DD207902A5 - Verfahren zur herstellung von ortho-methylanilinen - Google Patents

Verfahren zur herstellung von ortho-methylanilinen Download PDF

Info

Publication number: DD207902A5
Authority: DD; German Democratic Republic
Prior art keywords: ortho; halide; item; solution; solvent
Prior art date: 1982-03-17

Application number

DD83248849A

Other languages

German (de)

English (en)

Inventor

John P Chupp

Terry M Balthazor

Original Assignee

Monsanto Co

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.)

1982-03-17

Filing date

1983-03-16

Publication date

1984-03-21

1983-03-16 Application filed by Monsanto Co filed Critical Monsanto Co

1984-03-21 Publication of DD207902A5 publication Critical patent/DD207902A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 3
150000004820 halides Chemical class 0.000 claims abstract description 39
238000000034 method Methods 0.000 claims abstract description 36
239000002253 acid Substances 0.000 claims abstract description 18
PAYRUJLWNCNPSJ-UHFFFAOYSA-O phenylazanium Chemical class [NH3+]C1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-O 0.000 claims abstract description 13
238000002360 preparation method Methods 0.000 claims abstract description 8
RNVCVTLRINQCPJ-UHFFFAOYSA-N ortho-methyl aniline Natural products CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims abstract description 6
239000000243 solution Substances 0.000 claims description 31
-1 anilinium halide Chemical class 0.000 claims description 29
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
239000002904 solvent Substances 0.000 claims description 19
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 18
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 18
150000003462 sulfoxides Chemical class 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 15
239000007858 starting material Substances 0.000 claims description 13
239000006227 byproduct Substances 0.000 claims description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
229910000039 hydrogen halide Inorganic materials 0.000 claims description 9
239000012433 hydrogen halide Substances 0.000 claims description 9
239000011593 sulfur Substances 0.000 claims description 9
239000012442 inert solvent Substances 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 7
238000006386 neutralization reaction Methods 0.000 claims description 6
GLBQVJGBPFPMMV-UHFFFAOYSA-N sulfilimine Chemical compound S=N GLBQVJGBPFPMMV-UHFFFAOYSA-N 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 5
150000003464 sulfur compounds Chemical class 0.000 claims description 5
238000011065 in-situ storage Methods 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 3
230000003197 catalytic effect Effects 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
230000002140 halogenating effect Effects 0.000 claims description 3
230000001590 oxidative effect Effects 0.000 claims description 3
239000002244 precipitate Substances 0.000 claims description 3
OGEKUKUBGHKPHN-UHFFFAOYSA-N 2-[[2-amino-3-(trifluoromethyl)phenyl]methylsulfinylmethyl]-6-(trifluoromethyl)aniline Chemical compound C1=CC=C(C(F)(F)F)C(N)=C1CS(=O)CC1=CC=CC(C(F)(F)F)=C1N OGEKUKUBGHKPHN-UHFFFAOYSA-N 0.000 claims 1
ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims 1
150000002895 organic esters Chemical class 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 28
150000001448 anilines Chemical class 0.000 abstract description 3
239000012429 reaction media Substances 0.000 abstract description 2
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
125000001424 substituent group Chemical group 0.000 description 13
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
125000000217 alkyl group Chemical group 0.000 description 12
239000003054 catalyst Substances 0.000 description 12
238000005984 hydrogenation reaction Methods 0.000 description 8
238000011282 treatment Methods 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
238000006956 Pummerer reaction Methods 0.000 description 5
125000003342 alkenyl group Chemical group 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000000376 reactant Substances 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
230000002159 abnormal effect Effects 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
125000000304 alkynyl group Chemical group 0.000 description 4
HTMQZWFSTJVJEQ-UHFFFAOYSA-N benzylsulfinylmethylbenzene Chemical group C=1C=CC=CC=1CS(=O)CC1=CC=CC=C1 HTMQZWFSTJVJEQ-UHFFFAOYSA-N 0.000 description 4
230000005587 bubbling Effects 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
125000001188 haloalkyl group Chemical group 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000004821 distillation Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000012467 final product Substances 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
REIWBMTUTDSMAI-UHFFFAOYSA-N 2-(chloromethyl)-6-(trifluoromethyl)aniline;hydrochloride Chemical compound [Cl-].[NH3+]C1=C(CCl)C=CC=C1C(F)(F)F REIWBMTUTDSMAI-UHFFFAOYSA-N 0.000 description 2
AWUFEMPPABUXSZ-UHFFFAOYSA-N 2-(methylsulfanylmethyl)-6-(trifluoromethyl)aniline Chemical compound CSCC1=CC=CC(C(F)(F)F)=C1N AWUFEMPPABUXSZ-UHFFFAOYSA-N 0.000 description 2
LXPCTHRQJVSSIQ-UHFFFAOYSA-N 2-methyl-6-(trifluoromethyl)aniline Chemical compound CC1=CC=CC(C(F)(F)F)=C1N LXPCTHRQJVSSIQ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
125000004183 alkoxy alkyl group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
238000010533 azeotropic distillation Methods 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000000269 nucleophilic effect Effects 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
230000008707 rearrangement Effects 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
150000003568 thioethers Chemical class 0.000 description 2
238000005406 washing Methods 0.000 description 2
CTLRITSBJZQTNM-UHFFFAOYSA-N 2-(chloromethyl)-6-(trifluoromethyl)aniline Chemical compound NC1=C(CCl)C=CC=C1C(F)(F)F CTLRITSBJZQTNM-UHFFFAOYSA-N 0.000 description 1
QTEYDTXRTCNUCO-UHFFFAOYSA-N 2-(methylsulfinylmethyl)-6-(trifluoromethyl)aniline Chemical compound CS(=O)CC1=CC=CC(C(F)(F)F)=C1N QTEYDTXRTCNUCO-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
102100037804 Inositol oxygenase Human genes 0.000 description 1
241000143973 Libytheinae Species 0.000 description 1
101150089916 Miox gene Proteins 0.000 description 1
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical class CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000007605 air drying Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000003302 alkenyloxy group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
125000005133 alkynyloxy group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
125000005997 bromomethyl group Chemical group 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000005111 carboxyalkoxy group Chemical group 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000006477 desulfuration reaction Methods 0.000 description 1
230000023556 desulfurization Effects 0.000 description 1
239000003599 detergent Substances 0.000 description 1
125000006003 dichloroethyl group Chemical group 0.000 description 1
239000000539 dimer Substances 0.000 description 1
238000004851 dishwashing Methods 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
231100001261 hazardous Toxicity 0.000 description 1
210000003128 head Anatomy 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
VOAJIZWMDUSXFK-UHFFFAOYSA-N n-(chloromethyl)aniline Chemical compound ClCNC1=CC=CC=C1 VOAJIZWMDUSXFK-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
125000006187 phenyl benzyl group Chemical group 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000012545 processing Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
RFIZPYFNEYSHKG-UHFFFAOYSA-N pyrrolidine-2,5-dione;sodium Chemical compound [Na].O=C1CCC(=O)N1 RFIZPYFNEYSHKG-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000007634 remodeling Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000004894 snout Anatomy 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
ORXDFZVXVSSTPU-UHFFFAOYSA-J tetrapotassium tetrachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[K+].[K+].[K+].[K+] ORXDFZVXVSSTPU-UHFFFAOYSA-J 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
239000008096 xylene Substances 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/45—Monoamines
- C07C211/46—Aniline

