141-38-8Relevant academic research and scientific papers
Homogeneous and heterogeneous catalytic (dehydrogenative) oxidation of oleochemical 1,2-diols to α-hydroxyketones
Vu, Nam Duc,Guicheret, Boris,Duguet, Nicolas,Métay, Estelle,Lemaire, Marc
supporting information, p. 3390 - 3399 (2017/07/28)
Herein, the preparation of methyl oleate α-hydroxyketone from the corresponding 1,2-diol was investigated using both homogeneous and heterogeneous systems. Homogeneous conditions using a Pd(OAc)2/neocuproine complex were first developed using oxygen as a sole oxidant under mild conditions (MeOH, 50 °C). Under these conditions, the conversion of diol reached 95%, and α-hydroxyketone was obtained with 97% selectivity. The access to α-hydroxyketone has also been studied by dehydrogenation using a range of heterogeneous catalysts under solvent-free conditions at high temperatures (160-180 °C). Dehydrogenation using activated Ru/C under vacuum provided α-hydroxyketone with 93% conversion and 82% GC yield. The optimized conditions were applied to a range of oleochemical diols, including a vegetable oil derivative, to obtain the corresponding α-hydroxyketones with up to 74% isolated yields.
Industrial resin "INDION 130" modified with vanadyl cations as highly efficient heterogeneous catalyst for epoxidation of fatty compounds with TBHP as oxidant
Khatri, Praveen K.,Aila, Mounika,Porwal, Jyoti,Kaul, Savita,Jain, Suman L.
, p. 5960 - 5965 (2015/08/18)
Industrial grade cation-exchange resin "INDION 130" was modified with vanadyl cations by an ion-exchange method and then used for the epoxidation of unsaturated fatty materials including acids, esters and vegetable oils using tert-butyl hydroperoxide (TBHP) in decane as oxidant. The effect of oxidant/double bond ratio, catalyst concentration, recycling of the catalyst and temperature on the conversion to epoxides was studied. After the epoxidation, the catalyst could easily be recovered by filtration and successfully reused for at least seven runs without any loss in catalytic activity.
Immobilized oxo-vanadium Schiff base on graphene oxide as an efficient and recyclable catalyst for the epoxidation of fatty acids and esters
Verma, Sanny,Aila, Mounika,Kaul, Savita,Jain, Suman L.
, p. 30598 - 30604 (2014/08/05)
Oxo-vanadium Schiff base was covalently immobilized onto chemically functionalized graphene oxide (GO) using 3-aminopropyltriethoxysilane as a coupler. The loading of vanadyl Schiff base onto GO nanosheets was confirmed by FTIR, XRD, TGA, and inductively coupled plasma-atomic emission spectroscopy (ICP-AES). The synthesized heterogeneous catalyst was found to be efficient and selective for the epoxidation of fatty acids and esters using t-butyl hydroperoxide (TBHP) as an oxidant. Interestingly, the immobilized catalyst showed a higher catalytic efficiency than the homogeneous vanadyl acetylacetonate. The recycling experiment results indicated that the catalyst was highly stable and maintained very high activity, and selectivity even after being used for six cycles. This journal is the Partner Organisations 2014.
Diesters from oleic acid: Synthesis, low temperature properties, and oxidation stability
Moser, Bryan R.,Sharma, Brajendra K.,Doll, Kenneth M.,Erhan, Sevim Z.
, p. 675 - 680 (2008/09/21)
Several diesters were prepared from commercially available oleic acid and common organic acids. The key step in the three step synthesis of oleochemical diesters entails a ring opening esterification of alkyl 9,10-epoxyoctadecanoates (alkyl: propyl, isopropyl, octyl, 2-ethylhexyl) using propionic and octanoic acids without the need for either solvent or catalyst. Each synthetic diester was evaluated for both low temperature operability and oxidation stability through measurement of cloud point, pour point, oxidation onset temperature, and signal maximum temperature. It was discovered that increasing chain length of the mid-chain ester and branching in the end-chain ester had a positive influence on the low temperature properties of diesters. Improved oxidation stability is achieved when the chain length of the mid-chain ester is decreased. Additionally, the mid-chain ester plays a larger role in oxidation stability than the end-chain ester. These products may prove useful in the search for bio-based industrial materials, such as lubricants, surfactants, and fuel additives.
