Synthesis of azelaic acid from vegetable oil‐based feedstocks

Köckritz, Angela; Martin, Andreas

doi:10.1002/ejlt.201000117

Cited by 114 publications

(87 citation statements)

References 40 publications

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“…It represents an important transformation of alkenes to carbonyl compounds. In general, the reaction is performed using ozone [1], stoichiometric oxidants such as OsO 4 and NaIO 4 or transition metal catalysts in combination with oxidants such as NaOCl, H 2 O 2 [2], and tert-BuOOH [3]. However, most of the reported oxidation procedures use toxic, hazardous and expensive reagents and produce large amounts of waste.…”

Section: Introductionmentioning

confidence: 99%

Solvent-free aerobic oxidative cleavage of alkenes catalyzed by N-hydroxyphthalimide

Pyszny

Orlińska

2017

Reac Kinet Mech Cat

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The aerobic oxidative cleavage of a-methylstyrene and other benzylic olefins catalyzed by N-hydroxyphthalimide (NHPI) under solvent-free conditions is described. The reaction was remarkably accelerated by the addition of azo-initiator (2,2 0 -azobis(2-methylpropionitryl)) or transition metal salts (Mn, Cu, Co) in combination with NHPI. Alkylammonium salts and acetophenone were successfully applied to increase the solubility of the polar NHPI catalyst in non-polar substrates. The effects of the catalyst and reaction parameters on the conversion of the substrate and the selectivity for ketones were investigated. New insights into the oxidation mechanism and NHPI-ammonium salt interaction are presented.

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Section: Introductionmentioning

confidence: 99%

Solvent-free aerobic oxidative cleavage of alkenes catalyzed by N-hydroxyphthalimide

Pyszny

Orlińska

2017

Reac Kinet Mech Cat

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“…Alternative technologies for oxidatively cleaving oleic acid have been reviewed, but in conclusion the use of ozone is still the best method. This is particularly true if the ozonolysis is conducted in pelargonic acid as the solvent, because in this way the workup of the product mixture is considerably simplified [186].…”

Section: ð71þmentioning

confidence: 99%

Oxidation

Teles

Hermans

Franz³

et al. 2015

Ullmann's Encyclopedia of Industrial Chemistry

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The article contains sections titled: 1. Introduction 2. Overview of industrial oxidation processes 2.1. Inorganic chemicals 2.1.1. Sulfur derivatives 2.1.2. Carbon derivatives 2.1.3. Nitrogen derivatives 2.1.4. Chlorine derivatives 2.2. Organic chemicals 2.2.1. Olefins and alkynes 2.2.2. Epoxides 2.2.3. Hydroperoxides 2.2.4. Alcohols 2.2.5. Aldehydes 2.2.6. Ketones 2.2.7. Phenols and derivatives 2.2.8. Carboxylic acids, saturated 2.2.9. Carboxylic acids and anhydrides, unsaturated 2.2.10. Carboxylic acids and anhydrides, aromatic 2.2.11. Esters, lactones and carbonates 2.2.12. Nitriles 2.2.13. Oxidized nitrogen compounds 2.2.14. Chlorinated compounds 2.2.15. Sulfur compounds 3. Thermodynamics; Stability of Hydrocarbons 4. Reaction Types 5. Homolytic Oxidation 5.1. Historical Development; Reaction Mechanism; Radical Reactivity 5.2. Kinetics of Autoxidation 5.3. Differences between Liquid‐ and Gas‐Phase Autoxidations 5.4. Homolytic Oxidation in the Liquid Phase 5.4.1. Secondary Reactions of Radicals, Peroxides, and other Intermediates 5.4.2. Metal Catalysis in Homolytic Liquid‐Phase Oxidation 5.4.3. Inhibitors of Homolytic Liquid‐Phase Oxidation 5.4.4. Special Cases of Homolytic Oxidation 5.4.5. Process Technology of Homolytic Liquid‐Phase Oxidation 5.5. Homolytic Gas‐Phase Oxidation 5.6. Gas Explosions and Safety Data 6. Heterolytic Oxidation 6.1. Heterolytic Oxidation in the Liquid Phase 6.2. Heterogeneously Catalyzed Gas‐Phase Oxidation 6.2.1. Oxidation Catalysts 6.2.2. Process Technology of Heterogeneously Catalyzed Oxidations

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“…Azelaic acid (1,9-nonanedioic acid), for example, is produced industrially via ozonolysis of oleic acid on a scale of several 1000 tons per year. 7 However, ozonolysis is a technically challenging and potentially hazardous process. An attractive concept of an algae-based refinery to produce mid-chain olefins and carboxylic acids or esters is the utilization of the double bond of unsaturated fatty acids in a crossmetathesis reaction.…”

Section: Introductionmentioning

confidence: 99%

Mid-chain carboxylic acids by catalytic refining of microalgae oil

et al. 2017

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Microalgae oil serves as a feedstock for a biorefinery approach to mid-chain (di-)carboxylic acid esters, currently only accessible via demanding synthetic routes. Via the butenolysis of mono-and poly-unsaturated fatty acids, short-chain unsaturated fatty acid methyl esters and mono-and di-enes were produced in a high selectivity. These olefins were further processed into value added linear mid-chain (di-)carboxylic acid esters via isomerizing alkoxycarbonylation. Model compounds such as eicosapentaenoic acid were used to study the reactions including the screening of metathesis catalysts and to identify all formed products. Notably, eicosapentaenoic acid, a five-fold unsaturated fatty acid relatively abundant in algae, is successfully converted to four equivalents of heptadiene, which was carbonylated to the linear diester (dimethyl azelate). The butenolysis and subsequent isomerizing alkoxycarbonylation were performed on the algae oil extracted from the diatom Phaeodactylum tricornutum. Despite the multicomponent mixture of numerous lipids and non-lipid compounds present in algae oil, high conversion and high selectivity for the desired products were achieved in both reactions. This approach provides access to several carboxylic mono-and di-acid esters of chain length ranging from C6 to C12 (amongst others azelaic acid ester, suberic acid ester and dodecanedioic acid ester), that are in demand but to which access is limited currently, fully based on algae oils as a renewable resource.

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Synthesis of azelaic acid from vegetable oil‐based feedstocks

Abstract: A multitude of synthesis methods for azelaic acid is evaluated in terms of feasibility and sustainability. Up to now, no alternative to industrially employed ozonolysis of oleic acid was developed.

Cited by 114 publications

References 40 publications

Solvent-free aerobic oxidative cleavage of alkenes catalyzed by N-hydroxyphthalimide

Solvent-free aerobic oxidative cleavage of alkenes catalyzed by N-hydroxyphthalimide

Oxidation

Mid-chain carboxylic acids by catalytic refining of microalgae oil

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