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1. 发明授权

US07122676B2 Process for the preparation of 5,5′-bi-1H-tetrazolediammonium salts using hydrazine hydrate and dicyan as starting materials 失效
标题翻译：使用水合肼和二氰作为原料制备5,5'-双-1,5-四唑基铵盐的方法
公开(公告)号：US07122676B2
公开(公告)日：2006-10-17
申请号：US09813826
申请日：2001-03-22
申请人： Shunji Hyoda , Masaharu Kita , Hirotoshi Sawada , Shuichi Nemugaki , Takahiro Ueta , Kohki Satoh
发明人： Shunji Hyoda , Masaharu Kita , Hirotoshi Sawada , Shuichi Nemugaki , Takahiro Ueta , Kohki Satoh
IPC分类号： C07D257/04 , B01J19/00
CPC分类号： C07D257/04 , C07C257/22
摘要： A process for preparing 5,5′-bi-1H-tetrazolediammonium salts (BHT.2NH3) maintaining a high yield through oxaldiimidic acid dihydrazide (OAH) from the starting materials which are cheaply available and are easy to handle. The 5,5′-bi-1H-tetrazolediammonium salts (BHT.2NH3) are prepared by dissolving the oxaldiimidic acid dihydrazide (OAH) obtained by the reaction of hydrated hydrazide with dicyan in an aqueous solution of a weakly acidic compound such as acetic acid, dropwisely adding an aqueous solution of sodium nitrite thereto to form an azide thereof and to effect the cyclization reaction by heating, adding an aqueous solution of sodium hydroxide to the reaction product to convert it into a 5,5′-bi-1H-tetrazoledisodium salt (BHT.2Na), reacting it with an aqueous solution of ammonium chloride, and recovering the formed ammonium salt as sparingly soluble crystals.
摘要翻译：通过草本二酰亚胺二酰肼（OAH）从起始原料中制备的5,5'-双-1,5-四唑基铵盐（BHT.2NH 3 N 3）的方法，该方法是廉价可得的并且容易处理。通过将通过水合酰肼与二氰反应得到的草二酰亚胺二酰肼（OAH）溶解在水溶液中，制备5,5'-双-1H-四唑基铵盐（BHT.2NH 3 N 3）弱酸性化合物如乙酸，向其中逐滴加入亚硝酸钠水溶液形成叠氮化物，通过加热进行环化反应，向反应产物中加入氢氧化钠水溶液，将其转化为5， 5'-双-1,5-四唑基二钠盐（BHT.2Na），与氯化铵水溶液反应，回收形成的铵盐作为微溶晶体。

2. 发明授权

US6156906A Process for the preparation of 5,5'-bi-1H-tetrazole salt 失效
标题翻译：制备5,5'-双-1H-四唑盐的方法
公开(公告)号：US6156906A
公开(公告)日：2000-12-05
申请号：US374949
申请日：1999-08-16
申请人： Shunji Hyoda , Masaharu Kita , Hirotoshi Sawada , Shuichi Nemugaki , Takahiro Ueta , Kohki Satoh , Sumio Otsuka , Yoshitaka Miyawaki , Hiroshi Taniguchi
发明人： Shunji Hyoda , Masaharu Kita , Hirotoshi Sawada , Shuichi Nemugaki , Takahiro Ueta , Kohki Satoh , Sumio Otsuka , Yoshitaka Miyawaki , Hiroshi Taniguchi
IPC分类号： C07D257/04 , C07D403/04
CPC分类号： C07D257/04
摘要： A process for the preparation of a 5,5'-bi-1H-tetrazole diammonium salt by dropwisely adding the aqueous hydrogen peroxide to which a small amount of weakly acidic substance has been added, to a starting aqueous solution containing hydrogen cyanide or sodium cyanide or potassium cyanide, sodium azide and a catalytic amount of copper sulfate preferably at a low temperature to maintain the pH of the reaction solution over a range of from 5 to 6, heating the reaction solution to effect the oxidation and cyclization reaction, reacting the reaction product with ammonium chloride or an aqueous solution thereof, and recovering the formed ammonium salt in the form of sparingly soluble crystals. The desired product is obtained in a high yield and in a high purity from the starting materials which are cheaply available and are easy to handle through a decreased number of steps, i.e., through a one-pot reaction without requiring cumbersome after-treatment.
摘要翻译：通过向含有氰化氢或氰化钠的起始水溶液中滴加加入少量弱酸性物质的过氧化氢水溶液来制备5,5'-双-1H-四唑二铵盐的方法或氰化钾，叠氮化钠和催化量的硫酸铜，优选在低温下将反应溶液的pH维持在5至6的范围内，加热反应溶液进行氧化和环化反应，使反应与氯化铵或其水溶液反应，并回收形成的微溶晶体形式的铵盐。从廉价可得的起始原料以高产率和高纯度获得所需的产物，并且通过减少数量的步骤，即通过一锅反应而不需要繁琐的后处理容易处理。

3. 发明授权

US6040453A Method for preparing 5,5'-bi-1H-tetrazole salt 失效
标题翻译：制备5,5'-双-1H-四唑盐的方法
公开(公告)号：US6040453A
公开(公告)日：2000-03-21
申请号：US374950
申请日：1999-08-16
申请人： Shunji Hyoda , Masaharu Kita , Hirotoshi Sawada , Shuichi Nemugaki , Sumio Otsuka , Yoshitaka Miyawaki , Takashi Ogawa , Yuhki Kubo
发明人： Shunji Hyoda , Masaharu Kita , Hirotoshi Sawada , Shuichi Nemugaki , Sumio Otsuka , Yoshitaka Miyawaki , Takashi Ogawa , Yuhki Kubo
IPC分类号： C07D257/04 , C07D403/04
CPC分类号： C07D257/04
摘要： A process for the preparation of a 5,5'-bi-1H-tetrazole diammonium salt by using dicyan, sodium azide, ammonium chloride and water as a reaction medium. This process is industrially advantageous since the 5,5'-bi-1H-tetrazole diammonium salt is synthesized and, then, the precipitated crystals thereof are simply isolated by filtration to obtain the 5,5'-bi-1H-tetrazole diammonium salt maintaining an yield which is not lower than 90%. The 5,5'-bi-1H-tetrazole diammonium salt is a gas-generating agent for air bags, which is lowly toxic and is easy to handle.
摘要翻译：通过使用二氰，叠氮化钠，氯化铵和水作为反应介质制备5,5'-双-1,5-四唑二铵盐的方法。该方法在工业上是有利的，因为合成了5,5'-双-1,5-四唑二铵盐，然后通过过滤简单地分离其沉淀的晶体，得到5,5'-双-1,5-四唑二铵盐保持产率不低于90％。 5,5'-双-1,5-四唑二铵盐是气囊的气体发生剂，其毒性低，易于处理。

4. 发明授权

US06433181B1 Process for the preparation of highly pure 5,5′-bi-1H-tetrazolediammonium salts 失效
标题翻译：制备高纯度5,5'-双-1,5-四唑基铵盐的方法
公开(公告)号：US06433181B1
公开(公告)日：2002-08-13
申请号：US09871946
申请日：2001-06-04
申请人： Shunji Hyoda , Masaharu Kita , Atsushi Sugino , Shuichi Nemugaki , Takahiro Ueta , Koki Sato
发明人： Shunji Hyoda , Masaharu Kita , Atsushi Sugino , Shuichi Nemugaki , Takahiro Ueta , Koki Sato
IPC分类号： C07D25704
CPC分类号： C07D257/04
摘要： A process for the preparation of a highly pure 5,5′-bi-1H-tetrazolediammonium salt comprising adding a small amount of ammonia water to a reaction solution containing a 5,5′-bi-1H-tetrazolediammonium salt synthesized in the presence of a copper catalyst, removing by filtration the blue insoluble components of formed copper.ammonia.5,5′-bi-1H-tetrazole complex to obtain a filtrate of the 5,5′-bi-1H-tetrazoledisodium salt and reacting the filtrate with an aqueous solution of ammonium chloride, and recovering the formed, highly pure ammonium salt as sparingly soluble crystals.
摘要翻译：一种制备高纯度5,5'-双-1,5-四唑基铵盐的方法，包括向含有5,5'-双-1,5-四唑基铵盐的反应溶液中加入少量氨水，该反应溶液在铜催化剂，通过过滤除去形成的铜五氢-5,5'-双-1,5-四唑络合物的蓝色不溶性组分，得到5,5'-双-1,5-四唑基二钠盐的滤液，并将滤液与氯化铵水溶液，并回收形成的高纯度铵盐作为微溶晶体。

5. 发明授权

US5977360A Process for producing cyclic hydrazine derivatives, tetra-hydropyridazine and hexahydropyridazine 失效
标题翻译：环肼衍生物，四氢哒嗪和六氢哒嗪的制备方法
公开(公告)号：US5977360A
公开(公告)日：1999-11-02
申请号：US998168
申请日：1997-12-24
申请人： Youichi Hasegawa , Shunji Hyoda , Hiroyuki Fujita , Hirotoshi Sawada , Yasuo Oki
发明人： Youichi Hasegawa , Shunji Hyoda , Hiroyuki Fujita , Hirotoshi Sawada , Yasuo Oki
IPC分类号： C07D237/04 , C07D295/30 , C07D487/04 , C07D237/02 , C07D241/02
CPC分类号： C07D295/30 , C07D237/04 , C07D487/04
摘要： The present invention relates to a process for producing alicyclic hydrazine derivatives, tetrahydropyridazine and hexahydropyridazine which are useful as intermediate starting materials such as medicines and agricultural chemicals. Especially, the present invention provides;a process for producing an alicyclic hydrazine derivative or its hydrohalogenic acid salt, which comprises reacting a hydrazine hydrohalogenic acid salt with a diol compound or an alicyclic ether compound in the presence of an excessive inorganic acid existing in a free form or in the form of an acid addition salt;a process for producing tetrahydropyridazine from 1-aminopyrrolidine, which comprises oxidizing 1-aminopyrrolidine with an oxidizing agent to form tetrahydropyridazine; anda process for producing hexahydropyridazine, which comprises oxidizing 1-aminopyrrolidine with an oxidizing agent, synthesizing tetrahydropyridazine, and thereafter, hydrogenating the tetrahydropyridazine in the presence of a base.
摘要翻译：本发明涉及可用作中间起始物质如药物和农药的脂环肼衍生物，四氢哒嗪和六氢哒嗪的生产方法。特别地，本发明提供：一种生产脂环肼衍生物或其氢卤酸盐的方法，其包括在存在过量无机酸的情况下使肼氢卤酸盐与二醇化合物或脂环族醚化合物反应，或者以酸加成盐; 由1-氨基吡咯烷生产四氢哒嗪的方法，其中包括用氧化剂氧化1-氨基吡咯烷以形成四氢哒嗪; 以及制备六氢哒嗪的方法，其包括用氧化剂氧化1-氨基吡咯烷，合成四氢哒嗪，然后在碱的存在下氢化四氢哒嗪。

6. 发明授权

US06194577B1 Process for producing alicyclic hydrazine derivatives, tetra-hydropyridazine and hexahydropyridazine 有权
标题翻译：制备脂环肼衍生物，四氢哒嗪和六氢哒嗪的方法
公开(公告)号：US06194577B1
公开(公告)日：2001-02-27
申请号：US09337607
申请日：1999-06-21
申请人： Youichi Hasegawa , Shunji Hyoda , Hiroyuki Fujita , Hirotoshi Sawada , Yasuo Oki
发明人： Youichi Hasegawa , Shunji Hyoda , Hiroyuki Fujita , Hirotoshi Sawada , Yasuo Oki
IPC分类号： C07D23704
CPC分类号： C07D295/30 , C07D237/04 , C07D487/04
摘要： The present invention relates to a process for producing alicyclic hydrazine derivatives, tetrahydropyridazine and hexahydropyridazine which are useful as intermediate starting materials such as medicines and agricultural chemicals. Especially, the present invention provides; a process for producing an alicyclic hydrazine derivative or its hydrohalogenic acid salt, which comprises reacting a hydrazine hydrohalogenic acid salt with a doil compound or an alicyclic ether compound in the presence of an excessive inorganic acid existing in a free form or in the form of an acid addition salt; a process for producing tetrahydropyridazine from 1-aminopyrrolidine, which comprises oxidizing 1-aminopyrrolidine with an oxidizing agent to form tetrahydropyridazine; and a process for producing hexahydropyridazine, which comprises oxidizing 1-aminopyrrolidine with an oxidizing agent, synthesizing tetrahydropyridazine, and thereafter, hydrogenating the tetrahydropyridazine in the presence of a base.
摘要翻译：本发明涉及可用作中间起始物质如药物和农药的脂环肼衍生物，四氢哒嗪和六氢哒嗪的生产方法。特别地，本发明提供了一种制备脂环肼衍生物或其氢卤酸盐的方法，该方法包括在存在无机酸的过量无机酸的存在下，使肼氢卤酸盐与多西尔化合物或脂环族醚化合物反应形式或以酸加成盐的形式;由1-氨基吡咯烷生产四氢哒嗪的方法，其包括用氧化剂氧化1-氨基吡咯烷以形成四氢哒嗪; 以及制备六氢哒嗪的方法，其包括用氧化剂氧化1-氨基吡咯烷，合成四氢哒嗪，然后在碱的存在下氢化四氢哒嗪。

