1,6-Hexanediol

Chemical properties

white waxy flakes

The Uses of 1,6-Hexanediol

1,6-Hexanediol is used in polymer synthesis such as polyester, polyurethane and nylon. It is used as an intermediate to adhesives, acrylics and dyestuffs. Further, it is employed in gasoline refining and pharmaceutical production.

The Uses of 1,6-Hexanediol

Solvent, intermediate for high polymers (nylon, polyesters), coupling agent, coil coating.

The Uses of 1,6-Hexanediol

1,6-Hexanediol can be used for a variety of applications such as:

• a structure-directing agent for the synthesis of ZSM-5 zeolite
• a solvent for titanium tetraisopropoxide to form titanium oxide (TiO₂) nanocrystals
• a phase change material in combination with lauric acid for thermal energy storage applications

What are the applications of Application

1,6-Hexanediol is a useful alcohol for proteomics research

Definition

ChEBI: A diol that is hexane substituted by hydroxy groups at positions 1 and 6.

Production Methods

1,6-Hexanediol is produced industrially by the catalytic hydrogenation of adipic acid or of its esters. Mixtures of dicarboxylic acids and hydroxycarboxylic acids with C6 components formed in other processes (e.g., in cyclohexane oxidation) are also used. Esterifification of "distillation heavies" with lower alcohols is often carried out before hydrogenation. The acids are hydrogenated continuously at 170-240 ℃ and at 15.0-30.0 MPa on a suitable catalyst either in a trickle-flflow (downflflow) or a bubble-flflow (upflflow) fifixed-bed reactor. The reactor temperature is controlled by circulating part of the reactor discharge. The hydrogen required for the hydrogenation is fed together with the recycle gas through the recycle gas compressor to the reactor. Side products of the synthesis are alcohols, ethers, diols, and esters. Pure 1,6-hexanediol is obtained by fractional distillation of the crude reactor discharge. For the hydrogenation of dicarboxylic acids, catalysts containing cobalt, copper, or manganese are suitable. For the hydrogenation of esters, catalysts such as copper chromite or copper with added zinc and barium are used as "full catalysts" or on inert carriers. Ruthenium, platinum, or palladium on inert supports can also be used. Gas-phase hydrogenation of esters of adipic or 6-hydroxyhexanoic acid can be carried out at 1-7 MPa. Both acids and esters also may be hydrogenated using suspended catalysts. Oligomeric esters of the product diol and adipic acid can also be hydrogenated.

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 243, 1993 DOI: 10.1016/S0040-4039(00)60557-9

Hazard

Toxic by ingestion.

storage

Store at RT. 1,6-Hexanediol in the form of flflakes or as a solidifified melt is stored and shipped in barrels. It is transported as a melt in stainless steel containers, tank trucks, or tank cars.

Purification Methods

Fractionally crystallise it from its melt or from water. Distil it in vacuo. [Beilstein 1 IV 2556.]