GB1567638A - Process the production of polyaryl amines containing methylene bridges - Google Patents
Process the production of polyaryl amines containing methylene bridges Download PDFInfo
- Publication number
- GB1567638A GB1567638A GB46742/76A GB4674276A GB1567638A GB 1567638 A GB1567638 A GB 1567638A GB 46742/76 A GB46742/76 A GB 46742/76A GB 4674276 A GB4674276 A GB 4674276A GB 1567638 A GB1567638 A GB 1567638A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aryl amine
- salt
- aniline
- exchange
- 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 83
- 150000001412 amines Chemical class 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 150000004982 aromatic amines Chemical class 0.000 claims description 85
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 82
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 229920000768 polyamine Polymers 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 21
- 239000012266 salt solution Substances 0.000 claims description 21
- 239000008346 aqueous phase Substances 0.000 claims description 17
- 238000009833 condensation Methods 0.000 claims description 16
- 230000005494 condensation Effects 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 16
- 239000012071 phase Substances 0.000 claims description 15
- 239000012074 organic phase Substances 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000003377 acid catalyst Substances 0.000 claims description 11
- 230000002209 hydrophobic effect Effects 0.000 claims description 11
- 150000007513 acids Chemical class 0.000 claims description 10
- 238000009434 installation Methods 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 9
- -1 arylamine salt Chemical class 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims description 5
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical group CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 claims description 4
- 238000010790 dilution Methods 0.000 claims description 4
- 239000012895 dilution Substances 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 description 11
- 238000011282 treatment Methods 0.000 description 9
- 238000007792 addition Methods 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 238000000605 extraction Methods 0.000 description 8
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- GGFOZRQCNXQCLO-UHFFFAOYSA-N aniline;methanesulfonic acid Chemical class CS(O)(=O)=O.NC1=CC=CC=C1 GGFOZRQCNXQCLO-UHFFFAOYSA-N 0.000 description 3
- 230000008707 rearrangement Effects 0.000 description 3
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- 239000002585 base Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- WKBALTUBRZPIPZ-UHFFFAOYSA-N 2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N WKBALTUBRZPIPZ-UHFFFAOYSA-N 0.000 description 1
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-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
- 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007423 decrease Effects 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
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 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
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
-
- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/06—Amines
- C08G12/08—Amines aromatic
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1461875 | 1975-11-11 | ||
| CH585476 | 1976-05-05 | ||
| CH1004976 | 1976-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1567638A true GB1567638A (en) | 1980-05-21 |
Family
ID=27175350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB46742/76A Expired GB1567638A (en) | 1975-11-11 | 1976-11-10 | Process the production of polyaryl amines containing methylene bridges |
Country Status (22)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE848T1 (de) * | 1978-09-12 | 1982-04-15 | Gebrueder Sulzer Aktiengesellschaft | Verfahren zur herstellung von methylenbruecken aufweisenden polyarylaminen. |
Family Cites Families (8)
| 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 |
| GB1287141A (en) * | 1969-01-01 | 1972-08-31 | Ici Ltd | Manufacture of methylene-bridged polyarylamines |
| DE2227110C3 (de) * | 1972-06-03 | 1984-08-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyaminen |
| DE2238378C3 (de) * | 1972-08-04 | 1975-01-09 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Perlnonfarbstoffe und Verfahren zu Ihrer Herstellung |
| DE2238920C3 (de) * | 1972-08-08 | 1984-09-27 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyaminen |
| DE2343658C2 (de) * | 1973-08-30 | 1982-06-03 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyaminen |
| DE2356828C2 (de) * | 1973-11-14 | 1982-10-21 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyaminen und ihre Verwendung als Ausgangsmaterial zur Herstellung von Polyisocyanaten |
| DE2500573A1 (de) * | 1975-01-09 | 1976-07-15 | Bayer Ag | Verfahren zur herstellung von polyaminen |
-
1976
- 1976-10-28 DE DE2648982A patent/DE2648982C2/de not_active Expired
- 1976-10-29 IE IE2421/76A patent/IE44544B1/en unknown
- 1976-11-05 CA CA264,973A patent/CA1087633A/en not_active Expired
- 1976-11-05 YU YU02717/76A patent/YU271776A/xx unknown
- 1976-11-05 PT PT65803A patent/PT65803B/pt unknown
- 1976-11-05 IL IL50857A patent/IL50857A/xx unknown
- 1976-11-06 RO RO7688358A patent/RO79103A/ro unknown
- 1976-11-06 GR GR52122A patent/GR60355B/el unknown
- 1976-11-09 SE SE7612478A patent/SE421533B/xx unknown
- 1976-11-09 LU LU76153A patent/LU76153A1/xx unknown
- 1976-11-09 DD DD7600195684A patent/DD128184A5/xx unknown
- 1976-11-09 PL PL1976193576A patent/PL104368B1/pl unknown
- 1976-11-10 TR TR19975A patent/TR19975A/xx unknown
- 1976-11-10 MX MX166949A patent/MX148753A/es unknown
- 1976-11-10 FR FR7634029A patent/FR2331575A1/fr active Granted
- 1976-11-10 BR BR7607527A patent/BR7607527A/pt unknown
- 1976-11-10 GB GB46742/76A patent/GB1567638A/en not_active Expired
- 1976-11-10 ES ES453159A patent/ES453159A1/es not_active Expired
- 1976-11-11 NL NL7612539A patent/NL7612539A/xx not_active Application Discontinuation
- 1976-11-11 JP JP51136170A patent/JPS5260895A/ja active Pending
- 1976-11-11 AT AT0836676A patent/ATA836676A/de not_active Application Discontinuation
- 1976-11-11 DK DK508476A patent/DK508476A/da not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| YU271776A (en) | 1982-05-31 |
| SE7612478L (sv) | 1977-05-12 |
| SE421533B (sv) | 1982-01-04 |
| PL104368B1 (pl) | 1979-08-31 |
| IL50857A (en) | 1981-05-20 |
| PT65803A (en) | 1976-12-01 |
| IE44544B1 (en) | 1981-12-30 |
| LU76153A1 (enrdf_load_stackoverflow) | 1977-05-18 |
| FR2331575B1 (enrdf_load_stackoverflow) | 1980-05-09 |
| DK508476A (da) | 1977-05-12 |
| DE2648982A1 (de) | 1977-05-26 |
| JPS5260895A (en) | 1977-05-19 |
| ATA836676A (de) | 1982-08-15 |
| NL7612539A (nl) | 1977-05-13 |
| BR7607527A (pt) | 1977-09-20 |
| IL50857A0 (en) | 1977-01-31 |
| IE44544L (en) | 1977-05-11 |
| DD128184A5 (de) | 1977-11-02 |
| DE2648982C2 (de) | 1985-07-11 |
| PT65803B (en) | 1978-05-12 |
| TR19975A (tr) | 1980-06-02 |
| GR60355B (en) | 1978-05-18 |
| ES453159A1 (es) | 1978-03-01 |
| RO79103A (ro) | 1982-06-25 |
| FR2331575A1 (fr) | 1977-06-10 |
| CA1087633A (en) | 1980-10-14 |
| MX148753A (es) | 1983-06-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |