65313-46-4

Basic information

• Product Name: 1-Hydroxyhexane-2,5-dione
• Synonyms: 1-Hydroxyhexane-2,5-dione
• CAS NO: 65313-46-4
• Molecular Formula: C₆H₁₀O₃
• Molecular Weight: 130.14
• Mol File: 65313-46-4.mol
• Article Data: 16

Chemical Properties

• Melting Point: 51 °C
• Boiling Point: 82-85 °C(Press: 0.5 Torr)
• Appearance: /
• Density: 1.090±0.06 g/cm3(Predicted)
• PKA: 12.95±0.10(Predicted)
• CAS DataBase Reference: 1-Hydroxyhexane-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Hydroxyhexane-2,5-dione(65313-46-4)
• EPA Substance Registry System: 1-Hydroxyhexane-2,5-dione(65313-46-4)

Safety Data

• Hazardous Substances Data: 65313-46-4(Hazardous Substances Data)

Usage

General Description

1-Hydroxyhexane-2,5-dione, also known as 3-hydroxy-5-hexanone, is a chemical compound with the molecular formula C6H10O3. It is a cyclic diketone that is commonly used as a building block in organic synthesis. 1-Hydroxyhexane-2,5-dione is known for its pleasant fruity odor and is used as a flavoring agent in the food industry. It is also used as a precursor in the production of pharmaceuticals and other fine chemicals. Additionally, it has been studied for its potential applications in various fields, including its use as a chelating agent and its role in the formation of molecular complexes. However,

Upstream product

• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 470-23-5 D-fructose 
• 57-48-7 D-Fructose 

Downstream Products

• 765-70-8 3-methyl-1,2-cyclopentanedione 
• 6126-49-4 tetrahydro-5-methyl-2-furanmethanol 
• 65709-88-8 Z-5-Hydroxy-hexen-2 
• 54560-70-2 (+/-)-(E)-hex-4-en-2-ol 
• 123-76-2 levulinic acid 
• 26629-21-0 2,3-dihydro-1H-1-methylcyclopenta(b)quinoxaline 
• 80-71-7 2-hydroxy-3-methylcyclopent-2-en-1-one 

Relevant articles and documents

Preparation of 1-Hydroxy-2,5-hexanedione from HMF by the Combination of Commercial Pd/C and Acetic Acid

The development of a simple and durable catalytic system for the production of chemicals from a high concentration of a substrate is important for biomass conversion. In this manuscript, 5-hydroxymethylfurfural (HMF) was converted to 1-hydroxy-2,5-hexanedione (HHD) using the combination of commercial Pd/C and acetic acid (AcOH) in water. The influence of temperature, H2 pressure, reaction time, catalyst amount and the concentration of AcOH and HMF on this transformation was investigated. A 68% yield of HHD was able to be obtained from HMF at a 13.6 wt% aqueous solution with a 98% conversion of HMF. The resinification of intermediates on the catalyst was characterized to be the main reason for the deactivation of Pd/C. The reusability of the used Pd/C was studied to find that most of the activity could be recovered by being washed in hot tetrahydrofuran.

Selective conversion of 5-hydroxymethylfurfural to diketone derivatives over Beta zeolite-supported Pd catalysts in water

Conversion of 5-hydroxymethylfurfural (HMF) in water to the linear diketone derivatives 1-hydroxyhexane-2,5-dione (HHD) and 2,5-hexanedione (HXD) was investigated over a series of Beta zeolite-supported transition metal catalysts (Co, Ni, Cu, Ru, Pd). Their catalytic performance was tested in a batch stirred reactor (T = 110 °C, PH2 = 20 bar) with Pd showing the highest activity and selectivity to HHD and HXD. The effects of Pd particle size, zeolite Si/Al ratio and reaction conditions (T = 80–155 °C, PH2 = 5–60 bar) were also investigated. The incorporation of Pd into Beta zeolite by the deposition-coprecipitation method produced the most efficient catalyst, affording complete HMF conversion (T = 110 °C, PH2 = 60 bar) predominantly to HHD (68% selectivity) and HXD (8% selectivity). The combination of a bifunctional acid/redox solid catalyst and water enhances the hydrolytic ring-opening and subsequent hydrogenation of the furan ring. Catalytic activity can be partially restored by a simple regeneration treatment. This work establishes a catalytic route to produce valuable diketone derivatives from renewable furanic platform sources in water.

Conversion of HMF to methyl cyclopentenolone using Pd/Nb2O5 and Ca-Al catalysts: Via a two-step procedure

The catalytic conversion of HMF to 2-hydroxy-3-methyl-2-cyclopenten-1-one (MCP), which is a valuable edible essence that has traditionally been obtained from adipic acid, was achieved with an isolated yield of 58%. This procedure comprised two steps: the hydrogenation of 5-hydroxymethylfurfural (HMF) to 1-hydroxy-2,5-hexanedione (HHD) in water on Pd/Nb2O5 catalysts and then the isomerization of HHD to MCP in the presence of a base. The Nb2O5 supports, which were acidic, were characterized by FTIR, XRD and NH3-TPD. The supported Pd/Nb2O5 catalysts, in which Pd was highly dispersed, were synthesized employing cyclohexene as a reductant and were characterized by XRD, TEM, ICP-AES, XPS, EDX and CO pulse chemisorption. The high conversion of HMF was attributed to the high dispersion of Pd, and the acidity of the supports led to high selectivity for HHD. The conversion of HHD to MCP was an intramolecular aldol condensation reaction, and the protonic solvent favored this reaction. Ca-Al was proved to be an effective solid base for the conversion of HHD to MCP in water.