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD83248849A 1982-03-17 1983-03-16 Verfahren zur herstellung von ortho-methylanilinen DD207902A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US35877282A	1982-03-17	1982-03-17

Publications (1)

Publication Number	Publication Date
DD207902A5 true DD207902A5 (de)	1984-03-21

Family

ID=23410977

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD83248849A DD207902A5 (de)	1982-03-17	1983-03-16	Verfahren zur herstellung von ortho-methylanilinen

Country Status (15)

Country	Link
EP (1)	EP0089331B1 (fr)
JP (1)	JPS58167548A (fr)
KR (1)	KR840004057A (fr)
AT (1)	ATE11402T1 (fr)
AU (1)	AU1249183A (fr)
DD (1)	DD207902A5 (fr)
DE (1)	DE3360055D1 (fr)
GB (1)	GB2116556B (fr)
HU (1)	HU188264B (fr)
NZ (1)	NZ203591A (fr)
PH (1)	PH18771A (fr)
PL (1)	PL241048A1 (fr)
PT (1)	PT76400B (fr)
RO (1)	RO87598A (fr)
ZA (1)	ZA831843B (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3985756A (en) *	1973-01-29	1976-10-12	The Ohio State University Research Foundation	Process for producing azasulfonium salts and rearrangement thereof to thio-ethers

1983
- 1983-03-15 AT AT83870022T patent/ATE11402T1/de not_active IP Right Cessation
- 1983-03-15 EP EP83870022A patent/EP0089331B1/fr not_active Expired
- 1983-03-15 DE DE8383870022T patent/DE3360055D1/de not_active Expired
- 1983-03-16 HU HU83892A patent/HU188264B/hu unknown
- 1983-03-16 NZ NZ203591A patent/NZ203591A/en unknown
- 1983-03-16 PL PL24104883A patent/PL241048A1/xx unknown
- 1983-03-16 PH PH28656A patent/PH18771A/en unknown
- 1983-03-16 JP JP58042526A patent/JPS58167548A/ja active Pending
- 1983-03-16 RO RO83110353A patent/RO87598A/fr unknown
- 1983-03-16 AU AU12491/83A patent/AU1249183A/en not_active Abandoned
- 1983-03-16 ZA ZA831843A patent/ZA831843B/xx unknown
- 1983-03-16 KR KR1019830001059A patent/KR840004057A/ko not_active Abandoned
- 1983-03-16 GB GB08307282A patent/GB2116556B/en not_active Expired
- 1983-03-16 DD DD83248849A patent/DD207902A5/de unknown
- 1983-03-16 PT PT76400A patent/PT76400B/pt unknown

Also Published As

Publication number	Publication date
HU188264B (en)	1986-03-28
GB2116556A (en)	1983-09-28
AU1249183A (en)	1983-09-22
DE3360055D1 (en)	1985-03-07
RO87598B (ro)	1985-08-31
ATE11402T1 (de)	1985-02-15
GB8307282D0 (en)	1983-04-20
KR840004057A (ko)	1984-10-06
PL241048A1 (en)	1983-10-10
EP0089331B1 (fr)	1985-01-23
NZ203591A (en)	1986-04-11
PT76400A (en)	1983-04-01
ZA831843B (en)	1984-03-28
JPS58167548A (ja)	1983-10-03
GB2116556B (en)	1986-01-15
PH18771A (en)	1985-09-25
PT76400B (en)	1985-12-09
EP0089331A1 (fr)	1983-09-21
RO87598A (fr)	1985-08-31

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