4312-76-9

Basic information

• Product Name: hexyl hydroperoxide
• Synonyms: Hexyl hydroperoxide; hydroperoxide, hexyl
• CAS NO: 4312-76-9
• Molecular Formula: C₆H₁₄O₂
• Molecular Weight: 118.1742
• Mol File: 4312-76-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 182.7°C at 760 mmHg
• Flash Point: 64.3°C
• Density: 0.899g/cm³
• Vapor Pressure: 0.232mmHg at 25°C
• Refractive Index: 1.418
• CAS DataBase Reference: hexyl hydroperoxide(CAS DataBase Reference)
• NIST Chemistry Reference: hexyl hydroperoxide(4312-76-9)
• EPA Substance Registry System: hexyl hydroperoxide(4312-76-9)

Safety Data

• Hazardous Substances Data: 4312-76-9(Hazardous Substances Data)

Upstream product

• 16156-50-6 n-hexyl methanesulfonate 
• 638-45-9 1-Iodohexane 
• 18379-64-1 n-hexyldichloroborane 
• 44767-62-6 n-hexylmagnesium chloride 
• 110-54-3 hexane 
• 111-27-3 hexan-1-ol 
• 16623-96-4 (cyclododecylidene)bishydroperoxide 
• 1427511-73-6 1,1-bis(hexylperoxy)cyclododecane 

Downstream Products

• 16432-53-4 hexane-1,4-diol 
• 66-25-1 hexanal 
• 111-27-3 hexan-1-ol 
• 1003-30-1 2-ethyltetrahydrofuran 

Relevant articles and documents

Synthesis of alkyl hydroperoxides via alkylation of gem -dihydroperoxides

2-Fold alkylation of 1,1-dihydroperoxides, followed by hydrolysis of the resulting bisperoxyacetals, provides a convenient method for synthesis of primary and secondary alkyl hydroperoxides.

Catalytic oxidation of n-hexane on Mn-exchanged zeolites: Turnover rates, regioselectivity, and spatial constraints

The effects of channel structure and spatial constraints on n-hexane oxidation rates and regioselectivity were examined on Mn cations within channels of acidic zeolites. Active Mn cations were placed at exchange sites within channels in 8-membered (ZSM-58), 10-membered (ZSM-5 and ZSM-57), and 12-membered ring (MOR) channels by sublimation of MnI2. Synthesis rates for hexanols (ROH), hexanal/hexanones (R({single bond}H){double bond, long}O), and acids were proportional to hexylhydroperoxide (ROOH) concentrations on all Mn-zeolite catalysts, except Mn-ZSM-58, on which products formed exclusively via noncatalytic autoxidation because of restricted access to Mn cations present within small channels (0.36 nm). Catalytic decomposition of ROOH intermediates occurs on intrachannel Mn cations and is the kinetically relevant step in alkane oxidation. ROOH decomposition rate constants were 2.5, 1.4, and 0.41 mol (mol-Mn h)-1 (mM-ROOH)-1 on Mn-ZSM-5, Mn-ZSM-57, and Mn-MOR (403 K; 0.4 MPa O2), respectively. Regioselectivity was influenced by the constrained environment around Mn cations, which increased terminal selectivities above the values predicted from the relative bond energies of methyl and methylene C{single bond}H bonds in n-hexane. Mn cations within 10-ring channels gave higher terminal selectivities (Mn-ZSM-5: 24%, kprim / ksec = 0.42; Mn-ZSM-57: 14%, kprim / ksec = 0.22) than those within 8-membered or 12-membered rings (Mn-MOR, Mn-ZSM-57: 8-10%, kprim / ksec = 0.12 - 0.14), because of restricted access in ZSM-58 and unconstrained transition states for C{single bond}H bond activation in MOR. Terminal selectivities decreased with increasing alkane conversion, because unselective noncatalytic autoxidation pathways prevail as ROOH concentrations concurrently increase. ROOH intermediates can be scavenged from the extracrystalline liquid phase using H-zeolites with accessible protons, which inhibit unselective noncatalytic reactions and maintain higher terminal selectivities as conversion increases, albeit with a concomitant decrease in the rate of oxidation steps also involving ROOH intermediates.