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1. 发明授权

US10059647B2 Method for producing fluorinated organic compounds 有权
公开(公告)号：US10059647B2
公开(公告)日：2018-08-28
申请号：US14269251
申请日：2014-05-05
申请人： Sudip Mukhopadhyay , Hsueh S. Tung , Michael Van Der Puy , Daniel C. Merkel , Jing Ji Ma , Cheryl L. Bortz , Barbara A. Light , Steven D. Phillips , Rajesh K. Dubey
发明人： Sudip Mukhopadhyay , Hsueh S. Tung , Michael Van Der Puy , Daniel C. Merkel , Jing Ji Ma , Cheryl L. Bortz , Barbara A. Light , Steven D. Phillips , Rajesh K. Dubey
IPC分类号： C07C17/25 , C07C17/10 , C07C17/087 , C07C17/20 , C07C17/21
CPC分类号： C07C17/25 , C07C17/00 , C07C17/04 , C07C17/087 , C07C17/10 , C07C17/20 , C07C17/204 , C07C17/206 , C07C17/21 , C07C17/26 , C07C17/269 , C07C17/272 , C07C17/278 , C07C21/18 , C07C19/01 , C07C19/10 , C07C19/08 , C07C21/073 , C07C21/04
摘要： Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF═CH2 (1234yf). Three steps may be used in preferred embodiments in which a feedstock such as CCl2═CClCH2Cl (which may be purchased or synthesized from 1,2,3-trichloropropane) is fluorinated (preferably with HF in gas-phase in the presence of a catalyst) to synthesize a compound such as CF3CCl═CH2, preferably in a 80-96% selectivity. The CF3CCl═CH2 is preferably converted to CF3CFClCH3 (244-isomer) using a SbCl5 as the catalyst which is then transformed selectively to 1234yf, preferably in a gas-phase catalytic reaction using activated carbon as the catalyst. For the first step, a mixture of Cr2O3 and FeCl3/C is preferably used as the catalyst to achieve high selectivity to CF3CCl═CH2 (96%). In the second step, SbCl5/C is preferably used as the selective catalyst for transforming 1233xf to 244-isomer, CF3CFClCH3. The intermediates are preferably isolated and purified by distillation and used in the next step without further purification, preferably to a purity level of greater than about 95%.

2. 发明授权

US08084653B2 Method for producing fluorinated organic compounds 有权
标题翻译：氟化有机化合物的制备方法
公开(公告)号：US08084653B2
公开(公告)日：2011-12-27
申请号：US11619592
申请日：2007-01-03
申请人： Hsueh S. Tung , Sudip Mukhopadhyay , Michael Van Der Puy , Daniel C. Merkel , Jing Ji Ma , Cheryl L. Bortz , Barbara A. Light , Steven D. Phillips , Rajesh K. Dubey
发明人： Hsueh S. Tung , Sudip Mukhopadhyay , Michael Van Der Puy , Daniel C. Merkel , Jing Ji Ma , Cheryl L. Bortz , Barbara A. Light , Steven D. Phillips , Rajesh K. Dubey
IPC分类号： C07C17/00 , C07C19/08 , C07C21/18 , C07C23/00 , C07C25/13
CPC分类号： C07C17/25 , C07C17/00 , C07C17/04 , C07C17/087 , C07C17/10 , C07C17/20 , C07C17/204 , C07C17/206 , C07C17/21 , C07C17/26 , C07C17/269 , C07C17/272 , C07C17/278 , C07C21/18 , C07C19/01 , C07C19/10 , C07C19/08 , C07C21/073 , C07C21/04
摘要： Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF═CH2 (1234yf). Three steps may be used in preferred embodiments in which a feedstock such as CCl2═CClCH2Cl (which may be purchased or synthesized from 1,2,3-trichloropropane) is fluorinated (preferably with HF in gas-phase in the presence of a catalyst) to synthesize a compound such as CF3CCl═CH2, preferably in a 80-96% selectivity. The CF3CCl═CH2 is preferably converted to CF3CFClCH3 (244-isomer) using a SbCl5 as the catalyst which is then transformed selectively to 1234yf, preferably in a gas-phase catalytic reaction using activated carbon as the catalyst. For the first step, a mixture of Cr2O3 and FeCl3/C is preferably used as the catalyst to achieve high selectivity to CF3CCl═CH2 (96%). In the second step, SbCl5/C is preferably used as the selective catalyst for transforming 1233xf to 244-isomer, CF3CFClCH3. The intermediates are preferably isolated and purified by distillation and used in the next step without further purification, preferably to a purity level of greater than about 95%.
摘要翻译：公开了用于生产氟化烯烃的方法，优选适于CF 3CF≡CH2（1234yf）的商业化。在优选实施方案中可以使用三个步骤，其中诸如CCl 2 = CClCH 2 Cl（其可以从1,2,3-三氯丙烷购买或合成）的原料被氟化（优选在气相存在下在HF的情况下为催化剂）合成化合物如CF 3 CCl = CH 2，优选选择性为80-96％。 CF 3 CCl = CH 2优选使用SbCl 5作为催化剂转化为CF 3 CFClCH 3（244-异构体），然后将其选择性地转化为1234yf，优选在使用活性炭作为催化剂的气相催化反应中。对于第一步，优选使用Cr 2 O 3和FeCl 3 / C的混合物作为催化剂以实现对CF 3 CCl = CH 2（96％）的高选择性。在第二步中，SbCl 5 / C优选用作用于将1233xf转化为244-异构体CF 3 CFClCH 3的选择性催化剂。中间体优选通过蒸馏分离和纯化，并用于下一步骤而不进一步纯化，优选纯度高于约95％。

