Osage Orange (<i>Maclura pomifera</i> L.) Seed Oil Poly(α-hydroxydibutylamine) Triglycerides: Synthesis and Characterization

Harry-O’kuru, Rogers E.; Tisserat, Brent; Gordon, Sherald H.; Gravett, Alan

doi:10.1021/acs.jafc.5b01625

Cited by 11 publications

(14 citation statements)

References 12 publications

(30 reference statements)

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“…This 847 cm −1 band of the diepoxy jojoba oil is in contrast to epoxy triglycerides which consistently give an asymmetric doublet at 825–845 cm −1 . Also, in contradistinction to triglycerides, jojoba oxirane showed a rather broad 1 H singlet at 2.87 ppm for protons in the three-membered rings and a strong single line for the corresponding ring 13 C spectrum at 57.12 ppm in contrast to the multiple lines in the 57 to 53 ppm spectral region in triglycerides [ 26 , 27 ]. At room temperature, both the oxirane and tetrahydroxylated jojoba intermediates are colorless low-melting solids.…”

Section: Resultsmentioning

confidence: 99%

Physical Characteristics of Tetrahydroxy and Acylated Derivatives of Jojoba Liquid Wax in Lubricant Applications

Harry-O’kuru

Biresaw

Gordon

et al. 2018

Journal of Analytical Methods in Chemistry

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Jojoba liquid wax is a mixture of esters of long-chain fatty acids and fatty alcohols mainly C38:2–C46:2. The oil exhibits excellent emolliency on the skin and, therefore, is a component in many personal care cosmetic formulations. The virgin oil is a component of the seed of the jojoba (Simmondsia chinensis) plant which occurs naturally in the Sonora Desert in the United States and northwestern Mexico as well as in the northeastern Sahara desert. The seed contains 50–60% oil by dry weight. The plant has been introduced into Australia, Argentina, and Israel for commercial production of the jojoba oil. As a natural lubricant, we are seeking to explore its potential as a renewable industrial lubricant additive. Thus, we have chemically modified the carbon-carbon double bonds in the oil structure in order to improve its already good resistance to air oxidation so as to enhance its utility as well as its shelf life in nonpersonal care applications. To achieve this goal, we have hydroxylated its –C=C– bonds. Acylation of the resulting hydroxyl moieties has generated short-chain vicinal acyl substituents on the oil which keep the wax liquid, improving its cold flow properties and also protecting it from auto-oxidation and rancidity.

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Section: Resultsmentioning

confidence: 99%

Physical Characteristics of Tetrahydroxy and Acylated Derivatives of Jojoba Liquid Wax in Lubricant Applications

Harry-O’kuru

Biresaw

Gordon

et al. 2018

Journal of Analytical Methods in Chemistry

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“…The protocol was adapted from a previously published work [24]. The reaction was carried out in a round bottom flask that was equipped with a reflux condenser and a magnetic stirrer.…”

Section: Methodsmentioning

confidence: 99%

New Insight on the Study of the Kinetic of Biobased Polyurethanes Synthesis Based on Oleo-Chemistry

Peyrton

Chambaretaud

2019

Molecules

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Nowadays, polyols are basic chemicals for the synthesis of a large range of polymers, such as polyurethane foams (PUF), which are produced with several other compounds, such as polyisocyanates. During the last decades, the oleo-chemistry has developed several routes from glycerides to polyols for the polyurethanes (PU) industry to replace mainly conventional fossil-based polyols. A large range of biobased polyols can be now obtained by epoxidation of the double bonds and ring-opening (RO) of the subsequent epoxides with different chemical moieties. In preliminary studies, the RO kinetics of an epoxidized model molecule (methyl oleate) with ethanol and acetic acid were investigated. Subsequently, polyols that were derived from unsaturated triglycerides were explored in the frame of e.g., PUF formulations. Different associations were studied with different mono-alcohols derived from epoxidized and ring-opened methyl oleate while using several ring-openers to model such systems and for comparison purposes. Kinetic studies were realized with the pseudo-first-order principle, meaning that hydroxyls are in large excess when compared to the isocyanate groups. The rate of isocyanate consumption was found to be dependent on the moiety located in β-position of the reactive hydroxyl, following this specific order: tertiary amine >> ether > ester. The tertiary amine in β-position of the hydroxyl tremendously increases the reactivity toward isocyanate. Consequently, a biobased reactive polyurethane catalyst was synthesized from unsaturated glycerides. These approaches offer new insights regarding the replacement of current catalysts often harmful, pungent, and volatile used in PU and PUF industry, in order to revisit this chemistry.

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“…A similar strategy has been described for Osage orange seed oil whose composition is rich in unsaturated fatty acids (about 12% oleic acid and 76% linoleic acid). 111 Quantitative amounts of the epoxidized triglycerides are obtained using peroxyformic acid generated in situ. The same procedure has been successfully applied to soybean, 112 linseed, 113 and cottonseed oils.…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Synthetic Transformations for the Valorization of Fatty Acid Derivatives

et al. 2017

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Oleochemistry is a growing field from the industrial point of view, and one of the basis for a more sustainable chemical production, less dependent of fossil sources. From this point of view, the development of selective and efficient synthetic transformations of triglycerides and fatty acids and esters is an active research field. This short review describes an overview of the most recent advances in the synthetic transformations of fatty acid derivatives into valuable chemicals. 1 Introduction 2 Triglycerides 2.1 Reactions on the ester group and multistep processes 2.2 Epoxidation 2.3 Ozonolysis 2.4 Cross metathesis 3 Reactions on the ester group of fatty acids and esters 3.1 Synthesis of free carboxylic acids 3.2 Synthesis of carboxylic esters 3.3 Reduction to alcohols and aldehydes 3.4 Synthesis of nitrogenated derivatives 4 Oxidation of Unsaturated Fatty acids and esters 4.1 Epoxidation and reactions of epoxides 4.2 Allylic oxidation 4.3 Synthesis of ketoderivatives 4.4 Oxidative cleavage 5 Addition reactions of unsaturated fatty acids and esters 5.1 Hydrogenation and hydroformilation 5.2 Cycloadditions and related reactions 5.3 Addition of carboxylic acids 5.4 Hydroalkylation 5.5 Radical additions 6 Other reactions of unsaturated fatty acids and esters 6.1 Cross metathesis 6.2 Isomerization 7 Conclusion and outlook

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Osage Orange (Maclura pomifera L.) Seed Oil Poly(α-hydroxydibutylamine) Triglycerides: Synthesis and Characterization

Cited by 11 publications

References 12 publications

Physical Characteristics of Tetrahydroxy and Acylated Derivatives of Jojoba Liquid Wax in Lubricant Applications

Physical Characteristics of Tetrahydroxy and Acylated Derivatives of Jojoba Liquid Wax in Lubricant Applications

New Insight on the Study of the Kinetic of Biobased Polyurethanes Synthesis Based on Oleo-Chemistry

Synthetic Transformations for the Valorization of Fatty Acid Derivatives

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