JPS5927850A - フロロ安息香酸類の製造法 - Google Patents

フロロ安息香酸類の製造法

Info

Publication number: JPS5927850A
Authority: JP; Japan
Prior art keywords: fluorotoluene; reaction; compound; heavy metal; chloro
Prior art date: 1982-08-06
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.): Granted

Application number

JP57136269A

Other languages

English (en)

Japanese (ja)

Other versions

JPH051252B2 (fr

Inventor

Kura Yamada

蔵山田

Ryoichi Hasegawa

良一長谷川

Fumiki Oosato

大里　ふみき

Shigeru Kawamoto

滋河本

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nippon Kayaku Co Ltd

Original Assignee

Nippon Kayaku Co Ltd

Priority date (The priority date 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 date listed.)

1982-08-06

Filing date

1982-08-06

Publication date

1984-02-14

1982-08-06 Application filed by Nippon Kayaku Co Ltd filed Critical Nippon Kayaku Co Ltd

1982-08-06 Priority to JP57136269A priority Critical patent/JPS5927850A/ja

1984-02-14 Publication of JPS5927850A publication Critical patent/JPS5927850A/ja

1993-01-07 Publication of JPH051252B2 publication Critical patent/JPH051252B2/ja

Status Granted legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title description 2
NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 title 1
229910001385 heavy metal Inorganic materials 0.000 claims abstract description 17
150000002736 metal compounds Chemical class 0.000 claims abstract description 16
229910052794 bromium Inorganic materials 0.000 claims abstract description 10
229910052748 manganese Inorganic materials 0.000 claims abstract description 6
238000004519 manufacturing process Methods 0.000 claims description 2
229910052727 yttrium Inorganic materials 0.000 claims description 2
235000010233 benzoic acid Nutrition 0.000 claims 1
150000001559 benzoic acids Chemical class 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 42
-1 bromine compound Chemical class 0.000 abstract description 9
238000007254 oxidation reaction Methods 0.000 abstract description 9
239000011572 manganese Substances 0.000 abstract description 8
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 abstract description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 7
150000001875 compounds Chemical class 0.000 abstract description 7
230000003647 oxidation Effects 0.000 abstract description 7
239000003054 catalyst Substances 0.000 abstract description 6
229940011182 cobalt acetate Drugs 0.000 abstract description 6
QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 abstract description 6
WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract description 6
MMZYCBHLNZVROM-UHFFFAOYSA-N 1-fluoro-2-methylbenzene Chemical class CC1=CC=CC=C1F MMZYCBHLNZVROM-UHFFFAOYSA-N 0.000 abstract description 5
CSARJIQZOSVYHA-UHFFFAOYSA-N 2-chloro-4-fluoro-1-methylbenzene Chemical compound CC1=CC=C(F)C=C1Cl CSARJIQZOSVYHA-UHFFFAOYSA-N 0.000 abstract description 5
239000007791 liquid phase Substances 0.000 abstract description 5
229940071125 manganese acetate Drugs 0.000 abstract description 4
UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 abstract description 4
229910052759 nickel Inorganic materials 0.000 abstract description 3
239000002904 solvent Substances 0.000 abstract description 3
229910052726 zirconium Inorganic materials 0.000 abstract description 3
239000003905 agrochemical Substances 0.000 abstract description 2
229910052802 copper Inorganic materials 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract description 2
