3896-58-0

Usage

Uses

Used in the Plastics Industry:
Vinyl Oleate is used as a key component in the production of plasticizers, resins, and polymers for its flexible properties, low melting point, and high flexibility. These characteristics are crucial in creating materials with resilience and durability.
Used in Skin Care Products:
Vinyl Oleate is used as a skin conditioning agent in some skin care products, providing benefits such as improved texture and hydration.

InChI:InChI=1/C20H36O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22-4-2/h4,11-12H,2-3,5-10,13-19H2,1H3/b12-11-

Upstream product

• 108-05-4 vinyl acetate 
• 112-80-1 cis-Octadecenoic acid 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 75-07-0 acetaldehyde 
• 74-86-2 acetylene 
• 105-38-4 vinyl propionate 

Downstream Products

• 2146-74-9 (+/-)-8-(cis-3-octyl-oxiranyl)-octanoic acid vinyl ester 
• 145014-07-9 (Z)-Octadec-9-enoic acid (S)-2-hydroxy-3-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester 
• 111-03-5 1-monooleoyl glycerol 
• 2465-32-9 1,3-diolein 
• 2442-61-7 1,2-dioleoylglycerol 
• 51067-90-4 1,3-dilauroyl-2-oleyl-glycerol 
• 1320208-40-9 6-O-(13-methyltetradecanoyl)-6'-O-oleoyl-α,α-trehalose 
• 338733-40-7 6,6'-di-O-oleoyl-α,α-trehalose 
• 338733-38-3 6-O-oleoyl-α,α-trehalose 
• 143767-53-7 5'-O-oleoyl-FUdR 
• 7207-70-7 3',5'-dioleoyl floxuridine 

Relevant academic research and scientific papers

Biobased and Sustainable Alternative Route to Long-Chain Cellulose Esters

Fatty acid cellulose esters (FACEs), which have been identified recently as sustainable film materials, are conventionally synthesized by the use of the reaction with acyl chloride/anhydride pyridine in the presence of LiCl/N,N-dimethylacetamide. In this study, we have developed a new synthetic route to FACEs using a vinyl ester of long chain fatty acid, which is an excellent biobased and highly reactive reagent, for the functionalization of cellulose. The developed method involves the synthesis of the long aliphatic fatty acid vinyl ester via a transition-metal-catalyzed transvinylation reaction between vinyl acetate and the fatty acid, followed by its subsequent reaction with cellulose to yield FACEs. In this work, we have used vinyl oleate as a model precursor to introduce the fatty acid chain to cellulose. The covalent grafting of the fatty acid chain to the free hydroxyl groups of cellulose was achieved through potassium carbonate (K2CO3)-catalyzed transesterification of vinyl oleate in the presence of N-methyl pyrrolidone as solvent with low toxicity. Successful functionalization of cellulose was confirmed by FTIR, 13C CP-MAS NMR, X-ray diffraction, and the thermogravimetric analysis. The results obtained showed that the functionalization efficiency of the cellulose increased with higher temperature and prolonged reaction times. The strategy proposed in the present work is an important step onward in terms of sustainability because the long-chain vinyl ester can be synthesized from a renewable and biobased source, and the toxic and corrosive chemicals commonly employed for cellulose esterification are avoided.

Dual Activity of Grubbs-Type Catalyst in the Transvinylation of Carboxylic Acids and Ring-Closing Metathesis Reactions

The development of a multifunctional catalyst, which mimics the promiscuity of enzymes, that would catalyze more than one chemical transformation in a single reaction vessel is one of the key points of modern sustainable chemistry. The results of our experiments indicated that Grubbs-type catalysts possess such multitask activity, catalyzing the transvinylation reaction of carboxylic acids without losing their original metathetic activity. This new activity of Grubbs catalysts was evidenced on several examples. It allows us to design a transvinylation/ring-closing metathesis (RCM) cascade reaction leading to the formation of endocyclic enol lactones from unsaturated carboxylic acids in an one-pot procedure. This unique ability of Grubbs catalyst to catalyze multiple mechanically distinct cascade reactions in a chemoselective way offers the new possibility for the synthesis of complex compounds from simple, easily accessible substrates.

Enzymatic esterification of glycerol III. Lipase-catalyzed synthesis of regioisomerically pure 1,3-sn-diacylglycerols and 1(3)-rac-monoacylglycerols derived from unsaturated fatty acids

Lipases that display high regioselectivities and broad substrate tolerance were used as catalysts for the efficient esterification of glycerol under the conditions of irreversible acyl transfer. A variety of unsaturated fatty acids, such as oleic, linoleic, erucic, ricinolic, hydroxystearic and coriolic acid, were used for this purpose in the form of their vinyl esters. Suitable biocatalysts were chosen on the basis of systematic screening experiments regarding their regioselectivities (RE) and substrate tolerances. Distinct differences were found and expressed in numerical RE values as a measure for differences of these biocatalysts as being specific, selective, and nonspecific. Based on these experiments, a variety of molecules were synthesized on a preparative scale (>150 mmol) in good yield (ca. 85%) and with high regioisomerical purities (>95% RE).