38802-97-0

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
5-Ethyl-5-(hydroxymethyl)-1,3-dioxan-2-one is used as a key intermediate in the synthesis of a range of pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides.
Used as a Protecting Group in Organic Chemistry:
In the realm of organic chemistry, 5-Ethyl-5-(hydroxymethyl)-1,3-dioxan-2-one serves as an effective protecting group for aldehydes and ketones, facilitating complex organic synthesis processes by preventing unwanted side reactions.
Used in Perfumery and Fragrance Production:
Leveraging its agreeable scent, 5-Ethyl-5-(hydroxymethyl)-1,3-dioxan-2-one is utilized in the production of perfumes and fragrances, enhancing the olfactory profiles of various consumer products.
Used in Chemical Reactions:
Due to its high reactivity, 5-Ethyl-5-(hydroxymethyl)-1,3-dioxan-2-one is employed in a variety of chemical reactions including hydrolysis, esterification, and reduction, broadening its applications across different industries.
Used in Chemical Research:
5-Ethyl-5-(hydroxymethyl)-1,3-dioxan-2-one is also used in chemical research for studying reaction mechanisms and exploring new synthetic pathways, contributing to the advancement of chemical science.

Upstream product

• 77-99-6 1,1,1-tri(hydroxymethyl)propane 
• 105-58-8 Diethyl carbonate 
• 77-85-0 2-(hydroxymethyl)-2-methylpropane-1,3-diol 
• 616-38-6 carbonic acid dimethyl ester 
• 102-09-0 bis(phenyl) carbonate 

Relevant academic research and scientific papers

URETHANES, POLYMERS THEREOF, COATING COMPOSITIONS AND THEIR PRODUCTION FROM CYCLIC CARBONATES

The present invention relates to functionalized cyclic carbonates, urethanes and polyurethanes, their methods of production and uses thereof.

METHOD FOR PRODUCING CYCLIC CARBONATES

Linear or cyclic carbonates as potential monomers for isocyanate-free polyurethanes and polycarbonates were prepared from polyols and dialkylcarbonatesor diphenyl carbonates. This invention was developed to produce linear or cyclic carbonates with or without using catalysts. Polyol compounds were reacted with carbonates such as dimethylcarbonate and diethylcarbonate to produce thecorresponding linear and/or cyclic carbonate.

SOLVENT-FREE SYNTHESIS OF CYCLIC CARBONATES

Disclosed is a process for production of a cycloaliphatic carbonate from a diol, triol or polyol and a carbon dioxide source, such as a dialkyl carbonate. Said process is performed in a solvent-free medium using a N-heterocyclic carbene or N-heterocyclic carbene complex as catalyst. Said N-heterocyclic carbene or carbene complex is preferably attached to a lipase. Said process comprises preferably a transesterification step and a thermal disproportionation step and yielded cycloaliphatic carbonate is in preferred embodiments a monocyclic carbonate having a five-membered or a six-membered ring.

Lipase-mediated synthesis of six-membered cyclic carbonates from trimethylolpropane and dialkyl carbonates: Influence of medium engineering on reaction selectivity

Six-membered cyclic carbonates are potential monomers for aliphatic polycarbonates and polyurethanes in a process without using toxic phosgene and isocyanate. Lipase catalyzed transesterification of the polyol, trimethylolpropane (TMP) with dimethyl carbonate (DMC) or diethyl carbonate (DEC) followed by thermal cyclization was used for synthesis of six-membered cyclic carbonates with pendant hydroxyl and alkoxycarbonyloxyl groups. Immobilized lipase B from Candida antarctica (Novozym435) was used as the catalyst. Mixture of a hydrophilic solvent such as THF for high solubility of TMP, and a hydrophobic solvent such as toluene, were selected as the best solvent system for achieving high substrate conversion and selectivity. A relationship between polyol conversion and solvent hydrophobicity (log P) and solvent type, respectively, was established. THF:toluene system at a ratio of 0.5:1.0 (v/v) provided high degree of TMP conversion to product with high proportion of cyclic carbonates (>80%). The cyclic carbonate with pendant hydroxyl group was obtained with almost 85% selectivity at TMP conversion of 68.6% using 10% (w/w) Novozym435 at TMP:DMC ratio of 1:1. However, at TMP:DMC ratio of 1:5 and the same biocatalyst concentration, the TMP conversion was 100% with 72% selectivity for the cyclic carbonate with pendant alkoxycarbonyloxyl group. The product formed was without or with less content of linear carbonates, bis and tris(methoxycarbonyloxy)-TMP, as compared to that in a solvent-free system. The reactivity of DEC was lower than that of DMC. The reaction pathway leading to the formation of cyclic carbonate in this process comprised enzymatic carbonation of TMP with alkylcarbonates and thermal cyclization of linear carbonates. The process affords high degree of conversion of polyol to cyclic carbonates and provides a potentially attractive synthetic route for monomers of polycarbonates and polyurethanes.

Solvent-free lipase-mediated synthesis of six-membered cyclic carbonates from trimethylolpropane and dialkyl carbonates

Six-membered cyclic carbonates with hydroxyl and/or alkoxycarbonyloxy groups, as potential monomers for polyurethanes and polycarbonates, were prepared by the reaction between trimethylolpropane (TMP) with dimethyl carbonate (DMC) or diethylcarbonate (DEC) mediated by immobilized Candida antarctica lipase B, Novozym 435 in a solvent-free medium. The dialkyl carbonate served as a solvent for the reaction. The solubility of TMP at 50°C was 565 mg mL-1 in DMC, and 64.8 mg mL-1 in DEC. Reactions using biocatalyst concentrations of 10, 20 and 40% (w/w of TMP) showed similar profiles, with a linear increase in the conversion of TMP to 90% within 24 h, and complete conversion within 48 h. At biocatalyst concentrations of 2.5 and 5% (w/w of TMP), the main products were mono-carbonated TMP (3) and/or cyclic carbonate (4), while di and tri-carbonated TMP (5, 7) were obtained at lipase concentrations of 20 and 40%. The reactivity of DEC was lower than that of DMC, but led to higher selectivity in production of 3 or 4. A large fraction of the linear carbonates in the product mixture were cyclized by disproportionation involving heating at 60-80°C without any catalyst. The total yield of cyclic carbonates was about 85% after thermal treatment at 80°C. This process, consisting of lipase-catalyzed transesterification and thermal disproportionation, provides a novel and more environmentally friendly approach for the synthesis of cyclic carbonates without using toxic organic solvents, phosgene or isocyanate. The Royal Society of Chemistry.

Fast monomers: Factors affecting the inherent reactivity of acrylate monomers in photoinitiated acrylate polymerization

A systematic study on the effect of molecular structure on the photoinitiated polymerization of acrylates was undertaken. Initially, the research was focused on the effect of hydrogen bonding, and it was found that preorganization via hydrogen bonding enhances the maximum rate of polymerization (Rp). This hydrogen bonding facilitated preorganization also affected the tacticity of the resultant polymer. Next, the effect of polarity as represented by the calculated dipole moment (μcalc) of a given monomer was investigated. A direct linear correlation between Rp and the calculated Boltzmann-averaged dipole moment (μcalc) was observed. The Rp-μcalc correlation holds for pure monomers, mixtures of monomers, and even mixtures of monomers with inert solvents. This correlation enables the rational design of monomers with a required reactivity. In addition, these studies suggest that the propagation step of polymerization is influenced by hydrogen bonding while the dipole moment influences the termination rate constant. These two mechanistic explanations can be regarded as complementary factors that influence the speed of acrylate polymerization.