公开(公告)号：US20140186230A1

公开(公告)日：2014-07-03

申请号：US14195893

申请日：2014-03-04

Applicant: Honeywell International Inc.

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

IPC: B01D3/00

CPC classification number: C07C17/20 ,  B01D3/009 ,  C01B7/0706 ,  C01B7/0712 ,  C07C17/206 ,  C07C17/25 ,  C07C17/358 ,  C07C17/383 ,  C07C21/18 ,  Y02P20/582

Abstract: Disclosed is process for the production of (E) 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)) by conducting a continuous reaction without the use of a catalyst. Also disclosed is an integrated system for producing hydrofluoro olefins, particularly 1233zd(E). The manufacturing process includes six major unit operations: (1) a fluorination reaction of HCC-240fa (in continuous or semi-batch mode) using HF with simultaneous removal of by-product HCl and the product 1233zd(E); (2) recycle of unreacted HCC-240fa and HF together with under-fluorinated by-products back to (1); (3) separation and purification of by-product HCl; (4) separation of excess HF back to (1); (5) purification of final product, 1233zd(E); and (6) isomerization of by-product 1233zd(Z) to 1233zd(E) to maximize the process yield.

Abstract translation: 公开了通过在不使用催化剂的情况下进行连续反应来制备（E）1-氯-3,3,3-三氟丙烯（HCFO-1233zd（E））的方法。 还公开了用于制备氢氟烯烃的综合系统，特别是1233zd（E）。 制造过程包括六个主要单元操作：（1）使用HF同时除去副产物HCl和产物1233zd（E）的HCC-240fa（连续或半间歇模式）的氟化反应; （2）将未反应的HCC-240fa和HF与未氟化的副产物一起回收至（1）; （3）副产物HCl的分离和纯化; （4）将过量的HF分离回（1）; （5）最终产物的纯化，1233zd（E）; 和（6）副产物1233zd（Z）异构化为1233zd（E）以使工艺产率最大化。

公开(公告)号：US08653311B2

公开(公告)日：2014-02-18

申请号：US13860644

申请日：2013-04-11

Applicant: Honeywell International Inc.

Inventor： Ryan Hulse ,  Hang T. Pham ,  Rajiv R. Singh ,  Hsueh S. 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：US10207972B2

公开(公告)日：2019-02-19

申请号：US14955459

申请日：2015-12-01

Applicant: Honeywell International Inc.

Inventor： Daniel C. Merkel ,  Konstantin A. Pokrovski ,  Hsueh Sung Tung ,  Haiyou Wang ,  Ryan Hulse

IPC: C09K5/04 ,  C23G5/028 ,  C11D7/08 ,  C11D7/50 ,  C07C21/18 ,  C07C21/04 ,  C07C19/08

Abstract: Provided are azeotropic or azeotrope-like mixtures of 1,3,3,3-tetrachloroprop-1-ene (HCO-1230zd) and hydrogen fluoride. Such compositions are useful as a feed stock in the production of HFC245fa and HCFO1233zd.

公开(公告)号：US20180057433A1

公开(公告)日：2018-03-01

申请号：US15252537

申请日：2016-08-31

Applicant: Honeywell International Inc.

Inventor： Daniel C. Merkel ,  Konstantin A. Pokrovski ,  Hsueh Sung Tung ,  Haiyou Wang ,  Ryan J. Hulse ,  Hang T. Pham

IPC: C07C17/35 ,  C07C17/21

CPC classification number: C07C17/35 ,  C07C17/04 ,  C07C17/206 ,  C07C17/21 ,  C07C17/25 ,  C07C21/04 ,  C07C21/18 ,  C07C19/08

Abstract: Azeotropic or azeotrope-like mixtures of 1,3,3-trichloro-3-fluoroprop-1-ene (HCFO-1231zd) and hydrogen fluoride (HF). Such compositions are useful as a feed stock or intermediate in the production of 1,1,1,3,3-pentafluoropropane (HFC-245fa),1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), and 1,3,3,3-tetrafluoropropene (HFO-1234ze).

公开(公告)号：US09758450B2

公开(公告)日：2017-09-12

申请号：US15093970

申请日：2016-04-08

Applicant: HONEYWELL INTERNATIONAL INC.

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

IPC: C07C17/38 ,  C07C17/386 ,  C07C17/383 ,  C07C17/25 ,  C07C17/20 ,  C07C21/18 ,  C07C17/087 ,  C07C21/04 ,  C07C19/01 ,  C07C19/08 ,  C07C19/10

CPC classification number: C07C17/206 ,  C07C17/087 ,  C07C17/25 ,  C07C17/38 ,  C07C17/386 ,  C07C19/01 ,  C07C19/08 ,  C07C19/10 ,  C07C21/04 ,  C07C21/18 ,  Y02P20/125 ,  Y02P20/582

Abstract: The invention relates to a separation process whereby 2-chloro-3,3,3-trifluoropropene (1233xf) is separated from a mixture containing other fluorinated organics and high boiling materials such as dimers using azeotropes of HF formed by adding appropriate amounts to the mixture which facilitate separation by, e.g. distillation.

公开(公告)号：US20170247304A1

公开(公告)日：2017-08-31

申请号：US15587824

申请日：2017-05-05

Applicant: HONEYWELL INTERNATIONAL INC.

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

IPC: C07C17/358 ,  C07C5/22 ,  C07B35/08 ,  C07C21/18 ,  C07C17/007

CPC classification number: C07C17/358 ,  C07B35/08 ,  C07B2200/09 ,  C07C5/22 ,  C07C17/007 ,  C07C21/18

Abstract: Disclosed are processes for a high temperature isomerization reaction converting (E)-1-chloro-3,3,3-trifluoropropene to (Z)-1-chloro-3,3,3-trifluoropropene. In certain aspects of the invention, such a process includes contacting a feed stream with a heated surface, where the feed stream includes (E)-1-chloro-3,3,3-trifluoropropene or mixture of (E)-1-chloro-3,3,3-trifluoropropene with (Z)-1-chloro-3,3,3-trifluoropropene. The resulting product stream includes (Z)-1-chloro-3,3,3-trifluoropropene and (E)-1-chloro-3,3,3-trifluoropropene, where the ratio of (Z) isomer to (E) isomer in the product stream is higher than the ratio feed stream. The (E) and (Z) isomers in the product stream may be separated from one another.

公开(公告)号：US20160083316A1

公开(公告)日：2016-03-24

申请号：US14948756

申请日：2015-11-23

Applicant: Honeywell International Inc.

Inventor： Stephen A. Cottrell ,  Hsueh Sung Tung ,  Konstantin A. Pokrovski

IPC: C07C17/383 ,  C07C17/25

CPC classification number: C07C17/383 ,  C07C17/206 ,  C07C17/25 ,  C07C17/38 ,  C07C21/18 ,  Y02P20/125

Abstract: The present invention is directed to processes for the production of 1233zd from 240fa and HF, with or without a catalyst, at a commercial scale. The 240fa and HF are fed to a reactor operating at high pressure. The resulting product stream comprising 1233zd, HCl, HF, and other byproducts is treated to one or more purification techniques including phase separation and one or more distillations to provide purified 1233zd, which meets commercial product specifications, i.e., having a GC purity of 99.5% or greater.

公开(公告)号：US09272969B2

公开(公告)日：2016-03-01

申请号：US13798250

申请日：2013-03-13

Applicant: Honeywell International Inc.

Inventor： Daniel C. Merkel ,  Konstantin A. Pokrovski ,  Hsueh Sung Tung ,  Haiyou Wang ,  Stephen A. Cottrell ,  Hang T. Pham

IPC: C07C19/10 ,  C23G1/02 ,  C23G5/028 ,  C11D7/08 ,  C11D7/50

CPC classification number: C07C19/10 ,  C09K5/044 ,  C11D7/08 ,  C11D7/5036 ,  C23G5/02809

Abstract: Provided are azeotropic or azeotrope-like mixtures of 1,3,3-trichloro-1,1-difluoro-propane (HCFC-242fa) and hydrogen fluoride. Such compositions are useful as a feed stock or intermediate in the production of HFC-245fa and HCFO-1233zd.

Abstract translation: 提供1,3,3-三氯-1,1-二氟 - 丙烷（HCFC-242fa）和氟化氢的共沸或类共沸混合物。 这样的组合物可用作生产HFC-245fa和HCFO-1233zd中的原料或中间体。

公开(公告)号：US09139499B2

公开(公告)日：2015-09-22

申请号：US14633551

申请日：2015-02-27

Applicant: Honeywell International Inc.

Inventor： Daniel C. Merkel ,  Hsueh Sung Tung ,  Konstantin A. Pokrovski ,  Hang T. Pham ,  Ryan Hulse

IPC: C07C17/383

CPC classification number: C07C17/383 ,  C07C19/01

Abstract: Provided are methods for forming azeotropic or azeotrope-like mixtures of 1,1,1,3,3-pentachloro-propane (240fa) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of HFC-245fa and HCFO-1233zd.

Abstract translation: 提供了形成1,1,1,3,3-五氯丙烷（240fa）和氟化氢的共沸或类共沸混合物的方法。 这样的组合物可用作HFC-245fa和HCFO-1233zd生产中的中间体。

公开(公告)号：US20140275644A1

公开(公告)日：2014-09-18

申请号：US13826529

申请日：2013-03-14

Applicant: HONEYWELL INTERNATIONAL INC.

Inventor： Daniel C. Merkel ,  Konstantin A. Pokrovski

IPC: C07C17/358

CPC classification number: C07C17/358 ,  C07C17/38 ,  C07C17/383 ,  C07C17/386 ,  C07C21/18 ,  Y02P20/127

Abstract: The present invention discloses methods to produce cis-1-chloro-3,3,3-trifluoropropene in high yield by the isomerization of trans-1-chloro-3,3,3-trifluoropropene. These isomers are also known as 1233zd(Z) and 1233zd(E), respectively. This is done by using reactive distillation whereby as cis-1-chloro-3,3,3-trifluoropropene is produced, it is removed from the reaction zone. This product removal causes a shift in the thermodynamic equilibrium of the reaction system, forcing the production of additional cis isomer.

Abstract translation: 本发明公开了通过异构化反式-1-氯-3,3,3-三氟丙烯以高产率生产顺式-1-氯-3,3,3-三氟丙烯的方法。 这些异构体也分别称为1233zd（Z）和1233zd（E）。 这通过使用反应蒸馏来进行，由此产生顺式-1-氯-3,3,3-三氟丙烯，将其从反应区除去。 该产物去除导致反应体系的热力学平衡发生变化，迫使产生另外的顺式异构体。