DE60213393T2 - Verfahren zur herstellung von mischungen aus diaminodiphenylmethan und seinen höheren homologen mit einer kontrollierten isomerenverteilung - Google Patents
Verfahren zur herstellung von mischungen aus diaminodiphenylmethan und seinen höheren homologen mit einer kontrollierten isomerenverteilung Download PDFInfo
- Publication number
- DE60213393T2 DE60213393T2 DE60213393T DE60213393T DE60213393T2 DE 60213393 T2 DE60213393 T2 DE 60213393T2 DE 60213393 T DE60213393 T DE 60213393T DE 60213393 T DE60213393 T DE 60213393T DE 60213393 T2 DE60213393 T2 DE 60213393T2
- Authority
- DE
- Germany
- Prior art keywords
- zeolite
- reaction
- aniline
- solvent
- formaldehyde
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 238000009826 distribution Methods 0.000 title abstract description 10
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 title description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 104
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 125000006546 (C4-C10) cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 239000010457 zeolite Substances 0.000 claims description 107
- 229910021536 Zeolite Inorganic materials 0.000 claims description 98
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 93
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 79
- 238000000034 method Methods 0.000 claims description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 239000002904 solvent Substances 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 239000003054 catalyst Substances 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 27
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 16
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 15
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 11
- 239000004327 boric acid Substances 0.000 claims description 11
- 238000006462 rearrangement reaction Methods 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 238000001354 calcination Methods 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 7
- 229910052796 boron Inorganic materials 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 230000004048 modification Effects 0.000 claims description 7
- 238000012986 modification Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000002243 precursor Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 150000001448 anilines Chemical class 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 150000004985 diamines Chemical class 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
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 229910017090 AlO 2 Inorganic materials 0.000 claims description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 229910052742 iron 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
- 238000011068 loading method Methods 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 2
- 239000003849 aromatic solvent Substances 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 229910019655 synthetic inorganic crystalline material Inorganic materials 0.000 claims 1
- -1 methane diphenyl diamine Chemical class 0.000 abstract description 5
- 235000010290 biphenyl Nutrition 0.000 abstract 2
- 239000004305 biphenyl Substances 0.000 abstract 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 2
- 239000000463 material Substances 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 20
- 239000011521 glass Substances 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- 238000004821 distillation Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- 239000000725 suspension Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 239000007795 chemical reaction product Substances 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- 239000007810 chemical reaction solvent Substances 0.000 description 11
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- 239000013638 trimer Substances 0.000 description 11
- 238000006555 catalytic reaction Methods 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 238000000926 separation method Methods 0.000 description 7
- 230000003197 catalytic effect Effects 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 150000003863 ammonium salts Chemical class 0.000 description 5
- 229910001593 boehmite Inorganic materials 0.000 description 5
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
- 239000005695 Ammonium acetate Substances 0.000 description 4
- 229940043376 ammonium acetate Drugs 0.000 description 4
- 235000019257 ammonium acetate Nutrition 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 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 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 150000007513 acids Chemical class 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
- 150000003939 benzylamines Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 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
- 238000002485 combustion reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 239000007862 dimeric product Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- 239000000126 substance Substances 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
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- 206010061307 Neck deformity Diseases 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004090 dissolution 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
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 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
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012229 microporous material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 238000005406 washing 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
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/90—Stabilisation; Use of additives
-
- 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
- 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
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2001MI000880A ITMI20010880A1 (it) | 2001-04-27 | 2001-04-27 | Procedimento per la produzione di metilendianilina mediante catalizzatori zeolitici modificati |
| ITMI20010880 | 2001-04-27 | ||
| PCT/EP2002/004714 WO2002088067A1 (en) | 2001-04-27 | 2002-04-29 | Process for the synthesis of mixtures of methane diphenyl diamine and its higher homologues with a controlled isomer distribution |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60213393D1 DE60213393D1 (de) | 2006-09-07 |
| DE60213393T2 true DE60213393T2 (de) | 2006-11-23 |
Family
ID=11447559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60213393T Expired - Lifetime DE60213393T2 (de) | 2001-04-27 | 2002-04-29 | Verfahren zur herstellung von mischungen aus diaminodiphenylmethan und seinen höheren homologen mit einer kontrollierten isomerenverteilung |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7105700B2 (enExample) |
| EP (1) | EP1381589B1 (enExample) |
| JP (1) | JP4279560B2 (enExample) |
| KR (1) | KR100874120B1 (enExample) |
| CN (1) | CN1266114C (enExample) |
| AT (1) | ATE334113T1 (enExample) |
| BR (1) | BR0209344A (enExample) |
| DE (1) | DE60213393T2 (enExample) |
| IT (1) | ITMI20010880A1 (enExample) |
| WO (1) | WO2002088067A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008012037A1 (de) | 2008-03-01 | 2009-09-03 | Bayer Materialscience Ag | Verfahren zur Herstellung von Methylen-diphenyl-diisocyanaten |
| KR20170031157A (ko) | 2014-07-07 | 2017-03-20 | 코베스트로 도이칠란트 아게 | 디페닐메탄 시리즈의 디아민 및 폴리아민의 제조 방법 |
| CN107501524B (zh) * | 2017-08-30 | 2020-05-12 | 本源精化环保科技有限公司 | N,n’烷基化二氨基二苯基甲烷类固化剂及制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4071558A (en) * | 1967-09-28 | 1978-01-31 | Texaco Development Corporation | Aromatic polyamines and their preparation |
| DE3783199T2 (de) * | 1986-10-22 | 1993-04-29 | Enichem Sintesi | Verfahren zur herstellung von 4,4' diaminodiphenylmethan und derivaten davon. |
| TW325461B (en) * | 1995-09-11 | 1998-01-21 | Air Prod & Chem | Ammoxidation of alkanes and alkenes |
| DE19724237A1 (de) * | 1997-06-09 | 1998-12-10 | Basf Ag | Verfahren zur Herstellung von aromatischen Polyamingemischen |
| IT1312331B1 (it) * | 1999-05-27 | 2002-04-15 | Enichem Spa | Procedimento per la produzione di diamminodifenilmetano e suoiomologhi superiori. |
-
2001
- 2001-04-27 IT IT2001MI000880A patent/ITMI20010880A1/it unknown
-
2002
- 2002-04-29 KR KR1020037014071A patent/KR100874120B1/ko not_active Expired - Fee Related
- 2002-04-29 WO PCT/EP2002/004714 patent/WO2002088067A1/en not_active Ceased
- 2002-04-29 AT AT02745272T patent/ATE334113T1/de not_active IP Right Cessation
- 2002-04-29 US US10/476,955 patent/US7105700B2/en not_active Expired - Lifetime
- 2002-04-29 EP EP02745272A patent/EP1381589B1/en not_active Expired - Lifetime
- 2002-04-29 JP JP2002585371A patent/JP4279560B2/ja not_active Expired - Lifetime
- 2002-04-29 BR BR0209344-8A patent/BR0209344A/pt not_active IP Right Cessation
- 2002-04-29 CN CNB028089820A patent/CN1266114C/zh not_active Expired - Fee Related
- 2002-04-29 DE DE60213393T patent/DE60213393T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR100874120B1 (ko) | 2008-12-15 |
| US7105700B2 (en) | 2006-09-12 |
| BR0209344A (pt) | 2004-06-15 |
| US20040181092A1 (en) | 2004-09-16 |
| EP1381589B1 (en) | 2006-07-26 |
| ITMI20010880A0 (it) | 2001-04-27 |
| EP1381589A1 (en) | 2004-01-21 |
| CN1266114C (zh) | 2006-07-26 |
| JP4279560B2 (ja) | 2009-06-17 |
| JP2004532232A (ja) | 2004-10-21 |
| WO2002088067A1 (en) | 2002-11-07 |
| ATE334113T1 (de) | 2006-08-15 |
| KR20040016857A (ko) | 2004-02-25 |
| ITMI20010880A1 (it) | 2002-10-27 |
| CN1505605A (zh) | 2004-06-16 |
| DE60213393D1 (de) | 2006-09-07 |
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