公开(公告)号：US20120271070A1

公开(公告)日：2012-10-25

申请号：US13093007

申请日：2011-04-25

Applicant: Haiyou Wang ,  Daniel C. Merkel ,  Konstantin A. Pokrovski ,  Hsueh Sung Tung ,  Ian Shankland

Inventor： Haiyou Wang ,  Daniel C. Merkel ,  Konstantin A. Pokrovski ,  Hsueh Sung Tung ,  Ian Shankland

IPC: C07C17/38 ,  C07C17/25

CPC classification number: C07C17/206 ,  C07B2200/09 ,  C07C17/087 ,  C07C17/25 ,  C07C17/383 ,  Y02P20/125 ,  C07C19/10 ,  C07C19/08 ,  C07C21/18

Abstract: Disclosed is a fully integrated process for making 1,1,1,3,3-pentafluoropropane (HFC-245fa), trans-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)), and trans-1,3,3,3-tetrafluoropropene (HFO-1234ze(E)). The chemistry involves (a) the reaction of 1,1,1,3,3-pentachloropropane (HCC-240fa), or a derivative thereof selected from 1,1,3,3-tetrachloropropene and 1,3,3,3-tetrachloropropene, with anhydrous HF in excess in the presence of a catalyst in a liquid-phase reactor in such a way as to co-produce HCFO-1233zd, HFO-1234ze, HCFC-244fa (3-chloro-1,1,1,3-tetrafluoropropane), and HFC-245fa in a first reactor; (b) the reaction of HCFO-1233zd and HFO-1234ze with HCl in excess in the presence of a catalyst in a second reactor to convert these two olefins into HCFC-243fa and HCFC-244fa, respectively; (c) the reaction of HCFC-243fa and HCFC-244fa over a dehydrochlorination catalyst or in a caustic solution in a third reactor to form HCFO-1233zd and HFO-1234ze; and (d) the reaction of HCFO-1233zd(Z) and HFO-1234ze(Z) in the presence of a catalyst in a fourth reactor to form trans-1233zd and trans-1234ze, respectively.

Abstract translation: 公开了制备1,1,1,3,3-五氟丙烷（HFC-245fa），反式-1-氯-3,3,3-三氟丙烯（HCFO-1233zd（E））的完全一体化方法， 1,3,3,3-四氟丙烯（HFO-1234ze（E））。 该化学方法包括（a）1,1,1,3,3-五氯丙烷（HCC-240fa）或其衍生物选自1,1,3,3-四氯丙烯和1,3,3,3-四氯丙烯的反应， 四氯丙烯，在催化剂存在下，在液相反应器中以无水HF过剩，以共同生产HCFO-1233zd，HFO-1234ze，HCFC-244fa（3-氯-1,1,1， 3-四氟丙烷）和HFC-245fa在第一反应器中; （b）HCFO-1233zd和HFO-1234ze与HCl在过渡催化剂存在下在第二反应器中的反应，分别将这两种烯烃转化为HCFC-243fa和HCFC-244fa; （c）HCFC-243fa和HCFC-244fa在脱氯化氢催化剂或第三反应器中的苛性碱溶液中的反应，形成HCFO-1233zd和HFO-1234ze; 和（d）HCFO-1233zd（Z）和HFO-1234ze（Z）在催化剂存在下在第四反应器中的反应分别形成反式-1233zd和反式1234ze。

公开(公告)号：US08263818B2

公开(公告)日：2012-09-11

申请号：US12686857

申请日：2010-01-13

Applicant: Haiyou Wang ,  Konstantin A. Pokrovski ,  Hsueh S. Tung ,  Michael Van Der Puy

Inventor： Haiyou Wang ,  Konstantin A. Pokrovski ,  Hsueh S. Tung ,  Michael Van Der Puy

IPC: C07C17/00

Abstract: The present invention involves methods for isomerization of 1234zc. Also provided are methods for managing 1,1,3,3-tetrafluoropropene produced as a byproduct in a process for synthesizing trans-1,3,3,3-tetrafluoropropene from 245fa, wherein 1234zc is converted into trans/cis-1234ze with the help of a catalyst in the absence of HF and in an isomerization reactor, or is converted into 1234zc and/or 245fa with the help of a catalyst in the presence of HF in a separate reactor or preferably in the same reactor of 245fa dehydrofluorination.

公开(公告)号：US08252965B2

公开(公告)日：2012-08-28

申请号：US12540252

申请日：2009-08-12

Applicant: Daniel C. Merkel ,  Hsueh Sung Tung ,  Konstantin A. Pokrovski

Inventor： Daniel C. Merkel ,  Hsueh Sung Tung ,  Konstantin A. Pokrovski

IPC: C07C21/00

CPC classification number: C07C17/392 ,  C07C17/087 ,  C07C17/25 ,  C07C17/38 ,  C07C21/18 ,  C07C19/10

Abstract: The invention provides a method for separating halocarbons. In particular, a method for separating 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) from 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) based on differences in melting points of these compounds. More particularly the invention pertains to a method for separating HCFC-244bb from HCFO-1233xf which are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).

Abstract translation: 本发明提供一种分离卤代烃的方法。 特别地，基于这些的熔点的差异，从2-氯-3,3,3-三氟丙烯（HCFO-1233xf）中分离出2-氯-1,1,1,2-四氟丙烷（HCFC-244bb）的方法 化合物。 更具体地说，本发明涉及从HCFO-1233xf中分离HCFC-244bb的方法，其可用作生产2,3,3,3-四氟丙烯（HFO-1234yf）中的中间体。

公开(公告)号：US20120184786A1

公开(公告)日：2012-07-19

申请号：US13315341

申请日：2011-12-09

Applicant: Daniel C. Merkel ,  Haiyou Wang ,  Konstantin A. Pokrovski ,  Hsueh Sung Tung ,  Ian Shankland

Inventor： Daniel C. Merkel ,  Haiyou Wang ,  Konstantin A. Pokrovski ,  Hsueh Sung Tung ,  Ian Shankland

IPC: C07C17/23

CPC classification number: C07C17/25 ,  C07C17/087 ,  C07C17/206 ,  Y02P20/125 ,  Y02P20/582 ,  C07C21/18 ,  C07C19/10 ,  C07C19/08

Abstract: Disclosed is an integrated process to co-produce trans-1-chloro-3,3,3-trifluoro-propene (1233zd(E)), trans-1,3,3,3-tetrafluoropropene (1234ze(E)), and 1,1,1,3,3-pentafluoropropane (245fa). Overall the co-production is a three-step process. The chemistry involves the steps of: (1) the reaction of 240fa with anhydrous HF in excess in a liquid-phase catalyzed reactor in such a way as to co-produce primarily 1233zd(E) and 244fa (plus byproduct HCl); (2) the 244fa stream can then be used to directly produce any of the three desired products; (3a) the 244fa stream can be dehydrochlorinated to produce the desired second product 1234ze(E); and/or (3b) the 244fa stream can be dehydrofluorinated to produce 1233zd(E) if more of that product is desired; and/or (3c) the 244fa stream can be further fluorinated to form 245fa.

Abstract translation: 公开了共同生产反式-1-氯-3,3,3-三氟丙烯（1233zd（E）），反式-1,3,3,3-四氟丙烯（1234ze（E））和 1,1,1,3,3-五氟丙烷（245fa）。 总的来说，联合制作是一个三步骤的过程。 该化学方法包括以下步骤：（1）在液相催化的反应器中240fa与无水HF的过量反应，以共同主要生成1233zd（E）和244fa（加副产物HCl）; （2）然后可以使用244fa流直接生产三种所需产物中的任何一种; （3a）244fa流可以脱氯化氢以产生所需的第二产物1234ze（E）; 和/或（3b）如果需要更多的该产物，则244fa流可以被脱氟化氢以产生1233zd（E） 和/或（3c）244fa流可以进一步氟化以形成245fa。

公开(公告)号：US20120178977A1

公开(公告)日：2012-07-12

申请号：US13313085

申请日：2011-12-07

Applicant: Daniel C. Merkel ,  Hsueh Sung Tung ,  Konstantin A. Pokrovski ,  Haiyou Wang ,  Selma Bektesevic

Inventor： Daniel C. Merkel ,  Hsueh Sung Tung ,  Konstantin A. Pokrovski ,  Haiyou Wang ,  Selma Bektesevic

IPC: C07C21/18 ,  B01J19/00

CPC classification number: B01D3/009 ,  C07C17/206 ,  C07C17/25 ,  C07C17/383 ,  Y02P20/582 ,  C07C21/18

Abstract: Disclosed is a method for the production of 1233xf comprising the continuous low temperature liquid phase reaction of 1,1,1,2,3-pentachloropropane and anhydrous HF, without the use of a catalyst, wherein the reaction takes place in one or more reaction vessels, each one in succession converting a portion of the original reactants fed to the lead reaction vessel and wherein the reactions are run in a continuous fashion.

Abstract translation: 公开了一种制备1233xf的方法，其包括1,1,1,2,3-五氯丙烷和无水HF的连续低温液相反应，不使用催化剂，其中反应在一个或多个反应 容器，每个连续地将一部分原始反应物转化成铅反应容器，其中反应以连续的方式运行。

公开(公告)号：US08217208B2

公开(公告)日：2012-07-10

申请号：US12633420

申请日：2009-12-08

Applicant: Ryan Hulse ,  Rajiv R. Singh ,  Konstantin A. Pokrovski ,  Hsueh Sung Tung ,  Daniel Merkel ,  Haiyou Wang ,  Michael Van Der Puy

Inventor： Ryan Hulse ,  Rajiv R. Singh ,  Konstantin A. Pokrovski ,  Hsueh Sung Tung ,  Daniel Merkel ,  Haiyou Wang ,  Michael Van Der Puy

IPC: C07C17/00

CPC classification number: C07C17/358 ,  C07C17/383 ,  C07C21/18

Abstract: Disclosed are processes for an isomerization reaction between (E)1-chloro-3,3,3-trifluoropropene and (Z)1-chloro-3,3,3-trifluoropropene. Some of the disclosed processes include the step of contacting a feed stream with a heated surface, where the feed stream includes (E)1-chloro-3,3,3-trifluoropropene, (Z)1-chloro-3,3,3-trifluoropropene or mixtures thereof. The resulting product stream includes (E)1-chloro-3,3,3-trifluoropropene and (Z)1-chloro-3,3,3-trifluoropropene, where the ratio of (E) isomer to (Z) isomer in the product stream is different than the ratio feed stream. The (E) and (Z) isomers in the product stream may be separated from one another.

Abstract translation: 公开了（E）1-氯-3,3,3-三氟丙烯和（Z）1-氯-3,3,3-三氟丙烯之间异构化反应的方法。 一些所公开的方法包括使进料流与加热表面接触的步骤，其中进料流包含（E）1-氯-3,3,3-三氟丙烯，（Z）1-氯-3,3,3 - 三氟丙烯或其混合物。 所得产物流包含（E）1-氯-3,3,3-三氟丙烯和（Z）1-氯-3,3,3-三氟丙烯，其中（E）异构体与（Z）异构体的比例 产品流与进料流比不同。 产物流中的（E）和（Z）异构体可以彼此分离。

公开(公告)号：US08168837B2

公开(公告)日：2012-05-01

申请号：US12464666

申请日：2009-05-12

Applicant: Daniel C. Merkel ,  Konstantin A. Pokrovski ,  Hsueh Sung Tung

Inventor： Daniel C. Merkel ,  Konstantin A. Pokrovski ,  Hsueh Sung Tung

IPC: C07C17/38 ,  C09K5/00 ,  B01D3/34

CPC classification number: C07C17/383 ,  C07C17/087 ,  C07C17/25 ,  C07C19/10 ,  C07C21/18

Abstract: Provided is a process for purifying an organic feedstock comprising (a) distilling a raw organic feedstock comprising hydrogen fluoride, 2-chloro-1,1,1,2-tetrafluoropropane, and 2-chloro-3,3,3-trifluoropropene to produce a first distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a first bottoms stream rich in hydrogen fluoride; (b) cooling said first distillate stream to produce an intermediate composition comprising an organic layer rich in 2-chloro-1,1,1,2-tetrafluoropropane and 2-chloro-3,3,3-trifluoropropene, and an acid layer rich in hydrogen fluoride; and, optionally but preferably, (c) distilling said organic layer to produce a second distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a second bottoms stream comprising a purified organic feedstock substantially free of hydrogen fluoride.

Abstract translation: 提供了一种纯化有机原料的方法，其包括（a）蒸馏包含氟化氢，2-氯-1,1,1,2-四氟丙烷和2-氯-3,3,3-三氟丙烯的原始有机原料以产生 包含2-氯-1,1,1,2-四氟丙烷，2-氯-3,3,3-三氟丙烯和氟化氢的类共沸组合物的第一蒸馏物流和富含氟化氢的第一塔底物流 ; （b）冷却所述第一馏出物流以产生包含富含2-氯-1,1,1,2-四氟丙烷和2-氯-3,3,3-三氟丙烯的有机层和富含酸层的中间组合物 在氟化氢中; 和（c）蒸馏所述有机层以产生包含2-氯-1,1,1,2-四氟丙烷的共沸混合物组合物，2-氯-3,3,3-四氯丙烷的第二馏出物流， 三氟丙烯和氟化氢，以及包含基本上不含氟化氢的纯化有机原料的第二塔底物流。

公开(公告)号：US20120059201A1

公开(公告)日：2012-03-08

申请号：US12875170

申请日：2010-09-03

Applicant: Daniel C. Merkel ,  Konstantin A. Pokrovski ,  Hsueh Sung Tung

Inventor： Daniel C. Merkel ,  Konstantin A. Pokrovski ,  Hsueh Sung Tung

IPC: C07C17/25

CPC classification number: C07C17/25 ,  C07C17/206 ,  C07C17/354 ,  C07C21/18 ,  C07C19/08

Abstract: Disclosed is a process for the preparation of 3,3,3-trifluoropropene comprising the steps of; (1) fluorination of 240fa to form 245fa; (2) conversion of 245fa to a cis/trans mixture of 1234ze; (3) hydrogenation of the cis/trans mixture of 1234ze to form 254fb; and (4) dehydrofluorination of 254fb to produce 3,3,3-trifluoropropene. Alternatively or additionally, a second process for the preparation of the desired compound comprises the following steps; (1) fluorination of HCC-240fa to form HCFC-244fa; (2) conversion of 244fa to a cis/trans mixture of HFO-1234ze; (3) hydrogenation of the cis/trans mixture of 1234ze to form HFC-254fb; and (4) dehydrofluorination of 254fb to produce 3,3,3-trifluoropropene.

Abstract translation: 公开了制备3,3,3-三氟丙烯的方法，包括以下步骤： （1）240fa的氟化以形成245fa; （2）将245fa转化为1234ze的顺式/反式混合物; （3）将1234ze的顺式/反式混合物氢化成254fb; 和（4）254fb的脱氟化氢，得到3,3,3-三氟丙烯。 或者或另外，制备所需化合物的第二种方法包括以下步骤： （1）HCC-240fa氟化形成HCFC-244fa; （2）将244fa转化为HFO-1234ze的顺式/反式混合物; （3）将1234ze的顺式/反式混合物氢化形成HFC-254fb; 和（4）254fb的脱氟化氢，得到3,3,3-三氟丙烯。

公开(公告)号：US20110295045A1

公开(公告)日：2011-12-01

申请号：US12788885

申请日：2010-05-27

Applicant: RYAN HULSE ,  HANG T. PHAM ,  RAJIV RATNA SINGH ,  HSUEH SUNG TUNG ,  DANIEL C. MERKEL ,  KONSTANTIN A. POKROVSKI

Inventor： RYAN HULSE ,  HANG T. PHAM ,  RAJIV RATNA SINGH ,  HSUEH SUNG TUNG ,  DANIEL C. MERKEL ,  KONSTANTIN A. POKROVSKI

IPC: C07C17/383 ,  C09K13/08 ,  C23G1/02

CPC classification number: C07C17/38 ,  C01B7/198 ,  C07C17/383 ,  C07C17/386 ,  C07C17/389 ,  C07C19/08

Abstract: The present invention relates to an azeotropic or azeotrope-like mixture consisting essentially of 1,1,1,2,3,3-hexafluoropropane, hexafluoropropene and hydrogen fluoride.

Abstract translation: 本发明涉及基本上由1,1,1,2,3,3-六氟丙烷，六氟丙烯和氟化氢组成的共沸或类共沸混合物。

公开(公告)号：US20110210289A9

公开(公告)日：2011-09-01

申请号：US12406653

申请日：2009-03-18

Applicant: DANIEL C. MERKEL ,  Konstantin A. Pokrovski ,  Hsuehsung Tung ,  Hang T. Pham ,  Rajiv R. Singh

Inventor： DANIEL C. MERKEL ,  Konstantin A. Pokrovski ,  Hsuehsung Tung ,  Hang T. Pham ,  Rajiv R. Singh

IPC: C09K3/00 ,  B01D3/36

CPC classification number: C07C21/18 ,  C07C19/10

Abstract: Provided are ternary azeotropic and azeotrope-like compositions of 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb), and hydrogen fluoride (HF). Such azeotropic and azeotrope-like compositions are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).

Abstract translation: 提供了2-氯-3,3,3-三氟丙烯（HCFO-1233xf），2-氯-1,1,1,2-四氟丙烷（HCFC-244bb）和氟化氢（的三元共沸和类共沸组合物） HF）。 这种共沸和类共沸组合物可用作生产2,3,3,3-四氟丙烯（HFO-1234yf）的中间体。