公开(公告)号：WO2013049744A3

公开(公告)日：2013-07-04

申请号：PCT/US2012058152

申请日：2012-09-29

Applicant: HONEYWELL INT INC ,  WANG HAIYOU ,  BEKTESEVIC SELMA ,  TUNG HSUEH SUNG

Inventor： WANG HAIYOU ,  BEKTESEVIC SELMA ,  TUNG HSUEH SUNG

IPC: C07C17/25 ,  C07C17/42 ,  C07C21/185

CPC classification number: C07C17/20 ,  C07C17/206 ,  C07C17/389 ,  C07C21/04 ,  C07C21/18

Abstract: The present invention relates, in part, to the discovery that the presence of moisture in 1,1,2,3-tetrachloropropene (HCO-1230xa) results in catalyst deactivation and accelerated corrosion in the reactor during the fluorination of HCO-1230xa to 2-chloro-3,3,3-trifluoropropene. By substantially removing the moisture, it is shown that the catalyst life is extended and results in improved operation efficiency of the fluorination reaction. Such steps similarly result in an overall improvement in the production of certain hydrofluoroolefins, particularly 2,3,3,3-tetrafluoropropene (HFO-1234yf).

Abstract translation: 本发明部分涉及以下发现：在HCO-1230xa氟化为2时，在1,1,2,3-四氯丙烯（HCO-1230xa）中存在水分导致反应器中的催化剂失活和加速腐蚀 氯3,3,3-三氟丙烯。 通过基本上去除水分，显示催化剂寿命延长并且导致改善氟化反应的操作效率。 这些步骤类似地导致某些氢氟烯烃，特别是2,3,3,3-四氟丙烯（HFO-1234yf）的生产的总体改进。

公开(公告)号：WO2012166836A2

公开(公告)日：2012-12-06

申请号：PCT/US2012040070

申请日：2012-05-31

Applicant: HONEYWELL INT INC ,  CLOSE JOSHUA ,  WANG HAIYOU ,  TUNG HSUEH SUNG ,  COTTRELL STEPHEN A

Inventor： CLOSE JOSHUA ,  WANG HAIYOU ,  TUNG HSUEH SUNG ,  COTTRELL STEPHEN A

IPC: B01J23/745 ,  B01J19/08 ,  B01J19/20 ,  C07C21/06

CPC classification number: B01J8/10 ,  B01J8/005 ,  B01J8/0075 ,  B01J23/745 ,  B03C1/0335 ,  B03C5/00 ,  C07C17/275 ,  C07C17/278 ,  Y02P20/584 ,  C07C19/01

Abstract: Disclosed is a method for capturing and recycling iron catalyst used in the production of haloalkane compounds and more particularly, to an improved process for the manufacture of the compound 1,1,1,3,3-pentachloropropane (HCC-240fa), in which an electromagnetic separation unit (EMSU) is used to facilitate the reaction. When energized, the EMSU functions to remove the iron particles from the reactor effluent; when de-energized, the iron particles captured by the EMSU can be flushed back into the reactor for re-use in the continued production of HCC-240fa. The present invention is also useful in the manufacturing processes for other haloalkane compounds such as HCC-250 and HCC-360.

Abstract translation: 公开了一种用于捕获和再循环用于制备卤代烷烃化合物的铁催化剂的方法，更具体地说，涉及制备化合物1,1,1,3,3-五氯丙烷（HCC-240fa）的改进方法，其中 使用电磁分离单元（EMSU）来促进反应。 当通电时，EMSU用于从反应器流出物中除去铁颗粒; 当断电时，由EMSU捕获的铁颗粒可以冲洗回反应器，以便在继续生产HCC-240fa时重新使用。 本发明也可用于其它卤代烷烃化合物如HCC-250和HCC-360的制备方法。

公开(公告)号：WO2012094288A3

公开(公告)日：2012-08-30

申请号：PCT/US2012020035

申请日：2012-01-03

Applicant: HONEYWELL INT INC ,  POKROVSKI KONSTANTIN A ,  SINGH RAJIV RATNA ,  SHANKLAND IAN ,  TUNG HSUEH SUNG

Inventor： POKROVSKI KONSTANTIN A ,  SINGH RAJIV RATNA ,  SHANKLAND IAN ,  TUNG HSUEH SUNG

IPC: C07C17/20 ,  C07B39/00 ,  C07C19/10 ,  C07C21/18

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 -trifluoropropyne）。 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：WO2012099776A1

公开(公告)日：2012-07-26

申请号：PCT/US2012/021158

申请日：2012-01-13

Applicant: HONEYWELL INTERNATIONAL INC. ,  COTTRELL, Stephen A. ,  CHIU, Yuon ,  KOPKALLI, Haluk ,  TUNG, Hsueh Sung ,  UHRICH, Kevin D. ,  SCHEIDLE, Peter

Inventor： COTTRELL, Stephen A. ,  CHIU, Yuon ,  TUNG, Hsueh Sung ,  UHRICH, Kevin D. ,  SCHEIDLE, Peter

IPC: C07C17/25 ,  C07C21/18 ,  C07C17/38 ,  B01J23/18

CPC classification number: C07C17/21 ,  C07C17/087 ,  C07C17/206 ,  C07C17/25 ,  C07C17/38 ,  C07C17/383 ,  C07C19/10 ,  C07C21/18

Abstract: Disclosed is a process for the manufacture of 1234yf from 1,1,2,3-tetrachloro-propene, abbreviated herein as "TCP," in three integrated steps: (a) the R-1 hydrofluorination of TCP to form 1233xf in the vapor phase; (b) the R-2 hydrofluorination of 1233xf to form 244bb in either the liquid phase or in the liquid phase followed by the vapor phase; and (c) the R-3 dehydrochlorination of the 244bb in either the liquid or the vapor phase to produce 1234yf; wherein the vapor phase hydrofluorination of TCP in step (a) is carried out at a lower pressure than the liquid phase hydrofluorination of 123xf; and wherein the HCl generated during these steps is scrubbed with water to form an acid solution and the organic components are scrubbed with a caustic solution and then dried before further processing.

Abstract translation: 本发明公开了一种从1,1,2,3-四氯丙烯（本文缩写为“TCP”）制备1234yf的方法，三个一体化步骤：（a）TCP的R-1氢氟化在蒸气中形成1233xf 相; （b）1233xf的R-2氢氟化在液相或液相中形成244bb，随后是气相; 和（c）244bb在液相或气相中的R-3脱氯化氢以产生1234yf; 其中步骤（a）中TCP的气相氢氟化在比123xf的液相氢氟化更低的压力下进行; 并且其中在这些步骤期间产生的HCl用水洗涤以形成酸溶液，并且用苛性碱溶液洗涤有机组分，然后在进一步加工之前干燥。

公开(公告)号：WO2012094477A2

公开(公告)日：2012-07-12

申请号：PCT/US2012/020302

申请日：2012-01-05

Applicant: HONEYWELL INTERNATIONAL INC. ,  MERKEL, Daniel C. ,  TUNG, Hsueh Sung ,  POKROVSKI, Konstantin A. ,  WANG, Haiyou ,  BEKTESEVIC, Selma

Inventor： MERKEL, Daniel C. ,  TUNG, Hsueh Sung ,  POKROVSKI, Konstantin A. ,  WANG, Haiyou ,  BEKTESEVIC, Selma

IPC: C07C21/18 ,  C07C19/10 ,  B01J19/18

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：WO2011068649A3

公开(公告)日：2011-10-13

申请号：PCT/US2010056291

申请日：2010-11-11

Applicant: HONEYWELL INT INC ,  MERKEL DANIEL C ,  JOHNSON ROBERT C ,  TUNG HSUEH SUNG

Inventor： MERKEL DANIEL C ,  JOHNSON ROBERT C ,  TUNG HSUEH SUNG

IPC: C07C17/10 ,  B01J23/26 ,  B01J27/08 ,  C07C17/25 ,  C07C19/10

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的催化剂存在下氢氟化2-氯-3,3,3-三氟丙烯的步骤。

公开(公告)号：WO2011056441A3

公开(公告)日：2011-09-15

申请号：PCT/US2010053486

申请日：2010-10-21

Applicant: HONEYWELL INT INC ,  KOPKALLI HALUK ,  CHIU YUON ,  COTTRELL STEPHEN A ,  TUNG HSUEH SUNG ,  ULRICH KEVIN D

Inventor： KOPKALLI HALUK ,  CHIU YUON ,  COTTRELL STEPHEN A ,  TUNG HSUEH SUNG ,  ULRICH KEVIN D

IPC: C07C17/20 ,  C07C17/25 ,  C07C21/18 ,  C09K5/02

CPC classification number: C07C21/18 ,  C01B7/0718 ,  C01B7/0737 ,  C01B7/195 ,  C07C17/087 ,  C07C17/10 ,  C07C17/206 ,  C07C17/25 ,  Y02P20/125 ,  C07C19/10

Abstract: Disclosed is a process for the manufacture of HFO-1234yf from TCP in three integrated steps that include hydrofluorination of TCP (tetrachloropropene) to HCFC-1233xf in the vapor phase followed by hydrofluorination of HCFC-1233xf to HCFC-244bb in the liquid phase which is then followed by dehydrochlorination in liquid or vapor phase to produce HFO-1234yf. The vapor phase hydrofluorination is carried out at a higher pressure than the liquid phase hydrofluorination, thereby eliminating the need for compression and/or intermediate recovery. Also, any HCl generated from this reaction is fed to the liquid phase hydrofluorination section to promote agitation and mixing. This results in a more economical process from an initial capital and operating cost versus conducting the 3-steps sequentially.

Abstract translation: 公开了一种由TCP以三个整合步骤制造HFO-1234yf的方法，其包括在气相中将TCP（四氯丙烯）氢氟化为HCFC-1233xf，接着在液相中将HCFC-1233xf氢氟化为HCFC-244bb 然后在液相或汽相中进行脱氯化氢反应，生成HFO-1234yf。 气相氢氟化在比液相氢氟化更高的压力下进行，由此消除了压缩和/或中间回收的需要。 而且，由该反应产生的任何HCl被供给到液相氢氟化部分以促进搅拌和混合。 这从最初的资本和运营成本中获得了更经济的过程，而不是依次进行3个步骤。

公开(公告)号：WO2010088196A2

公开(公告)日：2010-08-05

申请号：PCT/US2010/022053

申请日：2010-01-26

Applicant: HONEYWELL INTERNATIONAL INC. ,  HULSE, Ryan ,  SINGH, Rajiv Ratna ,  TUNG, Hsueh Sung ,  SHANKLAND, Ian

Inventor： HULSE, Ryan ,  SINGH, Rajiv Ratna ,  TUNG, Hsueh Sung ,  SHANKLAND, Ian

IPC: C11D7/50 ,  C11D7/30 ,  C07C17/25 ,  C07C21/18 ,  C07C19/08 ,  C01B7/19

CPC classification number: C07C19/08 ,  C07C17/206 ,  C07C17/25 ,  C07C17/383 ,  C07C21/18

Abstract: The invention is directed to a ternary azeotrope-like mixture consisting essentially of effective amounts of 1,1,1,3,3-pentafluoropropane, 1-chloro-3,3,3-trifluoropropene, and hydrogen fluoride.

Abstract translation: 本发明涉及基本上由有效量的1,1,1,3,3-五氟丙烷，1-氯-3,3,3-三氟丙烯和氟化氢组成的三元共沸混合物。

公开(公告)号：WO2009155029A2

公开(公告)日：2009-12-23

申请号：PCT/US2009/045414

申请日：2009-05-28

Applicant: HONEYWELL INTERNATIONAL INC. ,  WANG, Haiyou ,  TUNG, Hsueh Sung

Inventor： WANG, Haiyou ,  TUNG, Hsueh Sung

IPC: C07C17/23 ,  C07C21/18 ,  B01J27/138 ,  B01J23/04

CPC classification number: B01J27/128 ,  B01J27/138 ,  B01J37/0009 ,  B01J37/0036 ,  B01J37/0236 ,  C07C17/25 ,  C07C21/18

Abstract: A process for making a fluorinated olefin. The process has the step of dehydrochlorinating a hydrochlorofluorocarbon having at least one hydrogen atom and at least one chlorine atom on adjacent carbon atoms in the presence of a catalytically effective amount of a catalyst composition. The catalyst composition is represented by the following: n wt.% MX/M'O y F z , wherein 0 + , Na + , K + , Rb + , and Cs + ; X is a halogen ion selected from the group consisting of F - , Cl - , Br - , and I - , M' is a bivalent metal ion; wherein n is a weight percentage of about 0.05% to about 50% MX based on the total weight of the MX and M'O y F z , and wherein y and z are the mole fractions of oxygen and fluorine in M'O y F z , respectively. There are also methods for making catalyst compositions.

Abstract translation: 一种制备氟化烯烃的方法。 该方法具有在催化有效量的催化剂组合物存在下，在相邻碳原子上具有至少一个氢原子和至少一个氯原子的氢氯氟烃脱氯化氢的步骤。 催化剂组合物由以下表示：n重量％MX / M'OyFz，其中0

公开(公告)号：WO2009064939A2

公开(公告)日：2009-05-22

申请号：PCT/US2008/083479

申请日：2008-11-14

Applicant: HONEYWELL INTERNATIONAL INC. ,  YANG, Shuwu ,  TUNG, Hsueh Sung

Inventor： YANG, Shuwu ,  TUNG, Hsueh Sung

IPC: C07C17/38 ,  C07C19/08 ,  B01J23/74 ,  B01J23/75 ,  B01J23/72

CPC classification number: C07C17/354 ,  B01J21/18 ,  B01J23/26 ,  B01J23/40 ,  B01J23/42 ,  B01J23/48 ,  B01J23/70 ,  B01J23/72 ,  B01J23/75 ,  B01J23/755 ,  C07C19/08

Abstract: A process for producing hydrofluorocarbon compounds represented by the following formula: CF 3 CHFCH m+ 1 F n wherein m is 0, 1, or 2; n is 0, 1, or 2; and m + n = 2. The process has the step of contacting, i.e., reacting, hydrogen with a precursor compound represented by the following formula: CF 3 CF=CH m F n wherein m is 0, 1, or 2; n is 0, 1, or 2; and m + n = 2. The contact is carried out in the presence of a solid catalyst and in the presence or absence of an inert gas. The catalyst is selected from the group consisting of: Fe, Co, Ni, Cu, Cr, Ru, Rh, Ag, Re, Os, Ir, Pt, Au, Sn, and any combinations thereof. For the hydrogenation of 1234yf to 254eb, Pd can also be used as catalyst in addition to the other above-referenced metals. These metals are preferably supported on a carrier such as activated carbon.

Abstract translation: 由下式表示的氢氟烃化合物的制造方法：CF 3 CHFCH m + 1 F n其中m为0,1或2; n为0,1或2; 并且m + n = 2。该方法具有使氢与由下式表示的前体化合物接触，即使其反应的步骤：CF 3 CF = CH m F n，其中m为0,1或2; n为0,1或2; 并且m + n = 2。该接触在固体催化剂存在下和在惰性气体存在或不存在下进行。 催化剂选自：Fe，Co，Ni，Cu，Cr，Ru，Rh，Ag，Re，Os，Ir，Pt，Au，Sn及其任何组合。 对于1234yf至254eb的氢化，除了其它上述金属之外，Pd也可用作催化剂。 这些金属优选负载在载体如活性炭上。