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1. 发明授权

US4571437A Process for preparing p-aminophenol and alkyl substituted p-aminophenol 失效
标题翻译：制备对氨基苯酚和烷基取代的对氨基苯酚的方法
公开(公告)号：US4571437A
公开(公告)日：1986-02-18
申请号：US516857
申请日：1983-07-25
申请人： Douglas C. Caskey , Douglas W. Chapman
发明人： Douglas C. Caskey , Douglas W. Chapman
IPC分类号： C07C215/76 , C07C89/00
CPC分类号： C07C215/76 , Y02P20/582
摘要： A process for preparing unsubstituted and alkyl substituted p-aminophenols. A charge mixture is prepared comprising an unsubstituted or alkyl substituted nitrobenzene, a highly dissociated acid, a catalyst containing platinum and a divalent sulfur compound in which sulfur is bonded to two other moieties, the sulfur compound being present in a proportion of between about 0.1 and about 100 moles per gram-atom of platinum. The mixture comprises an organic phase containing the substrate and an aqueous phase containing the acid. Hydrogen is introduced into the mixture at a pressure of 0-50 psig while the mixture is agitated at a temperature of 70.degree. C. to 100.degree. C., thereby causing the substrate to be reduced to phenylhydroxylamine or an alkyl substituted phenylhydroxylamine. The hydroxylamine is rearranged in the presence of acid to the substituted or unsubstituted p-aminophenol, which is recovered from the aqueous phase.
摘要翻译：一种制备未取代和烷基取代的对氨基苯酚的方法。制备包含未取代或烷基取代的硝基苯，高度离解的酸，含有铂的催化剂和其中硫与两个其它部分结合的二价硫化合物的电荷混合物，所述硫化合物以约0.1和每克原子铂约100摩尔。混合物包含含有底物的有机相和含有酸的水相。在0-50psig的压力下将氢气引入混合物中，同时将混合物在70℃至100℃的温度下搅拌，由此使底物还原成苯基羟胺或烷基取代的苯基羟胺。在酸存在下将羟胺重排为取代或未取代的对氨基苯酚，其从水相中回收。

2. 发明授权

US4415753A Process for preparing p-aminophenol and alkyl substituted p-aminophenol 失效
标题翻译：制备对氨基苯酚和烷基取代的对氨基苯酚的方法
公开(公告)号：US4415753A
公开(公告)日：1983-11-15
申请号：US343993
申请日：1982-01-29
申请人： Douglas C. Caskey , Douglas W. Chapman
发明人： Douglas C. Caskey , Douglas W. Chapman
IPC分类号： C07B61/00 , B01J23/00 , C07C67/00 , C07C213/00 , C07C215/76 , C07C85/11 , C07C89/00
CPC分类号： C07C215/76
摘要： A process for the production of unsubstituted and lower alkyl substituted p-aminophenols. A charge mixture is prepared comprising an unsubstituted or lower alkyl substituted nitrobenzene substrate, a platinum catalyst and a sulfur compound. The sulfur compound may be a divalent sulfur compound in which sulfur is bonded to two other moieties or a compound reducible to such sulfur compound under catalytic hydrogenation conditions. Hydrogen is introduced into the mixture while it is agitated at a temperature of 0.degree.-40.degree. C., thereby reducing the substrate to an unsubstituted or alkyl substituted phenylhydroxylamine. The hydroxylamine is thereafter heated to a temperature of at least 70.degree. C. and agitated at at least 70.degree. C. in the presence of a highly dissociated acid, thereby effecting rearrangement of the hydroxylamine to the corresponding p-aminophenol.
摘要翻译：一种制备未取代和低级烷基取代的对氨基苯酚的方法。制备包含未取代或低级烷基取代的硝基苯底物，铂催化剂和硫化合物的电荷混合物。硫化合物可以是二价硫化合物，其中硫在催化氢化条件下结合到两个其它部分或可还原成这种硫化合物的化合物。将氢气在0℃-40℃的温度下搅拌引入混合物中，从而将底物还原成未取代或烷基取代的苯基羟胺。然后将羟胺加热至至少70℃的温度，并在高度离解的酸存在下在至少70℃下搅拌，从而实现羟胺重排为相应的对氨基苯酚。

3. 发明授权

US4970332A Process for producing 2-ethylhexyl-p-methoxycinnamate 失效
标题翻译： 2-甲基肉桂酸-2-乙基己酯的制备方法
公开(公告)号：US4970332A
公开(公告)日：1990-11-13
申请号：US321273
申请日：1989-03-09
申请人： Douglas C. Caskey
发明人： Douglas C. Caskey
IPC分类号： B01J23/44 , C07B61/00 , C07C51/367 , C07C67/343 , C07C69/734
CPC分类号： C07C51/367
摘要： A process for producing cinnamates comprising reacting an iodobenzene compound with an acrylate ester in the presence of trialkylamine and a catalyst comprising palladium on a support. In one embodiment, 2-ethylhexyl-p-methoxycinnamate is produced by the process comprising diazotizing p-anisidine to produce a diazotization product and reacting the diazotization product with an aqueous iodide solution to produce 4-iodoanisole, reacting the 4-iodoanisole product with 2-ethylhexylacrylate in the presence of trialkylamine and a catalyst comprising palladium on a support to produce 2-ethylhexyl-p-methoxycinnamate and a trialkylamine-hydroiodide salt and then recovering iodide and trialkylamine from the trialkylamine-hydroiodide salt by reacting the salt with an alkali hydroxide.
摘要翻译：一种生产肉桂酸酯的方法，包括在三烷基胺存在下使碘苯化合物与丙烯酸酯反应，并在载体上包含钯。在一个实施方案中，通过包括重氮化对甲氧基苯胺以产生重氮化产物并使重氮化产物与碘化碘水溶液反应以产生4-碘苯甲醚来制备2-甲氧基肉桂酸-2-乙基己酯，使4-碘苯甲醚产物与2 乙基己基丙烯酸酯在三烷基胺和包含钯的催化剂存在下在载体上制备2-乙基己基 - 对甲氧基肉桂酸酯和三烷基胺 - 氢碘酸盐，然后通过使该盐与碱金属氢氧化物反应从三烷基胺 - 氢碘酸盐中回收碘化物和三烷基胺。

4. 发明授权

US06559319B2 Synthesis of compounds useful in the manufacture of ketorolac 失效
公开(公告)号：US06559319B2
公开(公告)日：2003-05-06
申请号：US10233809
申请日：2002-09-03
申请人： Douglas C. Caskey , John R. Duchek , Henry J. Buehler
发明人： Douglas C. Caskey , John R. Duchek , Henry J. Buehler
IPC分类号： C07D20952
CPC分类号： C07D207/337 , C07D487/04
摘要： A multi-step method of synthesizing ketorolac, an analgesic compound, is shown. Several of the reactions and intermediate compounds are novel. The reaction sequence begins with the known compound N-2-bromoethylpyrrole.

5. 发明授权

US06489491B2 Synthesis of compounds useful in the manufacture of ketorolac 失效
公开(公告)号：US06489491B2
公开(公告)日：2002-12-03
申请号：US10072649
申请日：2002-02-05
申请人： Douglas C. Caskey , John R. Duchek , Henry J. Buehler
发明人： Douglas C. Caskey , John R. Duchek , Henry J. Buehler
IPC分类号： C07D207333
CPC分类号： C07D207/337 , C07D487/04
摘要： A multi-step method of synthesizing ketorolac, an analgesic compound, is shown. Several of the reactions and intermediate compounds are novel. The reaction sequence begins with the known compound N-2-bromoethylpyrrole.

6. 发明授权

US06376681B1 Synthesis of compounds useful in the manufacture of ketorolac 失效
标题翻译：可用于制造酮咯酸的化合物的合成
公开(公告)号：US06376681B1
公开(公告)日：2002-04-23
申请号：US09719033
申请日：2000-12-06
申请人： John R. Duchek , Henry J. Buehler , Douglas C. Caskey
发明人： John R. Duchek , Henry J. Buehler , Douglas C. Caskey
IPC分类号： C07D207327
CPC分类号： C07D207/337 , C07D487/04
摘要： This invention relates to the drug, ketorolac and the synthesis of compounds useful in the manufacture of ketorolac. Ketorolac tromethamine is a pharmaceutical compound useful as an analgesic.
摘要翻译：本发明涉及药物，酮咯酸和合成可用于制备酮咯酸的化合物。酮咯酸氨丁三醇是用作止痛剂的药物。

7. 发明授权

US4663480A Inhibiting polymerization of ethylenically unsaturated monomers with Mn(NO.sub.2).sub.2 失效
标题翻译：用Mn（NO2）2抑制烯属不饱和单体的聚合
公开(公告)号：US4663480A
公开(公告)日：1987-05-05
申请号：US741383
申请日：1985-06-05
申请人： Ervin B. Inskip , Douglas C. Caskey , William E. Dummitt
发明人： Ervin B. Inskip , Douglas C. Caskey , William E. Dummitt
IPC分类号： C07C51/50 , C07C67/62 , C08F2/40 , C07C57/02
CPC分类号： C07C51/50 , C07C67/62
摘要： Disclosed is a process for inhibiting polymerization of polymerizable ethylenically unsaturated monomers such as hydrocarbons, acids and esters, wherein manganese nitrite, i.e. Mn(NO.sub.2).sub.2, is employed as an inhibitor. A composition including a polymerizable ethylenically unsaturated monomer and Mn(NO.sub.2).sub.2 is also disclosed. In two preferred embodiments, acrylic acid and styrene, respectively, are the monomers.
摘要翻译：公开了抑制可聚合的烯属不饱和单体如烃，酸和酯的聚合的方法，其中使用亚硝酸锰，即Mn（NO 2）2作为抑制剂。还公开了包含可聚合的烯属不饱和单体和Mn（NO 2）2的组合物。在两个优选实施方案中，丙烯酸和苯乙烯分别是单体。

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