公开(公告)号：US08716538B2

公开(公告)日：2014-05-06

申请号：US13957560

申请日：2013-08-02

Applicant: Honeywell International Inc.

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

IPC: C07C17/00 ,  C07C17/38

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

Abstract: Provided is a process for purifying an organic feedstock comprising (a) distilling a raw organic feedstock comprising hydrogen fluoride, 2-chloro-1,1,1,2-tetrafluoropropane, and 2-chloro-3,3,3-trifluoropropene to produce a first distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a first bottoms stream rich in hydrogen fluoride; (b) cooling said first distillate stream to produce an intermediate composition comprising an organic layer rich in 2-chloro-1,1,1,2-tetrafluoropropane and 2-chloro-3,3,3-trifluoropropene, and an acid layer rich in hydrogen fluoride; and, optionally but preferably, (c) distilling said organic layer to produce a second distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a second bottoms stream comprising a purified organic feedstock substantially free of hydrogen fluoride.

Abstract translation: 提供了一种纯化有机原料的方法，其包括（a）蒸馏包含氟化氢，2-氯-1,1,1,2-四氟丙烷和2-氯-3,3,3-三氟丙烯的原始有机原料以产生 包含2-氯-1,1,1,2-四氟丙烷，2-氯-3,3,3-三氟丙烯和氟化氢的类共沸组合物的第一蒸馏物流和富含氟化氢的第一塔底物流 ; （b）冷却所述第一馏出物流以产生包含富含2-氯-1,1,1,2-四氟丙烷和2-氯-3,3,3-三氟丙烯的有机层和富含酸层的中间组合物 在氟化氢中; 和（c）蒸馏所述有机层以产生包含2-氯-1,1,1,2-四氟丙烷的共沸混合物组合物，2-氯-3,3,3-四氯丙烷的第二馏出物流， 三氟丙烯和氟化氢，以及包含基本上不含氟化氢的纯化有机原料的第二塔底物流。

公开(公告)号：US20240018074A1

公开(公告)日：2024-01-18

申请号：US18218691

申请日：2023-07-06

Applicant: Honeywell International Inc.

Inventor： Richard D. Horwath ,  Haluk Kopkalli ,  Gustavo Cerri ,  Joshua Close ,  Daniel C. Merkel ,  Jennifer W. McClaine ,  Alex C. Fattore ,  Hang T. Pham ,  Carlos Navar ,  Justin Howard

IPC: C07C17/383 ,  C07C17/20 ,  B01D3/14

CPC classification number: C07C17/383 ,  C07C17/206 ,  B01D3/143

Abstract: Two methods for reducing CFC impurities and, in particular, CFC-114, in the HFO-1234ze(E) production process from the reaction of CFC-113 and HF. The first method involves subjecting an intermediate or recycle stream to separation and distillation to purge CFC-113 from the process. The second method involves operating the separation at a higher pressure avoids the formation of an azeotrope between CFC-113 and HFC-245fa. The CFC-113/HFC245fa azeotrope is discussed, as well as other optional processes for removal or mitigation of CFC-113 which include further separations that remove CFC-114 from the HFO-1234ze(E) product and/or CFC-113 from the HFC-245fa feed to produce an HFO-1234ze(E) product that is largely free from CFC-114 and other CFC impurities.

公开(公告)号：US11565992B2

公开(公告)日：2023-01-31

申请号：US17523200

申请日：2021-11-10

Applicant: Honeywell International Inc.

Inventor： Haluk Kopkalli ,  Joshua Close ,  Pramod K W Harikumar Warrier ,  Daniel C. Merkel

IPC: C07C17/386 ,  C07C17/383 ,  C07C51/48 ,  C07C45/83

Abstract: The present disclosure provides azeotrope or azeotrope-like compositions including trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl), methods of forming same, and methods of separating, or breaking, the azeotrope or azeotrope-like compositions of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCl).

公开(公告)号：US20220402843A1

公开(公告)日：2022-12-22

申请号：US17893504

申请日：2022-08-23

Applicant: Honeywell International Inc.

Inventor： Haiyou Wang ,  Daniel C. Merkel

IPC: C07C17/389 ,  C07C17/18

Abstract: A method of producing trifluoroiodomethane (CF3I) includes providing a feedstock comprising trifluoroacetyl iodide (TFAI), passing the feedstock through at least one column charged with carbonaceous materials to remove hydrogen iodide (HI), hydrogen triiodide (HI3) and iodine (I2) from the feedstock, and providing the feedstock to a reactor to produce a trifluoroiodomethane product stream.
Another method of producing trifluoroiodomethane (CF3I) includes providing a feedstock comprising trifluoroacetyl iodide (TFAI) to a reactor to produce a trifluoroiodomethane product stream, and passing the trifluoroiodomethane product stream from the reactor through at least one column charged with carbonaceous materials to remove hydrogen iodide (HI), hydrogen triiodide (HI3) and iodine (I2) from the trifluoroiodomethane product stream.

公开(公告)号：US11453631B2

公开(公告)日：2022-09-27

申请号：US17495511

申请日：2021-10-06

Applicant: Honeywell International Inc.

Inventor： Haiyou Wang ,  Daniel C. Merkel

IPC: C07C17/389 ,  C07C17/18 ,  C07C19/16

Abstract: A method of producing trifluoroiodomethane (CF3I) includes providing a feedstock comprising trifluoroacetyl iodide (TFAI), passing the feedstock through at least one column charged with carbonaceous materials to remove hydrogen iodide (HI), hydrogen triiodide (HI3) and iodine (I2) from the feedstock, and providing the feedstock to a reactor to produce a trifluoroiodomethane product stream.
Another method of producing trifluoroiodomethane (CF3I) includes providing a feedstock comprising trifluoroacetyl iodide (TFAI) to a reactor to produce a trifluoroiodomethane product stream, and passing the trifluoroiodomethane product stream from the reactor through at least one column charged with carbonaceous materials to remove hydrogen iodide (HI), hydrogen triiodide (HI3) and iodine (I2) from the trifluoroiodomethane product stream.

公开(公告)号：US20220219981A1

公开(公告)日：2022-07-14

申请号：US17572547

申请日：2022-01-10

Applicant: Honeywell International Inc.

Inventor： Yuon Chiu ,  Haiyou Wang ,  Haluk Kopkalli ,  Christian Jungong ,  Haridasan K. Nair ,  Rajiv Ratna Singh ,  Daniel C. Merkel ,  Tao Wang ,  Terris Yang ,  Richard Wilcox

IPC: C01B7/14 ,  B01D53/04

Abstract: A method of removing water from a mixture of iodine (I2) and water includes providing a mixture comprising iodine and water and: contacting the mixture with an adsorbent to selectively adsorb water from the mixture, contacting the mixture with a concentrated acid to absorb water from the mixture, separating the water from mixture by distillation, contacting the mixture with a gas that is inert to iodine (I2), contacting the mixture with hydrogen iodide (HI), or combinations thereof.

公开(公告)号：US20220112226A1

公开(公告)日：2022-04-14

申请号：US17495506

申请日：2021-10-06

Applicant: Honeywell International Inc.

Inventor： Haiyou Wang ,  Haridasan K. Nair ,  Daniel C. Merkel ,  Selma Bektesevic ,  Terris Yang

IPC: C07F13/00

Abstract: The present disclosure provides a composition including trifluoroacetyl iodide, at least one organic impurity and at least one inorganic impurity. The at least one organic impurity includes at least one of: difluoroiodomethane, pentafluoroiodoethane, iodomethane, iodopropane, dichlorotetrafluoroethane, dichlorotrifluoroethane, trichlorotrifluoroethane, methyltrifluoroacetate, trifluoroacetic anhydride, difluorobutane and methyl propane. The at least one inorganic impurity includes at least one of: hydrogen iodide, hydrogen chloride, iodine and hydrogen triiodide.

公开(公告)号：US11123710B2

公开(公告)日：2021-09-21

申请号：US13857013

申请日：2013-04-04

Applicant: HONEYWELL INTERNATIONAL INC.

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

IPC: B01J32/00 ,  B01J23/44 ,  C07C17/354 ,  B01J23/48 ,  B01J23/40 ,  B01J35/10 ,  B01J21/04 ,  B01J37/18 ,  B01J23/70 ,  B01J23/36

Abstract: The present invention relates, in part, to an alpha-alumina support for a hydrogenation catalyst useful in hydrogenating fluoroolefins. In certain aspects, it relates to a method for hydrogenating a compound by contacting an olefin reactant having at least one carbon-fluorine bond, with a supported hydrogenation catalyst. The reaction results in a product that includes a hydrogenated derivative of the olefin. In certain embodiments, the supported hydrogenation catalyst includes a zero-valent metal disposed on an alpha-alumina support.

公开(公告)号：US10508067B2

公开(公告)日：2019-12-17

申请号：US15888331

申请日：2018-02-05

Applicant: HONEYWELL INTERNATIONAL INC.

Inventor： George R. Cook ,  Haluk Kopkalli ,  Stephen A. Cottrell ,  Yuon Chiu ,  Peter Scheidle ,  Daniel C. Merkel

IPC: C07C17/23 ,  C07C17/25

Abstract: A process for the manufacture of halogenated olefins in semi-batch mode by dehydrohalogenation of halogenated alkanes in the presence of an aqueous base such as KOH which simultaneously neutralizes the resulting hydrogen halide. During the process, aqueous base is continuously added to the haloalkane which results in better yields, lower by-product formation and safer/more controllable operation.

公开(公告)号：US20190210944A1

公开(公告)日：2019-07-11

申请号：US15864730

申请日：2018-01-08

Applicant: Honeywell International Inc.

Inventor： Haiyou Wang ,  Terris Yang ,  Daniel C. Merkel ,  Haluk Kopkalli ,  Gustavo Cerri ,  Yuon Chiu ,  Richard D. Horwath

IPC: C07C17/25 ,  C07C17/386 ,  C07C17/395 ,  C07C21/18 ,  B01D3/00 ,  B01D3/36

CPC classification number: C07C17/25 ,  B01D3/002 ,  B01D3/36 ,  C07C17/386 ,  C07C17/395 ,  C07C21/18

Abstract: The present disclosure provides various manufacturing processes for the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf or 1234yf). Such methods may allow for the improved yields, more economical processes, and waste reduction in the production of 1234yf and subsequent processes.