scholarly journals Low-Temperature Esterification to Produce Oleic Acid-Based Wax Esters Catalyzed by 4-Dodecylbenzenesulfonic Acid

Catalysts ◽  
2021 ◽  
Vol 11 (12) ◽  
pp. 1471
Author(s):  
Zhenzhen Li ◽  
Wei Liu ◽  
Guolong Yang
Keyword(s):  
Oleic Acid ◽  
Low Temperature ◽  
Inhibitory Effect ◽  
Wax Esters ◽  
Molar Ratio ◽  
Efficient Catalyst ◽  
Dodecylbenzenesulfonic Acid ◽  
Effect Of Water ◽  
Solvent Free Conditions ◽  
Increasing Temperature

Synthesized oleic acid-based wax esters (e.g., cetyl oleate), which can replace spermaceti oil or jojoba oil, have been widely used in the cosmetic, pharmaceutical and other industries. In this work, 4-dodecylbenzenesulfonic acid (DBSA) has been successfully used as an efficient catalyst to synthesize oleic acid-based wax esters through esterification at 40 °C under solvent-free conditions. A 93.6% conversion rate of cetyl alcohol was obtained under optimal conditions: 10 mol% DBSA, a molar ratio of 1.3:1 oleic acid to alcohol, a reaction temperature 40 °C and a reaction time of 4 h. The effect of water content on esterification was investigated, and it was found that the inhibitory effect of water decreased significantly with increasing temperature. Moreover, DBSA-catalyzed esterification could be applied in the production of various oleic acid-based wax esters and excellent conversion (>90%) to esters was obtained under such mild conditions. DBSA-catalyzed low-temperature esterification is an efficient method for the production of liquid wax esters.

Studies on the Immobilized-Lipase-Catalyzed Esterification of Alkyl Oleates in Solvent-Free Systems

2013 ◽  
Vol 645 ◽  
pp. 19-23 ◽  
Author(s):  
Hui Zhong ◽  
Zheng Fang ◽  
Bao Hua Zou ◽  
Xin Li ◽  
Kai Guo
Keyword(s):  
Oleic Acid ◽  
Low Temperature ◽  
High Selectivity ◽  
Immobilized Lipase ◽  
Enzyme Concentration ◽  
Molar Ratio ◽  
High Yield ◽  
Secondary Alcohols ◽  
Tertiary Alcohols ◽  
Candida Sp

The esterification of oleic acid with alkyl alcohols in solv ent-free systems was catalyzed by an immobilized lipase from Candida sp . 99-125. The influence of several factors, including enzyme concentration, temperature, molar ratio between oleic acid and alkyl alcohols, and structure of alcohol was also investigated. The results indicated that the reactions catalyzed by lipase at 20 o C, in the presence of 3% (w/w) lipase, on the molar ratio of 1:1 between oleic acid and alcohols, afforded products in high yield. It showed high selectivity to primary and low selectivity to secondary alcohols and tertiary alcohols because of the sterically hindered effect. Methanol has certain toxicity on the activity of the lipase. The lipase from Candida sp. 99-125 was identified to be an effective catalyst in the esterification of alcohol and oleic acid at low temperature.

Preparation of Ammonium Oleic Acid Salts and Their Evaluation as Shale Swelling Inhibitors in Water-Based Drilling Fluid

2021 ◽  
Vol 58 (4) ◽  
pp. 311-316
Author(s):  
Rongjun Zhang ◽  
Yun Bai ◽  
Yan Sun ◽  
Weichao Du ◽  
Chunsheng Pu ◽  
...  
Keyword(s):  
Oleic Acid ◽  
Drilling Fluid ◽  
Inhibitory Effect ◽  
Superior Performance ◽  
Molar Ratio ◽  
Inhibition Mechanism ◽  
Subsequent Work ◽  
Expansion Test ◽  
Water Based ◽  
Acid Salts

Abstract In this paper, ammonium oleic acid salts (AOS) were prepared from oleic acid and amines and investigated as low molecular weight shale swelling inhibitors. First, the inhibitory effect of AOS was investigated using the linear expansion test of bentonite. The results show that the inhibitor prepared from oleic acid and tetraethylene pentamine with a molar ratio of 1:2 (AOS-8) has an excellent inhibitory effect on the hydration expansion of bentonite. The inhibitory effect of AOS-8 on bentonite was further investigated in subsequent work steps using various methods, including the linear swelling test of clay and particle distribution measurement. The results show that AOS-8 has superior performance in inhibiting hydration swelling and dispersion of bentonite. With 0.5% AOS-8, the swelling rate was reduced to 37.7%, and the particle size of bentonite in water could be controlled with AOS-8. Finally, the inhibition mechanism of AOS-8 was determined in detail by scanning electron microscopy (SEM) and thermogravimetric analysis (TGA). In water-based drilling fluid, AOS-8 is compatible with conventional additives. It can also significantly improve the lubricating capacity of the mud cake after ageing at 120°C.

