- Synthesis of fatty monoester lubricant base oil catalyzed by Fe-Zn double-metal cyanide complex
-
Fatty monoester lubricant base oils as high as 96.7 mol% were prepared by reacting methyl oleate with long-chain alcohols viz., 2-ethyl-1-hexanol (C 8-OH), 1-decanol (C10OH) and 1-dodecanol (C 12OH) in the presence of a solid Fe-Zn double-metal cyanide (DMC) complex catalyst. Unlike many other acid catalysts, DMC doesn't produce undesired ether side products. The catalyst was reusable in four recycling experiments with little loss in catalytic activity and ester yield. The long-chain esters prepared in the study have the desired physical properties for their application as lubricant base oils.
- Raut, Ravindra K,Shaikh, Mehejabeen,Darbha, Srinivas
-
-
Read Online
- Novel Ester Compounds, Method for the Production Thereof and Use Thereof
-
The invention relates to novel ester compounds of the general formula (I) to a process for preparation thereof and to the use thereof. These ester compounds may contain a mixture of at least two compounds of the general formula (I).
- -
-
Paragraph 0097-0098; 0099-0106
(2020/05/29)
-
- Homogeneous and heterogeneous catalytic (dehydrogenative) oxidation of oleochemical 1,2-diols to α-hydroxyketones
-
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.
- Vu, Nam Duc,Guicheret, Boris,Duguet, Nicolas,Métay, Estelle,Lemaire, Marc
-
p. 3390 - 3399
(2017/07/28)
-
- Production of Valuable Esters from Oleic Acid with a Porous Polymeric Acid Catalyst without Water Removal
-
We demonstrate the use of porous phenolsulfonic acid-formaldehyde (PSF) resins as solid-acid catalysts, which showed excellent performance in the esterification of fatty acids without using any solvent or introducing a water-removal process. The catalyst was reused up to 30 times without significant loss of activity.
- Kim, Yo-Han,Han, Jusung,Jung, Byeong Yeon,Baek, Heeyoel,Yamada, Yoichi M. A.,Uozumi, Yasuhiro,Lee, Yoon-Sik
-
supporting information
p. 29 - 32
(2015/12/26)
-
- Guanidine based task specific ionic liquids for the synthesis of biolubricant range esters under solvent-free condition
-
Guanidine-based task specific ionic liquids (ILs) were synthesized from the reaction of 1,1,3,3-tetramethyl guanidine with protic acids and used for the synthesis of higher alcohol esters of fatty acids as biolubes under solvent free condition. The synthesized 1,1,3,3-tetramethylguanidinium hydrogen sulphate (TMG·HSO4) was found to be most effective among the different ILs including 1,1,3,3-tetramethylguanidinium acetate (TMG·Ac), 1,1,3,3-tetramethylguanidinium hydrogen phosphate (TMG·H2PO4) and 1,1,3,3-tetramethylguanidinium trifluoro acetate (TMG·TFA). The effect of various reaction parameters such as reaction temperature, reaction time, catalyst amount etc. has been studied. After completion the reaction the esterification product was isolated and the recovered IL was reused for several runs without loss in catalytic activity.
- Porwal, Jyoti,Kumar, Subodh,Kaul, Savita,Jain, Suman L.
-
p. 93640 - 93644
(2016/10/18)
-
- Diesters from oleic acid: Synthesis, low temperature properties, and oxidation stability
-
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.
- Moser, Bryan R.,Sharma, Brajendra K.,Doll, Kenneth M.,Erhan, Sevim Z.
-
p. 675 - 680
(2008/09/21)
-
- Improvement in the gas chromatographic resolution of petroselinate from oleate
-
In the extraction of oils from seeds of the genus Coriandrum, GC separations of petroselinate from oleate often gave poor resolution of these two isomers. Oleic and petroselinic acids were esterified with a series of alcohols (methanol, ethanol, 1 propanol, 2-propanol, 2-methyl-1 -propanol, 1 -butanol, 3-methyl1-butanol, and 2-ethyl-1-hexanol). GC resolution of the A6 from the Δ9 and Δ11 octadecenoates was examined for all ester derivatives on a polar phase column. The Δ6 and Δ9 isomers were unresolved as methyl esters; however, the 2-ethyl-1-hexyl esters gave baseline separation of all three isomers under temperature programming conditions. When isothermal conditions were optimized for each ester, separation of these isomers was possible with good resolution values (>89%) for all the alcohols except methanol, which had a partial resolution of 51%. The rates of esterification of all the alcohols were determined for reactions with both oleic acid and triolein using potassium hydroxide as the esterification catalyst. Methanol gave the largest rate constant in both acid and oil esterification reactions with a rate constant 10-fold better than all of the other alcohols. Based on rates of reaction, resolution of petroselinate from oleate, and removal of residual alcohol, the ethyl ester derivative appears to be the best choice for seed oils containing petroselinic acid. Copyright
- Isbell, Terry A.,Green, Lindsay A.,DeKeyser, Stephanie S.,Manthey, Linda K.,Kenar, James A.,Cermak, Steven C.
-
p. 429 - 434
(2007/10/03)
-
- WAX COMPOSITION OF SARGASSUM FULVELLUM
-
Sixty-seven compounds were characterized in the wax of Sargassum fulvellum.Characteristic components were the 5-methylhexyl esters of octanoic, decanoic, lauric, myristic, palmitic, palmitoleic, stearic, oleic, linoleic and linolenic, and the 2-ethylhexyl esters of the same acids.The wax of S. fulvellum contains hydrocarbons (1.6percent), esters (21.8percent), free acids (74.9percent) and free alcohols (0.3percent).The principal free alcohols range in chain length only from C6 to C7. - Key Word Index: Sargassum fulvellum; Sargassaceae; Phaeophyta; wax; 5-methylhexyl esters; 2-ethylhexyl esters; 5-methylhexanol; 2-ethylhexanol.
- Miyazawa, Mitsuo,Uematsu, Tosihisa,Kameoka, Hiromu
-
p. 1788 - 1791
(2007/10/02)
-
