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1. 发明授权

US4914208A Optically active salts of a substituted thiazolidine-4-carboxylate and 3-chloro-2-hydroxypropyltrimethyl ammonium, their preparation and use 失效
标题翻译：取代噻唑烷-4-羧酸酯和3-氯-2-羟丙基三甲基铵的光学活性盐，其制备和用途
公开(公告)号：US4914208A
公开(公告)日：1990-04-03
申请号：US262722
申请日：1988-10-17
申请人： Harald Jakob , Klaus Huthmacher , Herbert Klenk , Axel Kleemann , Gunes Giray
发明人： Harald Jakob , Klaus Huthmacher , Herbert Klenk , Axel Kleemann , Gunes Giray
IPC分类号： C07B57/00 , C07C67/00 , C07C213/00 , C07C213/04 , C07C215/40 , C07D277/06
CPC分类号： C07C215/40 , C07D277/06
摘要： The invention relates to the preparation of optically active salts of the general formula ##STR1## from which the corresponding optically active 3-chloro-2-hydroxypropyltrimethyl ammonium chloride can be obtained by treatment with mineral acid.The L(-) form of this compound is a valuable component for the synthesis of L(-) carnitine.
摘要翻译：本发明涉及制备通式（I）的光学活性盐，通过用无机酸处理可得到相应的光学活性3-氯-2-羟丙基三甲基氯化铵。该化合物的L（ - ）形式是合成L（ - ）肉碱的有价值的成分。

2. 发明授权

US5166426A Process for producing L-carnitine from D,L-carnitine nitrile salts 失效
标题翻译：从D，L-CARNITINE NITRILE SALTS生产L-酪氨酸的方法
公开(公告)号：US5166426A
公开(公告)日：1992-11-24
申请号：US858492
申请日：1992-03-27
申请人： Harald Jakob , Klaus Huthmacher , Herbert Klenk
发明人： Harald Jakob , Klaus Huthmacher , Herbert Klenk
IPC分类号： C07B57/00 , C07C227/34 , C07C229/06
CPC分类号： C07C227/34
摘要： Synthesis of L-carnitine by chemical optical resolution of D,L-carnitine nitrile salts, where the D,L-carnitine nitrile salt is reacted with optically active N-acetylproline as the resolving agent in order to form the diastereomer salts after conversion to the hydroxide form, one of the two diastereomer salts is separated by fractional crystallization and the fraction containing mainly L-carnitine nitrile salt is treated with an optically inactive strong acid in order to split off the optically active N-acetylproline and then the resolving agent is separated and the resulting L-carnitine nitrile salt is saponified to L-carnitine. N-acetyl-L-proline is used as the resolving agent and the diastereomer (LL) salt is obtained in crystalline form in a high optical purity by fractional crystallization and the L-carnitine nitrile salt obtained after splitting off and separating N-acetyl-L-proline is used directly for saponification without further crystallization.
摘要翻译：通过化学光学拆分D，L-肉碱腈盐合成左旋肉碱，其中D，L-肉毒碱腈与光学活性N-乙酰脯氨酸作为拆分剂反应，以便在转化为氢氧化物形式，通过分级结晶分离两种非对映异构体盐中的一种，并且用光学惰性的强酸处理主要含有L-肉碱腈盐的级分，以便分离光学活性N-乙酰脯氨酸，然后分离出拆分剂并将所得的L-肉碱腈盐皂化成L-肉毒碱。使用N-乙酰基-L-脯氨酸作为拆分剂，通过分级结晶以高光学纯度获得结晶形式的非对映异构体（LL）盐，分解N-乙酰基-L-脯氨酸后得到的L-肉碱腈盐， L-脯氨酸直接用于皂化而不进一步结晶。

