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Figure 13. Examples of commercial fatty acid derived monomers. TOFA = tall oil fatty acids. Fatty Acid derivatives Oils and fats and their derivatives are already being used for a long time in the chemical industry. Compared to other major plant constituents such as carbohydrates, proteins and lignin, fatty acid derivatives are the easiest to handle in the current hydrocarbon-based chemical infrastructure, due to their often liquid nature and their low oxygen content. About 10% of the 170 million tonnes of oils and fats produced in 2009/2010 (128) are used as feedstock for the oleochemical industry. Palm, palm kernel and coconut oil, being rich in C12-C18 saturated and monounsaturated fatty acids, are important sources for a broad range of surfactants in soaps, detergents and personal care products. ‘Drying oils’ such as soybean, sunflower and linseed oil contain high levels of polyunsaturated fatty acids and are major raw materials for thermosetting systems such as coatings and ink resins, lacquers, and linoleum. Epoxidised soybean and linseed oils are used as (secondary) plasticisers and stabilisers in PVC. Rapeseed oil has a high level of oleic acid, and is therefore a favoured source for biolubricants, for which low viscosity combined with high oxidative and thermal stability are important properties. Although their number is currently relatively small, a few bifunctional building blocks derived from fatty acids are commercially applied. Ricinoleic acid (12-hydroxy-9- octadecenoic acid) from castor oil can be fragmented in two different ways, to obtain either a C10 dicarboxylic acid called sebacic acid, or 10-undecanoic acid. Sebacic acid is used for the preparation of polyamides such as nylon-4,10 (EcoPaXX® by DSM), nylon-10,10 (VESTAMID® Terra DS by Evonik; Zytel RS 6/10 by DuPont) and nylon-6,10 (VESTAMID® Terra HS by Evonik; Ultramid® BALANCE by BASF and Technyl eXten by Rhodia). 10-Undecenoic acid is converted by Arkema to 11- aminoundecanoic acid, the monomer for nylon-11 (Rilsan®). Arkema also produces sebaic acid based nylons-10.10 and 10.12 under the name hiprolon. DSM also produces a thermoplastic copolyester (Arnitel Eco) based on rapeseed oil, while BASF/Elastogran produces castor oil based polyols (Lupranol® BALANCE 50). Cognis produces azelaic acid, a C9 dicarboxylic acid, by ozonolysis of oleic acid. Azelaic acid is used as a monomer in nylon-6,9. A well-known class of branched difunctional oleochemical are the dimerised fatty acids or dimer acids. These are C36 dicarboxylic acids obtained by treating unsaturated fatty acids at high temperature with clay catalysts. Trimers are also formed. Dimer acids are used in polyamide resins for hot melt adhesives, but also as a modifier of polyesters, and in polyester polyols for e.g. polyurethanes. Dimer diols are obtained by reduction of dimer acids (or their dimethyl esters). A recent addition to the fatty dimer family is a C36 diamine (PriamineTM by Croda). Other oleochemical monomers for bioplastics described in recent scientific literature include 1,18-octadec-9-enedioic acid, a C18 dicarboxylic acid obtained by self-metathesis of oleic acid (129), dimethyl 1,19-nonadecanedioate, a C19 dicarboxylic acid ester produced by methoxycarbonylation of unsaturated C18 acids (130), and mid- to long-chain dicarboxylic acids obtained by microbial ω-oxidation of fatty acids (131). Croda Pripol for water resistance – C36 dimer fatty acid or dimer diol Pripol dimer acid and dimer diol are made from natural fatty acids, resulting in a 100% renewable carbon content. The products bring the following benefits, e.g. enhanced hydrophobicity, (low temperature) flexibility and improved melt flow properties and substrate wetting to PET modification. The Dimer diol is a bi-functional, low viscosity building block, especially suitable for high-end Polyurethane applications. PripolTM polymerised fatty acids are also used in a variety of industrial and consumer care applications, the highly lipophilic (oil-loving) structure providing unique performance benefits in lubricants, metal-working fluids, fuel additives, personal care products, corrosion inhibitors and rheology modifiers. Priplast for maintaining hardness – dimer based polyesters Priplast polyester polyols are made from dimer fatty acids and are ideal as larger soft segments to modify PET. The low polarity Priplast can be built in as an elongated soft segment. This results in a two-phase structure with soft, rubbery Priplast segments distributed in the hard PET matrix. This phase separated structure brings special benefits for PET including no compromise in hardness, improved impact strength, also at low temperatures and resistance to heat, oxidation, UV, hydrolysis and chemicals/petrol. http://www.croda.com/ (86) 26PDF Image | Bio-based Chemicals Value Added Products from Biorefineries
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