20221-27-6Relevant academic research and scientific papers
Branched alkyl sulfonate anionic surfactant and preparation process thereof
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Paragraph 0090-0091, (2021/02/10)
The invention discloses a branched alkyl sulfonate anionic surfactant and a preparation process thereof, and belongs to the field of fine chemical surfactants. The method comprises the steps of (1) conducting a esterification carboxyl-terminated reaction, specifically, catalyzing oleic acid or linoleic acid and fatty alcohol to be subjected to esterification reaction by adopting organic acid as acatalyst to prepare an alkyl oleate or alkyl linoleate compound; and (2) conducting a double bond addition sulfonation reaction, specifically, in the presence of the catalyst, carrying out sulfonationreaction with the alkyl oleate compound or the alkyl linoleate compound obtained in the step (1) by taking low-carbon alcohol and deionized water as solvents and sodium hydrogen sulfite as a sulfonation reagent to prepare the branched alkyl sulfonate anionic surfactant. The synthesized branched alkyl sulfonate anionic surfactant product can effectively reduce the surface tension of an aqueous solution, and is good in solubility, large in initial foaming amount, high in defoaming speed and excellent in surfactant performance. The method has the advantages of simple process operation, few sidereactions, energy saving and environmental protection.
The Reaction of Thiyl Radical with Methyl Linoleate: Completing the Picture
Chatgilialoglu, Chryssostomos,Ferreri, Carla,Guerra, Maurizio,Samadi, Abdelouahid,Bowry, Vincent W.
supporting information, p. 4704 - 4714 (2017/04/11)
Cis lipids can be converted by thiols and free radicals into trans lipids, which are therefore a valuable tell-tale for free radical activity in the cell’s lipidome. Our previous studies have shown that polyunsaturated lipids are isomerized by alkanethiyl radicals (S?) in a cycle propagated by reversible double-bond addition and terminated by radical H-abstraction from the lipid. A critical flaw in this picture has long been that the reported lipid abstraction rate from radiolysis studies is faster than addition-isomerization, implying that the “cycle” must be terminating faster than it is propagating! Herein, we resolved this longstanding puzzle by combining a detailed product analysis, with reinvestigation of the time-resolved kinetics, DFT calculations of the indicated pathways, and reformulation of the radical-stasis equations. We have determined thiol-coupled products in dilute solutions arise mainly from addition to the inside position of the bisallylic group, followed by rapid intramolecular H? transfer, yielding allylic radicals (LZZ + S? ? SL? → SL′?) that are slowly reduced by thiol (SL′? + SH → SL′H + S?). The first-order grow-in rate of the L-H? signal (kexp280nm) may therefore be dominated by the addition-H-translocation rather than slower direct H?-abstraction. Steady-state kinetic analysis of the new mechanism is consistent with products and the rates and trends for polyunsaturated fatty acids (PUFAs), monounsaturated fatty acids (MUFAs), and mixtures, with and without physiological [O2]. Implications of this new paradigm for the thiol-ene reactivity fall in an interdisciplinary research area spanning from synthetic applications to metabolomics.
Metathesis of renewable polyene feedstocks – Indirect evidences of the formation of catalytically active ruthenium allylidene species
Kovács, Ervin,Sághy, Péter,Turczel, Gábor,Tóth, Imre,Lendvay, Gy?rgy,Domján, Attila,Anastas, Paul T.,Tuba, Róbert
supporting information, p. 213 - 217 (2017/09/12)
Cross-metathesis (CM) of conjugated polyenes, such as 1,6-diphenyl-1,3,5-hexatriene (1) and α-eleostearic acid methyl ester (2) with several olefins, including 1-hexene, dimethyl maleate and cis-stilbene as model compounds has been carried out using (1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)-dichloro(o-isopropoxyphenylmethylene)ruthenium (Hoveyda-Grubbs 2nd generation, HG2) catalyst. The feasibility of these reactions is demonstrated by the observed high conversions and reasonable yields. Thus, regardless of the relatively low electron density, =CH–CH= conjugated units of molecules, including compound 2 as a sustainable, non-foodstuff source, can be utilized as building blocks for the synthesis of various value-added chemicals via olefin metathesis. DFT-studies and the product spectrum of the self-metathesis of 1,6-diphenyl-1,3,5-hexatriene suggest that a Ru η1-allylidene complex is the active species in the reaction.
Antiproliferative activity of synthetic fatty acid amides from renewable resources
Dos Santos, Daiane S.,Piovesan, Luciana A.,D'Oca, Caroline R. Montes,Hack, Carolina R. Lopes,Treptow, Tamara G.M.,Rodrigues, Marieli O.,Vendramini-Costa, Débora B.,Ruiz, Ana Lucia T.G.,De Carvalho, Jo?o Ernesto,D'Oca, Marcelo G. Montes
, p. 340 - 347 (2015/02/02)
In the work, the in vitro antiproliferative activity of a series of synthetic fatty acid amides were investigated in seven cancer cell lines. The study revealed that most of the compounds showed antiproliferative activity against tested tumor cell lines, mainly on human glioma cells (U251) and human ovarian cancer cells with a multiple drug-resistant phenotype (NCI-ADR/RES). In addition, the fatty methyl benzylamide derived from ricinoleic acid (with the fatty acid obtained from castor oil, a renewable resource) showed a high selectivity with potent growth inhibition and cell death for the glioma cell line - the most aggressive CNS cancer.
ADDUCTS OF LEVULINIC DERIVATIVES WITH EPOXIDIZED FATTY ACID ESTERS AND USES THEREOF
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Page/Page column 19-20, (2010/11/27)
The present disclosure relates to methods of preparation of compounds resulting from the reaction of levulinic esters and epoxidized unsaturated fatty acid esters. The compounds are useful as renewable biomass-based plasticizers for a variety of polymers. Mono-, di- and tri-ketal adducts formed in a reaction between alkyl esters of levulinate and epoxidized unsaturated fatty acid esters derived from vegetable oils are also disclosed.
Factors influencing the autoxidation of fatty acids: Effect of olefin geometry of the nonconjugated diene
Tallman, Keri A.,Roschek Jr., Bill,Porter, Ned A.
, p. 9240 - 9247 (2007/10/03)
Autoxidations of cis,cis, cis,trans, and trans,trans nonconjugated octadecadienoates and pentadecadienes were carried out in the presence of α-tocopherol to investigate the effect of olefin geometry on this oxidation process and provide insight into the factors that influence the autoxidation of fatty acids. We have found that as the trans character of the diene increases, the amount of O2 trapping at the central (bis-allylic) position of the pentadienyl radical also increases. In addition, the rate constant for β-fragmentation (kβ ≈ 10 6 s-1) of the bis-allylic peroxyl radical decreased on going from the cis,cis to the trans,trans diene. We have also found that for the cis,trans nonconjugated dienes, there is a preference for trapping of the pentadienyl radical by O2 at the transoid end, generating the cis,trans conjugated hydroperoxide as the major product.
Cis-trans isomerization of polyunsaturated fatty acid residues in phospholipids catalyzed by thiyl radicals
Ferreri,Costantino,Perrotta,Landi,Mulazzani,Chatgilialoglu
, p. 4459 - 4468 (2007/10/03)
Phospholipids containing trans-unsaturated fatty acid residues are the major products of the thiyl radical attack on L-α-phosphatidylcholine from soybean lecithin in homogeneous solution or in liposomes (LUVET). Thiyl radicals act as the catalyst for the cis-trans isomerization, and the number of catalytic cycles depends on the reaction conditions. The presence of ～0.2 mM oxygen does not influence the reaction outcome but accelerates the efficiency of cis-trans isomerization in homogeneous solution. Under these conditions, the PUFA peroxidation is found to be unimportant. A detailed study of the isomerization of methyl linoleate including product studies indicates the formation of a small amount of conjugated dienes that act as inhibitors. Indeed, all-trans-retinol substantially retarded the isomerization process.
Synthesis of (9Z,12E)- and (9E,12Z)-[1-14C]linoleic acid and (5Z,8Z,11Z,14E)-[1-14C]arachidonic acid
Berdeaux,Vatele,Eynard,Nour,Poullain,Noel,Sebedio
, p. 71 - 80 (2007/10/03)
(3Z,6E)-1-Bromododeca-3,6-diene, a common intermediate in the synthesis of labelled 12t linoleic acid and 14t arachidonic acid, was obtained from (E)-3-nonyl-1-ol: in four steps, via conventional functional manipulations. Cross-coupling of this bromododecadiene with the Grignard reagent of 1-chloro-5-(tetrahydropyranyloxy)pentane gave a C17 dienic ether which was further transformed in three steps to 12t-[l-14C]linoleic acid in 22% overall yield from 3-nonyl-1-ol (eight steps). The synthesis of 14t arachidonic acid involves a Wittig reaction between (Z)-7-(t-butyldiphenylsilyloxy)hept-3-enal and the ylide of (3Z,6E)-dodeca-3,6-dienyl-triphenylphosphonium bromide. The resulting C19 tetraenic ether was transformed in three steps to 14t [l-14C]arachidonic acid (isomeric and radiochemical purities > 99%). 9t Linoleic acid was obtained by a stepwise six-carbon elongation chain of both ends of(E)-6-(2-tetrahydropyranyloxy)-hex-3-enyltriphenylphosphonium salt in 20% overall yield.
Autoxidation of Polyunsaturated Fatty Acids, an Expanded Mechanistic Study
Porter, Ned A.,Wujek, Dennis G.
, p. 2626 - 2629 (2007/10/02)
The autoxidation of four isomeric methyl 9,12-octadecadienoates in benzene/1,4-cyclohexadiene has been investigated.Autoxidation of the isomers 9-Z,12-Z (methyl linoleate); 9-Z,12-E;9-E,12-Z; and 9-E,12-E (methyl linoelaidate) octadecadienoates was studied.With no cyclohexadiene or with low cyclohexadiene solvent composition, the distribution of product hydroperoxides from the various isomeric precursors was equivalent or nearly so.With higher cyclohexadiene solvent composition, the product mixtures became nonequivalent and reflected the stereochemistry of the particular diene precursor.A steady-state and iterative computer kinetic analysis is reported, and a scheme for diene fatty acid autoxidation involving reversible oxygen addition to intermediate pentadienyl carbon radicals is proposed.
An Electron Spin Resonance Study of Fatty Acids and Esters. Part 1. Hydrogen Abstraction from Olefinic and Acetylenic Long-chain Esters
Bascetta, Emanuele,Gunstone, Frank D.,Walton, John C.
, p. 603 - 614 (2007/10/02)
The radicals generated from unsaturated fatty acid esters by hydrogen abstraction with photochemically formed t-butoxyl radicals have been investigated by e.s.r. spectroscopy.The substituted allyl and pentadienyl radicals generated from monoenoic and dienoic esters were conformationally stable under the conditions of the experiments.The main species observed on hydrogen-abstraction from monoynoic esters were substituted propynyl radicals, and the same radical type was generated from diynoic esters with more than one methylene unit separating the triple bonds.Substituted penta-1,4-diynyl and penta-1,3-diynyl radicals were identified on hydrogen-abstraction from methylene-interrupted and conjugated diynoic esters.Hydrogen abstraction from triacylglycerols containing one or more double bonds was also examined.Most of the unsaturated esters also gave rise to secondary radicals produced by hydrogen-abstraction from the chain methylene groups.From the measured concentrations of the secondary and delocalised radicals the following approximate relative rates of hydrogen-abstraction by t-butoxyl radicals from the different sites were obtained: secondary: propynylic: allylic: bisallylic = 1:18:36:116 at 293 K.
