Synthesis of Dimerate Esters by Solvent-Free Method

Armylisas, Abu Hassan Noor

doi:10.21894/jopr.2017.2901.12

Cited by 4 publications

(3 citation statements)

References 7 publications

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“…Unfortunately, chemically synthesized esters cannot be recognized as natural 11,12 . Chemical synthesis needs strong acids such as sulfuric/sulfonic acid, hydrochloric acid, phosphoric acid, or p ‑toluenesulfonic as catalyst 13 . During reaction, a hydrogen atom from the catalytic acid is involved in the protonation of the carbonyl oxygen, followed by attacking with alcohol, and finally ended up by releasing a molecule of water and the targeting ester 13 .…”

Section: Introductionmentioning

confidence: 99%

“…Chemical synthesis needs strong acids such as sulfuric/sulfonic acid, hydrochloric acid, phosphoric acid, or p ‑toluenesulfonic as catalyst 13 . During reaction, a hydrogen atom from the catalytic acid is involved in the protonation of the carbonyl oxygen, followed by attacking with alcohol, and finally ended up by releasing a molecule of water and the targeting ester 13 . The temperature should be 50 to 60ºC, and on the meanwhile lots of by‐products are produced and additional stages are required for the separation and purification 13,14 .…”

Section: Introductionmentioning

confidence: 99%

“…During reaction, a hydrogen atom from the catalytic acid is involved in the protonation of the carbonyl oxygen, followed by attacking with alcohol, and finally ended up by releasing a molecule of water and the targeting ester 13 . The temperature should be 50 to 60ºC, and on the meanwhile lots of by‐products are produced and additional stages are required for the separation and purification 13,14 . These processes are unhealthy and considered as environmentally unsafe 6,15,16 …”

Section: Introductionmentioning

confidence: 99%

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The occurrence, enzymatic production, and application of ethyl butanoate, an important flavor constituent

Minhazul

2020

Flavour & Fragrance J

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Fermented food is loved by people all over the world because of the unique flavor. Esters of short-chain fatty acids are renowned for their contribution to the flavor of different fermented foods. In these foods, esters are produced in a diverse proportion because of microbial activities. 1,2 It is often needed to add esters as flavor additives to maintain and enhance the flavor or add a special flavor tone. 3 The growing demand for specific flavor has been a major scientific research area to produce esters on a large scale and in a safe and cost-proficient way. Natural sources such as fruits are the primary origin of esters. Esters can be extracted from these natural sources using various techniques such as fractional distillation, compound extraction using supercritical fluids, continuous liquid-liquid extraction, pervaporation, and adsorption. 4,5 Plants contain esters in a very low amount and also depend on the plant growth and climatic conditions. 6 Therefore, direct extraction of esters from natural sources is costly, time-consuming, and lower in yield, and the quality is not up to the mark. 7-9 But the extracted esters are marked as natural and can be used for food production. 10

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The occurrence, enzymatic production, and application of ethyl butanoate, an important flavor constituent

Minhazul

2020

Flavour & Fragrance J

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Synthesis of Dimer Acid 2‐Ethylhexyl Esters and their Physicochemical Properties as Biolubricant Base Stock and their Potential as Additive in Commercial Base Oils

Isah

Zhang

Biresaw

et al. 2021

J Americ Oil Chem Soc

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Previously synthesized C36‐dimer acids (DA) have been esterified (97 ± 0.2% conversion at 120 °C for 72 hours) with 2‐ethylhexanol (2‐EH) to produce a new class of C52‐DA 2‐EH esters that have potential application in biolubricant formulations such as base oils and additives. Investigation of physicochemical and lubricant properties showed the bio‐based esters have good solubility in commercial base stocks such as polyalpha olefin (PAO‐6) (>20 w/w) and high‐oleic sunflower oil (HOSuO) (>20 w/w). The neat C52‐DA 2‐EH esters displayed a three‐ to eightfold higher kinematic viscosity and comparable viscosity index (VI = 134) as a commercial base stock, PAO‐6 (VI =137). Both C52‐DA 2‐EH esters, whose parent C36‐DA were synthesized with two different zeolite catalysts, were oxidatively stable above 176 °C. Blending C52‐DA 2‐EH esters in HOSuO improved the pour point (PP) of HOSuO from −18.8 to −21.0 °C at 1% w/w and the cloud point (CP) from −6.3 to −10.6 °C at 8% w/w of C52‐DA 2‐EH ester 1. A similar trend was observed for C52‐DA 2‐EH ester 2, indicating that the esters possess PP depressant (PPD) characteristics in HOSuO blends. Blending C52‐DA 2‐EH esters in PAO‐6 increased the VI of PAO‐6, which is an indication that the bio‐based esters were acting as VI improvers (VII). It was concluded that C52‐DA 2‐EH esters can be employed commercially as bio‐based base oils and as PPD and VII additives in lubricant formulations.

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Excellent Properties of Dimer Fatty Acid Esters as Biolubricant Produced by Catalyst‐ and Solvent‐Free Esterification

Armylisas

Fauzi

Mohd

et al. 2019

Euro J Lipid Sci & Tech

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Currently most technologies available to produce esters require acid or base catalysts for esterification or transesterification reactions. Production of dimerate esters (DE) exhibiting potential as a biolubricant for low temperature applications using catalyst‐ and solvent‐free approaches is presented in this article. Hydrogenated C36 dimer acid and alcohol are reacted under the following conditions: dimer acid/alcohol (1:4.5 molar ratio), 150–200 °C, 24 h, 3Å molecular sieve (15% w/w). The performances of four DE species—dibutyl, dihexyl, di‐(2‐ethylhexyl), and dioctyl dimerate—as lubricant base stocks are evaluated by kinematic viscosity, viscosity index, cloud and pour point (cold flow properties) as well as oxidative stability, and compared with commercial synthetic lubricant base stock and DE, Radialube 7121. High viscosity indexes ranging between 129 and 138 are observed for the synthesized DEs, which are comparable with two commercial base stock, polyalpha olefin (PAO), and polyolester (POE). Significantly low pour point, less than −42 °C, is observed for di‐(2‐ethylhexyl) dimerate attributed to the branching of the side chain. The DEs are categorized as ISO VG 68 based on their viscosity according to ISO 3448 classification and show potential as biolubricant with high viscosity index and excellent cold flow properties. Practical Applications: DFAE obtained have high potential to be used as lubricant base stock for equipment and machinery operating at extremely low temperature.

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Synthesis of Dimerate Esters by Solvent-Free Method

Cited by 4 publications

References 7 publications

The occurrence, enzymatic production, and application of ethyl butanoate, an important flavor constituent

The occurrence, enzymatic production, and application of ethyl butanoate, an important flavor constituent

Synthesis of Dimer Acid 2‐Ethylhexyl Esters and their Physicochemical Properties as Biolubricant Base Stock and their Potential as Additive in Commercial Base Oils

Excellent Properties of Dimer Fatty Acid Esters as Biolubricant Produced by Catalyst‐ and Solvent‐Free Esterification

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