17361-58-9

Basic information

• Product Name: 1,3-Dioxan-2-one, 4-methyl-
• CAS NO: 17361-58-9
• Molecular Formula: C5H8O3
• Molecular Weight: 116.117
• Mol File: 17361-58-9.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: 1,3-Dioxan-2-one, 4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dioxan-2-one, 4-methyl-(17361-58-9)
• EPA Substance Registry System: 1,3-Dioxan-2-one, 4-methyl-(17361-58-9)

Safety Data

• Hazardous Substances Data: 17361-58-9(Hazardous Substances Data)

Usage

General Description

1,3-Dioxan-2-one, 4-methyl-, also known as methyl glycolide, is a cyclic organic compound with the chemical formula C5H8O3. It is a colorless liquid with a mild, fruity odor and is used in various industrial applications such as in the production of polymers and as a solvent in chemical reactions. Methyl glycolide is also known for its potential as a monomer in the synthesis of biodegradable polymers, making it a valuable chemical in the field of sustainable materials. It is important to handle this chemical with caution as it may cause irritation to the skin, eyes, and respiratory system upon exposure.

Upstream product

• 18826-95-4 1.3-butanediol 
• 105-58-8 Diethyl carbonate 
• 1659-31-0 2,2'-dipyridyl carbonate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 50-00-0 formaldehyd 
• 187737-37-7 propene 
• 124-38-9 carbon dioxide 
• 616-38-6 carbonic acid dimethyl ester 
• 57-13-6 urea 
• 201230-82-2 carbon monoxide 
• 2167-39-7 (+/-)-2-methyloxetane 

Downstream Products

• 99855-05-7 6-methyl-3-phenyl-1,3-oxazinan-2-one 
• 67-63-0 isopropyl alcohol 
• 67-64-1 acetone 
• 98110-11-3 4,4,5,5,4',4',5',5'-octamethyl-2,2'-(1-methyl-propane-1,3-diyldioxy)-bis-[1,3,2]dioxaborolane 
• 67-56-1 methanol 
• 18826-95-4 1.3-butanediol 

Relevant articles and documents

A novel and efficient method for the catalytic direct oxidative carbonylation of 1,2- and 1,3-diols to 5-membered and 6-membered cyclic carbonates

In the presence of a PdI2-based catalytic system, 1,2-diols undergo an oxidative carbonylation process to afford 5-membered cyclic carbonates in good to excellent yields (84-94%) and with unprecedented catalytic efficiencies for this kind of reaction (up to ca. 190 mol of product per mol of PdI2). Under similar conditions, 6-membered cyclic carbonates are obtained for the first time through a direct catalytic oxidative carbonylation of 1,3-diols (66-74% yields).

A general and expedient synthesis of 5- and 6-membered cyclic carbonates by palladium-catalyzed oxidative carbonylation of 1,2- and 1,3-diols

We present a general, practical, and efficient approach to 5- and 6-membered organic carbonates by palladium-catalyzed direct oxidative carbonylation of 1,2- and 1,3-diols, respectively. Reactions were carried out at 100 °C in N,N-dimethylacetamide as the solvent under 20 atm (at 25 °C; 1 atm=101.3 kPa) of a 4:1 v/v CO/air mixture in the presence of 0.5-2 mol % of PdI2 and KI (KI/PdI2 molar ratio=10). Excess dehydrating agent, such as trimethyl orthoacetate, was necessary in several cases to obtain appreciable results. The method could also be applied to the synthesis of a high-value-added glycerol carbonate from glycerol, a readily available raw material. When applied to α-D-glucose, a double carbonylation process took place, with direct formation of α-D-glucofuranose 1,2:5,6-dicarbonate.

Highly synergistic effect of ionic liquids and Zn-based catalysts for synthesis of cyclic carbonates from urea and diols

The development of stable and efficient catalysts is an attractive topic for green chemistry reactions under mild reaction conditions. In order to improve solvent-free synthesis of cyclic carbonates from urea and diols, a binary catalyst systems of Zn-based and different ionic liquids (ILs) were developed and examined in this study. The yield of ethylene carbonate (EC) could reach to 92.2% in the presence of C16mimCl/ZnCl2 catalyst. Through exploring the structure-activity relationships of cation and anion, it was confirmed that a synergistic effect of cation and anion of catalyst had important influences on urea alcoholysis. Additionally, the controlling step of EC synthesis reaction involving the elimination of an ammonia molecule from intermediates had been revealed by in situ FT-IR. This could afford a guided insight for synthesizing cyclic carbonates with high yield. Furthermore, a possible mechanism for the catalytic process was proposed based on DFT and the experimental results via FT-IR, 1H-NMR and 13C NMR analysis, which revealed that not only a probable synergistic effects of cation-anion matters, but also C(2)-H of ILs and Zn2+ played a key role in accelerating the reaction of urea alcoholysis. This catalytic mechanism study is to provide a preliminary basis to develop novel catalysts for cyclic carbonates from urea and diols through a green synthetic pathway.

Chlorine-Free Synthesis of Organic Alkyl Carbonates and Five- and Six-Membered Cyclic Carbonates

This report presents a new, one-pot, facile, selective and green method for methoxycarbonylation of alcohols and synthesis of five- and six-membered cyclic carbonates from corresponding alcohols with dimethyl carbonate (DMC) in the presence of molecular sieves without any additional solvent and catalyst. Syntheses of bifunctional structures comprising a six-membered cyclic carbonate with allyl ether and methacrylate groups, respectively, for different polymerization modes, were also achieved and showed reproducibility on up-scaling the processes.