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1. 发明授权

US6103659A Catalyst comprising an amidophosphonium salt for halex reactions 失效
标题翻译：包含用于halex反应的酰胺鏻盐的催化剂
公开(公告)号：US6103659A
公开(公告)日：2000-08-15
申请号：US341986
申请日：1999-07-21
申请人： Sergej Pasenok , Wolfgang Appel , Ralf Pfirmann , Thomas Wessel , Thomas Schach , Hans Schubert
发明人： Sergej Pasenok , Wolfgang Appel , Ralf Pfirmann , Thomas Wessel , Thomas Schach , Hans Schubert
IPC分类号： B01J31/02 , C07B39/00 , C07B61/00 , C07C17/20 , C07C25/02 , C07C45/63 , C07C47/55 , C07C201/12 , C07C205/12 , B01J27/14 , C07D211/72 , C07D239/02 , C07D241/02
CPC分类号： C07C205/12 , B01J31/0202 , B01J31/0204 , B01J31/0239 , B01J31/0268 , C07B39/00 , C07C17/208 , C07C45/63 , B01J2231/40
摘要： Catalyst for halogen-fluorine exchange reactions on aromatics, consisting essentially of a mixture of one or more compounds of the component a) plus at least one compound of the components b), c) and/or d), whereina) is an amidophosphonium salt of the formula (I) ##STR1## where A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5, A.sup.6, A.sup.7, A.sup.8 are, independently of one another, identical or different and are each a straight-chain or branched alkyl or alkenyl having from 1 to 12 carbon atoms, cycloalkyl having from 4 to 8 carbon atoms, an aryl having from 6 to 12 carbon atoms, an aralkyl having from 7 to 12 carbon atoms, or A.sup.1 A.sup.2, A.sup.3 A.sup.4, A.sup.5 A.sup.6, A.sup.7 A.sup.8 are, independently of one another, identical or different and are in each case connected to one another either directly or via O or N--A.sup.9 to form a ring having from 3 to 7 ring atoms, A.sup.9 is an alkyl having from 1 to 4 carbon atoms and B.sup..crclbar. is a monovalent acid anion or the equivalent of a polyvalent acid anion,b) a quaternary ammonium salt,c) a quaternary phosphonium salt, andd) a crown ether or a polyether of the formula (IV):R.sup.10 --(O--O.sub.x H.sub.2x).sub.r --OR.sup.11 (IV).
摘要翻译： PCT No.PCT / EP90 / 00332 Sec。 371日期：1999年7月21日 102（e）日期1999年7月21日PCT提交1998年1月22日PCT公布。出版物WO98 / 32532 日期1998年7月30日关于芳族化合物的卤素 - 氟交换反应的催化剂，主要由一种或多种组分a）的化合物与至少一种组分b），c）和/或d）的化合物的混合物组成，其中 a）是式（I）的酰胺鏻盐，其中A1，A2，A3，A4，A5，A6，A7，A8彼此独立地相同或不同，并且各自是直链或支链烷基或烯基具有1至12个碳原子，具有4至8个碳原子的环烷基，具有6至12个碳原子的芳基，具有7至12个碳原子的芳烷基，或者A 1 A 2，A 3 A 4，A 5 A 6，A 7 A 8独立地为彼此相同或不同，并且各自直接或通过O或N-A9彼此连接以形成具有3至7个环原子的环，A 9是具有1至4个碳原子的烷基和B（ - ）是一价酸阴离子或多价酸阴离子当量，b）季铵盐，c）季鏻盐和d）冠醚或式（IV）的聚醚：R 10 - （O-OxH 2 x）r -OR 11（IV）。

2. 发明授权

US5466859A Process for preparing fluorobenzonitriles 失效
标题翻译：氟苯腈的制备方法
公开(公告)号：US5466859A
公开(公告)日：1995-11-14
申请号：US277518
申请日：1994-07-19
申请人： Thomas Schach , Theodor Papenfuhs , Ralf Pfirmann
发明人： Thomas Schach , Theodor Papenfuhs , Ralf Pfirmann
IPC分类号： B01J31/02 , C07B61/00 , C07C253/30 , C07C255/50
CPC分类号： B01J31/0204 , B01J31/0239 , C07C253/30 , B01J2231/40
摘要： Fluorobenzonitriles and chlorofluorobenzonitriles are prepared in an advantageous manner from the corresponding chlorobenzonitriles and an alkali metal fluoride in a chlorine-fluorine exchange reaction, by catalyzing the reaction with a quaternary ammonium compound comprising at least one alkoxypolyoxyalkyl radical.
摘要翻译：通过催化与包含至少一个烷氧基聚氧烷基的季铵化合物的反应，以有利的方式从相应的氯代苯腈和氯 - 氟交换反应中的碱金属氟化物制备氟代苯腈和氯氟苯腈。

