Esterification of trimethylolpropane with fatty acids

Itsikson, T. M.; Milovidova, N. V.; Rapport, I. B.

doi:10.1007/bf00730142

Cited by 4 publications

(6 citation statements)

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“…Experiments were conducted with a 3.7:1 molar ratio of oleic acid to TMP, 4%w/w catalyst for 3 h. The GC chromatogram of trimethylolpropane esters is shown in Fig. 1 As compared with the reaction temperature in previous reports concerning the conventional homogenous and heterogeneous catalysts for esterification [9,18], the catalyst gave a satisfactory yield of the TE at a much lower temperature. Initially, both the conversion of TMP and selectivity of TE (w%) increased with the reaction temperature and reached 99.0 and 92.8%, respectively, at 100°C, then the yield dropped with further increases of the reaction temperature.…”

Section: Resultsmentioning

confidence: 93%

Synthesis of Trimethylolpropane Esters of Oleic Acid Using a Multi‐SO₃H‐Functionalized Ionic Liquid as an Efficient Catalyst

Chen

Yan

2011

J Americ Oil Chem Soc

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Biodegradable trimethylolpropane triesters of oleic acid were synthesized by esterification of trimethylolpropane and oleic acid over a multi-SO 3 H-functionalized strong Brønsted acidic ionic liquid as the catalyst. The results showed that the esterification can proceed satisfactorily over the catalyst at an ambient pressure even without simultaneous removal of water. Under the optimal reaction conditions (temperature: 100°C, reaction time: 3 h, reactant molar ratio: 3.6:1, and catalyst amount, high conversion rate of trimethylolpropane (99.0%) and selectivity of trimethylolpropane triester (92.1%) were obtained. The ionic liquid was reused six times after the removal of water and no obvious change in catalytic activity was detected. Operational simplicity, high yields along with good reusability makes the multi-SO 3 H-functionalized ionic liquid a promising catalyst for the esterification of trimethylolpropane with oleic acid.

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Section: Resultsmentioning

confidence: 93%

Synthesis of Trimethylolpropane Esters of Oleic Acid Using a Multi‐SO₃H‐Functionalized Ionic Liquid as an Efficient Catalyst

Chen

Yan

2011

J Americ Oil Chem Soc

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“…85% of the esters produced by using 7% sodium bisulphate catalyst at a temperature of 110-120 °C for 2 hours. The use of 1% sulfuric acid catalyst in the same reaction resulted in 78% ester at a temperature of 110-120 °C for 60 hours 11 . There are also the studies of TMP ester production carried out by transesterification reaction of palm oil methyl ester (POME) with trimetilolpropana (TMP) or palm kernel oil methyl esters (PKOME) with the yield of 98% triester (TE) 12 .…”

Section: Introductionmentioning

confidence: 99%

The Effects of Various Acid Catalyst on the Esterification of Jatropha Curcas Oil based Trimethylolpropane Ester as Biolubricant Base Stock

Arbain

Salimon

2011

Journal of Chemistry

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Biolubricant production of trimethylolpropane ester (ET) was conducted via esterification of fatty acid (FA) ofJatropha curcasoil with trimethylolpropane (TMP). The condition for this reaction was as follows: temperature was 150°C, time of reaction was 3 hours, molar ratio of FA: TMP was 4:1 and 2% wt/wt concentrated catalyst (based on weight of FA). Different catalyst was used in this reaction such as perchloric acid, sulfuric acid,p-toluenesulfonic acid, hydrochloric acid and nitric acid. The composition of ET was determined by Gas Chromatography (GC-FID). The ester group was confirmed by Fourier Transform Infrared Spectroscopy (FTIR) and the structure was confirmed by proton and carbon Nuclear Magnetic Resonance (1H-NMR and13C-NMR) spectra. 70% of ET was successfully synthesized using perchloric acid in this research. The pour point of the product was observed as low as –23°C, flash point is >300°C and viscosity index is 150.

