CA1137514A - Process for the preparation of polyamines of the diphenyl methane series which are rich in ortho isomers - Google Patents
Process for the preparation of polyamines of the diphenyl methane series which are rich in ortho isomersInfo
- Publication number
- CA1137514A CA1137514A CA000319238A CA319238A CA1137514A CA 1137514 A CA1137514 A CA 1137514A CA 000319238 A CA000319238 A CA 000319238A CA 319238 A CA319238 A CA 319238A CA 1137514 A CA1137514 A CA 1137514A
- Authority
- CA
- Canada
- Prior art keywords
- aromatic amine
- total quantity
- strong acids
- temperature
- acid
- 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 abstract description 44
- 229920000768 polyamine Polymers 0.000 title claims abstract description 14
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 71
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 58
- 239000002253 acid Substances 0.000 claims abstract description 38
- 150000007513 acids Chemical class 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- -1 aromatic amine salts Chemical class 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 239000008098 formaldehyde solution Substances 0.000 claims abstract description 7
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 6
- 239000000376 reactant Substances 0.000 claims abstract description 6
- 230000008707 rearrangement Effects 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 239000011833 salt mixture Substances 0.000 claims abstract description 5
- 150000003141 primary amines Chemical group 0.000 claims abstract description 4
- 159000000032 aromatic acids Chemical class 0.000 claims abstract description 3
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 3
- 229960004279 formaldehyde Drugs 0.000 claims description 21
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 235000019256 formaldehyde Nutrition 0.000 claims description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 5
- 238000006462 rearrangement reaction Methods 0.000 claims description 4
- 150000001448 anilines Chemical class 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 150000007854 aminals Chemical class 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 8
- 229960000443 hydrochloric acid Drugs 0.000 description 8
- 235000011167 hydrochloric acid Nutrition 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 5
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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
- 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
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N ortho-methyl aniline Natural products CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 230000005588 protonation Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 1
- UTNMPUFESIRPQP-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1N UTNMPUFESIRPQP-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
- WEZAHYDFZNTGKE-UHFFFAOYSA-N 3-ethoxyaniline Chemical compound CCOC1=CC=CC(N)=C1 WEZAHYDFZNTGKE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical class C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2803126 | 1978-01-25 | ||
| DEP2803126.7 | 1978-01-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1137514A true CA1137514A (en) | 1982-12-14 |
Family
ID=6030323
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000319238A Expired CA1137514A (en) | 1978-01-25 | 1979-01-08 | Process for the preparation of polyamines of the diphenyl methane series which are rich in ortho isomers |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0003303B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS54117429A (enrdf_load_stackoverflow) |
| BR (1) | BR7900430A (enrdf_load_stackoverflow) |
| CA (1) | CA1137514A (enrdf_load_stackoverflow) |
| DE (1) | DE2960014D1 (enrdf_load_stackoverflow) |
| ES (1) | ES477114A1 (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7038002B2 (en) | 2003-07-25 | 2006-05-02 | Bayer Materialscience Ag | Production of mixtures of diisocyanates and polyisocyanates from the diphenylmethane series with high contents of 4,4′-methylenediphenyl diisocyanate and 2,4′-methylenediphenyl diisocyanate |
| US7495124B2 (en) | 2004-02-04 | 2009-02-24 | Bayer Materialscience Ag | Process for the production of very pure 2,4′-methylenediphenyl diisocyanate |
| US8557949B2 (en) | 2007-09-19 | 2013-10-15 | Huntsman International Llc | Process for production of di- and polyamines of the diphenylmethane series |
| US9217054B2 (en) | 2007-09-19 | 2015-12-22 | Huntsman International Llc | Process for production of di- and polyamines of the diphenylmethane series |
| CN115745809A (zh) * | 2022-11-17 | 2023-03-07 | 万华化学集团股份有限公司 | 一种低杂质含量低副产品量的二苯基甲烷系列的二胺和多胺的制备方法 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4259526A (en) * | 1979-02-21 | 1981-03-31 | Bayer Aktiengesellschaft | Process for the preparation of mixtures of polyamines of the polyamino-polyaryl-polymethylene type |
| DE2947531A1 (de) * | 1979-11-26 | 1981-06-04 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von polyphenylpolymethylenpolyaminen |
| DE3407494A1 (de) * | 1984-03-01 | 1985-09-05 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von polyaminen und ihre verwendung zur herstellung von polyisocyanaten |
| DE10111337A1 (de) * | 2001-03-08 | 2002-09-12 | Basf Ag | Verfahren zur Herstellung von MDI, insbesondere von 2.4'-MDI |
| JP5231241B2 (ja) | 2005-12-08 | 2013-07-10 | ハンツマン・インターナショナル・エルエルシー | ジアミノジフェニルメタン類の製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3297759A (en) * | 1964-01-13 | 1967-01-10 | Upjohn Co | Continuous process for producing mixtures of methylene-bridged polyphenyl polyamines |
| US3676497A (en) * | 1968-08-06 | 1972-07-11 | Upjohn Co | Process for preparing di(aminophenyl)-methanes |
| JPS5038095B2 (enrdf_load_stackoverflow) * | 1971-08-26 | 1975-12-06 | ||
| JPS5028081B2 (enrdf_load_stackoverflow) * | 1971-09-01 | 1975-09-12 | ||
| DE2426116B2 (de) * | 1973-06-01 | 1978-05-11 | Efim Freiburg Biller (Schweiz) | Verfahren zur Herstellung von Methylenbrücken aufweisenden PoIyarylaminen |
| JPS5141633A (ja) * | 1974-10-07 | 1976-04-08 | Fuji Industries Co Ltd | Kinzokusoseikakokiniokeru rikeizaitofusochi |
-
1979
- 1979-01-08 CA CA000319238A patent/CA1137514A/en not_active Expired
- 1979-01-15 EP EP79100104A patent/EP0003303B1/de not_active Expired
- 1979-01-15 DE DE7979100104T patent/DE2960014D1/de not_active Expired
- 1979-01-23 JP JP564379A patent/JPS54117429A/ja active Granted
- 1979-01-24 BR BR7900430A patent/BR7900430A/pt unknown
- 1979-01-24 ES ES477114A patent/ES477114A1/es not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7038002B2 (en) | 2003-07-25 | 2006-05-02 | Bayer Materialscience Ag | Production of mixtures of diisocyanates and polyisocyanates from the diphenylmethane series with high contents of 4,4′-methylenediphenyl diisocyanate and 2,4′-methylenediphenyl diisocyanate |
| US7495124B2 (en) | 2004-02-04 | 2009-02-24 | Bayer Materialscience Ag | Process for the production of very pure 2,4′-methylenediphenyl diisocyanate |
| US8557949B2 (en) | 2007-09-19 | 2013-10-15 | Huntsman International Llc | Process for production of di- and polyamines of the diphenylmethane series |
| US9217054B2 (en) | 2007-09-19 | 2015-12-22 | Huntsman International Llc | Process for production of di- and polyamines of the diphenylmethane series |
| CN115745809A (zh) * | 2022-11-17 | 2023-03-07 | 万华化学集团股份有限公司 | 一种低杂质含量低副产品量的二苯基甲烷系列的二胺和多胺的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0003303A1 (de) | 1979-08-08 |
| JPS6331454B2 (enrdf_load_stackoverflow) | 1988-06-23 |
| JPS54117429A (en) | 1979-09-12 |
| BR7900430A (pt) | 1979-08-21 |
| DE2960014D1 (en) | 1980-12-18 |
| ES477114A1 (es) | 1979-07-01 |
| EP0003303B1 (de) | 1980-09-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |