scholarly journals Optimization and kinetic study of methyl laurate synthesis using ionic liquid [Hnmp]HSO 4 as a catalyst

2018 ◽  
Vol 5 (9) ◽  
pp. 180672 ◽  
Author(s):  
Benyong Han ◽  
Wudi Zhang ◽  
Fang Yin ◽  
Shiqing Liu ◽  
Xingling Zhao ◽  
...  

Methyl laurate was synthesized from lauric acid (LA) and methanol via an esterification reaction using ionic liquids (ILs) as catalysts. The efficiencies of three different catalysts, 1-methylimidazole hydrogen sulfate ([Hmim]HSO 4 ), 1-methyl-2-pyrrolidonium hydrogen sulfate ([Hnmp]HSO 4 ) and H 2 SO 4 , were compared. The effect of the methanol/LA molar ratio, reaction temperature, reaction time and catalyst dosage on the esterification rate of LA was investigated by single-factor experiments. Based on the single-factor experiments, the esterification of LA and methanol was optimized using response surface methodology. The results showed that the most effective catalyst was the IL [Hnmp]HSO 4 . The optimal conditions were as follows: [Hnmp]HSO 4 dosage of 5.23%, methanol/LA molar ratio of 7.68 : 1, reaction time of 2.27 h and reaction temperature of 70°C. Under these conditions, the LA conversion of the esterification reached 98.58%. A kinetic study indicated that the esterification was a second-order reaction with an activation energy and a frequency factor of 68.45 kJ mol −1 and 1.9189 × 10 9 min −1 , respectively. The catalytic activity of [Hnmp]HSO 4 remained high after five cycles.

Author(s):  
Benyong Han ◽  
Fang Yin ◽  
Shiqing Liu ◽  
Xingling Zhao ◽  
Jing Liu ◽  
...  

Abstract Methyl laurate was synthesized from lauric acid and methanol using Brønsted acid ionic liquids as catalysts, by an esterification reaction. The efficiencies of four different catalysts, 1-methylimidazolium hydrogen sulfate ([Hmim]HSO4), 2-pyrrolidonium hydrogen sulfate ([Hnhp]HSO4), 1-(3-sulfonic acid) propyl-2-pyrrolidonium hydrogen sulfate ([C3SO3Hnhp]HSO4) and H2SO4 were compared. The effect of the methanol/lauric acid molar ratio, reaction temperature, reaction time, and catalyst dosage on the lauric acid conversion was investigated by single-factor experiments. On the basis of single-factor experiments, the esterification of lauric acid and methanol was optimized using response surface methodology (RSM) based on central composite design (CCD). The results showed that the most effective catalyst was the ionic liquid [C3SO3Hnhp]HSO4. The optimal conditions were as follows: [C3SO3Hnhp]HSO4 dosage of 10 % (based on the mass of lauric acid), methanol/lauric acid molar ratio of 9:1, reaction time of 1 h and reaction temperature of 70 °C. Under these conditions, the lauric acid conversion reached 95.33 %. The catalytic activity of [C3SO3Hnhp]HSO4 still remained high after 5 cycles.


2021 ◽  
Vol 29 (4) ◽  
Author(s):  
Ratna Dewi Kusumaningtyas ◽  
Haniif Prasetiawan ◽  
Radenrara Dewi Artanti Putri ◽  
Bayu Triwibowo ◽  
Siti Choirunisa Furi Kurnita ◽  
...  

Nyamplung seed (Calophyllum inophyllum L.) oil is a prospective non-edible vegetable oil as biodiesel feedstock. However, it cannot be directly used in the alkaline catalysed transesterification reaction since it contains high free fatty acid (FFA) of 19.17%. The FFA content above 2% will cause saponification reaction, reducing the biodiesel yield. In this work, FFA removal was performed using sulfuric acid catalysed esterification to meet the maximum FFA amount of 2%. Experimental work and response surface methodology (RSM) analysis were conducted. The reaction was conducted at the fixed molar ratio of nyamplung seed oil and methanol of 1:30 and the reaction times of 120 minutes. The catalyst concentration and the reaction temperature were varied. The highest reaction conversion was 78.18%, and the FFA concentration was decreased to 4.01% at the temperature of 60℃ and reaction time of 120 minutes. The polynomial model analysis on RSM demonstrated that the quadratic model was the most suitable FFA conversion optimisation. The RSM analysis exhibited the optimum FFA conversion of 78.27% and the FFA content of 4%, attained at the reaction temperature, catalyst concentration, and reaction time of 59.09℃, 1.98% g/g nyamplung seed oil, and 119.95 minutes, respectively. Extrapolation using RSM predicted that the targeted FFA content of 2% could be obtained at the temperature, catalyst concentration, and reaction time of 58.97℃, 3%, and 194.9 minutes, respectively, with a fixed molar ratio of oil to methanol of 1:30. The results disclosed that RSM is an appropriate statistical method for optimising the process variable in the esterification reaction to obtain the targeted value of FFA.


2019 ◽  
Vol 13 (4) ◽  
pp. 464-474 ◽  
Author(s):  
Youzhou Jiao ◽  
Yahe Mei ◽  
Le Wang ◽  
Jiaao Liu ◽  
Zhiping Zhang ◽  
...  

The innocuous utilization of diseased swine carcasses is a key issue in reducing environmental pollution and ensuring safety in animal husbandry. In this study, by using fat from diseased swine carcasses as raw materials, response surface experiments were conducted to investigate the influences of reaction time, catalyst concentration, reaction temperature, and methanol/oil molar ratio on the biodiesel purity and the optimum conditions for biodiesel production were determined. Furthermore, three-dimensional (3D) ultrasound assistance was adopted and kinetic analysis was performed. The results show that the influencing factors on biodiesel purity, in descending order, were determined to be reaction temperature > catalyst concentration > reaction time > methanol/oil molar ratio. Moreover, the maximum biodiesel purity was 93.7% under the following optimal conditions: catalyst concentration of 5.0 wt%; reaction temperature of 68 °C; methanol/oil molar ratio of 10:1; reaction time of 37 h. When 3D ultrasound assistance was adopted, the maximum biodiesel purity of 98.1% was obtained for the reaction process of 8 h under the ultrasound power and frequency of 500 W and 20 kHz, respectively. And the esterification reaction time was significantly reduced, compared to without ultrasound assistance. The results of kinetic analysis demonstrate that the reaction rate constants of the ultrasound group were 4.45–5.52 times greater than that of the control group. And the activation energy for the ultrasound group was 25.58 kJ/mol, which is 22.81% lower than that of the control group. This study will help to conduct large-batch biodiesel production from diseased swine carcasses in the future.


RSC Advances ◽  
2015 ◽  
Vol 5 (64) ◽  
pp. 52072-52078 ◽  
Author(s):  
Tianwei Jin ◽  
Bin Wang ◽  
Jinhui Zeng ◽  
Chun Yang ◽  
Yuqi Wang ◽  
...  

The interaction of raw material ratio, reaction temperature and reaction time on the esterification reaction of free fatty acids, and a kinetic analysis of it.


2014 ◽  
Vol 521 ◽  
pp. 72-75
Author(s):  
Xiao Feng Liu

An esterification reaction of monomer acid with methanol using p-toluenesulfonic acid as catalyst for the preparation of biodiesel was studied. The process variables that influence the esterification of monomer acid, such as catalyst concentration, molar ratio of methanol to acid, reaction time and reaction temperature, were investigated and optimized. Through the single factor experiment, the optimum conditions obtained for the esterification were molar ratio of methanol to acid 3:1, usage amount of p-toluenesulfonic acid 6% and reaction time 3h, reaction temperature 70°C.The produced biodiesel was found to exhibit fuel properties within the limits prescribed by the latest American Standards for Testing Material (ASTM) and 0#diesel oil.


2015 ◽  
Vol 727-728 ◽  
pp. 119-122
Author(s):  
Shi Tang ◽  
Lei Zhang

One system of Shrinkage reducing monomer was prepared by esterification reaction, the test method of esterification rate was discussed, to find out the significant factors of the esterification rate by using the orthogonal design. The influence of ether-to-acid mole ratio, reaction temperature, catalyst dosage and reaction time on the esterification was also investigated. The results demonstrate that the suitable esterifying conditions mainly require the suitable proportion of MA to C5H12O3 as 1~1.05 to 1, and under the temperature of 120~125°C, and 3~3.5hours of reaction time.


2011 ◽  
Vol 396-398 ◽  
pp. 2411-2415 ◽  
Author(s):  
Ping Lan ◽  
Li Hong Lan ◽  
Tao Xie ◽  
An Ping Liao

Isoamyl acetate was synthesized from isoamylol and glacial acetic acid with strong acidic cation exchanger as catalyst. The effects of reaction conditions such as acid-alcohol ratio, reaction time, catalyst dosage to esterification reaction have been investigated and the optimum reaction conditions can be concluded as: the molar ratio of acetic acid to isoamylol 0.8:1, reaction time 2h, 25 % of catalyst (quality of acetic acid as benchmark). The conversion rate can reach up to 75.46%. The catalytic ability didn’t reduce significantly after reusing 10 times and the results showed that the catalyst exhibited preferably catalytic activity and reusability.


2014 ◽  
Vol 900 ◽  
pp. 361-364
Author(s):  
Xiao Hui Wang ◽  
Xi Hua Du ◽  
Li Min Dong

Esters of Citric acid and palmityl alcohol were synthesized by esterification reaction under catalysis of cation exchange resin and P-toluene sulfonic acid respectively. The effects of amount of catalyst, ratio of raw materials, reaction time and temperature on the synthesis reaction were investigated . The experimental results showed that optimum of process conditions were 1:1~1:1.5 molar ratio of citric acid and palmityl alcohol, reaction temperature of 130~140°C, reaction time of 2 h. Conversion of palmityl alcohol were all more than 90% under 0.3% dosage using p-toluene sulfonic acid as the catalyst, or 0.5% dosage using 721 cation exchange resin with sulfonic acid type as catalyst. The synthesized product had good surface activity.


2019 ◽  
Vol 19 (4) ◽  
pp. 849
Author(s):  
Nurul Atikah Amin Yusof ◽  
Nursyamsyila Mat Hadzir ◽  
Siti Efliza Ashari ◽  
Nor Suhaila Mohamad Hanapi ◽  
Rossuriati Dol Hamid

Optimization of the lipase catalyzed enzymatic synthesis of betulinic acid amide in the presence of immobilized lipase, Novozym 435 from Candida antartica as a biocatalyst was studied. Response surface methodology (RSM) and 5-level-4-factor central-composite rotatable design (CCRD) were employed to evaluate the effects of the synthesis parameters, such as reaction time (20–36 h), reaction temperature (37–45 °C), substrate molar ratio of betulinic acid to butylamine (1:1–1:3), and enzyme amounts (80–120 mg) on the percentage yield of betulinic acid amide by direct amidation reaction. The optimum conditions for synthesis were: reaction time of 28 h 33 min, reaction temperature of 42.92 °C, substrate molar ratio of 1:2.21, and enzyme amount of 97.77 mg. The percentage yield of actual experimental values obtained 65.09% which compared well with the maximum predicted value of 67.23%. The obtained amide was characterized by GC, GCMS and 13C NMR. Betulinic acid amide (BAA) showed a better cytotoxicity compared to betulinic acid as the concentration inhibited 50% of the cell growth (IC50) against MDA-MB-231 cell line (IC50 < 30 µg/mL).


Holzforschung ◽  
2007 ◽  
Vol 61 (5) ◽  
pp. 499-503 ◽  
Author(s):  
Shifa Wang

Abstract A light-colored rosin glycerol ester was synthesized from gum rosin and glycerol in the presence of a highly effective decolorizing agent. The effects of the type and dosage of the decolorizing agent and the reaction temperature and time on the yield, softening point, color, and acid number of the rosin glycerol ester were investigated. Experimental results showed that 4,4′-thio-bis(6-tert-butyl-3-methyl phenol) was the best decolorizing agent. It promoted esterification at an optimal dosage of 0.5% (based on the weight percentage of starting material rosin). Suitable conditions for esterification of rosin and glycerol were: reaction temperature, 260–270°C; reaction time, 6–8 h; and rosin/glycerol molar ratio, 2.5:1 (mol mol-1). The characteristics of the rosin glycerol ester obtained under these conditions were as follows: softening point, 90–94°C (ball and ring method); color, 1–2 (Gardner value); acid number, 7–8; and yield, >88% (based on the total weight of rosin and glycerol). The selected additive has a multifunctional effect involving bleaching, disproportionation, and catalysis.


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