HU215936B - Oldószer nélküli eljárás 2,6-difluor-benzonitril előállítására - Google Patents
Oldószer nélküli eljárás 2,6-difluor-benzonitril előállítására Download PDFInfo
- Publication number
- HU215936B HU215936B HU9701844A HU9701844A HU215936B HU 215936 B HU215936 B HU 215936B HU 9701844 A HU9701844 A HU 9701844A HU 9701844 A HU9701844 A HU 9701844A HU 215936 B HU215936 B HU 215936B
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- Hungary
- Prior art keywords
- mixture
- catalyst
- dfbn
- reaction
- weight
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 49
- 230000008569 process Effects 0.000 title claims abstract description 38
- BNBRIFIJRKJGEI-UHFFFAOYSA-N 2,6-difluorobenzonitrile Chemical compound FC1=CC=CC(F)=C1C#N BNBRIFIJRKJGEI-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 99
- 239000000203 mixture Substances 0.000 claims abstract description 57
- 239000011269 tar Substances 0.000 claims abstract description 47
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000002904 solvent Substances 0.000 claims abstract description 24
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229920000570 polyether Polymers 0.000 claims abstract description 17
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 8
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 7
- 239000002739 cryptand Substances 0.000 claims abstract description 5
- 238000000926 separation method Methods 0.000 claims abstract description 5
- NLMDJJTUQPXZFG-UHFFFAOYSA-N 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane Chemical compound C1COCCOCCNCCOCCOCCN1 NLMDJJTUQPXZFG-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000011541 reaction mixture Substances 0.000 claims description 31
- 239000011698 potassium fluoride Substances 0.000 claims description 29
- 229910001512 metal fluoride Inorganic materials 0.000 claims description 27
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 23
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical group [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 20
- XPTAYRHLHAFUOS-UHFFFAOYSA-N 2-chloro-6-fluorobenzonitrile Chemical compound FC1=CC=CC(Cl)=C1C#N XPTAYRHLHAFUOS-UHFFFAOYSA-N 0.000 claims description 13
- 235000003270 potassium fluoride Nutrition 0.000 claims description 10
- 150000003983 crown ethers Chemical group 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 150000008359 benzonitriles Chemical class 0.000 claims description 7
- 150000004714 phosphonium salts Chemical class 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052796 boron Inorganic materials 0.000 abstract 1
- IIRVGTWONXBBAW-UHFFFAOYSA-M disodium;dioxido(oxo)phosphanium Chemical class [Na+].[Na+].[O-][P+]([O-])=O IIRVGTWONXBBAW-UHFFFAOYSA-M 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- KGKGSIUWJCAFPX-UHFFFAOYSA-N 2,6-dichlorothiobenzamide Chemical compound NC(=S)C1=C(Cl)C=CC=C1Cl KGKGSIUWJCAFPX-UHFFFAOYSA-N 0.000 description 59
- 239000000047 product Substances 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000004821 distillation Methods 0.000 description 26
- 239000012074 organic phase Substances 0.000 description 19
- 230000035484 reaction time Effects 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000005292 vacuum distillation Methods 0.000 description 15
- -1 18-crown-6 ethers Chemical class 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 238000001256 steam distillation Methods 0.000 description 13
- 238000011084 recovery Methods 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000007710 freezing Methods 0.000 description 6