229910052742 iron Inorganic materials 0.000 abstract description 2
229910052703 rhodium Inorganic materials 0.000 abstract description 2
229910052707 ruthenium Inorganic materials 0.000 abstract description 2
229910052720 vanadium Inorganic materials 0.000 abstract description 2
230000001590 oxidative effect Effects 0.000 abstract 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 36
229910052760 oxygen Inorganic materials 0.000 description 20
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 19
239000001301 oxygen Substances 0.000 description 19
239000013078 crystal Substances 0.000 description 16
238000003756 stirring Methods 0.000 description 15
239000011521 glass Substances 0.000 description 10
239000005457 ice water Substances 0.000 description 8
238000000034 method Methods 0.000 description 8
239000002912 waste gas Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
GRPWQLDSGNZEQE-UHFFFAOYSA-N 2-chloro-4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1Cl GRPWQLDSGNZEQE-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
RRKPMLZRLKTDQV-UHFFFAOYSA-N 2-bromo-4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1Br RRKPMLZRLKTDQV-UHFFFAOYSA-N 0.000 description 5
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 5
239000002253 acid Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
229910001882 dioxygen Inorganic materials 0.000 description 5
SFGFOJPGCOYQJK-UHFFFAOYSA-N 2-bromo-4-fluoro-1-methylbenzene Chemical compound CC1=CC=C(F)C=C1Br SFGFOJPGCOYQJK-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
238000005260 corrosion Methods 0.000 description 3
230000007797 corrosion Effects 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
229940082328 manganese acetate tetrahydrate Drugs 0.000 description 3
CESXSDZNZGSWSP-UHFFFAOYSA-L manganese(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Mn+2].CC([O-])=O.CC([O-])=O CESXSDZNZGSWSP-UHFFFAOYSA-L 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000010936 titanium Substances 0.000 description 3
229910052719 titanium Inorganic materials 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
BBYDXOIZLAWGSL-UHFFFAOYSA-N 4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
239000003999 initiator Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
150000005526 organic bromine compounds Chemical class 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000002994 raw material Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
RYEMWXVGSRAQQQ-UHFFFAOYSA-N (2-chloro-4-fluorophenyl)methyl acetate Chemical compound CC(=O)OCC1=CC=C(F)C=C1Cl RYEMWXVGSRAQQQ-UHFFFAOYSA-N 0.000 description 1
IPMPJTQRCBFUMU-UHFFFAOYSA-N 1,3-dibromo-5-fluoro-2-methylbenzene Chemical compound CC1=C(Br)C=C(F)C=C1Br IPMPJTQRCBFUMU-UHFFFAOYSA-N 0.000 description 1
GAUUDQVOPUKGJD-UHFFFAOYSA-N 1-(bromomethyl)-2-chloro-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C(Cl)=C1 GAUUDQVOPUKGJD-UHFFFAOYSA-N 0.000 description 1
NVNPLEPBDPJYRZ-UHFFFAOYSA-N 1-(bromomethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C=C1 NVNPLEPBDPJYRZ-UHFFFAOYSA-N 0.000 description 1
ADIZFWOXYXDVDL-UHFFFAOYSA-N 1-bromo-3-chloro-5-fluoro-2-methylbenzene Chemical compound CC1=C(Cl)C=C(F)C=C1Br ADIZFWOXYXDVDL-UHFFFAOYSA-N 0.000 description 1
AKYAOPGWEAILOD-UHFFFAOYSA-N 1-bromo-4-chloro-5-fluoro-2-methylbenzene Chemical compound CC1=CC(Cl)=C(F)C=C1Br AKYAOPGWEAILOD-UHFFFAOYSA-N 0.000 description 1
