CA2126841C - A process for preparing methylene diphenylamines by partial neutralization of acidic methylene diphenylamines - Google Patents
A process for preparing methylene diphenylamines by partial neutralization of acidic methylene diphenylamines Download PDFInfo
- Publication number
- CA2126841C CA2126841C CA002126841A CA2126841A CA2126841C CA 2126841 C CA2126841 C CA 2126841C CA 002126841 A CA002126841 A CA 002126841A CA 2126841 A CA2126841 A CA 2126841A CA 2126841 C CA2126841 C CA 2126841C
- Authority
- CA
- Canada
- Prior art keywords
- acid
- reaction product
- reaction mixture
- reaction
- partial neutralization
- 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 - Fee Related
Links
- BTQLWKNIJDKIAB-UHFFFAOYSA-N 6-methylidene-n-phenylcyclohexa-2,4-dien-1-amine Chemical class C=C1C=CC=CC1NC1=CC=CC=C1 BTQLWKNIJDKIAB-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- 238000006386 neutralization reaction Methods 0.000 title claims description 9
- 230000002378 acidificating effect Effects 0.000 title description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 51
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 23
- 239000011541 reaction mixture Substances 0.000 claims abstract description 23
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 18
- 230000029087 digestion Effects 0.000 claims abstract description 17
- 239000003377 acid catalyst Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 230000003472 neutralizing effect Effects 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 description 15
- 229920000768 polyamine Polymers 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 229920001228 polyisocyanate Polymers 0.000 description 14
- 239000005056 polyisocyanate Substances 0.000 description 14
- 239000006260 foam Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- -1 polymethylene Polymers 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 229920006389 polyphenyl polymer Polymers 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 230000011514 reflex Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000011260 aqueous acid Substances 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical class NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000008707 rearrangement Effects 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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
- 239000012267 brine Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical class [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical class NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-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
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- NMFOOIYPNIYAID-UHFFFAOYSA-N 6-methylidene-1-phenylcyclohexa-1,3-diene Chemical group C=C1CC=CC=C1C1=CC=CC=C1 NMFOOIYPNIYAID-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical class NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920003226 polyurethane urea Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/094,933 | 1993-07-21 | ||
| US08/094,933 US6031136A (en) | 1993-07-21 | 1993-07-21 | Process for preparing methylene diphenylamines by partial neutralization of acidic methylene diphenylamines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2126841A1 CA2126841A1 (en) | 1995-01-22 |
| CA2126841C true CA2126841C (en) | 2005-12-13 |
Family
ID=22248008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002126841A Expired - Fee Related CA2126841C (en) | 1993-07-21 | 1994-06-27 | A process for preparing methylene diphenylamines by partial neutralization of acidic methylene diphenylamines |
Country Status (3)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7577598B2 (en) | 2001-05-01 | 2009-08-18 | United Parcel Service Of America, Inc. | Account opening facilitation system, method and computer program product |
| DE10141620A1 (de) * | 2001-08-24 | 2003-03-06 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten der Diphenylmethanreihe mit vermindertem Farbwert |
| DE10211021A1 (de) * | 2002-03-13 | 2003-09-25 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten der Diphenylmethanreihe mit vermindertem Farbwert |
| DE10228734A1 (de) * | 2002-06-27 | 2004-01-22 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten der Diphenylmethanreihe mit vermindertem Farbwert |
| DE10347438A1 (de) * | 2003-10-13 | 2005-05-04 | Bayer Materialscience Ag | Verfahren zur Herstellung von Di- und Polyaminen der Diphenylmethanreihe |
| DE102005006692A1 (de) * | 2005-02-15 | 2006-08-24 | Bayer Materialscience Ag | Verfahren zur Herstellung von Di-und Polyaminen der Diphenylmethanreihe |
| ES2364081T5 (es) * | 2005-12-08 | 2019-08-20 | Huntsman Int Llc | Procedimiento para preparar diaminodifenilmetanos |
| CN101279923B (zh) * | 2007-04-06 | 2010-08-25 | 宁波万华聚氨酯有限公司 | 一种制备多亚甲基多苯基多胺的方法 |
| ATE517860T1 (de) | 2007-04-06 | 2011-08-15 | Ningbo Wanhua Polyurethanes Co | Verfahren zur herstellung von polymethylenpolyphenylpolyamin |
| EP2039676A1 (en) * | 2007-09-19 | 2009-03-25 | Huntsman International Llc | Process for the production of di-and polyamines of the diphenylmethane series |
| EP2062869A1 (en) * | 2007-09-19 | 2009-05-27 | Huntsman International Llc | Process for the production of di-and polyamines of the diphenylmethane series |
| 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 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1288937A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1969-06-09 | 1972-09-13 | ||
| US4259526A (en) * | 1979-02-21 | 1981-03-31 | Bayer Aktiengesellschaft | Process for the preparation of mixtures of polyamines of the polyamino-polyaryl-polymethylene type |
| US4294987A (en) * | 1979-12-31 | 1981-10-13 | The Upjohn Company | Process for preparing methylene dianilines |
| US4465639A (en) * | 1983-01-26 | 1984-08-14 | The Upjohn Company | Process for polyisocyanates |
| US4792624A (en) * | 1987-02-26 | 1988-12-20 | The Dow Chemical Company | Process for polymeric MDA, recycle of finished polymeric MDA |
| US5286760A (en) * | 1992-10-09 | 1994-02-15 | Miles, Inc. | Process for reducing impurity levels in methylene diphenyamines |
-
1993
- 1993-07-21 US US08/094,933 patent/US6031136A/en not_active Expired - Fee Related
-
1994
- 1994-06-27 CA CA002126841A patent/CA2126841C/en not_active Expired - Fee Related
- 1994-07-19 MX MX9405490A patent/MX208237B/es unknown
-
1999
- 1999-12-29 US US09/474,628 patent/US6673970B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| MX208237B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2002-06-05 |
| CA2126841A1 (en) | 1995-01-22 |
| US6031136A (en) | 2000-02-29 |
| US6673970B1 (en) | 2004-01-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5286760A (en) | Process for reducing impurity levels in methylene diphenyamines | |
| KR100601243B1 (ko) | 감소된 양의 염소화 부산물을 포함하고 감소된 요오드 색지수를 갖는, 디페닐메탄 디이소시아네이트 및 폴리페닐렌-폴리메틸렌-폴리이소시아네이트로 구성된 혼합물의 제조 방법 | |
| JP5237564B2 (ja) | ジフェニルメタン系のジアミン及びポリアミンを製造する方法 | |
| CA2126841C (en) | A process for preparing methylene diphenylamines by partial neutralization of acidic methylene diphenylamines | |
| KR101183761B1 (ko) | 저양성자화도에서의 디페닐메탄계 폴리아민의 제조 방법 | |
| EP1890998B1 (en) | Process for the preparation of polyisocyanates of the diphenylmethane series | |
| US4465639A (en) | Process for polyisocyanates | |
| US5310769A (en) | Process for the production of polyamine mixtures of the polyamino-polyaryl-polymethylene series | |
| RU2398760C2 (ru) | Способ получения диаминодифенилметанов | |
| US4792624A (en) | Process for polymeric MDA, recycle of finished polymeric MDA | |
| US4259526A (en) | Process for the preparation of mixtures of polyamines of the polyamino-polyaryl-polymethylene type | |
| KR100860910B1 (ko) | 색도가 감소된 디페닐메탄계 폴리이소시아네이트의 제조방법 | |
| CA2421395A1 (en) | Process for producing polyisocyanates of the diphenyl methane series having a reduced color value | |
| KR100244696B1 (ko) | 밝은 색 폴리이소시아네이트 기재 발포체용 폴리아민의 제조 방법 | |
| US4597909A (en) | Process for the production of polyisocyanates | |
| RU2058303C1 (ru) | Способ получения смеси полифениленполиметиленполиизоцианатов | |
| US4657940A (en) | 4,4'-diisocyanto-phenylbenzylether, a process for the preparation thereof and use in the production of polyurethane plastics | |
| HK1062296A (en) | Process for the preparation of polyisocyanates of the diphenylmethane group having a reduced color value | |
| JP2004043743A (ja) | ポリメチレンポリフェニルポリイソシアネートの生産方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |