公开(公告)号：US09586876B2

公开(公告)日：2017-03-07

申请号：US14318746

申请日：2014-06-30

Applicant: HONEYWELL INTERNATIONAL INC.

Inventor： Haiyou Wang ,  Hsueh Sung Tung ,  Rajiv R. Singh ,  Ian Shankland

IPC: C07C17/25 ,  C07C17/04 ,  C07C17/383 ,  C07C17/395 ,  C07C21/18 ,  C07C19/08

CPC classification number: C07C19/08 ,  C07C17/04 ,  C07C17/25 ,  C07C17/383 ,  C07C17/395 ,  C07C21/18 ,  C07C19/10

Abstract: The present invention discloses a manufacturing process to produce high purity 1234yf from 245eb, which preferably includes the removal of impurities present in 245eb raw material, the dehydrofluorination of 245eb, and the removal of impurities present in final crude product. The disclosed manufacturing process allows the production of a 1234yf product with lower the levels of 1225ye and/or trifluoropropene, preferably in amounts of less than about 500, and 50 ppm, respectively.

Abstract translation: 本发明公开了一种从245eb生产高纯度1234yf的制造方法，其优选包括去除245eb原料中存在的杂质，245eb的脱氟化氢和去除最终粗产物中存在的杂质。 所公开的制造方法允许生产具有较低1225ye和/或三氟丙烯含量的1234yf产品，优选分别小于约500ppm和50ppm。

公开(公告)号：US20170050905A1

公开(公告)日：2017-02-23

申请号：US15232089

申请日：2016-08-09

Applicant: Honeywell International, Inc.

Inventor： Haiyou Wang ,  Hsueh Sung Tung

IPC: C07C17/389

CPC classification number: C07C17/389 ,  C07C21/18

Abstract: This invention pertains to a method for removing acidic impurity from halogenated olefins, especially methods for removing acidic impurity from halogenated propenes, and even more particularly to methods for removing acidic impurity from 1,3,3,3-tetrafluoro-1-propene (HFO-1234ze), 2,3,3,3-tetrafluoro-1-propene (HFO-1234yf), 1-chloro-3,3,3-trifluoro-1-propene (HCFO-1233zd), and 2-chloro-3,3,3-trifluoro-1-propene (HCFO-1233xf). The method is conducted by passing the halogenated olefin stream, in liquid or gas form, through a solid adsorbent bed, which contains at least one acid reactive agent.

Abstract translation: 本发明涉及从卤代烯烃中除去酸性杂质的方法，特别是从卤化丙烯除去酸性杂质的方法，更具体地说，涉及从1,3,3,3-四氟-1-丙烯（HFO）中除去酸性杂质的方法 -1234ze），2,3,3,3-四氟-1-丙烯（HFO-1234yf），1-氯-3,3,3-三氟-1-丙烯（HCFO-1233zd）和2-氯-3 ，3,3-三氟-1-丙烯（HCFO-1233xf）。 该方法通过使液体或气体形式的卤代烯烃流通过含有至少一种酸反应剂的固体吸附剂床进行。

公开(公告)号：US09540295B2

公开(公告)日：2017-01-10

申请号：US14348819

申请日：2012-09-29

Applicant: HONEYWELL INTERNATIONAL INC.

Inventor： Selma Bektesevic ,  Hsueh Sung Tung ,  Haiyou Wang

IPC: C07C17/20 ,  C07C17/25 ,  C07C17/087 ,  C07C17/21

CPC classification number: C07C17/21 ,  C07C17/087 ,  C07C17/20 ,  C07C17/206 ,  C07C17/25 ,  C07C21/18 ,  C07C19/10

Abstract: The present invention relates, in part, to the discovery that high temperatures during the fluorination of 1,1,2,3-tetrachloropropene (HCO-1230xa) to 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) results in catalyst instability, reduced selectivity of the conversion, and/or the formation of one or more undesirable by-products. By controlling the reaction temperature, it is shown that the catalyst life may be extended and the selectivity of the reaction improved. Such control similarly results in an overall improvement in the production of certain hydrofluoroolefins, particularly 2,3,3,3-tetrafluoropropene (HFO-1234yf).

Abstract translation: 本发明部分地涉及在1,1,2,3-四氯丙烯（HCO-1230xa）氟化成2-氯-3,3,3-三氟丙烯（HCFO-1233xf）期间的高温结果的发现 催化剂不稳定性，转化率的选择性降低，和/或一种或多种不期望的副产物的形成。 通过控制反应温度，可以看出可延长催化剂寿命，提高反应选择性。 这种控制类似地导致某些氢氟烯烃，特别是2,3,3,3-四氟丙烯（HFO-1234yf）的生产的总体改进。

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：US20150368169A1

公开(公告)日：2015-12-24

申请号：US14721575

申请日：2015-05-26

Applicant: HONEYWELL INTERNATIONAL INC.

Inventor： Haiyou Wang ,  Hsueh Sung Tung

IPC: C07C17/25

Abstract: A process for making a fluorinated olefin having the step of dehydrochlorinating a hydrochlorofluorocarbon having at least one hydrogen atom and at least one chlorine atom on adjacent carbon atoms, preferably carried out in the presence of a catalyst selected from the group consisting of (i) one or more metal halides, (ii) one or more halogenated metal oxides, (iii) one or more zero-valent metals/metal alloys, (iv) a combination of two or more of the foregoing.

公开(公告)号：US20150105596A1

公开(公告)日：2015-04-16

申请号：US14507914

申请日：2014-10-07

Applicant: Honeywell International Inc.

Inventor： Haiyou Wang ,  Hsueh Sung Tung

IPC: C07C17/20

CPC classification number: C07C17/206 ,  C07B2200/09 ,  C07C17/25 ,  C07C21/18

Abstract: This invention relates to methods and systems for producing hydrochlorofluoro-olefins, particularly 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) by the fluorination of a starting material selected from the group consisting of 1,1,1,3,3-pentachloropropane (HCC-240fa), 1,1,3,3-tetrachloropropene, and 1,1,1,3-tetrachloropropene, alone or in combination, in an ionic liquid.

Abstract translation: 本发明涉及通过氟化起始原料来制备氢氯氟烯烃，特别是1-氯-3,3,3-三氟丙烯（HCFO-1233zd）的方法和系统，该原料选自1,1,1,3 ，3-五氯丙烷（HCC-240fa），1,1,3,3-四氯丙烯和1,1,1,3-四氯丙烯，在离子液体中单独或组合使用。

公开(公告)号：US20150005536A1

公开(公告)日：2015-01-01

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: C07C17/395 ,  C07C17/23

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：US08907147B2

公开(公告)日：2014-12-09

申请号：US14168044

申请日：2014-01-30

Applicant: Honeywell International Inc.

Inventor： Haiyou Wang ,  Hsueh Sung Tung ,  Joshua Close ,  Terris Tianxue Yang

IPC: C07C17/25 ,  C07C17/358 ,  C07C17/02 ,  C07C17/10

CPC classification number: C07C17/358 ,  C07C17/02 ,  C07C17/04 ,  C07C17/10 ,  C07C17/25 ,  C07C17/275 ,  C07C17/383 ,  Y02P20/127 ,  C07C19/01 ,  C07C21/04

Abstract: The present invention provides an improved process for producing 1,1,2,3-tetrachloropropene. By using a first reactive distillation column for HCC-250fb dehydrochlorination, and a second reactive distillation column for HCC-240db dehydrochlorination/HCC-1230xf isomerization, the 1,1,2,3-tetrachloropropene manufacturing process can be greatly simplified, resulting in reduced equipment use, energy use, as well as increased productivity.

Abstract translation: 本发明提供一种制备1,1,2,3-四氯丙烯的改进方法。 通过使用用于HCC-250fb脱氯化氢的第一反应蒸馏塔和用于HCC-240db脱氯化氢/ HCC-1230xf异构化的第二反应蒸馏塔，可大大简化1,1,2,3-四氯丙烯制造方法，导致减少 设备使用，能源使用，以及提高生产力。

公开(公告)号：US08846990B2

公开(公告)日：2014-09-30

申请号：US14351735

申请日：2012-10-10

Applicant: Honeywell International Inc.

Inventor： Haiyou Wang ,  Hsueh Sung Tung

IPC: C07C17/00 ,  C07C17/38 ,  C07C17/25 ,  C23G5/00 ,  C07C17/20

CPC classification number: C07C17/25 ,  B01J19/02 ,  B01J2219/0277 ,  B01J2219/0286 ,  C07C17/20 ,  C07C17/38 ,  C23G5/00 ,  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：US20140275660A1

公开(公告)日：2014-09-18

申请号：US13804738

申请日：2013-03-14

Applicant: HONEYWELL INTERNATIONAL INC.

Inventor： Haiyou Wang ,  Huseh Sung Tung ,  Selma Bektesevic

IPC: C07C17/38

CPC classification number: C07C17/42 ,  C07C17/25 ,  C07C17/278 ,  C07C17/38 ,  C07C17/386 ,  C07C21/04

Abstract: This invention is directed to a method for mitigating HCl generation during 1230xa purification, which comprises the steps of; (a) adding a chelating agent into 1230xa crude, and (b) conducting the 1230xa purification in the presence of said chelating agent at a quantity sufficient to reduce or prevent 1230xa decomposition. Examples of chelating agent include tributyl phosphate (TBP), tripropyl phosphate (TPP), and triethyl phosphate (TEP). The concentration of chelating agent in 1230xa crude can range from 0.001 to 20 wt %, preferably from 0.01 to 10 wt %, and more preferably from 0.1 to 5 wt %.

Abstract translation: 本发明涉及一种减轻1230xa纯化期间HCl产生的方法，其包括以下步骤： （a）向1230xa粗品中加入螯合剂，和（b）在所述螯合剂存在下，以足以减少或防止1230×分解的量进行1230xa纯化。 螯合剂的实例包括磷酸三丁酯（TBP），磷酸三丙基酯（TPP）和磷酸三乙酯（TEP）。 1230xa原料中螯合剂的浓度可以为0.001〜20重量％，优选为0.01〜10重量％，更优选为0.1〜5重量％。