PT1355874E - Processo para a síntese de mistura de di(aminofenil)metano com os seus homólogos superiores, com uma distribuição de isómeros controlada - Google Patents
Processo para a síntese de mistura de di(aminofenil)metano com os seus homólogos superiores, com uma distribuição de isómeros controlada Download PDFInfo
- Publication number
- PT1355874E PT1355874E PT01974234T PT01974234T PT1355874E PT 1355874 E PT1355874 E PT 1355874E PT 01974234 T PT01974234 T PT 01974234T PT 01974234 T PT01974234 T PT 01974234T PT 1355874 E PT1355874 E PT 1355874E
- Authority
- PT
- Portugal
- Prior art keywords
- zeolite
- quot
- aniline
- process according
- reaction
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims description 57
- 238000009826 distribution Methods 0.000 title abstract description 10
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title abstract description 6
- -1 methane diphenyl diamine Chemical class 0.000 title abstract description 5
- 235000010290 biphenyl Nutrition 0.000 title abstract 3
- 239000004305 biphenyl Substances 0.000 title abstract 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title abstract 3
- 230000015572 biosynthetic process Effects 0.000 title description 18
- 238000003786 synthesis reaction Methods 0.000 title description 18
- 239000010457 zeolite Substances 0.000 claims abstract description 92
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 83
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 83
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 85
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 60
- 150000001412 amines Chemical class 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 40
- 239000002904 solvent Substances 0.000 claims description 27
- 239000011541 reaction mixture Substances 0.000 claims description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000002444 silanisation Methods 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- 150000003377 silicon compounds Chemical class 0.000 claims description 10
- 230000017105 transposition Effects 0.000 claims description 10
- OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-UHFFFAOYSA-N 0.000 claims description 9
- 229910052681 coesite Inorganic materials 0.000 claims description 8
- 229910052906 cristobalite Inorganic materials 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000000377 silicon dioxide Substances 0.000 claims description 8
- 229910052682 stishovite Inorganic materials 0.000 claims description 8
- 229910052905 tridymite Inorganic materials 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 239000002243 precursor Substances 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 150000001448 anilines Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 238000006317 isomerization reaction Methods 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 235000012239 silicon dioxide Nutrition 0.000 claims description 4
- 125000006546 (C4-C10) cycloalkyl group Chemical group 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229910052680 mordenite Inorganic materials 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000003849 aromatic solvent Substances 0.000 claims 1
- 229940126214 compound 3 Drugs 0.000 claims 1
- 229910019655 synthetic inorganic crystalline material Inorganic materials 0.000 claims 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 37
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 21
- 239000003054 catalyst Substances 0.000 description 18
- 238000004821 distillation Methods 0.000 description 18
- 230000009466 transformation Effects 0.000 description 17
- 239000002245 particle Substances 0.000 description 16
- 239000011521 glass Substances 0.000 description 14
- 239000013638 trimer Substances 0.000 description 13
- 230000003197 catalytic effect Effects 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 12
- 239000007810 chemical reaction solvent Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 8
- 230000009849 deactivation Effects 0.000 description 8
- 229910004298 SiO 2 Inorganic materials 0.000 description 7
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical group CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 7
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 6
- 229910018404 Al2 O3 Inorganic materials 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 229940095070 tetrapropyl orthosilicate Drugs 0.000 description 5
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000013256 coordination polymer Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- OHQOKJPHNPUMLN-UHFFFAOYSA-N n,n'-diphenylmethanediamine Chemical compound C=1C=CC=CC=1NCNC1=CC=CC=C1 OHQOKJPHNPUMLN-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000003939 benzylamines Chemical class 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- 239000007806 chemical reaction intermediate Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 239000007862 dimeric product Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000012229 microporous material Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 150000001343 alkyl silanes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000012022 methylating agents 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
- 150000002894 organic compounds Chemical class 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 238000005292 vacuum distillation Methods 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
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/78—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton from carbonyl compounds, e.g. from formaldehyde, and amines having amino groups bound to carbon atoms of six-membered aromatic rings, with formation of methylene-diarylamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/54—Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2000MI001959A IT1318686B1 (it) | 2000-09-07 | 2000-09-07 | Procedimento per la sintesi di miscele di metilendianilina e suoiomologhi superiori con distribuzione controllata degli isomeri. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT1355874E true PT1355874E (pt) | 2010-05-11 |
Family
ID=11445761
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT01974234T PT1355874E (pt) | 2000-09-07 | 2001-09-07 | Processo para a síntese de mistura de di(aminofenil)metano com os seus homólogos superiores, com uma distribuição de isómeros controlada |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6936737B2 (https=) |
| EP (1) | EP1355874B1 (https=) |
| JP (1) | JP4890727B2 (https=) |
| KR (1) | KR100817008B1 (https=) |
| CN (1) | CN1257148C (https=) |
| AT (1) | ATE464282T1 (https=) |
| AU (1) | AU2001293801A1 (https=) |
| BR (1) | BR0113790A (https=) |
| IT (1) | IT1318686B1 (https=) |
| PT (1) | PT1355874E (https=) |
| WO (1) | WO2002020458A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0912593B1 (pt) * | 2008-08-14 | 2018-01-23 | Dow Global Technologies Llc | "processo para produzir uma metilenodianilina" |
| EP2680965A2 (de) * | 2011-03-03 | 2014-01-08 | Umicore AG & Co. KG | Katalytisch aktives material und katalysator zur selektiven katalytischen reduktion von stickoxiden |
| EP2495032A1 (de) | 2011-03-03 | 2012-09-05 | Umicore Ag & Co. Kg | SCR-Katalysator mit verbesserter Kohlenwasserstoffresistenz |
| HUE037918T2 (hu) | 2014-07-07 | 2018-09-28 | Covestro Deutschland Ag | Eljárás a difenilmetán sorozat di- és poliaminjainak elõállítására |
| US10538480B2 (en) | 2016-06-30 | 2020-01-21 | Covestro Deutschland Ag | Process for the production of di- and polyamines of the diphenylmethane series |
| WO2025086031A1 (zh) * | 2023-10-23 | 2025-05-01 | 万华化学集团股份有限公司 | 一种二苯基甲烷系列二胺和多胺的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3442795A (en) * | 1963-02-27 | 1969-05-06 | Mobil Oil Corp | Method for preparing highly siliceous zeolite-type materials and materials resulting therefrom |
| US3728408A (en) * | 1969-05-05 | 1973-04-17 | Mobil Oil Corp | Conversion of polar compounds using highly siliceous zeolite-type catalysts |
| US4039581A (en) * | 1975-06-27 | 1977-08-02 | The Upjohn Company | Process for the preparation of di(amino phenyl)methanes |
| US4039580A (en) * | 1975-07-24 | 1977-08-02 | The Upjohn Company | Process for preparing di(aminophenyl)methanes |
| US4294987A (en) * | 1979-12-31 | 1981-10-13 | The Upjohn Company | Process for preparing methylene dianilines |
| US5241119A (en) * | 1986-10-22 | 1993-08-31 | Eniricerche S.P.A. | Process for the preparation of 4,4'-diaminodiphenyl-methane and its derivatives |
| EP0264744B1 (en) * | 1986-10-22 | 1992-12-23 | ENIRICERCHE S.p.A. | Process for the preparation of 4,4'-diaminodiphenylmethane and its derivatives |
| EP0329367A3 (en) * | 1988-02-15 | 1990-10-31 | Mitsui Petrochemical Industries, Ltd. | Method of preparing 4,4'-methylenedianiline |
| IT1312331B1 (it) * | 1999-05-27 | 2002-04-15 | Enichem Spa | Procedimento per la produzione di diamminodifenilmetano e suoiomologhi superiori. |
-
2000
- 2000-09-07 IT IT2000MI001959A patent/IT1318686B1/it active
-
2001
- 2001-09-07 WO PCT/EP2001/010369 patent/WO2002020458A1/en not_active Ceased
- 2001-09-07 KR KR1020037003323A patent/KR100817008B1/ko not_active Expired - Fee Related
- 2001-09-07 AU AU2001293801A patent/AU2001293801A1/en not_active Abandoned
- 2001-09-07 BR BR0113790-5A patent/BR0113790A/pt not_active Application Discontinuation
- 2001-09-07 JP JP2002525083A patent/JP4890727B2/ja not_active Expired - Fee Related
- 2001-09-07 PT PT01974234T patent/PT1355874E/pt unknown
- 2001-09-07 US US10/363,881 patent/US6936737B2/en not_active Expired - Fee Related
- 2001-09-07 AT AT01974234T patent/ATE464282T1/de not_active IP Right Cessation
- 2001-09-07 EP EP01974234A patent/EP1355874B1/en not_active Expired - Lifetime
- 2001-09-07 CN CNB018152147A patent/CN1257148C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE464282T1 (de) | 2010-04-15 |
| ITMI20001959A1 (it) | 2002-03-07 |
| KR100817008B1 (ko) | 2008-03-27 |
| JP4890727B2 (ja) | 2012-03-07 |
| US6936737B2 (en) | 2005-08-30 |
| CN1620418A (zh) | 2005-05-25 |
| ITMI20001959A0 (it) | 2000-09-07 |
| IT1318686B1 (it) | 2003-08-27 |
| BR0113790A (pt) | 2003-07-15 |
| WO2002020458A1 (en) | 2002-03-14 |
| AU2001293801A1 (en) | 2002-03-22 |
| EP1355874A1 (en) | 2003-10-29 |
| JP2004513086A (ja) | 2004-04-30 |
| CN1257148C (zh) | 2006-05-24 |
| EP1355874B1 (en) | 2010-04-14 |
| KR20030090597A (ko) | 2003-11-28 |
| US20040029971A1 (en) | 2004-02-12 |
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