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Highly efficient epoxidation of vegetable oils catalyzed by a manganese complex with hydrogen peroxide and acetic acid
- Source :
- Green Chemistry, 21(9), 2436. Royal Society of Chemistry
- Publication Year :
- 2019
-
Abstract
- Epoxidized vegetable oils (EVOs) are versatile building blocks for lubricants, plasticizers, polyvinyl chloride (PVC) stabilizers, and surface coating formulations. In this paper, a catalytic protocol for the efficient epoxidation of vegetable oils is presented that is based on a combination of a manganese catalyst, H 2 O 2 as an oxidant, and acetic acid as an additive. This protocol relies on the use of a homogeneous catalyst based on the non-noble metal manganese in combination with a racemic mixture of the N,N′-bis(2-picolyl)-2,2′-bispyrrolidine ligand (rac-BPBP). The optimized reaction conditions entail only 0.03 mol% of the manganese catalyst with respect to the number of double bonds (ca. 0.1 wt% with respect to the oil) and ambient temperature. This epoxidation protocol is highly efficient, since it allows most of the investigated vegetable oils, including cheap waste cooking oil, to be fully epoxidized to EVOs in more than 90% yield with excellent epoxide selectivities (>90%) within 2 h of reaction time. In addition, the protocol takes place in a biphasic reaction medium constituted by the vegetable oil itself and an aqueous acetic acid phase, from which the epoxidized product can be easily separated via simple extraction. In terms of efficiency and reaction conditions, the current epoxidation protocol outperforms previously reported catalytic protocols for plant oil epoxidation, representing a promising alternative method for EVO production.
- Subjects :
- 010405 organic chemistry
Epoxide
chemistry.chemical_element
Homogeneous catalysis
Manganese
010402 general chemistry
01 natural sciences
Pollution
0104 chemical sciences
Catalysis
chemistry.chemical_compound
Surface coating
Acetic acid
Vegetable oil
chemistry
Environmental Chemistry
Organic chemistry
Hydrogen peroxide
Subjects
Details
- Language :
- English
- ISSN :
- 14639262
- Database :
- OpenAIRE
- Journal :
- Green Chemistry, 21(9), 2436. Royal Society of Chemistry
- Accession number :
- edsair.doi.dedup.....33319b0c4306563056600b5c6f6a9193