3. 发明授权

US5191085A Optically active salts of a substituted thiazolidine-4-carboxylate and 3-cyano-hydroxypropyl trimethyl-ammonium, their production and uses 失效
标题翻译：取代的噻唑烷-4-羧酸酯和3-氰基 - 羟丙基三甲基氨基铵的光学活性物质，其生产和用途
公开(公告)号：US5191085A
公开(公告)日：1993-03-02
申请号：US675623
申请日：1991-03-27
申请人： Harald Jakob , Klaus Huthmacher , Herbert Klenk
发明人： Harald Jakob , Klaus Huthmacher , Herbert Klenk
IPC分类号： C07B53/00 , C07C255/26 , C07D277/06
CPC分类号： C07D277/06
摘要： Optically active salts are disclosed of the formula (I): ##STR1## wherein Ac represents an acyl group, R.sup.1 hydrogen or methyl, R.sup.2 and R.sup.3 identical or different substitutes, preferably methyl. The salts can be obtained from the corresponding optically active carbonic acid and DL-3-cyano-2-hydroxypropyl trimethylammonium hydroxide. The diastereomeric salt pairs are easily split from one another and separated again, so that the process is suited for producing optically active 3-cyano-2-hydroxypropyl trimethylammonium salts.
摘要翻译：公开了式（I）的光学活性盐：其中Ac表示酰基，R 1氢或甲基，R 2和R 3相同或不同的取代基，优选甲基。盐可以从相应的光学活性碳酸和DL-3-氰基-2-羟丙基三甲基铵氢氧化物获得。非对映体盐对彼此容易分离并再次分离，因此该方法适用于制备光学活性3-氰基-2-羟丙基三甲基铵盐。

4. 发明授权

US09464045B2 Process for the preparation of methionine 有权
标题翻译：制备甲硫氨酸的方法
公开(公告)号：US09464045B2
公开(公告)日：2016-10-11
申请号：US14850207
申请日：2015-09-10
申请人： Martin Koerfer , Hans Joachim Hasselbach , Stefan Reichert , Harald Jakob , Christoph Weckbecker , Klaus Huthmacher , Horst Krull , Bernd Drapal , Rainer Peter
发明人： Martin Koerfer , Hans Joachim Hasselbach , Stefan Reichert , Harald Jakob , Christoph Weckbecker , Klaus Huthmacher , Horst Krull , Bernd Drapal , Rainer Peter
IPC分类号： C07C319/28 , C07C319/20 , C07C319/26 , C07C319/12 , C07C323/52
CPC分类号： C07C319/28 , C07C319/12 , C07C319/20 , C07C319/26 , C07C323/52 , Y02P20/142 , C07C323/58
摘要： This disclosure relates to a process for preparing D,L-methionine by feeding carbon dioxide to an aqueous potassium methioninate solution obtained by hydrolysis of 5-(2-methylmercaptoethyl)hydantoin, in order to precipitate out crude methionine, which is separated off and purified. In this process an aqueous solution of the separated-off crude methionine is purified by recrystallization from a solution containing potassium ions and also a crystallization additive. The crystallization additive is a nonionic or anionic surfactant, or a mixture of different nonionic or anionic surfactants. The recrystallization occurs by introducing a 60 to 110° C.-hot methionine solution into a 35 to 80° C.-warm methionine suspension, a temperature of which is lower than that of the introduced solution, such that the temperature of the methionine suspension being maintained between 35 and 80° C. during the addition. The crystallization additive is a sorbitan fatty acid ester or a mixture of different sorbitan fatty acid esters.
摘要翻译：本公开涉及通过将二氧化碳供给到通过水解5-（2-甲基巯基乙基）乙内酰脲获得的甲硫氨酸钾水溶液以便沉淀出粗蛋氨酸的方法来制备D，L-甲硫氨酸，其分离和纯化。在该方法中，分离的粗甲硫氨酸的水溶液通过从含有钾离子的溶液和结晶添加剂中重结晶来纯化。结晶添加剂是非离子或阴离子表面活性剂，或不同的非离子或阴离子表面活性剂的混合物。通过将60〜110℃的甲硫氨酸溶液导入35〜80℃的甲硫氨酸悬浮液中，其温度低于引入的溶液的温度，使得甲硫氨酸悬浮液的温度在添加期间保持在35和80℃之间。结晶添加剂是脱水山梨糖醇脂肪酸酯或不同脱水山梨糖醇脂肪酸酯的混合物。

