DE19528781A1 - Verfahren zur Herstellung von Toluylendiisocyanat, spezielle Gemische aus Toluylendiamin und Wasser und deren Verwendung zur Herstellung von Toluylendiisocyanat - Google Patents
Verfahren zur Herstellung von Toluylendiisocyanat, spezielle Gemische aus Toluylendiamin und Wasser und deren Verwendung zur Herstellung von ToluylendiisocyanatInfo
- Publication number
- DE19528781A1 DE19528781A1 DE19528781A DE19528781A DE19528781A1 DE 19528781 A1 DE19528781 A1 DE 19528781A1 DE 19528781 A DE19528781 A DE 19528781A DE 19528781 A DE19528781 A DE 19528781A DE 19528781 A1 DE19528781 A1 DE 19528781A1
- Authority
- DE
- Germany
- Prior art keywords
- water
- tda
- toluenediamine
- weight
- mixtures
- 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.)
- Withdrawn
Links
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 title claims description 100
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 73
- 239000000203 mixture Substances 0.000 title claims description 40
- 238000000034 method Methods 0.000 title claims description 31
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 34
- DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 claims description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- 239000000243 solution Substances 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000003085 diluting agent Substances 0.000 claims description 12
- 238000000926 separation method Methods 0.000 claims description 10
- 238000007711 solidification Methods 0.000 claims description 9
- 230000008023 solidification Effects 0.000 claims description 9
- 238000010626 work up procedure Methods 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 6
- 239000012045 crude solution Substances 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 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 4
- 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 4
- 230000008014 freezing Effects 0.000 claims description 3
- 238000007710 freezing Methods 0.000 claims description 3
- 230000000802 nitrating effect Effects 0.000 claims description 3
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 16
- 238000004821 distillation Methods 0.000 description 14
- 230000032258 transport Effects 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000004998 toluenediamines Chemical class 0.000 description 3
- 125000005628 tolylene group Chemical group 0.000 description 3
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 239000000498 cooling water Substances 0.000 description 2
- 230000017525 heat dissipation Effects 0.000 description 2
- 239000012943 hotmelt Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000001840 Dandruff Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000002920 hazardous waste Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement 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
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000004056 waste incineration Methods 0.000 description 1
- 239000002351 wastewater 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)
Priority Applications (20)
| 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 |
| PT96111809T PT757034E (pt) | 1995-08-04 | 1996-07-23 | Processo para a preparacao de toluenodi-isocianato misturas especiais de toluenodiamina e agua e sua utilizacao na preparacao de toluenodi-isocianato |
| EP96111809A EP0757034B1 (de) | 1995-08-04 | 1996-07-23 | Verfahren zur Herstellung von Toluylendiisocyanat |
| EP01100055A EP1090906A1 (de) | 1995-08-04 | 1996-07-23 | Gemische aus Toluylendiamin und Wasser |
| DE59609285T DE59609285D1 (de) | 1995-08-04 | 1996-07-23 | Verfahren zur Herstellung von Toluylendiisocyanat |
| ES96111809T ES2176380T3 (es) | 1995-08-04 | 1996-07-23 | Procedimiento para preparar toluilendiisocianato. |
| JP21690096A JP4095685B2 (ja) | 1995-08-04 | 1996-07-31 | トルイレンジイソシアネートの製造方法、トルイレンジアミンと水の特定の混合物、及びトルイレンジイソシアネートを製造するための混合物の使用 |
| US08/691,222 US5849947A (en) | 1995-08-04 | 1996-08-01 | Process for the preparation of toluylene diisocyanate, specific mixtures of toluylene diamine and water, and the use of toluylene diamine and water mixtures to prepare toluylene diisocyanate |
| CNB001317962A 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 |
| CA002182654A CA2182654A1 (en) | 1995-08-04 | 1996-08-02 | Process for the preparation of toluylene diisocyanate, specific mixtures of toluylene diamine and water, and the use of mixtures to prepare toluylene diisocyanate |
| TW85109303A TW374080B (enExample) | 1995-08-04 | 1996-08-02 | |
| PL96315490A PL184186B1 (pl) | 1995-08-04 | 1996-08-02 | Sposób wytwarzania dwuizocyjanianu toluilenu, kompozycja toluilenodwuaminy i wody |
| UA96083118A UA47399C2 (uk) | 1995-08-04 | 1996-08-02 | Толуїлендіамін, що містить воду |
| RU96115368/04A RU2202537C2 (ru) | 1995-08-04 | 1996-08-02 | Водосодержащий толуилендиамин, пригодный для хранения или транспортировки в жидком виде, способ его получения и способ получения толуилендиизоцианата |
| CN96111631A 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 |
| MXPA/A/1996/003167A MXPA96003167A (en) | 1995-08-04 | 1996-08-02 | A process to prepare toluylendiisocyanate, toluylendiamines and water specific mixtures, and mixtures use to prepare toluylendiisocyanate |
| CZ19962299A CZ292604B6 (cs) | 1995-08-04 | 1996-08-02 | Způsob výroby toluendiisokyanátu |
| KR1019960032490A KR100453862B1 (ko) | 1995-08-04 | 1996-08-03 | 톨루일렌디이소시아네이트의제조방법,톨루일렌디아민과물의특정혼합물및톨루일렌디이소시아네이트제조를위한혼합물의용도 |
| BR9603278A BR9603278A (pt) | 1995-08-04 | 1996-08-05 | Processo para a preparação de diisocianato de toluileno misturas específicas de diamina de toluileno e água e uso de misturas para a preparação de diisociananto de toluileno |
| US09/149,379 US6472564B1 (en) | 1995-08-04 | 1998-09-08 | Process for the preparation of toluylene diisocyanate, specific mixtures of toluylene diamine and water, and the use of toluylene diamine and water mixtures to prepare toluylene diisocyanate |
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 |
|---|---|
| DE19528781A1 true DE19528781A1 (de) | 1997-02-06 |
Family
ID=7768754
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19528781A Withdrawn 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 |
| DE59609285T Expired - Lifetime DE59609285D1 (de) | 1995-08-04 | 1996-07-23 | Verfahren zur Herstellung von Toluylendiisocyanat |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59609285T Expired - Lifetime DE59609285D1 (de) | 1995-08-04 | 1996-07-23 | Verfahren zur Herstellung von Toluylendiisocyanat |
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 |
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| 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 |
| 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 |
| UA47399C2 (uk) | 2002-07-15 |
| 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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