31852-84-3

Usage

Uses

Used in Biomedical Applications:
1,3-Dioxan-2-one is used as a key component in the production of biodegradable composites for bone tissue engineering and drug delivery. The resulting PTMC-based polymers degrade in vivo through an enzymatic surface erosion mechanism without releasing acidic degradation products, making them suitable for use in biomedical applications.
Used in Polymer Industry:
1,3-Dioxan-2-one is used as a monomer for the synthesis of amorphous polymers with low glass transition temperatures. These polymers can be copolymerized with other lactone monomers to create materials with tunable properties, such as flexibility and elasticity. After cross-linking, a (co-)polymer network is obtained with properties similar to those of polydimethylsiloxane (PDMS) rubber, making it useful for various applications in the polymer industry.

Production Methods

The direct polymerization method is a continuous esterification reactionOpen-loop polymerization includes three reaction steps: oligomerization, depolymerization and ring opening, which can achieve precise control of the polymerization reaction

InChI:InChI=1/C4H6O3/c5-4-6-2-1-3-7-4/h1-3H2

Upstream product

• 503-30-0 trimethylene oxide 
• 124-38-9 carbon dioxide 
• 76508-46-8 2-ethoxy-1,3-dioxane 
• 75-25-2 Bromoform 
• 105014-07-1 2,2-diphenoxy-1,3-dioxane 
• 95104-50-0 2,2-Dimethoxy-1,3-dioxan 
• 24424-99-5 di-tert-butyl dicarbonate 
• 504-63-2 trimethyleneglycol 
• 75-44-5 phosgene 
• 107-06-2 1,2-dichloro-ethane 
• 541-41-3 chloroformic acid ethyl ester 
• 201230-82-2 carbon monoxide 
• 82091-12-1 dimethyl 2,2’-(carbonylbis(oxy))dibenzoate 
• 57-13-6 urea 

Downstream Products

• 53953-47-2 3-(1H-benzimidazol-1-yl)propan-1-ol 
• 22159-27-9 3-(2-methyl-1H-imidazol-1-yl)propan-1-ol 
• 51390-23-9 1-(3-hydroxypropyl)imidazole 
• 97594-98-4 4,4,5,5,4',4',5',5'-octamethyl-2,2'-propane-1,3-diyldioxy-bis-[1,3,2]dioxaborolane 
• 1195-66-0 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 56535-86-5 3-phenyl-1,3-oxazinan-2-one 

Relevant academic research and scientific papers

PROCESS FOR THE SYNTHESIS OF ISOCYANATE-FREE OMEGA-HYDROXY-URETHANES, ALPHA-OMEGA-DIURETHANES AND OLIGO (POLY)URETHANES

The synthesis of omega-hydroxyalkyl-urethanes, and of alfa-omega-diurethanes is reported which includes the reaction of diols with urea in presence of catalysts based on Ce at temperatures between 125 and 170°C over 4-8 h reaction time. A process for the production of oligomers of omega-hydroxyalkyl-urethanes is also reported based on the reaction of urea with diols in presence of Ce or Zr catalysts or Ce mixed oxides at 125-170°C over 4-20 h.

Overcoming Barriers in Polycarbonate Synthesis: A Streamlined Approach for the Synthesis of Cyclic Carbonate Monomers

Accessing cyclic carbonate monomers on a large scale is critical for the development of any new carbonate-based materials platform. The synthesis of carbonate monomers can be a challenging and tedious endeavor requiring multiple synthetic steps and purifications. To address this, we report a drastically improved process for the synthesis of carbonate monomers via a two-step route that avoids the use of hazardous triphosgene or chloroformate reagents. This process enables rapid access to a broad array of functional groups on the carbonate monomer and the monomers generated from the procedure can readily be polymerized via ring-opening polymerization.

Ultrasound-assisted synthesis of a stable Co(II) coordination polymer as heterogeneous catalyst for CO2 transformation

A stable benzimidazole-containing Co(II) coordination polymer namely [Co(L)0.5(oba)]n (1) (H2oba = 4,4′-oxybis(benzoate), L = 1,6-bis(5,6-dimethylbenzimidazolyl) hexane) was successfully synthesized by ultrasonic technique under mild conditions. In especial, the effects of initial reagent concentration, irradiation time and ultrasonic power on the morphology and size of micron scale 1 were discussed in detail. Micron scale 1 appeared exceptional solvent and pH stabilities. Further, as a heterogeneous Lewis catalyst, 1 exhibited a highly activity and recyclability for CO2 transformation by cycloaddition with epoxide under room temperature.

Rational Design of Cobalt Complexes Based on the trans Effect of Hybrid Ligands and Evaluation of their Catalytic Activity in the Cycloaddition of Carbon Dioxide with Epoxide

A series of cobalt complexes are presented as effective catalysts for the synthesis of cyclic carbonates from epoxides and CO2. The catalytic potentials of the cobalt complexes, in combination with tetrabutylammonium bromide, have been demonstrated to solve some challenges in the synthesis of cyclic carbonates, including the room-temperature conversion of terminal epoxides and activation-challenging substrates such as internal epoxides and fatty acid derived epoxides. A key factor in the success of the strategy is the use of cobalt complexes that are prepared on the basis of the trans effect of hybrid ligands. The trans effect between N-heterocyclic carbenes and acetylacetone has been proved by a number of spectroscopic measurements, including UV-vis, ESI-MS, EPR, and in situ FT-IR and by DFT calculations; these support the notion that acetylacetone prefers to dissociate from the cobalt center, which will result in one coordination site for the activation of a substrate molecule at the cobalt atom and thus give rise to high reactivity.

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.

