629-11-8 Usage
Description
1,6-Hexanediol is a white, waxy, hygroscopic solid compound that is a linear diol with two primary hydroxyl groups located at the terminal positions. Its linear hydrocarbon chain contributes to the enhanced hardness and flexibility of polyesters, making it a valuable component in various industries.
Uses
1. Used in Polymer Synthesis:
1,6-Hexanediol is used as an intermediate in the production of polyester, polyurethane, and nylon. It plays a crucial role in the synthesis of these materials, providing the necessary structural properties for their applications.
2. Used in Adhesives, Acrylics, and Dyestuffs:
As an intermediate, 1,6-Hexanediol is also utilized in the production of adhesives, acrylics, and dyestuffs, where its chemical properties contribute to the desired characteristics of these products.
3. Used in Gasoline Refining:
1,6-Hexanediol is employed in the gasoline refining process, where it serves as a valuable component in improving the quality and performance of the final product.
4. Used in Pharmaceutical Production:
1,6-Hexanediol is also used in the pharmaceutical industry, where its unique properties can be harnessed for various applications.
5. Used in Chemical Industry as a Solvent and Intermediate for High Polymers:
1,6-Hexanediol serves as a solvent and intermediate for high polymers such as nylon and polyesters, contributing to the development of these materials.
6. Used as a Coupling Agent and in Coil Coating:
1,6-Hexanediol is also used as a coupling agent and in coil coating applications, where its properties enhance the performance and durability of the final product.
7. Used in the Synthesis of ZSM-5 Zeolite:
1,6-Hexanediol acts as a structure-directing agent for the synthesis of ZSM-5 zeolite, a material with various industrial applications.
8. Used as a Solvent for Titanium Tetraisopropoxide:
1,6-Hexanediol is used as a solvent for titanium tetraisopropoxide to form titanium oxide (TiO2) nanocrystals, which have applications in various industries, including electronics and solar energy.
9. Used as a Phase Change Material:
1,6-Hexanediol can be used in combination with lauric acid as a phase change material for thermal energy storage applications, where it helps store and release thermal energy efficiently.
Preparation
1,6-Hexanediol is produced by a propriety process that is based on BASF technology. Industrially, it is prepared by the hydrogenation of adipic acid. Conversely, in the laboratory, 1,6-Hexanediol can be synthesized by the reduction of adipic acid with lithium aluminum hydride.
Uses and Applications
Polyurethanes
1,6-Hexanediol is widely utilized in the manufacture of polyesterols such as sebacates, azelates, and adipates. These compounds are resistant to hydrolysis and have low glass transition temperature as well as high mechanical levels. 1,6-hexanediol is used as an ingredient in the preparation of a wide range of tailor-made products for numerous specialty and standard applications.
In Acrylics
1,6-hexanediol is utilized as an ingredient in the manufacture of the bifunctional hexanediol diacrylate which is a monomer that is normally used in conjunction with other acrylic monomers as a reactive diluent for decorative coatings and printing inks.
In Adhesives
Urethanes and co-terephthalates that are based on 1,6-hexanediol provide faster better tack properties and crystallization. Due to its low glass transition property, 1,6-hexanediol offers high flexibility as well as excellent adhesive properties.
Other Uses
1,6-hexanediol is incorporated into the production of other compounds used in polymeric thickeners, sizing agents, plasticizers for polyvinyl chloride, pesticides, and surfactants dyestuffs as a flexible building block.
Safety
1,6-hexanediol is a no-irritating to the skin. However, it can be irritative to the respiratory tract and mucous membrane. 1,6-hexanediol vapours or dust cause irritation to the eye. Severe eye exposure may cause conjunctivitis, iritis, and diffuse corneal opacity.
Synthesis Reference(s)
Tetrahedron Letters, 34, p. 243, 1993 DOI: 10.1016/S0040-4039(00)60557-9
Hazard
Toxic by ingestion.
Purification Methods
Fractionally crystallise it from its melt or from water. Distil it in vacuo. [Beilstein 1 IV 2556.]