5. 发明授权

US09156782B2 Process for the preparation of methionine 有权
标题翻译：制备甲硫氨酸的方法
公开(公告)号：US09156782B2
公开(公告)日：2015-10-13
申请号：US14386165
申请日：2013-02-26
申请人： Martin Koerfer , Hans Joachim Hasselbach , Stefan Reichert , Harald Jakob , Christoph Weckbecker , Klaus Huthmacher , Horst Krull , Bernd Drapal , Rainer Peter
发明人： Martin Koerfer , Hans Joachim Hasselbach , Stefan Reichert , Harald Jakob , Christoph Weckbecker , Klaus Huthmacher , Horst Krull , Bernd Drapal , Rainer Peter
IPC分类号： C07C319/12 , C07C319/20 , C07C319/26 , C07C319/28 , C07C323/52
CPC分类号： C07C319/28 , C07C319/12 , C07C319/20 , C07C319/26 , C07C323/52 , Y02P20/142 , C07C323/58
摘要： The invention relates to a process for the preparation of D,L-methionine, in which carbon dioxide is fed to an aqueous potassium methioninate solution obtained by hydrolysis of 5-(2-methylmercaptoethyl)hydantoin, in order to precipitate out crude methionine, which is separated off and purified, where, for the purposes of purification, an aqueous solution of the separated-off crude methionine is prepared and subjected to a recrystallization, characterized in that the solution from which the recrystallization takes place contains potassium ions and also a crystallization additive, where the crystallization additive is a nonionic or anionic surfactant, or a mixture of different nonionic or anionic surfactants, and that the recrystallization takes place by introducing a 60 to 110° C.-hot methionine solution into a 35 to 80° C.-warm methionine suspension, the temperature of which is lower than that of the introduced solution, the temperature of the methionine suspension being maintained between 35 and 80° C. during the addition.
摘要翻译：本发明涉及一种制备D，L-甲硫氨酸的方法，其中将二氧化碳加入到通过5-（2-甲基巯基乙基）乙内酰脲的水解获得的甲硫氨酸钾水溶液中，以沉淀出粗蛋氨酸，分离纯化，其中，为了纯化的目的，制备分离的粗制甲硫氨酸的水溶液并进行重结晶，其特征在于进行重结晶的溶液含有钾离子并且还具有结晶添加剂，其中结晶添加剂是非离子或阴离子表面活性剂，或不同的非离子或阴离子表面活性剂的混合物，并且通过将60至110℃的热甲硫氨酸溶液引入35至80℃进行重结晶。 - 温血蛋氨酸悬浮液，其温度低于引入溶液的温度，甲硫氨酸悬浮液的温度维持在在加入过程中在35和80℃之间。

6. 发明申请

US20150051421A1 PROCESS FOR THE PREPARATION OF METHIONINE 有权
标题翻译：制备甲硫氨酸的方法
公开(公告)号：US20150051421A1
公开(公告)日：2015-02-19
申请号：US14386165
申请日：2013-02-26
申请人： Martin Koerfer , Hans Joachim Hasselbach , Stefan Reichert , Harald Jakob , Christoph Weckbecker , Klaus Huthmacher , Horst Krull , Bernd Drapal , Rainer Peter
发明人： Martin Koerfer , Hans Joachim Hasselbach , Stefan Reichert , Harald Jakob , Christoph Weckbecker , Klaus Huthmacher , Horst Krull , Bernd Drapal , Rainer Peter
IPC分类号： C07C319/12 , C07C323/52
CPC分类号： C07C319/28 , C07C319/12 , C07C319/20 , C07C319/26 , C07C323/52 , Y02P20/142 , C07C323/58
摘要： The invention relates to a process for the preparation of D,L-methionine, in which carbon dioxide is fed to an aqueous potassium methioninate solution obtained by hydrolysis of 5-(2-methylmercaptoethyl)hydantoin, in order to precipitate out crude methionine, which is separated off and purified, where, for the purposes of purification, an aqueous solution of the separated-off crude methionine is prepared and subjected to a recrystallization, characterized in that the solution from which the recrystallization takes place contains potassium ions and also a crystallization additive, where the crystallization additive is a nonionic or anionic surfactant, or a mixture of different nonionic or anionic surfactants, and that the recrystallization takes place by introducing a 60 to 110° C.-hot methionine solution into a 35 to 80° C.-warm methionine suspension, the temperature of which is lower than that of the introduced solution, the temperature of the methionine suspension being maintained between 35 and 80° C. during the addition.
摘要翻译：本发明涉及一种制备D，L-甲硫氨酸的方法，其中将二氧化碳加入到通过5-（2-甲基巯基乙基）乙内酰脲的水解获得的甲硫氨酸钾水溶液中，以沉淀出粗蛋氨酸，分离纯化，其中，为了纯化的目的，制备分离的粗制甲硫氨酸的水溶液并进行重结晶，其特征在于进行重结晶的溶液含有钾离子并且还具有结晶添加剂，其中结晶添加剂是非离子或阴离子表面活性剂，或不同的非离子或阴离子表面活性剂的混合物，并且通过将60至110℃的热甲硫氨酸溶液引入35至80℃进行重结晶。 - 温血蛋氨酸悬浮液，其温度低于引入溶液的温度，甲硫氨酸悬浮液的温度维持在在加入过程中在35和80℃之间。