3. 发明申请

US20150315108A1 METHOD FOR PRODUCING FLUORINATED ORGANIC COMPOUNDS 审中-公开
标题翻译：生产氟化有机化合物的方法
公开(公告)号：US20150315108A1
公开(公告)日：2015-11-05
申请号：US14269251
申请日：2014-05-05
申请人： SUDIP MUKHOPADHYAY , Hsueh S. Tung , Michael Van der Puy , Daniel C. Merkel , Jing Ji Ma , Cheryl L. Bortz , Barbara A. Light , Steven D. Phillips , Rajesh K. Dubey
发明人： SUDIP MUKHOPADHYAY , Hsueh S. Tung , Michael Van der Puy , Daniel C. Merkel , Jing Ji Ma , Cheryl L. Bortz , Barbara A. Light , Steven D. Phillips , Rajesh K. Dubey
IPC分类号： C07C17/20
CPC分类号： C07C17/25 , C07C17/00 , C07C17/04 , C07C17/087 , C07C17/10 , C07C17/20 , C07C17/204 , C07C17/206 , C07C17/21 , C07C17/26 , C07C17/269 , C07C17/272 , C07C17/278 , C07C21/18 , C07C19/01 , C07C19/10 , C07C19/08 , C07C21/073 , C07C21/04
摘要： Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF═CH2 (1234yf). Three steps may be used in preferred embodiments in which a feedstock such as CCl2═CClCH2Cl (which may be purchased or synthesized from 1,2,3-trichloropropane) is fluorinated (preferably with HF in gas-phase in the presence of a catalyst) to synthesize a compound such as CF3CCl═CH2, preferably in a 80-96% selectivity. The CF3CCl═CH2 is preferably converted to CF3CFClCH3 (244-isomer) using a SbCl5 as the catalyst which is then transformed selectively to 1234yf, preferably in a gas-phase catalytic reaction using activated carbon as the catalyst. For the first step, a mixture of Cr2O3 and FeCl3/C is preferably used as the catalyst to achieve high selectivity to CF3CCl═CH2 (96%). In the second step, SbCl5/C is preferably used as the selective catalyst for transforming 1233xf to 244-isomer, CF3CFClCH3. The intermediates are preferably isolated and purified by distillation and used in the next step without further purification, preferably to a purity level of greater than about 95%.
摘要翻译：公开了用于生产氟化烯烃的方法，优选适于CF 3CF≡CH2（1234yf）的商业化。在优选实施方案中可以使用三个步骤，其中诸如CCl 2 = CClCH 2 Cl（其可以由1,2,3-三氯丙烷购买或合成）的原料被氟化（优选在气相存在下，在HF的存在下）合成化合物如CF 3 CCl = CH 2，优选选择性为80-96％。 CF 3 CCl = CH 2优选使用SbCl 5作为催化剂转化为CF 3 CFClCH 3（244-异构体），然后将其选择性地转化为1234yf，优选在使用活性炭作为催化剂的气相催化反应中。对于第一步，优选使用Cr 2 O 3和FeCl 3 / C的混合物作为催化剂，以实现对CF 3 CCl = CH 2（96％）的高选择性。在第二步中，SbCl 5 / C优选用作用于将1233xf转化为244-异构体CF 3 CFClCH 3的选择性催化剂。中间体优选通过蒸馏分离和纯化，并用于下一步骤而不进一步纯化，优选纯度高于约95％。

4. 发明授权

US08754271B2 Method for producing fluorinated organic compounds 有权
标题翻译：氟化有机化合物的制备方法
公开(公告)号：US08754271B2
公开(公告)日：2014-06-17
申请号：US13302849
申请日：2011-11-22
申请人： Sudip Mukhopadhyay , Hsueh S. Tung , Michael Van Der Puy , Daniel C. Merkel , Jing Ji Ma , Cheryl L. Bortz , Barbara A. Light , Steven D. Phillips , Rajesh K. Dubey
发明人： Sudip Mukhopadhyay , Hsueh S. Tung , Michael Van Der Puy , Daniel C. Merkel , Jing Ji Ma , Cheryl L. Bortz , Barbara A. Light , Steven D. Phillips , Rajesh K. Dubey
IPC分类号： C07C17/00 , C07C19/08 , C07C21/18 , C07C23/00 , C07C25/13
CPC分类号： C07C17/25 , C07C17/00 , C07C17/04 , C07C17/087 , C07C17/10 , C07C17/20 , C07C17/204 , C07C17/206 , C07C17/21 , C07C17/26 , C07C17/269 , C07C17/272 , C07C17/278 , C07C21/18 , C07C19/01 , C07C19/10 , C07C19/08 , C07C21/073 , C07C21/04
摘要： Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF═CH2 (1234yf). Three steps may be used in preferred embodiments in which a feedstock such as CCl2═CClCH2Cl is fluorinated to synthesize a compound such as CF3CCl═CH2. The CF3CCl═CH2 is preferably converted to CF3CFClCH3 (244-isomer) using a SbCl5 as the catalyst which is then transformed selectively to 1234yf. For the first step, a mixture of Cr2O3 and FeCl3/C is preferably used as the catalyst to achieve high selectivity to CF3CCl═CH2 (96%). In the second step, SbCl5/C is preferably used as the selective catalyst for transforming 1233xf to 244-isomer, CF3CFClCH3. The intermediates are preferably isolated and purified by distillation and used in the next step without further purification, preferably to a purity level of greater than about 95%.
摘要翻译：公开了用于生产氟化烯烃的方法，优选适于CF 3CF≡CH2（1234yf）的商业化。优选的实施方案中可以使用三个步骤，其中诸如CCl 2 = CClCH 2 Cl的原料被氟化以合成诸如CF 3 CCl = CH 2的化合物。 CF 3 CCl = CH 2优选使用SbCl 5作为催化剂转化为CF 3 CFClCH 3（244-异构体），然后将其选择性地转化为1234yf。对于第一步，优选使用Cr 2 O 3和FeCl 3 / C的混合物作为催化剂以实现对CF 3 CCl = CH 2（96％）的高选择性。在第二步中，SbCl 5 / C优选用作用于将1233xf转化为244-异构体CF 3 CFClCH 3的选择性催化剂。中间体优选通过蒸馏分离和纯化，并用于下一步骤而不进一步纯化，优选纯度高于约95％。

5. 发明授权

US07659434B2 Method for producing fluorinated organic compounds 有权
标题翻译：氟化有机化合物的制备方法
公开(公告)号：US07659434B2
公开(公告)日：2010-02-09
申请号：US11592415
申请日：2006-11-03
申请人： Sudip Mukhopadhyay , Haridasan K. Nair , Hsueh S. Tung , Michael Van Der Puy , Daniel C. Merkel , Rajesh K. Dubey , Jing Ji Ma , Barbara A. Light , Kim M. Fleming , Cheryl L. Bortz , Richard Udy
发明人： Sudip Mukhopadhyay , Haridasan K. Nair , Hsueh S. Tung , Michael Van Der Puy , Daniel C. Merkel , Rajesh K. Dubey , Jing Ji Ma , Barbara A. Light , Kim M. Fleming , Cheryl L. Bortz , Richard Udy
IPC分类号： C07C21/18
CPC分类号： C07C17/00 , C07C17/02 , C07C17/04 , C07C17/10 , C07C21/18 , C07C19/08 , C07C19/10
摘要： A method for preparing fluorinated organic compounds comprising contacting hydrogen fluoride with at least one compound of formula I: CX3CXYCH3 I where each X is independently Cl, I or Br, and each Y is independently H or F, said contacting step being carried out under conditions effective to produce a compound of formula II CF3CZCH2 II where Z is Cl, I, Br, or F.
摘要翻译：一种制备氟化有机化合物的方法，包括使氟化氢与至少一种式I化合物：CX3CXYCH3I接触，其中每个X独立地为Cl，I或Br，每个Y独立地为H或F，所述接触步骤在条件有效地制备式II化合物CF 3 CZCH 2 II，其中Z是Cl，I，Br或F.

6. 发明授权

US09102579B2 Method for producing fluorinated organic compounds 有权
标题翻译：氟化有机化合物的制备方法
公开(公告)号：US09102579B2
公开(公告)日：2015-08-11
申请号：US11619589
申请日：2007-01-03
申请人： Barbara A. Light , Steven D. Phillips , Kim M. Fleming , Susan A. Ferguson , Jing Ji Ma , Cheryl L. Bortz , Michael Van Der Puy , Daniel C. Merkel , Hsueh S. Tung , Sudip Mukhopadhyay
发明人： Barbara A. Light , Steven D. Phillips , Kim M. Fleming , Susan A. Ferguson , Jing Ji Ma , Cheryl L. Bortz , Michael Van Der Puy , Daniel C. Merkel , Hsueh S. Tung , Sudip Mukhopadhyay
IPC分类号： C07C17/00 , C07C19/08 , C07C21/18 , C07C23/00 , C07C25/13 , C07C17/21 , C07C17/087 , C07C17/10 , C07C17/20 , C07C17/25
CPC分类号： C07C17/23 , C07C17/087 , C07C17/10 , C07C17/206 , C07C17/21 , C07C17/25 , C07C19/08 , C07C19/10 , C07C21/18
摘要： Disclosed is a process for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of Formula (I): C(X)3CF2C(X)3 (I) to at least one compound of Formula (II) CF3CF═CHZ (II) where each X and Z is independently H, F, Cl, I or Br, said process preferably not including any substantial amount of oxygen-containing catalyst in certain embodiments. Preferably Z is H.
摘要翻译：公开了一种制备氟化有机化合物的方法，包括氢氟丙烯，其优选包括将至少一种式（I）化合物：C（X）3CF 2 C（X）3（I）转化为至少一种式（II）化合物CF 3 CF ≡CHZ（II）其中每个X和Z独立地为H，F，Cl，I或Br，在某些实施方案中，所述方法优选不包括任何显着量的含氧催化剂。 Z优选为

7. 发明授权

US09035111B2 Method for producing fluorinated organic compounds 有权
标题翻译：氟化有机化合物的制备方法
公开(公告)号：US09035111B2
公开(公告)日：2015-05-19
申请号：US12196207
申请日：2008-08-21
申请人： Sudip Mukhopadhyay , Cheryl L. Bortz , Kim M. Fleming , Steven D. Phillips , Rajesh K. Dubey
发明人： Sudip Mukhopadhyay , Cheryl L. Bortz , Kim M. Fleming , Steven D. Phillips , Rajesh K. Dubey
IPC分类号： C07C21/18 , C07C17/38 , C07C17/04 , C07C17/20 , C07C17/21 , C07C17/25
CPC分类号： C07C17/38 , C07C17/04 , C07C17/206 , C07C17/21 , C07C17/25 , C07C17/389 , C07C21/18 , C07C19/10 , C07C19/08
摘要： A method for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I): CF3(—CX2X2)nCX1═H2 (I) to at least one compound of formula (II): CF3(CX2X2)nCX1═H2 (II), where X1 is Cl, Br or I, each X2 is independently selected from the group consisting of H, Cl, F, Br or J, and n is 0, 1, or 2.
摘要翻译：包括氢氟丙烯的氟化有机化合物的制备方法，其优选包括将至少一种式（I）化合物：CF 3（-CX 2 X 2）n C X 1 = H 2（I）转化为至少一种式（II）的化合物：CF 3（CX 2 X 2 ）nCX1 = H 2（II），其中X 1为Cl，Br或I，每个X 2独立地选自H，Cl，F，Br或J，且n为0,1或2。

8. 发明申请

US20090203945A1 METHOD FOR PRODUCING FLUORINATED ORGANIC COMPOUNDS 有权
标题翻译：生产氟化有机化合物的方法
公开(公告)号：US20090203945A1
公开(公告)日：2009-08-13
申请号：US12196207
申请日：2008-08-21
申请人： Sudip Mukhopadhyay , Cheryl L. Bortz , Kim M. Fleming , Steven D. Phillips , Rajesh K. Dubey
发明人： Sudip Mukhopadhyay , Cheryl L. Bortz , Kim M. Fleming , Steven D. Phillips , Rajesh K. Dubey
IPC分类号： C07C21/18
CPC分类号： C07C17/38 , C07C17/04 , C07C17/206 , C07C17/21 , C07C17/25 , C07C17/389 , C07C21/18 , C07C19/10 , C07C19/08
摘要： A method for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I): CF3(—CX2X2)nCX1═H2 (I) to at least one compound of formula (II): CF3(CX2X2)nCX1═H2 (II), where X1 is Cl, Br or I, each X2 is independently selected from the group consisting of H, Cl, F, Br or J, and n is 0, 1, or 2.
摘要翻译：包括氢氟丙烯的氟化有机化合物的制备方法，其优选包括转化至少一种式（I）化合物：<？在线式描述=“在线式”末端=“铅”→CF 3（ - CX2X2）nCX1-H2（I）<β-in-line-formula description =“In-line Formulas”end =“tail”？>至少一种式（II）化合物：<？in-line-formula description = “直线公式”end =“lead”？> CF3（CX2X2）nCX1-H2（II），<？in-line-formula description =“In-line Formulas”end =“tail”？>其中X1为Cl ，Br或I，每个X 2独立地选自H，Cl，F，Br或J，且n为0,1或2。

9. 发明申请

US20090099396A1 PROCESS FOR SYNTHESIS OF FLUORINATED OLEFINS 有权
标题翻译：合成氟化烯烃的方法
公开(公告)号：US20090099396A1
公开(公告)日：2009-04-16
申请号：US12249958
申请日：2008-10-12
申请人： Sudip Mukhopadhyay , Cheryl L. Bortz , Barbara A. Light , Cheryl L. Cantlon , Robert C. Johnson
发明人： Sudip Mukhopadhyay , Cheryl L. Bortz , Barbara A. Light , Cheryl L. Cantlon , Robert C. Johnson
IPC分类号： C07C17/20
CPC分类号： C07C17/21 , C07C17/23 , C07C17/25 , C07C21/18 , C07C19/08
摘要： Disclosed is a process for the synthesis of fluorinated olefins, and in particularly preferred embodiments tetrafluorinated olefins having F on an unsaturated, non-terminal carbon, such as 2,3,3,3-tetrafluoropropene. The preferred processes of the present invention in accordance with one embodiment generally comprise: (a) reacting a compound of formula (I) X1X2 (I) with a compound of formula (II) CX1X2X3CX1═CX1X2 (II) to produce a reaction product comprising a compound of formula (III) CF3CHX1CH2X2 (III), and (b) exposing said compound of formula (III) to reaction conditions effective to convert said compound of formula (III) to a compound of formula (IV) CF3CZ=CH2 (IV) wherein X1, X2, and X3 are each independently selected from the group consisting of hydrogen, chlorine, bromine, fluorine and iodine, provided that X1 and X2 in formula (I) are not both hydrogen and Z is Cl, I, Br, or F.
摘要翻译：公开了用于合成氟化烯烃的方法，特别优选的实施方案中，在不饱和的非末端碳上具有F的四氟化烯烃如2,3,3,3-四氟丙烯。根据一个实施方案的本发明的优选方法通常包括：（a）使式（I）化合物<？in-line-formula description =“In-Line Formulas”end =“lead”→> X1X2 I）<？in-line-formula description =“In-line formula”end =“tail”？>与式（II）的化合物<？in-line-formula description =“In-line Formulas”end =“ 引线“→CX1X2X3CX1-CX1X2（II）<？在线公式描述=”内联式“末端=”尾“→产生包含式（III）化合物的反应产物 -formulae description =“In-line Formulas”end =“lead”？> CF3CHX1CH2X2（III）和<？in-line-formula description =“In-line Formulas”end =“tail”？>（b）式（III）化合物与有效将所述式（III）化合物转化成式（IV）化合物的反应条件<β在线式描述=“在线式”末端=“铅”→CF 3 CZ = CH2（IV）<？in-line-formula description =“In-line Formulas”end =“tail”？>其中X1，X2和X3各自独立式（I）中的X 1和X 2不同时为氢，Z为Cl，I，Br或F时，选自氢，氯，溴，氟和碘组成的组。

10. 发明授权

US09079818B2 Process for synthesis of fluorinated olefins 有权
标题翻译：合成氟化烯烃的方法
公开(公告)号：US09079818B2
公开(公告)日：2015-07-14
申请号：US12249958
申请日：2008-10-12
申请人： Sudip Mukhopadhyay , Cheryl L. Bortz , Barbara A. Light , Cheryl L. Cantlon , Robert C. Johnson
发明人： Sudip Mukhopadhyay , Cheryl L. Bortz , Barbara A. Light , Cheryl L. Cantlon , Robert C. Johnson
IPC分类号： C07C21/00 , C07C17/00 , C07C17/21 , C07C17/23 , C07C17/25 , C07C21/18
CPC分类号： C07C17/21 , C07C17/23 , C07C17/25 , C07C21/18 , C07C19/08
摘要： Disclosed is a process for the synthesis of fluorinated olefins, and in particularly preferred embodiments tetrafluorinated olefins having F on an unsaturated, non-terminal carbon, such as 2,3,3,3-tetrafluoropropene. The preferred processes of the present invention in accordance with one embodiment generally comprise: (a) reacting a compound of formula (I) X1X2 (I) with a compound of formula (II) CX1X2X3CX1═CX1X2 (II) to produce a reaction product comprising a compound of formula (III) CF3CHX1CH2X2 (III), and (b) exposing said compound of formula (III) to reaction conditions effective to convert said compound of formula (III) to a compound of formula (IV) CF3CZ═CH2 (IV) wherein X1, X2, and X3 are each independently selected from the group consisting of hydrogen, chlorine, bromine, fluorine and iodine, provided that X1 and X2 in formula (I) are not both hydrogen and Z is Cl, I, Br, or F.
摘要翻译：公开了用于合成氟化烯烃的方法，特别优选的实施方案中，在不饱和的非末端碳上具有F的四氟化烯烃如2,3,3,3-四氟丙烯。根据一个实施方案的本发明的优选方法通常包括：（a）使式（I）X1X2（I）化合物与式（II）化合物CX1X2X3CX1 = CX1X2（II）反应以产生反应产物，其包含式（III）化合物，CF 3 CHX 1 CH 2 X 2（III）的化合物，和（b）将式（III）化合物暴露于有效将式（III）化合物转化成式（IV）化合物的反应条件：CF 3 CZ = CH 2 ）其中X1，X2和X3各自独立地选自氢，氯，溴，氟和碘，条件是式（I）中的X1和X2不同时为氢，Z为Cl，I，Br，或F.

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