The reaction of nonconjugated unsaturated fatty acid esters with maleic anhydride

Bickford, W. G.; Krauczunas, P.; Wheeler, D. H.

doi:10.1007/bf02547718

Cited by 29 publications

(13 citation statements)

References 8 publications

(2 reference statements)

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“…First, the reaction mechanism was studied during the 1940s and up to the early 1950s by using ASA from FA or FA esters. Demonstration of the -ene reaction mechanism was debated and finally established during this period (9)(10)(11). Second, the strong development of petrol resources in the early 1950s favored the production of ASA from straight or branched olefins or even from polyolefins (4,12).…”

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confidence: 99%

Synthesis and characterization of oleic succinic anhydrides: Structure‐property relations

Candy

Vaca‐Garcia

2005

J Americ Oil Chem Soc

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Alkenyl succinic anhydrides (ASA) were prepared by an -ene reaction of n-alkyl (C 1 to C 5 ) oleates with maleic anhydride. The purified compounds were characterized by FTIR, 1 H NMR, and MS analytical methods to elucidate their structures. Their physicochemical properties were systematically studied and found to depend on the length of the alkyl radical. Structure-property relations were established for viscosity, m.p., and density. The combination of a long hydrophobic chain and a highly polar group with density values close to that of water implied good emulsification properties for some of these molecules. Comparison of the thermal properties of alkyl oleates and their respective ASA demonstrated that the grafting of maleic anhydride allowed the synthesis of compounds with very low melting temperatures (less than -60°C) and good stability at high temperatures (greater than 350°C) under both air and helium atmospheres. All these properties suggest a strong potential for application in the biolubricant or surfactant fields. The combined influences of the succinic part and variable ester moieties imply that each ASA molecule has its own characteristics, based on which applications could be developed.Paper no. J10734 in JAOCS 82, 271-277 (April 2005). FIG. 2. FTIR spectrum of pentyl oleate succinic anhydride. Wavenumber (cm -1 ) STRUCTURE-PROPERTY RELATIONS OF OLEIC SUCCINIC ANHYDRIDES 275 JAOCS, Vol. 82, no. 4 (2005) FIG. 4. Specific gravities of ASA and alkyl oleates as a function of the length of their ester moiety. For abbreviation see Figure 1.

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confidence: 99%

Synthesis and characterization of oleic succinic anhydrides: Structure‐property relations

Candy

Vaca‐Garcia

2005

J Americ Oil Chem Soc

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“…intervals for determination of reflectance with a multipurpose reflectometer. 3 The relative compatibilities were judged by observing whether or not the molded slabs exuded or smeared a Amber 45 °, 0 ° direction reflectance. on contact during shelf-aging for 225 days at room temperature.…”

Section: Methodsmentioning

confidence: 99%

“…It has been established 1)reviously (3,4) that male,inization of monoethenoid conipoullds results in the formation of alkenyl sneeinic anhydrides in which the anhydride moiety is attached to a earl)on atom alpha 1o the double` bond. It was assumed therefore that; I)roduets of the same iialur(~ would result fronl the niale,inization of ;io.ioba oil or its eonlpononts.…”

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Derivatives of jojoba oil as plasticizers for vinyl polymers and Buna‐N rubber

Fore

Pastor

Hughes

et al. 1960

J Americ Oil Chem Soc

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Summary Ten maleinated jojoba oil derivatives were screened as plasticizers in a standard polyvinyl resin formulation and as softeners for Buna‐N rubber. Three of these, the methyl and butyl esters and hydrogenated methyl esters of maleinated jojoba acids, were comparable to the reference standard, DOP, as primary plasticizers for the vinyl resin. Three others were satisfactory only as secondary plasticizers. Six of the derivatives were comparable to the reference softener, dibutyl sebacate, as softeners in a Buna‐N formulation and yielded rubbers meeting the low temperature flexibility requirements (−40°C.) of the automotive industry. Two of the six, those made with the butyl and hydrogenated butyl esters of maleinated jojoba acids, met the still more stringent low‐temperature requirements of the aircraft industry (−55°C.). In general, hydrogenation of a derivative adversely affected its compatibility in either the vinyl copolymer or the Buna‐N formulations.

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“…First, during the forties and up to the early fifties, the studies of the reaction mechanism lead to ASA from fatty acids or fatty acid esters. The demonstration of the ene-reaction mechanism was debated and finally established during this period [12][13][14]. Second, the strong development of petrol resources in the early fifties favored the production of ASA from straight or branched olefins, or even from polyolefins [4,15].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of alkenyl succinic anhydrides from methyl esters of high oleic sunflower oil

Candy

Vaca‐Garcia

2005

Eur. J. Lipid Sci. Technol.

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Synthesis of alkenyl succinic anhydrides from methyl esters of high oleic sunflower oilAlkenyl succinic anhydrides (ASA) have been prepared by ene-reaction of high-oleic sunflower oil methyl esters with maleic anhydride in a 50% xylene medium. Response surface methodology (RSM) was used to investigate the influence of two factors: reaction temperature and molar ratio between maleic anhydride (MA) and methyl esters (SME). The studied parameters in 8-h reactions were the methyl oleate conversion, the distillation yield in ASA, and responses allowing the indirect estimation of side reaction products: clarity index and dynamic viscosity. The highest yield in ASA (.70%; clarity index <10) was reached for a temperature of 240-250 7C with a molar ratio of 1.5-1.7. But for an industrial application requiring minimized side products (clarity index .40), the optimal synthesis conditions were: temperature between 220 and 235 7C and molar ratio of 1.2-1.35 (yield <55%). Such conditions did not provide a medium free of side products, even if xylene decreased their formation. Compared to solvent-free synthesis, conversion was lower with xylene. With solvent, higher temperatures were needed to reach the same yields. Supplementary heating compensated the reagent dissolution effect that slows down the kinetics of the ene-reaction. The influence of reaction time at 220 7C with a MA/SME ratio of 1.2 in a 50% xylene medium was studied. A reaction time of 8-10 h provided a good compromise between ASA yield and side products.

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The reaction of nonconjugated unsaturated fatty acid esters with maleic anhydride

Cited by 29 publications

References 8 publications

Synthesis and characterization of oleic succinic anhydrides: Structure‐property relations

Synthesis and characterization of oleic succinic anhydrides: Structure‐property relations

Derivatives of jojoba oil as plasticizers for vinyl polymers and Buna‐N rubber

Synthesis of alkenyl succinic anhydrides from methyl esters of high oleic sunflower oil

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