JPH10511941A - ２，６−ジフルオロベンゾニトリルを無溶媒で製造する方法 - Google Patents
２，６−ジフルオロベンゾニトリルを無溶媒で製造する方法Info
- Publication number
- JPH10511941A JPH10511941A JP8520445A JP52044596A JPH10511941A JP H10511941 A JPH10511941 A JP H10511941A JP 8520445 A JP8520445 A JP 8520445A JP 52044596 A JP52044596 A JP 52044596A JP H10511941 A JPH10511941 A JP H10511941A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- crown
- fluoride
- mixture
- reaction
- 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
- 239000002904 solvent Substances 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 21
- BNBRIFIJRKJGEI-UHFFFAOYSA-N 2,6-difluorobenzonitrile Chemical compound FC1=CC=CC(F)=C1C#N BNBRIFIJRKJGEI-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 100
- 239000000203 mixture Substances 0.000 claims abstract description 81
- 238000006243 chemical reaction Methods 0.000 claims abstract description 69
- 229910001512 metal fluoride Inorganic materials 0.000 claims abstract description 30
- 229920000570 polyether Polymers 0.000 claims abstract description 19
- 239000000126 substance Substances 0.000 claims abstract description 17
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 14
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 13
- 150000004714 phosphonium salts Chemical class 0.000 claims abstract description 13
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 11
- 239000002739 cryptand Substances 0.000 claims abstract description 7
- NLMDJJTUQPXZFG-UHFFFAOYSA-N 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane Chemical compound C1COCCOCCNCCOCCOCCN1 NLMDJJTUQPXZFG-UHFFFAOYSA-N 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims description 96
- 239000011698 potassium fluoride Substances 0.000 claims description 36
- 239000011269 tar Substances 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- -1 18-crown-6 crown ether Chemical class 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- 150000003983 crown ethers Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 235000003270 potassium fluoride Nutrition 0.000 claims description 14
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims description 12
- AHLATJUETSFVIM-UHFFFAOYSA-M rubidium fluoride Chemical compound [F-].[Rb+] AHLATJUETSFVIM-UHFFFAOYSA-M 0.000 claims description 12
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical group [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 10
- XPTAYRHLHAFUOS-UHFFFAOYSA-N 2-chloro-6-fluorobenzonitrile Chemical compound FC1=CC=CC(Cl)=C1C#N XPTAYRHLHAFUOS-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 claims description 8
- 229910021593 Copper(I) fluoride Inorganic materials 0.000 claims description 6
- 235000013024 sodium fluoride Nutrition 0.000 claims description 6
- 239000011775 sodium fluoride Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 4
- 229910001515 alkali metal fluoride Inorganic materials 0.000 claims description 4
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 claims description 4
- 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 claims description 4
- MOYSMPXSEXYEJV-UHFFFAOYSA-M naphthalen-1-ylmethyl(triphenyl)phosphanium;chloride Chemical group [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 claims description 4
- 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 claims description 2
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 claims 5
- GDHXJNRAJRCGMX-UHFFFAOYSA-N 2-fluorobenzonitrile Chemical compound FC1=CC=CC=C1C#N GDHXJNRAJRCGMX-UHFFFAOYSA-N 0.000 claims 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 3
- BBGKDYHZQOSNMU-UHFFFAOYSA-N dicyclohexano-18-crown-6 Chemical compound O1CCOCCOC2CCCCC2OCCOCCOC2CCCCC21 BBGKDYHZQOSNMU-UHFFFAOYSA-N 0.000 claims 3
- 229910052708 sodium Inorganic materials 0.000 claims 3
- 239000011734 sodium Substances 0.000 claims 3
- MQAYPFVXSPHGJM-UHFFFAOYSA-M trimethyl(phenyl)azanium;chloride Chemical group [Cl-].C[N+](C)(C)C1=CC=CC=C1 MQAYPFVXSPHGJM-UHFFFAOYSA-M 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 241000234435 Lilium Species 0.000 claims 2
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 claims 2
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 150000008359 benzonitriles Chemical class 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- KGKGSIUWJCAFPX-UHFFFAOYSA-N 2,6-dichlorothiobenzamide Chemical compound NC(=S)C1=C(Cl)C=CC=C1Cl KGKGSIUWJCAFPX-UHFFFAOYSA-N 0.000 description 52
- 239000000047 product Substances 0.000 description 39
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 30
- 238000004821 distillation Methods 0.000 description 23