Low-temperature methane oxidation over oxide-supported Pd catalysts: inhibitory effect of water vapor

2002 ◽  
Vol 232 (1-2) ◽  
pp. 23-28 ◽  
Author(s):  
Ryuji Kikuchi ◽  
Shingo Maeda ◽  
Kazunari Sasaki ◽  
Stefan Wennerström ◽  
Koichi Eguchi
Keyword(s):  
Water Vapor ◽  
Low Temperature ◽  
Methane Oxidation ◽  
Inhibitory Effect ◽  
Pd Catalysts ◽  
Effect Of Water ◽  
Supported Pd Catalysts ◽  
Supported Pd

Al(OTf)3 — A highly efficient catalyst for the tetrahydropyranylation of alcohols under solvent-free conditions

2008 ◽  
Vol 86 (12) ◽  
pp. 1099-1104 ◽  
Author(s):  
Ahmed Kamal ◽  
M Naseer A Khan ◽  
Y VV Srikanth ◽  
K Srinivasa Reddy
Keyword(s):  
Comparative Study ◽  
Efficient Method ◽  
Catalytic Amount ◽  
Solvent Free ◽  
Molar Ratio ◽  
Reaction Conditions ◽  
Efficient Catalyst ◽  
Highly Efficient ◽  
Solvent Free Conditions ◽  
The Comparative Study

A simple and highly efficient method has been developed for the tetrahydropyranylation of alcohols by their reaction with 3,4-dihydro-2H-pyran (DHP) using a catalytic amount (0.01–1 mol%) of aluminium triflate under solvent-free conditions. The effect of various factors like temperature, amount of the catalyst, and molar ratio of substrates on the reaction conditions has also been studied. The comparative study of tetrahydropyranylation of benzyl alcohol using various catalysts including some reported ones shows the efficiency of this catalyst.Key words: tetrahydropyranylation, aluminium triflate, alcohols, catalysis.

Preparation and Characterization of a Novel Room Temperature Dicationic Ionic Liquid and its Application in the Synthesis of Xanthenediones Under Solvent-Free Conditions

2018 ◽  
Vol 21 (8) ◽  
pp. 602-608 ◽  
Author(s):  
Zainab Ehsani-Nasab ◽  
Ali Ezabadi
Keyword(s):  
Ionic Liquid ◽  
Room Temperature ◽  
Reaction Times ◽  
Significant Loss ◽  
Solvent Free ◽  
Acidity Function ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
Hammett Acidity Function ◽  
Dicationic Ionic Liquid

Aim and Objective: In the present work, 1, 1’-sulfinyldiethylammonium bis (hydrogen sulfate) as a novel room temperature dicationic ionic liquid was synthesized and used as a catalyst for xanthenediones synthesis. Material and Method: The dicationic ionic liquid has been synthesized using ethylamine and thionyl chloride as precursors. Then, by the reaction of [(EtNH2)2SO]Cl2 with H2SO4, [(EtNH2)2SO][HSO4]2 was prepared and after that, it was characterized by FT-IR, 1H NMR, 13C NMR as well as Hammett acidity function. This dicationic ionic liquid was used as a catalyst for the synthesis of xanthenediones via condensation of structurally diverse aldehydes and dimedone under solvent-free conditions. The progress of the reaction was monitored by thin layer chromatography (ethyl acetate/n-hexane = 3/7). Results: An efficient solvent-free method for the synthesis of xanthenediones has been developed in the presence of [(EtNH2)2SO][HSO4]2 as a powerful catalyst with high to excellent yields, and short reaction times. Additionally, recycling studies have demonstrated that the dicationic ionic liquid can be readily recovered and reused at least four times without significant loss of its catalytic activity. Conclusion: This new dicationic ionic liquid can act as a highly efficient catalyst for xanthenediones synthesis under solvent-free conditions.

Synthesis of Dihydropyrimidinones (DHPMs) and Hexahydro Xanthene Catalyzed by 1,4-Diazabicyclo [2.2.2] Octane Triflate Under Solvent-Free Condition

2019 ◽  
Vol 16 (5) ◽  
pp. 776-786 ◽  
Author(s):  
Deepa ◽  
Geeta D. Yadav ◽  
Mohd J. Aalam ◽  
Pooja Chaudhary ◽  
Surendra Singh
Keyword(s):  
Ethyl Acetoacetate ◽  
Biginelli Reaction ◽  
Solvent Free ◽  
Efficient Catalyst ◽  
Solvent Free Condition ◽  
Solvent Free Conditions ◽  
Xanthene Derivatives ◽  
Different Temperatures ◽  
Flash Column Chromatography ◽  
Biginelli Condensation

Objective:DABCO salts were evaluated as catalysts for the Biginelli reaction between 4- methoxybenzaldehyde, urea and ethyl acetoacetate under solvent-free conditions. 1,4-Diazabicyclo [2.2.2] octane triflate was found to be a simple, inexpensive, highly efficient catalyst for Biginelli reaction for a variety aromatic aldehyde with urea and ethyl acetoacetate at 80°C afforded corresponding 3,4-dihydropyrimidinones in 50-99% yields after 30-120 minutes. 1,3-Cyclohexadione was used in place of ethyl acetoacetate in the absence of urea this methodology is giving hexahydro xanthene derivatives in good to excellent yields after 3-4 hours.Methods:DABCO salt 4 (5 mol%), 4-methoxybenzaldehyde (0.73 mmol) and urea (0.73 mmol) were stirred for 10 minutes at 80°C, then ethyl acetoacetate (1.5 equiv.) was added and reaction mixture was stirred at 80°C for specified time. The resulting solution was stirred continuously and progress of the reaction was followed by TLC. The crude reaction mixture was purified by flash column chromatography on silica gel (hexane/ethyl acetate (1:2)) to give pure desired product.Results:Reaction conditions of the Biginelli reaction were optimized using 4-methoxybenzaldehyde (0.73 mmol), urea (0.73 mmol), and ethyl acetoacetate (5 equiv.) as model substrates catalyzed by 1,4-Diazabicyclo [2.2.2] octane triflate (5 mol%) in a different solvents, screening of different catalysts and different temperatures. Neat condition was found to be the best for the Biginelli condensation and corresponding 3,4- dihydropyrimidinones was obtained in good to excellent yields. When the reaction was carried out with benzaldehyde derivatives and cyclohexane-1,3-dione in place of ethyl acetoacetate in the absence of urea, solely corresponding hexahydro xanthene derivatives were obtained in 61-91% yields.Conclusion:In conclusion, we have applied salts of 1,4-Diaza-bicyclo [2.2.2] octane as catalysts in the Biginelli condensation and corresponding 3,4-dihydropyrimidinones were obtained in 50- 99% yields under solvent free conditions. This methodology is having advantages like simple work-up; low loading of catalyst and reaction was performed at moderate temperature under solvent-free conditions.

scholarly journals Synthesis and Characterization of Partially Renewable Oleic Acid-Based Ionomers for Proton Exchange Membranes

Polymers ◽  
2020 ◽  
Vol 13 (1) ◽  
pp. 130
Author(s):  
Carlos Corona-García ◽  
Alejandro Onchi ◽  
Arlette A. Santiago ◽  
Araceli Martínez ◽  
Daniella Esperanza Pacheco-Catalán ◽  
...  
Keyword(s):  
Oleic Acid ◽  
Proton Conductivity ◽  
Electrochemical Impedance ◽  
Proton Exchange Membranes ◽  
Proton Exchange ◽  
Molar Ratio ◽  
Aromatic Diamines ◽  
Chemical Structures ◽  
Long Chain

The future availability of synthetic polymers is compromised due to the continuous depletion of fossil reserves; thus, the quest for sustainable and eco-friendly specialty polymers is of the utmost importance to ensure our lifestyle. In this regard, this study reports on the use of oleic acid as a renewable source to develop new ionomers intended for proton exchange membranes. Firstly, the cross-metathesis of oleic acid was conducted to yield a renewable and unsaturated long-chain aliphatic dicarboxylic acid, which was further subjected to polycondensation reactions with two aromatic diamines, 4,4′-(hexafluoroisopropylidene)bis(p-phenyleneoxy)dianiline and 4,4′-diamino-2,2′-stilbenedisulfonic acid, as comonomers for the synthesis of a series of partially renewable aromatic-aliphatic polyamides with an increasing degree of sulfonation (DS). The polymer chemical structures were confirmed by Fourier transform infrared (FTIR) and nuclear magnetic resonance (1H, 13C, and 19F NMR) spectroscopy, which revealed that the DS was effectively tailored by adjusting the feed molar ratio of the diamines. Next, we performed a study involving the ion exchange capacity, the water uptake, and the proton conductivity in membranes prepared from these partially renewable long-chain polyamides, along with a thorough characterization of the thermomechanical and physical properties. The highest value of the proton conductivity determined by electrochemical impedance spectroscopy (EIS) was found to be 1.55 mS cm−1 at 30 °C after activation of the polymer membrane.

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