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.

公开(公告)号：US20190144364A1

公开(公告)日：2019-05-16

申请号：US16004567

申请日：2018-06-11

Applicant: HONEYWELL INTERNATIONAL INC.

Inventor： Yuon Chiu ,  Stephen A. Cottrell ,  Hsueh Sung Tung ,  Haluk Kopkalli ,  Gustavo Cerri

IPC: C07C17/25 ,  C07C21/18 ,  C07C17/23 ,  B01J19/14 ,  B01J19/00 ,  C07C17/38 ,  C07C17/354 ,  B01J7/00

Abstract: A method for producing 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene using a single set of four unit operations, the unit operations being (1) hydrogenation of a starting material comprising hexafluoropropene and optionally recycled 1,1,1,2,3-pentafluoropropene; (2) separation of the desired intermediate hydrofluoroalkane, such as 1,1,1,2,3,3-hexafluoropropane and/or 1,1,1,2,3-pentafluoropropane; (3) dehydrofluorination of the intermediate hydrofluoroalkane to produce the desired 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene, followed by another separation to isolate the desired product and, optionally, recycle of the 1,1,1,2,3-pentafluoropropene.

公开(公告)号：US09994503B2

公开(公告)日：2018-06-12

申请号：US15090027

申请日：2016-04-04

Applicant: HONEYWELL INTERNATIONAL INC.

Inventor： Yuon Chiu ,  Stephen A. Cottrell ,  Hsueh Sung Tung ,  Haluk Kopkalli ,  Gustavo Cerri

IPC: B01J19/00 ,  B01J19/08 ,  B01J19/24 ,  C07C17/00 ,  C07C17/23 ,  C07C17/25 ,  C07C17/35 ,  C07C17/354 ,  C07C17/38 ,  C07C21/00 ,  C07C21/02 ,  C07C21/18 ,  B01J7/00 ,  B01J19/14

CPC classification number: C07C17/25 ,  B01J7/00 ,  B01J19/0046 ,  B01J19/14 ,  B01J2219/00452 ,  B01J2219/0059 ,  B01J2219/00594 ,  B01J2219/0072 ,  B01J2219/00759 ,  C07C17/23 ,  C07C17/354 ,  C07C17/38 ,  C07C21/18 ,  C07C19/08

Abstract: A method for producing 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene using a single set of four unit operations, the unit operations being (1) hydrogenation of a starting material comprising hexafluoropropene and optionally recycled 1,1,1,2,3-pentafluoropropene; (2) separation of the desired intermediate hydrofluoroalkane, such as 1,1,1,2,3,3-hexafluoropropane and/or 1,1,1,2,3-pentafluoropropane; (3) dehydrofluorination of the intermediate hydrofluoroalkane to produce the desired 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene, followed by another separation to isolate the desired product and, optionally, recycle of the 1,1,1,2,3-pentafluoropropene.

公开(公告)号：US20170239638A1

公开(公告)日：2017-08-24

申请号：US15590688

申请日：2017-05-09

Applicant: Honeywell International, Inc.

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

IPC: B01J19/24 ,  C07C21/18 ,  C07C17/25 ,  B01J4/00 ,  C07C17/20

CPC classification number: B01J19/24 ,  B01J4/002 ,  B01J8/025 ,  B01J8/0278 ,  B01J19/02 ,  B01J19/26 ,  B01J2208/00902 ,  C07C17/206 ,  C07C17/25 ,  C07C21/18

Abstract: The invention relates to a process to prepare tetrahalopropenes, such as 2-chloro-3,3,3-trifluoropropene (1233xf). The process comprises atomizing a feed material, such as 1,2,3-tetrachloropropene (1230xa) and the like, and mixing it with superheated HF to form a vaporized composition of feed material and HF with substantially instantaneous contact with a vapor phase fluorination catalyst. The invention extends catalyst life and forestalls catalyst deactivation.

公开(公告)号：US09675950B2

公开(公告)日：2017-06-13

申请号：US14604790

申请日：2015-01-26

Applicant: Honeywell International Inc.

