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1. 发明授权

US5532411A Production of carboxylic acid halides and carboxylate salts 失效
标题翻译：制备羧酸卤化物和羧酸盐
公开(公告)号：US5532411A
公开(公告)日：1996-07-02
申请号：US233624
申请日：1994-04-26
申请人： Max Braun , Werner Rudolph , Stefan Palsherm , Kerstin Eichholz
发明人： Max Braun , Werner Rudolph , Stefan Palsherm , Kerstin Eichholz
IPC分类号： C07C51/41 , C07C51/60 , C07C53/18 , C07C67/14 , C07C51/58 , C07C69/02
CPC分类号： C07C67/14 , C07C51/60
摘要： A process for preparing carboxylic acid halides and carboxylate salts by reacting metal or "onium" halides with carboxylic anhydrides, which process is very suitable for working-up anhydrous, spent catalyst preparations. The resulting carboxylic acid halide or carboxylate salt can be used as an acylating reagent or alkylating reagent, and metal halide or "onium" halide liberated during this can be reacted anew with carboxylic anhydride and regenerated, thereby making it possible to effect a hydrolysis-free alkylation or acylation without forming salt-type waste products. If the mixture of carboxylic acid halide and carboxylate salt is allowed to react with an alcohol, preferably in situ, the resulting ester can be isolated without hydrolysis.
摘要翻译：通过使金属或“鎓”卤化物与羧酸酐反应来制备羧酸卤化物和羧酸盐的方法，该方法非常适用于加工无水的废催化剂制剂。所得羧酸卤化物或羧酸盐可用作酰化试剂或烷化试剂，并且在此期间释放的金属卤化物或“鎓”卤化物可与羧酸酐重新反应并再生，从而可以实现无水解烷基化或酰化而不形成盐类废物。如果允许羧酸卤化物和羧酸盐的混合物与醇反应，优选原位，所得到的酯可以在不水解的情况下分离。

2. 发明授权

US07282120B2 UV-activated chlorination process 失效
标题翻译：紫外线活化氯化法
公开(公告)号：US07282120B2
公开(公告)日：2007-10-16
申请号：US11008109
申请日：2004-12-10
申请人： Max Braun , Kerstin Eichholz , Stefan Palsherm , Carsten Brosch
发明人： Max Braun , Kerstin Eichholz , Stefan Palsherm , Carsten Brosch
IPC分类号： C07B63/00 , C07C17/00
CPC分类号： C07C17/10 , C07C17/04 , C07C17/395 , C07C19/01 , C07C19/12 , C07C19/08
摘要： A method of producing alkanes containing chlorine by addition of chlorine to C—C double bonds or C—C triple bonds or by exchange of hydrogen for chlorine by contacting the starting compound in the gas or liquid phase with elemental chlorine and irradiating the reaction mixture with UV light having a wavelength of λ≧280 nm. In this way pentachloroethane can be produced from trichloroethylene, CFC-113 from HCFC-123 or HFC-133a, CFC-112a from HCFC-142b, or HCFC-123 from HCFC-133a. The method also is suitable for separating photochlorinatable impurities from HFC-365-mfc to obtain purified HFC-365-mfc. Advantages include high yields and excellent selectivity.
摘要翻译：通过将氯气加入到CC双键或CC三键中，或通过使气相或液相中的起始化合物与元素氯接触并将反应混合物与具有 λ> 280nm波长。以这种方式，可以从三氯乙烯，来自HCFC-123的CFC-113或HFC-133a，来自HCFC-142b的CFC-112a或来自HCFC-133a的HCFC-123制备五氯乙烷。该方法也适用于从HFC-365-mfc分离光可氯化杂质，得到纯化的HFC-365-mfc。优点包括高产率和极好的选择性。

3. 发明授权

US06723874B1 Method of producing acid fluorides from acid chlorides 失效
标题翻译：从酰氯生产酸性氟化物的方法
公开(公告)号：US06723874B1
公开(公告)日：2004-04-20
申请号：US09856909
申请日：2001-05-30
申请人： Max Braun , Matthias Rieland , Francine Janssens , Kerstin Eichholz , Stefan Palsherm
发明人： Max Braun , Matthias Rieland , Francine Janssens , Kerstin Eichholz , Stefan Palsherm
IPC分类号： C07C5158
CPC分类号： C01B17/4576 , C01B17/4561 , C07C51/58
摘要： Acid fluorides, for example carboxylic acid fluorides and sulfuryl fluoride are produced by reacting the corresponding acid chlorides with hydrogen fluoride adducts of ammonium fluoride or amine hydrofluorides (which act as a catalyst or as a fluorination agent). Consumed HF adducts may be regenerated with HF.
摘要翻译：酸性氟化物，例如羧酸氟化物和硫酰氟通过使相应的酰氯与氟化铵或胺氢氟酸（其充当催化剂或氟化剂）的氟化氢加合物反应来制备。消耗的HF加合物可以用HF再生。

