Some Specific Features in Autoxidation of Methyl Linoleate

Khan, N. A.

doi:10.1139/v59-147

Cited by 20 publications

(6 citation statements)

References 9 publications

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“…The other major absorption at 10.3 ~ that intensifies with time is undoubtedly due to the formation of the trans isomer. These two phenomena have been reported by previous workers (3)(4)(5)(6) and are included here merely to emphasize that methyl linoleate undergoes the same conversions as the more typical drying oils.…”

Section: Discussionsupporting

confidence: 79%

The mechanism of cobalt drier action

Girard

Beispiel

Bricker

1965

J Americ Oil Chem Soc

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The influence of cobalt driers on the initial stages of the drying of polyunsaturated esters has been studied. Cobalt (II) appears to form an unstable complex of variable composition with the polyunsaturated ester. This complex catalyzes the uptake of oxygen and increases the rate of oxygen absorption by the ester. The energy of activation for oxygen uptake by the ester in the presence of cobalt is only ].3 kcal/mole, while in the absence of cobalt, the activation energy is 10.8 keal/mole. The absorption of oxygen by the ester is followed by the formation of hydroxy and/or hydroperoxy groups, the loss of alkene groups, an increase in conjugation and conversion from the cis to the trans isomer. Polymerization occurs during these latter changes.

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Section: Discussionsupporting

confidence: 79%

The mechanism of cobalt drier action

Girard

Beispiel

Bricker

1965

J Americ Oil Chem Soc

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“…For the model compound EL these include the appearance of the bands assigned to ROOH and ROH stretches (around 3400 cm –1 ),42,43 the disappearance of the band associated with cis C= C – H symmetric stretching (3010 cm –1 ),37,42 the appearance of a shoulder (around 1710 cm –1 ) of the carbonyl band, due to the formation of various aldehydes, ketones and esters as the result of β‐scission reactions,37,42 and the appearance of new bands due to C–H wagging of conjugated trans C= C – H (987 and 948 cm –1 ) and isolated trans C= C – H bonds (970 cm –1 ) 37,42,45. These last functionalities are indicative of changes of the originally nonconjugated cis double bonds, initially into hydroperoxide compounds (which contain conjugated cis , trans double bonds)44 and eventually into cross‐linking reaction products (see also Scheme ) 37…”

Section: From Catalysts For Detergent Cleaning To Paint‐drying Catmentioning

confidence: 99%

The Quest for Cobalt‐Free Alkyd Paint Driers

Böer¹,

Wesenhagen²,

Wenker³

et al. 2013

Eur J Inorg Chem

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Paint formulations, based either on organic solvents or on water, often contain alkyd resins that depend on catalysts for their oxidative curing. Cobalt carboxylates are the most widely used to date, but the use of these compounds is under pressure because classification as carcinogens under the REACh system is probable, and as a consequence there is great interest in the development of alternative driers to cobalt-based ones. A variety of manganese and iron carboxylates have been studied as paint drying catalysts in the last[a] Catexel BV, www.eurjic.org MICROREVIEW coating dries. Metal ions and complexes can facilitate these oxidation reactions and polymerisations. During the autooxidation of alkyd paints the unsaturated fatty acids react with molecular oxygen from the air to form -initiallyalkyl hydroperoxides (Scheme 1). [3,4] Subsequent decomposition of these alkyl hydroperoxides yields alkoxy and per-Johannes W. de Boer received his PhD in chemistry (2008) from the University of Groningen, the Netherlands, under the guidance of Prof. Ben L. Feringa and Dr. Ronald Hage and was awarded the Backer Prize by the Royal Dutch Chemical Society for his thesis on manganese-catalysed oxidation reactions. In 2007 he joined Rahu Catalytics, currently Catexel, where he works as Research Principal. His current research interests include the development of new oxidation catalysts and processes for a wide variety of (industrial) applications, focussing on manganese-and iron-catalysed activation of hydrogen peroxide and oxygen. Philana V. Wesenhagen gained her master's degree in chemistry at the University of Groningen in 2006 and joined the team of Rahu Catalytics from 2007 to 2009. After this she switched her fields of interest from chemistry to biotechnology and obtained a second master's degree, in cellular and molecular biotechnology at Wageningen University, in 2011. Currently she is doing her PhD at the Forschungszentrum in Jülich at the Institut für Bio-und Geowissenschaften. Erica C. M. Wenker gained a master's degree in chemistry (2010) at Leiden University, the Netherlands. During her master's she carried out mechanistic research on paint-drying catalysts at Rahu Catalytics. She is currently doing a PhD in coordination chemistry and catalysis under the guidance of Prof. Dr. Elisabeth Bouwman at Leiden University. Karin Maaijen obtained a bachelor's degree in chemistry in 2007 and a master's degree in chemistry and physics (2009) from Utrecht University (the Netherlands) with a major in inorganic chemistry and catalysis. In 2010 she joined Rahu Catalytics, currently Catexel, where she works as a Research Scientist on iron and manganese catalysts for various industrial applications. Franjo Gol gained a master's degree in chemistry and a Dr. rer. nat. in inorganic and organophosphorus chemistry at Wuppertal University. He has worked in the chemical industry for 26 years, initially on the development of water-borne binders for coatings for Herberts and then on binders, metal carboxylates and paint additives for Abshag...

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“…The following mechanism has been postulated, using methyl linoleate, as an illustration of how an activated complex is formed between the -electrons of a double bond and an oxygen molecule (102). This form is stabilized by hydrogen bonding with the protons of the activated methylene group in the 11-position.…”

Section: Polymerization Initiation and Peroxide Formationmentioning

confidence: 99%