- 230000008014 freezing Effects 0.000 description 6
- 238000004811 liquid chromatography Methods 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 230000009466 transformation Effects 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000005520 cutting process Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000001987 diarylethers Chemical class 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- AHLATJUETSFVIM-UHFFFAOYSA-M rubidium fluoride Chemical compound [F-].[Rb+] AHLATJUETSFVIM-UHFFFAOYSA-M 0.000 description 4
- XQQZRZQVBFHBHL-UHFFFAOYSA-N 12-crown-4 Chemical compound C1COCCOCCOCCO1 XQQZRZQVBFHBHL-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 229910001510 metal chloride Inorganic materials 0.000 description 3
- 239000005416 organic matter Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- DYGJZCCUSXSGBE-UHFFFAOYSA-N 1,3,5-trinitro-2,4-bis(2,4,6-trinitrophenyl)benzene Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(C=2C(=CC(=CC=2[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O)=C1[N+]([O-])=O DYGJZCCUSXSGBE-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- VEBJYBIQIYFEFN-UHFFFAOYSA-N 2-[2-[2-[2-[2-(4-octylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCO)C=C1 VEBJYBIQIYFEFN-UHFFFAOYSA-N 0.000 description 2
- JYCQQPHGFMYQCF-UHFFFAOYSA-N 4-tert-Octylphenol monoethoxylate Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCO)C=C1 JYCQQPHGFMYQCF-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CXRFDZFCGOPDTD-UHFFFAOYSA-M Cetrimide Chemical compound [Br-].CCCCCCCCCCCCCC[N+](C)(C)C CXRFDZFCGOPDTD-UHFFFAOYSA-M 0.000 description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- 229910021593 Copper(I) fluoride Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910000934 Monel 400 Inorganic materials 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- WPMWEFXCIYCJSA-UHFFFAOYSA-N Tetraethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCO WPMWEFXCIYCJSA-UHFFFAOYSA-N 0.000 description 2
- 229910001618 alkaline earth metal fluoride Inorganic materials 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
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 150000003842 bromide salts Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- OANFWJQPUHQWDL-UHFFFAOYSA-N copper iron manganese nickel Chemical compound [Mn].[Fe].[Ni].[Cu] OANFWJQPUHQWDL-UHFFFAOYSA-N 0.000 description 2
- BMRUOURRLCCWHB-UHFFFAOYSA-M copper(i) fluoride Chemical compound [Cu]F BMRUOURRLCCWHB-UHFFFAOYSA-M 0.000 description 2
- 239000002633 crown compound Substances 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 150000004673 fluoride salts Chemical class 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 150000004820 halides Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- MOYSMPXSEXYEJV-UHFFFAOYSA-M naphthalen-1-ylmethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC2=CC=CC=C2C=1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 MOYSMPXSEXYEJV-UHFFFAOYSA-M 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- 238000000643 oven drying Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- SPALIFXDWQTXKS-UHFFFAOYSA-M tetrapentylazanium;bromide Chemical compound [Br-].CCCCC[N+](CCCCC)(CCCCC)CCCCC SPALIFXDWQTXKS-UHFFFAOYSA-M 0.000 description 2
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 2
- MQAYPFVXSPHGJM-UHFFFAOYSA-M trimethyl(phenyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC=C1 MQAYPFVXSPHGJM-UHFFFAOYSA-M 0.000 description 2
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- KMHNBWHLNJDFPF-UHFFFAOYSA-M (3-nitrophenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].[O-][N+](=O)C1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 KMHNBWHLNJDFPF-UHFFFAOYSA-M 0.000 description 1
- WRXNAQRUFGEKSK-UHFFFAOYSA-M (4-nitrophenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].C1=CC([N+](=O)[O-])=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WRXNAQRUFGEKSK-UHFFFAOYSA-M 0.000 description 1
- AJDONJVWDSZZQF-UHFFFAOYSA-N 1-(2,4,4-trimethylpentan-2-yl)-4-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]benzene Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OC1=CC=C(C(C)(C)CC(C)(C)C)C=C1 AJDONJVWDSZZQF-UHFFFAOYSA-N 0.000 description 1
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
- FDXQLPHYJKXLSO-UHFFFAOYSA-N 1-methoxy-2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethane Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCOC FDXQLPHYJKXLSO-UHFFFAOYSA-N 0.000 description 1
- BXYWKXBAMJYTKP-UHFFFAOYSA-N 2-[2-[2-[2-(3-sulfanylpropanoyloxy)ethoxy]ethoxy]ethoxy]ethyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCCOCCOCCOCCOC(=O)CCS BXYWKXBAMJYTKP-UHFFFAOYSA-N 0.000 description 1
- SLAONPBUWDUSSO-UHFFFAOYSA-N 2-[2-[2-[2-(4-methylphenyl)sulfonyloxyethoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCOCCOCCOCCOS(=O)(=O)C1=CC=C(C)C=C1 SLAONPBUWDUSSO-UHFFFAOYSA-N 0.000 description 1
- DWHIUNMOTRUVPG-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCO DWHIUNMOTRUVPG-UHFFFAOYSA-N 0.000 description 1
- VJYAJQFKKLYARJ-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 VJYAJQFKKLYARJ-UHFFFAOYSA-N 0.000 description 1
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002562 Polyethylene Glycol 3350 Polymers 0.000 description 1
- 229920002571 Polyethylene Glycol 4500 Polymers 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
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- 238000010936 aqueous wash Methods 0.000 description 1
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- 150000003841 chloride salts Chemical class 0.000 description 1
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- 150000001868 cobalt Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- 235000021463 dry cake Nutrition 0.000 description 1
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- 159000000014 iron salts Chemical class 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229940050929 polyethylene glycol 3350 Drugs 0.000 description 1
- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
- 229940057071 polyethylene glycol 4500 Drugs 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 238000012207 quantitative assay Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 239000001394 sodium malate Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/365,726 US5502235A (en) | 1994-12-28 | 1994-12-28 | Solventless process for making 2,6 difluorobenzonitrile |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT77239A HUT77239A (hu) | 1998-03-02 |
| HU215936B true HU215936B (hu) | 1999-03-29 |
Family
ID=23440092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9701844A HU215936B (hu) | 1994-12-28 | 1995-11-17 | Oldószer nélküli eljárás 2,6-difluor-benzonitril előállítására |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5502235A (OSRAM) |
| EP (1) | EP0800506B1 (OSRAM) |
| JP (1) | JPH10511941A (OSRAM) |
| CN (1) | CN1174546A (OSRAM) |
| AR (1) | AR000556A1 (OSRAM) |
| AT (1) | ATE187959T1 (OSRAM) |
| AU (1) | AU702641B2 (OSRAM) |
| BR (1) | BR9510428A (OSRAM) |
