Montmorency sour cherry (Prunus cerasus L.) pit oil (CPO) was extracted and characterized by various methods including: GC, LC–MS, NMR, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and X‐ray powder diffraction (XRD). The oil gave an acid value of 1.45 mg KOH/g, saponification value of 193 mg KOH/g and unsaponifiable matter content of 0.72 %. The oil contained oleic (O) and linoleic (l) acids as the major components with small concentrations of α‐eleostearic acid (El, 9Z,11E,13E‐octadecatrienoic acid) and saturated fatty acid palmitic (P) acid. The CPO contained six major triacyglycerols (TAG), OOO (16.83 %), OLO (16.64 %), LLO (13.20 %), OLP (7.25 %), OOP (6.49 %) and LElL (6.16 %) plus a number of other minor TAG. The TAG containing at least one saturated fatty acid constitute 33 % of the total. The polymorphic behavior of CPO as studied by DSC and XRD confirmed the presence of α, β′ and β crystal forms. The oxidative induction time of CPO was 30.3 min at 130 °C and the thermal decomposition temperature was 352 °C.

The combination of various functional groups, such as epoxy, acetoxy, methoxy, thiirane, and aziridine, on the fatty acyl chain of soy fatty acid alkyl esters have been synthesized and evaluated as plasticizers in poly(vinyl chloride) (PVC) applications. Numerous synthetic procedures, such as epoxidation, methoxylation, acetylation, thiiration, and aziridination, were used for synthesizing multifunctional soy fatty acid alkyl esters. Epoxidized soybean oil fatty acid alkyl ester served as the key intermediate for functionalization. Partial or complete ring opening of the epoxide by reacting with methanol and the subsequent etherification or acetylation of the hydroxyl function produced epoxy, alkoxy, and acetoxy derivatives. The nucleophilic substitution of epoxide with sulfur by reacting with ammonium thiocyanate produced thiirane and epoxy thiiranes. Although the aziridine derivatives were synthesized by reacting unsaturated fatty acid alkyl esters with chloramine-T, the compounds were fully characterized and their physical and analytical properties were determined. The high viscosity and darker color of aziridine and thiirane derivatives limit their usefulness, whereas the physical properties of the other derivatives were acceptable. The plasticizer evaluation of methoxy and acetoxy soy fatty acid esters (methyl and n-butyl) demonstrated good compatibility with PVC, high efficiency (Shore hardness), and gelling properties were comparable to commercial plasticizer, di-isoonyl phthalate. The abundant availability and cost-effectiveness of starting materials and the readily adoptable chemical processes make the fatty acid ester derivatives viable bioplasticizers to replace the fossil fuel-derived phthalates. J. VINYL ADDIT. TECH-

A facile synthesis of the soy fatty acid methyl ester ketal has been accomplished using acetone in the presence of catalytic anhydrous ferric chloride starting from commercially available soy biodiesel (soy fatty acid methyl ester) after evaluating various synthetic procedures. The soy ketal product was fully characterized by nuclear magnetic resonance, infra‐red and chromatography. The physical and analytical properties of soy ketal as determined by thermogravimetric analysis, viscosity acid and saponification values are acceptable for plasticizer applications. Soy ketal was compounded with polyvinyl chloride for evaluation of plasticizer properties such as efficiency, gelation, viscosity, volatility, thickening/aging behavior and stability. The thickening and aging behaviors of the soy ketal bioplasticizer are better than those of petroleum‐based plasticizers such as diisononyl phthalate and diisononyl‐cyclohexane dicarboxylate, but they need improvement in the areas of thermal stability and water extractability.

Fatty acid ester estolides were synthesized from soybean oil and evaluated for plasticizer functionality in poly(vinyl chloride) (PVC). The plasticization ability of the fatty acid ester estolides depends upon the molecular features such as polarity, molecular weight, and branching. The structure of the fatty acid derivatives was modified at the ester head group with various alcohols and the estolide branch was created at the site of unsaturation. Soy fatty acid esters of methanol, iso-butanol, 2-ethylhexanol, and glycerol were prepared to vary the size and polarity at the ester head group. Estolides of these fatty acid esters were prepared using two synthetic routes. In the first route, the fatty acid ester was condensed with an aliphatic acid at the site of unsaturation in the presence of a strong mineral acid. In the second route, the fatty acid ester double bonds were converted to epoxy groups, which were ring opened and acetylated to form acetate estolides. The first synthetic route resulted in low-average estolide content per fatty acid chain while the second route resulted in a higher estolide content per fatty acid chain. The fatty acid ester estolides compounded with PVC showed good plasticizer properties as evidenced by the rheological properties and reduction in glass transition temperature. The fatty acid ester estolides with a higher estolide content had better plasticizer functionality, comparable to commercial controls.

Plasticizers are nonvolatile organic liquids that impart flexibility to polymers. Due to environmental, health, and safety reasons, the industry is looking for bioplasticizers to replace petroleum‐derived phthalates. To fulfill this need, soy fatty acid ester estolides were synthesized, characterized, and evaluated as phthalate replacements. Soybean oil was transesterified with methanol or glycerol to form lower molecular weight fatty acid esters that were epoxidized and ring opened with acetic acid and acetylated to give the final products. Ring opening and acetylation of the epoxidized oleic acid esters gave acyclic acetate fatty acid ester estolides, whereas the polyunsaturated fatty acid esters, linoleate, and linolenate gave cyclic tetrahydrofuran derivatives and cross‐linked higher molecular weight materials. The cyclization mechanism to form the tetrahydrofuran derivatives was postulated. Soy fatty acid ester estolides were compounded with formulated poly(vinyl chloride), (PVC) and tested for their functional properties. The physical and functional properties of the new bioplasticizers were compared with commercial plasticizers. The elasticity of PVC compounded with experimental plasticizers and commercial phthalates was comparable. PVC compounded with fatty acid methyl ester estolide showed lower glass transition temperature and similar tensile properties compared to PVC compounded with the commercial phthalate. PVC compounded with the glyceryl fatty acid ester estolide showed a higher glass transition temperature, higher tensile properties compared to PVC compounded with the commercial phthalate.