WO2006033771A2 - Chemical production processes and systems - Google Patents

Chemical production processes and systems Download PDF

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Publication number
WO2006033771A2
WO2006033771A2 PCT/US2005/030349 US2005030349W WO2006033771A2 WO 2006033771 A2 WO2006033771 A2 WO 2006033771A2 US 2005030349 W US2005030349 W US 2005030349W WO 2006033771 A2 WO2006033771 A2 WO 2006033771A2
Authority
WO
WIPO (PCT)
Prior art keywords
chemical production
production process
halocarbon
catalyst composition
reactor
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2005/030349
Other languages
English (en)
French (fr)
Other versions
WO2006033771A3 (en
WO2006033771A8 (en
Inventor
Vicki Hedrick
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Great Lakes Chemical Corp
PCBU Services Inc
Original Assignee
Great Lakes Chemical Corp
PCBU Services Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Great Lakes Chemical Corp, PCBU Services Inc filed Critical Great Lakes Chemical Corp
Priority to US11/661,166 priority Critical patent/US7884255B2/en
Priority to EP05791273A priority patent/EP1789373A4/en
Priority to JP2007530144A priority patent/JP2008510831A/ja
Publication of WO2006033771A2 publication Critical patent/WO2006033771A2/en
Publication of WO2006033771A3 publication Critical patent/WO2006033771A3/en
Anticipated expiration legal-status Critical
Publication of WO2006033771A8 publication Critical patent/WO2006033771A8/en
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/20—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising free carbon; comprising carbon obtained by carbonising processes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
    • C07C17/04—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C07C17/21—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms with simultaneous increase of the number of halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/19—Halogenated dienes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/19—Halogenated dienes
    • C07C21/20—Halogenated butadienes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00002—Chemical plants
    • B01J2219/00004—Scale aspects
    • B01J2219/00006—Large-scale industrial plants
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Definitions