4. 发明申请

US20050101811A1 UV-activated chlorination process 失效
标题翻译：紫外线活化氯化法
公开(公告)号：US20050101811A1
公开(公告)日：2005-05-12
申请号：US11008109
申请日：2004-12-10
申请人： Max Braun , Kerstin Eichholz , Stefan Palsherm , Carsten Brosch
发明人： Max Braun , Kerstin Eichholz , Stefan Palsherm , Carsten Brosch
IPC分类号： C07C17/04 , C07C17/10 , C07C17/395 , C07C19/043 , C07C19/08 , C07C19/12 , C07C17/00
CPC分类号： C07C17/10 , C07C17/04 , C07C17/395 , C07C19/01 , C07C19/12 , C07C19/08
摘要： A method of producing alkanes containing chlorine by addition of chlorine to C—C double bonds or C—C triple bonds or by exchange of hydrogen for chlorine by contacting the starting compound in the gas or liquid phase with elemental chlorine and irradiating the reaction mixture with UV light having a wavelength of λ>280 nm. In this way pentachloroethane can be produced from trichloroethylene, CFC-113 from HCFC-123 or HFC-133a, CFC-112a from HCFC-142b, or HCFC-123 from HCFC-133a. The method also is suitable for separating photochlorinatable impurities from HFC-365-mfc to obtain purified HFC-365-mfc. Advantages include high yields and excellent selectivity.
摘要翻译：通过将氯气加入到CC双键或CC三键中，或通过使气相或液相中的起始化合物与元素氯接触并将反应混合物与具有波长> 280nm。以这种方式，可以从三氯乙烯，来自HCFC-123的CFC-113或HFC-133a，来自HCFC-142b的CFC-112a或来自HCFC-133a的HCFC-123制备五氯乙烷。该方法也适用于从HFC-365-mfc分离光可氯化杂质，得到纯化的HFC-365-mfc。优点包括高产率和极好的选择性。

5. 发明授权

US06252105B1 Synthesis of low-fluoride organic compounds 失效
标题翻译：低氟有机化合物的合成
公开(公告)号：US06252105B1
公开(公告)日：2001-06-26
申请号：US09348072
申请日：1999-07-06
申请人： Max Braun , Johannes Eicher , Francine Janssens , Kerstin Eichholz , Stefan Palsherm
发明人： Max Braun , Johannes Eicher , Francine Janssens , Kerstin Eichholz , Stefan Palsherm
IPC分类号： C07C6963
CPC分类号： C07C67/56 , C07C51/47 , C07C51/64 , C07C53/18 , C07C67/14 , C07C67/58 , C07C53/48 , C07C59/195 , C07C69/63 , C07C69/72
摘要： Organic compounds, e.g. fluorinated organic compounds such as fluorinated carboxylic acids or fluorinated carboxylic acid chlorides, may contain small amounts of carboxylic acid fluorides, hydrogen fluoride or hydrolyzable fluoride, which during the preparation of derivatives of the fluorinated organic compounds, for example by esterification, may yield corrosive fluorides or hydrogen fluoride. The invention is a method for the synthesis and/or purification of preferably fluorinated organic compounds such as carboxylic acids, carboxylic acid chlorides and derivatives such as esters thereof, starting from corresponding carboxylic acid chlorides containing acid fluorides or hydrolyzable fluoride, and alcohols under the catalytic action of “onium” salts of carboxylic acids, to obtain products which have a low fluoride content. Alternatively, an inorganic oxide adsorbent is utilized. The method is especially suitable for the synthesis of esters of trifluoroacetic acid, chlorodifluoroacetic acid, trifluoroacetoacetic acid and/or difluoroacetoacetic acid.
摘要翻译：有机化合物，例如含氟有机化合物如氟化羧酸或氟化羧酸氯化物可含有少量羧酸氟化物，氟化氢或水解性氟化物，其在氟化有机化合物衍生物的制备过程中，例如通过酯化反应，可产生腐蚀性氟化物或氟化氢。本发明是一种合成和/或纯化优选氟化有机化合物如羧酸，羧酸氯化物及其衍生物如酯的方法，起始于含有酸性氟化物或可水解氟化物的相应的羧酸氯化物和催化剂下的醇羧酸的“鎓”盐的作用，以获得具有低氟含量的产物。或者，使用无机氧化物吸附剂。该方法特别适用于三氟乙酸，氯二氟乙酸，三氟乙酰乙酸和/或二氟乙酰乙酸的酯的合成。

6. 发明授权

US5481029A Process for preparation of ketones 失效
标题翻译：酮的制备方法
公开(公告)号：US5481029A
公开(公告)日：1996-01-02
申请号：US233622
申请日：1994-04-26
申请人： Max Braun , Johannes Eicher , Werner Rudolph , Kerstin Eichholz
发明人： Max Braun , Johannes Eicher , Werner Rudolph , Kerstin Eichholz
IPC分类号： B01J31/02 , C07B61/00 , C07C45/48 , C07C45/65 , C07C45/67 , C07C49/04 , C07C49/167 , C07C67/10 , C07C67/313 , C07C67/343 , C07C69/63 , C07C69/716
CPC分类号： C07C45/48 , C07C45/676 , C07C49/167 , C07C67/10
摘要： A process for preparing ketones, for example CF.sub.3 C(O)CH.sub.3, CF.sub.3 C(O)CH.sub.2 C(O)CF.sub.3 and CF.sub.3 C(O)CF.sub.2 H, in which .beta.-ketoesters are transesterified and decarboxylated using a carboxylic acid, for example trifluoroacetic acid, in the presence of a catalyst, particularly an "onium" salt of a carboxylic acid or an effective amount of a proton-donating acid, preferably a sulfonic acid such as alkyl- or arylsulfonic acids, or a mineral acid. The process is advantageously carried out in the absence of water, so that no formation of acetals or hydrates occurs, and no dehydrating step is needed. The process is simple to carry out, and if transesterification is carried out with a sufficiently active carboxylic acid, for example with trifluoroacetic acid, the presence of an additional catalyst is unnecessary.
摘要翻译：制备酮的方法，例如CF 3 C（O）CH 3，CF 3 C（O）CH 2 C（O）CF 3和CF 3 C（O）CF 2 H），其中β-酮酯使用羧酸（例如三氟乙酸）进行酯交换和脱羧存在催化剂，特别是羧酸的“鎓”盐或有效量的质子供体酸，优选磺酸如烷基或芳基磺酸或无机酸。该方法有利地在没有水的情况下进行，使得不会发生缩醛或水合物的形成，并且不需要脱水步骤。该方法很容易进行，如果用足够活泼的羧酸（例如三氟乙酸）进行酯交换反应，则不需要另外的催化剂的存在。

7. 发明授权

US5405991A Process for producing carboxylic acid esters from carboxylic acid halides and alcohols 失效
标题翻译：由羧酸卤化物和醇生产羧酸酯的方法
公开(公告)号：US5405991A
公开(公告)日：1995-04-11
申请号：US233623
申请日：1994-04-26
申请人： Heinz-Rudi Feist , Wilhelm Pohlmeyer , Joachim Frehse , Werner Rudolph , Max Braun , Kerstin Eichholz
发明人： Heinz-Rudi Feist , Wilhelm Pohlmeyer , Joachim Frehse , Werner Rudolph , Max Braun , Kerstin Eichholz
IPC分类号： B01J31/04 , C07B61/00 , C07C67/14 , C07C69/14 , C07C69/145 , C07C69/157 , C07C69/24 , C07C69/63 , C07C69/76 , C07C69/767 , C07C211/63 , C07C67/00
CPC分类号： C07C211/63 , C07C67/14
摘要： A process for preparing carboxylic esters from carboxylic acid halides or carboxylic anhydrides by reacting one of these starting materials with an alcohol under the catalytic action of "onium" or metal salts of carboxylic acids to obtain high yields of products in anhydrous form in a technically simple manner. The process is especially well suited for preparing 1,1,1-trifluoroethyl trifluoroacetate.
摘要翻译：通过使这些原料之一与醇在“鎓”或羧酸金属盐的催化作用下反应从羧酸卤化物或羧酸酐制备羧酸酯的方法，以技术上简单的方式获得无水形式的高产率产物方式。该方法特别适用于制备1,1,1-三氟乙基三氟乙酸盐。

8. 发明授权

US06583313B1 Two phase preparation of carboxylic acid esters 失效
标题翻译：羧酸酯的两相制备
公开(公告)号：US06583313B1
公开(公告)日：2003-06-24
申请号：US09113547
申请日：1998-07-10
申请人： Max Braun , Kerstin Eichholz , Werner Rudolph
发明人： Max Braun , Kerstin Eichholz , Werner Rudolph
IPC分类号： C07C6708
CPC分类号： C07C67/14 , C07C69/63
摘要： The methyl and ethyl esters of trifluoroacetic acid or chlorodifluoroacetic acid can be prepared in a technically simple manner from the corresponding acid chlorides and methanol or ethanol, respectively, in the presence of an “onium” salt of the acid as a catalyst. The alcohol is used in a stoichiometric excess, namely the molar ratio of alcohol to acid chloride is selected such that operation is in the region of a two-phase reaction. One of the phases is formed by the desired ester product, which is obtained in a high purity without any distillation.
摘要翻译：在酸的“鎓”盐作为催化剂存在下，三氟乙酸或氯代二氟乙酸的甲酯和乙酯可以分别由相应的酰氯和甲醇或乙醇以技术上简单的方式制备。醇以化学计量过量使用，即选择醇与酰氯的摩尔比，使得操作在两相反应的区域。其中一个阶段由所需的酯产物形成，其在没有任何蒸馏的情况下以高纯度获得。

9. 发明授权

US5545298A Process for preparing polyfluorocarboxylic acid chlorides and perfluorocarboxylic acid chlorides 失效
标题翻译：制备多氟羧酸氯化物和全氟羧酸氯化物的方法
公开(公告)号：US5545298A
公开(公告)日：1996-08-13
申请号：US288070
申请日：1994-08-10
申请人： Max Braun , Werner Rudolph , Kerstin Eichholz
发明人： Max Braun , Werner Rudolph , Kerstin Eichholz
IPC分类号： C07C51/58 , C07C53/48 , C07C53/50 , C07B33/00
CPC分类号： C07C51/58
摘要： A process for preparing compounds corresponding to the formula RCFXC(O)Cl, in which X is fluorine or chlorine and R is fluorine or a perfluorinated C1- C10-alkyl group, preferably chlorodifluoroacetyl chloride, by photochemical oxidation of R122 (CF.sub.2 ClCHCl.sub.2) and the preparation of trifluoroacetyl chloride by photochemical oxidation of R123 (CF.sub.3 CHCl.sub.2) with oxygen under irradiation. The reaction is preferably carried out without pressurization and without addition of elemental chlorine.
摘要翻译：通过R122（CF2ClCHCl2）的光化学氧化制备对应于式RCFXC（O）Cl的化合物的方法，其中X是氟或氯，R是氟或全氟化的C 1-10烷基，优选氯二氟乙酰氯通过R123（CF3CHCl2）与氧照射下的光化学氧化制备三氟乙酰氯。反应优选在不加压且不加入元素氯的情况下进行。

10. 发明授权

US06489510B1 Production of carboxylic acid fluorides 失效
标题翻译：羧酸氟化物的生产
公开(公告)号：US06489510B1
公开(公告)日：2002-12-03
申请号：US09319451
申请日：1999-07-29
申请人： Max Braun , Kerstin Eichholz , Werner Rudolph
发明人： Max Braun , Kerstin Eichholz , Werner Rudolph
IPC分类号： C07C5338
CPC分类号： C07C51/60 , B01J19/02 , B01J19/123 , B01J2219/00078 , B01J2219/0245 , B01J2219/0254 , B01J2219/0875 , C07C51/58 , C07C53/50 , C07C53/48 , C07C53/46
摘要： A method for producing carboxylic acid fluorides of the formula RCFXC(O)F, where X represents fluorine or chlorine, in good yields and with good selectivity for the carboxylic acid fluorides by reacting compounds of the formula RCFXCHFCl with oxygen by photochemical oxidation in the gaseous phase, preferably under sensitization with chlorine and using light having a wavelength &lgr;≧280 nm, which conditions make it possible to work without the use of pressure. Glass apparatus may be covered with a protective coating so as to protect it against traces of hydrogen fluoride. To this end, for example, heat-shrinkable sleeves made of light-permeable hydrogen fluoride-resistant material may be used. Polytetrafluoroethylene, polyfluoropropylene or a mixture thereof are especially suitable for this purpose. This type of protection is also suitable for other reactions such as photo-induced fluoro-dediazonation in hydrogen fluoride/pyridine for the production of aromatic compounds fluorinated in the nucleus or the oxidation of CHCl2 groups for the production of carboxylic acid chlorides.
摘要翻译：通过使式RCFXCHFCl的化合物与氧通过光化学氧化反应生成式RCFXC（O）F的羧酸氟化物的方法，其中X表示氟或氯，以良好的产率和对羧酸氟化物具有良好的选择性相，优选用氯敏感并使用波长λ= 280nm的光，该条件使得可以在不使用压力的情况下工作。玻璃装置可以用保护涂层覆盖，以保护其免受痕量的氟化氢。为此，例如，可以使用由透光耐氟化氢材料制成的热收缩套筒。聚四氟乙烯，聚氟丙烯或其混合物特别适用于此目的。这种类型的保护也适用于其它反应，例如在氟化氢/吡啶中用于生产在核中氟化的芳族化合物的光引发的氟 - 重氮化或用于生产羧酸氯化物的CHCl 2基团的氧化。

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