Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1990-11-20
1993-01-05
Dees, Jose G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560112, 560193, 560199, 560200, C07C 6710, C07C 6976, C07C 6934, C07C 6952
Patent
active
051772493
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to compounds comprising ester groups having at least three ester functions, to a process for the production thereof, and to the use of the products.
Monoesters of dicarboxylic acids are known. If these compounds are tried to be condensed with diols or polyols, polycondensates are formed and it is impossible to obtain low-molecular compounds by a reaction which may technically be utilized.
British Patent No. 1,379,335 describes the attempt to produce emulsion stabilizers by the reaction of unsaturated glycidyl esters with dicarboxylic acid monoesters. Owing to the tendency towards rearrangement and to the temperature sensitivity of the products obtained, the tedious reaction leads to polymer-containing and/or instable end products which do not permit technical utilization from the economic point of view.
The same applies to the alkoxylation of succinic acid with ethylene oxide where a bis-(hydroxy-ethyl)-succinate tending to rearrange is obtained (German Patent No. 544 288).
Proceeding from this state of the art, it is the object of the present invention to provide stable compounds comprising several ester functions starting from dicarboxylic acid monoesters, and it is a further object of the present invention to provide a process for the production of these compounds.
This object is achieved by the synthesis of ester-groups-containing-compounds having at least three functional ester groups of the following general formula; in the following these are called "triesters" according to the denotation m=1. ##STR2## The abbreviations have the following meaning: x=--CH.sub.2 --CH.sub.2 --or --CH.dbd.CH--, with one or more etherified or esterified hydroxy groups, aliphatic, cycloaliphatic or aromatic carboxylic acid with 2 to 22 carbon atoms, optionally with a saturated or unsaturated C.sub.4 -C.sub.16 -hydrocarbon residue as substituent, unsaturated aliphatic, cycloaliphatic or aromatic alcohol, or a group from an alkylene-oxide-adduct taking the alcohol function in the ester grouping,
Two synthesis methods were found.
The first one comprises the reaction of a dicarboxylic acid monoester with an epoxide, i.e., an alkoxylation of the carboxylic acid group whereby the dicarboxylic acid monoester-alkoxylate (dicarboxylic acid-hydroxyalkyl-alkyl-diester) resulting as intermediate product and being thermally instable is subsequently acylated and thus converted into the form of a stable triester.
The dicarboxylic acid monoester-alkoxylates resulting as intermediate product have the general formula: ##STR3## in which x, Y, R.sub.1, n, and m have the above mentioned meanings.
The acylation of the hydroxyalkyl group of the intermediate product, which hydroxyalkyl group tends to continue condensating, results in the formation of the temperature-resistant triesters. Acylation is carried out at temperatures ranging from 50.degree. to 120.degree. C., preferably 60.degree. to 90.degree. C., and can be applied to nearly all hydroxyalkyl-alkyl-dicarboxylic acid mixed esters.
In case of immediate conversion of the epoxide-addition-products into the thermally stable triesters by way of acylation, higher reaction temperatures and thus higher and more efficient reaction rates become possible.
The addition of the epoxide to the carboxyl function of the monoester is possible without catalyst, however, to increase the reaction velocity acidic or basic catalysts are generally used (Houben-Weyl, 4th edition, 6/3, page 447 ff.).
Longer residence of the formed intermediate product at elevated temperatures favors rearrangements. For this reason, addition of several moles alkylene oxide to the dicarboxylic acid monoester is limited due to the required longer reaction time. According to the present invention 1 to 3 moles are added.
A residual amount of unreacted dicarboxylic acid monoester in the reaction mixture after alkoxylation has a stabilizing influence on the formed hydroxyalkyl-alkyl-mixed ester. Preferably the acid value of the alkoxylation mixture is at least 5; in case of values below 5 considerable var
REFERENCES:
patent: 3960935 (1976-06-01), Samour
patent: 4316987 (1982-02-01), Ceprini et al.
Chemische Fabrik Stockhausen GmbH
Clarke Vera C.
Dees Jos,e G.
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