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Antioxidants solubilization Disclosure Number: IPCOM000237403D
Publication Date: 2014-Jun-17
Document File: 2 page(s) / 14K

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Use of dioxolanes, in particular 2,2-dimethyl-1,3-dioxolane-4-methanol (CAS Nº 100-79-8), 2-isobutyl-2-methyl-1,3-dioxolane-4-methanol (CAS Nº 5660-53-7) and 2,2-dimethyl-1,3-dioxolane-4-acetate (CAS Nº 14739-11-8) to solubilize antioxidants, notably hindered phenols that are typically used in plastics, elastomers, synthetic fibers, fuels, lubricants and foods. As known antioxidants that are easily solubilized by the said dioxolane compounds, we can cite 3,5-di-tert-butyl-4-hydroxyhydrocinnamate methane (CAS Nº 6683-19-8), 3,5-di-tert-butyl-4-hydroxytoluene (CAS Nº 128-37-0), 2-tert-butylhydroquinone (CAS Nº 1948-33-0), 6-tert-butyl-4-methylphenol (CAS Nº 119-47-1), 2,6-di-tert-butylphenol (CAS Nº 128-39-2), thiodiethylene-bis(3,5-di-tert-butyl-4-hydroxyhydrociannamate) (CAS Nº 41484-35-9), 3,5-di-tert-butyl-4-hydroxyphenyl propionamide (CAS Nº 23128-74-7) and 6-tert-butyl-3-methylphenol (CAS Nº 85-60-9). The resulting solutions remain stable under different conditions of humidity and temperature, these solvents are responsible for providing processing stability and long term heat stability to different application, maximizing their storage life.

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    The constant search for sustainable alternatives in several fields of the chemical industry, such as mining, pharmaceutical, agro, paints & coatings, leather, home & personal care, construction, electronics, etc, led to development of solvents that meet the three pillars of sustainability (economical, environmental and social). Such solvents present competitiveness, very good performance in the application, and additionally low toxicity to humans and environment. One application where those solvents can be used, is on the solubilization of antioxidants.

    Oxygen is obviously a key factor in oxidation. In the ground state, it exists as a biradical and reacts readily with carbon free radicals, even at ambient temperature, to yield peroxy radicals. The reaction of carbon free radicals with oxygen has such low activation energy that it is the preferred pathway when not limited by oxygen diffusion. The resulting peroxy radicals abstract hydrogen from the substrate, generating another carbon free radical and a hydroperoxide. This reaction has severe consequences for the organic material because it is a chain reaction that has a significant length and can cause extensive localized oxidation before termination. (1)

    Unless these radical reactions are inhibited with antioxidants, the organic substance can quickly deteriorate. The physical properties and appearance of polymers and elastomers are reduced, fuels and lubricants lose properties, and foods lose their flavor and become rancid. (1) Antioxidants inhibit the autoxidation of substances by intervening in reactions of free radicals. They are molecules that can prevent or delay the oxidation of other molecules by hindering the reaction with atmospheric oxygen or other chemicals. Both natural as well as synthetic antioxidants are added to many products, being frequently used in industrial process, and its more common use is as stabilizers in fuel and lubricant to prevent oxidation, and also in gasoline to prevent the polymerization that leads to the formation of fouling residues...