1,6-Hexanediol diglycidyl ether

• CAS: 16096-31-4
• Catalog Number: ACM16096314-1
• Category: Main Products
• Molecular Weight: 230.3
• Molecular Formula: C12H22O4
• Synonyms: 1,6-Bis(2,3-epoxypropoxy)hexane
• Appearance: Colorless liquid
• Active Content: 95%
• Physical State: Liquid

Case Study

Solid Fuel Ramjet Fuels Based on 1,6-Hexanediol Diglycidyl Ether

McDonald, Brian, et al. Fuel, 2020, 278, 118354.

Solid fuel ramjet fuels (SFRJ) have high material density and net pulse density. This work independently theoretically evaluates the fuel value of a series of epoxy resins and curing agents in SFRJ applications. The study identified polyethers as the preferred material, and the material combination consisting of 1,6-hexanediol diglycidyl ether (HDGE) and methyltetrahydrophthalic anhydride as the epoxy component and curing agent, respectively, showed the best performance.
SFRJ polymer properties
· This fuel boasts a high material density and exhibits exceptional energy per unit mass of reactants when compared to other standard SFRJ polymers.
· With a Shore-A hardness rating of 38, the material is structurally robust, suitable for applications in a highly metalized setup.
· Although tear resistance was not quantitatively measured, a qualitative evaluation under shear loading indicates satisfactory tear strength.
· Data from TGA, DSC, and PGCMS reveal favorable performance with decomposition temperatures and by-products that support autoignition at air inlet temperatures of 421 °C or higher.
· Testing in a direct connect combustor demonstrates stable combustion and regression rates consistent with typical SFRJ fuels, providing sufficient design flexibility.
· The measured characteristic exhaust velocity efficiencies exceed 92% across all tested pressure levels.

Concomitant Reactivity Between Reactive Diluents Such as 1,6-Hexanediol Diglycidyl Ether in Epoxy Resin Systems

Geier, Johannes, et al. Contact Dermatitis, 2016, 74(2), 94-101.

The sensitivity of epoxy resin systems (ERS) also depends on reactive diluents and hardeners in addition to the base resin. This work aimed to analyze the concomitant reactivity between reactive diluents and hardeners in related patients to investigate the ERS sensitization capacity.
Reactivity between reactive diluents
· Unlike hardeners, which generally have significantly different chemical structures, some reactive diluents are chemically similar. Both 1,6-hexanediol diglycidyl ether (1,6-HDDGE) and 1,4-butanediol diglycidyl ether (1,4-BDDGE) are aliphatic glycidyl ethers that differ by just two carbon atoms in chain length, leading to the expectation of immunological cross-reactivity.
· A summary table shows the reactions of patients who have sensitivities to diglycidyl ether of bisphenol A (DGEBA) resin against various reactive diluents. Out of the 452 patients tested for both compounds, 191 people (42.3%) reacted to 1,6-HDDGE while 155 people (34.3%) reacted to 1,4-BDDGE. The group of 144 patients who tested positive for both substances formed 75.4% of the group that reacted to 1,6-HDDGE while making up 92.9% of those who responded to 1,4-BDDGE.
· The concomitant reaction to 1,6-HDDGE and 1,4-BDDGE may indicate the presence of a common allergenic compound derived from the metabolism of 1,4-BDDGE.

1,6-Hexanediol diglycidyl ether for cross-linking treatment of commercially available reverse osmosis membranes

Xinyu, W. E. I., et al. Chinese Journal of Chemical Engineering 21.5 (2013): 473-484.

