GB1187131A - Method for producing Imidazolines and derivatives thereof - Google Patents
Method for producing Imidazolines and derivatives thereofInfo
- Publication number
- GB1187131A GB1187131A GB1859967A GB1859967A GB1187131A GB 1187131 A GB1187131 A GB 1187131A GB 1859967 A GB1859967 A GB 1859967A GB 1859967 A GB1859967 A GB 1859967A GB 1187131 A GB1187131 A GB 1187131A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reaction
- diamine
- water
- mols
- 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.)
- Expired
Links
- 150000002462 imidazolines Chemical class 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 abstract 6
- 150000004985 diamines Chemical class 0.000 abstract 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 5
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 4
- 239000000194 fatty acid Substances 0.000 abstract 4
- 229930195729 fatty acid Natural products 0.000 abstract 4
- 150000004665 fatty acids Chemical class 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 235000013162 Cocos nucifera Nutrition 0.000 abstract 1
- 244000060011 Cocos nucifera Species 0.000 abstract 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 1
- 229940106681 chloroacetic acid Drugs 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000006053 organic reaction Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 238000005956 quaternization reaction Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
- C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D233/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
- C07D233/10—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,187,131. Imidazolines. H. S. MANNHEIMER. 21 April, 1967 [22 April, 1966; 5 April, 1967], No. 18599/67. Heading C2C. An organic reaction product having a high content of an imidazoline of the formula wherein R 1 represents a C 2-4 alkyl or C 2-4 alkylol radical and R represents an alkyl, alkenyl or cycloalkyl radical containing at least 5 carbon atoms, a hydrocarbon radical of a resinic acid, or an alkaryl or alkenylaryl radical, the alkyl or alkenyl moiety containing at least 6 carbon atoms, is prepared by heating a diamine NH 2 -(CH 2 ) 2 -NHR 1 with a fatty acid R-COOH and continuously removing water of reaction and some of said diamine as a distillate, heating being continued until at least 1À75 mols water per mol fatty acid have been removed as distillate and, while said water of reaction is being produced, continuously maintaining in the reaction mixture at least 1À08 mols diamine per mol fatty acid originally in said mixture, the amount of diamine being calculated on the basis that none of the unremoved amine has reacted. It is preferred to use 1À1 1 mols diamine per mol acid, to continue the reaction until about 2 mols water have been removed and subsequently to strip the excess amine from the reaction mass. The reaction is generally effected by heating the reactants to an initial temperature of about 140‹ C. under reduced pressure and thereafter increasing the temperature to about 200‹ C. while further reducing the pressure and adding sufficient diamine below the surface of the reaction mass to maintain the required excess. The resultant produce has a particularly low diamide content and forms acid addition or quaternary salts which provide clear solutions in water. Examples describe the preparation of imidazolines from aminoethylethanolamine and lauric or coconut fatty acid and quaternization of the products with chloroacetic acid and NaOH.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54437366A | 1966-04-22 | 1966-04-22 | |
| US628519A US3408361A (en) | 1967-04-05 | 1967-04-05 | Methods for producing imidazolines and derivatives thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1187131A true GB1187131A (en) | 1970-04-08 |
Family
ID=27067599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1859967A Expired GB1187131A (en) | 1966-04-22 | 1967-04-21 | Method for producing Imidazolines and derivatives thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1187131A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001005A1 (en) * | 1977-08-18 | 1979-03-07 | Albright & Wilson Limited | Manufacture of imidazolines |
| EP0002943A1 (en) * | 1977-12-22 | 1979-07-11 | Albright & Wilson Limited | Process for the manufacture of imidazolines |
-
1967
- 1967-04-21 GB GB1859967A patent/GB1187131A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001005A1 (en) * | 1977-08-18 | 1979-03-07 | Albright & Wilson Limited | Manufacture of imidazolines |
| EP0002943A1 (en) * | 1977-12-22 | 1979-07-11 | Albright & Wilson Limited | Process for the manufacture of imidazolines |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |