Degradation of catalytic epoxidation of oleic acid palm oil by in situ performic acid

Jalil, Mohd Jumain; Zaini, Mohd Saufi Md; Yamin, Aliff Farhan Mohd; Morad, Norhashimah; Hâdi, Abdul

doi:10.1088/1742-6596/1349/1/012001

Cited by 7 publications

(11 citation statements)

References 9 publications

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“…Higher H 2 O 2 causes the stability of the oxirane ring to reduce and leads to an accelerated rate of oxirane ring decomposition or degradation [18], which is in agreement with the report for the stability of epoxide sunflower and soybean oil degraded at 30 wt.% H 2 O 2 [30]. Others reported that the cleavage of oxirane rings of epoxide oleic acid-based palm oil was affected the most by hydrogen peroxide, followed by formic acid, which leads to the formation of diol and a-glycol as side products [31].…”

Section: The Effect Of Hydrogen Peroxide Molar Ratiosupporting

confidence: 89%

“…Increasing the HCOOH concentration had a detrimental effect on the epoxide ring due to the epoxide ring being unstable in an acidic medium and hence easier to be degraded [30]. Therefore, the epoxide ring's hydrolysis was promoted and reduced the final OOC value [31], which agrees with the report that stated that the epoxide ring degraded faster at the molar ratio of epoxidized oleic acid-based palm oil to HCOOH of 1:1 [31].…”

Section: The Effect Of the Formic Acid Molar Ratiosupporting

confidence: 88%

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Optimization of High Yield Epoxidation of Malaysian Castor Bean Ricinoleic Acid with Performic Acid

Salih

Salimon

2022

Indones. J. Chem.

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Epoxidized castor oil (ECO) has shown high potential for industrial applications as value-added products such as polymer coating, plasticizer, and biolubricant. Epoxidized ricinoleic acid recovered from ECO has potential for industrial usage. In this work, epoxidized ricinoleic acid (ERA) was synthesized through in situ generated performic acid epoxidation of ricinoleic acid (RA). The epoxidation process was optimized by several reaction parameters, such as the molar ratio of formic acid to ethylenic unsaturation, the molar ratio of hydrogen peroxide to ethylenic unsaturation, and reaction temperature. The response reaction parameters of oxirane oxygen content (OOC) and iodine value (IV) were then evaluated. The results showed the optimal condition for the epoxidation of RA was obtained at 50 °C, the molar ratio of formic acid and hydrogen peroxide to ethylenic unsaturation of 1:8:1 for 4 h reaction time. A high yield of ERA of 86% with relative conversion into oxirane of 85.3% was achieved at the optimum condition. The optimum ERA showed a high OOC value of 4.00% and a low IV value of 2.24 mg/g. It is plausible that ERA can be used as an intermediate starting material to prepare value-added products such as biosurfactants, biopolymer additives, or biolubricants.

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Section: The Effect Of Hydrogen Peroxide Molar Ratiosupporting

confidence: 89%

Section: The Effect Of the Formic Acid Molar Ratiosupporting

confidence: 88%

Optimization of High Yield Epoxidation of Malaysian Castor Bean Ricinoleic Acid with Performic Acid

Salih

Salimon

2022

Indones. J. Chem.

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“…Then, the mixture was heated at the optimum temperature of 55˚C. This experiment was heated and stir simultaneously at a constant 400 rpm [9]. The sample is taken every 5 minutes after reached the optimum temperature and every 1 hour for DHSA production.…”

Section: Methodsmentioning

confidence: 99%

Formation of Dihydroxystearic Acid (DHSA) from Epoxidized Palm Oleic Acid by Peracid Mechanism and Their Kinetic Study

Jalil¹,

Habr²,

Hadi³

et al. 2020

JMechE

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Dihydroxystearic acid (DHSA) is a product derived from a chemical modification of palm oleic acid. Application of these valuable fatty acids can be found in cosmetics, as a thickening agent and as a coating agent for pigments due to its unique structure. This study investigates the effect of a catalyst on epoxidation and the formation of DHSA by peracid mechanism. The epoxidation yield calculated by relative conversion to oxirane (RCO%) with a high yield of 95% achieved. Thereafter, the epoxidized oleic acid was hydrolyzed to produce DHSA. The formation of DHSA was verified by analysed the physicochemical properties using Fourier Transform Infra-red (FTIR). The kinetic model was being conducted to determine reaction rate using Particle Swarm (PS). The result showed that PS obtained a minimum error of 0.2005 and a correlation coefficient, r of 0.9999.

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“…The kinetic model of the epoxidation process and epoxide ring degradation can be developed based on the following rate constants: k 11 , k 12 , k 2 , and k 3 . The following rate equations were modeled, and the set of simultaneous differential equations is given as Equations (7)(8)(9)(10)(11)(12)(13). Figure 1 shows the flow chart of the procedure used to determine the rate constants.…”

Section: Kinetic Modeling Of the In Situ Hydrolysis Of Eoa For Dhsa Productionmentioning

confidence: 99%

“…The epoxidized oil is in cis configuration and therefore, its ring-opening products are in trans configuration. 10 One of these possible chemical modifications is the conversion of the oxirane rings, followed by hydrolysis, producing dihydroxystearic acid (DHSA).…”

Section: Introductionmentioning

confidence: 99%

Highly production of dihydroxystrearic acid from catalytic epoxidation process by in situ peracid mechanism

Jalil

Azmi

Hâdi

2021

Env Prog and Sustain Energy

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Epoxidized vegetable oils are great concern as they are obtained from sustainable, and renewable natural resources. The epoxidation of palm oil-derived oleic acid was carried out by using in situ generated performic acid to produce epoxidized palm oil-derived oleic acid. The maximum conversion of palm oil-derived oleic acid into oxirane was 86% by applying the in situ peracid mechanism. Based on the Fourier-transform infrared spectrum, the hydroxyl group was observed within a wavenumber range of 1210-1320 cm À1 . Last, a mathematical model was developed using Runge-Kutta method and after 100 iterations, the reaction rate parameters were obtained as follows: k 11 = 0.046 molÁL À1 Ámin À1 , k 12 = 39.058 molÁL À1 Ámin À1 , k 2 = 2.789 molÁL À1 Ámin À1 , and k 3 = 0.0235 molÁL À1 Ámin À1 for of dihydroxystearic acid production.

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Degradation of catalytic epoxidation of oleic acid palm oil by in situ performic acid

Cited by 7 publications

References 9 publications

Optimization of High Yield Epoxidation of Malaysian Castor Bean Ricinoleic Acid with Performic Acid

Optimization of High Yield Epoxidation of Malaysian Castor Bean Ricinoleic Acid with Performic Acid

Formation of Dihydroxystearic Acid (DHSA) from Epoxidized Palm Oleic Acid by Peracid Mechanism and Their Kinetic Study

Highly production of dihydroxystrearic acid from catalytic epoxidation process by in situ peracid mechanism

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