JP2013530140A - ジニトロトルエンの水素化によるトリレンジアミンの製造方法 - Google Patents
ジニトロトルエンの水素化によるトリレンジアミンの製造方法 Download PDFInfo
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- JP2013530140A JP2013530140A JP2013510563A JP2013510563A JP2013530140A JP 2013530140 A JP2013530140 A JP 2013530140A JP 2013510563 A JP2013510563 A JP 2013510563A JP 2013510563 A JP2013510563 A JP 2013510563A JP 2013530140 A JP2013530140 A JP 2013530140A
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- Prior art keywords
- reactor
- catalyst
- product
- dinitrotoluene
- discharged
- Prior art date
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- DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 title claims abstract description 84
- 238000000034 method Methods 0.000 title claims abstract description 49
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 44
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 230000008569 process Effects 0.000 title claims description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 108
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 64
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000007791 liquid phase Substances 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 238000010924 continuous production Methods 0.000 claims abstract description 3
- 239000000047 product Substances 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000000725 suspension Substances 0.000 claims description 24
- 229910052751 metal Inorganic materials 0.000 claims description 19
- 239000002184 metal Substances 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000012263 liquid product Substances 0.000 claims description 14
- 239000007789 gas Substances 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- VDCZKCIEXGXCDJ-UHFFFAOYSA-N 3-methyl-2-nitroaniline Chemical compound CC1=CC=CC(N)=C1[N+]([O-])=O VDCZKCIEXGXCDJ-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 9
- 238000005259 measurement Methods 0.000 claims description 8
- 229910052742 iron Inorganic materials 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 239000012071 phase Substances 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 230000007704 transition Effects 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 230000003068 static effect Effects 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- 238000001914 filtration Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 238000004817 gas chromatography Methods 0.000 description 9
- 239000007900 aqueous suspension Substances 0.000 description 8
- 238000003969 polarography Methods 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 241000282326 Felis catus Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 230000009849 deactivation Effects 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- XTRDKALNCIHHNI-UHFFFAOYSA-N 2,6-dinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O XTRDKALNCIHHNI-UHFFFAOYSA-N 0.000 description 5
- 229910004298 SiO 2 Inorganic materials 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000001590 oxidative effect Effects 0.000 description 5
- 231100000572 poisoning Toxicity 0.000 description 5
- 230000000607 poisoning effect Effects 0.000 description 5
- 229910052720 vanadium Inorganic materials 0.000 description 5
- RMBFBMJGBANMMK-UHFFFAOYSA-N 2,4-dinitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RMBFBMJGBANMMK-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 229910002804 graphite Inorganic materials 0.000 description 4
- 239000010439 graphite Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 150000002828 nitro derivatives Chemical class 0.000 description 4
- 238000000634 powder X-ray diffraction Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 230000007420 reactivation Effects 0.000 description 3
- 230000001603 reducing effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- -1 ammonium carboxylate Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- 239000000498 cooling water Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- CJNBYAVZURUTKZ-UHFFFAOYSA-N hafnium(iv) oxide Chemical compound O=[Hf]=O CJNBYAVZURUTKZ-UHFFFAOYSA-N 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RUIFULUFLANOCI-UHFFFAOYSA-N 3,5-Dinitrotoluene Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 RUIFULUFLANOCI-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000006230 acetylene black Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 230000005484 gravity Effects 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
- 238000005470 impregnation Methods 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000002356 laser light scattering Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical class [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000002459 porosimetry Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
-
- 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
- C07C211/49—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 having at least two amino groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10162924 | 2010-05-17 | ||
| EP10162924.4 | 2010-05-17 | ||
| PCT/EP2011/057427 WO2011144481A1 (de) | 2010-05-17 | 2011-05-09 | Verfahren zur herstellung von toluylendiamin durch hydrierung von dinitrotoluol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013530140A true JP2013530140A (ja) | 2013-07-25 |
| JP2013530140A5 JP2013530140A5 (enExample) | 2016-04-07 |
Family
ID=44358176
Family Applications (1)
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| JP2013510563A Pending JP2013530140A (ja) | 2010-05-17 | 2011-05-09 | ジニトロトルエンの水素化によるトリレンジアミンの製造方法 |
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| EP (1) | EP2571844B1 (enExample) |
| JP (1) | JP2013530140A (enExample) |
| KR (1) | KR20130080445A (enExample) |
| CN (1) | CN102892747B (enExample) |
| BR (1) | BR112012027954A2 (enExample) |
| HU (1) | HUE037511T2 (enExample) |
| MY (1) | MY156559A (enExample) |
| SG (1) | SG185374A1 (enExample) |
| WO (1) | WO2011144481A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103313962B (zh) * | 2010-12-06 | 2014-12-24 | 巴斯夫欧洲公司 | 制备芳胺的方法 |
| US8835688B2 (en) | 2011-03-16 | 2014-09-16 | Basf Se | Optimized introduction of the starting materials for a process for preparing aromatic amines by hydrogenation of nitroaromatics |
| US8895783B2 (en) | 2012-02-07 | 2014-11-25 | Basf Se | Monitoring of the stoichiometric ratio in the reaction of nitroaromatics with hydrogen |
| WO2013117622A1 (de) * | 2012-02-07 | 2013-08-15 | Basf Se | Überwachung des stöchiometrischen verhältnisses bei der umsetzung von nitroaromaten mit wasserstoff |
| US9302237B2 (en) | 2013-01-11 | 2016-04-05 | Basf Se | Apparatus and process for the continuous reaction of liquids with gases |
| US9295971B2 (en) | 2013-01-11 | 2016-03-29 | Basf Se | Apparatus and process for the continuous reaction of liquids with gases |
| WO2014108351A1 (de) | 2013-01-11 | 2014-07-17 | Basf Se | Vorrichtung und verfahren zur kontinuierlichen umsetzung von flüssigkeiten mit gasen |
| CN105593205B (zh) * | 2013-10-08 | 2017-12-12 | 科思创德国股份有限公司 | 制备二氨基甲苯的方法 |
| CN104098475A (zh) * | 2014-07-28 | 2014-10-15 | 淮安嘉诚高新化工股份有限公司 | 二硝基甲苯连续液相催化加氢还原生产二氨基甲苯的装置及方法 |
| EP3523271B1 (de) * | 2016-10-10 | 2020-12-09 | Basf Se | Katalysatormodifikation mit alkalimetall-, erdalkalimetall- oder seltenerdmetallionen in der kontinuierlichen flüssigphasen-hydrierung von nitroverbindungen |
| CN107325006A (zh) * | 2017-08-04 | 2017-11-07 | 赛鼎工程有限公司 | 一种二硝基甲苯加氢管式增稠的工艺 |
| CN111212827B (zh) * | 2017-10-16 | 2023-11-17 | 巴斯夫欧洲公司 | 通过添加氨提高硝基化合物的连续氢化中的催化剂选择性 |
| CN109053462B (zh) * | 2018-08-14 | 2021-11-05 | 浙江今晖新材料股份有限公司 | 一种对氟苯胺的制备方法 |
| CN116440898B (zh) * | 2023-05-08 | 2025-02-07 | 中国科学院金属研究所 | 用于二硝基甲苯加氢反应的原子级分散Pd-Pt催化剂及其制备方法和应用 |
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| JPS60172947A (ja) * | 1984-02-16 | 1985-09-06 | Mitsui Toatsu Chem Inc | トリレンジアミンの連続的製造方法 |
| JP2000256279A (ja) * | 1999-03-03 | 2000-09-19 | Basf Ag | アミンの製造方法 |
| JP2002532454A (ja) * | 1998-12-12 | 2002-10-02 | ビーエーエスエフ アクチェンゲゼルシャフト | アミン製造法 |
| JP2006508018A (ja) * | 2002-02-15 | 2006-03-09 | ビーエーエスエフ アクチェンゲゼルシャフト | アミンの製造方法 |
| JP2006508017A (ja) * | 2002-02-06 | 2006-03-09 | ビーエーエスエフ アクチェンゲゼルシャフト | アミンの製造方法 |
| WO2008138784A1 (de) * | 2007-05-10 | 2008-11-20 | Basf Se | Verfahren zur herstellung von aminen |
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| DE19844901C1 (de) | 1998-09-30 | 1999-11-04 | Bayer Ag | Verfahren zur Dosierung von flüssigen Nitroaromaten mit mehr als einer Nitrogruppe in Reaktoren zur Sumpfphasen-Hydrierung |
| DE19909177A1 (de) | 1999-03-03 | 2000-09-07 | Kataleuna Gmbh Catalysts | Katalysator zur Hydrierung funktioneller Gruppen und Verfahren zu seiner Herstellung |
| DE19909176A1 (de) | 1999-03-03 | 2000-09-07 | Kataleuna Gmbh Catalysts | Hydrierkatalysator und Verfahren zu seiner Herstellung |
| DE10349095A1 (de) | 2003-10-17 | 2005-05-19 | Basf Ag | Verfahren zur Herstellung von Aminen |
| CN101678335B (zh) | 2007-05-29 | 2014-04-16 | 赢创德固赛有限责任公司 | 活化的贱金属催化剂 |
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2011
- 2011-05-09 BR BR112012027954A patent/BR112012027954A2/pt not_active IP Right Cessation
- 2011-05-09 CN CN201180024339.XA patent/CN102892747B/zh active Active
- 2011-05-09 JP JP2013510563A patent/JP2013530140A/ja active Pending
- 2011-05-09 EP EP11718109.9A patent/EP2571844B1/de active Active
- 2011-05-09 WO PCT/EP2011/057427 patent/WO2011144481A1/de not_active Ceased
- 2011-05-09 HU HUE11718109A patent/HUE037511T2/hu unknown
- 2011-05-09 MY MYPI2012004968A patent/MY156559A/en unknown
- 2011-05-09 SG SG2012079281A patent/SG185374A1/en unknown
- 2011-05-09 KR KR1020127032972A patent/KR20130080445A/ko not_active Withdrawn
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60172947A (ja) * | 1984-02-16 | 1985-09-06 | Mitsui Toatsu Chem Inc | トリレンジアミンの連続的製造方法 |
| JP2002532454A (ja) * | 1998-12-12 | 2002-10-02 | ビーエーエスエフ アクチェンゲゼルシャフト | アミン製造法 |
| JP2000256279A (ja) * | 1999-03-03 | 2000-09-19 | Basf Ag | アミンの製造方法 |
| JP2006508017A (ja) * | 2002-02-06 | 2006-03-09 | ビーエーエスエフ アクチェンゲゼルシャフト | アミンの製造方法 |
| JP2006508018A (ja) * | 2002-02-15 | 2006-03-09 | ビーエーエスエフ アクチェンゲゼルシャフト | アミンの製造方法 |
| WO2008138784A1 (de) * | 2007-05-10 | 2008-11-20 | Basf Se | Verfahren zur herstellung von aminen |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011144481A1 (de) | 2011-11-24 |
| CN102892747A (zh) | 2013-01-23 |
| KR20130080445A (ko) | 2013-07-12 |
| SG185374A1 (en) | 2012-12-28 |
| HUE037511T2 (hu) | 2018-09-28 |
| BR112012027954A2 (pt) | 2017-07-25 |
| MY156559A (en) | 2016-02-26 |
| EP2571844B1 (de) | 2017-10-04 |
| EP2571844A1 (de) | 2013-03-27 |
| CN102892747B (zh) | 2014-05-21 |
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