Epoxidation of n-hexene and cyclohexene over titanium-containing catalysts

Bu, Jie; Yun, Samhun; Rhee, Hyun‐Ku

doi:10.1007/bf02789257

Cited by 12 publications

(9 citation statements)

References 18 publications

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“…Standard industrial process for epoxidation of vegetable oil is based on in situ epoxidation, in which peracid is generated by reacting acetic or formic acid with hydrogen peroxide in the presence of strong mineral acids such as H 2 SO 4 and H 3 PO 4 (83). Epoxidation is carried out either homogeneous (84)(85)(86) or by using a heterogeneous catalyst (87). In homogeneous catalysis, peracids such as peracetic acid generated in situ by mixing hydrogen peroxide with acetic acid are used to epoxidize vegetable oils.…”

Section: Epoxidationmentioning

confidence: 99%

Lubricants from renewable energy sources – a review

Soni

Agarwal

2014

Green Chemistry Letters and Reviews

114

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Lubricant oils are known to decrease the friction coefficient between two contacting surfaces. It is essential for the correct function of almost the totality of mechanical machinery working in the entire world. Lubricant oils consist of about 80% of oily base stocks which attributes to their properties of viscosity, stability, and pour point to the lubricant plus additives supplemented to improve these properties. Petroleum lubricants are usually environmentally unacceptable due to their low biodegradability and toxicity. These oils contaminate the air, soil, and drinking water and affect human and plant life to a great extent. Thus, the demand for environmentally acceptable lubricants is increasing along with the public concerns for a pollution-free environment. Plant oils are promising as base fluid for biolubricants because of their excellent lubricity, biodegradability, viscosity-temperature characteristics, and low volatility. The purpose of this paper is to present a survey of the current status of biolubricating oil. This research provides an overview on the synthesis, tribochemical behavior; the effect of structure on friction/wear, load-bearing capacity, resistance to rise in specimen temperature, and varying response of antiwear/extreme-pressure additives in the presence of vegetable oil/derivative structures has also been discussed. Though a significant number of papers have been published in this area, there is still much to explore. A proper selection of base oil and additives is therefore essential for an efficient synthesis of biolubricating oil.

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Section: Epoxidationmentioning

confidence: 99%

Lubricants from renewable energy sources – a review

Soni

Agarwal

2014

Green Chemistry Letters and Reviews

114

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“…Epoxidation has been carried out either homogeneously [8][9][10] or by using a heterogeneous catalyst [11]. In the homogeneous catalysis, peracids are mainly used.…”

Section: Introductionmentioning

confidence: 99%

Modification of soybean oil for intermediates by epoxidation, alcoholysis and amidation

Lee

Hailan

Jin

et al. 2008

Korean J. Chem. Eng.

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Vegetable oils are a major source of many base chemicals. Unfortunately, most vegetable oils exhibit lower thermal and oxidation stability because of double bonds and even worse low-temperature behaviors. These physical and chemical properties can be improved by various chemical modifications. The catalytic hydrogenation of soybean oil (SBO) over 25% Ni/SiO 2 and 5% Pt/C is one of them, and the epoxidation of soybean oil and reduced soybean oil (RSBO) was carried out by using 30% of hydrogen peroxide and acetic acid in the presence of conc. sulfuric acid, and/ or acidic Amberlyst 15 resin catalyst. Various alcohols and amines were added to the epoxidized soybean oil (ESBO) in the hope of improving lubricant properties. The reaction products were carefully analyzed by means of 1 H-NMR, FT-IR spectroscopies and GC-MS spectrometry. This paper covers the epoxidation of virgin and RSBOs, alcoholysis and amidation of ESBO and SBO. Finally, the structures of cross linked products synthesized from ESBO and SBO with 1,6-hexamethylendiamine were proposed.

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“…2,9 Although H 2 O 2 is a very suitable oxidant for this application because of its low price and environmental benignity, its high polarity demands for the use of a suitable solvent to overcome solubility problems of the generally apolar olefins. [10][11][12][13][14] Nevertheless, Li and co-workers reported on reaction-controlled phase transfer catalysis for propylene epoxidation with H 2 O 2 in 2001, 15 which has been commercialized for the epoxidation of cyclohexene in China since 2003. 16 An established class of epoxidation catalysts comprises the titano-silicate materials, including molecular sieves TS-1, TS-2 and Ti-BEA and titanium supported on amorphous silica gel.…”

Section: Introductionmentioning

confidence: 99%

Mechanistic insights in the olefin epoxidation with cyclohexyl hydroperoxide

Hereijgers

Parton

Weckhuysen

2012

Catal. Sci. Technol.

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Olefin epoxidation with cyclohexyl hydroperoxide offers great perspective in increasing the yield from industrial cyclohexane oxidation and the production of epoxides in an apolar medium. Two competing hydroperoxide conversion routes, namely direct epoxidation and thermal decomposition, were identified. The formation of radicals seemed to play a role in both mechanisms. However, olefin epoxidation was found to solely take place at the catalyst. Allylic oxidation of cyclohexene occurs under reaction conditions primarily by molecular oxygen and only constitutes a minor route. The presence of molecular oxygen was found to increase the overall yield of the process by solvent oxidation yielding new cyclohexyl hydroperoxide. Hydrolysis and isomerization of the epoxide were found to be negligible reactions, although the epoxide gets converted at higher concentrations, presumably by the radical initiated polymerization. UV-Vis spectroscopy provided proof for the formation of titanium-hydroperoxide species as the active catalytic site in the direct epoxidation reaction.

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Epoxidation of n-hexene and cyclohexene over titanium-containing catalysts

Cited by 12 publications

References 18 publications

Lubricants from renewable energy sources – a review

Lubricants from renewable energy sources – a review

Modification of soybean oil for intermediates by epoxidation, alcoholysis and amidation

Mechanistic insights in the olefin epoxidation with cyclohexyl hydroperoxide

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