112-79-8Relevant academic research and scientific papers
Nickel-butadiene catalytic system for the cross-coupling of bromoalkanoic acids with alkyl grignard reagents: A practical and versatile method for preparing fatty acids
Iwasaki, Takanori,Higashikawa, Kiyokazu,Reddy, Vutukuri P.,Ho, Willbe W. S.,Fujimoto, Yukari,Fukase, Koichi,Terao, Jun,Kuniyasu, Hitoshi,Kambe, Nobuaki
, p. 2956 - 2960 (2013)
The knights who say Ni: A practical and convenient synthetic route to fatty acids involves the Ni-catalyzed alkyl-alkyl cross-coupling of bromoalkanoic acids and alkyl Grignard reagents in the presence of 1,3-butadiene as an additive (see scheme). Copyright
Optimizing reaction conditions for the isomerization of fatty acids and fatty acid methyl esters to their branch chain products
Reaume, Stephen J.,Ellis, Naoko
, p. 661 - 671 (2011)
In order to improve the oxidative stability and cold flow properties of oleic acid or methyl oleate, branch chain isomerization was conducted using a beta zeolite catalyst. Reaction conditions of temperature (200-300 °C), pressure (0.1-3.0 MPa), and co-catalyst (0-2 wt%) were optimized based on branch chain conversion and the cloud point of the ester following the isomerization reaction of oleic acid or methyl oleate. Fourier transform infrared spectroscopy (FTIR) and Gas Chromatograph equipped with Mass Spectrometry (GC/MS) analyses were used to analyze and quantify the isomerization product samples, while the cloud point of each sample was tested. The lowest and therefore, best cloud point measured was -15.2 °C at conditions of 200 °C, 3 MPa, and 2% co-catalyst using methyl oleate as a starting material. The highest branch chain conversion achieved was 50% under conditions of 300 °C, 1.5 MPa and 0% co-catalyst using oleic acid as a starting material. The use of oleic acid and methyl oleate is based on whether it is optimal to carry out the skeletal isomerization before or after the esterification reaction. Performing the isomerization reaction on the ester was preferred over the fatty acid based on the trans isomerization and cloud point results. Reducing the unbranched trans isomers was desirable in obtaining a low cloud point. AOCS 2010.
Homogeneous catalytic hydrogenation of lipids in aqueous dispersions and bacterial cell membranes with an efficient water-soluble Pd(II)-sulfosalan catalyst, Na2[Pd(HSS)]
Bunda, Szilvia,Gombos, Réka,Joó, Ferenc,Nagyházi, Brigitta
, (2020)
The recently synthesized water-soluble Na2[Pd(HSS)] (Na2HSS = hydrogenated sulfonated salen) was shown to be a non-toxic, active catalyst for modification of model and biomembranes by homogeneous catalytic hydrogenation. Hydrogenation of the unsaturated fatty acyl residues in soy-bean lecithin liposomes and in biomembranes of intact Pseudomonas putida F1 cells was accompanied by substantial cis-trans isomerization around the C[dbnd]C double bonds. The hydrogenations could be run in aqueous media under mild conditions (25 °C, 1 bar H2). Partial saturation (up to 10% conversion) of the membrane lipids of P. putida F1 did not damage the cells.
Hydrogenation of Oleic Acid to 9-Octadecen-1-ol with Rhenium-Tin Catalyst
Tang, Thin-Sue,Cheah, Kien-Yoo,Mizukami, Fujio,Niwa, Shu-ichi,Toba, Makoto,Choo, Yuen-May
, p. 601 - 605 (1993)
A new supported bimetallic catalyst, rhenium-tin, is able to reduce oleic acid to 9-octadecen-1-ol (cis and trans isomers) with appreciable yield under mild hydrogenation conditions.This paper reports investigations on the effects of catalyst preparation methods, types of support, catalyst raw materials, mole ratio of the metals, activation and reaction conditions on the activity and selectivity of the catalyst.Catalyst derived from the combination of ammonium perrhenate and stannic chloride on alumina gave the best performance, and the presence of tin in the catalyst is essential for the preservation of the olefinic bond of the oleic acid during hydrogenation.KEY WORDS: Hydrogenation, 9-octadecen-1-ol, oleic acid, rhenium-tin catalyst.
Catalytic hydrogenation of linoleic acid on nickel, copper, and palladium
Kitayama, Yoshie,Muraoka, Masahiro,Takahashi, Megumi,Kodama, Tatsuya,Itoh, Hirofumi,Takahashi, Eriko,Okamura, Mutsuo
, p. 1311 - 1316 (1996)
The catalytic activity and selectivity for hydrogenation of linoleic acid were studied on Ni, Cu, and Pd catalysts. A detailed analysis of the reaction product was performed by a gas-liquid chromatograph, equipped with a capillary column, and Fourier transform-infrared spectroscopy. Geometrical and positional isomerization of linoleic acid occurred during hydrogenation, and many kinds of linoleic acid isomers (trans-9,trans-12; trans-8,cis-12 or cis-9,trans-13; cis-9,trans-12; trans-9,cis-12 and cis-9,cis-12 18:2) were contained in the reaction products. The monoenoic acids in the partial hydrogenation products contained eight kinds of isomers and showed different isomer distributions on Ni, Cu, and Pd catalysts, respectively. The positional isomers of monoenoic acid were produced by double- bond migration during hydrogenation. On Ni and Pd catalysts, the yield of cis-12 and trans-12 monoenoic acids was larger than that of cis-9 and trans-9 monoenoic acids. On the contrary, the yield of cis-9 and trans-9 monoenoic acids was larger than that of cis-12 and trans-12 monoenoic acids on Cu catalyst. From these results, it is concluded that the double bond closer to the methyl group (Δ12) and that to the carboxyl group (Δ9) show different reactivity for hydrogenation on Ni, Cu, and Pd catalysts. Monoenoic acid formation was more selective on Cu catalyst than on Ni and Pd catalysts.
Electrochemical Proton Reduction over Nickel Foam for Z-Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes
Valiente, Alejandro,Martínez-Pardo, Pablo,Kaur, Gurpreet,Johansson, Magnus J.,Martín-Matute, Belén
, (2021/12/22)
Selective reduction strategies based on abundant-metal catalysts are very important in the production of chemicals. In this paper, a method for the electrochemical semihydrogenation and semideuteration of alkynes to form Z-alkenes was developed, using a simple nickel foam as catalyst and H3O+ or D3O+ as sources of hydrogen or deuterium. Good yields and excellent stereoselectivities (Z/E up to 20 : 1) were obtained under very mild reaction conditions. The reaction proceeded with terminal and nonterminal alkynes, and also with alkynes containing easily reducible functional groups, such as carbonyl groups, as well as aryl chlorides, bromides, and even iodides. The nickel-foam electrocatalyst could be recycled up to 14 times without any change in its catalytic properties.
Algicidal hydroxylated C18 unsaturated fatty acids from the red alga Tricleocarpa jejuensis: Identification, synthesis and biological activity
Ishibashi, Fumito,Kuwano, Kazuyoshi,Shibahara, Tomohiro,Zha, Shijiao
, (2020/06/05)
Bioassay-guided separation of a methanol extract of Tricleocarpa jejuensis by monitoring algicidal activity against the red tide phytoplankton Chattonella antiqua led to the isolation of an active fraction consisting of a mixture of four isomeric compounds. The active compounds were identified as (E)-9-hydroxyoctadec-10-enoic acid (1), (E)-10-hydroxyoctadec-8-enoic acid (2), (E)-11-hydroxyoctadec-12-enoic acid (3) and (E)-12-hydroxyoctadec-10-enoic acid (4) by NMR, IR and mass spectral data. The structures were confirmed by comparison of the NMR and MS data with those of authentic samples of 1–4 obtained by unambiguous syntheses. Synthesized hydroxy acids 1–4 and related compounds were assessed for algicidal activity against C. antiqua and it was found that all of 1–4 had high activity (>80% mortality at 24 h) at a concentration of 20 μg/mL. A structure–activity relationship study using 11 related compounds revealed that the presence of the hydroxyl group is important for the activity and the double bond may be replaced with a triple bond.
Production of ethylene glycol from direct catalytic conversion of cellulose over a binary catalyst of metal-loaded modified SBA-15 and phosphotungstic acid
Yu, Shitao,Cao, Xincheng,Liu, Shiwei,Li, Lu,Wu, Qiong
, p. 24857 - 24865 (2018/07/29)
This study presents the utilization of a binary catalyst composed of metal-loaded modified SBA-15 (M/SBA-15) and phosphotungstic acid (H3PW12O40) for ethylene glycol (EG) production from direct catalytic conversion of cell
METHOD FOR SYNTHESISING BIOBASED UNSATURATED ACIDS
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Paragraph 0093-0099, (2015/12/07)
The invention relates to a method for preparing a compound of formula (I), wherein n is an integer from 1 to 21,said method comprises reacting a light olefin fraction, in the presence of a metathesis catalyst, with a compound having from 10 to 24 carbon atoms, of the following formula (II): wherein, n is an integer from 1 to 21,R corresponds to a hydrogen atom or an alkyl or alkenyl chain from 1 to20 carbon atoms optionally substituted by at least one hydroxyl group, said compound of formula (II) being used alone or in a mixture of compounds of formula (II).
Method of producing dicarboxylic acids
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Page/Page column 11; 13, (2009/05/29)
A method of producing dicarboxylic acids (e.g., α,ω dicarboxylic acids) by reacting a compound having a terminal COOH (e.g., unsaturated fatty acid such as oleic acid) and containing at least one carbon-carbon double bond with a second generation Grubbs catalyst in the absence of solvent to produce dicarboxylic acids. The method is conducted in an inert atmosphere (e.g., argon, nitrogen). The process also works well with mixed unsaturated fatty acids obtained from soybean, rapeseed, tall, and linseed oils.