A commercially available aromatic polyamide reverse osmosis membrane was cross-linked to improve its chlorine resistance. Cross-linking agents including 1,6-hexanediol diglycidyl ether, dimethacrylic acid dichloride, and hexamethylene diisocyanate were used in the experiment. These esters have long and flexible aliphatic chains and are highly reactive with N H groups. Attenuated total reflection Fourier transform infrared spectroscopy verified that the cross-linking treatment successfully prepared highly cross-linked membranes. The results showed that the cross-linking agent was attached to the membrane surface by reaction with amine and amide II groups, which can be confirmed by surface charge measurements. According to contact angle measurements, the cross-linking treatment reduced the hydrophilicity of the membrane by introducing methylene groups into the membrane surface.
The cross-linking treatment of the aromatic polyamide RO membrane was as follows. The original membrane piece (13 cm × 11 cm) was fixed in a polytetrafluoroethylene frame to ensure that the reactant solution was in contact with the membrane barrier layer only. The membrane surface was rinsed with pure water and dried by nitrogen purge. 1,6-Hexanediol diglycidyl ether was dissolved in petroleum ether. APC and HDI were dissolved in n-hexane. The solution was sonicated to ensure complete dissolution. Contact with water should be avoided during the entire dissolution process. The original membrane was covered with the crosslinker solution for about 5 min, and then the excess solution was removed and dried with nitrogen at about 30 kPa. The membrane filled with the crosslinker was then placed in an oven and the crosslinking reaction was carried out at 60 °C for 60 min.

1,6-hexanediol diglycidyl ether skin permeation and metabolism studies

Boogaard, P. J., M. A. Denneman, and N. J. Van Sittert. Xenobiotica 30.5 (2000): 469-483.

Glycidyl ethers (GE) are an important class of industrial chemicals that are considered to have potential in vivo mutagenicity. The percutaneous permeation and metabolism of representatives of different classes of GE were studied in mouse and excised human skin as well as rat skin to determine the apparent permeation constants, lag times, and metabolic profiles. Five different GEs, namely, diglycidyl ethers of bisphenol A (BADGE), 4,49-dihydroxy-3,3,5,5-tetramethylbiphenyl and 1,6-hexanediol diglycidyl ether (HDDGE) and diglycidyl ethers of 1-dodecane and o-cresol (o-CGE), were synthesized by reaction of their alcohols with epichlorohydrin. Their radiolabeled analogs were synthesized with [U-14C]-epichlorohydrin and 14C-labeled. There was a wide variation in the percutaneous permeability of different GEs. Overall, the permeability of mouse full-thickness skin was higher than that of rat skin grafts, while human skin grafts had the lowest permeability.
GE system A was used for BADGE, YX4000 system B for 1,6-hexanediol diglycidyl ether (HDDGE) system C. The (radioactive) products formed were identified by coelution with reference standards and LC-MS. At the end of the experiment, the skin was removed from the cells and soaked twice in 2 ml of ethyl acetate for 12 h to dissolve the GE remaining on the skin. The combined ethyl acetate fractions were dissolved in the mixture and the radioactivity was determined by LSC. The skin itself was dissolved in 1.0 ml of tetraethylammonium hydroxide for 48 h and the total radioactivity in the resulting solution was determined by LSC. The receptor UIDs and tubing remaining in the cells were collected; the tubing was subsequently flushed with receptor UIDs and water. The combined UIDs were counted by LSC. Finally, to obtain mass balance, intact cells were sonicated individually in 100 ml of ethyl acetate for 30 min to solubilize any traces of GE, and aliquots of ethyl acetate were counted by LSC.

Custom Q&A

What is the product name of CAS number 16096-31-4?

The product name is 1,6-Hexanediol diglycidyl ether.

What is the molecular weight of 1,6-Hexanediol diglycidyl ether?

The molecular weight is 230.3.

What is another name for 1,6-Hexanediol diglycidyl ether?

Another name for it is 1,6-Bis(2,3-epoxypropoxy)hexane.

What is the molecular formula of 1,6-Hexanediol diglycidyl ether?

The molecular formula is C12H22O4.

What is the appearance of 1,6-Hexanediol diglycidyl ether?

It is a colorless liquid.

What percentage of actives does 1,6-Hexanediol diglycidyl ether contain?

It contains 95% actives.

In what physical state does 1,6-Hexanediol diglycidyl ether exist?

It exists in a liquid state.

What are the typical applications of 1,6-Hexanediol diglycidyl ether?

It is used as an epoxy resin diluent and as an intermediate in organic synthesis.

How is 1,6-Hexanediol diglycidyl ether commonly used in industrial processes?

It is commonly used as a diluent in epoxy resin formulations.

What is the CAS number of 1,6-Hexanediol diglycidyl ether?

The CAS number is 16096-31-4.