DE108064C - - Google Patents

Info

Publication number

DE108064C

DE108064C DENDAT108064D DE108064DA DE108064C DE 108064 C DE108064 C DE 108064C DE NDAT108064 D DENDAT108064 D DE NDAT108064D DE 108064D A DE108064D A DE 108064DA DE 108064 C DE108064 C DE 108064C

Authority

DE

Germany

Prior art keywords

anhydroformaldehyde

aniline

amidobenzylaniline

formation

bases

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.)

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• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 13
• 238000000034 method Methods 0.000 claims description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 3
• 150000001875 compounds Chemical class 0.000 claims description 3
• GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 claims description 3
• 150000001412 amines Chemical class 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims description 2
• 150000003141 primary amines Chemical class 0.000 claims description 2
• UAJWDYLSRSNGFH-UHFFFAOYSA-N 1,3,5-tris(4-methylphenyl)-1,3,5-triazinane Chemical compound C1=CC(C)=CC=C1N1CN(C=2C=CC(C)=CC=2)CN(C=2C=CC(C)=CC=2)C1 UAJWDYLSRSNGFH-UHFFFAOYSA-N 0.000 claims 1
• 150000004982 aromatic amines Chemical class 0.000 claims 1
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
• 150000003142 primary aromatic amines Chemical class 0.000 claims 1
• 230000015572 biosynthetic process Effects 0.000 description 7
• 230000008707 rearrangement Effects 0.000 description 6
• HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
• ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 3
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
• HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
• -1 compounds primary aromatic amines Chemical class 0.000 description 2
• RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
• VASMRQAVWVVDPA-UHFFFAOYSA-N 1,3,5-triphenyl-1,3,5-triazinane Chemical compound C1N(C=2C=CC=CC=2)CN(C=2C=CC=CC=2)CN1C1=CC=CC=C1 VASMRQAVWVVDPA-UHFFFAOYSA-N 0.000 description 1
• AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
• 125000003118 aryl group Chemical group 0.000 description 1
• 238000001311 chemical methods and process Methods 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
• JQKBUTDZZRGQDR-UHFFFAOYSA-N hydron;4-methylaniline;chloride Chemical compound Cl.CC1=CC=C(N)C=C1 JQKBUTDZZRGQDR-UHFFFAOYSA-N 0.000 description 1
• WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1