JPS60202844A - ポリアミンの製造方法 - Google Patents
ポリアミンの製造方法Info
- Publication number
- JPS60202844A JPS60202844A JP60037748A JP3774885A JPS60202844A JP S60202844 A JPS60202844 A JP S60202844A JP 60037748 A JP60037748 A JP 60037748A JP 3774885 A JP3774885 A JP 3774885A JP S60202844 A JPS60202844 A JP S60202844A
- Authority
- JP
- Japan
- Prior art keywords
- aniline
- formaldehyde
- reaction
- mixture
- hydrochloric 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.)
- Granted
Links
- 229920000768 polyamine Polymers 0.000 title claims description 31
- 229920001228 polyisocyanate Polymers 0.000 title claims description 13
- 239000005056 polyisocyanate Substances 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 84
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 72
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 56
- 239000000203 mixture Substances 0.000 claims description 53
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 230000005588 protonation Effects 0.000 claims description 9
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000004985 diamines Chemical class 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000007859 condensation product Substances 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 238000006482 condensation reaction Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 230000007423 decrease Effects 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 230000008707 rearrangement Effects 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000005191 phase separation Methods 0.000 description 5
- 239000012266 salt solution Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- SQMOOVFBFVTTGF-UHFFFAOYSA-N 1-benzyl-1-phenylhydrazine Chemical compound C=1C=CC=CC=1N(N)CC1=CC=CC=C1 SQMOOVFBFVTTGF-UHFFFAOYSA-N 0.000 description 2
- OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 241000861914 Plecoglossus altivelis Species 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010961 commercial manufacture process Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012084 conversion product Substances 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
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/14—Derivatives of isocyanic acid containing at least two isocyanate groups bound to the same carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3407494.5 | 1984-03-01 | ||
| DE19843407494 DE3407494A1 (de) | 1984-03-01 | 1984-03-01 | Verfahren zur herstellung von polyaminen und ihre verwendung zur herstellung von polyisocyanaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60202844A true JPS60202844A (ja) | 1985-10-14 |
| JPH0417943B2 JPH0417943B2 (en, 2012) | 1992-03-26 |
Family
ID=6229250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60037748A Granted JPS60202844A (ja) | 1984-03-01 | 1985-02-28 | ポリアミンの製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4597909A (en, 2012) |
| EP (1) | EP0158059B1 (en, 2012) |
| JP (1) | JPS60202844A (en, 2012) |
| BR (1) | BR8500879A (en, 2012) |
| CA (1) | CA1239414A (en, 2012) |
| DE (2) | DE3407494A1 (en, 2012) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005521722A (ja) * | 2002-03-28 | 2005-07-21 | 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及びその高級同族体の製造方法 |
| JP2006022100A (ja) * | 2004-07-05 | 2006-01-26 | Bayer Materialscience Ag | プロトン化度が低いジフェニルメタン系列のポリアミンの製造方法 |
| JP2007197448A (ja) * | 2006-01-28 | 2007-08-09 | Bayer Materialscience Ag | ジフェニルメタン系のジアミン及びポリアミンの製造方法 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4792624A (en) * | 1987-02-26 | 1988-12-20 | The Dow Chemical Company | Process for polymeric MDA, recycle of finished polymeric MDA |
| DE4026474A1 (de) * | 1990-08-22 | 1992-02-27 | Bayer Ag | Neue isocyanuratgruppen aufweisende polyisocyanatmischungen, ein verfahren zu ihrer herstellung und ihre verwendung zur herstellung von polyurethanschaumstoffen |
| DE10245703A1 (de) * | 2002-09-30 | 2004-04-01 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten der Diphenylmethanreihe durch Phosgenierung von nichtneutralisiertem Polyamin der Diphenylmethanreihe |
| DE10333929A1 (de) * | 2003-07-25 | 2005-02-24 | Bayer Materialscience Ag | Herstellung von Mischungen von Di- und Polyisocyanaten der Diphenylmethanreihe mit hohen Gehalten an 4,4'-Methylendiphenyldiisocyanat und 2,4'-Methylendiphenyldiisocyanat |
| DE102004005319A1 (de) | 2004-02-04 | 2005-08-25 | Bayer Materialscience Ag | Verfahren zur Herstellung von hochreinem 2,4'-Methylendiphenyldiisocyanat |
| EP2184144A1 (en) * | 2008-11-06 | 2010-05-12 | Huntsman International Llc | Polyisocyanate composition used for binding lignocellulosic materials |
| CN114057583B (zh) * | 2021-10-26 | 2025-02-18 | 菏泽永辉复合材料有限公司 | 一种4,4’-二氨基二苯基甲烷的制备方法及4,4’-二氨基二苯基甲烷 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3367969A (en) * | 1965-03-08 | 1968-02-06 | Du Pont | Process for the preparation of 4, 4'-methylenedianiline |
| US3476806A (en) * | 1969-08-13 | 1969-11-04 | Du Pont | Continuous methylenedianiline process |
| CA1137514A (en) * | 1978-01-25 | 1982-12-14 | Willi Eifler | Process for the preparation of polyamines of the diphenyl methane series which are rich in ortho isomers |
| 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 |
-
1984
- 1984-03-01 DE DE19843407494 patent/DE3407494A1/de not_active Withdrawn
-
1985
- 1985-02-18 CA CA000474571A patent/CA1239414A/en not_active Expired
- 1985-02-19 EP EP85101791A patent/EP0158059B1/de not_active Expired
- 1985-02-19 DE DE8585101791T patent/DE3560036D1/de not_active Expired
- 1985-02-21 US US06/703,843 patent/US4597909A/en not_active Expired - Lifetime
- 1985-02-28 JP JP60037748A patent/JPS60202844A/ja active Granted
- 1985-02-28 BR BR8500879A patent/BR8500879A/pt not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005521722A (ja) * | 2002-03-28 | 2005-07-21 | 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及びその高級同族体の製造方法 |
| JP2006022100A (ja) * | 2004-07-05 | 2006-01-26 | Bayer Materialscience Ag | プロトン化度が低いジフェニルメタン系列のポリアミンの製造方法 |
| JP2007197448A (ja) * | 2006-01-28 | 2007-08-09 | Bayer Materialscience Ag | ジフェニルメタン系のジアミン及びポリアミンの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3407494A1 (de) | 1985-09-05 |
| EP0158059A1 (de) | 1985-10-16 |
| BR8500879A (pt) | 1985-10-15 |
| DE3560036D1 (en) | 1987-02-05 |
| EP0158059B1 (de) | 1986-12-30 |
| US4597909A (en) | 1986-07-01 |
| CA1239414A (en) | 1988-07-19 |
| JPH0417943B2 (en, 2012) | 1992-03-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |