公开(公告)号：US20190263736A1

公开(公告)日：2019-08-29

申请号：US16112058

申请日：2018-08-24

Applicant: HONEYWELL INTERNATIONAL INC.

Inventor： Sudip Mukhopadhyay ,  Hsueh S. Tung ,  Michael Van Der Puy ,  Daniel C. Merkel ,  Jing Ji Ma ,  Cheryl L. Bortz ,  Barbara A. Light ,  Steven D. Phillips ,  Rajesh K. Dubey

IPC: C07C17/25 ,  C07C21/18 ,  C07C17/278 ,  C07C17/272 ,  C07C17/269 ,  C07C17/26 ,  C07C17/00 ,  C07C17/20 ,  C07C17/087 ,  C07C17/04 ,  C07C17/21

Abstract: Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF═CH2 (1234yf). Three steps may be used in preferred embodiments in which a feedstock such as CCl2═CClCH2Cl (which may be purchased or synthesized from 1,2,3-trichloropropane) is fluorinated (preferably with HF in gas-phase in the presence of a catalyst) to synthesize a compound such as CF3CCl═CH2, preferably in a 80-96% selectivity. The CF3CCl═CH2 is preferably converted to CF3CFClCH3 (244-isomer) using a SbCl5 as the catalyst which is then transformed selectively to 1234yf, preferably in a gas-phase catalytic reaction using activated carbon as the catalyst. For the first step, a mixture of Cr2O3 and FeCl3/C is preferably used as the catalyst to achieve high selectivity to CF3CCl═CH2 (96%). In the second step, SbCl5/C is preferably used as the selective catalyst for transforming 1233xf to 244-isomer, CF3CFClCH3. The intermediates are preferably isolated and purified by distillation and used in the next step without further purification, preferably to a purity level of greater than about 95%.

公开(公告)号：US20190152882A1

公开(公告)日：2019-05-23

申请号：US16177707

申请日：2018-11-01

Applicant: Honeywell International Inc.

Inventor： Christian Jungong ,  Daniel C. Merkel ,  Haiyou Wang

IPC: C07C17/20 ,  C07C21/18

Abstract: A method for producing 1,3,3,3-tetrafluoropropene (HFO-1234ze, or 1234ze) from 1-chloro-3,3,3-trifluoropopene (HCFO-1233zd, or 1233zd). In one embodiment, HFO-1233zd is subjected to a disproportionation reaction in the presence of a catalyst at an elevated temperature to produce HFO-1234ze as well as 3,3-dichloro-1,1-difluoropropene (HCFO-1232zc). The catalyst may be at least one of a chromium oxyfluoride catalyst, a chromium oxide catalyst, or a metal fluoride catalyst. The reaction may be conducted in the vapor phase at a temperature between 100° C. and 450° C. Advantageously, in the present method, substantially no hydrogen fluoride (HF) is used as a reactant, and substantially no HF is produced as a product.

公开(公告)号：US10259760B2

公开(公告)日：2019-04-16

申请号：US15289546

申请日：2016-10-10

Applicant: HONEYWELL INTERNATIONAL INC.

Inventor： Hang T. Pham ,  Daniel C. Merkel ,  Konstantin A. Pokrovski ,  Hsueh S. Tung ,  Rajiv R. Singh

IPC: C11D7/50 ,  C07C17/20 ,  C07C17/38 ,  C07C17/383 ,  C07C21/18

Abstract: Provided are azeotropic and azeotrope-like compositions of 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) 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).

公开(公告)号：US10131597B2

公开(公告)日：2018-11-20

申请号：US14355894

申请日：2012-11-02

Applicant: HONEYWELL INTERNATIONAL INC.

Inventor： Haiyou Wang ,  Hsueh Sung Tung ,  Selma Bektesevic ,  Daniel C. Merkel ,  Haluk Kopkalli ,  Yuon Chiu

IPC: C07C17/20 ,  B01J23/26 ,  C07C17/087 ,  C07C17/25 ,  C07C17/42 ,  B01J21/04 ,  B01J23/34 ,  B01J23/745 ,  B01J23/75 ,  B01J23/755 ,  B01J27/10 ,  B01J27/12 ,  B01J27/138

Abstract: The present invention relates, in part, to the discovery that, during the fluorination of certain fluoroolefin starting reagents, oligomerization/polymerization of such reagents reduces the conversion process and leads to increased catalyst deactivation. The present invention also illustrates that vaporizing such starting reagents in the presence of one or more organic co-feed reduces such oligomerization/polymerization and improves catalytic stability.

公开(公告)号：US10125068B2

公开(公告)日：2018-11-13

申请号：US15445407

申请日：2017-02-28

Applicant: HONEYWELL INTERNATIONAL INC.

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

IPC: C07C17/395 ,  C07C21/18 ,  C07C17/25 ,  C07C17/383 ,  C07C19/10 ,  B01J23/44 ,  B01J27/138 ,  B01J19/12 ,  B01J27/10 ,  B01D3/00 ,  B01D3/10 ,  B01D11/04

Abstract: The instant invention relates to a process and method for manufacturing 2,3,3,3-tetrafluoropropene by dehydrohalogenating a reactant stream of 2-chloro-1,1,1,2-tetrafluoropropane that is substantially free from impurities, particularly halogenated propanes, propenes, and propynes.

公开(公告)号：US10029964B2

公开(公告)日：2018-07-24

申请号：US15251468

申请日：2016-08-30

Applicant: Honeywell International Inc.

Inventor： Haluk Kopkalli ,  Hang T. Pham ,  Daniel C. Merkel

IPC: C07C21/22 ,  B01D3/36 ,  C07C17/383

Abstract: Azeotropic or azeotrope-like compositions of 3,3,3-trifluoropropyne and water, such as from about 1 to about 50 wt. % water and from about 50 to about 99 wt. % 3,3,3-trifluoropropyne, based on the combined weight of the water and 3,3,3-trifluoropropyne, and methods of producing essentially water free 3,3,3-trifluoropropyne.

公开(公告)号：US09994502B1

公开(公告)日：2018-06-12

申请号：US15883581

申请日：2018-01-30

Applicant: Honeywell International Inc.

Inventor： Daniel C. Merkel ,  Hsueh Sung Tung

IPC: C07C17/25 ,  C07C17/20 ,  C07C17/383

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

Abstract: A process for enhancing the selective and efficient production of (E)-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E), or 1233zd(E)). During the manufacture of HCFO-1233zd(E) by fluorination of 1,1,1,3,3-pentachloropropane (HCC-240fa), a by-product of 1,3,3-trichloro-1,1-difluoropropane (HCFC-242fa) is separated and then dehydrochlorinated to form 1,3-chloro-3,3-difluoropropene (HCFO-1232zd). The HCFO-1232zd is then fluorinated to form HCFO-1233zd(E).

公开(公告)号：US09950974B2

公开(公告)日：2018-04-24

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: C07C21/18 ,  C07C17/04 ,  C07C17/20 ,  C07C17/25 ,  C07C17/35 ,  C07C17/21 ,  C07C21/04

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：US20180056210A1

公开(公告)日：2018-03-01

申请号：US15688254

申请日：2017-08-28

Applicant: Honeywell International Inc.

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

IPC: B01D3/36 ,  C07C19/10 ,  C07C21/18 ,  C01B7/19

CPC classification number: B01D3/36 ,  C01B7/191 ,  C01B7/197 ,  C07C17/386 ,  C07C19/10 ,  C07C21/18

Abstract: A method for separating halocarbons and, in particular, a method for separating (Z)-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(Z), or simply 1233zd(Z)) and 1-chloro-1,3,3,3-tetrafluoropropane (HCFC-244fa, or simply 244fa) via distillation by adding a third component, hydrogen fluoride (HF), forming a binary azeotrope of 1233zd(Z) and HF. The binary 1233zd(Z)/HF azeotrope may then be recovered from the distillation column as an overhead stream which includes only a relatively minor amount of 244fa, while the 244fa may be recovered from the distillation column as a bottoms stream which includes only relatively minor amounts of 1233zd(Z) and HF.

公开(公告)号：US09643903B2

公开(公告)日：2017-05-09

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: C07C17/20 ,  B01D3/00 ,  C01B7/07 ,  C07C17/25 ,  C07C17/358 ,  C07C17/383 ,  C07C21/18

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.