1,2,6-Hexanetriol

1,2,6-Hexantriol Strukturformel.svg 200px Hexane-1,2,6-triol correct FDA W45XXM0XWE 106-69-4 correct CAS 3184716 7535 203-424-6 C20334 7823 C(CCO)CC(CO)O 1S/C6H14O3/c7-4-2-1-3-6(9)5-8/h6-9H,1-5H2 ZWVMLYRJXORSEP-UHFFFAOYSA-N 6 14 3 1,2,6-Hexanetriol is a trivalent alcohol with two primary and one secondary hydroxy group. It is similar to glycerol in many respects and is used as a substitute for glycerol in many applications due to its more advantageous properties, such as higher thermal stability and lower hygroscopicity. Production Racemic 1,2,6-hexanetriol is obtained by catalytic hydrogenation of 2-hydroxyadipaldehyde (2-hydroxyhexane-1,6-dial)D.Arntz A. Fischer M. Höpp S. Jacobi J. Sauer T. Ohara T. Sato N. Shimizu H. Schwind Ullmann's Encyclopedia of Industrial Chemistry Acrolein and Methacrolein Wiley-VCH 2007 10.1002/14356007.a01_149.pub2 which is in turn produced by the acid hydrolysis of acrolein dimer (3,4-dihydro-2-formyl-2H-pyran) in dilute aqueous solution.H. Schulz H. Wagner Angew. Chem. Synthese und Umwandlungsprodukte des Acroleins 62 5 105–118 1950 German 10.1002/ange.19500620502 US 2768213 1,2,6-Hexanetriol 1956-10-23 R. Whetstone, S.A. Ballard Shell Development Co. 1,2,6-Hexantriol aus Acroleindimer Despite high product yields, a lightly colored product is obtained on this direct route and the hydrogenation catalyst is rapidly poisoned under the high aldehyde concentrations. For industrial production, it is therefore suitable to carry out the reaction in acidic alcoholic solutions, US 3773842 Process for the preparation of 1,2,6-hexanetriol 1973-11-20 J.-P. Schirmann, F. Weiss Ugine Kuhlmann whereby the solvent alcohol quickly adds to the activated double bond to form 2-formyl-6-alkoxytetrahydropyran (THP) and then reacts with the formyl group to form the corresponding hemiacetal. Water is added to the reaction mixture to hydrolyse the acetal groups and Raney nickel is added as a hydrogenation catalyst. The hydrogenation under 20 atm hydrogen at 140 °C is completed after approx. 1.5 h and, after work-up, yields pure 1,2,6-hexanetriol in a yield >95 %. 600px|1,2,6-Hexantriol über Hemiacetal Recently, several authors have described the synthesis of 1,2,6-hexanetriol from the easily accessible platform chemical hydroxymethylfurfural (HMF), which can be produced from "carbon neutral" (i.e. renewable) raw materials such as pentoses, hexoses, and other carbohydrates. WO 2011149339 Preparation of caprolactone, caprolactam, 2,5-tetrahydrofuran-dimethanol, 1,6-hexanediol or 1,2,6-hexanetriol from 2-hydroxymethyl-5-furfuralaldehyde 2011-03-23 J.G. De Vries, T. Bundara, P. Huat Phua, I.V. Melian Cabrera Netherlands Organisation for Scientific ResearchS. Yao X. Wang Y. Jiang F. Wu X. Chen X. Mu ACS Sustain. Chem. Eng. One-Step Conversion of Biomass-Derived 5-Hydroxymethylfurfural to 1,2,6-Hexanetriol Over Ni–Co–Al Mixed Oxide Catalysts Under Mild Conditions 2 173–180 2014 2 10.1021/sc4003714 In the first hydrogenation step from HMF to tetrahydrofuran-dimethanol, Raney nickel again shows the highest catalyst activity. Further hydrogenation, even with expensive rhodium-rhenium catalysts, leads only to modest selectivities and unsatisfactory yields. 1,2,6-Hexantriol aus HMF Properties 1,2,6-Hexanetriol is a clear, odourless, viscous, high-boiling and hygroscopic liquid, which is miscible with water and polar organic solvents but immiscible with non-polar solvents such as benzene, diethyl ether or heptane.Datenblatt 1,2,6-Hexanetriol, 97+%, extra pure bei Acros, retrieved 28 October 2014. The compound is similar in its properties to the simplest triol glycerol, but it is much more viscous at lower density and only about half as hygroscopic as glycerol. Because of its lower polarity and higher molecular volume, 1,2,6-hexanetriol often forms more stable mixtures or emulsions, especially with non-polar components, and is therefore also a useful plasticizer.Sigma-Aldrich : Technical Bulletin AL-128, 1,2,6-Hexanetriol, Use 1,2,6-Hexanetriol is used as a solvent, for raising the viscosity of liquid and semi-solid cosmeticSAA Pedia: 1,2,6-Hexanetriol and pharmaceutical preparations due to its low toxicity and good compatibility, and as a humectant due to its hygroscopicity. 1,2,6-hexanetriol improves the effectiveness of the active ingredients as an adjuvant in crop protection formulations. In inks and paints it stabilizes the dispersion of pigments. Derivatives of 1,2,6-hexanetriol are also used in hydraulic fluids and as corrosion inhibitors. US 3403104 Borate corrosion inhibitors 1968-9-24 P.B. Sullivan Union Carbide Corp. As a trifunctional molecule, 1,2,6-hexanetriol acts as a polyol in polyurethanes and as a crosslinker in polyesters and alkyd resins.R.W. Tess R.D. Harline T.F. Mika Ind. Eng. Chem. 1,2,6-Hexanetriol in Alkyd Resins 49 3 374–378 1957 10.1021/ie51392a028 Esters of 1,2,6-hexanetriol with longer-chain carboxylic acids are useful plasticizers for PVC and cellulose acetate, as well as for rubber polymers such as nitrile rubber (NBR) and neoprene., 1,2,6-hexanetriol is used as a monomer for the synthesis of POE III type polyorthoesters, which are characterized by an ointment-like consistency due to the high flexibility of the triol and have been tested as active ingredient depot materials for ophthalmic applications.Jorge Heller A.J. Domb J. Kost D.M. Wiseman Handbook of Biodegradable Polymers 6. Poly (Ortho Esters) Harwood Academic Press 99–118 90-5702-153-6 1997 References Category:Triols Category:Hexanols Category:Vicinal diols Category:Primary alcohols Category:Secondary alcohols