公开(公告)号：US20090143604A1

公开(公告)日：2009-06-04

申请号：US12274728

申请日：2008-11-20

申请人： Mario Joseph Nappa ,  Xuehui Sun ,  Lev Moiseevich Yagupolskii ,  Andrey Anatolievich Filatov ,  Vladimir Nikolaevich Boiko ,  Yurii Lvovich Yagupolskii

发明人： Mario Joseph Nappa ,  Xuehui Sun ,  Lev Moiseevich Yagupolskii ,  Andrey Anatolievich Filatov ,  Vladimir Nikolaevich Boiko ,  Yurii Lvovich Yagupolskii

IPC分类号： C07F3/06 ,  C07C17/26 ,  C07C69/02

CPC分类号： C07C17/00 ,  C07C17/2637 ,  C07C29/40 ,  C07C29/68 ,  C07C31/24 ,  C07C67/08 ,  C07C69/003 ,  C07F3/003 ,  C07C21/18 ,  C07C69/63 ,  C07C31/34

摘要： Described herein is a process for the manufacture of hydrofluoroalkanols of the structure RfCFClCHROH, comprising reacting a halofluorocarbon of the structure RfCFX2, wherein each X is independently selected from Cl, Br, and I, with an aldehyde and a reactive metal in a reaction solvent to generate a reaction product comprising a metal hydrofluoroalkoxide, neutralizing said metal hydrofluoroalkoxide to produce a hydrofluoroalkanol, and recovering the hydrofluoroalkanol. Also described herein are methods of manufacturing hydrofluoroalkenes of the structure RfCF═CHR from halofluorocarbons of the structure RfCFX2, wherein each X is independently selected from Cl, Br, and I, comprising (1) reacting halofluorocarbons of the structure RfCFX2, wherein each X is independently selected from Cl, Br, and I, with an aldehyde and a reactive metal to generate a reaction product comprising a metal hydrofluoroalkoxide, and reductively dehydroxyhalogenating said metal hydrofluoroalkoxide to produce a hydrofluoroalkene or (2) reacting a hydrofluoroalkanol of the structure RfCFXCHROH or a hydrofluoroalkoxide of the structure RfCFXCHROMX, wherein M is a reactive metal in the +2 oxidation state, with a carboxylic acid anhydride and a reactive metal in a reaction solvent to form a hydrofluoroalkene and isolating the hydrofluoroalkene. In particular, 2,3,3,3,-tetrafluoro-1-propene may be manufactured with this process. Also described are compounds of the formula RfCFClCHROC(═O)R′.

摘要翻译： 本文描述了制备结构RfCFClCHROH的氢氟烷醇的方法，包括使结构RfCFX2的卤氟烃，其中每个X独立地选自Cl，Br和I与反应溶剂中的醛和反应性金属反应 产生包含金属氢氟烷氧化物的反应产物，中和所述金属氢氟烷氧化物以产生氢氟烷醇，并回收氢氟烷醇。 本文还描述了由结构RfCFX2的卤代氟化物制备结构RfCF-CHR的氢氟烯烃的方法，其中每个X独立地选自Cl，Br和I，其包括（1）使结构RfCFX2的卤代碳氟化合物，其中每个X是 独立地选自Cl，Br和I，与醛和活性金属反应生成包含金属氢氟烷氧化物的反应产物，还原性地将所述金属氢氟烷氧化物脱羟基卤化以产生氢氟烯烃，或（2）使结构RfCFXCHROH的氢氟烷醇或 结构RfCFXCHROMX的氢氟烷氧化物，其中M是+2氧化态的活性金属，在反应溶剂中与羧酸酐和反应性金属反应形成氢氟烯烃并分离氢氟烯烃。 特别地，可以用该方法制造2,3,3,3-四氟-1-丙烯。 还描述了式RfCFClCHROC（-O）R'的化合物。

公开(公告)号：US08299309B2

公开(公告)日：2012-10-30

申请号：US13270489

申请日：2011-10-11

申请人： Mario Joseph Nappa ,  Xuehui Sun ,  Lev Moiseevich Yagupolskii ,  Andrey Anatolievich Filatov ,  Vladimir Nikolaevich Boiko ,  Yurii Lvovich Yagupolskii

发明人： Mario Joseph Nappa ,  Xuehui Sun ,  Lev Moiseevich Yagupolskii ,  Andrey Anatolievich Filatov ,  Vladimir Nikolaevich Boiko ,  Yurii Lvovich Yagupolskii

IPC分类号： C07C17/00

CPC分类号： C07C17/00 ,  C07C17/2637 ,  C07C29/40 ,  C07C29/68 ,  C07C31/24 ,  C07C67/08 ,  C07C69/003 ,  C07F3/003 ,  C07C21/18 ,  C07C69/63 ,  C07C31/34

摘要： Described herein is a process for the manufacture of hydrofluoroalkanols of the structure RfCFClCHROH. Also described herein are methods of manufacturing hydrofluoroalkenes of the structure RfCF═CHR from halofluorocarbons of the structure RfCFX2. In particular, 2,3,3,3,-tetrafluoro-1-propene may be manufactured with this process. Also described are compounds of the formula RfCFClCHROC(═O)R′.

