2388-12-7

Basic information

• Product Name: peroxylauric acid
• Synonyms: peroxylauric acid;1-Hydroperoxycarbonylundecane;Dodecaneperoxoic acid;Perlauric acid;Peroxydedecanoic acid;Peroxydodecanoic acid;Nsc74803;Perdodecanoic acid
• CAS NO: 2388-12-7
• Molecular Formula: C₁₂H₂₄O₃
• Molecular Weight: 216.31716
• EINECS: 219-217-9
• Mol File: 2388-12-7.mol
• Article Data: 14

Chemical Properties

• Melting Point: 51-52 °C
• Boiling Point: 307°Cat760mmHg
• Flash Point: 105.5°C
• Appearance: /
• Density: 0.95g/cm³
• Vapor Pressure: 6.92E-05mmHg at 25°C
• Refractive Index: 1.448
• PKA: 7.92±0.40(Predicted)
• CAS DataBase Reference: peroxylauric acid(CAS DataBase Reference)
• NIST Chemistry Reference: peroxylauric acid(2388-12-7)
• EPA Substance Registry System: peroxylauric acid(2388-12-7)

Safety Data

• Hazardous Substances Data: 2388-12-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 4037, 1955 DOI: 10.1021/ja01620a023

InChI:InChI=1/C12H24O3/c1-2-3-4-5-6-7-8-9-10-11-12(13)15-14/h14H,2-11H2,1H3

Upstream product

• 86960-46-5 4-n-decanoyloxybenzoic acid 
• 1956-11-2 p-Nitrophenyl laurate 
• 112-54-9 Dodecanal 
• 143-07-7 lauric acid 
• 180424-43-5 1-hydroxycyclohexyl perdodecanoate 
• 137846-25-4 2-methoxyprop-2-yl peroxydodecanoate 
• 112-16-3 n-dodecanoyl chloride 

Downstream Products

• 105-74-8 dilauryl peroxide 
• 124-07-2 Octanoic acid 
• 180424-43-5 1-hydroxycyclohexyl perdodecanoate 
• 112-16-3 n-dodecanoyl chloride 
• 67-66-3 chloroform 
• 2473-03-2 1-chloroundecane 
• 67-72-1 hexachloroethane 
• 143-07-7 lauric acid 
• 76077-77-5 ClMn(IV)(O)(tetraphenylporphyrin) 
• 78833-34-8 (tetraphenylporphinato)oxochromium(IV) 
• 544-76-3 Hexadecane 
• 110-54-3 hexane 
• 112-40-3 dodecane 
• 124-18-5 decane 

Relevant articles and documents

-

-

Aerobic oxidation of aldehydes to acids with N-hydroxyphthalimide derivatives

The N-hydroxyphthalimide derivative-mediated aerobic oxidation of a selection of aldehydes to the corresponding carboxylic acids in air is described. This reaction proceeds via rearrangement of the Creigee (carboxylic peracid) intermediate and/or by the treatment of H2O and/or sulfides. Optimization of reaction conditions established NHNPI (14) as a mild catalyst for the oxidation reaction in MeCN under an atmosphere of air.

Perdecanoic acid as a safe and stable medium-chain peracid for Baeyer-Villiger oxidation of cyclic ketones to lactones

Stability studies dedicated to high-energy compounds for a series of linear peracids (C6-C12), including sensitivity to mechanical impulse (shock and friction), as well as electrical (spark) and thermal sensitivity (temperature and heat of decomposition), were presented in this work for the first time. Studies revealed that all peracids were insensitive to shock, while in the case of the other sensitivity tests sharp differences between results for C8 and C10 peracids were observed. Taking into account the relatively high initial temperature of decomposition (above 64 °C) perdecanoic acid was selected as a safe alternative to commonly used hazardous short-chain peracids. Next, a new method for the Baeyer-Villiger oxidation was presented. Oxidation of 2-adamantanone was chosen as a model reaction. Peroctanoic, perdecanoic and perdodecanoic acids were tested as oxidants. Peroctanoic acid was the most reactive but taking into account both safety and kinetic issues, perdecanoic acid was selected for the further studies. The influence of reaction conditions on reaction rate was investigated. Optimized reaction conditions were suggested (two-fold molar excess of peracid with respect to the ketone, toluene as a solvent, 35 °C). This exploratory study offers promise with regard to the development of safer alternatives to peracetic acid in industrial oxidation.