34067-76-0

Basic information

• Product Name: HEXANAL,6-HYDROXY-
• Synonyms: 6-hydroxy caproaldehyde;6-hydroxyhexanal;HEXANAL,6-HYDROXY-
• CAS NO: 34067-76-0
• Molecular Formula: C₆H₁₂O₂
• Molecular Weight: 116.15828
• Mol File: 34067-76-0.mol

Chemical Properties

• Boiling Point: 200.2 °C at 760 mmHg
• Flash Point: 78.4 °C
• Appearance: /
• Density: 0.949 g/cm³
• Vapor Pressure: 0.0815mmHg at 25°C
• Refractive Index: 1.429
• CAS DataBase Reference: HEXANAL,6-HYDROXY-(CAS DataBase Reference)
• NIST Chemistry Reference: HEXANAL,6-HYDROXY-(34067-76-0)
• EPA Substance Registry System: HEXANAL,6-HYDROXY-(34067-76-0)

Safety Data

• Hazardous Substances Data: 34067-76-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 774, 1986 DOI: 10.1055/s-1986-31775

InChI:InChI=1/C6H12O2/c7-5-3-1-2-4-6-8/h5,8H,1-4,6H2

Upstream product

• 25176-55-0 methyl 6,6-dimethoxyhexanoate 
• 629-11-8 1,6-hexanediol 
• 627-93-0 hexanedioic acid dimethyl ester 
• 4547-43-7 methyl 6-hydroxycaproate 
• 106-69-4 hexane-1,2,6-triol 
• 538-68-1 pentylbenzene 
• 359-48-8 trifluoroacetyl peroxide 

Downstream Products

• 1191-25-9 6-Hydroxyhexanoic acid 
• 166819-33-6 6-(Methyl-diphenyl-silanyloxy)-hexanal 
• 804556-25-0 6-trityloxyhexanal 
• 803733-15-5 3-(4-cyanophenyl)-9-hydroxy-1-phenylnonane-1,4-dione 
• 528571-18-8 1-benzyl-3-bromo-4-(5-chloro-pentyl)-3-(toluene-4-sulfonyl)-piperidine-2,6-dione 
• 528570-89-0 1-benzyl-3-bromo-3-(4-methylphenylsulfonyl)-4-(5-hydroxypentyl)piperidine-2,6-dione 
• 109359-36-6 2-methyl-1,8-octanediol 
• 143605-56-5 (1R,2R,4aS,8aS)-2-<(R)-2-hydroxybutyl>-1,3-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid 
• 154966-08-2 (1S,2S,4aR,8aR)-2-<(R)-2-hydroxybutyl>-1,3-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid 
• 166819-34-7 C₂₅H₃₈O₂Si₂ 
• 462-12-4 8-fluoro-3-methyloctanoic acid 
• 332-97-8 ethyl 8-fluorooctanoate 
• 93892-06-9 8-hydroxyoctanoic acid ethyl ester 
• 144682-03-1 ethyl 8-[[(4-methylphenyl)sulfonyl]oxy]octanoate 

Relevant articles and documents

Influence of Dioxygen on the Promotional Effect of Bi during Pt-Catalyzed Oxidation of 1,6-Hexanediol

A series of carbon-supported, Bi-promoted Pt catalysts with various Bi/Pt atomic ratios was prepared by selectively depositing Bi on Pt nanoparticles. The catalysts were evaluated for 1,6-hexanediol oxidation activity in aqueous solvent under different dioxygen pressures. The rate of diol oxidation on the basis of Pt loading over a Bi-promoted catalyst was 3 times faster than that of an unpromoted Pt catalyst under 0.02 MPa of O2, whereas the unpromoted catalyst was more active than the promoted catalyst under 1 MPa of O2. After liquid-phase catalyst pretreatment and 1,6-hexanediol oxidation, migration of Bi on the carbon support was observed. The reaction order in O2 was 0 over Bi-promoted Pt/C in comparison to 0.75 over unpromoted Pt/C in the range of 0.02-0.2 MPa of O2. Under low O2 pressure, rate measurements in D2O instead of H2O solvent revealed a moderate kinetic isotope effect (rateH2O/rateD2O) on 1,6-hexanediol oxidation over Pt/C (KIE = 1.4), whereas a negligible effect was observed on Bi-Pt/C (KIE = 0.9), indicating that the promotional effect of Bi could be related to the formation of surface hydroxyl groups from the reaction of dioxygen and water. No significant change in product distribution or catalyst stability was observed with Bi promotion, regardless of the dioxygen pressure.

Efficient and Selective Cu/Nitroxyl-Catalyzed Methods for Aerobic Oxidative Lactonization of Diols

Cu/nitroxyl catalysts have been identified that promote highly efficient and selective aerobic oxidative lactonization of diols under mild reaction conditions using ambient air as the oxidant. The chemo- and regioselectivity of the reaction may be tuned by changing the identity of the nitroxyl cocatalyst. A Cu/ABNO catalyst system (ABNO = 9-azabicyclo[3.3.1]nonan-N-oxyl) shows excellent reactivity with symmetrical diols and hindered unsymmetrical diols, whereas a Cu/TEMPO catalyst system (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyl-N-oxyl) displays excellent chemo- and regioselectivity for the oxidation of less hindered unsymmetrical diols. These catalyst systems are compatible with all classes of alcohols (benzylic, allylic, aliphatic), mediate efficient lactonization of 1,4-, 1,5-, and some 1,6-diols, and tolerate diverse functional groups, including alkenes, heterocycles, and other heteroatom-containing groups.

Perspectives on the kinetics of diol oxidation over supported platinum catalysts in aqueous solution

The catalytic oxidation of a variety of terminal alcohols was performed over Pt/C with 10 bar dioxygen at 343 K in aqueous solvent at low pH. The influences of Pt particle size, carbon support, alcohol structure, and start-up conditions were explored. Although the turnover frequency was not affected by particle size or the carbon support, the structure of the alcohols affected their initial rate of conversion. Both the rate of oxidation of α,ω-diols and selectivity of the diols to the diacids increased with increasing carbon chain length. The rate of 1,6-hexanediol oxidation was independent of dioxygen pressure and the order of reaction with respect to diol concentration depended on the start-up conditions. A kinetic model involving two types of metal sites was proposed to account for the experimental observations.

PROCESS FOR PREPARING PLASTICS USING 1,6-HEXANEDIOL HAVING AN ALDEHYDE CONTENT OF LESS THAN 500 PPM

The present invention relates to a process for preparing plastics using 1,6-hexanediol having an aldehyde content of less than 500 ppm, a process for preparing 1,6-hexanediol having an aldehyde content of less than 500 ppm and also 1,6-hexanediol having an aldehyde content of less than 500 ppm.

METHOD FOR PRODUCING LACTONES FROM DIOLS

The present invention provides a process for preparing lactones from optionally substituted, saturated aliphatic diols having from five to 20 carbon atoms between the two ring-closing hydroxyl groups by catalytic dehydrogenation and cyclization in the liquid phase over at least one catalyst.

Neighbouring Hydroxy Group Participation in the acid-catalyzed Reaction of Pentane-1,4-diol and -1,2,5-triol and Hexane-1,5-diol and -1,2,6-triol

Rate constants have been determined and product analysis made for the acid-catalysed reaction in aqueous solution of ω-primary-secondary polyols HO(CH2)nCHOHX; n = 3 or 4, X = CH3 or CH2OH.The pentane series, n = 3, give five membered cyclic ethers, O-5 ethers in > 90percent yield, while the hexane series, n = 4, give O-6 ethers in ca.35 to 40percent yield.For the pentane series it is known that the cyclisation results from reaction at the hindered primary reaction site, and it is shown here that this is occuring with anchimeric assistance.For the hexane series inter- andintramolecular processes are competitive and anchimeric assistance is slight or absent, while cyclisation at the secondary as well as the pimary reaction site is feasible.It is proposed that neighbouring hydroxy group participation in the reaction of all these polyols is a concerted process.

Trifluoroperacetic Acid. Oxidation of Aromatic Rings

Trifluoroperacetic acid is an oxidizing reagent capable of converting alkylbenzenes to the corresponding aliphatic carboxylic acids.No trace of aromatic carboxylic acid is ever observed.Aromatic heterocyclic compounds do not behave like their hydrocarbon analogues.Quinoline and pyridine are oxidized to the corresponding N-oxides, and dibenzothiophene is oxidized to the sulfone.No destruction of the ring is found in these latter three cases.The reaction mixture of hydrogen peroxide and trifluoroacetic acid undergoes a decomposition reaction to form carbon dioxide and fluoroform.The rate of this decomposition is slow compared to the oxidation so that ist does not interfere with the primary reaction process.However, attempts to quantify the amount of aromatic carbons in a compound or mixture of compounds must be done with caution.