摘要翻译： 本文描述了制备结构RfCFClCHROH的氢氟烷醇的方法。 本文还描述了从结构RfCFX2的卤代氟烃制备结构RfCF = CHR的氢氟烯烃的方法。 特别地，可以用该方法制造2,3,3,3-四氟-1-丙烯。 还描述了式RfCFClCHROC（= O）R'的化合物。

公开(公告)号：US20120083619A1

公开(公告)日：2012-04-05

申请号：US13270489

申请日：2011-10-11

申请人： Mario Joseph Nappa ,  Xuehui Sun ,  Lev Moiseevich Yagupolskii ,  Andrey Anatolievich Filatov ,  Vladimir Nikolaevich Boiko ,  Yurii Lvovich Yagupolskii

发明人： Mario Joseph Nappa ,  Xuehui Sun ,  Lev Moiseevich Yagupolskii ,  Andrey Anatolievich Filatov ,  Vladimir Nikolaevich Boiko ,  Yurii Lvovich Yagupolskii

IPC分类号： C07F3/06 ,  C07C67/08 ,  C07C17/23 ,  C07C23/06 ,  C07C29/38 ,  C07C69/14

CPC分类号： C07C17/00 ,  C07C17/2637 ,  C07C29/40 ,  C07C29/68 ,  C07C31/24 ,  C07C67/08 ,  C07C69/003 ,  C07F3/003 ,  C07C21/18 ,  C07C69/63 ,  C07C31/34

摘要： Described herein is a process for the manufacture of hydrofluoroalkanols of the structure RfCFClCHROH. Also described herein are methods of manufacturing hydrofluoroalkenes of the structure RfCF═CHR from halofluorocarbons of the structure RfCFX2. In particular, 2,3,3,3,-tetrafluoro-1-propene may be manufactured with this process. Also described are compounds of the formula RfCFClCHROC(═O)R′.

摘要翻译： 本文描述了制备结构RfCFClCHROH的氢氟烷醇的方法。 本文还描述了从结构RfCFX2的卤代氟烃制备结构RfCF = CHR的氢氟烯烃的方法。 特别地，可以用该方法制造2,3,3,3-四氟-1-丙烯。 还描述了式RfCFClCHROC（= O）R'的化合物。

公开(公告)号：US08058488B2

公开(公告)日：2011-11-15

申请号：US12274728

申请日：2008-11-20

申请人： Mario Joseph Nappa ,  Xuehui Sun ,  Lev Moiseevich Yagupolskii ,  Andrey Anatolievich Filatov ,  Vladimir Nikolaevich Boiko ,  Yurii Lvovich Yagupolskii

发明人： Mario Joseph Nappa ,  Xuehui Sun ,  Lev Moiseevich Yagupolskii ,  Andrey Anatolievich Filatov ,  Vladimir Nikolaevich Boiko ,  Yurii Lvovich Yagupolskii

IPC分类号： C07C17/00

CPC分类号： C07C17/00 ,  C07C17/2637 ,  C07C29/40 ,  C07C29/68 ,  C07C31/24 ,  C07C67/08 ,  C07C69/003 ,  C07F3/003 ,  C07C21/18 ,  C07C69/63 ,  C07C31/34

