American Oil Chemist's Society

45th

FALL MEETING

P R O G R A M

OCTOBER 3-6, 1971

Chalfonte-Haddon Hall Hotel

Atlantic City, New Jersey

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308 JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY

TABLE II

Solubility of Polyol Esters

VOL. 48

Polyol ester, % added

Glycerol Triglycerol Hexaglycerol Decaglycerol

1% 10% 100% 1% 10% 100% 1% 10% 100% 1% 10% 100%

Water Acetate S a S Butyrate S S Caproate D D Benzoate D I Calrylate S I Pelargonate D I Caprate D D Laurate D I Ethanol

Isopropanol Acetate S S Butyrate S S Caproate S S Benzoate S S Caprylate S S Pelargonate S S Caprate S S Laurate S S

Cot tonseed oil Acetate D D Butyrate D D Caproate S D Benzoate S D Caprylate S S Pelargonate S S Caprate S S Laurate S S

S S S S S S D D D S S S D D D S D D I D D I D S I D D S D S I D D D S S D D D D S D I D D D D D

All esters were miscible with 95% ethanol.

S S S S S D S S S S S D S S S S S S S S S S S S S S S S S D S S S S S D S S S S S S S S S S S D

I I I I I I I I I I D D D D D D D D D D S D D D S D D D S D D I

S S S S S S S S S S S S I D S S S S S S S S S S D S S S D S D D

D D S S D D S S

D D S S D D D D

I I I I I I I I I I I I I I I I

aAbbreviat ion: S, soluble; D, dispersible; I, insoluble.

laboratory supply houses. The gas chromatographic analysis of the acids fractionated in our laboratories indicated a purity of better than 93%. Each ester was formed by heating the free acid with the molar equivalent of the polyol at a temperature where water formation was rapid and steady. Esterification temperatures ranged from 300 F at the start to 400 F towards the end of the reaction. When volatile acids were used in the reaction, it was necessary to add slightly more than the equivalent weight to replace that lost by volatilization. The reaction, carried out under a carbon dioxide atmosphere, was considered complete when the acid value was less than two. The product was deodorized under vacuum of less than 5 mm Hg for 1-2 hrs at temperatures from 230 to 300 F depending upon the ester. The deodorization removed low molecular weight odoriferous by-products, unreacted polyol and the free acids to lower the acid value to less than 0.5.

RESULTS AND DISCUSSION

It would be impossible to synthesize and characterize all of the short and medium chain esters of all possible polyglycerols. Triglycerol, hexaglycerol and decaglycerol were selected as being representative of this class of compounds; glycerol was also chosen because of its

TABLE III

Absorption of Water by Monoesters, %

Compound Glycerol Triglycerol Hexaglycerol Decaglycerol

Acetate inf inf inf inf Butyrate 42 inf inf inf Caproate 9 230 620 900 Benzoate 10 85 290 320 Caprylate 4 1800 850 inf Pelargonate 16 500 inf inf Caprate 14 250 800 inf Laurate -- 30 70 1 O0

similarity to these compounds and it is more familiar and therefore useful for comparative purposes. Even carbon aliphatic carboxylic acids from acetic to lauric, the nine carbon containing pelargonic acid, and benzoic acid, an aromatic ring containing carboxylic acid, were each reacted with the homologous series of polyglycerols.

All of the partial esters of the polyglycerols were liquids at room temperature; the glycerol mono-, diesters of capric, pelargonic and lauric acids were crystalline whereas the lower esters were liquid. They varied in color from about Gardner 1 to 8. The decaglycerol esters were heavy and so thick that they were barely pourable at room temperature. The viscosity of the triglycerol esters was the least of the polyglycerols but still greater than that of the glycerol mono-, diesters.

Some of the properties of the esters are shown in Table I. The hydroxyl values found for the glycerol series were, as a whole, low as compared to the calculated. The calculated values represent 100% monoglyceride whereas the reaction of equimolar mixtures of glycerine and acid does not produce such an ideal product. If the laws of random distribution are applied to this reaction we would expect about 45 mole per cent monoglyceride and 30 mole per cent free glycerol at completion. This would correspond to a free glycerol content from 10-20% by weight for the laurate and acetate esters respectively. Removal of free glycerol lowers the hydroxyl value dramatically, since the theoretical hydroxyl value of glycerol is 1800.

The triglycerol esters were stripped less rigorously than the glycerol esters as evidenced by higher acid values. The observed hydroxyl values are, however, reasonably close to the values calculated from the monoesters. The hexagly- cerol esters likewise had hydroxyl values which were in line with the theoretical values for the monoester.

In all cases the observed values for the decaglycerol monoesters was considerably below that of the calculated value. In this series the high viscosity of products necessitated the use of higher stripping temperatures to