Check Digit Verification of cas no
The CAS Registry Mumber 629-11-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 9 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 629-11:
(5*6)+(4*2)+(3*9)+(2*1)+(1*1)=68
68 % 10 = 8
So 629-11-8 is a valid CAS Registry Number.
629-11-8Relevant articles and documents
Determining Roles of Cu0 in the Chemosynthesis of Diols via Condensed Diester Hydrogenation on Cu/SiO2 Catalyst
Wang, Weichao,Wang, Hui,Zhang, Jingwei,Kong, Lingxin,Huang, Huijiang,Liu, Wei,Wang, Shengping,Ma, Xinbin,Zhao, Yujun
, p. 3849 - 3852 (2020)
Copper-based catalyst was applied in the condensed diester hydrogenation with unexpected high selectivity (~100 percent) to 1,6-hexanediol. On basis of the mass transfer analysis and kinetics results, the reaction rate of the condensed diester hydrogenation was deduced to be controlled by the activation of hydrogen on Cu0 sites, which was further demonstrated by the correlations between the catalytic activity and different copper species. Importantly, this catalysis mechanism is different with that of gas-phase diester hydrogenation, which is generally determined by the adsorption of ester on Cu+ species.
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Raphael,Roxburgh
, p. 3875 (1952)
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Synthesis of Supported RhMo and PtMo Bimetallic Catalysts by Controlled Surface Reactions
Alba-Rubio, Ana C.,Sener, Canan,Hakim, Sikander H.,Gostanian, Thomas M.,Dumesic, James A.
, p. 3881 - 3886 (2015)
We previously described a synthesis method to prepare bimetallic catalysts with narrow nanoparticle size and composition distributions by means of controlled surface reactions (CSR) between a reduced supported metal nanoparticle and an organometallic precursor of an oxophilic promoter metal. Herein, we report a comparison of such catalysts with those prepared by traditional incipient wetness impregnation. STEM/EDS analysis indicates that catalysts prepared by CSR exhibit more effective interaction of metals, thereby minimizing the undesirable formation of component-rich nanoparticles and/or monometallic domains. Reaction kinetics studies using these bimetallic catalysts reveal that optimal conversion rates in a selective CO hydrogenolysis reaction (i.e., hydrogenolysis of 2-(hydroxymethyl)tetrahydropyran to 1,6-hexanediol) could be achieved using a lower amount of the oxophilic promoter metal for the catalysts prepared by the CSR approach, as compared to their impregnated counterparts. A superior method for greater results: At the same conversion rate level, catalysts prepared by controlled surface reactions (CSR) requires smaller amount of promoter as compared to those prepared by incipient wetness impregnation (IWI). This increased performance is attributed to the uniform bimetallic composition of the catalysts prepared by CSR.
Reductive depolymerization of polyesters and polycarbonates with hydroboranes by using a lanthanum(iii) tris(amide) catalyst
Berthet, Jean-Claude,Cantat, Thibault,Kobylarski, Marie
supporting information, p. 2830 - 2833 (2022/03/09)
The homogeneous reductive depolymerization of polyesters and polycarbonates with hydroboranes is achieved with the use of an f-metal complex catalyst. These polymeric materials are transformed into their value-added alcohol equivalents. Catalysis proceeds readily, under mild conditions, with La[N(SiMe3)2]3 (1 mol%) and pinacolborane (HBpin) and shows high selectivity towards alcohols and diols, after hydrolysis.
Interworking ligand, hydroformylation catalyst and preparation method of dihydric alcohol
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Paragraph 0071; 0079-0080, (2021/07/09)
The invention discloses an interworking ligand, a hydroformylation catalyst and a preparation method of dihydric alcohol. The interworking ligand comprises a ligand unit I and a ligand unit II, has the characteristics of a bidentate phosphine ligand, and is high in catalytic activity and good in stability; and when the catalyst is used for preparing dihydric alcohol from olefin, linear alcohol can be obtained through a one-step method, and the content of by-products in a traditional series process is reduced. The method has the advantages of simple and convenient process, low cost and energy consumption, good production safety, high product quality and the like, and is particularly suitable for large-scale industrial production.