摘要： Described herein is a process for the manufacture of hydrofluoroalkanols of the structure RfCFClCHROH, comprising reacting a halofluorocarbon of the structure RfCFX2, wherein each X is independently selected from Cl, Br, and I, with an aldehyde and a reactive metal in a reaction solvent to generate a reaction product comprising a metal hydrofluoroalkoxide, neutralizing said metal hydrofluoroalkoxide to produce a hydrofluoroalkanol, and recovering the hydrofluoroalkanol. Also described herein are methods of manufacturing hydrofluoroalkenes of the structure RfCF═CHR from halofluorocarbons of the structure RfCFX2, wherein each X is independently selected from Cl, Br, and I, comprising (1) reacting halofluorocarbons of the structure RfCFX2, wherein each X is independently selected from Cl, Br, and I, with an aldehyde and a reactive metal to generate a reaction product comprising a metal hydrofluoroalkoxide, and reductively dehydroxyhalogenating said metal hydrofluoroalkoxide to produce a hydrofluoroalkene or (2) reacting a hydrofluoroalkanol of the structure RfCFXCHROH or a hydrofluoroalkoxide of the structure RfCFXCHROMX, wherein M is a reactive metal in the +2 oxidation state, with a carboxylic acid anhydride and a reactive metal in a reaction solvent to form a hydrofluoroalkene and isolating the hydrofluoroalkene. In particular, 2,3,3,3,-tetrafluoro-1-propene may be manufactured with this process. Also described are compounds of the formula RfCFClCHROC(═O)R′.

摘要翻译： 本文描述了制备结构RfCFClCHROH的氢氟烷醇的方法，包括使结构RfCFX2的卤氟烃，其中每个X独立地选自Cl，Br和I与反应溶剂中的醛和反应性金属反应 产生包含金属氢氟烷氧化物的反应产物，中和所述金属氢氟烷氧化物以产生氢氟烷醇，并回收氢氟烷醇。 本文还描述了从结构RfCFX2的卤代氟化物制备结构RfCF = CHR的氢氟烯烃的方法，其中每个X独立地选自Cl，Br和I，其包括（1）使结构RfCFX2的卤代碳氟化合物，其中每个X是 独立地选自Cl，Br和I，与醛和活性金属反应生成包含金属氢氟烷氧化物的反应产物，还原性地将所述金属氢氟烷氧化物脱羟基卤化以产生氢氟烯烃，或（2）使结构RfCFXCHROH的氢氟烷醇或 结构RfCFXCHROMX的氢氟烷氧化物，其中M是+2氧化态的活性金属，在反应溶剂中与羧酸酐和反应性金属反应形成氢氟烯烃并分离氢氟烯烃。 特别地，可以用该方法制造2,3,3,3-四氟-1-丙烯。 还描述了式RfCFClCHROC（= O）R'的化合物。

公开(公告)号：US08518294B2

公开(公告)日：2013-08-27

申请号：US13405657

申请日：2012-02-27

申请人： Mario Joseph Nappa ,  Xuehui Sun

发明人： Mario Joseph Nappa ,  Xuehui Sun

IPC分类号： C09K5/04

CPC分类号： C09K5/045 ,  C09K2205/126

摘要： Compositions comprising CF3CClFCH2OH, CF3CClFCH2OZnCl, and CF3CClFCH2OC(═O)CH3 are useful in processes to make HFO-1234yf. Compositions comprising HFO-1234yf may comprise at least one additional compound selected from the group consisting of CFC-114a, HCFC-124, HFC-143a, CFO-1113, HFO-1123, HFO-1132a, tetrafluoroethene, HCFO-1122, 3,4,4,4-tetrafluoro-2-butanone, acetyl fluoride, 2-chloro-2,3,3,3-tetrafluoropropanol, 2-chloro-2,3,3,3-tetrafluoropropyl acetate, Zinc (2-chloro-2,3,3,3-tetrafluoropropoxy) chloride, 2-chloro-2,3,3,3-tetrafluoropropoxy methyl acetate, 1,3-bistrifluoromethyl-1,3-difluorocyclobutane, 2,3,3,3-tetrafluoropropyl acetate, dimethylformamide, pyridine, ethyl acetate, acetic acid, diethyl ether, acetic anhydride, methyl acetate, dimethylacetamide, methanol, ethanol, methyl formate, pyrazine, pyrimidine, N-methylpyrrolidine, N-methylpiperidine, hexamethylphosphoramide, tetrahydrofuran, 1,4-dioxane, N-methylpyrrolidinone, dimethyl sulfoxide, acetonitrile, benzonitrile, and mixtures thereof. Compositions comprising HFO-1234yf are useful, among other uses, as heat transfer compositions for use in refrigeration, air-conditioning and heat pump systems.

