CN1332149A - 甲苯二胺和水的混合物及其在制甲苯二异氰酸酯中的用途 - Google Patents
甲苯二胺和水的混合物及其在制甲苯二异氰酸酯中的用途 Download PDFInfo
- Publication number
- CN1332149A CN1332149A CN00131796A CN00131796A CN1332149A CN 1332149 A CN1332149 A CN 1332149A CN 00131796 A CN00131796 A CN 00131796A CN 00131796 A CN00131796 A CN 00131796A CN 1332149 A CN1332149 A CN 1332149A
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- tda
- water
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- reaction
- Prior art date
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 125
- 239000000203 mixture Substances 0.000 title claims abstract description 80
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 title claims description 141
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 title description 37
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 39
- 239000006227 byproduct Substances 0.000 claims description 14
- 150000004998 toluenediamines Chemical class 0.000 claims description 9
- -1 toluylene diamine Chemical class 0.000 abstract description 3
- 238000007711 solidification Methods 0.000 abstract description 2
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 abstract 1
- 230000008023 solidification Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 38
- DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 description 29
- 238000004821 distillation Methods 0.000 description 28
- 239000002904 solvent Substances 0.000 description 28
- 238000004519 manufacturing process Methods 0.000 description 25
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 13
- 238000005984 hydrogenation reaction Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000002699 waste material Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 241000276425 Xiphophorus maculatus Species 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000006200 vaporizer Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000004062 sedimentation Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CZSSKBQAJULWPY-UHFFFAOYSA-N 2-undecylsulfanylacetic acid Chemical compound CCCCCCCCCCCSCC(O)=O CZSSKBQAJULWPY-UHFFFAOYSA-N 0.000 description 2
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 150000005182 dinitrobenzenes Chemical class 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 239000012943 hotmelt Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 2
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010013647 Drowning Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003657 drainage water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Images
Classifications
-
- 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
- C07C211/50—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 with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- 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
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Claims (8)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19528781A DE19528781A1 (de) | 1995-08-04 | 1995-08-04 | Verfahren zur Herstellung von Toluylendiisocyanat, spezielle Gemische aus Toluylendiamin und Wasser und deren Verwendung zur Herstellung von Toluylendiisocyanat |
DE19528781.9 | 1995-08-04 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN96111631A Division CN1070474C (zh) | 1995-08-04 | 1996-08-02 | 甲苯二异氰酸酯的制法和甲苯二胺和水的特定混合物及其在制备甲苯二异氰酸酯中的用途 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1332149A true CN1332149A (zh) | 2002-01-23 |
CN1163470C CN1163470C (zh) | 2004-08-25 |
Family
ID=7768754
