公开(公告)号：US09255046B2

公开(公告)日：2016-02-09

申请号：US12125045

申请日：2008-05-21

Applicant: Stephen A. Cottrell ,  Hsueh Sung Tung ,  Haiyou Wang ,  Yuon Chiu ,  Gustavo Cerri

Inventor： Stephen A. Cottrell ,  Hsueh Sung Tung ,  Haiyou Wang ,  Yuon Chiu ,  Gustavo Cerri

IPC: C07C17/00 ,  C07C19/08 ,  C07C21/18 ,  C07C23/00 ,  C07C25/13 ,  C07C17/25 ,  C07C17/358

CPC classification number: C07C17/25 ,  C07C17/358 ,  C07C21/18

Abstract: Disclosed is a method for forming HFO-1234ze, and for forming compositions comprising HFO-1234ze, by (a) converting, preferably by dehydrofluorination, pentafluorpropane (HFC-245), preferably 1,1,1,3,3-pentafluorpropane (HFC-245fa), preferably by contact with a caustic solution, to a reaction product comprising cis-HFO-1234ze and trans-HFO-1234ze; and (b) contacting at least a portion, preferably substantially portion, and in certain embodiments substantially all of said reaction product with at least one isomerization catalyst to convert at least a portion, and preferably at least a substantial portion, of cis-HFO-1234ze in said reaction product to trans-HFO-1234ze.

Abstract translation: 公开了形成HFO-1234ze的方法，以及用于形成包含HFO-1234ze的组合物的方法，通过（a）优选通过脱氟化氢转化五氟丙烷（HFC-245），优选1,1,1,3,3-五氟丙烷（HFC -245fa），优选通过与苛性碱溶液接触，加入到包含顺-HFO-1234ze和反-HFO-1234ze的反应产物中; 并且（b）使至少一部分，优选基本上部分，在某些实施方案中使基本上所有的所述反应产物与至少一种异构化催化剂接触，以将至少一部分，优选至少大部分的顺-HFO- 1234ze在所述反应产物中以反式HFO-1234ze。

公开(公告)号：US09156752B2

公开(公告)日：2015-10-13

申请号：US12984024

申请日：2011-01-04

Applicant: Konstantin A. Pokrovski ,  Rajiv Ratna Singh ,  Ian Shankland ,  Hsueh Sung Tung

Inventor： Konstantin A. Pokrovski ,  Rajiv Ratna Singh ,  Ian Shankland ,  Hsueh Sung Tung

IPC: C07C21/18 ,  C07C17/20 ,  C07C17/25

CPC classification number: C07C17/361 ,  C07B2200/09 ,  C07C17/206 ,  C07C17/25 ,  C07C19/10 ,  C07C21/18

Abstract: The present invention discloses high purity E-1-chloro-3,3,3-trifluoropropene (1233zd(E)) and methods to produce the same. More specifically, the present invention discloses the methods of making 1233zd(E) essentially free of toxic impurities (e.g. 2-chloro-3,3,3-trifluoropropene (1233xf), chlorotetrafluoro-propene (1224), and 3,3,3-trifluoropropyne). The present invention further provides methods for making high purity 1233zd(E) with concentration of 1233xf and 1224 at or below 200 parts per million (ppm) and 3,3,3-trifluoropropyne impurities at or below 20 ppm. Formation of 1233xf impurity can be avoided if pure 1,1,1,3,3-pentachloropropane is used as a starting material. It was also found that formation of 1233xf is avoided if a liquid phase manufacturing process is used.

Abstract translation: 本发明公开了高纯度E-1-氯-3,3,3-三氟丙烯（1233zd（E））及其制备方法。 更具体地说，本发明公开了制备基本上不含有毒杂质的1233zd（E）的方法（例如2-氯-3,3,3-三氟丙烯（1233xf），氯四氟丙烯（1224）和3,3,3 三氟丙炔）。 本发明还提供了制备浓度为1233xf和1224等于或低于200ppm（ppm）的高纯度1233zd（E）和等于或低于20ppm的3,3,3-三氟丙炔杂质的方法。 如果使用纯1,1,1,3,3-五氯丙烷作为原料，则可以避免形成1233xf杂质。 还发现如果使用液相制造方法，则避免形成1233xf。

公开(公告)号：US09024092B2

公开(公告)日：2015-05-05

申请号：US12631728

申请日：2009-12-04

Applicant: Daniel C. Merkel ,  Robert C. Johnson ,  Hsueh Sung Tung

Inventor： Daniel C. Merkel ,  Robert C. Johnson ,  Hsueh Sung Tung

IPC: C07C17/00 ,  C07C19/08 ,  C07C21/18 ,  C07C23/00 ,  C07C25/13 ,  C07C19/10 ,  C07C17/087

CPC classification number: C07C17/013 ,  C07C17/087 ,  C07C19/10

Abstract: Provided is a process for making 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of hydrofluorinating 2-chloro-3,3,3-trifluoropropene in the presence of a catalyst selected from the group consisting of SbCl3, SbCl5, SbF5, TiCl4, SnCl4, Cr2O3, and fluorinated Cr2O3.

Abstract translation: 提供了制备2-氯-1,1,1,2-四氟丙烷的方法。 该方法具有在选自SbCl 3，SbCl 5，SbF 5，TiCl 4，SnCl 4，Cr 2 O 3和氟化Cr 2 O 3的催化剂存在下氢化2-氯-3,3,3-三氟丙烯的步骤。

公开(公告)号：US08916733B2

公开(公告)日：2014-12-23

申请号：US12484588

申请日：2009-06-15

Applicant: Daniel C. Merkel ,  Robert C. Johnson ,  Hsueh Sung Tung

Inventor： Daniel C. Merkel ,  Robert C. Johnson ,  Hsueh Sung Tung

IPC: C07C19/08 ,  C07C17/00 ,  C07C17/08 ,  C07C17/087

CPC classification number: C07C17/087 ,  C07C19/10

Abstract: A process for making 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of contacting 2-chloro-3,3,3-trifluoropropene with hydrogen fluoride in the presence of a catalyst having about 25 to about 99.9 mole percent antimony pentachloride and about 0.1 to about 75 mole percent of a metal of a Lewis acid under conditions sufficient to form the 2-chloro-1,1,1,2-tetrafluoropropane. There is a second process for making 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of hydrofluorinating about 75 to about 99.9 mole percent 2-chloro-3,3,3-trifluoropropene and about 0.1 to about 25 mole percent of one or more other hydrocarbons having at least one chlorine atom in the presence of a catalyst of fluorinated antimony pentachloride under conditions sufficient to form the 2-chloro-1,1,1,2-tetrafluoropropane. There is yet another process for hydrofluorinating 2-chloro-3,3,3-trifluoropropene to 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of contacting the 2-chloro-3,3,3-trifluoropropene with hydrogen fluoride in the presence of a vapor phase catalyst under conditions sufficient to form the 2-chloro-1,1,1,2-tetrafluoropropane.

Abstract translation: 制备2-氯-1,1,1,2-四氟丙烷的方法。 该方法具有在催化剂存在下使2-氯-3,3,3-三氟丙烯与氟化氢接触的步骤，该催化剂具有约25至约99.9摩尔％的五氯化锑和约0.1至约75摩尔％的金属 路易斯酸在足以形成2-氯-1,1,1,2-四氟丙烷的条件下进行。 制备2-氯-1,1,1,2-四氟丙烷的第二种方法。 该方法具有在存在下存在下，将约75-约99.9摩尔％的2-氯-3,3,3-三氟丙烯和约0.1-约25摩尔％的一种或多种其它具有至少一个氯原子的烃氢氟化的步骤 在足以形成2-氯-1,1,1,2-四氟丙烷的条件下的氟化五氯化锑催化剂。 还有将2-氯-3,3,3-三氟丙烯氢氟化为2-氯-1,1,1,2-四氟丙烷的另一种方法。 该方法具有在气相催化剂存在下，在足以形成2-氯-1,1,1,2-四氟丙烷的条件下使2-氯-3,3,3-三氟丙烯与氟化氢接触的步骤。

公开(公告)号：US08766020B2

公开(公告)日：2014-07-01

申请号：US12510740

申请日：2009-07-28

Applicant: Haiyou Wang ,  Hsueh Sung Tung ,  Rajiv R. Singh ,  Ian Shankland

Inventor： Haiyou Wang ,  Hsueh Sung Tung ,  Rajiv R. Singh ,  Ian Shankland

IPC: C07C17/25 ,  C07C19/08 ,  C07C21/18 ,  C07C21/00 ,  C07C17/00

CPC classification number: C07C19/08 ,  C07C17/04 ,  C07C17/25 ,  C07C17/383 ,  C07C17/395 ,  C07C21/18 ,  C07C19/10

Abstract: The present invention discloses a manufacturing process to produce high purity 1234yf from 245eb, which preferably includes the removal of impurities present in 245eb raw material, the dehydrofluorination of 245eb, and the removal of impurities present in final crude product. The disclosed manufacturing process allows the production of a 1234yf product with lower the levels of 1225ye and/or trifluoropropene, preferably in amounts of less than about 500, and 50 ppm, respectively.

Abstract translation: 本发明公开了一种从245eb生产高纯度1234yf的制造方法，其优选包括去除245eb原料中存在的杂质，245eb的脱氟化氢和去除最终粗产物中存在的杂质。 所公开的制造方法允许生产具有较低1225ye和/或三氟丙烯含量的1234yf产品，优选分别小于约500ppm和50ppm。

公开(公告)号：US08722945B2

公开(公告)日：2014-05-13

申请号：US12264635

申请日：2008-11-04

Applicant: Shuwu Yang ,  Hsueh Sung Tung

Inventor： Shuwu Yang ,  Hsueh Sung Tung

IPC: C07C261/00

CPC classification number: C07C17/093 ,  B01J21/18 ,  B01J23/04 ,  B01J23/10 ,  B01J23/63 ,  B01J23/92 ,  B01J23/96 ,  B01J27/1806 ,  B01J27/285 ,  B01J38/14 ,  C07C17/10 ,  C07C17/202 ,  C07C17/204 ,  C07C17/206 ,  Y02P20/584 ,  C07C19/16

Abstract: A process for the preparation of a fluoroiodoalkane represented by the structural formula CF3(CF2)n—I, wherein n is 0 or 1. The process has the step of reacting a source of iodine with a compound represented by the structural formula CF3(CF2)n—Y, wherein Y is selected from H, Cl, Br and COOH and wherein n is 0 or 1. The reaction is carried out at a temperature from about 100° C. to about 750° C. and at a pressure from about 0.001 to about 100 atm for a contact time from about 0.001 second to about 300 hours in the presence a catalyst. The catalyst is subject to one or both of the following: (a) treating the catalyst prior to the reaction via contact with a gas selected from the group consisting of hydrogen fluoride, trifluoromethane, hydrogen, hydrogen iodide, iodine, fluorine, and oxygen, wherein the contact is carried out at a temperature and for a contact time sufficient to reduce the length of the induction period of the catalyst; and (b) treating the catalyst after the reaction via contact with a gas selected from the group consisting of hydrogen fluoride, hydrogen, fluorine, oxygen, or air at a temperature and for a contact time sufficient to regenerate the catalyst.

Abstract translation: 制备由结构式CF 3（CF 2）n-1表示的氟代碘代烷烃的方法，其中n为0或1.该方法具有使碘源与由结构式CF 3（CF 2） ）n-Y，其中Y选自H，Cl，Br和COOH，并且其中n为0或1.反应在约100℃至约750℃的温度下进行， 在约0.001至约100大气压下，在催化剂存在下，接触时间为约0.001秒至约300小时。 催化剂经受以下一个或两个：（a）在反应之前通过与选自氟化氢，三氟甲烷，氢，碘化氢，碘，氟和氧的气体接触来处理催化剂， 其中所述接触在足以减少所述催化剂的诱导期的长度的温度和接触时间下进行; 和（b）在反应后通过与选自氟化氢，氢，氟，氧或空气的气体在足以再生催化剂的温度和接触时间下处理催化剂。

公开(公告)号：US08648222B2

公开(公告)日：2014-02-11

申请号：US13176856

申请日：2011-07-06

Applicant: Haiyou Wang ,  Hsueh Sung Tung

Inventor： Haiyou Wang ,  Hsueh Sung Tung

IPC: C07C17/00

CPC classification number: B01J27/138 ,  B01J27/08 ,  B01J27/128 ,  B01J35/0006 ,  B01J37/0236 ,  B01J37/04 ,  C07C17/25 ,  C07C21/18

Abstract: There is provided methods for making a catalyst composition represented by the formula MX/M′F2 wherein MX is an alkali metal halide; M is an alkali metal ion selected from the group consisting of Li+, Na+, K+, Rb+, and Cs+; X is a halogen ion selected from the group consisting of F−, Cl−, Br−, and I−; M′F2 is a bivalent metal fluoride; and M′ is a bivalent metal ion. There is also a method for making a fluorinated olefin.

Abstract translation: 提供制备由式MX / M'F2表示的催化剂组合物的方法，其中MX是碱金属卤化物; M是选自Li +，Na +，K +，Rb +和Cs +的碱金属离子; X是选自F-，Cl-，Br-和I-的卤素离子; M'F2是二价金属氟化物; M'是二价金属离子。 还有一种制备氟化烯烃的方法。

公开(公告)号：US08575407B2

公开(公告)日：2013-11-05

申请号：US13424748

申请日：2012-03-20

Applicant: Haiyou Wang ,  Hsueh Sung Tung

Inventor： Haiyou Wang ,  Hsueh Sung Tung

IPC: C07C19/08 ,  C07C21/18 ,  C07C23/00 ,  C07C25/13 ,  C07C17/08 ,  B01J27/06 ,  B01J23/40 ,  B01J23/42 ,  B01J23/58 ,  B01J23/72 ,  B01J23/00 ,  B01J23/70 ,  B01J23/74 ,  B01J23/44

CPC classification number: B01J37/18 ,  B01J21/04 ,  B01J21/10 ,  B01J23/44 ,  B01J27/13 ,  B01J37/035 ,  B01J37/038 ,  C07C17/354 ,  C07C19/08

Abstract: A support of metal oxyfluoride or metal halide for a metal-based hydrogenation catalyst useful in hydrogenating fluoroolefins is provided.

Abstract translation: 提供了用于氢化氟烯烃的金属基氢化催化剂的金属氟氧化物或金属卤化物的载体。

公开(公告)号：US08436218B2

公开(公告)日：2013-05-07

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: C07C17/02 ,  C07C17/04

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：US08436217B2

公开(公告)日：2013-05-07

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: C07C17/25 ,  C07C19/08 ,  C07C21/18 ,  C07C23/00 ,  C07C25/00 ,  C07C17/00

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。