摘要翻译： 包含CF 3 CClFCH 2 OH，CF 3 CClFCH 2 OZnCl和CF 3 CClFCH 2 OC（= O）CH 3的组合物可用于制备HFO-1234yf的方法中。 包含HFO-1234yf的组合物可以包含至少一种选自CFC-114a，HCFC-124，HFC-143a，CFO-1113，HFO-1123，HFO-1132a，四氟乙烯，HCFO-1122,3， 4,4,4-四氟-2-丁酮，乙酰氟，2-氯-2,3,3,3-四氟丙醇，2-氯-2,3,3,3-四氟丙基乙酸酯，锌（2-氯 - 2,3,3,3-四氟丙氧基）氯化物，2-氯-2,3,3,3-四氟丙氧基甲酸乙酯，1,3-双三氟甲基-1,3-二氟环丁烷，乙酸2,3,3,3-四氟丙酯 吡啶，乙酸乙酯，乙酸甲酯，二甲基乙酰胺，甲醇，乙醇，甲酸甲酯，吡嗪，嘧啶，N-甲基吡咯烷，N-甲基哌啶，六甲基磷酰胺，四氢呋喃，1,4-二恶烷 ，N-甲基吡咯烷酮，二甲基亚砜，乙腈，苄腈及其混合物。 包括HFO-1234yf的组合物在其它用途中可用作用于制冷，空调和热泵系统的热传递组合物。

公开(公告)号：US20120168672A1

公开(公告)日：2012-07-05

申请号：US13405657

申请日：2012-02-27

申请人： Mario Joseph Nappa ,  Xuehui Sun

发明人： Mario Joseph Nappa ,  Xuehui Sun

IPC分类号： C09K5/00

CPC分类号： C09K5/045 ,  C09K2205/126

摘要： Compositions comprising CF3CClFCH2OH, CF3CClFCH2OZnCl, and CF3CClFCH2OC(═O)CH3 are useful in processes to make HFO-1234yf. Compositions comprising HFO-1234yf may comprise at least one additional compound selected from the group consisting of CFC-114a, HCFC-124, HFC-143a, CFO-1113, HFO-1123, HFO-1132a, tetrafluoroethene, HCFO-1122, 3,4,4,4-tetrafluoro-2-butanone, acetyl fluoride, 2-chloro-2,3,3,3-tetrafluoropropanol, 2-chloro-2,3,3,3-tetrafluoropropyl acetate, Zinc (2-chloro-2,3,3,3-tetrafluoropropoxy)chloride, 2-chloro-2,3,3,3-tetrafluoropropoxy methyl acetate, 1,3-bistrifluoromethyl-1,3-difluorocyclobutane, 2,3,3,3-tetrafluoropropyl acetate, dimethylformamide, pyridine, ethyl acetate, acetic acid, diethyl ether, acetic anhydride, methyl acetate, dimethylacetamide, methanol, ethanol, methyl formate, pyrazine, pyrimidine, N-methylpyrrolidine, N-methylpiperidine, hexamethylphosphoramide, tetrahydrofuran, 1,4-dioxane, N-methylpyrrolidinone, dimethyl sulfoxide, acetonitrile, benzonitrile, and mixtures thereof. Compositions comprising HFO-1234yf are useful, among other uses, as heat transfer compositions for use in refrigeration, air-conditioning and heat pump systems.

摘要翻译： 包含CF 3 CClFCH 2 OH，CF 3 CClFCH 2 OZnCl和CF 3 CClFCH 2 OC（= O）CH 3的组合物可用于制备HFO-1234yf的方法中。 包含HFO-1234yf的组合物可以包含至少一种选自CFC-114a，HCFC-124，HFC-143a，CFO-1113，HFO-1123，HFO-1132a，四氟乙烯，HCFO-1122,3， 4,4,4-四氟-2-丁酮，乙酰氟，2-氯-2,3,3,3-四氟丙醇，2-氯-2,3,3,3-四氟丙基乙酸酯，锌（2-氯 - 2,3,3,3-四氟丙氧基）氯化物，2-氯-2,3,3,3-四氟丙氧基甲酸乙酯，1,3-双三氟甲基-1,3-二氟环丁烷，乙酸2,3,3,3-四氟丙酯 吡啶，乙酸乙酯，乙酸甲酯，二甲基乙酰胺，甲醇，乙醇，甲酸甲酯，吡嗪，嘧啶，N-甲基吡咯烷，N-甲基哌啶，六甲基磷酰胺，四氢呋喃，1,4-二恶烷 ，N-甲基吡咯烷酮，二甲基亚砜，乙腈，苄腈及其混合物。 包括HFO-1234yf的组合物在其它用途中可用作用于制冷，空调和热泵系统的热传递组合物。

公开(公告)号：US20140012048A9

公开(公告)日：2014-01-09

申请号：US13397967

申请日：2012-02-16

申请人： Xuehui Sun ,  Mario Joseph Nappa

发明人： Xuehui Sun ,  Mario Joseph Nappa

IPC分类号： C07C21/18

CPC分类号： C07C17/25 ,  B01J21/18 ,  B01J37/06 ,  B01J37/084 ,  C07C21/18

摘要： A dehydrochlorination process is disclosed. The process involves contacting RfCHClCH2Cl with a carbon catalyst in a reaction zone to produce a product mixture comprising RfCCl═CH2, wherein Rf is a perfluorinated alkyl group.

