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Chemoenzymatic epoxidation of alkenes and reusability study of the phenylacetic acid.

Abdulmalek E, Arumugam M, Mizan HN, Abdul Rahman MB, Basri M, Salleh AB - ScientificWorldJournal (2014)

Bottom Line: A variety of alkenes were oxidised with this system, resulting in 75-99% yield of the respective epoxides.On the other hand, the phenylacetic acid was recovered from the reaction media and reused for more epoxidation.Interestingly, the waste phenylacetic acid had the ability to be reused for epoxidation of the 1-nonene to 1-nonene oxide, giving an excellent yield of 90%.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia.

ABSTRACT
Here, we focused on a simple enzymatic epoxidation of alkenes using lipase and phenylacetic acid. The immobilised Candida antarctica lipase B, Novozym 435 was used to catalyse the formation of peroxy acid instantly from hydrogen peroxide (H2O2) and phenylacetic acid. The peroxy phenylacetic acid generated was then utilised directly for in situ oxidation of alkenes. A variety of alkenes were oxidised with this system, resulting in 75-99% yield of the respective epoxides. On the other hand, the phenylacetic acid was recovered from the reaction media and reused for more epoxidation. Interestingly, the waste phenylacetic acid had the ability to be reused for epoxidation of the 1-nonene to 1-nonene oxide, giving an excellent yield of 90%.

Show MeSH
Mechanism of Prilezhaev epoxidation of alkene.
© Copyright Policy - open-access
Related In: Results  -  Collection


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sch2: Mechanism of Prilezhaev epoxidation of alkene.

Mentions: The in situ produced peroxy acid then oxidises the alkene, affording the respective epoxide and regenerating the carboxylic acid. The reaction mechanism for Prilezhaev epoxidation of alkenes is shown in Scheme 2.


Chemoenzymatic epoxidation of alkenes and reusability study of the phenylacetic acid.

Abdulmalek E, Arumugam M, Mizan HN, Abdul Rahman MB, Basri M, Salleh AB - ScientificWorldJournal (2014)

Mechanism of Prilezhaev epoxidation of alkene.
© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC3921943&req=5

sch2: Mechanism of Prilezhaev epoxidation of alkene.
Mentions: The in situ produced peroxy acid then oxidises the alkene, affording the respective epoxide and regenerating the carboxylic acid. The reaction mechanism for Prilezhaev epoxidation of alkenes is shown in Scheme 2.

Bottom Line: A variety of alkenes were oxidised with this system, resulting in 75-99% yield of the respective epoxides.On the other hand, the phenylacetic acid was recovered from the reaction media and reused for more epoxidation.Interestingly, the waste phenylacetic acid had the ability to be reused for epoxidation of the 1-nonene to 1-nonene oxide, giving an excellent yield of 90%.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia.

ABSTRACT
Here, we focused on a simple enzymatic epoxidation of alkenes using lipase and phenylacetic acid. The immobilised Candida antarctica lipase B, Novozym 435 was used to catalyse the formation of peroxy acid instantly from hydrogen peroxide (H2O2) and phenylacetic acid. The peroxy phenylacetic acid generated was then utilised directly for in situ oxidation of alkenes. A variety of alkenes were oxidised with this system, resulting in 75-99% yield of the respective epoxides. On the other hand, the phenylacetic acid was recovered from the reaction media and reused for more epoxidation. Interestingly, the waste phenylacetic acid had the ability to be reused for epoxidation of the 1-nonene to 1-nonene oxide, giving an excellent yield of 90%.

Show MeSH