Fatty acid esters, epoxidized

Many PVC stabilizer formulations also contain one or more organic costabilizers that can also absorb hydrogen chloride. Typical of these additives are epoxidized fatty acid esters and organophosphites ... 

Epoxide/fatty acid esters Air drying and/or stoving Oxidative polymerisation Aliphatic and/or aromatic hydrocarbons Fair Fair Fairly good Poor Poor/fairly good ... 

Following the successful development of epoxidized soybean oil( 5), mainly as a stabilizer adjuvant with high permanence but poor low temperature plasticizing properties, the epoxidized fatty acid esters were introduced. These included the C8 mono-hydric alcohol esters — octyl epoxystearate and octyl epoxy-tallate. They also acted as stabilizer adjuvants but with outstanding low temperature plasticizing properties. The epoxy stabilizer/plasticizers have grown to over 50,000 tons/year in the U.S. in 1978, with the epoxidized soybean oil type predominating. 

When used in PVC organophosphites act as secondary heat stabilizers. In other resins such as PP, PS, HOPE and ABS plastics they function as antioxidants. p-Diketones are well-known co-stabilizers more particularly for zinc carboxylates. The synergistic action of epoxidized fatty acid esters like ESO or butylepoxy stearate as plasticizer, HCl scavenger and stabilizer for labile chlorine atoms in the catalytic presence of Zn and Cd salts is shown in Fig. 7 (see also 5.2.3)... 

Since the epoxide group reacts with acids, epoxidized fatty acid esters have become popular as plasticizer for PVC with a good stabilizing effect. Such compounds are not only able to bind hydrogen... 

Fatty acid methyl esters are now the main intermediates in oleochemistry. Epox-idation can be considered as a transformation currently applied to triglycerides that is easy to perform on an industrial scale, compared with the production process for fatty alcohol. Therefore, why should epoxidized fatty acid methyl esters not become one of the commodities of the future The commercial development of these compounds requires easy, environmentally friendly (e.g., avoiding catalyst use) routes of low production cost as well as identified industrial outputs. Such considerations were taken into account in this study both rapeseed methyl esters (RME) and high-oleic sunflower methyl esters (HOSME) were used as starting materials. 

Characteristics of Methyl Esters Used for Epoxidation Fatty Acid Composition by CC ... 

As mentioned, epoxidized fatty acids, esters, and alcohols are used for polyurethanepolyols after ring opening with water or alcohols (4) (Fig. 11). However, the ring opening of internal epoxides, in contrast to those of ethylene or propylene oxide, is not trivial, and quite harsh reaction conditions (160-200°C, sulfuric acid) have to be used (39). Therefore, the direct synthesis of these epoxide derivatives is a worthy target. 

A copol5m er that contains epoxy groups can be added to form biodegradable blends (51). It is preferable to use such copolymers based on styrene, acrylate, or methacrylate. In general, the compounds have two or more epoxy groups in the molecule. Further, glycidyl acrylate and glycidyl methacrylate or epoxidized fatty acid esters are suitable. 

PBT (50)/PPE-g-MA (50)/ diglycidyl ester of fatty acid dimer (2) Injection molded/mechanical properties/HDT/melt viscosity vs. blends with less epoxide Nakamura et al. 1988... 

Fast-fusing plasticizers enable the PVC material to be processed faster or at lower temperatures. Generally it is in the area of plasfisol applications where the uses of faster fusing plasticizers are preferred. Examples of fast-fiising plasticizers include butyl benzyl phthalate (BBP), citrates, the epoxidized fatty acid plasticizer methyl epoxy stearate, alkyl sulfonic acid esters of phenol, dibutyl phthalates and tere-phthalates, and dibenzoate esters and benzoate ester blends. It should be noted that the use of BBP in PVC has rapidly declined because of product restrictions, while the use of dibutyl phthalate (DBP) declined in North America and in Europe years ago because of its high volatility. 

Likewise, monocaroboxylic acid esters of poly(ol)s show good plasticizing properties. Further, epoxidized fatty acid esters are suitable as plasticizers and as stabilizers for PVC. 

Methylene glycol. See Formaldehyde Methyl epoxy soyate. See Epoxidized soybean oil, methyl ester Methyl ester of coconut oil fatty acids. See Methyl cocoate Methyl esters of fatty acids INS911... 

Epo>y Compounds. Epoxidized soya oil (ESO) is the most widely used epoxy-type additive and is found ia most mixed metal stabilized PVC formulations at 1.0—3.0 phr due to its versatiHty and cost effectiveness. Other usefiil epoxy compounds are epoxidized glycerol monooleate, epoxidized linseed oil, and alkyl esters of epoxidized tall oil fatty acid. 

Epoxide resins can be esterified with fatty acids to give media ranging from air-drying to stoving types. The presence of fatty acid reduces the chemical resistance to the same order as that of the alkyds. It is nevertheless sometimes found advantageous to use an epoxy ester for certain specialised purposes. 

Lubricants Fatty acid esters could be suitable lubricants, but their resistance to oxidation and tribological properties need to be improved. This can be achieved by epoxidation of the fatty acids followed by alcoholysis of the epoxide (Scheme... 

The epoxidation of fatty acid methyl esters (FAME) is traditionally conducted in strong acidic media, e.g., with peracetic acid in sulfuric acid solutions. These reactions can be conducted by an environmentally benign route, however, in the... 

In polymer applications derivatives of oils and fats, such as epoxides, polyols and dimerizations products based on unsaturated fatty acids, are used as plastic additives or components for composites or polymers like polyamides and polyurethanes. In the lubricant sector oleochemically-based fatty acid esters have proved to be powerful alternatives to conventional mineral oil products. For home and personal care applications a wide range of products, such as surfactants, emulsifiers, emollients and waxes, based on vegetable oil derivatives has provided extraordinary performance benefits to the end-customer. Selected products, such as the anionic surfactant fatty alcohol sulfate have been investigated thoroughly with regard to their environmental impact compared with petrochemical based products by life-cycle analysis. Other product examples include carbohydrate-based surfactants as well as oleochemical based emulsifiers, waxes and emollients. 

The desire to minimize this competitive oligomerization has motivated research into alternative means to decrease the polydispersity and simultaneously increase the molecular weight of the seed-oil derived polyols. Recent patents [128, 129] investigate an approach previously demonstrated for the hydroformylated polyols [130-132], i.e., hydroxylation of the fatty acid alkyl ester followed by polymerization from a petrochemically derived initiator molecule. Inventors state that this approach provides an improvement over previous epoxidized/hydroxylated polyols by allowing better control of the molecular weight and the functionality of the polyol products. 

Olefin epoxidation by hydrogen peroxide catalysed by MTO on niobia in the presence of urea was successfully applied with better results than under homogeneous conditions, thereby transforming simple olefin substrates to unsaturated fatty acids and esters [56,57]. 

A number of glycidates are important intermediates in the synthesis of fragrance materials. A few glycidates are fragrance materials in themselves. They are prepared either by epoxidation of the corresponding acrylates or by condensation of aldehydes or ketones with a-chloro substituted fatty acid esters (Darzens reaction). 

Essential oils may comprise volatile compounds of terpenoid or non-terpe-noid origin. All of them are hydrocarbons and their oxygenated derivatives. Some may also contain nitrogen or sulphur derivatives. They may exist in the form of alcohols, acids, esters, epoxides, aldehydes, ketones, amines, sulphides, etc. Monoterpenes, sesquiterpenes and even diterpenes constitute the composition of many essential oils. In addition, phenylpropanoids, fatty acids and their esters, or their decomposition products are also encountered as volatiles [1-16, 21-33, 36-38]. 

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