摘要翻译： 公开了一种脱氯化氢方法。 该方法包括在反应区中将RfCHClCH2Cl与碳催化剂接触以产生包含RfCCl = CH 2的产物混合物，其中Rf是全氟化烷基。

公开(公告)号：US20120215037A1

公开(公告)日：2012-08-23

申请号：US13370337

申请日：2012-02-10

申请人： XUEHUI SUN ,  Mario Joseph Nappa

发明人： XUEHUI SUN ,  Mario Joseph Nappa

IPC分类号： C07C17/25

CPC分类号： C07C17/25 ,  C07C21/18

摘要： A dehydrochlorination process is disclosed. The process involves contacting RfCFClCH2X with a catalyst in a reaction zone to produce a product mixture comprising RfCF═CHX, wherein said catalyst comprises MY supported on carbon, and wherein Rf is a perfluorinated alkyl group, X═H, F, Cl, Br or I, M=K, Na or Cs, and Y═F, Cl or Br.

摘要翻译： 公开了一种脱氯化氢方法。 该方法包括使RfCFClCH 2 X与反应区中的催化剂接触以产生包含RfCF = CHX的产物混合物，其中所述催化剂包含负载在碳上的MY，其中Rf是全氟化烷基，X = H，F，Cl，Br或 I，M = K，Na或Cs，Y = F，Cl或Br。

公开(公告)号：US20120215036A1

公开(公告)日：2012-08-23

申请号：US13397967

申请日：2012-02-16

申请人： Xuehui Sun ,  Mario Joseph Nappa

发明人： Xuehui Sun ,  Mario Joseph Nappa

IPC分类号： C07C21/18

CPC分类号： C07C17/25 ,  B01J21/18 ,  B01J37/06 ,  B01J37/084 ,  C07C21/18

摘要： A dehydrochlorination process is disclosed. The process involves contacting RfCHClCH2Cl with a carbon catalyst in a reaction zone to produce a product mixture comprising RfCCl═CH2, wherein Rf is a perfluorinated alkyl group.

摘要翻译： 公开了一种脱氯化氢方法。 该方法涉及使RfCHClCH2Cl与反应区中的碳催化剂接触以产生包含RfCCl = CH 2的产物混合物，其中Rf是全氟化烷基。

公开(公告)号：US08247625B2

公开(公告)日：2012-08-21

申请号：US12307754

申请日：2007-07-03

申请人： Xuehui Sun ,  Viacheslav A. Petrov ,  Mario Joseph Nappa ,  Velliyur Nott Mallikarjuna Rao ,  Ekaterina N. Swearingen

发明人： Xuehui Sun ,  Viacheslav A. Petrov ,  Mario Joseph Nappa ,  Velliyur Nott Mallikarjuna Rao ,  Ekaterina N. Swearingen

IPC分类号： C07C17/266 ,  C07C17/26

CPC分类号： C07C17/278 ,  C07C19/08

摘要： A process is disclosed for making RR1R2CCR1R2F wherein R is selected from the group consisting of CH3, CH2F, C2H4F, and F(CF2)nCH2CH2 where n is an integer from 1 to 10, each R1 is independently selected from the group consisting of H, Cl, F and CF3, and each R2 is independently selected from the group consisting of H, F and CF3. The process involves reacting RF with R1R2C═CR1R2 in the presence of SbF5 to produce a product mixture comprising RR1R2CCR1R2F, wherein the reaction temperature is from about −60° C. to about −10° C., provided that total number of carbon atoms in R1R2C═CR1R2 is 5 or less.

摘要翻译： 公开了制备RR1R2CCR1R2F的方法，其中R选自CH 3，CH 2 F，C 2 H 4 F和F（CF 2）n CH 2 CH 2，其中n为1至10的整数，每个R 1独立地选自H， Cl，F和CF 3，并且每个R 2独立地选自H，F和CF 3。 该方法包括在SbF 5存在下使RF与R 1 R 2 C = CR 1 R 2反应以产生包含RR1R2CCR1R2F的产物混合物，其中反应温度为约-60℃至约-10℃，条件是总碳原子数 R1R2C=CR1R2为5以下。