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB001317962A Expired - Lifetime CN1163470C (zh) | 1995-08-04 | 1996-08-02 | 甲苯二胺和水的混合物及其在制甲苯二异氰酸酯中的用途 |
CN96111631A Expired - Lifetime CN1070474C (zh) | 1995-08-04 | 1996-08-02 | 甲苯二异氰酸酯的制法和甲苯二胺和水的特定混合物及其在制备甲苯二异氰酸酯中的用途 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN96111631A Expired - Lifetime CN1070474C (zh) | 1995-08-04 | 1996-08-02 | 甲苯二异氰酸酯的制法和甲苯二胺和水的特定混合物及其在制备甲苯二异氰酸酯中的用途 |
Country Status (15)
Country | Link |
---|---|
US (2) | US5849947A (zh) |
EP (2) | EP1090906A1 (zh) |
JP (1) | JP4095685B2 (zh) |
KR (1) | KR100453862B1 (zh) |
CN (2) | CN1163470C (zh) |
BR (1) | BR9603278A (zh) |
CA (1) | CA2182654A1 (zh) |
CZ (1) | CZ292604B6 (zh) |
DE (2) | DE19528781A1 (zh) |
ES (1) | ES2176380T3 (zh) |
PL (1) | PL184186B1 (zh) |
PT (1) | PT757034E (zh) |
RU (1) | RU2202537C2 (zh) |
TW (1) | TW374080B (zh) |
UA (1) | UA47399C2 (zh) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100311692B1 (ko) * | 1997-12-23 | 2001-11-15 | 신현준 | 활성탄소 섬유의 제조방법 |
EP1371633A1 (en) * | 2002-06-14 | 2003-12-17 | Bayer Ag | Process for the purification of mixtures of toluenediisocyanate incorporating a dividing-wall distillation column |
EP1413571B1 (en) * | 2002-10-22 | 2006-08-23 | Bayer MaterialScience AG | Process for the purification of toluenediisocyanate incorporating a dividing-wall distillation column for the final purification |
DE10260093A1 (de) * | 2002-12-19 | 2004-07-01 | Basf Ag | Verfahren zur Abtrennung von Isocyanaten aus einem Reaktionsgemisch |
JP5175033B2 (ja) * | 2005-03-10 | 2013-04-03 | 三井化学株式会社 | ポリイソシアネートの製造方法およびポリイソシアネートの製造装置 |
CN101838223B (zh) * | 2005-03-10 | 2013-04-03 | 三井化学株式会社 | 多异氰酸酯的制造方法和多异氰酸酯的制造装置 |
DE102005032430A1 (de) * | 2005-07-12 | 2007-01-25 | Bayer Materialscience Ag | Verfahren zur Herstellung von Toluylendiamin |
HUE033435T2 (en) * | 2005-07-12 | 2017-11-28 | Covestro Deutschland Ag | Process for preparing toluenediamine |
JP4791783B2 (ja) * | 2005-08-31 | 2011-10-12 | 三井化学株式会社 | ポリイソシアネートの製造方法 |
DE102006022447A1 (de) * | 2006-05-13 | 2007-11-15 | Bayer Materialscience Ag | Verfahren zur gekoppelten Herstellung von Chlor und Isocyanaten |
US8030522B2 (en) * | 2006-06-07 | 2011-10-04 | Bayer Materialscience Llc | Process for the production of toluene diisocyanate |
CN100455559C (zh) * | 2006-11-08 | 2009-01-28 | 大连理工大学 | 芳香族硝基化合物还原制备芳胺的方法 |
DE102006059678A1 (de) * | 2006-12-18 | 2008-06-19 | Bayer Materialscience Ag | Verfahren zur Herstellung von aromatischen Aminen |
DE102006060572A1 (de) † | 2006-12-19 | 2008-06-26 | Bayer Materialscience Ag | Verfahren zur Herstellung von Toluylendiaminen durch katalytische Hydrierung von Dinitrotoluolen |
WO2009069584A1 (ja) * | 2007-11-27 | 2009-06-04 | Mitsui Chemicals Polyurethanes, Inc. | トリレンジアミンの脱水方法および脱水装置 |
ES2400332T3 (es) | 2008-11-19 | 2013-04-09 | Basf Se | Método para la producción de un isocianato |
CN101712621B (zh) * | 2009-09-02 | 2012-10-31 | 甘肃银达化工有限公司 | 连续制备甲苯二胺的方法 |
CN101671277B (zh) * | 2009-09-18 | 2011-12-28 | 天津大学 | 一种甲苯二异氰酸酯连续生产中热集成的溶剂回收方法 |
JP5711768B2 (ja) * | 2010-03-18 | 2015-05-07 | ハンツマン・インターナショナル・エルエルシー | 芳香族ニトロ化合物からアミンへの転化方法 |
JP5883661B2 (ja) * | 2012-01-25 | 2016-03-15 | 旭化成ケミカルズ株式会社 | N−置換カルバミン酸エステルの製造方法 |
HUE054424T2 (hu) | 2017-01-27 | 2021-09-28 | Covestro Llc | Eljárás stabil toluol-diamin származék/víz elegyek elõállítására, kapcsolódó készítmények, és az elegyek üzemanyagként történõ alkalmazásának eljárásai |
CN110105248B (zh) * | 2019-05-31 | 2021-07-20 | 上海应用技术大学 | 一种甲苯二异氰酸酯的制备方法 |
EP4151619A1 (en) | 2021-09-20 | 2023-03-22 | Covestro Deutschland AG | Method for the removal of water from and transport of aliphatic diamines |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2976320A (en) * | 1957-07-30 | 1961-03-21 | Allied Chem | Catalytic hydrogenation of the dinitro derivatives of toluene |
GB895197A (en) * | 1960-11-25 | 1962-05-02 | Gen Aniline & Film Corp | Catalytic reduction of aromatic dinitro compounds |
GB1164519A (en) * | 1966-07-19 | 1969-09-17 | Inst Chemii Ogolnej | Method for preparing Toluylenediisocyanates from Dinitrotoluenes |
US4224249A (en) * | 1979-05-14 | 1980-09-23 | Air Products And Chemicals, Inc. | Toluene diamine from non-washed dinitrotoluene |
US4717774A (en) * | 1985-12-20 | 1988-01-05 | Basf Corporation | Process for the preparation of toluene diamines |
DE4230098C1 (zh) * | 1992-09-09 | 1993-06-03 | Bayer Ag, 5090 Leverkusen, De | |
US5449832A (en) * | 1994-10-05 | 1995-09-12 | Air Products And Chemicals, Inc. | Process for storage and transport of toluenediamine |
US5714634A (en) * | 1996-06-25 | 1998-02-03 | Air Products And Chemicals, Inc. | Process for storage and transport of toluenediamine |
US5693862A (en) * | 1996-12-18 | 1997-12-02 | Arco Chemical Technology, L.P. | Process for transport of toluenediamine |
-
1995
- 1995-08-04 DE DE19528781A patent/DE19528781A1/de not_active Withdrawn
-
1996
- 1996-07-23 DE DE59609285T patent/DE59609285D1/de not_active Expired - Lifetime
- 1996-07-23 PT PT96111809T patent/PT757034E/pt unknown
- 1996-07-23 ES ES96111809T patent/ES2176380T3/es not_active Expired - Lifetime
- 1996-07-23 EP EP01100055A patent/EP1090906A1/de not_active Ceased
- 1996-07-23 EP EP96111809A patent/EP0757034B1/de not_active Expired - Lifetime
- 1996-07-31 JP JP21690096A patent/JP4095685B2/ja not_active Expired - Lifetime
- 1996-08-01 US US08/691,222 patent/US5849947A/en not_active Expired - Lifetime
- 1996-08-02 CN CNB001317962A patent/CN1163470C/zh not_active Expired - Lifetime
- 1996-08-02 CA CA002182654A patent/CA2182654A1/en not_active Abandoned
- 1996-08-02 CN CN96111631A patent/CN1070474C/zh not_active Expired - Lifetime
- 1996-08-02 UA UA96083118A patent/UA47399C2/uk unknown
- 1996-08-02 PL PL96315490A patent/PL184186B1/pl not_active IP Right Cessation
- 1996-08-02 CZ CZ19962299A patent/CZ292604B6/cs not_active IP Right Cessation
- 1996-08-02 RU RU96115368/04A patent/RU2202537C2/ru active
- 1996-08-02 TW TW85109303A patent/TW374080B/zh not_active IP Right Cessation
- 1996-08-03 KR KR1019960032490A patent/KR100453862B1/ko not_active IP Right Cessation
- 1996-08-05 BR BR9603278A patent/BR9603278A/pt not_active Application Discontinuation
-
1998
- 1998-09-08 US US09/149,379 patent/US6472564B1/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CN1070474C (zh) | 2001-09-05 |
KR100453862B1 (ko) | 2005-04-08 |
DE19528781A1 (de) | 1997-02-06 |
CN1149579A (zh) | 1997-05-14 |
JP4095685B2 (ja) | 2008-06-04 |
EP1090906A1 (de) | 2001-04-11 |
US5849947A (en) | 1998-12-15 |
CN1163470C (zh) | 2004-08-25 |
MX195147B (zh) | 2000-01-31 |
DE59609285D1 (de) | 2002-07-11 |
CZ229996A3 (en) | 1997-02-12 |
JPH0952873A (ja) | 1997-02-25 |
ES2176380T3 (es) | 2002-12-01 |
MX9603167A (es) | 1997-07-31 |
EP0757034B1 (de) | 2002-06-05 |
US6472564B1 (en) | 2002-10-29 |
PT757034E (pt) | 2002-09-30 |
PL315490A1 (en) | 1997-02-17 |
UA47399C2 (uk) | 2002-07-15 |
CZ292604B6 (cs) | 2003-11-12 |
CA2182654A1 (en) | 1997-02-05 |
EP0757034A1 (de) | 1997-02-05 |
KR970010735A (ko) | 1997-03-27 |
BR9603278A (pt) | 1998-05-12 |
PL184186B1 (pl) | 2002-09-30 |
RU2202537C2 (ru) | 2003-04-20 |
TW374080B (zh) | 1999-11-11 |
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