HU193589B - Process for preparing fluorinated phtaloyl- and terephtaloyl compounds - Google Patents
Process for preparing fluorinated phtaloyl- and terephtaloyl compounds Download PDFInfo
- Publication number
- HU193589B HU193589B HU344184A HU344184A HU193589B HU 193589 B HU193589 B HU 193589B HU 344184 A HU344184 A HU 344184A HU 344184 A HU344184 A HU 344184A HU 193589 B HU193589 B HU 193589B
- Authority
- HU
- Hungary
- Prior art keywords
- fluoride
- mixture
- reaction
- formula
- compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims abstract description 35
- 235000003270 potassium fluoride Nutrition 0.000 claims abstract description 17
- 239000011698 potassium fluoride Substances 0.000 claims abstract description 17
- ROHSNXARKQFYRZ-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzene-1,4-dicarbonyl fluoride Chemical compound FC(=O)C1=C(F)C(F)=C(C(F)=O)C(F)=C1F ROHSNXARKQFYRZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003880 polar aprotic solvent Substances 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- -1 chlorinated benzene dicarboxylic acid halides Chemical class 0.000 claims description 12
- 239000003444 phase transfer catalyst Substances 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 4
- 150000004820 halides Chemical class 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 239000000575 pesticide Substances 0.000 abstract description 3
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 150000004673 fluoride salts Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 29
- 239000002904 solvent Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- WFNRNCNCXRGUKN-UHFFFAOYSA-N 2,3,5,6-tetrafluoroterephthalic acid Chemical compound OC(=O)C1=C(F)C(F)=C(C(O)=O)C(F)=C1F WFNRNCNCXRGUKN-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-LZFNBGRKSA-N Potassium-45 Chemical compound [45K] ZLMJMSJWJFRBEC-LZFNBGRKSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- YJIRZJAZKDWEIJ-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzene-1,4-dicarbonyl chloride Chemical compound ClC(=O)C1=C(Cl)C(Cl)=C(C(Cl)=O)C(Cl)=C1Cl YJIRZJAZKDWEIJ-UHFFFAOYSA-N 0.000 description 2
- IJNOVIFYQQIBHU-UHFFFAOYSA-N 3,4,5,6-tetrachlorobenzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(Cl)=O IJNOVIFYQQIBHU-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- HPMLGNIUXVXALD-UHFFFAOYSA-N benzoyl fluoride Chemical class FC(=O)C1=CC=CC=C1 HPMLGNIUXVXALD-UHFFFAOYSA-N 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- AAUSLOKBERXEER-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobenzoyl chloride Chemical compound ClC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl AAUSLOKBERXEER-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical group ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical group [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- JCEMPCVTIITKAC-UHFFFAOYSA-N dimethyl 2,3,5,6-tetrafluorobenzene-1,4-dicarboxylate Chemical compound COC(=O)C1=C(F)C(F)=C(C(=O)OC)C(F)=C1F JCEMPCVTIITKAC-UHFFFAOYSA-N 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838324902A GB8324902D0 (en) | 1983-09-16 | 1983-09-16 | Chemical process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT36773A HUT36773A (en) | 1985-10-28 |
| HU193589B true HU193589B (en) | 1987-10-28 |
Family
ID=10548910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU344184A HU193589B (en) | 1983-09-16 | 1984-09-12 | Process for preparing fluorinated phtaloyl- and terephtaloyl compounds |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0140482B1 (enExample) |
| JP (1) | JPS6087244A (enExample) |
| CA (1) | CA1234152A (enExample) |
| DE (1) | DE3468676D1 (enExample) |
| GB (2) | GB8324902D0 (enExample) |
| HU (1) | HU193589B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3621707A1 (de) * | 1986-06-28 | 1988-01-07 | Bayer Ag | Verfahren zur herstellung von 2,3,5,6-tetrafluorbenzoesaeure und die neuen verbindungen 2,3,5,6-tetrachlor-4-trifluormethyl-benzoylchlorid und 2,3,5,6-tetrafluor-4-trifluormethyl-benzoylfluorid |
| GB8705187D0 (en) * | 1987-03-05 | 1987-04-08 | Shell Int Research | Benzoic acid derivative |
| ES2059175T3 (es) * | 1991-04-25 | 1994-11-01 | Hoechst Ag | N-amino-3,4,5,6-tetrafluoro-ftalimidas sustituidas en n' y procedimiento para su preparacion. |
| ES2070545T3 (es) * | 1991-04-25 | 1995-06-01 | Hoechst Ag | Procedimiento para la preparacion de acido 2,3,4,5-tetrafluoro-benzoico. |
| ES2089644T3 (es) * | 1992-07-10 | 1996-10-01 | Hoechst Ag | Procedimiento para la preparacion de acido tetrafluoro-ftalico y/o anhidrido de acido tetrafluoro-ftalico. |
| JP4967613B2 (ja) * | 2005-12-06 | 2012-07-04 | 住友化学株式会社 | テトラフルオロテレフタル酸ジフルオライドの製造方法 |
| ZA200804817B (en) * | 2005-12-06 | 2009-12-30 | Sumitomo Chemical Co | Method for producing tetrafluoroterephthalic acid difluoride |
| CN101321720B (zh) | 2005-12-08 | 2012-12-26 | 住友化学株式会社 | 制备四氟对苯二甲酸二氟化物的方法 |
| JP4973143B2 (ja) * | 2005-12-08 | 2012-07-11 | 住友化学株式会社 | テトラフルオロテレフタル酸ジフルオライドの製造法 |
| JP5250997B2 (ja) * | 2006-04-27 | 2013-07-31 | 住友化学株式会社 | フッ化カリウム分散液およびそれを用いる含フッ素有機化合物の製造方法 |
| EP2471741A1 (en) * | 2006-04-27 | 2012-07-04 | Sumitomo Chemical Company, Limited | Potassium Fluoride |
| WO2008001826A1 (fr) | 2006-06-27 | 2008-01-03 | Sumitomo Chemical Company, Limited | Procédé de fabrication d'un benzènediméthanol substitué par halogène |
| CN102365254B (zh) | 2009-03-31 | 2014-08-27 | 住友化学株式会社 | 醇化合物的制造方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4174349A (en) * | 1978-10-30 | 1979-11-13 | Allied Chemical Corporation | Preparation of fluoroorganic compounds with calcium fluoride |
| DE2928987A1 (de) * | 1979-07-18 | 1981-02-12 | Bayer Ag | 4-fluor-3-brom-benzoylfluorid und verfahren zu seiner herstellung |
| CA1157884A (en) * | 1980-04-16 | 1983-11-29 | Byron R. Cotter | Process for the preparation of trifluoromethylbenzoyl halides |
| DE3140634A1 (de) * | 1981-10-13 | 1983-04-21 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von kernfluorierten benzoylfluoriden |
-
1983
- 1983-09-16 GB GB838324902A patent/GB8324902D0/en active Pending
-
1984
- 1984-07-24 EP EP19840305016 patent/EP0140482B1/en not_active Expired
- 1984-07-24 DE DE8484305016T patent/DE3468676D1/de not_active Expired
- 1984-07-24 GB GB08418835A patent/GB2146635B/en not_active Expired
- 1984-09-12 HU HU344184A patent/HU193589B/hu unknown
- 1984-09-17 JP JP19277584A patent/JPS6087244A/ja active Granted
- 1984-09-17 CA CA000463423A patent/CA1234152A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB8324902D0 (en) | 1983-10-19 |
| EP0140482A2 (en) | 1985-05-08 |
| JPS6087244A (ja) | 1985-05-16 |
| DE3468676D1 (en) | 1988-02-18 |
| GB8418835D0 (en) | 1984-08-30 |
| EP0140482B1 (en) | 1988-01-13 |
| GB2146635B (en) | 1987-05-13 |
| GB2146635A (en) | 1985-04-24 |
| HUT36773A (en) | 1985-10-28 |
| JPH0466220B2 (enExample) | 1992-10-22 |
| CA1234152A (en) | 1988-03-15 |
| EP0140482A3 (en) | 1985-06-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HPC4 | Succession in title of patentee |
Owner name: ZENECA LIMITED, GB |