3. 发明授权

US5565612A Substituted 2-chloro-3,4,5-trifluorobenzenes and a process for their preparation 失效
标题翻译：取代的2-氯-3,4,5-三氟苯及其制备方法
公开(公告)号：US5565612A
公开(公告)日：1996-10-15
申请号：US435794
申请日：1995-05-05
申请人： Ralf Pfirmann , Thomas Schach
发明人： Ralf Pfirmann , Thomas Schach
IPC分类号： C07C17/093 , C07C25/13 , C07C205/12 , C07C211/52 , C07C255/50 , C07C211/45
CPC分类号： C07C255/50 , C07C17/093 , C07C205/12 , C07C211/52 , C07C25/13
摘要： The present invention relates to substituted 2-chloro-3,4,5-trifluorobenzenes of the formula ##STR1## in which R is NO.sub.2, NH.sub.2, CN or Cl, and to a process for the preparation of substituted 2-chloro-3,4,5-trifluorobenzenes of the formula given above, in which R is NO.sub.2, NH.sub.2, CN, Cl or Br, which involves reacting 2,3,4-trifluorochlorobenzene with a nitrating agent in the presence or absence of a water-insoluble solvent at from -10.degree. C. to 50.degree. C., reducing 2-chloro-3,4,5-trifluoronitrobenzene or a mixture which contains 2-chloro-3,4,5-trifluoronitrobenzene and 5-chloro-2,3,4-trifluoronitrobenzene, in the presence of an organic solvent, isolating 2-chloro-3,4,5-trifluoroaniline or a mixture which contains 2-chloro-3,4,5-trifluoroaniline and 5-chloro-2,3,4-trifluoroaniline, diazotizing this product, if desired, and exchanging the diazotized group for a chloride atom, bromide atom or cyanide radical.
摘要翻译：本发明涉及其中R为NO 2，NH 2，CN或Cl的式“IMAGE”的取代的2-氯-3,4,5-三氟苯，以及制备取代的2-氯-3，其中R是NO 2，NH 2，CN，Cl或Br，其包括在存在或不存在水不溶性溶剂的情况下使2,3,4-三氟氯苯与硝化剂反应在-10℃至50℃下，还原2-氯-3,4,5-三氟硝基苯或含有2-氯-3,4,5-三氟硝基苯和5-氯-2,3,5-三氟硝基苯的混合物， 4-三氟硝基苯，在有机溶剂的存在下，分离出2-氯-3,4,5-三氟苯胺或含有2-氯-3,4,5-三氟苯胺和5-氯-2,3,4 如果需要，将该产物重氮化，并将重氮化的基团交换氯原子，溴原子或氰基。

4. 发明授权

US06407029B1 Mixtures comprising tetrakis(pyrrolidino/piperdino)phosphonium salts 有权
标题翻译：包含四（吡咯烷子基/哌啶子）鏻盐的混合物
公开(公告)号：US06407029B1
公开(公告)日：2002-06-18
申请号：US09617470
申请日：2000-07-17
申请人： Berthold Schiemenz , Thomas Wessel , Ralf Pfirmann , Andreas Beck , Walter Hahn
发明人： Berthold Schiemenz , Thomas Wessel , Ralf Pfirmann , Andreas Beck , Walter Hahn
IPC分类号： B01J2714
CPC分类号： C07C45/63 , C07B39/00 , C07F9/572 , C07F9/59 , C07C47/55
摘要： The present invention relates to mixtures comprising from 70 to 99.5% by weight of a compound of the formula (R)4P+X− (1) and from 30 to 0.5% by weight of a compound of the formula (R)3P═O (2), where R is in each case a radical and X− is an inorganic or organic anion or the equivalent of a multiply charged inorganic or organic anion, also to a process for preparing the mixtures by reacting a phosphorus pentahalide with pyrrolidine or piperidine in the molar ratio 1:6 to 1:50 in the presence of an inert solvent initially at −20 to 80° C., subsequently continuing the reaction at 90 to 180° C., treating the resulting reaction product at 0 to 80° C. with aqueous alkali at a pH of 7 to 15, and separating aqueous and organic phase from one another, and to the use of the mixtures as catalyst and cocatalyst for phase-transfer reactions, nucleophilic substitution reactions or halogen-fluorine exchange reactions.
摘要翻译：本发明涉及包含70-99.5重量％的式（R）4P + X-（1）的化合物和30至0.5重量％的式（R）化合物3P = O的混合物（2），其中R在每种情况下是基团，X是无机或有机阴离子或相当于多电荷无机或有机阴离子，也是通过使五卤化磷与吡咯烷或哌啶反应制备混合物的方法摩尔比1:6至1:50，最初在-20至80℃的惰性溶剂存在下，随后在90至180℃下继续反应，在0至80℃下处理所得反应产物与碱水溶液在pH为7至15，并分离水相和有机相，并将混合物用作催化剂和助催化剂用于相转移反应，亲核取代反应或卤素 - 氟交换反应。