7. 发明授权

US5618978A Method of producing choline of a high purity 失效
标题翻译：生产高纯度胆碱的方法
公开(公告)号：US5618978A
公开(公告)日：1997-04-08
申请号：US622082
申请日：1996-03-26
申请人： Shunji Hyoda , Youichi Hasegawa , Fumio Toda
发明人： Shunji Hyoda , Youichi Hasegawa , Fumio Toda
IPC分类号： C07C213/08 , C07C213/10 , C07C215/40 , C25B3/00 , C07C209/84
CPC分类号： C07C213/10 , C25B3/00
摘要： A method of producing a choline having a high purity without containing by-products by using a molecule-inclusion complex of the choline as a starting material. A choline inclusion complex without containing by-products is obtained by reacting an aqueous solution of the choline containing, as by-products, those cholines to which are added ethylene oxides with host molecules such as of 1,1'-bis-.beta.-naphthol, and is further reacted with a carbon dioxide gas in order to obtain an aqueous solution of a choline carbonate and/or a choline bicarbonate of a high purity, which is then subjected to the electrolysis using a cation-exchange membrane as a diaphragm, in order to obtain an aqueous solution of the choline of a high purity without containing by-products. The choline that is obtained is a strongly basic compound having a high purity and is very useful as a photoresist-developing solution.
摘要翻译：通过使用胆碱的分子包合配合物作为起始原料，生产具有高纯度而不含有副产物的胆碱的方法。不含有副产物的胆碱包合络合物通过将含有作为副产物的胆碱的水溶液与添加有环氧乙烷的主链分子例如1,1'-双-β-萘酚并进一步与二氧化碳气体反应，以获得高纯度的碳酸胆碱和/或胆碱碳酸氢盐的水溶液，然后使用阳离子交换膜作为隔膜进行电解，以获得高纯度的胆碱水溶液而不含副产物。获得的胆碱是具有高纯度的强碱性化合物，并且作为光致抗蚀剂显影溶液是非常有用的。

8. 发明授权

US5731465A Process for the preparation of tertiary butyl hydrazine hydrohalogenide 失效
标题翻译：叔丁基肼氢卤化物的制备方法
公开(公告)号：US5731465A
公开(公告)日：1998-03-24
申请号：US747002
申请日：1996-11-07
申请人： Yoichi Hasegawa , Mineo Nakagawa , Shunji Hyoda , Hiroyuki Fujita , Takafumi Kawada
发明人： Yoichi Hasegawa , Mineo Nakagawa , Shunji Hyoda , Hiroyuki Fujita , Takafumi Kawada
IPC分类号： C07C241/02 , C07C243/14
CPC分类号： C07C241/02
摘要： An industrially and economically advantageous process for the preparation of a TBH-HX using starting materials which are cheaply available and are easy to handle, maintaining a high yield. A tertiary butyl hydrazine hydrohalogenide is prepared by reacting a hydrazine hydrohalogenide with a methyl tertiary butyl ether in the presence of an acid.
摘要翻译：在工业和经济上有利的制备TBH-HX的方法，其使用廉价可用且易于处理的起始材料，保持高产率。通过在酸的存在下使氢卤酸肼与甲基叔丁基醚反应来制备氢化四氢化叔丁基肼。

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