- 230000035484 reaction time Effects 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000007795 chemical reaction product Substances 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- 238000005292 vacuum distillation Methods 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000001914 filtration Methods 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 238000011084 recovery Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 238000001256 steam distillation Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 230000004907 flux Effects 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 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 6
- 238000000605 extraction Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000003990 capacitor Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000012216 screening Methods 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000010908 decantation Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000004811 liquid chromatography Methods 0.000 description 4
- 239000005416 organic matter Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 150000003841 chloride salts Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HMSWAIKSFDFLKN-UHFFFAOYSA-N Hexacosane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCC HMSWAIKSFDFLKN-UHFFFAOYSA-N 0.000 description 2
- 229910000934 Monel 400 Inorganic materials 0.000 description 2
- 239000004677 Nylon Substances 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
- 150000003842 bromide salts Chemical class 0.000 description 2
- 150000008422 chlorobenzenes Chemical class 0.000 description 2
- OANFWJQPUHQWDL-UHFFFAOYSA-N copper iron manganese nickel Chemical compound [Mn].[Fe].[Ni].[Cu] OANFWJQPUHQWDL-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000004673 fluoride salts Chemical class 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910001510 metal chloride Inorganic materials 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 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
- IKQCKKLYNALQBF-UHFFFAOYSA-N 1,4,7,10,13,16-hexaoxacyclooctadeca-2,5,8,11,14,17-hexaene Chemical compound O1C=COC=COC=COC=COC=COC=C1 IKQCKKLYNALQBF-UHFFFAOYSA-N 0.000 description 1
- CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-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
- XQQZRZQVBFHBHL-UHFFFAOYSA-N 12-crown-4 Chemical compound C1COCCOCCOCCO1 XQQZRZQVBFHBHL-UHFFFAOYSA-N 0.000 description 1
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- CXRFDZFCGOPDTD-UHFFFAOYSA-M Cetrimide Chemical compound [Br-].CCCCCCCCCCCCCC[N+](C)(C)C CXRFDZFCGOPDTD-UHFFFAOYSA-M 0.000 description 1
- 206010053567 Coagulopathies Diseases 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 240000000018 Gnetum gnemon Species 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- 241000638935 Senecio crassissimus Species 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- WPMWEFXCIYCJSA-UHFFFAOYSA-N Tetraethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCO WPMWEFXCIYCJSA-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 150000001462 antimony Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000013527 bean curd Nutrition 0.000 description 1
- 150000005347 biaryls Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 230000035602 clotting Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000002633 crown compound 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
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000012768 molten material Substances 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 230000000737 periodic effect Effects 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
- 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
- 238000011027 product recovery Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001394 sodium malate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- SPALIFXDWQTXKS-UHFFFAOYSA-M tetrapentylazanium;bromide Chemical compound [Br-].CCCCC[N+](CCCCC)(CCCCC)CCCCC SPALIFXDWQTXKS-UHFFFAOYSA-M 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 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)
- Catalysts (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| 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 |
| US08/365,726 | 1994-12-28 | ||
| PCT/US1995/014971 WO1996020168A1 (en) | 1994-12-28 | 1995-11-17 | Solventless process for making 2,6-difluorobenzonitrile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH10511941A true JPH10511941A (ja) | 1998-11-17 |
Family