5. 发明授权

US06187952B1 Two-step production of 3-chloro-4-fluoro-benzoyl chloride by chlorination 失效
标题翻译：通过氯化两步生产3-氯-4-氟 - 苯甲酰氯
公开(公告)号：US06187952B1
公开(公告)日：2001-02-13
申请号：US09209963
申请日：1998-12-10
申请人： Ralf Pfirmann , Thomas Wessel
发明人： Ralf Pfirmann , Thomas Wessel
IPC分类号： C07C5158
CPC分类号： C07C51/58 , C07C51/62 , C07C63/70
摘要： The present invention relates to a process for the preparation of 3-chloro-4-fluorobenzoyl chloride which comprises reacting 4-fluorobenzaldehyde with a chlorinating agent in the presence of a free-radical initiator in the presence or absence of a solvent at from −20 to 200° C. to give 4-fluorobenzoyl chloride, and reacting the 4-fluorobenzoyl chloride with a chlorinating agent in the presence of a chlorination catalyst in the presence or absence of a solvent at from −20 to 200° C. to give 3-chloro-4-fluorobenzoyl chloride.
摘要翻译：本发明涉及一种制备3-氯-4-氟苯甲酰氯的方法，其包括在存在或不存在溶剂的情况下，在自由基引发剂存在下，使4-氟苯甲醛与氯化剂在-20℃ 至200℃，得到4-氟苯甲酰氯，并且在-20℃至200℃下，在存在或不存在溶剂的情况下，在氯化催化剂存在下，使4-氟苯甲酰氯与氯化剂反应，得到3 - 氯-4-氟苯甲酰氯。

6. 发明授权

US5739388A Process for the preparation of aromatic compounds by decarboxylation of aromatic carboxylic acids 失效
标题翻译：通过芳族羧酸脱羧制备芳香族化合物的方法
公开(公告)号：US5739388A
公开(公告)日：1998-04-14
申请号：US641877
申请日：1996-05-02
申请人： Ralf Pfirmann , Hans Schubert
发明人： Ralf Pfirmann , Hans Schubert
IPC分类号： B01J23/72 , C07B37/06 , C07B61/00 , C07C1/207 , C07C15/02 , C07C17/363 , C07C25/02 , C07C37/50 , C07C39/02 , C07C39/24 , C07C51/38 , C07C65/03 , C07C65/21
CPC分类号： C07C51/38 , C07C17/363
摘要： The present invention relates to a process for the preparation of compounds of the formula ##STR1## in which the radicals R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are COOH, H, F, Cl, Br, CF.sub.3, OH, an alkoxy or alkyl radical having in each case 1 to 4 carbon atoms or a radical --NR.sup.6 R.sup.7, in which R.sup.6 and R.sup.7 are identical or different and are H, an alkyl radical having 1 to 4 carbon atoms or a phenyl radical, by dissolving in water a compound of the formula ##STR2## in which the radicals R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and have the abovementioned meaning or, in departure therefrom, instead of H can be COOH, admixing the aqueous solution with a water-insoluble amine which is inert under the reaction conditions and carrying out the decarboxylation at a pH of 3 to 9 and a temperature of 70.degree. to 210.degree. C. in the presence or absence of a water-insoluble solvent which is inert under the reaction conditions and in the presence or absence of a decarboxylation catalyst.
摘要翻译：本发明涉及一种制备式（1）化合物的方法，其中基团R 1，R 2，R 3，R 4和R 5相同或不同，为COOH，H，F，Cl，Br， CF 3，OH，各自为1至4个碳原子的烷氧基或烷基，或-NR 6 R 7基团，其中R 6和R 7相同或不同，为H，具有1至4个碳原子的烷基或苯基通过在水中溶解其中基团R 1，R 2，R 3，R 4和R 5相同或不同并具有上述含义的式（Ⅹ）的化合物，或者从其中代替H可以是COOH 将水溶液与在反应条件下为惰性的水不溶性胺混合，在存在或不存在水溶性的情况下，在3〜9的pH和70〜210℃的温度下进行脱羧，在反应条件下和存在或不存在脱羧基猫时是惰性的阿利斯特