  • the present invention relates to the field of chemical production processes and ⁇ systems and more specifically to the production of hydrogenated olefins.
  • Hydrogenated olefins can be produced in numerous ways, including via elimination reactions for example. Hydrogenating an olefin, particularly halogenated olefins, can prove to be difficult for at least the reason that the drawback of hydrogenating an olefin is that the hydrogens typically add across the double bond saturating the compound. It can be beneficial to be able to add a hydrogen to an olefin without saturating the compound.
  • the present invention provides chemical production processes and systems for hydrogenating olefins.
  • SUMMARY Chemical production processes include replacing a halogen of an unsaturated halocarbon to produce an unsaturated hydrohalocarbon.
  • Chemical production systems include a reaction zone coupled to first and second reservoirs, the first reservoir containing an unsaturated halocarbon and the second reservoir containing a hydrogenating reagent with the system being configured to expose the unsaturated halocarbon of the first reservoir to the hydrogenating agent of the second reservoir within the reaction zone.
  • the figure is an exemplary system for preparing compositions according to an embodiment. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
  • System 10 Chemical production processes and systems as described with reference to the Figure depicting a system 10 that includes a reaction zone 11 coupled to a halocarbon reservoir 12 and a hydrogenating reagent reservoir 13.
  • System 10 further includes a product recovery reservoir 14.
  • the halocarbon of reservoir 12 can be a C-2 halocarbon, and in exemplary embodiments, the halocarbon can be a heterohalocarbon.
  • the halocarbon can comprise both F and Cl, and, as another example, the halocarbon can comprise both F and Br.
  • the halocarbon can comprise both F and Br.
  • halocarbon can also be (C 2 F 3 Br,
  • the hydrogenating reagent from hydrogenating reagent reservoir 13 can be provided to reaction zone 11.
  • the hydrogenating reagent may include H, such as H 2 .
  • Reaction zone 11 can be coupled to reservoirs 13 and 14 via separate conduits with each conduit configured to control the flow of the contents of the reservoirs to reaction zone 11.
  • the conduits may be equipped with flow meters, for example.
  • Both the halocarbon and the hydrogenating reagent may be provided to the reaction zone at a mole ratio of hydrogenating reagent to halocarbon utilizing the flow meters.
  • the mole ratio of hydrogenating reagent to halocarbon may be from about 0.66 to about 11.
  • the mole ratio may be at least about 0.66 and/or the mole ratio may be less than 11.
  • the mole ratio may be at least about 1.8.
  • Reaction zone 1 1 can include a single and/or multiple reactors.
  • Reaction zone 11 may include a catalyst composition within a reactor.
  • the catalyst composition may comprise a catalyst support and/or the catalyst composition may comprise activated carbon.
  • the catalyst composition provided within reaction zone 11 may comprise one or more Pd, Cu, and/or Ni and/or the catalyst composition may comprise both Pd and Cu. Where the catalyst composition comprises both Pd and Cu, the composition may include at least about 0.6% (wt./wt.) Pd and/or the composition may be at least about 5.5% (wt./wt.) Cu. In accordance with other embodiments, the catalyst composition may comprise nickel and nickel may be at least about 5% (wt./wt.) of the composition.
  • Additional catalyst compositions can include:; Pricat CZ 29/4, AI 2 O 3 , ZnO, CuO, (Synetix (PO Box 1 , Billingham, Cleveland, TS23 1 LB, UK); 7% FeCI 3 on Takeda Carbon (Life-Environment Company, 12-10, Nlhonbashi 2-chamo Chuo-ku, Tokyo 103-8868, Japan); FeCI 3 (in-house,and/or ZnCI 2 (in-house); and those obtained from Engelhard (Chemical Catalysts Group, 554 Engelhard Drive, Seneca, SC 29678), such as,0.6%Pd/5.5%Cu and/or Ni (Engelhard, 5% Ni on 1 .5mm carbon).
  • a reactor of reaction zone 11 Prior to providing the halocarbon and/or the hydrogenating agent from reservoirs 12 and 13, respectively, a reactor of reaction zone 11 may be packed with the catalyst composition and heated to a temperature and/or exposed to a reducing agent for a sufficient time to activate the catalyst composition. Activation of the catalyst composition may be performed over a period of from about an hour to about 24 hours, for example. Typically, the catalyst composition within the reactor may be heated to from about 150 0 C to about 300 0 C during the activation. The catalyst composition may also be re-activated intermittently during the process at temperatures of from about 150°C to 400°C. The halocarbon and hydrogenating reagent may be formed into a mixture within the reactor and a portion of the mixture may be heated to at least 300 0 C.
  • the portion may be heated to from about 300 0 C and to about 400 0 C.
  • the portion may also be heated to greater than about 400 0 C, for example.
  • the temperature within the reaction zone can also be from 15O 0 C to 475°C when providing mole ratios of reducing-reagent to halocarbon of 0.1 to 10.0.
  • the reactants can reside within reaction zone 1 1 to provide contact times of from about 2 to about 20 seconds and reducing-reagent flow rates can be from 25-100cc/min while the halocarbon flow rates can be from 8-410cc/min.
  • Reservoir 14 can include an apparatus such as a 10% KOH scrubber, a Drierite tube, and/or a dry ice/ acetone trap, for example.
  • Exemplary products include, but are not limited to, unsaturated hydrohalocarbons including C-2 hydrohalocarbons.
  • the hydrohalocarbon can comprise both F and H.
  • the hydrohalocarbon can be trifluoroethylene (C 2 F 3 H, TriFE), and/or , for example.
  • system 10 can be used to replace a halogen of an unsaturated halocarbon to produce an unsaturated hydrohalocarbon.
  • Exemplary schemes 1 and 2 demonstrate exemplary reactions that can be performed utilizing system 10 of the Figure.
  • an lnconel tube can be packed with 0.6%Pd/5.5%Cu catalyst on activated carbon and maintained at 400 0 C.
  • the 'reactants can be provided to the tube at a 4.5 mole ratio of H 2 to CTFE and exposed to the catalyst for a 9.6 second contact time.
  • the conversion of CTFE to TriFE can be about 30.3% and selectivity can be 83.5% as determined by gas chromatography.
  • the lnconel tube can be packed with a Ni (Engelhard, 5% Ni on 1.5mm carbon) catalyst and maintained at 350 0 C.
  • the reactants can be provided to the tube at a 0.66 mole ratio of H 2 to CTFE and exposed to the catalyst for an 1 1.2 second contact time.
  • the conversion of CTFE to TriFE can be about 50.1 % and the selectivity can be 61.1 % as determined by gas chromatography.
  • an lnconel tube can be packed with the 0.6%Pd/5.5%Cu catalyst on activated carbon and maintained at 300 0 C.
  • the reactants can be provided to the tube at a 4.5 mole ratio of H 2 to BTFE and can be exposed to the catalyst for a 19.6 second contact time.
  • the conversion of BTFE to TriFE can be 72.3% and selectivity can be 87.0% as determined by gas chromatography.
  • an lnconel tube can be packed with the Ni (Engelhard, 5% Ni on 1.5mm carbon) catalyst and maintained at 400 0 C.
  • the reactants can be provided to the tube at a 1.8 mole ratio of H 2 to BTFE and can be exposed to the catalyst for a 12.9 second contact time.
  • the conversion of BTFE to TriFE can be 96.8% and selectivity can be 90.7% as determined by gas chromatography.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
PCT/US2005/030349 2004-08-26 2005-08-26 Chemical production processes and systems Ceased WO2006033771A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US11/661,166 US7884255B2 (en) 2004-08-26 2005-08-26 Chemical production processes and systems
EP05791273A EP1789373A4 (en) 2004-08-26 2005-08-26 CHEMICAL PRODUCTION METHODS AND SYSTEMS
JP2007530144A JP2008510831A (ja) 2004-08-26 2005-08-26 化合物生成方法及び化合物生成システム

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US60523204P 2004-08-26 2004-08-26
US60/605,232 2004-08-26

Publications (3)

Publication Number Publication Date
WO2006033771A2 true WO2006033771A2 (en) 2006-03-30
WO2006033771A3 WO2006033771A3 (en) 2006-06-29
WO2006033771A8 WO2006033771A8 (en) 2007-06-07

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PCT/US2005/030349 Ceased WO2006033771A2 (en) 2004-08-26 2005-08-26 Chemical production processes and systems
PCT/US2005/030350 Ceased WO2006026400A1 (en) 2004-08-26 2005-08-26 Chemical production processes and systems

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Country Status (6)

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US (2) US20080300432A1 (enExample)
EP (2) EP1789373A4 (enExample)
JP (2) JP2008510831A (enExample)
KR (2) KR20070057156A (enExample)
CN (3) CN101035749A (enExample)
WO (2) WO2006033771A2 (enExample)

Cited By (2)

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US20150094432A1 (en) * 2012-02-28 2015-04-02 Arkema France Method for synthesising trifluoroethylene from chlorotrifluoroethylene
EP3187477A4 (en) * 2014-08-25 2018-04-11 Asahi Glass Company, Limited Process for producing hydrofluoroolefin

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KR20070057156A (ko) 2004-08-26 2007-06-04 그레이트 레이크스 케미칼 코퍼레이션 화학적 제조 방법 및 시스템
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JP5738021B2 (ja) * 2010-08-26 2015-06-17 国立大学法人大阪大学 ヘキサフルオロ−１，３−ブタジエンの製造方法
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WO2013172337A1 (ja) * 2012-05-14 2013-11-21 国立大学法人大阪大学 ハロゲン化含フッ素（シクロ）アルケニル亜鉛化合物の製造方法
WO2016031778A1 (ja) * 2014-08-25 2016-03-03 旭硝子株式会社 ハイドロフルオロオレフィンの製造方法
CN105732301B (zh) * 2014-12-12 2018-09-07 浙江蓝天环保高科技股份有限公司 一种全氟丁二烯的制备方法
CN105713023A (zh) * 2014-12-18 2016-06-29 国立大学法人大阪大学 具有含氟(环)烯基的氟化合物的制造方法
CN104844411B (zh) * 2015-04-03 2017-08-29 北京宇极科技发展有限公司 一种合成六氟‑1,3‑丁二烯的方法
CN106673953B (zh) * 2015-11-10 2019-08-09 浙江省化工研究院有限公司 一种六氟-1,3-丁二烯的制备方法
CN110546125A (zh) * 2017-04-27 2019-12-06 关东电化工业株式会社 具有含有氢且含有氟和/或氯的丁二烯骨架的化合物的制造方法
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CN110563544A (zh) * 2019-07-25 2019-12-13 福建省杭氟电子材料有限公司 一种1,2-二溴-1,1,2-三氟乙烷的制备方法及装置
CN114206817A (zh) * 2019-08-13 2022-03-18 大金工业株式会社 1,1,2－三氟乙烯、六氟－1,3－丁二烯或1,2－二氯六氟环丁烷的制造方法
CN110590495A (zh) * 2019-08-21 2019-12-20 福建省杭氟电子材料有限公司 一种六氟丁二烯的制备方法
JP6963263B2 (ja) * 2019-12-27 2021-11-05 ダイキン工業株式会社 ハロゲン化含フッ素（シクロ）アルケニル亜鉛化合物の製造方法
CN113087589B (zh) * 2021-04-13 2022-07-19 国网湖南省电力有限公司 一种2-溴-3，3，3-三氟丙烯的制备方法
KR102701981B1 (ko) * 2021-09-23 2024-09-05 주식회사 진성이엔지 1,4-디브로모-2,3-디클로로헥사플루오로부탄 제조 방법 및 이를 이용한 헥사플루오로-1,3-부타디엔 제조 방법
CN116023398A (zh) * 2021-10-25 2023-04-28 浙江省化工研究院有限公司 一种连续或半连续化制备三氟乙烯基溴化锌的方法
CN117185898A (zh) * 2022-05-31 2023-12-08 浙江省化工研究院有限公司 一种六氟丁二烯的制备方法

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150094432A1 (en) * 2012-02-28 2015-04-02 Arkema France Method for synthesising trifluoroethylene from chlorotrifluoroethylene
US9447003B2 (en) * 2012-02-28 2016-09-20 Arkema France Method for synthesising trifluoroethylene from chlorotrifluoroethylene
EP3187477A4 (en) * 2014-08-25 2018-04-11 Asahi Glass Company, Limited Process for producing hydrofluoroolefin
US9988327B2 (en) 2014-08-25 2018-06-05 Asahi Glass Company, Limited Process for producing hydrofluoroolefin
US10781151B2 (en) 2014-08-25 2020-09-22 AGC Inc. Process for producing hydrofluoroolefin

Also Published As

Publication number Publication date
JP2008510831A (ja) 2008-04-10
US20080300432A1 (en) 2008-12-04
CN102086144A (zh) 2011-06-08
CN101035749A (zh) 2007-09-12
CN101031529B (zh) 2011-06-22
CN101031529A (zh) 2007-09-05
JP4942655B2 (ja) 2012-05-30
EP1789373A2 (en) 2007-05-30
JP2008510832A (ja) 2008-04-10
WO2006033771A3 (en) 2006-06-29
EP1789373A4 (en) 2009-01-21
WO2006033771A8 (en) 2007-06-07
KR20070057155A (ko) 2007-06-04
KR20070057156A (ko) 2007-06-04
EP1781583A4 (en) 2009-01-21
US20070299287A1 (en) 2007-12-27
EP1781583A1 (en) 2007-05-09
US7884255B2 (en) 2011-02-08
WO2006026400A1 (en) 2006-03-09

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