RJPNVPITBYXBNB-UHFFFAOYSA-N 1-bromo-4-fluoro-2-methylbenzene Chemical compound CC1=CC(F)=CC=C1Br RJPNVPITBYXBNB-UHFFFAOYSA-N 0.000 description 1
NIOGDCDTKPQEAT-UHFFFAOYSA-N 1-chloro-4-fluoro-2-methylbenzene Chemical compound CC1=CC(F)=CC=C1Cl NIOGDCDTKPQEAT-UHFFFAOYSA-N 0.000 description 1
WRWPPGUCZBJXKX-UHFFFAOYSA-N 1-fluoro-4-methylbenzene Chemical compound CC1=CC=C(F)C=C1 WRWPPGUCZBJXKX-UHFFFAOYSA-N 0.000 description 1
102100027621 2'-5'-oligoadenylate synthase 2 Human genes 0.000 description 1
QLRKALMVPCQTMU-UHFFFAOYSA-N 2-bromo-1-fluoro-4-methylbenzene Chemical compound CC1=CC=C(F)C(Br)=C1 QLRKALMVPCQTMU-UHFFFAOYSA-N 0.000 description 1
WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
ONELILMJNOWXSA-UHFFFAOYSA-N 3-bromo-4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(Br)=C1 ONELILMJNOWXSA-UHFFFAOYSA-N 0.000 description 1
YZFVUQSAJMLFOZ-UHFFFAOYSA-N 4-bromo-2-fluoro-1-methylbenzene Chemical compound CC1=CC=C(Br)C=C1F YZFVUQSAJMLFOZ-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
229910052684 Cerium Inorganic materials 0.000 description 1
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
229910019131 CoBr2 Inorganic materials 0.000 description 1
101001008910 Homo sapiens 2'-5'-oligoadenylate synthase 2 Proteins 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
229910021568 Manganese(II) bromide Inorganic materials 0.000 description 1
229910021585 Nickel(II) bromide Inorganic materials 0.000 description 1
235000014676 Phragmites communis Nutrition 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
238000003916 acid precipitation Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
ZCGHEBMEQXMRQL-UHFFFAOYSA-N benzyl 2-carbamoylpyrrolidine-1-carboxylate Chemical compound NC(=O)C1CCCN1C(=O)OCC1=CC=CC=C1 ZCGHEBMEQXMRQL-UHFFFAOYSA-N 0.000 description 1
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
KDPAWGWELVVRCH-UHFFFAOYSA-N bromoacetic acid Chemical compound OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000003426 co-catalyst Substances 0.000 description 1
GAYAMOAYBXKUII-UHFFFAOYSA-L cobalt(2+);dibenzoate Chemical compound [Co+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 GAYAMOAYBXKUII-UHFFFAOYSA-L 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
RJYMRRJVDRJMJW-UHFFFAOYSA-L dibromomanganese Chemical compound Br[Mn]Br RJYMRRJVDRJMJW-UHFFFAOYSA-L 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000004817 gas chromatography 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
239000012535 impurity Substances 0.000 description 1
230000006698 induction Effects 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
230000016507 interphase Effects 0.000 description 1
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
229910001623 magnesium bromide Inorganic materials 0.000 description 1
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
238000002156 mixing Methods 0.000 description 1
UIEKYBOPAVTZKW-UHFFFAOYSA-L naphthalene-2-carboxylate;nickel(2+) Chemical compound [Ni+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 UIEKYBOPAVTZKW-UHFFFAOYSA-L 0.000 description 1
IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
150000003613 toluenes Chemical class 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP57136269A 1982-08-06 1982-08-06 フロロ安息香酸類の製造法 Granted JPS5927850A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP57136269A JPS5927850A (ja)	1982-08-06	1982-08-06	フロロ安息香酸類の製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP57136269A JPS5927850A (ja)	1982-08-06	1982-08-06	フロロ安息香酸類の製造法

