公开(公告)号：WO2015120234A1

公开(公告)日：2015-08-13

申请号：PCT/US2015/014759

申请日：2015-02-06

Applicant: MERKEL, Daniel C. ,  MAHLER, Barry ,  TUNG, Hsueh Sung ,  NAPPA, Mario Joseph

Inventor： MERKEL, Daniel C. ,  MAHLER, Barry ,  TUNG, Hsueh Sung ,  NAPPA, Mario Joseph

IPC: B01J8/38 ,  C07C17/20

CPC classification number: C07C17/087 ,  B01J19/18 ,  B01J19/1868 ,  C07C17/20 ,  C07C17/206 ,  C07C17/25 ,  C07C19/10

Abstract: The present invention relates to a hydrofluorinating process which comprises reacting a fluoroolefin with hydrogen fluoride in the liquid phase in the presence of a hydrofluorination catalyst in the reaction zone of a reactor, said reactor comprised of a reactor body having a length to diameter ratio of about 2:1 or greater; a stirred reaction zone containing said hydrofluorination catalyst, which may be prepared in situ, at least one inlet for supplying said hydrogen fluoride and fluoroolefin to the reaction zone and at least one outlet for recovering said fluoroalkane, said stirrer disposed in the reaction zone and comprising a plurality of blades fixedly attached to shaft drivable by a motor, said blades extending from about the bottom of the reaction zone to about the top of the reaction zone and said shaft extending on a longitudinal axis from the bottom of the reactor to the top of the reactor, said stirrer being rotated at a speed sufficient to promote a swirling of the liquid to effect the occurrence of hydrofluorination reaction and minimize overfluorination. The present invention also relates to said hyrdofluorination reactor.

Abstract translation: 本发明涉及一种氢氟化方法，其包括在反应器的反应区中在氟化氢催化剂存在下，在液相中使氟烯烃与氟化氢反应，所述反应器包括长径比为约 2：1或更大; 包含可以原位制备的所述氢氟化催化剂的搅拌反应区，至少一个用于将所述氟化氢和氟烯烃供应到反应区的入口和用于回收所述氟烷烃的至少一个出口，所述搅拌器设置在反应区中，并且包含 多个叶片固定地附接到由马达驱动的轴上，所述叶片从反应区域的底部延伸到反应区域的顶部，并且所述轴线在纵向轴线上从反应器底部延伸到顶部 反应器，所述搅拌器以足以促进液体旋转的速度旋转以实现氢氟化反应的发生并使过度氟化最小化。 本发明还涉及所述二氟化反应器。

公开(公告)号：WO2013067350A1

公开(公告)日：2013-05-10

申请号：PCT/US2012/063320

申请日：2012-11-02

Applicant: BEKTESEVIC, Selma ,  MERKEL, Daniel C. ,  NAPPA, Mario Joseph ,  SUN, Xuehui ,  TUNG, Hsueh Sung ,  WANG, Haiyou

Inventor： BEKTESEVIC, Selma ,  MERKEL, Daniel C. ,  NAPPA, Mario Joseph ,  SUN, Xuehui ,  TUNG, Hsueh Sung ,  WANG, Haiyou

IPC: C07C17/20 ,  C07C21/18 ,  B01J23/26

CPC classification number: B01J23/26 ,  B01J27/128 ,  B01J37/26 ,  C07C17/087 ,  C07C17/206 ,  C07C17/25 ,  C07C21/18 ,  C07C19/10

Abstract: The present invention relates, in part, to the discovery that, during the fluorination of certain fluoroolefin starting reagents, particularly, 1,1,2,3-tetrachloropropene (1230xa), oligomerization/polymerization of such starting reagents reduces the conversion process and leads to increased catalyst deactivation. The present invention also illustrates that providing one or more organic co-feed to the fluooolefin starting stream reduces such oligomerization/polymerization and improves catalystic stability.

Abstract translation: 本发明部分地涉及在某些氟烯烃起始试剂，特别是1,1,2,3-四氯丙烯（1230xa）的氟化期间，这种起始试剂的低聚/聚合降低了转化过程和引线 以增加催化剂失活。 本发明还说明，提供一种或多种有机共进料至氟烃起始物流中减少了这种低聚/聚合并改善了催化剂的稳定性。

公开(公告)号：WO2013055894A1

公开(公告)日：2013-04-18

申请号：PCT/US2012/059716

申请日：2012-10-11

Applicant: BEKTESEVIC, Selma ,  MERKEL, Daniel C. ,  NAPPA, Mario Joseph ,  SUN, Xuehui ,  TUNG, Hsueh Sung ,  WANG, Haiyou

Inventor： BEKTESEVIC, Selma ,  MERKEL, Daniel C. ,  NAPPA, Mario Joseph ,  SUN, Xuehui ,  TUNG, Hsueh Sung ,  WANG, Haiyou

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

CPC classification number: C07C17/20 ,  C07C17/087 ,  C07C17/25 ,  C07C21/04 ,  C07C21/18 ,  C07C19/10

Abstract: The present invention relates, in part, to the discovery that the presence of impurities in 1, 1, 2, 3-tetrachloropropene (1230xa) results in catalyst instability during the fluorination of 1230xa to 2-chloro-3, 3, 3-trifluoropropene. By substantially removing the impurities, 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 (1234yf).

Abstract translation: 本发明部分地涉及发现在1,1,2,3-四氯丙烯（1230xa）中杂质的存在导致1230xa氟化为2-氯-3,3,3-三氟丙烯（1230xa）期间的催化剂不稳定性 。 通过基本上除去杂质，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2,3,3,4-四氟丙烯（1234yf）的生产的总体改进。

公开(公告)号：WO2013055726A1

公开(公告)日：2013-04-18

申请号：PCT/US2012/059441

申请日：2012-10-10

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

Inventor： WANG, Haiyou ,  TUNG, Hsueh Sung

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

CPC classification number: C07C17/25 ,  B01J19/02 ,  B01J2219/0277 ,  C07C21/18

Abstract: The present invention relates, in part, to the discovery that the presence of impurities in a reactor for dehydrochlorinating HCFC-244bb to HFO-1234yf results in selectivity changeover from HFO-1234yf to HCFO-1233xf. By substantially removing such impurities, it is shown that the selectivity to HFO-1234yf via dehydrochlorination of HCFC-244bb is improved.

Abstract translation: 本发明部分地涉及这样的发现，即将HCFC-244bb脱氯化氢反应成HFO-1234yf的反应器中的杂质的存在导致从HFO-1234yf到HCFO-1233xf的选择性转换。 通过基本上除去这些杂质，显示通过HCFC-244bb的脱氯化氢对HFO-1234yf的选择性得到改善。

公开(公告)号：WO2013055722A1

公开(公告)日：2013-04-18

申请号：PCT/US2012/059437

申请日：2012-10-10

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

Inventor： WANG, Haiyou ,  TUNG, Hsueh Sung ,  MERKEL, Daniel C.

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

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

Abstract: The present invention relates, in part, to the discovery that the presence of impurities in a reactor for dehydrochlorinating HCFC-244bb to HFO-1234yf results in a reduced conversion rate and/or a selectivity changeover from HFO-1234yf to HCFO-1233xf. By substantially removing such impurities, it is shown that the conversion rate may be improved and selectivity to HFO-1234yf via dehydrochlorination of HCFC-244bb is also improved.

Abstract translation: 本发明部分地涉及以下发现，即将HCFC-244bb脱氯化氢反应到HFO-1234yf的反应器中的杂质的存在导致从HFO-1234yf到HCFO-1233xf的转化率和/或选择性转换的降低。 通过基本上除去这些杂质，可以看出可以提高转化率，并且通过HCFC-244bb的脱氯化氢还能改善对HFO-1234yf的选择性。

公开(公告)号：WO2012166836A3

公开(公告)日：2012-12-06

申请号：PCT/US2012/040070

申请日：2012-05-31

Applicant: HONEYWELL INTERNATIONAL 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 ,  C07C21/06 ,  B01J19/20 ,  B01J19/08

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.

公开(公告)号：WO2012154227A2

公开(公告)日：2012-11-15

申请号：PCT/US2012/021061

申请日：2012-01-12

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

Inventor： MERKEL, Daniel C. ,  WANG, Haiyou ,  POKROVSKI, Konstantin A. ,  TUNG, Hsueh Sung ,  SHANKLAND, Ian

IPC: C07C17/20 ,  C07C17/42 ,  C07C21/18 ,  B01J19/24

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 HC1); (2) the 244fa stream can then be used to directly produce any of the three desired products; (3 a) 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 (3 c) the 244fa stream can be further fluorinated to form 245 fa.

Abstract translation: 公开了共反应产生反式-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）在液相催化反应器中240fa与无水HF过量反应，主要共同生产1233zd（E）和244fa（加副产物HC1）; （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：WO2012145188A3

公开(公告)日：2012-10-26

申请号：PCT/US2012/032830

申请日：2012-04-10

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

Inventor： WANG, Haiyou ,  TUNG, Hsueh Sung

IPC: C07C17/23 ,  C07C21/18 ,  B01J23/26 ,  C07B63/00

Abstract: Trans-1233zd, the trans-isomer of 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) can be used as blowing agents, solvents, cleaning agents, as well as monomers of macromolecule compounds, and can be prepared through the dehydrochlorination of 1,1,1-trifluoro-3,3-dichloropropane (HCFC-243fa) with the help of a catalyst. The present invention is directed to an integrated process is proposed to produce trans-1233zd from 243fa, which is consisted of the following four major unit operations: (1) Catalytic dehydrochlorination of 243fa into trans/cis-1233zd, (2) HCl recovery, (3) Catalytic isomerization of cis-1233zd into trans-1233zzd, and (4) Isolation of trans-1233zd.

公开(公告)号：WO2012145188A2

公开(公告)日：2012-10-26

申请号：PCT/US2012032830

申请日：2012-04-10

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

Inventor： WANG HAIYOU ,  TUNG HSUEH SUNG

IPC: C07C17/23 ,  B01J23/26 ,  C07B63/00 ,  C07C21/18

CPC classification number: C07C17/25 ,  C07B2200/09 ,  C07C17/358 ,  C07C17/383 ,  Y02P20/125 ,  C07C21/18

Abstract: Trans-1233zd, the trans-isomer of 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) can be used as blowing agents, solvents, cleaning agents, as well as monomers of macromolecule compounds, and can be prepared through the dehydrochlorination of 1,1,1-trifluoro-3,3-dichloropropane (HCFC-243fa) with the help of a catalyst. The present invention is directed to an integrated process is proposed to produce trans-1233zd from 243fa, which is consisted of the following four major unit operations: (1) Catalytic dehydrochlorination of 243fa into trans/cis-1233zd, (2) HCl recovery, (3) Catalytic isomerization of cis-1233zd into trans-1233zzd, and (4) Isolation of trans-1233zd.

Abstract translation: 反式1233zd，1-氯-3,3,3-三氟丙烯（HCFO-1233zd）的反式异构体可用作发泡剂，溶剂，清洗剂以及大分子化合物的单体，并可通过 借助催化剂对1,1,1-三氟-3,3-二氯丙烷（HCFC-243fa）进行脱氯化氢。 本发明涉及从243fa生产反式1233zd的综合方法，其由以下四个主要单元操作组成：（1）将243fa催化脱氯化氢转化成反式/顺式1233zd，（2）HCl回收， （3）顺式1233zd催化异构化为反式-1233zzd，（4）反式-1233zd的分离。

公开(公告)号：WO2011149711A3

公开(公告)日：2012-03-01

申请号：PCT/US2011036789

申请日：2011-05-17

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

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

IPC: C09K5/04 ,  C07C21/18

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。