CA2827453C - Process for preparing fluorinated diols - Google Patents

Process for preparing fluorinated diols Download PDF

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Publication number
CA2827453C
CA2827453C CA2827453A CA2827453A CA2827453C CA 2827453 C CA2827453 C CA 2827453C CA 2827453 A CA2827453 A CA 2827453A CA 2827453 A CA2827453 A CA 2827453A CA 2827453 C CA2827453 C CA 2827453C
Authority
CA
Canada
Prior art keywords
process according
precursor compound
catalyst
optionally substituted
alkyl
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.)
Expired - Fee Related
Application number
CA2827453A
Other languages
English (en)
French (fr)
Other versions
CA2827453A1 (en
Inventor
Paul Mazzell, Jr.
Neville Pavri
Joel Swinson
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.)
Halocarbon Products Corp
Original Assignee
Halocarbon Products Corp
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 Halocarbon Products Corp filed Critical Halocarbon Products Corp
Publication of CA2827453A1 publication Critical patent/CA2827453A1/en
Application granted granted Critical
Publication of CA2827453C publication Critical patent/CA2827453C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44—Palladium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/34—Halogenated alcohols
    • C07C31/38—Halogenated alcohols containing only fluorine as halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA2827453A 2011-02-16 2012-02-16 Process for preparing fluorinated diols Expired - Fee Related CA2827453C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161443297P 2011-02-16 2011-02-16
US61/443,297 2011-02-16
PCT/US2012/025396 WO2012112751A1 (en) 2011-02-16 2012-02-16 Process for preparing fluorinated diols

Publications (2)

Publication Number Publication Date
CA2827453A1 CA2827453A1 (en) 2012-08-23
CA2827453C true CA2827453C (en) 2015-07-07

Family

ID=46672940

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2827453A Expired - Fee Related CA2827453C (en) 2011-02-16 2012-02-16 Process for preparing fluorinated diols

Country Status (8)

Country Link
US (1) US8729316B2 (enExample)
EP (1) EP2678303A4 (enExample)
JP (1) JP2014513053A (enExample)
KR (1) KR20130143113A (enExample)
CN (1) CN103429560B (enExample)
BR (1) BR112013021431A2 (enExample)
CA (1) CA2827453C (enExample)
WO (1) WO2012112751A1 (enExample)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6488769B2 (ja) 2014-03-18 2019-03-27 セントラル硝子株式会社 含フッ素ヒドロキシアルデヒド、含フッ素プロパンジオールおよび含フッ素アルコール単量体の製造方法
CN103980405B (zh) * 2014-05-17 2016-01-20 北京化工大学 端羟基液体氟聚合物的制备及固化方法
CN113045381B (zh) * 2019-12-26 2023-06-02 中蓝晨光化工研究设计院有限公司 一种含氟二元醇的制备方法

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3468964A (en) * 1965-08-03 1969-09-23 Du Pont Hydrogenation process
US3365504A (en) 1965-10-22 1968-01-23 Air Reduction Vapor phase production of propargyl alcohol under anhydrous conditions
US3394204A (en) 1965-10-23 1968-07-23 Blaga Aurel 2-methyl-3, 3, 3, trichloro-1, 2-propanediol and unsaturated polyesters prepared therefrom
US3440285A (en) 1966-04-01 1969-04-22 Allied Chem Aldehydes and alcohols prepared therefrom
US3662071A (en) 1966-05-17 1972-05-09 Du Pont Pharmaceutical composition comprising certain 1,3-substituted glycols
IL33233A (en) * 1968-12-27 1972-08-30 Baxter Laboratories Inc Preparation of 1,1,1,3,3,3-hexafluoropropan-2-ol
US3702872A (en) * 1970-07-27 1972-11-14 Baxter Laboratories Inc Production of hexafluoropropanol
US4336408A (en) * 1977-11-25 1982-06-22 Thiokol Corporation 2-Hydroxymethyl-1,3-propanediol preparation
JPS6041647B2 (ja) * 1980-11-11 1985-09-18 セントラル硝子株式会社 １，１，１，３，３，３−ヘキサフルオロプロパン−２−オ−ルの製法
US5166370A (en) * 1991-04-12 1992-11-24 Arco Chemical Technology, L.P. Preparation of tetrahydrofuran using a supported transition metal
AU5798199A (en) * 1998-09-04 2000-03-27 E.I. Du Pont De Nemours And Company Two-stage process for the production of 1,3-propanediol by catalytic hydrogenation of 3-hydroxypropanal
JP2004182622A (ja) * 2002-12-02 2004-07-02 Asahi Kasei Chemicals Corp １，３−プロパンジオールの製造方法
CN1475472A (zh) * 2003-06-30 2004-02-18 华东理工大学 1，3－丙二醇的制备方法
US7297811B2 (en) 2003-12-04 2007-11-20 International Business Machines Corporation Precursors to fluoroalkanol-containing olefin monomers and associated methods of synthesis and use
US7495135B2 (en) 2003-12-04 2009-02-24 International Business Machines Corporation Precursors to fluoroalkanol-containing olefin monomers, and associated methods of synthesis and use
JP4667035B2 (ja) * 2003-12-26 2011-04-06 セントラル硝子株式会社 １，１−ビス（トリフルオロメチル）−１，３−ジオール類アクリル酸系エステルの製造方法
US7067691B2 (en) 2003-12-26 2006-06-27 Central Glass Co., Ltd. Process for producing α-substituted acrylic acid esters
JP4324569B2 (ja) * 2004-01-27 2009-09-02 セントラル硝子株式会社 含フッ素２，４−ジオール類およびその誘導体の製造方法
US7205443B2 (en) 2004-01-27 2007-04-17 Central Glass Company, Limited Processes for producing fluorine-containing 2,4-diols and their derivatives
BRPI0507454B1 (pt) * 2004-02-04 2014-07-29 Halocarbon Prod Corp Purificação de 1,1,1,3,3,3-hexafluoroisopropanol
TW200909398A (en) * 2007-06-04 2009-03-01 Shell Int Research Hydrogenation process

Also Published As

Publication number Publication date
WO2012112751A1 (en) 2012-08-23
CN103429560A (zh) 2013-12-04
KR20130143113A (ko) 2013-12-30
US20130338404A1 (en) 2013-12-19
CN103429560B (zh) 2015-09-09
JP2014513053A (ja) 2014-05-29
CA2827453A1 (en) 2012-08-23
EP2678303A1 (en) 2014-01-01
EP2678303A4 (en) 2014-07-23
BR112013021431A2 (pt) 2016-10-25
US8729316B2 (en) 2014-05-20

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