Tetrahydropyran-2-methanol

• CAS: 100-72-1
• Catalog Number: ACM100721
• Category: Main Products
• Molecular Weight: 116.16
• Molecular Formula: C₆H₁₂O₂
• Synonyms: 2H-Pyran-2-methanol, tetrahydro-;2-Hydroxymethyltetrahydropyrane;2-Methanol, tetrahydropyran;2-methanoltetrahydropyran;2-Methyloltetrahydro-1,4-pyran;2-Tetrahydropyranilcarbinol;Pyran-2-methanol, tetrahydro-;tetrahydro-2h-pyran-2-methano
• IUPAC Name: oxan-2-ylmethanol
• Canonical SMILES: C1CCOC(C1)CO
• InChI Key: ROTONRWJLXYJBD-UHFFFAOYSA-N
• Boiling Point: 187°C(lit.)
• Melting Point: 187°C
• Flash Point: 200°F
• Density: 1.027g/mL at 25°C(lit.)
• Appearance: clear, liquid
• EC Number: 202-882-4
• Exact Mass: 116.08400
• Hazard Statements: Xi
• Safety Description: 26-36-24/25
• Supplemental Hazard Statements: H227-H335-H315-H319
• Symbol: GHS07
• WGK Germany: 2

Case Study

Production of 1,6-Hexanediol from Tetrahydropyran-2-Methanol

Burt, Samuel P., et al. Green Chemistry, 2017, 19(5), 1390-1398.

Tetrahydropyran-2-methanol (THP2M), a biomass-derived feedstock, can be converted with high selectivity into 1,6-hexanediol (1,6-HDO), an important basic chemical. However, the high cost and low productivity of catalysts limit their industrial applicability. A three-step method is proposed for the synthesis of 1,6-HDO from THP2M via 2,3,4,5-tetrahydrooxepine (THO), avoiding the use of expensive catalysts.
Synthetic route from THP2M to 1,6-HDO
· In the first step, THP2M is dehydrated to 2,3,4,5-tetrahydrooxepine (THO) in a continuous flow, gas-phase reactor over a silicoaluminate catalyst. Various zeolite frameworks, as well as various alkali metals as exchange ions were tested in this dehydration reaction.
· In the second step, THO was hydrated to 2-oxepanol (OXL) and 6-hydroxyhexanal (6HDHX) in the absence of catalyst in an overall yield of 85%.
· Finally, 6HDHX and OXL (likely through 6HDHX) were then hydrogenated to 1,6-HDO with Ru/C or Ni/C nearly quantitatively.
· This pathway affords an overall yield of 34% to 1,6-HDO from THP2M, higher than previously reported 1,6-HDO yields from THP2M without using toxic metals.

Selective Hydrogenolysis of Tetrahydropyran-2-Methanol with Different Catalyst Carbon Supports

Karanjkar, Pranav U., et al. Catalysis Science & Technology, 2016, 6(21), 7841-7851.

Tetrahydropyran-2-methanol (THP2M) can undergo selective C-O-C hydrogenolysis under the action of a bifunctional RhRe catalyst to generate 1,6-hexanediol. The catalytic performance of bifunctional RhRe catalysts supported on two distinct carbon supports (NDC and VXC) towards THP2M was compared. The results show that the hydrogenolysis rate of the VXC-supported catalyst is two orders of magnitude higher than that of the NDC-supported catalyst.
Research on hydrogenolysis and catalyst activity of THP2M
· Continuous Flow Fixed Bed Reactor: Hydrogenolysis of THP-2M was conducted in a stainless-steel tubular flow reactor at elevated temperatures and pressure. Liquid products were analyzed by HPLC and GC, while gaseous products were analyzed using a gas chromatograph.
· Batch Reactor: Reactions using a 25 mL reaction mixture volume were performed in a 50 mL pressure vessel, and temporal concentration profiles over the course of reaction were obtained. Product mixtures were analyzed by HPLC and GC for quantitative analysis.

Custom Reviews

August 16, 2023

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Good oxidation resistance
In the experiment, the potential oxidation resistance of tetrahydropyran-2-methanol brought surprising results.

Custom Q&A

What is the refractive index of tetrahydropyran-2-methanol?

n20/D 1.458(lit.)

What is the vapor density of tetrahydropyran-2-methanol?

4.02

What is the acidity factor of tetrahydropyran-2-methanol?

14.48±0.10

What is the LogP of tetrahydropyran-2-methanol?

0.16

What's flash point of tetrahydropyran-2-methanol?

200 °F

What's boiling point of tetrahydropyran-2-methanol?

187 °C

What is the density of tetrahydropyran-2-methanol?

1.027 g/mL at 25 °C

What is the vapor pressure of tetrahydropyran-2-methanol?

0.4 mm Hg ( 20 °C)

What is the form of tetrahydropyran-2-methanol?

Colourless Oil

What chemical reactions can tetrahydropyran-2-methanol participate in?

Tetrahydropyran-2-methanol can participate in many typical organic reactions, including esterification, alcohol etherification, and nucleophilic substitution.