CS213338B2 - Způsob výroby derivátů p-aminodifenylaminu - Google Patents

Info

Publication number

CS213338B2

CS213338B2 CS208378A CS208378A CS213338B2 CS 213338 B2 CS213338 B2 CS 213338B2 CS 208378 A CS208378 A CS 208378A CS 208378 A CS208378 A CS 208378A CS 213338 B2 CS213338 B2 CS 213338B2

Authority

CS

Czechoslovakia

Prior art keywords

pressure

catalyst

aminodiphenylamine

reaction

autoclave

Prior art date

1977-04-05

Links

• Espacenet
• Global Dossier
• Discuss

• ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical class C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 title claims description 13
• 238000004519 manufacturing process Methods 0.000 title description 4
• 239000003054 catalyst Substances 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 238000000034 method Methods 0.000 claims description 11
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 9
• 150000002576 ketones Chemical class 0.000 claims description 7
• 150000001875 compounds Chemical class 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 5
• 239000000203 mixture Substances 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 3
• 239000004215 Carbon black (E152) Substances 0.000 claims description 2
• 229930195733 hydrocarbon Natural products 0.000 claims description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 2
• 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 claims description 2
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
• XXYMSQQCBUKFHE-UHFFFAOYSA-N 4-nitro-n-phenylaniline Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC1=CC=CC=C1 XXYMSQQCBUKFHE-UHFFFAOYSA-N 0.000 description 12
• 239000001257 hydrogen Substances 0.000 description 9
• 229910052739 hydrogen Inorganic materials 0.000 description 9
• 238000006243 chemical reaction Methods 0.000 description 8
• OIJHFHYPXWSVPF-UHFFFAOYSA-N para-Nitrosodiphenylamine Chemical compound C1=CC(N=O)=CC=C1NC1=CC=CC=C1 OIJHFHYPXWSVPF-UHFFFAOYSA-N 0.000 description 7
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
• 239000012535 impurity Substances 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• 230000002829 reductive effect Effects 0.000 description 5
• 239000002904 solvent Substances 0.000 description 5
• 239000007795 chemical reaction product Substances 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
• 238000005804 alkylation reaction Methods 0.000 description 3
• 229910001873 dinitrogen Inorganic materials 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 238000006722 reduction reaction Methods 0.000 description 3
• NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
• UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
• 230000029936 alkylation Effects 0.000 description 2
• 238000010924 continuous production Methods 0.000 description 2
• 238000001816 cooling Methods 0.000 description 2
• 239000012043 crude product Substances 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• 230000008025 crystallization Effects 0.000 description 2
• 238000005580 one pot reaction Methods 0.000 description 2
• 238000000746 purification Methods 0.000 description 2
• 230000035484 reaction time Effects 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• ZRMMVODKVLXCBB-UHFFFAOYSA-N 1-n-cyclohexyl-4-n-phenylbenzene-1,4-diamine Chemical compound C1CCCCC1NC(C=C1)=CC=C1NC1=CC=CC=C1 ZRMMVODKVLXCBB-UHFFFAOYSA-N 0.000 description 1
• ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 description 1
• OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 description 1
• 125000000217 alkyl group Chemical group 0.000 description 1
• 230000002152 alkylating effect Effects 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• 238000010923 batch production Methods 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 150000001728 carbonyl compounds Chemical class 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 239000000356 contaminant Substances 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• 238000005265 energy consumption Methods 0.000 description 1
• 150000002431 hydrogen Chemical class 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 238000005932 reductive alkylation reaction Methods 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 238000005292 vacuum distillation Methods 0.000 description 1
• 238000005406 washing Methods 0.000 description 1