scholarly journals Consecutive reactions in an oleic acid and acetic anhydride reaction medium

2009 ◽  
Vol 111 (7) ◽  
pp. 723-729 ◽  
Author(s):  
Jerome Peydecastaing ◽  
Carlos Vaca-Garcia ◽  
Elisabeth Borredon
Keyword(s):  
Oleic Acid ◽  
Acetic Anhydride ◽  
Reaction Medium ◽  
Consecutive Reactions

scholarly journals Conversion of Oleic Acid into Azelaic and Pelargonic Acid by a Chemo-Enzymatic Route

Molecules ◽  
2020 ◽  
Vol 25 (8) ◽  
pp. 1882 ◽  
Author(s):  
Elisabetta Brenna ◽  
Danilo Colombo ◽  
Giuseppe Di Lecce ◽  
Francesco G. Gatti ◽  
Maria Chiara Ghezzi ◽  
...  
Keyword(s):  
Oleic Acid ◽  
Azelaic Acid ◽  
Atmospheric Oxygen ◽  
Reaction Medium ◽  
Chemical Oxidation ◽  
Pelargonic Acid ◽  
Dihydroxystearic Acid ◽  
Chemical Purity ◽  
Enzymatic Route

A chemo-enzymatic approach for the conversion of oleic acid into azelaic and pelargonic acid is herein described. It represents a sustainable alternative to ozonolysis, currently employed at the industrial scale to perform the reaction. Azelaic acid is produced in high chemical purity in 44% isolation yield after three steps, avoiding column chromatography purifications. In the first step, the lipase-mediated generation of peroleic acid in the presence of 35% H2O2 is employed for the self-epoxidation of the unsaturated acid to the corresponding oxirane derivative. This intermediate is submitted to in situ acid-catalyzed opening, to afford 9,10-dihydroxystearic acid, which readily crystallizes from the reaction medium. The chemical oxidation of the diol derivative, using atmospheric oxygen as a stoichiometric oxidant with catalytic quantities of Fe(NO3)3∙9∙H2O, (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO), and NaCl, affords 9,10-dioxostearic acid which is cleaved by the action of 35% H2O2 in mild conditions, without requiring any catalyst, to give pelargonic and azelaic acid.

scholarly journals Keggin-Type Heteropolyacid for Ring-Opening Polymerization of Cyclohexene Oxide: Molecular Weight Control

2015 ◽  
Vol 2015 ◽  
pp. 1-6 ◽  
Author(s):  
Ahmed Aouissi ◽  
Zeid Abdullah Al-Othman ◽  
Abdurrahman Salhabi
Keyword(s):  
Molecular Weight ◽  
Reaction Time ◽  
Acetic Anhydride ◽  
Ring Opening ◽  
Weight Control ◽  
Reaction Medium ◽  
Resonance Spectroscopy ◽  
Cyclohexene Oxide ◽  
Scanning Calorimetry ◽  
Catalyst Amount

Polymerization of 1,2-cyclohexene oxide (CHO) in dichloromethane was catalyzed by 12-tungstophosphoric acid (H3PW12O40·13H2O) as a super solid acid. The effect of polymerization parameters such as reaction time, temperature, and catalyst amount was investigated. The effect of acetic anhydride as a ring-opening agent was also investigated. The resulting poly(1,2-cyclohexene oxide) (PCHO) was characterized by Fourier transform infrared (FTIR), nuclear magnetic resonance spectroscopy (1HNMR), gel-permeation chromatography (GPC), and differential scanning calorimetry (DSC). It has been found that the PCHO prepared over H3PW12O40·13H2O has a stereoregularity higher than that prepared over clay and Aluminium alkoxide catalysts. TheTgvalue obtained is due to the microstructure but not to molecular weight. The yield and the molecular weight of the polymer depend strongly on the reaction conditions. Molecular weights can be readily controlled by changing reaction temperature, reaction time, and catalyst amount. Contrary to most polymerization reactions, the molecular weight increases with the temperature increase. Addition of acetic anhydride to the reaction medium increased the yield threefold.