7. 发明授权

US06645904B2 Aminophosphonium compounds 有权
标题翻译：氨基鏻化合物
公开(公告)号：US06645904B2
公开(公告)日：2003-11-11
申请号：US10135252
申请日：2002-04-30
申请人： Berthold Schiemenz , Thomas Wessel , Ralf Pfirmann
发明人： Berthold Schiemenz , Thomas Wessel , Ralf Pfirmann
IPC分类号： C07D26530
CPC分类号： B01J31/0268 , B01J31/0237 , B01J2531/985 , C07B39/00 , C07C45/63 , C07F9/06 , C07F9/572 , C07F9/59 , C07F9/650952 , C07F9/6533 , C07C47/55
摘要： The present invention relates to compounds of the formula in which one, two or three of the radicals R1, R2, R3 and R4 are where m and n are an integer from 1 to 10, R5, R6, R7 and R8 are, independently of one another, identical or different and are a straight-chain or branched alkyl radical having 1 to 10 carbon atoms, and the remaining radical(s) R1 to R4 are or —NR9R10, where R9 and R10 are identical or different and are a straight-chain or branched alkyl radical having 1 to 10 carbon atoms, and X− is an inorganic or organic anion or an equivalent of a multiply charged inorganic or organic anion. The invention further relates to mixtures of substances comprising compounds of the formula (1), to a process for preparing the compounds of the formula (1) and to the use thereof.
摘要翻译：本发明涉及式（1）中的一个，两个或三个基团R 1，R 2，R 3和R 4的化合物，其中m和n是1-10的整数，R R 5，R 7和R 8彼此独立地相同或不同，为具有1-10个碳原子的直链或支链烷基，剩余的基团（ s）R 1至R 4为-NR 9 R 10，其中R 9和R 10相同或不同，为具有1至10个碳原子的直链或支链烷基碳原子，X 1是无机或有机阴离子或等效的多电荷无机或有机阴离子。本发明还涉及包含式（1）化合物的物质的混合物，与制备式（1）化合物的方法及其用途。

8. 发明授权

US06465643B1 Aminophosphonium compounds 有权
标题翻译：氨基鏻化合物
公开(公告)号：US06465643B1
公开(公告)日：2002-10-15
申请号：US09617471
申请日：2000-07-17
申请人： Berthold Schiemenz , Thomas Wessel , Ralf Pfirmann
发明人： Berthold Schiemenz , Thomas Wessel , Ralf Pfirmann
IPC分类号： C07D26530
CPC分类号： B01J31/0268 , B01J31/0237 , B01J2531/985 , C07B39/00 , C07C45/63 , C07F9/06 , C07F9/572 , C07F9/59 , C07F9/650952 , C07F9/6533 , C07C47/55
摘要： The present invention relates to compounds of the formula in which one, two or three of the radicals R1, R2, R3 and R4 are where m and n are an integer from 1 to 10, R5, R6, R7 and R8 are, independently of one another, identical or different and are a straight-chain or branched alkyl radical having 1 to 10 carbon atoms, and the remaining radical(s) R1 to R4 are or —NR9R10, where R9 and R10 are identical or different and are a straight-chain or branched alkyl radical having 1 to 10 carbon atoms, and X− is an inorganic or organic anion or an equivalent of a multiply charged inorganic or organic anion. The invention further relates to mixtures of substances comprising compounds of the formula (1), to a process for preparing the compounds of the formula (1) and to the use thereof.
摘要翻译：本发明涉及式中的一个，两个或三个基团R 1，R 2，R 3和R 4的化合物，其中m和n是1至10的整数，R 5，R 6，R 7和R 8彼此独立地是相同或不同，为具有1至10个碳原子的直链或支链烷基，其余的R 1至R 4基团为-NR 9 R 10，其中R 9和R 10相同或不同，为直链或具有1-10个碳原子的支链烷基，X-是无机或有机阴离子或当量的多电荷无机或有机阴离子。本发明还涉及包含式（1）化合物的物质的混合物，与制备式（1）化合物的方法及其用途。

9. 发明授权

US5945556A Process for preparing N-carboxymethylene-4-chloro-anthranilic acid and its dialkyl esters 失效
标题翻译：制备N-羧基亚甲基-4-氯 - 邻氨基苯甲酸及其二烷基酯的方法
公开(公告)号：US5945556A
公开(公告)日：1999-08-31
申请号：US29414
申请日：1998-04-14
申请人： Theodor Papenfuhs , Ralf Pfirmann , Stefan Krause , Doris Neumann-Grimm
发明人： Theodor Papenfuhs , Ralf Pfirmann , Stefan Krause , Doris Neumann-Grimm
IPC分类号： C07C227/18 , C07C229/58 , C07C229/40
CPC分类号： C07C227/18
摘要： A process for preparing N-carboxymethylene-4-chloroanthranilic acid, and its dialkyl esters. The invention relates to a process for preparing N-carboxymethylene-4-chloroanthranilic acid and its dialkyl esters, which comprises reacting 2,4-dichlorobenzoic acid in the presence of a base, of a solvent and of a catalyst with glycine to give N-carboxymethylene-4-chloroanthranilic acid and, where appropriate, reacting the latter in the presence of a base and of a solvent with a dialkyl sulfate, dialkyl carbonate or alkyl halide to give the dialkyl ester.
摘要翻译： PCT No.PCT / EP69 / 03630 Sec。 371日期：1998年4月14日 102（e）1998年4月14日PCT PCT 1996年8月19日PCT公布。出版物WO97 / 08129 日期1997年3月6日制备N-羧基亚甲基-4-氯邻氨基苯甲酸及其二烷基酯的方法。本发明涉及一种制备N-羧基亚甲基-4-氯邻氨基苯甲酸及其二烷基酯的方法，其包括在碱，溶剂和催化剂与甘氨酸的存在下使2,4-二氯苯甲酸反应，得到N- 羧基亚甲基-4-氯邻氨基苯甲酸，并且在适当的情况下，使其在碱和溶剂的存在下与硫酸二烷基酯，碳酸二烷基酯或烷基卤反应，得到二烷基酯。

10. 发明授权

US5874608A Process for the preparation of esters of aromatic carboxylic acid 失效
标题翻译：芳香族羧酸酯的制备方法
公开(公告)号：US5874608A
公开(公告)日：1999-02-23
申请号：US858357
申请日：1997-05-19
申请人： Ralf Pfirmann , Theodor Papenfuhs
发明人： Ralf Pfirmann , Theodor Papenfuhs
IPC分类号： C07B61/00 , C07C67/11 , C07C69/76 , C07C227/18 , C07C229/54 , C07C319/20 , C07C323/62
CPC分类号： C07C67/11
摘要： The present invention relates to a process for the preparation of compounds of the formula (1)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOR (1)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms or OR, NHR, NR.sub.2, SR or COOR, in which R is an alkyl radical having 1 to 4 carbon atoms, Ar is an aryl radical having 6 to 12 carbon atoms and the radical R shown in formula (1) has the above meaning, by reacting a compound of the formula (2)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOH (2)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms, OH, NH.sub.2, NHR, SH or COOH and Ar has the same meaning as in formula (1), with a sulfate of the formula (RO).sub.2 SO.sub.2, in which R has the above meaning, in the presence of a water-insoluble tertiary amine and water at a temperature of 10.degree. to 120.degree. C. in the presence or absence of a water-insoluble solvent and with the addition of a base, at a pH of 5 to 12.
摘要翻译：本发明涉及制备式（1）化合物的方法，R1R2R3R4R5ArCOOR（1）其中R1，R2，R3，R4和R5相同或不同，为氢，卤素，烷基或烷氧基，其具有 1至6个碳原子或OR，NHR，NR 2，SR或COOR，其中R是具有1至4个碳原子的烷基，Ar是具有6至12个碳原子的芳基，并且式（1）中所示的基团R ）具有上述含义，通过使式（2）R 1 R 2 R 3 R 4 R 5 ArCOOH（2）的化合物与其中R 1，R 2，R 3，R 4和R 5相同或不同且为氢，卤素，烷基或烷氧基， 6个碳原子，OH，NH 2，NHR，SH或COOH和Ar的定义与式（1）中的含义相同，式（RO）2 SO 2的硫酸盐，其中R具有上述含义，水不溶性叔胺和水，在存在或不存在水不溶性溶剂的情况下，在10〜120℃的温度下加入碱，在pH为 5至12。

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