KR20130143113A - 플루오르화된 디올의 제조 방법 - Google Patents
플루오르화된 디올의 제조 방법 Download PDFInfo
- Publication number
- KR20130143113A KR20130143113A KR1020137024350A KR20137024350A KR20130143113A KR 20130143113 A KR20130143113 A KR 20130143113A KR 1020137024350 A KR1020137024350 A KR 1020137024350A KR 20137024350 A KR20137024350 A KR 20137024350A KR 20130143113 A KR20130143113 A KR 20130143113A
- Authority
- KR
- South Korea
- Prior art keywords
- precursor compound
- catalyst
- compound
- alkyl
- hydrogen
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 150000002009 diols Chemical class 0.000 title description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000003054 catalyst Substances 0.000 claims abstract description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- -1 diol compounds Chemical class 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012808 vapor phase Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000002243 precursor Substances 0.000 claims description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000010924 continuous production Methods 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 3
- 238000010923 batch production Methods 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical class [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- UMUCWGONGYAOJJ-UHFFFAOYSA-N 1-chloro-1,1-difluoropropan-2-one Chemical compound CC(=O)C(F)(F)Cl UMUCWGONGYAOJJ-UHFFFAOYSA-N 0.000 description 1
- FKCDFZGOYGIBAZ-UHFFFAOYSA-N 4,4,4-trifluoro-3-hydroxy-3-(trifluoromethyl)butanal Chemical compound FC(F)(F)C(C(F)(F)F)(O)CC=O FKCDFZGOYGIBAZ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- CJVLCYKWJXBRPK-UHFFFAOYSA-N CCCC(O)O.OCCC(O)(C(F)(F)F)C(F)(F)F Chemical compound CCCC(O)O.OCCC(O)(C(F)(F)F)C(F)(F)F CJVLCYKWJXBRPK-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 239000010814 metallic waste Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
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
-
- 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
- C07C29/14—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)
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 (1)
| Publication Number | Publication Date |
|---|---|
| KR20130143113A true KR20130143113A (ko) | 2013-12-30 |
Family
ID=46672940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020137024350A Ceased KR20130143113A (ko) | 2011-02-16 | 2012-02-16 | 플루오르화된 디올의 제조 방법 |
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)
| 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)
| 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 |
-
2012
- 2012-02-16 BR BR112013021431A patent/BR112013021431A2/pt not_active IP Right Cessation
- 2012-02-16 US US13/985,588 patent/US8729316B2/en not_active Expired - Fee Related
- 2012-02-16 WO PCT/US2012/025396 patent/WO2012112751A1/en not_active Ceased
- 2012-02-16 JP JP2013554595A patent/JP2014513053A/ja active Pending
- 2012-02-16 KR KR1020137024350A patent/KR20130143113A/ko not_active Ceased
- 2012-02-16 CN CN201280013934.8A patent/CN103429560B/zh not_active Expired - Fee Related
- 2012-02-16 CA CA2827453A patent/CA2827453C/en not_active Expired - Fee Related
- 2012-02-16 EP EP12747486.4A patent/EP2678303A4/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO2012112751A1 (en) | 2012-08-23 |
| CA2827453C (en) | 2015-07-07 |
| CN103429560A (zh) | 2013-12-04 |
| 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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Patent event date: 20130913 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20131031 Comment text: Request for Examination of Application |
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Comment text: Notification of reason for refusal Patent event date: 20150330 Patent event code: PE09021S01D |
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