scholarly journals Continuous Catalyst-Free Esterification of Oleic Acid in Compressed Ethanol

2014 ◽  
Vol 2014 ◽  
pp. 1-5 ◽  
Author(s):  
Ana Carolina de Araujo Abdala ◽  
Vitor Augusto dos Santos Garcia ◽  
Caroline Portilho Trentini ◽  
Lúcio Cardozo Filho ◽  
Edson Antonio da Silva ◽  
...  
Keyword(s):  
Oleic Acid ◽  
Residence Time ◽  
Tubular Reactor ◽  
Reaction Medium ◽  
Ethyl Esters ◽  
Molar Ratio ◽  
Molar Ratios ◽  
Catalyst Free ◽  
Free Process ◽  
Positive Effect

The esterification of oleic acid in a continuous catalyst-free process using compressed ethanol was investigated in the present study. Experiments were performed in a tubular reactor and variables investigated were temperature, pressure, and oleic acid to ethanol molar ratio for different residence time. Results demonstrated that temperature, in the range of 473 K to 573 K, and pressure had a positive effect on fatty acid ethyl esters (FAEE) production. In the experimental range investigated, high conversions can be obtained at low ethanol concentrations in the reaction medium and it was observed that oleic acid to ethanol molar ratios greater than 1 : 6 show no significant increase in conversion. Nonnegligible reaction conversions (>90%) were achieved at 573 K, 20 MPa, oleic acid to ethanol molar ratio of 1 : 6, and 20 minutes of residence time.

scholarly journals Multi-Step Enzymatic Synthesis of 1,9-Nonanedioic Acid from a Renewable Fatty Acid and Its Application for the Enzymatic Production of Biopolyesters

Polymers ◽  
2019 ◽  
Vol 11 (10) ◽  
pp. 1690
Author(s):  
Lee ◽  
Kang ◽  
Kim ◽  
Seo ◽  
Pyo ◽  
...  
Keyword(s):  
Oleic Acid ◽  
Immobilized Lipase ◽  
Diphenyl Ether ◽  
Average Molecular Weight ◽  
Reaction Medium ◽  
Building Blocks ◽  
Biological Synthesis ◽  
Enzymatic Production ◽  
Nonanedioic Acid ◽  
Long Chain

1,9-Nonanedioic acid is one of the valuable building blocks for producing polyesters and polyamides. Thereby, whole-cell biosynthesis of 1,9-nonanedioic acid from oleic acid has been investigated. A recombinant Corynebacterium glutamicum, expressing the alcohol/aldehyde dehydrogenases (ChnDE) of Acinetobacter sp. NCIMB 9871, was constructed and used for the production of 1,9-nonanedioic acid from 9-hydroxynonanoic acid, which had been produced from oleic acid. When 9-hydroxynonanoic acid was added to a concentration of 20 mM in the reaction medium, 1,9-nonanedioic acid was produced to 16 mM within 8 h by the recombinant C. glutamicum. The dicarboxylic acid was isolated via crystallization and then used for the production of biopolyester by a lipase. For instance, the polyesterification of 1,9-nonanedioic acid and 1,8-octanediol in diphenyl ether by the immobilized lipase B from Candida antarctica led to formation of the polymer product with the number-average molecular weight (Mn) of approximately 21,000. Thereby, this study will contribute to biological synthesis of long chain dicarboxylic acids and their application for the enzymatic production of long chain biopolyesters.

Synthesis and Characterization of the Water-Soluble Oleoyl Acetyl Chitosan

2011 ◽  
Vol 284-286 ◽  
pp. 1782-1785
Author(s):  
Wei Chang Ke ◽  
Yi Kun Chen ◽  
Guo Xi Xiong ◽  
Xiang Hong Peng ◽  
Chao Zhu ◽  
...  
Keyword(s):  
Oleic Acid ◽  
Acetic Anhydride ◽  
Chemical Structure ◽  
Water Soluble ◽  
Synthesis And Characterization ◽  
Nmr Spectrum ◽  
Ft Ir ◽  
Oleoyl Chloride ◽  
C Nmr