Publications (2)

Publication Number	Publication Date
JPS5927850A true JPS5927850A (ja)	1984-02-14
JPH051252B2 JPH051252B2 (fr)	1993-01-07

Family

ID=15171237

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57136269A Granted JPS5927850A (ja)	1982-08-06	1982-08-06	フロロ安息香酸類の製造法

Country Status (1)

Country	Link
JP (1)	JPS5927850A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH02174746A (ja) *	1988-09-19	1990-07-06	Nissan Chem Ind Ltd	置換安息香酸の製造方法
WO2024225002A1 (fr) *	2023-04-25	2024-10-31	住友ベークライト株式会社	Procédé de production d'acide 4-hydroxybenzoïque

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5553239A (en) *	1978-10-13	1980-04-18	Ube Ind Ltd	Preparation of 2,4-dichlorobenzoic acid
JPS56131539A (en) *	1980-02-22	1981-10-15	Riedel De Haen Ag	Substituted bromfluorobenzene and manufacture
JPS5782334A (en) *	1980-09-19	1982-05-22	Bayer Ag	Manufacture of 3-bromo-4-fluorobenzoic acid

1982
- 1982-08-06 JP JP57136269A patent/JPS5927850A/ja active Granted

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5553239A (en) *	1978-10-13	1980-04-18	Ube Ind Ltd	Preparation of 2,4-dichlorobenzoic acid
JPS56131539A (en) *	1980-02-22	1981-10-15	Riedel De Haen Ag	Substituted bromfluorobenzene and manufacture
JPS5782334A (en) *	1980-09-19	1982-05-22	Bayer Ag	Manufacture of 3-bromo-4-fluorobenzoic acid

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH02174746A (ja) *	1988-09-19	1990-07-06	Nissan Chem Ind Ltd	置換安息香酸の製造方法
WO2024225002A1 (fr) *	2023-04-25	2024-10-31	住友ベークライト株式会社	Procédé de production d'acide 4-hydroxybenzoïque

Also Published As

Publication number	Publication date
JPH051252B2 (fr)	1993-01-07

Publication	Publication Date	Title
JPS582222B2 (ja)	1983-01-14	芳香族ポリカルボン酸の製造法
US4195040A (en)	1980-03-25	Process for preparing a methyl-substituted benzaldehyde
JPS5927850A (ja)	1984-02-14	フロロ安息香酸類の製造法
EP0051215A2 (fr)	1982-05-12	Procédés et intermédiaires pour la synthése de 3-aryl-3-hydroxy-phtalimidines
JP4913962B2 (ja)	2012-04-11	フェニルエチニルフタル酸無水物誘導体の製造方法
US5155258A (en)	1992-10-13	Substituted benzoic acids
JPS6212772B2 (fr)	1987-03-20
WO2023176687A1 (fr)	2023-09-21	Composé de biphénanthrène ou sel de métal alcalin de celui-ci
JPH035449A (ja)	1991-01-11	シアン化アシルの合成方法
JPS62255456A (ja)	1987-11-07	ジエチルホルムアミドの製造方法
US4228302A (en)	1980-10-14	Process for preparing a methyl-substituted benzaldehyde
JP2927023B2 (ja)	1999-07-28	芳香族テトラカルボン酸の製造方法
US3983146A (en)	1976-09-28	Process for the production of α, α, α, α', α',α', -hexakisaryl-1,3-and-1,4-dimethyl benzenes
US4080371A (en)	1978-03-21	Process for the production of α, α, α, α', α',α'-hexakisaryl-1,3- and -1,4-dimethyl benzenes
EP0255384B1 (fr)	1991-10-16	4,4-bis(carboxyphénylsulfonyl)diphényl éthers, leur procédé de préparation et emploi de ceux-ci
US4220801A (en)	1980-09-02	Process for making 4-aroyl-substituted phenoxyacetic acids
JPH04330035A (ja)	1992-11-18	４，４′−ビス（４−クロロベンゾイル）ベンゾフェノンおよびその製造方法
JPS5948817B2 (ja)	1984-11-29	ε−カプロラクトンとカルボン酸類との同時製造法
JPH09286757A (ja)	1997-11-04	芳香族カルボン酸の製造方法
CN120607495A (zh)	2025-09-09	3-(4,5-二氢-3-异恶唑基)-2-甲基-4-(甲基磺酰基)苯甲酸的制备方法
JPS6330449A (ja)	1988-02-09	２−シクロペンテノン誘導体の製法
JPH0768247B2 (ja)	1995-07-26	ジアリ−ルジカルボン酸の製造方法
JPH01316342A (ja)	1989-12-21	アニス酸の製造方法
JPS6245859B2 (fr)	1987-09-29
JPH0324023A (ja)	1991-02-01	２―（４―イソブチルフエニル）―２―ブテン

JPS5927850A - フロロ安息香酸類の製造法 - Google Patents

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