DE2202500A1 - Herstellung des 4,4'-Isomeren von Diaminodiphenylmethan - Google Patents
Herstellung des 4,4'-Isomeren von DiaminodiphenylmethanInfo
- Publication number
- DE2202500A1 DE2202500A1 DE19722202500 DE2202500A DE2202500A1 DE 2202500 A1 DE2202500 A1 DE 2202500A1 DE 19722202500 DE19722202500 DE 19722202500 DE 2202500 A DE2202500 A DE 2202500A DE 2202500 A1 DE2202500 A1 DE 2202500A1
- Authority
- DE
- Germany
- Prior art keywords
- diaminodiphenylmethane
- isomers
- aniline
- formaldehyde
- product
- 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- Withdrawn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
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 36
- 229920000768 polyamine Polymers 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 16
- UTNMPUFESIRPQP-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]aniline Chemical class C1=CC(N)=CC=C1CC1=CC=CC=C1N UTNMPUFESIRPQP-UHFFFAOYSA-N 0.000 claims description 9
- 150000004985 diamines Chemical class 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 claims description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229920001228 polyisocyanate Polymers 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000008098 formaldehyde solution Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000011496 polyurethane foam Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000007787 solid Substances 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 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
- LNWBFIVSTXCJJG-UHFFFAOYSA-N [diisocyanato(phenyl)methyl]benzene Chemical class C=1C=CC=CC=1C(N=C=O)(N=C=O)C1=CC=CC=C1 LNWBFIVSTXCJJG-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- VULHYRAYXYTONQ-UHFFFAOYSA-N n-phenylmethanimine Chemical class C=NC1=CC=CC=C1 VULHYRAYXYTONQ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US109979A US3860637A (en) | 1971-01-26 | 1971-01-26 | Selective manufacture of 4,4{40 -isomer of diaminodiphenyl-methane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2202500A1 true DE2202500A1 (de) | 1972-08-10 |
Family
ID=22330618
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722202500 Withdrawn DE2202500A1 (de) | 1971-01-26 | 1972-01-19 | Herstellung des 4,4'-Isomeren von Diaminodiphenylmethan |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3860637A (2) |
| JP (1) | JPS5623979B1 (2) |
| CA (1) | CA993893A (2) |
| DE (1) | DE2202500A1 (2) |
| FR (1) | FR2124752A5 (2) |
| GB (1) | GB1334618A (2) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2528694A1 (de) * | 1975-06-27 | 1976-12-30 | Bayer Ag | Verfahren zur herstellung von polyaminen |
| DE2557501A1 (de) * | 1975-12-19 | 1977-06-30 | Bayer Ag | Verfahren zur herstellung von polyaminen |
| DE2557500A1 (de) * | 1975-12-19 | 1977-06-30 | Bayer Ag | Verfahren zur herstellung von polyaminen |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3971829A (en) * | 1974-11-18 | 1976-07-27 | Jefferson Chemical Company, Inc. | Preparation of methylene-bridged polyphenylpolyamine mixtures |
| US4039580A (en) * | 1975-07-24 | 1977-08-02 | The Upjohn Company | Process for preparing di(aminophenyl)methanes |
| US4029705A (en) * | 1975-08-18 | 1977-06-14 | The Upjohn Company | Purification process for MDA |
| US4028361A (en) * | 1975-08-18 | 1977-06-07 | The Upjohn Company | Process for the purification of MDA |
| DE10006452A1 (de) | 2000-02-14 | 2001-08-16 | Bayer Ag | Verfahren zur Herstellung von Diaminodiphenylmethanen |
| DE10031540A1 (de) * | 2000-06-28 | 2002-01-10 | Basf Ag | Verfahren zur Herstellung eines aromatischen Polyamingemisches |
| US20110021741A1 (en) * | 2008-04-16 | 2011-01-27 | Dow Global Technologies Inc. | Process for making polyaminopolyphenyl methanes using a mixed solid acid catalyst system |
| CN102399155B (zh) * | 2011-12-29 | 2014-03-26 | 河南省华鼎高分子合成树脂有限公司 | 4,4'-二氨基二苯基甲烷的制备方法 |
| HUE037918T2 (hu) | 2014-07-07 | 2018-09-28 | Covestro Deutschland Ag | Eljárás a difenilmetán sorozat di- és poliaminjainak elõállítására |
| KR102735962B1 (ko) | 2016-01-20 | 2024-11-29 | 바스프 에스이 | 방향족 폴리아민 혼합물의 제조 방법 |
| US10538480B2 (en) | 2016-06-30 | 2020-01-21 | Covestro Deutschland Ag | Process for the production of di- and polyamines of the diphenylmethane series |
| WO2025128774A1 (en) * | 2023-12-13 | 2025-06-19 | Dow Global Technologies Llc | Method for making methylene dianiline and polymethylene polyanilines |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2974168A (en) * | 1955-09-19 | 1961-03-07 | Monsanto Chemicals | Process for making methylenedianiline |
| US3297759A (en) * | 1964-01-13 | 1967-01-10 | Upjohn Co | Continuous process for producing mixtures of methylene-bridged polyphenyl polyamines |
| US3517062A (en) * | 1966-08-05 | 1970-06-23 | Mobay Chemical Corp | Process for the preparation of substantially pure 4,4'-diaminodiphenylmethane |
| US3476806A (en) * | 1969-08-13 | 1969-11-04 | Du Pont | Continuous methylenedianiline process |
-
1971
- 1971-01-26 US US109979A patent/US3860637A/en not_active Expired - Lifetime
- 1971-11-15 CA CA127,689A patent/CA993893A/en not_active Expired
- 1971-12-21 GB GB5924171A patent/GB1334618A/en not_active Expired
-
1972
- 1972-01-14 FR FR7201300A patent/FR2124752A5/fr not_active Expired
- 1972-01-19 DE DE19722202500 patent/DE2202500A1/de not_active Withdrawn
- 1972-01-19 JP JP755772A patent/JPS5623979B1/ja active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2528694A1 (de) * | 1975-06-27 | 1976-12-30 | Bayer Ag | Verfahren zur herstellung von polyaminen |
| DE2557501A1 (de) * | 1975-12-19 | 1977-06-30 | Bayer Ag | Verfahren zur herstellung von polyaminen |
| DE2557500A1 (de) * | 1975-12-19 | 1977-06-30 | Bayer Ag | Verfahren zur herstellung von polyaminen |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5623979B1 (2) | 1981-06-03 |
| US3860637A (en) | 1975-01-14 |
| FR2124752A5 (2) | 1972-09-22 |
| CA993893A (en) | 1976-07-27 |
| GB1334618A (en) | 1973-10-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |