溶剂的沸点以上。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易于分解，导致工业和高效氘化具有杂环。

5. 发明公开

EP1535889A1 METHOD OF DEUTERATING AROMATIC RING 审中-公开
标题翻译： VERFAHREN ZUR DEUTERIERUNG AROMATISCHER RINGE
公开(公告)号：EP1535889A1
公开(公告)日：2005-06-01
申请号：EP03771263.5
申请日：2003-07-10
申请人： Wako Pure Chemical Industries, Ltd.
发明人： ITO, Nobuhiro , MAESAWA, Tsuneaki , MUTO, Kazushige , HIROTA, Kosaku , SAJIKI, Hironao
IPC分类号： C07B59/00 , C07C5/00 , C07C15/16 , C07C37/00 , C07C39/04 , C07C39/28 , C07C51/347 , C07C63/06 , C07C63/08 , C07C209/68 , C07C211/46 , C07C217/84 , C07C315/04 , C07C317/14
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：本发明涉及一种使用活化催化剂氘代具有芳环的化合物的方法，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。

6. 发明公开

EP1754739A1 DEUTERATED POLYIMIDES AND DERIVATIVES THEREOF 审中-公开
标题翻译： DEUTERIERTE POLYIMIDE UND DERIVATE DAVON
公开(公告)号：EP1754739A1
公开(公告)日：2007-02-21
申请号：EP05741155.5
申请日：2005-05-17
申请人： Wako Pure Chemical Industries, Ltd.
发明人： MUTO, Kazushige , MAESAWA, Tsuneaki , ITO, Nobuhiro , WATAHIKI, Tsutomu , HIROTA, Kosaku , SAJIKI, Hironao
IPC分类号： C08G73/10 , G02B6/12
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 R 1 indicates a tetravalent alicyclic hydrocarbon group or a tetravalent aromatic hydrocarbon group, which may have a heavy hydrogen atom; R 2 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 R 1 has the same meaning as above, with a deuterated diamine compound represented by the general formula [4]:

H 2 N-R 2 -NH 2 [4]

wherein R 2 has the same meaning as above; a method for producing a deuterated polyimide compound represented by the general formula [1]:

wherein R 1 indicates a tetravalent alicyclic hydrocarbon group or a tetravalent aromatic hydrocarbon group, which may have a heavy hydrogen atom; R 2 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.
摘要翻译：本发明的目的是提供一种可用作光波导聚合物的原料的聚酰亚胺化合物，其具有优异的透明性和耐热性，低吸湿性，小的光学透射损失，高折射率和对基材或基材。本发明是由通式[2]表示的氘代聚酰胺酸化合物的制造方法的发明：其中R 1表示可能具有重氢原子的四价脂环族烃基或四价芳香族烃基; R 2表示具有重氢原子的二价芳香族烃基; m表示不小于1的整数，其包括使通式[3]表示的酸酐与通式[4]表示的氘化二胺化合物反应：其中R 1具有与上述相同的含义。 ƒ€ƒ€ƒ€ƒ€ƒ€ƒ€ƒH2 NR 2 -NH 2€ƒ€ƒ€ƒ€ƒ[4]其中R 2具有与上述相同的含义; 用于制备由通式[1]表示的氘代聚酰亚胺化合物的方法：其中R 1表示可具有重的氢原子的四价脂环族烃基或四价芳族烃基; R 2表示具有重氢原子的二价芳香族烃基; n表示1以上的整数，其包括如此得到的氘代聚酰胺酸化合物进行闭环反应; 一种制备由通式[1]表示的氘代聚酰亚胺化合物的方法，包括使由上述通式[3]表示的酸酐与由上述通式[4]表示的氘化二胺化合物反应，然后使反应产品进行闭环反应; 使用通过上述制备方法获得的氘代聚酰亚胺化合物作为光波导的原料聚合物; 用于包含所述氘代聚酰亚胺化合物的光波导的膜; 氘代聚酰亚胺化合物; 和氘代聚酰胺酸化合物。

7. 发明公开

EP1707548A1 METHOD OF DEUTERATION USING MIXED CATALYST 审中-公开
标题翻译： DEUTERIERUNGSVERFAHREN UNTER ANWENDUNG EINES GEMISCHTEN KATALYSATORS
公开(公告)号：EP1707548A1
公开(公告)日：2006-10-04
申请号：EP04807406.6
申请日：2004-12-21
申请人： Wako Pure Chemical Industries, Ltd.
发明人： ITO, Nobuhiro , MAESAWA, Tsuneaki , MUTO, Kazushige , HIROTA, Kosaku , SAJIKI, Hironao
IPC分类号： C07B59/00 , C07C37/00 , C07C39/06 , C07C51/00 , C07C57/30 , C07C63/04 , C07C211/45 , C07C209/00 , C07D213/803 , C07D213/74
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，其可以以改进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不少于两种选自钯催化剂，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的催化剂。

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