DE2736862A1 - Verfahren zur hestellung von polyaminen der diphenylmethanreihe - Google Patents
Verfahren zur hestellung von polyaminen der diphenylmethanreiheInfo
- Publication number
- DE2736862A1 DE2736862A1 DE19772736862 DE2736862A DE2736862A1 DE 2736862 A1 DE2736862 A1 DE 2736862A1 DE 19772736862 DE19772736862 DE 19772736862 DE 2736862 A DE2736862 A DE 2736862A DE 2736862 A1 DE2736862 A1 DE 2736862A1
- Authority
- DE
- Germany
- Prior art keywords
- water
- divinylbenzene
- weight
- reaction
- isomers
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims description 20
- 229920000768 polyamine Polymers 0.000 title claims description 20
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 title claims description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 52
- 239000003054 catalyst Substances 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 22
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 229920001577 copolymer Polymers 0.000 claims description 16
- 230000002378 acidificating effect Effects 0.000 claims description 10
- 238000009833 condensation Methods 0.000 claims description 10
- 230000005494 condensation Effects 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 150000003142 primary aromatic amines Chemical class 0.000 claims description 2
- 150000003336 secondary aromatic amines Chemical class 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 20
- 150000002500 ions Chemical class 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 150000004982 aromatic amines Chemical class 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- UTNMPUFESIRPQP-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1N UTNMPUFESIRPQP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-UHFFFAOYSA-N 0.000 description 2
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- -1 anilines Arylamines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical group CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 1
- DWOBGCPUQNFAFB-UHFFFAOYSA-N 2-benzylaniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1 DWOBGCPUQNFAFB-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- CDEGDZUMZIYNRD-UHFFFAOYSA-N 2-cyclohexylaniline Chemical compound NC1=CC=CC=C1C1CCCCC1 CDEGDZUMZIYNRD-UHFFFAOYSA-N 0.000 description 1
- MKARNSWMMBGSHX-UHFFFAOYSA-N 3,5-dimethylaniline Chemical group CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- CCYIDDLFQHLCGA-UHFFFAOYSA-N n-methyl-n-phenylthiohydroxylamine Chemical compound CN(S)C1=CC=CC=C1 CCYIDDLFQHLCGA-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006277 sulfonation reaction 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772736862 DE2736862A1 (de) | 1977-08-16 | 1977-08-16 | Verfahren zur hestellung von polyaminen der diphenylmethanreihe |
| EP78100591A EP0000778B1 (fr) | 1977-08-16 | 1978-08-04 | Procédé pour la préparation de polyamines de la série des diphénylméthanes |
| DE7878100591T DE2860072D1 (en) | 1977-08-16 | 1978-08-04 | Process for the preparation of polyamines of the diphenyl methane series |
| ES472514A ES472514A1 (es) | 1977-08-16 | 1978-08-11 | Procedimiento para la obtencion de poliamidas |
| IT50728/78A IT1106878B (it) | 1977-08-16 | 1978-08-11 | Procedimento per produrre poliammine della serie del difenilmetano |
| JP9828478A JPS5432461A (en) | 1977-08-16 | 1978-08-14 | Production of polyamine of diphenymethane system |
| BR7805250A BR7805250A (pt) | 1977-08-16 | 1978-08-15 | Processo para a preparacao de poliaminas da serie do difenilmetano |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772736862 DE2736862A1 (de) | 1977-08-16 | 1977-08-16 | Verfahren zur hestellung von polyaminen der diphenylmethanreihe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2736862A1 true DE2736862A1 (de) | 1979-03-01 |
Family
ID=6016494
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772736862 Withdrawn DE2736862A1 (de) | 1977-08-16 | 1977-08-16 | Verfahren zur hestellung von polyaminen der diphenylmethanreihe |
| DE7878100591T Expired DE2860072D1 (en) | 1977-08-16 | 1978-08-04 | Process for the preparation of polyamines of the diphenyl methane series |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE7878100591T Expired DE2860072D1 (en) | 1977-08-16 | 1978-08-04 | Process for the preparation of polyamines of the diphenyl methane series |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0000778B1 (fr) |
| JP (1) | JPS5432461A (fr) |
| BR (1) | BR7805250A (fr) |
| DE (2) | DE2736862A1 (fr) |
| ES (1) | ES472514A1 (fr) |
| IT (1) | IT1106878B (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3026554A1 (de) * | 1980-07-12 | 1982-02-11 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von polyamingemischen mit einem hohen anteil an 4,4'-diaminodiphenylmethan |
| DE3142529A1 (de) * | 1981-10-27 | 1983-05-05 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Verfahren zur herstellung von diaminen der diphenylmethanreihe |
| WO2009129286A1 (fr) * | 2008-04-16 | 2009-10-22 | Dow Global Technologies Inc. | Procédé pour la production de méthane à base de polyaminopolyphényle utilisant un système catalyseur d’acide solide mixte |
| DE102008001469A1 (de) * | 2008-04-30 | 2009-11-05 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Diaminodiphenylalkanen |
| DE102008001492A1 (de) * | 2008-04-30 | 2009-11-05 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Diaminodiphenylalkanen |
| DE102008002002A1 (de) | 2008-05-27 | 2009-12-03 | Evonik Degussa Gmbh | Chlor armes mehrstufiges Verfahren zur Herstellung von cycloaliphatischen Diisocyanaten |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1179945B (de) * | 1962-12-11 | 1964-10-22 | Basf Ag | Verfahren zur Herstellung von 4, 4'-Diaminodiphenylmethanen |
| US3367969A (en) * | 1965-03-08 | 1968-02-06 | Du Pont | Process for the preparation of 4, 4'-methylenedianiline |
| BE754023A (fr) * | 1969-07-31 | 1971-01-28 | Kaiser Aluminium Chem Corp | Procede pour la fabrication de polyamines |
| DD109615A1 (fr) * | 1972-08-14 | 1974-11-12 | ||
| US3971829A (en) * | 1974-11-18 | 1976-07-27 | Jefferson Chemical Company, Inc. | Preparation of methylene-bridged polyphenylpolyamine mixtures |
| DE2748968A1 (de) * | 1976-11-06 | 1978-05-11 | Elprochine Ag | Verfahren zur herstellung von methylenbruecken aufweisenden polyarylaminen |
-
1977
- 1977-08-16 DE DE19772736862 patent/DE2736862A1/de not_active Withdrawn
-
1978
- 1978-08-04 EP EP78100591A patent/EP0000778B1/fr not_active Expired
- 1978-08-04 DE DE7878100591T patent/DE2860072D1/de not_active Expired
- 1978-08-11 ES ES472514A patent/ES472514A1/es not_active Expired
- 1978-08-11 IT IT50728/78A patent/IT1106878B/it active
- 1978-08-14 JP JP9828478A patent/JPS5432461A/ja active Pending
- 1978-08-15 BR BR7805250A patent/BR7805250A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES472514A1 (es) | 1979-02-16 |
| EP0000778B1 (fr) | 1980-07-23 |
| BR7805250A (pt) | 1979-04-24 |
| IT7850728A0 (it) | 1978-08-11 |
| JPS5432461A (en) | 1979-03-09 |
| IT1106878B (it) | 1985-11-18 |
| EP0000778A1 (fr) | 1979-02-21 |
| DE2860072D1 (en) | 1980-11-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |