ZA200302352B - Process for producing flourinated ester compound. - Google Patents
Process for producing flourinated ester compound. Download PDFInfo
- Publication number
- ZA200302352B ZA200302352B ZA200302352A ZA200302352A ZA200302352B ZA 200302352 B ZA200302352 B ZA 200302352B ZA 200302352 A ZA200302352 A ZA 200302352A ZA 200302352 A ZA200302352 A ZA 200302352A ZA 200302352 B ZA200302352 B ZA 200302352B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- group
- reaction
- ester
- fluorination
- Prior art date
Links
- -1 ester compound Chemical class 0.000 title claims abstract description 91
- 238000000034 method Methods 0.000 title claims description 61
- 230000008569 process Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 307
- 238000003682 fluorination reaction Methods 0.000 claims abstract description 83
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 55
- 150000001265 acyl fluorides Chemical group 0.000 claims abstract description 42
- 239000011737 fluorine Substances 0.000 claims abstract description 39
- 239000007791 liquid phase Substances 0.000 claims abstract description 38
- 239000007788 liquid Substances 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 150000002148 esters Chemical class 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 72
- 125000000962 organic group Chemical group 0.000 claims description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 32
- 125000001153 fluoro group Chemical group F* 0.000 claims description 26
- 230000032050 esterification Effects 0.000 claims description 24
- 238000005886 esterification reaction Methods 0.000 claims description 24
- 238000010494 dissociation reaction Methods 0.000 claims description 22
- 208000018459 dissociative disease Diseases 0.000 claims description 20
- 239000007795 chemical reaction product Substances 0.000 claims description 16
- 101100502522 Mus musculus Fcor gene Proteins 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract description 36
- 239000002253 acid Chemical class 0.000 abstract description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 45
- 229930195734 saturated hydrocarbon Natural products 0.000 description 41
- 125000000217 alkyl group Chemical group 0.000 description 29
- 125000005842 heteroatom Chemical group 0.000 description 29
- 239000007789 gas Substances 0.000 description 20
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 13
- 125000004430 oxygen atom Chemical group O* 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 125000004122 cyclic group Chemical group 0.000 description 11
- 239000012071 phase Substances 0.000 description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 238000000197 pyrolysis Methods 0.000 description 9
- 239000002516 radical scavenger Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 239000011261 inert gas Substances 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 5
- 101150065749 Churc1 gene Proteins 0.000 description 5
- 102100038239 Protein Churchill Human genes 0.000 description 5
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 230000026030 halogenation Effects 0.000 description 4
- 238000005658 halogenation reaction Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000011775 sodium fluoride Substances 0.000 description 4
- 235000013024 sodium fluoride Nutrition 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- COPNBMBEZMJJPT-UHFFFAOYSA-N 3,4-dichlorobutan-1-ol Chemical compound OCCC(Cl)CCl COPNBMBEZMJJPT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021583 Cobalt(III) fluoride Inorganic materials 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- IUHFWCGCSVTMPG-UHFFFAOYSA-N [C].[C] Chemical group [C].[C] IUHFWCGCSVTMPG-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000001602 bicycloalkyls Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 150000005827 chlorofluoro hydrocarbons Chemical class 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- WZJQNLGQTOCWDS-UHFFFAOYSA-K cobalt(iii) fluoride Chemical compound F[Co](F)F WZJQNLGQTOCWDS-UHFFFAOYSA-K 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000006551 perfluoro alkylene group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HJBYJZCUFFYSGA-UHFFFAOYSA-N prop-2-enoyl fluoride Chemical group FC(=O)C=C HJBYJZCUFFYSGA-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/287—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- 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
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/297—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000295141 | 2000-09-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200302352B true ZA200302352B (en) | 2004-03-26 |
Family
ID=18777613
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200302352A ZA200302352B (en) | 2000-09-27 | 2001-09-27 | Process for producing flourinated ester compound. |
Country Status (14)
Country | Link |
---|---|
US (2) | US7034179B2 (ko) |
EP (1) | EP1323703B1 (ko) |
JP (1) | JP4934940B2 (ko) |
KR (1) | KR100768026B1 (ko) |
CN (1) | CN1242979C (ko) |
AT (1) | ATE374173T1 (ko) |
AU (1) | AU2001292268A1 (ko) |
CA (1) | CA2423910C (ko) |
DE (1) | DE60130670T2 (ko) |
ES (1) | ES2294032T3 (ko) |
HK (1) | HK1053459A1 (ko) |
RU (1) | RU2268875C2 (ko) |
WO (1) | WO2002026688A1 (ko) |
ZA (1) | ZA200302352B (ko) |
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JP4802367B2 (ja) | 1999-03-23 | 2011-10-26 | 旭硝子株式会社 | 液相フッ素化による含フッ素化合物の製造方法 |
AU2001236108A1 (en) | 2000-06-02 | 2001-12-17 | Asahi Glass Company, Limited | Process for preparing unsaturated compounds by pyrolysis |
DE60130557T2 (de) | 2000-07-11 | 2008-01-31 | Asahi Glass Co., Ltd. | Verfahren zur herstellung von fluor-enthaltenden verbindungen |
CN1196666C (zh) | 2000-07-28 | 2005-04-13 | 旭硝子株式会社 | 含氟酰氟的制造方法和含氟乙烯醚的制造方法 |
ATE520642T1 (de) * | 2000-09-27 | 2011-09-15 | Asahi Glass Co Ltd | Verfahren zur herstellung einer fluorinierten polyvalenten carbonylverbindung |
KR100768026B1 (ko) | 2000-09-27 | 2007-10-18 | 아사히 가라스 가부시키가이샤 | 불소함유 에스테르 화합물의 제조방법 |
ATE470654T1 (de) | 2001-01-16 | 2010-06-15 | Asahi Glass Co Ltd | Verfahren zur herstellung von fluorierten estern, fluoriertem acylfluorid und fluorierten vinylethern |
TWI322709B (en) | 2001-12-04 | 2010-04-01 | Bp Chem Int Ltd | Oxidation process in fluidised bed reactor |
CN100500639C (zh) * | 2002-12-11 | 2009-06-17 | 旭硝子株式会社 | 氟化金刚烷衍生物 |
JP4771757B2 (ja) * | 2005-06-20 | 2011-09-14 | 富士フイルム株式会社 | 高選択的な1,2−ジクロリド化合物の製造方法 |
CN100338012C (zh) * | 2005-11-07 | 2007-09-19 | 上海泰卓科技有限公司 | 一种含氟酰氟类化合物的处理方法 |
EP2321250B1 (en) * | 2008-07-08 | 2013-07-03 | Solvay Specialty Polymers Italy S.p.A. | Process for the manufacture of fluorosurfactants |
US8563115B2 (en) * | 2008-08-12 | 2013-10-22 | Xerox Corporation | Protective coatings for solid inkjet applications |
US8191992B2 (en) * | 2008-12-15 | 2012-06-05 | Xerox Corporation | Protective coatings for solid inkjet applications |
JP6037568B2 (ja) * | 2010-11-22 | 2016-12-07 | ソルヴェイ・スペシャルティ・ポリマーズ・イタリー・エッセ・ピ・ア | パーフルオロ有機化合物の製造方法 |
US20150261914A1 (en) * | 2014-03-13 | 2015-09-17 | Genestack Limited | Apparatus and methods for analysing biochemical data |
CN104876823A (zh) * | 2015-05-05 | 2015-09-02 | 湖南晟通纳米新材料有限公司 | 可聚合全氟聚醚单体合成方法 |
US9459536B1 (en) * | 2015-06-30 | 2016-10-04 | Taiwan Semiconductor Manufacturing Company, Ltd. | Negative tone developer composition for extreme ultraviolet lithography |
CN105646177A (zh) * | 2015-12-31 | 2016-06-08 | 天津市长芦化工新材料有限公司 | 一种制备全氟聚醚羧酸的方法 |
CN111116347A (zh) * | 2019-12-30 | 2020-05-08 | 天津市长芦化工新材料有限公司 | 低hf含量的全氟聚醚羧酸及其制备方法 |
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US3900372A (en) * | 1974-09-16 | 1975-08-19 | Phillips Petroleum Co | Recycle of acyl fluoride and electrochemical fluorination of esters |
JPS5210221A (en) | 1975-07-15 | 1977-01-26 | Teijin Ltd | Process for preparation of perfluoroalkylethers containing fluorosulfo nyl group |
JPS57164991A (en) | 1981-04-02 | 1982-10-09 | Asahi Chem Ind Co Ltd | Production of (omega-fluorosulfonyl)haloaliphatic carboxylic acid fluoride |
US4526948A (en) | 1983-12-27 | 1985-07-02 | E. I. Du Pont De Nemours And Company | Fluorinated vinyl ethers, copolymers thereof, and precursors thereto |
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JP2701454B2 (ja) | 1989-05-24 | 1998-01-21 | 旭硝子株式会社 | 新規含フッ素化合物,その製造方法及び用途 |
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JP2000007593A (ja) | 1998-06-24 | 2000-01-11 | Asahi Glass Co Ltd | ペルフルオロ(n−ペンタン)の製造方法 |
JP4802367B2 (ja) | 1999-03-23 | 2011-10-26 | 旭硝子株式会社 | 液相フッ素化による含フッ素化合物の製造方法 |
JP2001139509A (ja) * | 1999-08-31 | 2001-05-22 | Asahi Glass Co Ltd | 熱分解反応による不飽和化合物の製造方法 |
WO2001016085A1 (en) | 1999-08-31 | 2001-03-08 | Asahi Glass Company, Limited | Process for producing a vic-dichloro acid fluoride |
WO2001046093A2 (en) * | 1999-12-20 | 2001-06-28 | Asahi Glass Company, Limited | Process for producing a fluoride compound |
US6255536B1 (en) | 1999-12-22 | 2001-07-03 | Dyneon Llc | Fluorine containing vinyl ethers |
WO2002010107A1 (fr) | 2000-07-31 | 2002-02-07 | Asahi Glass Company, Limited | Procede de preparation de fluorures de perfluoroacyle |
CN1240658C (zh) | 2000-08-30 | 2006-02-08 | 旭硝子株式会社 | 含氟酮的制造方法 |
KR100768026B1 (ko) | 2000-09-27 | 2007-10-18 | 아사히 가라스 가부시키가이샤 | 불소함유 에스테르 화합물의 제조방법 |
EP1346980B1 (en) | 2000-11-28 | 2011-05-18 | Asahi Glass Company Ltd. | Process for producing fluorosulfonyl fluoride compound |
ATE470654T1 (de) | 2001-01-16 | 2010-06-15 | Asahi Glass Co Ltd | Verfahren zur herstellung von fluorierten estern, fluoriertem acylfluorid und fluorierten vinylethern |
-
2001
- 2001-09-27 KR KR1020037004379A patent/KR100768026B1/ko active IP Right Grant
- 2001-09-27 JP JP2002531075A patent/JP4934940B2/ja not_active Expired - Lifetime
- 2001-09-27 ES ES01972529T patent/ES2294032T3/es not_active Expired - Lifetime
- 2001-09-27 ZA ZA200302352A patent/ZA200302352B/en unknown
- 2001-09-27 RU RU2003112231/04A patent/RU2268875C2/ru not_active IP Right Cessation
- 2001-09-27 AU AU2001292268A patent/AU2001292268A1/en not_active Abandoned
- 2001-09-27 CN CNB018162967A patent/CN1242979C/zh not_active Expired - Fee Related
- 2001-09-27 DE DE60130670T patent/DE60130670T2/de not_active Expired - Lifetime
- 2001-09-27 AT AT01972529T patent/ATE374173T1/de not_active IP Right Cessation
- 2001-09-27 CA CA2423910A patent/CA2423910C/en not_active Expired - Fee Related
- 2001-09-27 WO PCT/JP2001/008433 patent/WO2002026688A1/ja active IP Right Grant
- 2001-09-27 EP EP01972529A patent/EP1323703B1/en not_active Expired - Lifetime
-
2003
- 2003-03-27 US US10/397,521 patent/US7034179B2/en not_active Expired - Lifetime
- 2003-08-11 HK HK03105731A patent/HK1053459A1/xx not_active IP Right Cessation
-
2005
- 2005-04-14 US US11/105,518 patent/US7161025B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
US7161025B2 (en) | 2007-01-09 |
CA2423910C (en) | 2010-07-27 |
EP1323703B1 (en) | 2007-09-26 |
DE60130670T2 (de) | 2008-07-17 |
EP1323703A1 (en) | 2003-07-02 |
DE60130670D1 (de) | 2007-11-08 |
ATE374173T1 (de) | 2007-10-15 |
AU2001292268A1 (en) | 2002-04-08 |
JPWO2002026688A1 (ja) | 2004-02-05 |
US20030216595A1 (en) | 2003-11-20 |
ES2294032T3 (es) | 2008-04-01 |
KR20030043973A (ko) | 2003-06-02 |
CN1242979C (zh) | 2006-02-22 |
JP4934940B2 (ja) | 2012-05-23 |
US20050192456A1 (en) | 2005-09-01 |
RU2268875C2 (ru) | 2006-01-27 |
US7034179B2 (en) | 2006-04-25 |
CA2423910A1 (en) | 2003-03-26 |
CN1466563A (zh) | 2004-01-07 |
KR100768026B1 (ko) | 2007-10-18 |
WO2002026688A1 (fr) | 2002-04-04 |
EP1323703A4 (en) | 2005-11-23 |
HK1053459A1 (en) | 2003-10-24 |
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