ID=23440092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8520445A Ceased JPH10511941A (ja) | 1994-12-28 | 1995-11-17 | ２，６−ジフルオロベンゾニトリルを無溶媒で製造する方法 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5502235A (enExample) |
| EP (1) | EP0800506B1 (enExample) |
| JP (1) | JPH10511941A (enExample) |
| CN (1) | CN1174546A (enExample) |
| AR (1) | AR000556A1 (enExample) |
| AT (1) | ATE187959T1 (enExample) |
| AU (1) | AU702641B2 (enExample) |
| BR (1) | BR9510428A (enExample) |
| CA (1) | CA2209141A1 (enExample) |
| DE (1) | DE69514122T2 (enExample) |
| DK (1) | DK0800506T3 (enExample) |
| ES (1) | ES2139951T3 (enExample) |
| FI (1) | FI972742L (enExample) |
| HU (1) | HU215936B (enExample) |
| IL (1) | IL116634A (enExample) |
| TW (1) | TW307748B (enExample) |
| WO (1) | WO1996020168A1 (enExample) |
| ZA (1) | ZA9510902B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004529956A (ja) * | 2001-05-17 | 2004-09-30 | ロディア・シミ | 置換試薬としてのイオン性の組成物の使用、フッ素化試薬を構成する組成物およびそれを用いる方法 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69614863T2 (de) * | 1995-06-20 | 2002-01-03 | Nippon Soda Co. Ltd., Tokio/Tokyo | 2,3-dihalogen-6-trifluormethylbenzol-derivate und verfahren zu ihrer herstellung |
| DE19702282C2 (de) * | 1997-01-23 | 1998-11-19 | Hoechst Ag | Katalysator für Halex-Reaktionen |
| 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 |
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| GB995927A (en) * | 1962-10-23 | 1965-06-23 | Imp Smelting Corp Ltd | Fluorination of perhalo compounds |
| NL302228A (enExample) * | 1962-12-20 | |||
| NL129620C (enExample) * | 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 |
| DE3260500D1 (en) * | 1981-08-31 | 1984-09-06 | Ishihara Sangyo Kaisha | Process for producing 2,6-difluorobenzonitrile |
| EP0120575B1 (en) * | 1983-02-18 | 1989-06-14 | Nippon Shokubai Kagaku Kogyo Co., Ltd | 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 |
| EP0253837B1 (en) * | 1986-01-06 | 1991-10-09 | Mallinckrodt Specialty Chemicals Company | Catalytic method for producing fluoroaromatic compounds using branched alkyl pyridinium salts |
| 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 |
| DE3681033D1 (de) * | 1986-01-06 | 1991-09-26 | Mallinckrodt Inc | Katalytisches verfahren zur herstellung von fluoraomatischen verbindungen mittels n-sek-alkylpyridiniumsalze. |
| 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 |
| WO1992000270A1 (de) * | 1990-06-25 | 1992-01-09 | Hoechst Aktiengesellschaft | Verfahren zur herstellung von chlorfluornitrobenzolen und difluornitrobenzolen |
| 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 FI FI972742A patent/FI972742L/fi unknown
- 1995-11-17 DE DE69514122T patent/DE69514122T2/de not_active Expired - Fee Related
- 1995-11-17 HU HU9701844A patent/HU215936B/hu not_active IP Right Cessation
- 1995-11-17 CN CN95197478A patent/CN1174546A/zh active Pending
- 1995-11-17 ES ES95940030T patent/ES2139951T3/es not_active Expired - Lifetime
- 1995-11-17 JP JP8520445A patent/JPH10511941A/ja not_active Ceased
- 1995-11-17 WO PCT/US1995/014971 patent/WO1996020168A1/en not_active Ceased
- 1995-11-17 BR BR9510428A patent/BR9510428A/pt not_active Application Discontinuation
- 1995-11-17 AU AU41645/96A patent/AU702641B2/en not_active Ceased
- 1995-11-17 EP EP95940030A patent/EP0800506B1/en not_active Expired - Lifetime
- 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 DK DK95940030T patent/DK0800506T3/da active
- 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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004529956A (ja) * | 2001-05-17 | 2004-09-30 | ロディア・シミ | 置換試薬としてのイオン性の組成物の使用、フッ素化試薬を構成する組成物およびそれを用いる方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AR000556A1 (es) | 1997-07-10 |
| FI972742A7 (fi) | 1997-08-27 |
| EP0800506A1 (en) | 1997-10-15 |
| IL116634A0 (en) | 1996-03-31 |
| HUT77239A (hu) | 1998-03-02 |
| WO1996020168A1 (en) | 1996-07-04 |
| FI972742L (fi) | 1997-08-27 |
| DK0800506T3 (da) | 2000-05-15 |
| FI972742A0 (fi) | 1997-06-25 |
| ZA9510902B (en) | 1997-06-23 |
| ATE187959T1 (de) | 2000-01-15 |
| AU4164596A (en) | 1996-07-19 |
| IL116634A (en) | 2003-04-10 |
| DE69514122T2 (de) | 2000-04-20 |
| DE69514122D1 (de) | 2000-01-27 |
| AU702641B2 (en) | 1999-02-25 |
| CA2209141A1 (en) | 1996-07-04 |
| TW307748B (enExample) | 1997-06-11 |
| BR9510428A (pt) | 1998-07-07 |
| US5502235A (en) | 1996-03-26 |
| EP0800506B1 (en) | 1999-12-22 |
| HU215936B (hu) | 1999-03-29 |
| CN1174546A (zh) | 1998-02-25 |
| ES2139951T3 (es) | 2000-02-16 |
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