Chemical composition

Abstract

Abstract 1,053,193. Alkanol amine salts of alkyl acid orthophosphate esters. E. I. DU PONT DE NEMOURS & CO. June 15, 1965 [June 15, 1964; Jan. 13, 1965], No. 25243/65. Heading C2C. [Also in Division C5] The invention comprises a salt of a primary mono- or di-alkyl orthophosphate ester in which each alkyl group contains from 8 to 16 carbon atoms and an alkanol amine having the formula wherein R and R<SP>1</SP> are hydrogen or alkyl, cycloalkyl, phenyl or alkyl phenyl groups, R and R<SP>1</SP> together containing a total of from 8 to 24 carbon atoms, R<SP>11</SP> is an alkyl, cycloalkyl, phenyl or aralkyl group containing 6 to 25 carbon atoms and R<SP>111</SP> is hydroxyethyl or a hydroxypropyl radical. The salt may be prepared by neutralizing the alkyl orthophosphate ester with the appropriate alkanol amine, the reactants normally being in equimolar proportions. The orphosphate esters may be obtained by reacting an alcohol (3 moles) with phosphorus pentoxide (1 mole) to give an approximately equimolar mixture of the corresponding mono- and di-alkyl esters of phosphoric acid. This mixture may be used as such to prepare a mixture of amine salts or the separate esters may be isolated from it and used to prepare individual amine salts. The alcohols used may be branched- or straight-chain primary alkanols having 8 to 16 carbon atoms or mixtures thereof. The branched-chain alkanols may be those prepared by the Oxo-process using a branchedchain olefin such as C 7 -C 15 mono-olefinic polymers and interpolymers of propylene and butylene, or they may be prepared by the aldolisation of appropriate aldehydes followed by hydrogenation or by the alkaline condensation of primary alcohols of the type RCH 2 CH 2 OH where R is an alkyl group of from 2 to 6 carbon atoms. The alkanol-amines of type A above may be obtained by the reaction of the appropriate amine RR<SP>1</SP>NH with 3-chloropropanediol-1,2 and those of type B may be prepared by reading the appropriate amine R<SP>11</SP>NH 2 with ethylene oxide or propylene oxide or, when R<SP>111</SP> is hydroxyethyl, by reacting the alkyl or aralkyl chloride R<SP>11</SP>Cl with diethanolamine. The amine phosphate salts are useful as anti-stalling additives for hydrocarbon distillate fuels (see Division C5).

Inventors

• 👤 Philip Lee Bartlett
• 👤 Charles Bedford Biswell

Bibliographic Details