6581-64-2

Usage

Uses

Used in Food and Beverage Industry:
2H-Pyran, tetrahydro-2-propoxyis used as a flavoring agent for its ability to impart a fruity aroma and taste to various food and beverage products, enhancing their sensory appeal and consumer experience.
Used in Fragrance Production:
In the fragrance industry, 2H-Pyran, tetrahydro-2-propoxyis utilized as a key component in creating complex and pleasant scents. Its fruity odor contributes to the development of unique and attractive fragrances for personal care and household products.
Used in Industrial Applications as a Solvent:
2H-Pyran, tetrahydro-2-propoxyserves as a solvent in various industrial processes, where its properties allow for effective dissolution and interaction with other chemicals, facilitating reactions and processes in different manufacturing sectors.

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 71-23-8 propan-1-ol 
• 6089-04-9 3-(tetrahydropyran-2'-yloxy)propyne 
• 33821-94-2 3-(tetrahydro-2H-pyran-2-yloxy)propyl bromide 
• 13464-19-2 phenyl chlorothioformate 
• 52103-12-5 3-iodopropyl tetrahydro-2H-pyran-2-yl ether 
• 69161-61-1 2-(prop-2-en-1-yloxy)oxane 

Downstream Products

• 33821-94-2 3-(tetrahydro-2H-pyran-2-yloxy)propyl bromide 
• 1912-31-8 propyl methanesulfonate 

Relevant academic research and scientific papers

Breaking Structural Energy Constraints: Hydrothermal Crystallization of High-Silica Germanosilicates by a Building-Unit Self-Growth Approach

Zeolites, a class of crystalline microporous materials, have a wide range of practical applications, in particular serving as key catalysts in petrochemical and fine-chemical processes. Millions of zeolite topologies are theoretically possible. However, to date, only 235 frameworks with various tetrahedral element compositions have been discovered in nature or artificially synthesized, among which approximately 50 topologies are available in pure-silica forms. Germanosilicates are becoming an important zeolite family, with a rapidly increasing number of topological structures having unusual double four-membered ring (D4R) building units and large-pore or extra-large-pore systems. The synthesis of their high-silica analogues with higher (hydro)thermal stability remains a great challenge, because the formation of siliceous D4R units is kinetically and thermodynamically unfavorable in hydrothermal systems. Herein, it is demonstrated that such D4R-containing high-silica zeolites with unexpected crystalline topologies (ECNU-24-RC and IM-20-RC) are readily constructed by a versatile route. This strategy provides new opportunities for the synthesis of high-silica zeolite catalysts that are hardly obtainable by conventional hydrothermal synthesis and may also facilitate a breakthrough in increasing the number and types of zeolite materials with practical applications.

Post-synthesis incorporation of Al into germanosilicate ITH zeolites: The influence of treatment conditions on the acidic properties and catalytic behavior in tetrahydropyranylation

Post-synthesis alumination of germanosilicate medium-pore ITH zeolites was shown to be an effective procedure for tuning their acidity. Treatment of ITH zeolites synthesized with different chemical compositions (i.e. Si/Ge = 2.5, 4.4 and 5.8) with aqueous Al(NO3)3 solution led to the formation of strong Br?nsted and Lewis acid sites and an increasing fraction of ultramicro- and meso-pores in Ge-rich ITH samples (Si/Ge = 2.5 and 4.4). The concentration of Al incorporated into the framework increases with decreasing Si/Ge ratio of the parent ITH. The increasing temperature of alumination from 80 to 175 °C (HT conditions) resulted in (1) a 1.5-2-fold increase in the concentration of Br?nsted acid sites formed and (2) a decreasing fraction of framework Al atoms detectable with base probe molecules (i.e. pyridine, 2,6-di-tert-butylpyridine), i.e. an increased concentration of the "inner" acid sites. The activity of prepared Al-substituted ITH zeolites in tetrahydropyranylation of alcohols is enhanced with increasing amount of accessible acid sites in bulky crystals (e.g. alumination at lower temperature) or with increasing total concentration of acid centres within tiny ITH crystals (e.g. alumination under HT conditions). This trend became more prominent with increasing kinetic diameter of the substrate molecules under investigation (methanol 1-propanol 1-hexanol).

3,5-Dinitrobenzoic acid catalyzed synthesis of 2,3-unsaturated O- and S-glycosides and tetrahydropyranylation of alcohols and phenols

A simple procedure for the synthesis of 2,3-unsaturated glycosides in acetonitrile and tetrahydropyranylation of alcohols and phenols in dichloromethane in the presence of 3,5-dinitrobenzoic acid is described. A variety of alcohols and thiols are reacted with glycals to give the desired products in high yields with high α-selectivity.

Tetrahydropyranylation of alcohols and phenols using polystyrene supported lewis acids as catalysts

Polystyrene supported TiCl4 (Ps-TiCl4) and polystyrene supported FeCl3(Ps-FeCl3) were prepared by coordinating Lewis acids with polystyrene. The catalysts were characterized by TGA, BET, SEM, IR and pyridine-adsorbed IR. The loading of Ps-TiCl4 and Ps-FeCl3 were 0.35 and 0.3 mmol·g-1 respectively. Both catalysts were found to be efficient for the tetrahydropyranylation and detetrahydropyranylation of various alcohols and phenols in different solvents. Two catalysts can be recovered and reused for five times with good activity. Polystyrene supported TiCl4 (Ps-TiCl4) and polystyrene supported FeCl3(Ps-FeCl 3) were prepared by coordinating Lewis acids with polystyrene. The catalysts were characterized by TGA, BET, SEM, IR and pyridine-adsorbed IR. The loading of Ps-TiCl4 and Ps-FeCl3 were 0.35 and 0.3 mmol·g-1 respectively. Both catalysts were found to be efficient for the tetrahydropyranylation and detetrahydropyranylation of various alcohols and phenols in different solvents. Two catalysts can be recovered and reused for five times with good activity. Copyright

Solvent-free tetrahydropyranylation of alcohols catalyzed by amine methanesulfonates

A comparative study of tetrahydropyranylation of alcohols under various solvents or solvent-free conditions using different amine methanesulfonates as catalysts shows that tetrahydropyranyl ethers of alcohols are obtained under solvent-free conditions in good yields using catalytic amounts of triethylenediamine methanesulfonate, 1,6-hexanediamine methanesulfonate, diethylenetriamine methanesulfonate and pyridine methanesulfonate, respectively. The reaction occurs readily in short times at room temperature catalyzed by these catalysts, especially triethylenediamine methanesulfonate. Some of the major advantages of this procedure are that the catalysts are environmentally friendly, highly effective, and easy to prepare and handle. The reaction is also clean and needs no solvent, and the work-up is very simple.

Pd-MCM-48: A novel recyclable heterogeneous catalyst for chemo- and regioselective hydrogenation of olefins and coupling reactions

A novel, heterogeneous Pd-MCM-48 catalyst has been developed by encapsulating palladium nanoparticles into the cubic phase of mesoporous MCM-48 matrix at room temperature. The catalyst demonstrated excellent chemo- and regioselectivity for the hydrogenation of olefins at room temperature within 30-80 min. The turnover frequency for the hydrogenation is very high (4400 h-1). Interestingly, selectivity of the catalyst was significantly influenced by the mode of addition of palladium precursor. Moreover, the catalyst was also very effective for the coupling reactions with the formation of carbon-carbon and carbon-nitrogen bonds under ligand-free and aerobic conditions.

Metal benzenesulfonates/acetic acid mixtures as novel catalytic systems: Application to the protection of a hydroxyl group

A surprising synergistic effect has been discovered in mixtures of metal benzenesulfonates (Co, Al, Ni, Zn, Cd, Pr, La, Cu, Mn) and acetic acid, leading to active catalytic systems for the tetrahydropyranylation of alcohols and phenols to produce tetrahydropyranyl ethers. All reactions proceed mildly and efficiently with moderate to high yields at room temperature without solvent. After the reaction, the metal benzenesulfonate can be easily recovered and reused many times. The efficiency of these systems might result from the "double activation" by Bronsted and Lewis acid catalysis.

1,6-Hexanediamine methanesulfonate: A mild and efficient catalyst for the tetrahydropyranylation of alcohols under solvent-free conditions

Various alcohols react with 3,4-dihydro-2 H-pyran under mild conditions using a catalytic amount of 1,6-hexanediamine methanesulfonate. It affords the corresponding tetrahydropyranyl ethers in good yields at a faster rate in the absence of solvent. Taylor & Francis Group, LLC.

Copper nitrate/acetic acid as an efficient synergistic catalytic system for the chemoselective tetrahydropyranylation of alcohols and phenols

Tetrahydropyranylation of alcohols and phenols was accomplished successfully using copper nitrate and acetic acid as a synergistic catalyst at room temperature under solvent-free condition. Compared with other synergistic catalytic systems, copper nitrate/acetic acid proved to be the most efficient. Both alcohols (primary, secondary, tertiary, benzylic, cyclic, allyl, cinnamyl, and furyl) and phenols reacted smoothly in high yields. Graphical abstract: [Figure not available: see fulltext.]

Copper p-toluenesulfonate/acetic acid: A recyclable synergistic catalytic system for the tetrahydropyranylation of alcohols and phenols

Copper p-toluenesulfonate/acetic acid was found to be an efficient, chemoselective synergistic catalytic system, with catalyst loading as low as 0.3 mol% leading to clean, high-yielding tetrahydropyranylation of a variety of alcohols and phenols. By simple phase-separation, copper p-toluenesulfonate can be easily recovered and reused for several times without deterioration in catalytic activity.