DE2149998C2 - Verfahren zur Herstellung von aromatischen Polyaminen - Google Patents
Verfahren zur Herstellung von aromatischen PolyaminenInfo
- Publication number
- DE2149998C2 DE2149998C2 DE19712149998 DE2149998A DE2149998C2 DE 2149998 C2 DE2149998 C2 DE 2149998C2 DE 19712149998 DE19712149998 DE 19712149998 DE 2149998 A DE2149998 A DE 2149998A DE 2149998 C2 DE2149998 C2 DE 2149998C2
- Authority
- DE
- Germany
- Prior art keywords
- formaldehyde
- reactor
- mixture
- aromatic
- amine
- 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
Links
- 238000000034 method Methods 0.000 title claims description 30
- 229920000768 polyamine Polymers 0.000 title claims description 16
- 125000003118 aryl group Chemical group 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 74
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 22
- 150000001412 amines Chemical class 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 14
- 150000004982 aromatic amines Chemical class 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000009833 condensation Methods 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 7
- 230000008707 rearrangement Effects 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000004985 diamines Chemical class 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- UTNMPUFESIRPQP-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1N UTNMPUFESIRPQP-UHFFFAOYSA-N 0.000 description 4
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- UPCIBFUJJLCOQG-UHFFFAOYSA-L ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium;dibromide Chemical compound [Br-].[Br-].CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC UPCIBFUJJLCOQG-UHFFFAOYSA-L 0.000 description 4
- 230000017525 heat dissipation Effects 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000000126 substance 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
- HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- -1 B. Methy-IaI Chemical class 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- JDCFAHRSFPYCRN-UHFFFAOYSA-N 2-(2-ethylhexylamino)benzoic acid Chemical compound CCCCC(CC)CNC1=CC=CC=C1C(O)=O JDCFAHRSFPYCRN-UHFFFAOYSA-N 0.000 description 1
- PMAPIPPKZXGDFA-UHFFFAOYSA-N 2-[(2-carboxyanilino)methylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NCNC1=CC=CC=C1C(O)=O PMAPIPPKZXGDFA-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WDTRNCFZFQIWLM-UHFFFAOYSA-N 4-benzylaniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1 WDTRNCFZFQIWLM-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- KLWDPIXDUVYHMS-UHFFFAOYSA-N 4-chloro-n-ethylaniline Chemical compound CCNC1=CC=C(Cl)C=C1 KLWDPIXDUVYHMS-UHFFFAOYSA-N 0.000 description 1
- XCEYKKJMLOFDSS-UHFFFAOYSA-N 4-chloro-n-methylaniline Chemical compound CNC1=CC=C(Cl)C=C1 XCEYKKJMLOFDSS-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QCIFLGSATTWUQJ-UHFFFAOYSA-N n,4-dimethylaniline Chemical compound CNC1=CC=C(C)C=C1 QCIFLGSATTWUQJ-UHFFFAOYSA-N 0.000 description 1
- KTDILAZSFSAPMD-UHFFFAOYSA-N n-(2-chloroethyl)aniline Chemical compound ClCCNC1=CC=CC=C1 KTDILAZSFSAPMD-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE789671D BE789671A (fr) | 1971-10-07 | Procede de preparation de polyamines aromatiques | |
| DE19712149998 DE2149998C2 (de) | 1971-10-07 | 1971-10-07 | Verfahren zur Herstellung von aromatischen Polyaminen |
| AU47327/72A AU467401B2 (en) | 1971-10-07 | 1972-10-03 | Process forthe preparation of aromatic polyamines |
| NL7213433A NL7213433A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-10-07 | 1972-10-04 | |
| GB4588572A GB1365454A (en) | 1971-10-07 | 1972-10-05 | Process for the preparation od aromatic polyamines |
| IT5318372A IT966201B (it) | 1971-10-07 | 1972-10-05 | Procedimento ed impianto per la produzione di poliammine aromatiche |
| JP9998072A JPS4846693A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-10-07 | 1972-10-06 | |
| FR7235578A FR2155657A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-10-07 | 1972-10-06 | |
| BR696572A BR7206965D0 (pt) | 1971-10-07 | 1972-10-06 | Processo para a preparacao de poliaminas aromaticas |
| ES407385A ES407385A1 (es) | 1971-10-07 | 1972-10-06 | Procedimiento para la obtencion de poliaminas aromaticas. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712149998 DE2149998C2 (de) | 1971-10-07 | 1971-10-07 | Verfahren zur Herstellung von aromatischen Polyaminen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2149998A1 DE2149998A1 (de) | 1973-04-12 |
| DE2149998C2 true DE2149998C2 (de) | 1982-05-19 |
Family
ID=5821687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712149998 Expired DE2149998C2 (de) | 1971-10-07 | 1971-10-07 | Verfahren zur Herstellung von aromatischen Polyaminen |
Country Status (10)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1960346B2 (en) | 2005-12-08 | 2019-03-27 | Huntsman International Llc | Process for preparing diaminodiphenylmethanes |
| JP7131558B2 (ja) * | 2017-09-15 | 2022-09-06 | 日産化学株式会社 | ノボラック型ポリマーの製造方法 |
| US11542223B1 (en) | 2022-07-21 | 2023-01-03 | Covestro Llc | Process for preparing di- and polyamines of the diphenyl methane series |
| EP4345088A1 (en) | 2022-09-29 | 2024-04-03 | Covestro Deutschland AG | A process for preparing di- and polyamines of the diphenyl methane series |
| CN118164859B (zh) * | 2024-05-11 | 2024-08-20 | 万华化学集团股份有限公司 | 一种二苯基甲烷系列的二胺和多胺的制备方法 |
-
0
- BE BE789671D patent/BE789671A/xx unknown
-
1971
- 1971-10-07 DE DE19712149998 patent/DE2149998C2/de not_active Expired
-
1972
- 1972-10-03 AU AU47327/72A patent/AU467401B2/en not_active Expired
- 1972-10-04 NL NL7213433A patent/NL7213433A/xx unknown
- 1972-10-05 GB GB4588572A patent/GB1365454A/en not_active Expired
- 1972-10-05 IT IT5318372A patent/IT966201B/it active
- 1972-10-06 JP JP9998072A patent/JPS4846693A/ja active Pending
- 1972-10-06 BR BR696572A patent/BR7206965D0/pt unknown
- 1972-10-06 FR FR7235578A patent/FR2155657A5/fr not_active Expired
- 1972-10-06 ES ES407385A patent/ES407385A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BR7206965D0 (pt) | 1973-10-09 |
| FR2155657A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-05-18 |
| IT966201B (it) | 1974-02-11 |
| NL7213433A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-04-10 |
| AU467401B2 (en) | 1975-11-27 |
| JPS4846693A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-07-03 |
| BE789671A (fr) | 1973-04-04 |
| AU4732772A (en) | 1974-04-11 |
| DE2149998A1 (de) | 1973-04-12 |
| ES407385A1 (es) | 1975-11-01 |
| GB1365454A (en) | 1974-09-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |