UA47399C2 - Толуїлендіамін, що містить воду - Google Patents
Толуїлендіамін, що містить воду Download PDFInfo
- Publication number
- UA47399C2 UA47399C2 UA96083118A UA96083118A UA47399C2 UA 47399 C2 UA47399 C2 UA 47399C2 UA 96083118 A UA96083118 A UA 96083118A UA 96083118 A UA96083118 A UA 96083118A UA 47399 C2 UA47399 C2 UA 47399C2
- Authority
- UA
- Ukraine
- Prior art keywords
- water
- toluenediamine
- fact
- pressure
- column
- Prior art date
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 239000000203 mixture Substances 0.000 claims abstract description 16
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 50
- 238000004519 manufacturing process Methods 0.000 claims description 17
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims description 4
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 238000012876 topography Methods 0.000 claims 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 18
- 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 16
- 238000000034 method Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 206010062717 Increased upper airway secretion Diseases 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 208000026435 phlegm Diseases 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000009434 installation Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- JLEQUYOQVZXFFW-UHFFFAOYSA-N 2-chlorobenzoate;dimethylazanium Chemical compound C[NH2+]C.[O-]C(=O)C1=CC=CC=C1Cl JLEQUYOQVZXFFW-UHFFFAOYSA-N 0.000 description 2
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- -1 for example Substances 0.000 description 2
- 239000012943 hotmelt Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000008520 organization Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000010849 combustible waste Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- 238000012856 packing Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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)
Applications Claiming Priority (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA47399C2 true UA47399C2 (uk) | 2002-07-15 |
Family
ID=7768754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA96083118A UA47399C2 (uk) | 1995-08-04 | 1996-08-02 | Толуїлендіамін, що містить воду |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US5849947A (enExample) |
| EP (2) | EP1090906A1 (enExample) |
| JP (1) | JP4095685B2 (enExample) |
| KR (1) | KR100453862B1 (enExample) |
| CN (2) | CN1070474C (enExample) |
| BR (1) | BR9603278A (enExample) |
| CA (1) | CA2182654A1 (enExample) |
| CZ (1) | CZ292604B6 (enExample) |
| DE (2) | DE19528781A1 (enExample) |
| ES (1) | ES2176380T3 (enExample) |
| PL (1) | PL184186B1 (enExample) |
| PT (1) | PT757034E (enExample) |
| RU (1) | RU2202537C2 (enExample) |
| TW (1) | TW374080B (enExample) |
| UA (1) | UA47399C2 (enExample) |
Families Citing this family (28)
| 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 |
| DE60214195T2 (de) * | 2002-10-22 | 2007-10-04 | Bayer Materialscience Ag | Verfahren zur Reinigung von Diisocyanatotoluol unter Verwendung einer Destillationskolonne mit Trennwand in der Endreinigung |
| DE10260093A1 (de) * | 2002-12-19 | 2004-07-01 | Basf Ag | Verfahren zur Abtrennung von Isocyanaten aus einem Reaktionsgemisch |
| US7897805B2 (en) * | 2005-03-10 | 2011-03-01 | Mitsui Chemicals, Inc. | Polyisocyanate production method and polyisocyanate production system |
| 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 |
| 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 |
| DE102005036870A1 (de) * | 2005-08-02 | 2007-02-08 | Bayer Materialscience Ag | Verfahren zur Gasphasenphosgenierung |
| 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 |
| PL2367783T3 (pl) | 2008-11-19 | 2013-06-28 | Basf Se | Sposób wytwarzania izocyjanianu |
| 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 |
| RU2518110C1 (ru) * | 2010-03-18 | 2014-06-10 | ХАНТСМЭН ИНТЕРНЭШНЛ ЭлЭлСи | Способ преобразования ароматического нитросоединения в амины |
| 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 |
| IL236155B (en) * | 2014-12-09 | 2021-10-31 | List Holding Ag | Chemical production methods and devices for their execution |
| CN110234624B (zh) * | 2017-01-27 | 2023-03-21 | 科思创有限公司 | 稳定甲苯二胺残留物/水共混物的工艺、相关组合物及这类共混物作为燃料的用途 |
| 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 |
| US20230159433A1 (en) * | 2020-05-19 | 2023-05-25 | Covestro Deutschland Ag | Method for preparing toluylene diamine mixtures |
| KR20240012559A (ko) * | 2021-05-25 | 2024-01-29 | 바스프 에스이 | 적어도 1종의 폴리이소시아네이트의 제조 방법 |
| EP4151619A1 (en) | 2021-09-20 | 2023-03-22 | Covestro Deutschland AG | Method for the removal of water from and transport of aliphatic diamines |
| EP4653418A1 (de) | 2024-05-22 | 2025-11-26 | Covestro Deutschland AG | Verfahren zur herstellung von organischem isocyanat mit verbesserter nachhaltigkeit |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB786407A (en) * | 1956-04-30 | 1957-11-20 | Du Pont | Process for the catalytic hydrogenation of organic nitro compounds |
| 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 |
| GB1303562A (enExample) * | 1971-03-12 | 1973-01-17 | ||
| DE2456308A1 (de) * | 1974-11-28 | 1976-08-12 | Bayer Ag | Verfahren zur herstellung von aminoverbindungen |
| 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 (enExample) * | 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 PT PT96111809T patent/PT757034E/pt unknown
- 1996-07-23 DE DE59609285T patent/DE59609285D1/de 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
- 1996-07-23 ES ES96111809T patent/ES2176380T3/es 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 CZ CZ19962299A patent/CZ292604B6/cs not_active IP Right Cessation
- 1996-08-02 RU RU96115368/04A patent/RU2202537C2/ru active
- 1996-08-02 CN CN96111631A patent/CN1070474C/zh not_active Expired - Lifetime
- 1996-08-02 CA CA002182654A patent/CA2182654A1/en not_active Abandoned
- 1996-08-02 TW TW85109303A patent/TW374080B/zh not_active IP Right Cessation
- 1996-08-02 PL PL96315490A patent/PL184186B1/pl not_active IP Right Cessation
- 1996-08-02 UA UA96083118A patent/UA47399C2/uk unknown
- 1996-08-02 CN CNB001317962A patent/CN1163470C/zh not_active Expired - Lifetime
- 1996-08-03 KR KR1019960032490A patent/KR100453862B1/ko not_active Expired - Lifetime
- 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 |
|---|---|
| BR9603278A (pt) | 1998-05-12 |
| KR100453862B1 (ko) | 2005-04-08 |
| EP0757034A1 (de) | 1997-02-05 |
| CZ292604B6 (cs) | 2003-11-12 |
| JPH0952873A (ja) | 1997-02-25 |
| CZ229996A3 (en) | 1997-02-12 |
| CA2182654A1 (en) | 1997-02-05 |
| EP1090906A1 (de) | 2001-04-11 |
| RU2202537C2 (ru) | 2003-04-20 |
| PL315490A1 (en) | 1997-02-17 |
| US6472564B1 (en) | 2002-10-29 |
| EP0757034B1 (de) | 2002-06-05 |
| DE19528781A1 (de) | 1997-02-06 |
| PL184186B1 (pl) | 2002-09-30 |
| US5849947A (en) | 1998-12-15 |
| MX9603167A (es) | 1997-07-31 |
| JP4095685B2 (ja) | 2008-06-04 |
| TW374080B (enExample) | 1999-11-11 |
| CN1332149A (zh) | 2002-01-23 |
| CN1149579A (zh) | 1997-05-14 |
| ES2176380T3 (es) | 2002-12-01 |
| DE59609285D1 (de) | 2002-07-11 |
| CN1070474C (zh) | 2001-09-05 |
| CN1163470C (zh) | 2004-08-25 |
| KR970010735A (ko) | 1997-03-27 |
| PT757034E (pt) | 2002-09-30 |
| MX195147B (enExample) | 2000-01-31 |
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