GB693086A - Improvements relating to the preparation of alkylolamides - Google Patents
Improvements relating to the preparation of alkylolamidesInfo
- Publication number
- GB693086A GB693086A GB22156/51A GB2215651A GB693086A GB 693086 A GB693086 A GB 693086A GB 22156/51 A GB22156/51 A GB 22156/51A GB 2215651 A GB2215651 A GB 2215651A GB 693086 A GB693086 A GB 693086A
- Authority
- GB
- United Kingdom
- Prior art keywords
- mono
- diethanolamine
- coconut oil
- alkylolamine
- halide
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
Abstract
Alkylolamides are prepared by condensing a carboxylic halide with an alkylolamine in an aqueous solution containing a stable water-immiscible solvent for the alkylolamide to be produced and an acceptor for the liberated hydrogen halide and separating the alkylolamide from the aqueous mass and from the solvent. Suitable solvents are, for example, benzene, toluene, octane, iso-octane, heptane, carbon tetrachloride, chloroform, ethyl ether, isopropyl ether, n-butyl ether, amyl ether, dipropyl ketone, diisopropyl ketone, dibutyl ketone and diisobutyl ketone. Suitable acceptors for the hydrogen halide are potassium hydroxide, sodium hydroxide, lithium hydroxide, potassium carbonate, sodium carbonate, lithium carbonate, sodium bicarbonate, potassium bicarbonate, lithium bicarbonate, magnesium hydroxide and organic amines having a non-replaceable hydrogen atom, e.g. triethylamine and trimethylamine. Alkylolamine compounds suitable for amidation are, for example, monoethanolamine, diethanolamine, monopropanolamine, dipropanolamine, dibutanolamine, monobutanolamine, monoisobutanolamine, mono- and di-pentanolamine, mono- and di, hexanolamine, mono- and di-octanolaminemono - laurylolamine, mono - hexadecylolamine, mono - ethyl ethanolamine, monooctadecylolamine, mono - butyl ethanolamine, arylalkylolamines, cyclohexyl ethanolamine, ethanolaniline, 2 - methyl - amino - propanediol - 1,3, 1 - phenyl - amino - propanediol-2,3, 1 - hydroxy - ethyl - amino - 2 - methoxypropan-ol-3, diglycerol monoamine and diglyceroldiamine. The carboxylic acid halides may be derived from cyclic and acyclic, saturated and unsaturated acids. The condensation reaction between the alkylolamine and the carboxylic acid halide is preferably carried out at a pH of about 8.5 to 9, and at a temperature in the range 15-30 DEG C. In the examples (a) lauroyl chloride is prepared from lauric acid and phosphorus trichloride and added to a mixture of diethanolamine dissolved in water and ethylene dichloride; caustic potash is added and lauric diethanolamide with small amounts of lauric acid and diethanolamic ester are obtained; (b) phosphorus trichloride is reacted with coconut oil fatty acid to give the acid chloride which is condensed with diethanolamine in the presence of an aqueous p solution of potassium hydroxide and ethylene dichloride; coconut oil diethanolamide with small amounts of coconut oil fatty acid and diethanolamine ester are obtained.ALSO:Alkylolamides obtained by condensing a carboxylic acid halide with an alkylolamine may be used as wetting agents in the p laundering, textile, cosmetic, plastic and leather industries. The term "alkylolamines" covers simple alkylolamines, arylalkylolamines and cycloalkylolamines. The carboxylic acid halides may be the halides of cyclic, acyclic, saturated and unsaturated carboxylic acids or of a mixture of these or of a mixture with higher fatty acids derived from oils such as coconut, palm kernel, palm, olive, cottonseed, corn and peanut oils. In an example, coconut oil diethanolamide, containing a little coconut oil fatty acid and diethanolamine ester as byproducts, is stated to be suitable for incorporation into a detergent composition.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US693086XA | 1950-12-28 | 1950-12-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB693086A true GB693086A (en) | 1953-06-24 |
Family
ID=22088093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22156/51A Expired GB693086A (en) | 1950-12-28 | 1951-09-21 | Improvements relating to the preparation of alkylolamides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB693086A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1903092A3 (en) * | 2006-09-21 | 2010-10-06 | Afton Chemical Corporation | Alkanolamides and their use as fuel additives |
-
1951
- 1951-09-21 GB GB22156/51A patent/GB693086A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1903092A3 (en) * | 2006-09-21 | 2010-10-06 | Afton Chemical Corporation | Alkanolamides and their use as fuel additives |
| US8444720B2 (en) | 2006-09-21 | 2013-05-21 | Afton Chemical Corporation | Alkanolamides and their use as fuel additives |
| US9017430B2 (en) | 2006-09-21 | 2015-04-28 | Afton Chemical Corporation | Alkanolamides and their use as fuel additives |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2965576A (en) | Detergent compositions | |
| US2174507A (en) | Reaction of liquid n-alkanes with sulphur dioxide and chlorine and products thereof | |
| GB693086A (en) | Improvements relating to the preparation of alkylolamides | |
| US2806044A (en) | Esters of hydroxyalkanesulfonates with alpha-sulfonated long-chain fatty acids | |
| GB814858A (en) | Sequestering compositions | |
| US3499930A (en) | Tertiary amine oxides | |
| US2684969A (en) | Process for the preparation of hydroxy amides from hydroxy amines and carboxylic acid halides | |
| US3366632A (en) | N-oxides of 1-hydrocarbonoxy-2-hydroxy-3-morpholinopropanes | |
| US3763231A (en) | Detergent builder composition | |
| GB830054A (en) | Improvements in or relating to detergent preparations | |
| US2811549A (en) | Process of preparing high solids beta-alanine detergents | |
| US3660313A (en) | High foaming mixtures of fatty alcohol sulfates | |
| Wang et al. | Synthesis of new amino acid-type amphoteric surfactants from tall oil fatty acid | |
| US2938872A (en) | Sulfated chloroalkanol detergents | |
| GB751273A (en) | Improvements in soapless detergent compositions | |
| US2075013A (en) | Acylamino alkyl-aryl ethers and their sulphonation products | |
| US3522333A (en) | Phosphonamide sulfonates | |
| GB573662A (en) | Detergent composition | |
| US2849450A (en) | Manufacture of salts of alkyl acid sulfates in one step | |
| US2968664A (en) | Fatty acid esters of hydroxyalkanesulfonic acid amine salts | |
| US3250718A (en) | Process for preparing a liquid detergent composition | |
| US2427576A (en) | Ether sulphonates and their production | |
| GB800710A (en) | Improvements in or relating to detergent compositions | |
| GB758224A (en) | Process for the production of diethylaminoaceto-2:6-xylidide | |
| Hart | Determination of Active Ingredients and Fatty Matter in Surface-Active Agents |