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公开(公告)号：US06515188B2
公开(公告)日：2003-02-04
申请号：US10115096
申请日：2002-04-04
IPC分类号： C07C523
CPC分类号： C07C41/26 , C07B2200/07 , C07C41/03 , C07C41/42 , C07C67/11 , C07C2601/14 , C07C69/16 , C07C69/08 , C07C43/196
摘要： A method for safely and efficiently producing high purity 3-l-menthoxypropane-1,2-diol and intermediates to be used in the method. As shown in the following reaction formula, 3-l-menthoxypropane-1,2-diol represented by the chemical formula (IV) is produced by adding l-menthol to a 1,2-epoxy-3-halogenopropane represented by the general formula (I) (wherein X represents a halogen atom) in an organic solvent in the presence of a Lewis acid, thereby producing a 1-halogeno-3-l-menthoxypropan-2-ol represented by the general formula (II), allowing the first intermediate to react with an alkali metal salt of an aliphatic carboxylic acid having from 1 to 5 carbon atoms to produce a 1-acyloxy-2-substituted-3-l-menthoxypropane represented by the general formula (III) and then hydrolyzing the second intermediate.
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公开(公告)号：US06407293B1
公开(公告)日：2002-06-18
申请号：US09962122
申请日：2001-09-26
IPC分类号： C07C3512
CPC分类号： C07C43/196 , C07C41/03
摘要： A process for producing highly pure 3-1-menthoxypropane-1,2-diol safely and efficiently, and an intermediate to be used in the process. 3-1-menthoxypropane-1,2-diol represented by the chemical formula (IV) is produced by adding 1-menthol to a 1,2-epoxy-3-halogenopropane represented by the following general formula (I) (wherein X represents a halogen atom) in an organic solvent in the presence of a Lewis acid to produce a novel 1-halogeno-3-1-menthoxypropan-2-ol represented by the following general formula (II), then, epoxidating it with a base in the presence of a phase transfer catalyst to produce a 1,2-epoxy-3-1-menthoxypropane represented by the chemical formula (III), and further hydrolyzing it.
摘要翻译： 安全有效地生产高纯度3-1-薄荷氧基丙二醇-1,2-二醇的方法，以及该方法中使用的中间体。 由化学式（IV）表示的3-1-薄荷氧基丙烷-1,2-二醇通过将1-薄荷醇加入到由下列通式（I）表示的1,2-环氧-3-氯代丙烷中（其中X表示 卤素原子）在有机溶剂中在路易斯酸存在下反应，得到由以下通式（II）表示的新型1-卤代-3-三氟甲氧基丙-2-醇，然后用碱进行环氧化 存在相转移催化剂以制备由化学式（III）表示的1,2-环氧-3-丁氧基丙烷，并进一步水解。
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公开(公告)号：US5959161A
公开(公告)日：1999-09-28
申请号：US179688
申请日：1998-10-27
IPC分类号： C07B57/00 , A01N31/04 , C07C29/00 , C07C29/09 , C07C29/14 , C07C29/159 , C07C29/56 , C07C29/78 , C07C29/86 , C07C35/08 , C07C45/45
CPC分类号： C07C29/00 , C07C29/09 , C07C2101/14
摘要： To offer a method of producing useful para-menthane-3,8-diol having the excellent repellent action to harmful living things, including noxious insects, in high purity and high yield, simply, and economically by the use of citronellal as a raw material compound.The above-mentioned problems are resolved by the production method of this invention wherein citronellal is treated with aqueous sulfuric acid solution of 0.02 to 1.0 wt. % in concentration to produce para-menthane-3,8-diol. In case of recovering the produced para-menthane-3,8-diol, a method is preferably adopted, wherein after the reaction product is extracted with an aliphatic hydrocarbon solvent of 5 to 8 in carbon number, the extract is cooled down at temperature higher than the melting point of said aliphatic hydrocarbon solvent and of -10.degree. C. or less to crystallize para-menthane-3,8-diol.
摘要翻译： 提供一种生产有效的对 - 薄荷烷-3,8-二醇的方法，其以高纯度和高产率，有效地利用香茅醛作为原料，对有害生物（包括有毒昆虫）具有优异的驱避作用 复合。 通过本发明的制备方法解决了上述问题，其中香茅醛用0.02-1.0wt。的硫酸水溶液处理。 产生对偏苯甲烷-3,8-二醇的浓度为％。 在回收生成的对 - 薄荷烷-3,8-二醇的情况下，优选采用方法，其中反应产物用碳数为5至8的脂族烃溶剂萃取后，将提取物在更高温度下冷却 比所述脂族烃溶剂的熔点低-10℃或更低以使对 - 薄荷烷-3,8-二醇结晶。
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