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“…Itsikson et al . achieved a yield of esters of above 90% in 6 h at 160°C using isovaleric acid as a FA and sulfuric acid as a catalyst 25 . Arbain et al .…”

Section: Introductionmentioning

confidence: 99%

“…Itsikson et al achieved a yield of esters of above 90% in 6 h at 160°C using isovaleric acid as a FA and sulfuric acid as a catalyst. 25 Arbain et al compared five different homogeneous catalysts, namely perchloric, sulfuric, p-toluensulfonic, hydrochloric and nitric acids, for the synthesis of TMP esters from a mixture of long-chain FAs. Among them, perchloric and sulfuric acids gave the highest yields (>70%) after a reaction time of 3 h at 150°C.…”

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confidence: 99%

An environmentally friendly production ofester‐biolubricantfrom oleic acid

Ramos

Haro

Rodríguez

et al. 2022

Biofuels Bioprod Bioref

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The production of oleic‐based trimethylolpropane (TMP) esters via the esterification reaction between oleic acid (OA) and TMP in a reactive distillation system, employing the environmentally friendly catalyst methanesulfonic acid, was explored. The homogeneous acid catalyst, the OA/TMP molar ratio within 1.0–3.0, the esterification reaction enhancement and a new purification technique, using choline hydroxide (ChOH), for obtaining choline carboxylate as a subproduct, were studied. It was found that using an OA/TMP molar ratio of 3.0, only unreacted OA remained as an impurity. The deleterious or beneficial effect of intermediate products, unreacted OA and temperature on the kinematic viscosity were unraveled. The kinematic viscosity behavior for the products was practically independent of temperature but an abrupt enlargement of the kinematic viscosity was observed in the presence of functional groups in the intermediate esters, even greater than the Mark–Houwink counterpart effect. On contrary, the presence of OA in the final product decreased the kinematic viscosity attending to its lower molecular weight with respect to the trimethylolpropane trioleate one. It was found that trimethylolpropane monooleate is undesirable for the viscosity index, whereas the presence of trimethylolpropane dioleate could also increase the viscosity index to a small extent, requiring a complex purification process. Finally, it is possible to affirm that the optimal TMP‐based lubricant obtained using an OA/TMP molar ratio of 3.0, after OA neutralization presented good marginal benefit and a viscosity index of 208.7, which is applicable for gear lubricants. © 2022 The Authors. Biofuels, Bioproducts and Biorefining published by Society of Industrial Chemistry and John Wiley & Sons Ltd.

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Esterification of trimethylolpropane with fatty acids

Cited by 4 publications

References 1 publication

Synthesis of Trimethylolpropane Esters of Oleic Acid Using a Multi‐SO₃H‐Functionalized Ionic Liquid as an Efficient Catalyst

Synthesis of Trimethylolpropane Esters of Oleic Acid Using a Multi‐SO₃H‐Functionalized Ionic Liquid as an Efficient Catalyst

The Effects of Various Acid Catalyst on the Esterification of Jatropha Curcas Oil based Trimethylolpropane Ester as Biolubricant Base Stock

An environmentally friendly production ofester‐biolubricantfrom oleic acid

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Esterification of trimethylolpropane with fatty acids

Cited by 4 publications

References 1 publication

Synthesis of Trimethylolpropane Esters of Oleic Acid Using a Multi‐SO3H‐Functionalized Ionic Liquid as an Efficient Catalyst

Synthesis of Trimethylolpropane Esters of Oleic Acid Using a Multi‐SO3H‐Functionalized Ionic Liquid as an Efficient Catalyst

The Effects of Various Acid Catalyst on the Esterification of Jatropha Curcas Oil based Trimethylolpropane Ester as Biolubricant Base Stock

An environmentally friendly production ofester‐biolubricantfrom oleic acid

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Synthesis of Trimethylolpropane Esters of Oleic Acid Using a Multi‐SO₃H‐Functionalized Ionic Liquid as an Efficient Catalyst

Synthesis of Trimethylolpropane Esters of Oleic Acid Using a Multi‐SO₃H‐Functionalized Ionic Liquid as an Efficient Catalyst