DE141893C - - Google Patents

Info

Publication number

DE141893C

DE141893C DENDAT141893D DE141893DA DE141893C DE 141893 C DE141893 C DE 141893C DE NDAT141893 D DENDAT141893 D DE NDAT141893D DE 141893D A DE141893D A DE 141893DA DE 141893 C DE141893 C DE 141893C

Authority

DE

Germany

Prior art keywords

acid

nitro

aniline

water

phthalanil

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.)

Active

Links

• Espacenet
• Global Dossier
• DPMA
• Discuss

• 238000000034 method Methods 0.000 claims description 5
• 238000002360 preparation method Methods 0.000 claims description 5
• LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 4
• JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 4
• 239000007859 condensation product Substances 0.000 claims description 4
• 150000002828 nitro derivatives Chemical class 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 150000001875 compounds Chemical class 0.000 claims description 2
• XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 1
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 18
• 239000002253 acid Substances 0.000 description 10
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
• MFUPLJQNEXUUDW-UHFFFAOYSA-N 2-phenylisoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1=CC=CC=C1 MFUPLJQNEXUUDW-UHFFFAOYSA-N 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• 239000000203 mixture Substances 0.000 description 7
• 238000006396 nitration reaction Methods 0.000 description 7
• 238000010438 heat treatment Methods 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
• TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 4
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• 239000000155 melt Substances 0.000 description 3
• 230000000802 nitrating effect Effects 0.000 description 3
• 239000000047 product Substances 0.000 description 3
• 239000007787 solid Substances 0.000 description 3
• DLURHXYXQYMPLT-UHFFFAOYSA-N 2-nitro-p-toluidine Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1 DLURHXYXQYMPLT-UHFFFAOYSA-N 0.000 description 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
• 229960000583 acetic acid Drugs 0.000 description 2
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
• 238000003776 cleavage reaction Methods 0.000 description 2
• 238000001035 drying Methods 0.000 description 2
• RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• 230000007017 scission Effects 0.000 description 2
• CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
• DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
• DKDILURPBGKQSO-UHFFFAOYSA-N 5-(2-methylphenyl)isoindole-1,3-dione Chemical compound Cc1ccccc1-c1ccc2C(=O)NC(=O)c2c1 DKDILURPBGKQSO-UHFFFAOYSA-N 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 125000003368 amide group Chemical group 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• 150000004982 aromatic amines Chemical class 0.000 description 1
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 238000006243 chemical reaction Methods 0.000 description 1
• 230000008030 elimination Effects 0.000 description 1
• 238000003379 elimination reaction Methods 0.000 description 1
• 239000012362 glacial acetic acid Substances 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 239000012452 mother liquor Substances 0.000 description 1
• UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical compound C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 description 1
• 150000005002 naphthylamines Chemical class 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• -1 nitro-p-tolylphthalimide Chemical compound 0.000 description 1
• FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
• AFDMODCXODAXLC-UHFFFAOYSA-N phenylmethanimine Chemical class N=CC1=CC=CC=C1 AFDMODCXODAXLC-UHFFFAOYSA-N 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 238000003825 pressing Methods 0.000 description 1
• 238000010298 pulverizing process Methods 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 238000011084 recovery Methods 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 238000007127 saponification reaction Methods 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 150000004992 toluidines Chemical class 0.000 description 1