Inventor： Yuon Chiu ,  Haluk Kopkalli ,  Richard Durick Horwath

IPC: B01J8/06 ,  B01J8/04 ,  C07C17/354 ,  B01J8/02

CPC classification number: B01J8/067 ,  B01J8/0207 ,  B01J8/048 ,  B01J8/0492 ,  B01J8/0496 ,  B01J8/065 ,  B01J2208/00221 ,  B01J2208/00902 ,  B01J2208/00929 ,  B01J2208/02 ,  B01J2208/065 ,  C07C17/354 ,  Y02P20/124 ,  C07C19/08

Abstract: The present invention is directed to a combination reactor system for exothermic reactions comprising a trickle-bed reactor and a shell-and-tube reactor. This combination allows the system to efficiently remove heat while also providing the ability to control both the temperature and/or reaction progression. The trickle-bed reactor removes heat efficiently from the system by utilizing latent heat and does not require the use of a cooling or heating medium. The shell-and-tube reactor is used to further progress the reaction and provides a heat exchanger in order to introduce fluid at the desired temperature in the shell-and-tube reactor. Also, additional reactant or reactants and/or other fluids may be introduced to the shell-and-tube section of the reactor under controlled temperature conditions.

公开(公告)号：US20160304421A1

公开(公告)日：2016-10-20

申请号：US15090027

申请日：2016-04-04

Applicant: HONEYWELL INTERNATIONAL INC.

Inventor： Yuon Chiu ,  Stephen A. Cottrell ,  Hsueh Sung Tung ,  Haluk Kopkalli ,  Gustavo Cerri

IPC: C07C17/25 ,  B01J19/14 ,  B01J7/00 ,  B01J19/00 ,  C07C17/354 ,  C07C17/38

CPC classification number: C07C17/25 ,  B01J7/00 ,  B01J19/0046 ,  B01J19/14 ,  B01J2219/00452 ,  B01J2219/0059 ,  B01J2219/00594 ,  B01J2219/0072 ,  B01J2219/00759 ,  C07C17/23 ,  C07C17/354 ,  C07C17/38 ,  C07C21/18 ,  C07C19/08

Abstract: A method for producing 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene using a single set of four unit operations, the unit operations being (1) hydrogenation of a starting material comprising hexafluoropropene and optionally recycled 1,1,1,2,3-pentafluoropropene; (2) separation of the desired intermediate hydrofluoroalkane, such as 1,1,1,2,3,3-hexafluoropropane and/or 1,1,1,2,3-pentafluoropropane; (3) dehydrofluorination of the intermediate hydrofluoroalkane to produce the desired 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene, followed by another separation to isolate the desired product and, optionally, recycle of the 1,1,1,2,3-pentafluoropropene.

Abstract translation: 使用单组四个单元操作制备1,1,1,2-四氟丙烯和/或1,1,1,2,3-五氟丙烯的方法，单元操作是（1）将包含六氟丙烯的原料氢化 和任选的再循环的1,1,1,2,3-五氟丙烯; （2）所需中间体氢氟烷烃如1,1,1,2,3,3-六氟丙烷和/或1,1,1,2,3-五氟丙烷的分离; （3）中间体氢氟烷烃的脱氟化氢以产生所需的1,1,1,2-四氟丙烯和/或1,1,1,2,3-五氟丙烯，然后进行另一次分离以分离所需产物，并且任选地再循环 的1,1,1,2,3-五氟丙烯。

公开(公告)号：US09296670B2

公开(公告)日：2016-03-29

申请号：US14377727

申请日：2013-02-08

Applicant: Honeywell International, Inc.

Inventor： Haiyou Wang ,  Hsueh S. Tung ,  Haluk Kopkalli ,  Yuon Chiu ,  Gustavo Cerri ,  Jeffrey Ball ,  Philip L. Da Prato ,  Xuehui Sun ,  Mario Joseph Nappa

IPC: C07C17/23 ,  C07C17/395 ,  C07C17/06 ,  C07C17/087 ,  C07C17/25 ,  C07C17/386 ,  C07C17/389 ,  B01J27/08

CPC classification number: C07C17/395 ,  B01J27/08 ,  C07C17/06 ,  C07C17/087 ,  C07C17/23 ,  C07C17/25 ,  C07C17/386 ,  C07C17/389 ,  Y02P20/582 ,  C07C19/10 ,  C07C21/18

Abstract: A method for forming 2,3,3,3-tetrafluoropropene (HFO-1234yf) comprising providing a dehydrochlorination starting material having relatively low concentrations of 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), especially and preferable less than about 8.0% when the dehydrochlorination reaction utilizes no substantial amount of catalyst or catalyst comprising austenitic nickel-based materials.

Abstract translation: 一种形成2,3,3,3-四氟丙烯（HFO-1234yf）的方法，包括提供具有较低浓度的2-氯-3,3,3-三氟丙烯（HCFO-1233xf）的脱氯化氢原料，特别优选较少 当脱氯化氢反应不使用显着量的包含奥氏体镍基材料的催化剂或催化剂时，约为8.0％。

公开(公告)号：US09290424B2

公开(公告)日：2016-03-22

申请号：US13827302

申请日：2013-03-14

Applicant: HONEYWELL INTERNATIONAL INC.

Inventor： Stephen A. Cottrell ,  John J. Senetar ,  Hsueh S. Tung ,  Daniel C. Merkel ,  Yuon Chiu ,  Haluk Kopkalli

IPC: C07C17/354 ,  C07C17/25

CPC classification number: C07C17/354 ,  C07C17/25 ,  C07C19/08

Abstract: In certain aspects, the present invention relates to methods for increasing the cost efficiency and safety of the hydrogenation of a fluorinated olefin by controlling the reaction conditions and parameters. In further aspects, the hydrogenation reaction is provided in a two stage reaction wherein the reactant amounts, temperature and other parameters are controlled such that the conversion percentage, selectivity, and reaction parameters are all within commercially acceptable levels.

Abstract translation: 在某些方面，本发明涉及通过控制反应条件和参数来提高氟化烯烃氢化的成本效率和安全性的方法。 在另外的方面，氢化反应在两阶段反应中提供，其中控制反应物的量，温度和其它参数，使得转化百分比，选择性和反应参数都在商业上可接受的水平。

公开(公告)号：US20150225317A1

公开(公告)日：2015-08-13

申请号：US14695579

申请日：2015-04-24

Applicant: Honeywell International, Inc.

Inventor： Haluk Kopkalli ,  Daniel C. Merkel ,  Ron Joseph Roof

IPC: C07C17/087

CPC classification number: C07C17/087 ,  C07C17/08 ,  C07C17/206 ,  C07C17/23 ,  C07C17/25 ,  C07C19/10 ,  C07C21/18 ,  C07C19/08

Abstract: The invention relates to a process to produce HCFC-244bb from HCFO-1233xf wherein, in one embodiment, one or more co-feed species having a normal boiling point of between about −80° C. to about 0° C., such as HFC-245cb, is added to the reaction at a pressure of at least about 100 psig; and in another embodiment it is added to maintain a mole ratio of HFC-245cb to HCFO-1233xf of between about 0.005:1 to about 1:1. The HFC-245cb may be added as recycled by-product of the reaction and/or added as fresh feed. The HFC-245cb provides elevated pressures to the reaction thereby facilitating reactor operation, mixing and HCFC-244bb product removal. Other co-feed species are also disclosed.

Abstract translation: 本发明涉及一种从HCFO-1233xf生产HCFC-244bb的方法，其中在一个实施方案中，一种或多种正常沸点在约-80℃至约0℃之间的共进料物质，例如 将HFC-245cb在至少约100psig的压力下加入到反应中; 并且在另一个实施方案中，加入以保持HFC-245cb与HCFO-1233xf的摩尔比在约0.005:1至约1:1之间。 可以将HFC-245cb作为反应的副产物加入和/或作为新鲜饲料加入。 HFC-245cb为反应提供升高的压力，从而便于反应器操作，混合和HCFC-244bb产品的去除。 还公开了其他共同饲料物种。