Supported Polyhedral Oligomeric Silsesquioxane-Based (POSS) Materials as Highly Active Organocatalysts for the Conversion of CO2

Very high turnover numbers (TON) and productivity values up to 7875 and 740 respectively have been obtained for the conversion of CO2 into cyclic carbonates by using hybrid materials based on imidazolium modified polyhedral oligomeric silsesquioxanes (POSS-Imi) grafted on amorphous silica (SiO2) and mesostructured SBA-15. The heterogeneous organocatalysts were easily prepared via a straightforward synthetic procedure allowing to generate high local concentration spots of imidazolium active sites surrounding the POSS core. This synthetic procedure is also a promising approach for the design of a wide library of hybrid functional materials. The materials do not possess other co-catalytic species with Lewis or Br?nsted acid functionalities which still represents a challenging aspect for the outcome of the process. The recyclability of the catalysts was successfully verified for four consecutive runs. The catalytic versatility was proved with a wide range of epoxides and with the most challenging oxetane on large scale (105–210 mmol) showing higher performances in comparison with other unmodified imidazolium-based catalytic systems. The new hybrids based on supported POSS nanostructures allowed the sustainable conversion of carbon dioxide under solvents- and metal-free reaction conditions with a full selectivity toward cyclic carbonates.

Visible-Light-Mediated Liberation and In Situ Conversion of Fluorophosgene

The first example for the photocatalytic generation of a highly electrophilic intermediate that is not based on radical reactivity is reported. The single-electron reduction of bench-stable and commercially available 4-(trifluoromethoxy)benzonitrile by an organic photosensitizer leads to its fragmentation into fluorophosgene and benzonitrile. The in situ generated fluorophosgene was used for the preparation of carbonates, carbamates, and urea derivatives in moderate to excellent yields via an intramolecular cyclization reaction. Transient spectroscopic investigations suggest the formation of a catalyst charge-transfer complex-dimer as the catalytic active species. Fluorophosgene as a highly reactive intermediate, was indirectly detected via its next downstream carbonyl fluoride intermediate by NMR. Furthermore, detailed NMR analyses provided a comprehensive reaction mechanism including a water dependent off-cycle equilibrium.

Metal free synthesis of ethylene and propylene carbonate from alkylene halohydrin and CO2 at room temperature

Herein we describe a metal free and one-pot pathway for the synthesis of industrially important cyclic carbonates such as ethylene carbonate (EC) and propylene carbonates (PC) from molecular CO2 under mild reaction conditions. In the actual synthesis, the alkylene halohydrins such as alkylene chloro- or bromo or iodohydrin and organic superbase, 1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) reacted equivalently with CO2 at room temperature. The syntheses of cyclic carbonates were performed in DMSO as a solvent. Both 1,2 and 1,3 halohydrin precursors were converted into cyclic carbonates except 2-bromo- and iodoethanol, which were reacted equivalently with DBU through n-alkylation and formed corresponding n-alkylated DBU salts instead of forming cyclic carbonates. NMR analysis was used to identify the reaction components in the reaction mixture whereas this technique was also helpful in terms of understanding the reaction mechanism of cyclic carbonate formation. The mechanistic study based on the NMR analysis studies confirmed that prior to the formation of cyclic carbonate, a switchable ionic liquid (SIL) formed in situ from alkylene chlorohydrin, DBU and CO2. As a representative study, the synthesis of cyclic carbonates from 1,2 chlorohydrins was demonstrated where the synthesis was carried out using chlorohydrin as a solvent as well as a reagent. In this case, alkylene chlorohydrin as a solvent not only replaced DMSO in the synthesis but also facilitated an efficient separation of the reaction components from the reaction mixture. The EC or PC, [DBUH][Cl] as well as an excess of the alkylene chlorhydrin were separated from each other following solvent extraction and distillation approaches. In this process, with the applied reaction conditions, >90% yields of EC and PC were achieved. Meanwhile, DBU was recovered from in situ formed [DBUH][Cl] by using NaCl saturated alkaline solution. Most importantly here, we developed a metal free, industrially feasible CO2 capture and utilization approach to obtain EC and PC under mild reaction conditions.

METHOD FOR PRODUCING AROMATIC NITRILE COMPOUND AND METHOD FOR PRODUCING CARBONATE ESTER

Provided is a method for regenerating an aromatic amide compound into a corresponding aromatic nitrile compound, the method realizing a dehydration reaction of providing a target compound selectively at a high yield with generation of a by-product being suppressed. Also provided is a method for producing an aromatic nitrile compound that decreases the number of steps of dehydration reaction and significantly improves the reaction speed at a pressure close to normal pressure. Furthermore, the above-described production method is applied to a carbonate ester production method to provide a method for producing carbonate ester efficiently. The above-described objects are achieved by a method for producing an aromatic nitrile compound including a dehydration reaction of dehydrating an aromatic amide compound, in which the dehydration reaction uses diphenylether.

METHOD FOR PRODUCING AROMATIC NITRILE COMPOUND AND METHOD FOR PRODUCING CARBONIC ACID ESTER

Provided is a method for regenerating an aromatic amide compound into a corresponding aromatic nitrile compound, the method realizing a dehydration reaction of providing a target compound selectively at a high yield, with generation of a by-product being suppressed. Also provided is a method for producing an aromatic nitrile compound that decreases the number of steps of the dehydration reaction and significantly improves the reaction speed even at a pressure close to normal pressure. In addition, the above-described production method is applied to a carbonate ester production method to provide a method for producing a carbonate ester efficiently. The above-described methods are realized by a method for producing an aromatic nitrile compound including a dehydration reaction of dehydrating an aromatic amide compound, in which the dehydration reaction uses, as a solvent, any of 1,2-dimethoxybenzene, 1,3-dimethoxybenzene and 1,3,5-trimethoxybenzene.