Compositions – Electrolytes for electrical devices
Patent
1991-11-05
1993-08-10
Mc Avoy, Ellen
Compositions
Electrolytes for electrical devices
252 515A, 560155, 560169, 560171, 44391, 44399, 44400, C10M14912, C07C10102
Patent
active
052346129
DESCRIPTION:
BRIEF SUMMARY
The invention relates to a process for the production of ester derivatives useful as fuels and lubricating oil additives and to novel esters produced thereby.
Many ester derivatives useful in particular as fuels additives and processes for their preparation are known from, for example U.S. Pat. Nos. 4,198,306; 3,926,578; 4,210,425; 4,670,021 and 4,240,804.
U.S. Pat. No. 4,198,306 discloses poly(oxyalkylene)monoesters consisting of an amine moiety and a hydrocarbyl-poly(oxyalkylene) moiety bonded through an ester linkage, --O--C(O)--R.sup.1 --, where the oxygen atom is bonded to the poly(oxyalkylene) moiety, and wherein R.sup.1 is a C.sub.1 -C.sub.19 alkylene radical bonded to a nitrogen atom of said amine moiety. The amino esters are prepared by reacting a hydrocarbyl poly(oxyalkylene) alcohol with either a mono unsaturated monocarboxylic C.sub.2 -C.sub.20 acid, or an acid halide, anhydride or ester thereof containing an alpha, beta or gamma, halogen or hydrocarbylsulphonyl substituent, followed in a second step by reaction with an amine.
U.S. Pat. No. 3,926,578 discloses a hydrocarbylamine substituted ester of propionic acid represented by the formula: atoms, R.sup.1 is hydrogen or a lower alkyl radical having from 1 to 2 carbon atoms and R.sup.11 is a hydrocarbon radical having from about 8 to 22 carbon atoms. The ester is prepared by reacting approximately equal mole amounts of an aliphatic amine, acrylic acid and an alcohol or hydroxy compound. Generally the reaction is accomplished in two stages, in the first stage the alcohol and acrylic acid are reacted in the presence of an esterification catalyst to produce an unsaturated ester and in the second stage the unsaturated ester is reacted with a hydrocarbylamine.
U.S. Pat. No. 4,210,425 discloses the reaction product of a glycol polyether or polypropylene glycol represented by the formula: ##STR1## in which n represents a number from about 10 to 90 with an acrylic acid, represented by the formula: ##STR2## in which R is hydrogen or a methyl radical, and an amine represented by the formula: carbon atoms or a radical selected from the group represented by the formulas: monovalent hydrocarbon radical having from 1 to 8 carbon atoms. The reaction is accomplished in two steps, in the first step the glycol is reacted with an acrylic acid to form an intermediate unsaturated ester, which is reacted in a second step with the amine.
U.S. Pat. No. 4,670,021 discloses compounds of the formula: ##STR3## wherein R.sup.1, R.sup.2 =H, 8-20C hydrocarbyl or 8-20C alkoxy substituted hydrocarbon group; COR.sup.6, COOR.sup.7, phenyl or NO.sub.2 ; and ##STR4## involves a Knoevenagel reaction of dodecylaldehyde with malonic acid followed by Michael addition of tallow amine.
Finally, U.S. Pat. No. 4,240,804 discloses the reaction product of a polyamine (including diamine), or oxygen-containing polyamine, preferably an ether polyamine, and an alkyl ester of acrylic or alkyl acrylic acid.
The majority of the aforesaid processes for producing an ester derivative involve reacting an unsaturated monocarboxylic acid in the presence of an esterification catalyst and under esterification conditions with a hydroxylic compound to produce an ester in which the olefinic unsaturation is retained and thereafter reacting the ester with an amine. A problem with this approach to producing the ester derivatives is that conditions which favour esterification are conducive also to polymerisation of the olefinic double bond of the reactant acid or ester product. One solution to the problem of polymerisation is to add polymerisation inhibititors or suppressants, but these can contaminate the final product. We have found that the polymerisation problem can be avoided by removing the double bond in a facile first stage reaction, which does not require a catalyst or inhibitors, to form a stable intermediate, which can then be further reacted to produce the ester derivative.
Accordingly, the present invention provides a process for the production of an ester derivative, useful as a fuel or lubricating
REFERENCES:
patent: 3091521 (1963-05-01), Liao
patent: 3594171 (1971-07-01), Kimura et al.
patent: 3702339 (1972-11-01), Eck et al.
patent: 3926578 (1975-12-01), Cummings
patent: 4198306 (1980-04-01), Lewis
patent: 4210425 (1980-07-01), Cummings
patent: 4240804 (1980-12-01), Shields
patent: 5055588 (1991-10-01), Takase et al.
BP Chemicals (Additives) Limited
Mc Avoy Ellen
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