GB781549A - Process for preparing fatty acid di-hydroxyalkyl amides, and products of such process - Google Patents
Process for preparing fatty acid di-hydroxyalkyl amides, and products of such processInfo
- Publication number
- GB781549A GB781549A GB36589/55A GB3658955A GB781549A GB 781549 A GB781549 A GB 781549A GB 36589/55 A GB36589/55 A GB 36589/55A GB 3658955 A GB3658955 A GB 3658955A GB 781549 A GB781549 A GB 781549A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxyalkyl
- oil
- amide
- acids
- ester
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
N : N-Di-(hydroxyalkyl)-amides of fatty acids are prepared by adding to a preformed quantity of such amide in the liquid state a fatty acid ester, di(hydroxyalkyl) amine and an amidation catalyst, reacting the ester and amine to form the amide and recovering the latter. The reaction may be carried out in two stages by removing some of the liquid and completing the reaction separately, e.g. at a higher temperature. When this is done continuously sufficient amide must be left behind to maintain the reactants in a homogeneous liquid phase. The fatty acid ester used may be that of a mono-, dior polyhydric alcohol but it is preferred to use an ester of a monohydric alcohol of 1-5 carbon atoms such as methanol or ethanol, as these alcohols can easily be removed from the product by distillation. Glyceride esters may, however, be used. The fatty acids may be saturated or unsaturated acids of 10-22 carbon atoms whose esters are normally not miscible with di-(hydroxyalkyl) amines. The catalyst may be an alkali metal or amide or alkoxide thereof, particularly suitable being the alkoxide obtained by reacting the di-(hydroxyalkyl) amine reactant with concentrated aqueous alkali hydroxide and distilling off the water; such catalyst may be formed in situ. In the examples diethanolamine is reacted with methyl laurate, the methyl ester of coconut acids, and palm oil to give the corresponding amides. Other specified reactants are the esters of palmitic, stearic, myristic, oleic, ricinoleic, linoleic and linolenic acids, including lard, coconut oil, corn oil, cottonseed oil, soy bean oil and hydrogenated fish oil, also fatty acids of beeswax and carnauba wax. Besides glycerol and methanol the esterifying alcohol may be another alkanol, glycol, sorbitol, mannitol, inositol or pentaerythritol; the latter may be partly or wholly esterified. Other amines that may be used are dipropanolamine, dibutanolamine, dipentanolamine, dihexanolamine, dioctanolamine and di-glycerol-mono- and diamines.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US781549XA | 1954-12-29 | 1954-12-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB781549A true GB781549A (en) | 1957-08-21 |
Family
ID=22142269
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB36589/55A Expired GB781549A (en) | 1954-12-29 | 1955-12-21 | Process for preparing fatty acid di-hydroxyalkyl amides, and products of such process |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB781549A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3395162A (en) * | 1963-08-26 | 1968-07-30 | Lever Brothers Ltd | Process for the preparation of amides |
EP1903092A3 (en) * | 2006-09-21 | 2010-10-06 | Afton Chemical Corporation | Alkanolamides and their use as fuel additives |
-
1955
- 1955-12-21 GB GB36589/55A patent/GB781549A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3395162A (en) * | 1963-08-26 | 1968-07-30 | Lever Brothers Ltd | Process for the preparation of amides |
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 |
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