| CA (1) | CA2209141A1 (OSRAM) |
| DE (1) | DE69514122T2 (OSRAM) |
| DK (1) | DK0800506T3 (OSRAM) |
| ES (1) | ES2139951T3 (OSRAM) |
| FI (1) | FI972742A7 (OSRAM) |
| HU (1) | HU215936B (OSRAM) |
| IL (1) | IL116634A (OSRAM) |
| TW (1) | TW307748B (OSRAM) |
| WO (1) | WO1996020168A1 (OSRAM) |
| ZA (1) | ZA9510902B (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3840261B2 (ja) * | 1995-06-20 | 2006-11-01 | 日本曹達株式会社 | ２，３−ジハロゲノ−６−トリフルオロメチルベンゼン誘導体およびその製造方法 |
| DE19702282C2 (de) * | 1997-01-23 | 1998-11-19 | Hoechst Ag | Katalysator für Halex-Reaktionen |
| CN100545133C (zh) * | 2001-05-17 | 2009-09-30 | 罗狄亚化学公司 | 离子性质的组合物作为取代试剂的用途,由氟化试剂构成的组合物及其使用方法 |
| DE10227223A1 (de) * | 2002-06-18 | 2004-01-08 | Kühlein, Klaus, Prof.Dr. | Verfahren zur Herstellung substituierter organischer Verbindungen und Verwendung von Katalysatoren für Substitutionsreaktionen |
| CN103044388B (zh) * | 2011-10-17 | 2015-04-15 | 张家港市国泰华荣化工新材料有限公司 | 一种3,4—二氟环丁砜的制备方法 |
| CN104387289B (zh) * | 2014-10-30 | 2017-09-01 | 天津河清化学工业有限公司 | 二氟苯腈生产中降低催化剂用量的方法 |
| CN112939782B (zh) * | 2019-12-11 | 2022-09-30 | 兰州康鹏威耳化工有限公司 | 一种含氟芳基化合物的制备方法 |
| CN113024414A (zh) * | 2021-03-23 | 2021-06-25 | 江苏合泰新材料科技有限公司 | 一种高效合成含氟化合物的方法 |
| CN119565653A (zh) * | 2024-12-05 | 2025-03-07 | 石河子大学 | 一种氮掺杂碳负载铁催化剂及其在催化合成芳香腈中的应用 |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB995927A (en) * | 1962-10-23 | 1965-06-23 | Imp Smelting Corp Ltd | Fluorination of perhalo compounds |
| NL302228A (OSRAM) * | 1962-12-20 | |||
| NL129620C (OSRAM) * | 1963-04-01 | |||
| US4051168A (en) * | 1976-05-12 | 1977-09-27 | E. I. Du Pont De Nemours And Company | Fluorination process |
| US4229365A (en) * | 1977-05-28 | 1980-10-21 | Basf Aktiengesellschaft | Manufacture of substituted fluorobenzenes |
| DE2803259A1 (de) * | 1978-01-26 | 1979-08-02 | Basf Ag | Verfahren zur herstellung von fluorbenzolen |
| DE2902877C2 (de) * | 1978-01-28 | 1983-05-05 | I.S.C. Chemicals Ltd., London | Verfahren zur Herstellung eines Fluorbenzomononitrils |
| DE2938939A1 (de) * | 1978-10-05 | 1980-04-17 | Boots Co Ltd | Verfahren zur herstellung von fluornitrobenzolen |
| US4174349A (en) * | 1978-10-30 | 1979-11-13 | Allied Chemical Corporation | Preparation of fluoroorganic compounds with calcium fluoride |
| FR2490634A1 (fr) * | 1980-09-25 | 1982-03-26 | Rhone Poulenc Ind | Procede de preparation de fluorobenzonitriles |
| JPS57197226A (en) * | 1981-05-30 | 1982-12-03 | Dainippon Ink & Chem Inc | Preparation of aromatic fluorine compound |
| EP0073372B1 (en) * | 1981-08-31 | 1984-08-01 | Ishihara Sangyo Kaisha, Ltd. | Process for producing 2,6-difluorobenzonitrile |
| DE3478681D1 (en) * | 1983-02-18 | 1989-07-20 | Nippon Catalytic Chem Ind | Organic fluorine compounds |
| JPS604159A (ja) * | 1983-06-23 | 1985-01-10 | Ishihara Sangyo Kaisha Ltd | フルオロベンゾニトリル系化合物の製造方法 |
| US4704483A (en) * | 1984-04-27 | 1987-11-03 | Occidental Chemical Corporation | 3,4-difluoro-5-nitrobenzotrifluoride and preparation of fluoro-nitro-benzotrifluorides |
| US4952719A (en) * | 1984-10-15 | 1990-08-28 | Occidental Chemical Corporation | Process for the preparation of halo aromatic compounds |
| GB8500180D0 (en) * | 1985-01-04 | 1985-02-13 | Ici Plc | Chemical process |
| US4680406A (en) * | 1985-10-15 | 1987-07-14 | The Dow Chemical Company | Process for fluorinating halogenated organo-compounds |
| JPS62114939A (ja) * | 1985-11-14 | 1987-05-26 | Sumitomo Chem Co Ltd | フルオロベンゼン誘導体の製造法 |
| US4642398A (en) * | 1986-01-06 | 1987-02-10 | Mallinckrodt, Inc. | Preparation of fluoronitrobenzene compounds in dispersion of potassium fluoride |
| US4849552A (en) * | 1986-01-06 | 1989-07-18 | Mallinckrodt, Inc. | Preparation of fluoroaromatic compounds in dispersion of potassium fluoride |
| JPS63502276A (ja) * | 1986-01-06 | 1988-09-01 | マリンクロッド・インコ−ポレイテッド | 相間移動触媒 |
| JPS63502182A (ja) * | 1986-01-06 | 1988-08-25 | マリンクロッド・インコ−ポレイテッド | 枝分れ鎖アルキルピリジニウム塩を用いるフルオロ芳香族化合物の接触製造方法 |
| DE3642326A1 (de) * | 1986-12-11 | 1988-06-23 | Bayer Ag | Verfahren zur gewinnung von substituierten fluorbenzolen |
| US4973772A (en) * | 1987-02-07 | 1990-11-27 | Mallinckrodt, Inc. | Catalytic method for producing fluoroarmatic compounds using substituted pyridinium salts |
| JP2577567B2 (ja) * | 1987-07-07 | 1997-02-05 | イハラケミカル工業株式会社 | 芳香族フッ素化合物の製造方法 |
| DE3827436A1 (de) * | 1988-08-12 | 1990-02-15 | Bayer Ag | Verfahren zum einfuehren von fluoratomen an aromatische kerne durch nucleophilen austausch |
| KR930701385A (ko) * | 1990-06-25 | 1993-06-11 | 마이어, 마르쿠아르트 | 클로로플루오로니트로벤젠 및 디플루오로니트로벤젠의 제조방법 |
| EP0635486B1 (de) * | 1993-07-21 | 1998-12-09 | Clariant GmbH | Verfahren zur Herstellung von Fluorbenzonitrilen |
-
1994
- 1994-12-28 US US08/365,726 patent/US5502235A/en not_active Expired - Fee Related
-
1995
- 1995-11-17 DE DE69514122T patent/DE69514122T2/de not_active Expired - Fee Related
- 1995-11-17 AT AT95940030T patent/ATE187959T1/de not_active IP Right Cessation
- 1995-11-17 CA CA002209141A patent/CA2209141A1/en not_active Abandoned
- 1995-11-17 BR BR9510428A patent/BR9510428A/pt not_active Application Discontinuation
- 1995-11-17 WO PCT/US1995/014971 patent/WO1996020168A1/en not_active Ceased
- 1995-11-17 EP EP95940030A patent/EP0800506B1/en not_active Expired - Lifetime
- 1995-11-17 ES ES95940030T patent/ES2139951T3/es not_active Expired - Lifetime
- 1995-11-17 CN CN95197478A patent/CN1174546A/zh active Pending
- 1995-11-17 HU HU9701844A patent/HU215936B/hu not_active IP Right Cessation
- 1995-11-17 FI FI972742A patent/FI972742A7/fi unknown
- 1995-11-17 JP JP8520445A patent/JPH10511941A/ja not_active Ceased
- 1995-11-17 DK DK95940030T patent/DK0800506T3/da active
- 1995-11-17 AU AU41645/96A patent/AU702641B2/en not_active Ceased
- 1995-11-28 TW TW084112671A patent/TW307748B/zh active
- 1995-12-21 ZA ZA9510902A patent/ZA9510902B/xx unknown
- 1995-12-27 AR ARP950100773A patent/AR000556A1/es unknown
- 1995-12-31 IL IL11663495A patent/IL116634A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| TW307748B (OSRAM) | 1997-06-11 |
| WO1996020168A1 (en) | 1996-07-04 |
| CA2209141A1 (en) | 1996-07-04 |
| EP0800506B1 (en) | 1999-12-22 |
| ZA9510902B (en) | 1997-06-23 |
| AR000556A1 (es) | 1997-07-10 |
| ATE187959T1 (de) | 2000-01-15 |
| EP0800506A1 (en) | 1997-10-15 |
| IL116634A0 (en) | 1996-03-31 |
| DE69514122D1 (de) | 2000-01-27 |
| US5502235A (en) | 1996-03-26 |
| AU4164596A (en) | 1996-07-19 |
| AU702641B2 (en) | 1999-02-25 |
| JPH10511941A (ja) | 1998-11-17 |
| BR9510428A (pt) | 1998-07-07 |
| FI972742L (fi) | 1997-08-27 |
| CN1174546A (zh) | 1998-02-25 |
| ES2139951T3 (es) | 2000-02-16 |
| DK0800506T3 (da) | 2000-05-15 |
| IL116634A (en) | 2003-04-10 |
| HUT77239A (hu) | 1998-03-02 |
| FI972742A7 (fi) | 1997-08-27 |
| DE69514122T2 (de) | 2000-04-20 |
| FI972742A0 (fi) | 1997-06-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DGB9 | Succession in title of applicant |
Owner name: DOW AGROSCIENCES LLC, US |
|
| HMM4 | Cancellation of final prot. due to non-payment of fee | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |