CA2557973C - Preparation of carbonyl fluoride - Google Patents
Preparation of carbonyl fluoride Download PDFInfo
- Publication number
- CA2557973C CA2557973C CA2557973A CA2557973A CA2557973C CA 2557973 C CA2557973 C CA 2557973C CA 2557973 A CA2557973 A CA 2557973A CA 2557973 A CA2557973 A CA 2557973A CA 2557973 C CA2557973 C CA 2557973C
- Authority
- CA
- Canada
- Prior art keywords
- mol
- process according
- chlorine
- irradiation
- oxygen
- 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
Links
- SYNPRNNJJLRHTI-UHFFFAOYSA-N 2-(hydroxymethyl)butane-1,4-diol Chemical compound OCCC(CO)CO SYNPRNNJJLRHTI-UHFFFAOYSA-N 0.000 title abstract description 6
- 238000002360 preparation method Methods 0.000 title description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000000460 chlorine Substances 0.000 claims abstract description 27
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 27
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 239000007858 starting material Substances 0.000 claims description 10
- 239000000376 reactant Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000003595 spectral effect Effects 0.000 claims description 2
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 abstract description 40
- 230000003647 oxidation Effects 0.000 abstract description 3
- 238000007254 oxidation reaction Methods 0.000 abstract description 3
- 238000005530 etching Methods 0.000 abstract description 2
- IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical compound FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 14
- 101100328843 Dictyostelium discoideum cofB gene Proteins 0.000 description 13
- 239000007789 gas Substances 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 11
- 230000005855 radiation Effects 0.000 description 11
- 239000011521 glass Substances 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- 229910052753 mercury Inorganic materials 0.000 description 7
- 239000005388 borosilicate glass Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000005293 duran Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 238000007539 photo-oxidation reaction Methods 0.000 description 3
- OKIIEJOIXGHUKX-UHFFFAOYSA-L cadmium iodide Chemical compound [Cd+2].[I-].[I-] OKIIEJOIXGHUKX-UHFFFAOYSA-L 0.000 description 2
- 150000005826 halohydrocarbons Chemical class 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- 238000006552 photochemical reaction Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- JLOQJZDCBQOPSD-UHFFFAOYSA-N FC(F)=O.F[ClH]C(Cl)=O Chemical compound FC(F)=O.F[ClH]C(Cl)=O JLOQJZDCBQOPSD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 229940075417 cadmium iodide Drugs 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- DWRNSCDYNYYYHT-UHFFFAOYSA-K gallium(iii) iodide Chemical compound I[Ga](I)I DWRNSCDYNYYYHT-UHFFFAOYSA-K 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000005437 stratosphere Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- CMJCEVKJYRZMIA-UHFFFAOYSA-M thallium(i) iodide Chemical compound [Tl]I CMJCEVKJYRZMIA-UHFFFAOYSA-M 0.000 description 1
- 239000005436 troposphere Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/80—Phosgene
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Carbon And Carbon Compounds (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04005421.5 | 2004-03-08 | ||
| EP04005421A EP1574478A1 (de) | 2004-03-08 | 2004-03-08 | Herstellung von Carbonylfluorid |
| PCT/EP2005/001281 WO2005085129A2 (de) | 2004-03-08 | 2005-02-09 | Herstellung von carbonylfluorid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2557973A1 CA2557973A1 (en) | 2005-09-15 |
| CA2557973C true CA2557973C (en) | 2012-07-24 |
Family
ID=34814253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2557973A Expired - Fee Related CA2557973C (en) | 2004-03-08 | 2005-02-09 | Preparation of carbonyl fluoride |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7880039B2 (https=) |
| EP (2) | EP1574478A1 (https=) |
| JP (1) | JP5007220B2 (https=) |
| KR (1) | KR101300815B1 (https=) |
| CN (1) | CN1930081B (https=) |
| CA (1) | CA2557973C (https=) |
| TW (1) | TWI361795B (https=) |
| WO (1) | WO2005085129A2 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1652814A1 (de) | 2004-10-27 | 2006-05-03 | Solvay Fluor GmbH | Verfahren zur Gastrennung |
| TW200808656A (en) * | 2006-04-27 | 2008-02-16 | Solvay Fluor Gmbh | Reversible water-free process for the separation of acid-containing gas mixtures |
| EP2170789A1 (en) * | 2007-07-20 | 2010-04-07 | Solvay Fluor GmbH | Process for obtaining a purified hydrofluoroalkane |
| US8664438B2 (en) * | 2008-10-06 | 2014-03-04 | Showa Denko K.K. | Process for producing carbonyl difluoride |
| CN101735034B (zh) * | 2009-12-18 | 2013-01-16 | 杭州原正化学工程技术装备有限公司 | 一种三氟乙酰氯的制备方法 |
| UY34094A (es) | 2011-05-27 | 2013-01-03 | Novartis Ag | Derivados de la piperidina 3-espirocíclica como agonistas de receptores de la ghrelina |
| CA2867043A1 (en) | 2012-05-03 | 2013-11-07 | Novartis Ag | L-malate salt of 2,7-diaza-spiro[4.5]dec-7-yle derivatives and crystalline forms thereof as ghrelin receptor agonists |
| EP2705893A1 (en) | 2012-09-05 | 2014-03-12 | Solvay SA | Process for separating acid-containing gas mixtures |
| TWI800693B (zh) | 2018-11-15 | 2023-05-01 | 國立大學法人神戶大學 | 碳酸酯衍生物之製造方法 |
| US12234321B2 (en) | 2018-11-15 | 2025-02-25 | National University Corporation Kobe University | Method for producing polycarbonate |
| KR102875588B1 (ko) | 2019-09-05 | 2025-10-22 | 고쿠리츠다이가쿠호진 고베다이가쿠 | 할로겐화 카보닐의 제조방법 |
| WO2021045105A1 (ja) * | 2019-09-05 | 2021-03-11 | 国立大学法人神戸大学 | ハロゲン化カルボニルの製造方法 |
| WO2022172745A1 (ja) * | 2021-02-12 | 2022-08-18 | 国立大学法人神戸大学 | ハロゲン化カルボニルの製造方法 |
| JP7239953B2 (ja) * | 2021-02-12 | 2023-03-15 | 国立大学法人神戸大学 | ハロゲン化カルボニルの製造方法 |
| CN120225464A (zh) * | 2022-12-21 | 2025-06-27 | 国立大学法人神户大学 | 碳酰卤的制备方法 |
| CN121712715A (zh) * | 2023-10-12 | 2026-03-20 | 国立大学法人神户大学 | 酰卤的制造方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0310255A1 (en) | 1987-09-14 | 1989-04-05 | STAUFFER MANAGEMENT COMPANY c/o ICI AMERICAS INC. | Production of carbonyl difluoride |
| DE19650212A1 (de) * | 1996-12-04 | 1998-06-18 | Solvay Fluor & Derivate | Herstellung von Carbonsäurefluoriden |
| US6051682A (en) | 1996-12-23 | 2000-04-18 | E. I. Du Pont De Nemours And Company | Polymerization of fluoropolymers in carbon dioxide |
| WO2001034667A1 (en) | 1999-11-12 | 2001-05-17 | North Carolina State University | Continuous process for making polymers in carbon dioxide |
-
2004
- 2004-03-08 EP EP04005421A patent/EP1574478A1/de not_active Withdrawn
-
2005
- 2005-02-09 WO PCT/EP2005/001281 patent/WO2005085129A2/de not_active Ceased
- 2005-02-09 CA CA2557973A patent/CA2557973C/en not_active Expired - Fee Related
- 2005-02-09 KR KR1020067018250A patent/KR101300815B1/ko not_active Expired - Fee Related
- 2005-02-09 JP JP2007502213A patent/JP5007220B2/ja not_active Expired - Fee Related
- 2005-02-09 EP EP05707275A patent/EP1723075B8/de not_active Expired - Lifetime
- 2005-02-09 US US10/591,783 patent/US7880039B2/en not_active Expired - Fee Related
- 2005-02-09 CN CN2005800074131A patent/CN1930081B/zh not_active Expired - Fee Related
- 2005-02-25 TW TW094105759A patent/TWI361795B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US7880039B2 (en) | 2011-02-01 |
| EP1723075B1 (de) | 2012-10-17 |
| JP2007527841A (ja) | 2007-10-04 |
| CN1930081A (zh) | 2007-03-14 |
| TWI361795B (en) | 2012-04-11 |
| EP1723075B8 (de) | 2013-01-16 |
| CA2557973A1 (en) | 2005-09-15 |
| CN1930081B (zh) | 2011-12-07 |
| EP1574478A1 (de) | 2005-09-14 |
| KR20070018884A (ko) | 2007-02-14 |
| WO2005085129A3 (de) | 2006-02-02 |
| EP1723075A2 (de) | 2006-11-22 |
| TW200540108A (en) | 2005-12-16 |
| WO2005085129A2 (de) | 2005-09-15 |
| KR101300815B1 (ko) | 2013-08-26 |
| US20070197826A1 (en) | 2007-08-23 |
| JP5007220B2 (ja) | 2012-08-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20150209 |