CA1055048A - Process for the cyanoethylation of aromatic amines - Google Patents
Process for the cyanoethylation of aromatic aminesInfo
- Publication number
- CA1055048A CA1055048A CA250,183A CA250183A CA1055048A CA 1055048 A CA1055048 A CA 1055048A CA 250183 A CA250183 A CA 250183A CA 1055048 A CA1055048 A CA 1055048A
- Authority
- CA
- Canada
- Prior art keywords
- aromatic
- process according
- amine
- silica
- acrylonitrile
- 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
- 150000004982 aromatic amines Chemical class 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 36
- 238000007278 cyanoethylation reaction Methods 0.000 title claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 35
- 125000003118 aryl group Chemical group 0.000 claims abstract description 24
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229920000768 polyamine Polymers 0.000 claims abstract description 20
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000007791 liquid phase Substances 0.000 claims abstract description 3
- -1 polymethylene Polymers 0.000 claims description 17
- 239000000376 reactant Substances 0.000 claims description 11
- 150000004984 aromatic diamines Chemical class 0.000 claims description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 229920000265 Polyparaphenylene Polymers 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000004992 toluidines Chemical class 0.000 claims description 4
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical group C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 3
- OHQOKJPHNPUMLN-UHFFFAOYSA-N n,n'-diphenylmethanediamine Chemical class C=1C=CC=CC=1NCNC1=CC=CC=C1 OHQOKJPHNPUMLN-UHFFFAOYSA-N 0.000 claims description 3
- 150000004986 phenylenediamines Chemical class 0.000 claims description 3
- 229920006389 polyphenyl polymer Polymers 0.000 claims 1
- 150000004998 toluenediamines Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 20
- 239000007795 chemical reaction product Substances 0.000 abstract description 8
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004970 Chain extender Substances 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 241001112258 Moca Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical class NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000063 preceeding effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000003039 volatile agent Substances 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
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/568,794 US3943162A (en) | 1975-04-16 | 1975-04-16 | Cyanoethylation of aromatic amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1055048A true CA1055048A (en) | 1979-05-22 |
Family
ID=24272771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA250,183A Expired CA1055048A (en) | 1975-04-16 | 1976-04-13 | Process for the cyanoethylation of aromatic amines |
Country Status (6)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4171322A (en) * | 1978-06-16 | 1979-10-16 | Suntech, Inc. | High selectivity cyanoethylation process |
| JPS57201778U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1981-06-17 | 1982-12-22 | ||
| JPH0650268U (ja) * | 1992-12-07 | 1994-07-08 | 住友電装株式会社 | コネクタ |
| DE4303131A1 (de) * | 1993-02-04 | 1994-08-11 | Bayer Ag | Verfahren zur Herstellung von Mono-N-beta-cyanoethylanilinen |
| EP1314716A1 (en) * | 2001-11-23 | 2003-05-28 | Sigma Coatings B.V. | Amine phenolic compounds and their use as hardener and/or accelerators in epoxy coatings |
| CN113956178B (zh) * | 2021-09-23 | 2023-08-11 | 万华化学集团股份有限公司 | 一种n,n’-二氰乙基-二氨基二苯基甲烷及其制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1992615A (en) * | 1931-09-10 | 1935-02-26 | Ig Farbenindustrie Ag | Amino nitrile and process of producing same |
| CH397712A (de) * | 1961-08-04 | 1965-08-31 | Geigy Ag J R | Verfahren zur Cyanäthylierung primärer und sekundärer aromatischer Amine |
| US3496213A (en) * | 1967-07-11 | 1970-02-17 | Du Pont | Mono-cyanoethylation of aromatic amines with an aqueous zinc chloride catalyst |
| US3766240A (en) * | 1971-02-24 | 1973-10-16 | Upjohn Co | N-(cyanoethyl)polyols of methylene-dianilines |
| US3876570A (en) * | 1971-02-24 | 1975-04-08 | Upjohn Co | Polyurethane foams based on certain alkoxylated cyanoethylated aryl amines |
-
1975
- 1975-04-16 US US05/568,794 patent/US3943162A/en not_active Expired - Lifetime
-
1976
- 1976-02-13 DE DE19762605675 patent/DE2605675A1/de not_active Ceased
- 1976-03-15 GB GB10233/76A patent/GB1492728A/en not_active Expired
- 1976-04-13 CA CA250,183A patent/CA1055048A/en not_active Expired
- 1976-04-15 FR FR7611124A patent/FR2307799A1/fr active Granted
- 1976-04-16 JP JP51042640A patent/JPS51128923A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51128923A (en) | 1976-11-10 |
| FR2307799A1 (fr) | 1976-11-12 |
| US3943162A (en) | 1976-03-09 |
| FR2307799B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-03-20 |
| GB1492728A (en) | 1977-11-23 |
| JPS565385B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-02-04 |
| DE2605675A1 (de) | 1976-10-28 |
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