Oleoyl chloride was synthesized by oleic acid and thionyl dichloride (SOCl2), and then reacted with chitosan in dichloromethane to obtain the oleoyl chitosan. Novel water-soluble oleoyl acetyl chitosan (OACh) was synthesized using oleoyl chloride reacted with acetic anhydride in pyridine. The chemical structure of the OACh was characterized by FT-IR, 1H and 13C NMR. There existed the peaks at 1743.9 cm-1 (C=O) and 1658.1 cm-1(C=C) in FT-IR spectrum, and the peaks at 170.8, 171.6 and 172.5 ppm which were assigned to the C=O of the oleoyl and acetyl groups in 13C NMR spectrum. The results indicated that OACh had oleoyl as hydrophobic moieties and acetyl as hydrophilic moieties.

Solvent-free catalytic deoxygenation of oleic acid via nano-Ni/HZSM-5: Effect of reaction medium and coke characterization

2018 ◽  
Vol 179 ◽  
pp. 324-333 ◽  
Author(s):  
Shiyou Xing ◽  
Pengmei Lv ◽  
Che Zhao ◽  
Ming Li ◽  
Lingmei Yang ◽  
...  
Keyword(s):  
Oleic Acid ◽  
Reaction Medium ◽  
Solvent Free ◽  
Coke Characterization ◽  
Catalytic Deoxygenation

scholarly journals Synthesis of some pyrazolo[3,4-d]pyrimidines and their fused triazole and tetrazole derivatives

1999 ◽  
Vol 64 (11) ◽  
pp. 655-662 ◽  
Author(s):  
Samira Swelam ◽  
Abd El-Salam ◽  
Magdi Zaki
Keyword(s):  
Acetic Anhydride ◽  
Formic Acid ◽  
Hydrazine Hydrate ◽  
Carbon Disulfide ◽  
Nitrous Acid ◽  
Reaction Medium ◽  
Pyrimidine Derivatives ◽  
Elemental Analyses ◽  
Tetrazole Derivatives

Reaction of 2 with different reagents, namely formic acid, acetic anhydride and trichloroacetonitrile, yielded pyrazolo[3,4-d]pyrimidine derivatives 3, 5 and 6, respectively. Pyrazolo[3,4-d]pyrimidine m-thiazine(7) and 2,4-(1H,3H)dithione (8) derivatives were formed by the action of carbon disulfide on 2, depending on the reaction medium. Interaction of 7 with hydrazine hydrate yielded the aminoimino derivative 9 which reacted with acetic anhydride, triethyl orthoacetate and/or appropriate aldehydes to give 11, 12 and 13a,b, respectively. Methylation of compound 8 gave 14, which reacted with hydrazine hydrate to afford the monohydrazino derivative 15. Reaction of 15, with formic acid and nitrous acid afforded pyrazolo[4,3-e]triazolo[1,5-c]pyrimidine (16) and pyrazolo[4,3-e]tetrazolo-[1,5-c]pyrimidine (17) derivatives, respectively. The structures of products 3-17 were identified in light of their elemental analyses and spectra data.

scholarly journals Aldol Condensation of Furfural with Acetone Over Mg/Al Mixed Oxides. Influence of Water and Synthesis Method

Catalysts ◽  
2019 ◽  
Vol 9 (2) ◽  
pp. 203 ◽  
Author(s):  
Almudena Parejas ◽  
Daniel Cosano ◽  
Jesús Hidalgo-Carrillo ◽  
José Ruiz ◽  
Alberto Marinas ◽  
...  
Keyword(s):  
Active Sites ◽  
Mixed Oxides ◽  
Aldol Condensation ◽  
Condensation Product ◽  
Synthesis Method ◽  
Reaction Medium ◽  
Initial Step ◽  
Consecutive Reactions ◽  
Influence Of Water ◽  
Partial Blocking

Aldol condensation of furfural and acetone (an important initial step to obtain diesel from biomass) was studied over MgAl mixed oxides. The influence of the utilization of microwaves and/or a surfactant (Pluronic 123) during the synthesis as well as the use of water (either pre-hydrating the solids before catalytic studies or in water/toluene mixtures as the reaction medium) is discussed. The combined use of Pluronic 123 and microwaves led to solids with bigger pore sizes, exhibiting lower basicity and higher acidity than the conventional synthetic method, thus resulting in an increase in the yield of the desired product of condensation, comprising two molecules of furfural and one of acetone (F2Ac). As for the influence of water, re-hydration of the mixed oxides was detrimental to activity, probably as a result of the partial blocking (solvation) of active sites. On the contrary, the increase in water percentage in the reaction medium resulted in higher conversions, though selectivity to F2Ac decreased. The weakening of the C=O bond of furfural in the presence of water as well as the higher solubility of the first condensation product (FAc) in toluene, as compared to water, could account for that. A 44.5% yield of F2Ac (66% conversion) after 16 h was obtained with the most active solid, which maintained the activity for three consecutive reactions.

Indolizines. III. Studies on the acylative cyclization of stabilized Methylene-1,2-dihydropyridines. A novel synthesis of 3-phenyl-1,2-phthaloylindolizines

1972 ◽  
Vol 25 (7) ◽  
pp. 1549 ◽  
Author(s):  
I Dainis
Keyword(s):  
Acetic Anhydride ◽  
Mass Spectra ◽  
Benzyl Chloride ◽  
Reaction Medium ◽  
Phenacyl Bromide ◽  
Ethyl Chloroformate ◽  
Novel Synthesis ◽  
Aqueous Base

Cyclization of l-benzyl-2-ethoxycarbonylmethylene-1,2-dihydropyridine in acetic anhydride is shown to depend on the basicity of the reaction medium. The reaction between activated 2-methylpyridinium salts and ethyl chloroformate in aqueous base has provided a novel synthesis of 2-ethoxycarbonyl-methylene-l,2-dihydropyridines. Nass spectra of four 2-methylene-l,2-dihydropyridines are presented together with N.M.R. evidence for their 2-E configuration. Pyrophthalone (15) reacted with benzyl chloride in boiling nitrobenzene to give 2-benzylpyrophthalone. With phenacyl bromide, pyrophthalone gave 3-phenyl-1,2-phthaloylindolizine (6-phenylbenzo[f]pyrido[1,2-a]isoindole-7,12-dione) rather than the 3-benzoylindolizine (18). Quinophthalone reacted similarly, and the formation of both phthaloylindolizines has been attributed to a novel rearrangement of the 2-phenacylindan-l,3-dione system in the intermediate, alkylated products. Mass spectra of both phthalones and three phthaloylindolizines are presented.

scholarly journals Determination of Free Fatty Acid by FT-NIR Spectroscopy in Esterification Reaction for Biodiesel Production

2013 ◽  
Vol 2013 ◽  
pp. 1-5 ◽  
Author(s):  
Djéssica Tatiana Raspe ◽  
Camila da Silva
Keyword(s):  
Oleic Acid ◽  
Soybean Oil ◽  
Multivariate Calibration ◽  
Reaction Medium ◽  
Reference Method ◽  
Nir Spectroscopy ◽  
Biodiesel Production ◽  
Esterification Reaction ◽  
Experimental Conditions ◽  
Batch Mode

This work reports the use of FT-NIR spectroscopy coupled with multivariate calibration to determine the percentage of free fatty acids (FFA) in samples obtained by the esterification of FFA in vegetable oils. The analytical method used as calibration matrix samples of the reaction medium of esterification of oleic acid in soybean oil in proportions of 0.3 to 40 wt% (by weight) of oleic acid obtained under different experimental conditions and utilized the partial least squares (PLS) regression. The efficiency of the method was tested to predict the content of FFA in reactions of esterification of oleic acid in soybean oil catalysed by KSF clay and Amberlyst 15 commercial resin, both in a batch mode. Good Correlations were observed between the FT-NIR/PLS method and the reference method (AOCS). The results confirm that FT-NIR spectroscopy, in combination with multivariate calibration, is a promising technique for monitoring esterification reaction for biodiesel production.

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