Isostearic Acid: A Unique Fatty Acid with Great Potential

Wiedemann, Sophie C.C.; Bruijnincx, Pieter C. A.; Weckhuysen, Bert M.

doi:10.1002/9783527698202.ch3

Cited by 5 publications

(13 citation statements)

References 83 publications

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“…Because iso-unsaturated fatty acids (IUFAs) can be easily obtained by zeolite catalyzed skeletal isomerization of unsaturated fatty acids (UFAs) and also as byproducts in clay catalyzed polymerization of (UFAs) at high temperatures in the oleochemical industry, − synthesis of polyol esters using these iso-unsaturated fatty acids has become the area of interest for researchers in recent past, e.g., Ngo et al, have used iso-oleic acid to synthesize iso-oleic acid esters as lubricant base stocks by the reaction of different fatty alcohols, and they observed that the synthesized iso-oleic acid esters showed a lower pour point and cold flow properties and high thermal and oxidative stabilities . Beimesch et al.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Iso-Undecenoic and Iso-Undecanoic Acids Based Polyol Esters

Yasa

Krishnasamy

Singh

et al. 2017

Ind. Eng. Chem. Res.

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The polymerization of 10-undecenoic acid (UDA) was carried out in the presence of montmorillonite K10 clay catalyst (5% of UDA) and deionized water (2.5% of UDA) at a temperature of 250 °C in an autoclave. The UDA polymerized product is a mixture of monomer acids (47−51%), dimer acids (30−32%), and higher polymeric acids (17−23%). The present study describes the isolation of less valuable monomer acids fraction (iso-undecenoic acid) through distillation from polymerization reaction product. This monomer acids fraction was found to be a mixture of iso-undecenoic acid (93−96%) and γ-undecalactone (4−7%) when analyzed by GC-MS. Monomer acids fraction was hydrogenated to also give hydrogenated monomer acids (iso undecanoic acids). Finally, the esterification of monomer and hydrogenated monomer acids fractions were done by the reaction with different polyols like neopentyl glycol (NPG), trimethylol propane (TMP), trimethylolhexane (TMH), and pentaerythritol (PE). Physicochemical and lubricant properties of all the synthesized polyol esters were evaluated including density, kinematic viscosity, pour point, flash point, thermal stability (TGA), oxidation stability (DSC), copper corrosion, weld load, and wear. All the synthesized polyol esters were found to be suitable as hydraulic fluids and automotive lubricants base stocks. Comparatively the iso-undecenoic acid based polyol esters were showed excellent pour point, viscosity-temperature properties, and good thermal stabilities, while the iso-undecanoic acid polyol esters showed good oxidation stability.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Iso-Undecenoic and Iso-Undecanoic Acids Based Polyol Esters

Yasa

Krishnasamy

Singh

et al. 2017

Ind. Eng. Chem. Res.

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“…Moreover, the position of the branch on the carbon chain has an influence on the physicochemical properties of future applications. 14,15 Hence, it epitomizes the importance of thoroughly understanding the reaction mechanism and accurately analyzing the product distribution.…”

Section: ■ Isomerization Mechanismmentioning

confidence: 99%

Branched Fatty Acids: The Potential of Zeolite Catalysis

Kerstens

Praet

Verhoeven³

et al. 2022

ACS Sustainable Chem. Eng.

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Isostearic acid, a C18 saturated branched chain fatty acid containing one or more methyl or ethyl groups on the carbon chain, is of great interest for the oleochemical industry due to its interesting physicochemical properties. Its current industrial production, as a side product of the acid clay catalyzed dimerization of unsaturated fatty acids, lacks efficiency. Therefore, research focuses strongly on new catalytic systems based on zeolites. Significantly higher yields of branched fatty acids can be obtained using zeolites, demonstrating their superiority compared to acid clay catalysts. Despite previous efforts, there is insufficient insight in the product itself and the catalytic system to use it optimally. With this knowledge, it would, however, be possible to tune zeolite catalysts to meet predetermined product compositions and thus application characteristics. This perspective aims to provide the knowledge required to get a profound insight in the current state-of-the-art while pointing at remaining questions and challenges. Focus is on the reaction mechanisms taking place during reaction, the analysis of the reaction product and the zeolite catalysts themselves.

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“…Linear saturated long-chain fatty acids with appropriate viscosities have high melting temperatures unsuitable for most lubricant applications. To date, the biobased fatty acid most closely matching the chemical properties of an ideal lubricant is a product termed “isostearic” acid, which is a mixture of branched fatty acids (BFAs) methylated at various positions on the stearate chain [ 3 , 4 ]. This non-specificity of branch point leads to mixed chemical properties.…”

Section: Introductionmentioning

confidence: 99%

“…This non-specificity of branch point leads to mixed chemical properties. Isostearic acid is produced by chemical transformation of unsaturated fatty acids, a process that also yields significant amounts of polymer byproducts [ 4 ], limiting the production volume and profitability of isostearic acid.…”

Section: Introductionmentioning

confidence: 99%

Production of 10-methyl branched fatty acids in yeast

Blitzblau

Consiglio

Teixeira

et al. 2021

Biotechnol Biofuels

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Background Despite the environmental value of biobased lubricants, they account for less than 2% of global lubricant use due to poor thermo-oxidative stability arising from the presence of unsaturated double bonds. Methyl branched fatty acids (BFAs), particularly those with branching near the acyl-chain mid-point, are a high-performance alternative to existing vegetable oils because of their low melting temperature and full saturation. Results We cloned and characterized two pathways to produce 10-methyl BFAs isolated from actinomycetes and γ-proteobacteria. In the two-step bfa pathway of actinomycetes, BfaB methylates Δ9 unsaturated fatty acids to form 10-methylene BFAs, and subsequently, BfaA reduces the double bond to produce a fully saturated 10-methyl branched fatty acid. A BfaA-B fusion enzyme increased the conversion efficiency of 10-methyl BFAs. The ten-methyl palmitate production (tmp) pathway of γ-proteobacteria produces a 10-methylene intermediate, but the TmpA putative reductase was not active in E. coli or yeast. Comparison of BfaB and TmpB activities revealed a range of substrate specificities from C14-C20 fatty acids unsaturated at the Δ9, Δ10 or Δ11 position. We demonstrated efficient production of 10-methylene and 10-methyl BFAs in S. cerevisiae by secretion of free fatty acids and in Y. lipolytica as triacylglycerides, which accumulated to levels more than 35% of total cellular fatty acids. Conclusions We report here the characterization of a set of enzymes that can produce position-specific methylene and methyl branched fatty acids. Yeast expression of bfa enzymes can provide a platform for the large-scale production of branched fatty acids suitable for industrial and consumer applications.

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Isostearic Acid: A Unique Fatty Acid with Great Potential

Cited by 5 publications

References 83 publications

Synthesis and Characterization of Iso-Undecenoic and Iso-Undecanoic Acids Based Polyol Esters

Synthesis and Characterization of Iso-Undecenoic and Iso-Undecanoic Acids Based Polyol Esters

Branched Fatty Acids: The Potential of Zeolite Catalysis

Production of 10-methyl branched fatty acids in yeast

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