7. 发明授权

US09809535B2 Process for the preparation of alkyl mercaptans 有权
公开(公告)号：US09809535B2
公开(公告)日：2017-11-07
申请号：US14974625
申请日：2015-12-18
申请人： Benjamin Fonfe , Stephan Kretz , Harald Jakob
发明人： Benjamin Fonfe , Stephan Kretz , Harald Jakob
IPC分类号： C07C319/08
CPC分类号： C07C319/08 , C07C321/04
摘要： An alkyl mercaptan is prepared by reacting an aliphatic alcohol with hydrogen sulfide in the presence of a heterogeneous catalyst at varying temperatures.

8. 发明授权

US08658590B2 Coated sodium percarbonate particles 有权
标题翻译：涂覆过碳酸钠颗粒
公开(公告)号：US08658590B2
公开(公告)日：2014-02-25
申请号：US12310817
申请日：2007-07-04
申请人： Stefan Leininger , Harald Jakob , Ulrike Kottke
发明人： Stefan Leininger , Harald Jakob , Ulrike Kottke
IPC分类号： C11D3/10
CPC分类号： C11D17/0039 , C01B15/106 , C11D3/046 , C11D3/10 , C11D3/3942 , Y10T428/2991
摘要： Coated sodium percarbonate particles comprising a core of sodium percarbonate obtainable by fluidized bed buildup granulation, and a coating layer comprising sodium sulfate and sodium carbonate in a weight ratio of from 95:5 to 75:25 and in which the proportion of sodium sulfate and sodium carbonate is at least 80% by weight, effect as a detergent component an improved washing power of the detergent and exhibit a high storage stability in detergent formulations.
摘要翻译：包含通过流化床堆积制粒可获得的过碳酸钠核心的包覆过碳酸钠颗粒和包含重量比为95:5至75:25的硫酸钠和碳酸钠的涂层，其中硫酸钠和钠的比例碳酸酯的含量至少为80重量％，作为洗涤剂组分可以改善洗涤剂的洗涤能力，并且在洗涤剂配方中表现出高的储存稳定性。

9. 发明申请

US20130053299A1 Fabric Softening Composition 有权
标题翻译：织物柔软组合物
公开(公告)号：US20130053299A1
公开(公告)日：2013-02-28
申请号：US13643486
申请日：2011-04-19
申请人： Hans-Jürgen Köhle , Ulrike Kottke , Hans Henning , Harald Jakob
发明人： Hans-Jürgen Köhle , Ulrike Kottke , Hans Henning , Harald Jakob
IPC分类号： C11D3/60
CPC分类号： C11D1/835 , C07C213/06 , C07C219/06 , C11D1/62 , C11D1/667 , C11D3/001 , C11D3/0015 , C11D3/2013 , C11D3/2079
摘要： A fabric softening composition which comprises as component A a tertiary or quaternary ammonium salt of formulae (I) or (II): R1R2R3N+CH2CHR4OC(═O)R5X− (I) R1R2R3N+(CH2)3NHR(═O)R5X− (II) in which R1 is hydrogen, methyl or ethyl, R2 and R3, independently of one another, are C1-4 alkyl or C2-4 hydroxyalkyl, R4 is hydrogen or methyl, R5 is a linear C15-21 alkyl or alkenyl radical and X− is a monovalent anion, and as component B a nonionic softener with only one long-chain hydrocarbon radical bonded to a polar radical having at least one free hydroxy group, where fatty alcohol alkoxylate or fatty acid alkoxylate are excluded as component B, exhibits a good softening effect and forms storage-stable dispersions if the molar ratio of component A to component B is in the range from 2:1 to 1:3, the difference between the average chain length of the long-chain hydrocarbon radicals of components A and B is at most 2 carbon atoms and the hydrocarbon radicals of components A and B have on average in each case at most 0.5 double bonds per hydrocarbon radical.Such a composition can be produced by reacting a fatty acid, a C2-6 diol or C3-9 polyol, and a tertiary alkanolamine or a diamine having a tertiary and primary amino group in a suitable molar ratio with the removal of water and subsequent alkylation or protonation.
摘要翻译：包含作为组分A的式（I）或（II）的叔胺或季铵盐的织物柔软组合物：R1R2R3N + CH2CHR4OC（= O）R5X-（I）R1R2R3N +（CH2）3NHR（= O）R5X-（II ）其中R1是氢，甲基或乙基，R2和R3彼此独立地是C1-4烷基或C2-4羟烷基，R4是氢或甲基，R5是直链C15-21烷基或烯基，X是 - 是一价阴离子，并且作为组分B，不包括仅具有一个长链烃基键合至具有至少一个游离羟基的极性基团的非离子软化剂，其中排除脂肪醇烷氧基化物或脂肪酸烷氧基化物作为组分B，表现出如果组分A与组分B的摩尔比在2:1至1:3的范围内，组分A的长链烃基的平均链长与组分A的长链烃基的平均链长与 B是至多2个碳原子和组分A和C的烃基 B在每种情况下平均每个烃基最多0.5个双键。这样的组合物可以通过使脂肪酸，C 2-6二醇或C 3-9多元醇与叔链烷醇胺或具有叔胺和伯氨基的二胺与合适的摩尔比与水的去除和随后的烷基化反应来制备或质子化。

10. 发明申请

US20100171230A1 Method for Production of Granular Sodium Percarbonate 审中-公开
标题翻译：颗粒过碳酸钠的生产方法
公开(公告)号：US20100171230A1
公开(公告)日：2010-07-08
申请号：US12442865
申请日：2007-07-17
申请人： Stefan Leininger , Michael Scheibe , Lothar Kaiser , Bertram Trautvetter , Waldemar Hessberger , Marcel Verduyn , Holger Pitsch , Harald Jakob
发明人： Stefan Leininger , Michael Scheibe , Lothar Kaiser , Bertram Trautvetter , Waldemar Hessberger , Marcel Verduyn , Holger Pitsch , Harald Jakob
IPC分类号： B29B9/10
CPC分类号： C01B15/103 , B01J2/16
摘要： The process for producing granular sodium percarbonate by fluidized bed buildup granulation comprises the spraying of an aqueous solution of hydrogen peroxide and of an aqueous solution of sodium carbonate with at least one multisubstance nozzle with external mixing into a fluidized bed comprising sodium percarbonate particles and simultaneously evaporating water, and is characterized in that the solution of sodium carbonate additionally comprises sodium carbonate and/or sodium percarbonate in suspended form and is passed through a dispersing apparatus for dispersion of solids before being fed to the multisubstance nozzle.The process allows the blockage of the multisubstance nozzle to be avoided and sodium percarbonate dust to be recycled from the offgas stream of the fluidized bed into the granulation.
摘要翻译：通过流化床堆积制粒生产颗粒状过碳酸钠的方法包括将过氧化氢水溶液和碳酸钠水溶液与至少一个多质量喷嘴进行外部混合喷入包含过碳酸钠颗粒的流化床中并同时蒸发水，其特征在于，碳酸钠溶液另外包含悬浮形式的碳酸钠和/或过碳酸钠，并且在进料到多功能喷嘴之前通过用于分散固体的分散装置。该过程允许避免多功能喷嘴的堵塞，并且将过碳酸钠粉尘从流化床的废气流再循环到造粒中。

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