502-97-6

Usage

Uses

Used in Medical Applications:
1,4-Dioxane-2,5-dione is used as a key component in the fabrication of artificial blood vessels due to its biodegradable and biocompatible nature. It provides the necessary structural integrity and flexibility required for such applications.
Used in Polymer Synthesis:
In the field of polymer chemistry, 1,4-Dioxane-2,5-dione is used as a monomer for the formation of aliphatic polyesters, specifically poly(glycolide), through ring-opening polymerization. This highly crystalline polymer finds applications in various industries, including medical, pharmaceutical, and environmental sectors.
Used in Drug Delivery Systems:
1,4-Dioxane-2,5-dione is also utilized in the development of drug delivery systems, where its biodegradable properties allow for controlled release of therapeutic agents, enhancing their efficacy and reducing side effects.
Used in Tissue Engineering:
In the field of tissue engineering, 1,4-Dioxane-2,5-dione is employed as a scaffold material for the growth and regeneration of various tissues, such as bone, cartilage, and skin, due to its biocompatibility and ability to support cell adhesion and proliferation.
Used in Environmental Applications:
1,4-Dioxane-2,5-dione is used in the development of biodegradable plastics and other materials, which can help reduce the environmental impact of non-degradable synthetic materials. Its biodegradable nature makes it an attractive option for sustainable product development.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C4H4O4/c5-3-1-7-4(6)2-8-3/h1-2H2

Upstream product

• 3926-62-3 sodium monochloroacetic acid 
• 79-11-8 chloroacetic acid 
• 79-14-1 glycolic Acid 
• 67-56-1 methanol 
• 107-21-1 ethylene glycol 
• 71-41-0 pentan-1-ol 
• 111-27-3 hexan-1-ol 
• 111-70-6 n-heptan1ol 
• 111-87-5 octanol 
• 112-30-1 1-Decanol 
• 71-23-8 propan-1-ol 
• 71-36-3 butan-1-ol 
• 64-17-5 ethanol 
• 23147-58-2 glycolaldehyde dimer 

Downstream Products

• 90204-88-9 N-cyclohexyl-2-hydroxyacetamide 
• 14658-93-6 2-hydroxy-N,N-dimethylacetamide 
• 39096-01-0 N,N-diethyl-2-hydroxyacetamide 
• 79-14-1 glycolic Acid 
• 107-21-1 ethylene glycol 
• 4746-61-6 glycolanilide 
• 103-70-8 Formanilid 
• 96-35-5 glycolic acid methyl ester 
• 103-82-2 phenylacetic acid 
• 110271-85-7 methyl glycolylglycolate 
• 209995-38-0 (2,4,5-trifluorophenyl)acetic acid 
• 181629-08-3 4-(hydroxymethyl)-cyclohexylmethoxycarbonylmethyl hydroxyacetate 
• 7397-62-8 butyl glycolate 
• 138-86-3 limonene. 

Relevant academic research and scientific papers

METHOD FOR PRODUCING CYCLIC ESTER

In a method for producing a cyclic ester according to an embodiment of the present invention, a mixture (I) containing an aliphatic polyester, a specific polyalkylene glycol diether, and a sulfonic acid compound as a thermal stabilizer is prepared and heated in predetermined conditions to obtain a mixture (II) in a state of solution. Furthermore, heating of the mixture (II) is continued to distill, together with the polyalkylene glycol diether, a cyclic ester formed by the depolymerization reaction, and thus a distillate (III) is obtained. The cyclic ester is recovered from the distillate (III). At this time, a specific solubilizing agent is added to at least one of the mixture (I) or (II). In this production method, the sulfonic acid compound as the thermal stabilizer is contained in the mixtures (I) and (II) and the distillate (III).

PROCESS FOR PREPARING GLYCOLIDE

According to the present invention a process is provided for producing glycolide which comprises contacting glycolaldehyde dimer with an oxidizing agent to produce a glycolide product.Preferably, the process is carried out in an aprotic environment, such as in a reaction mixture comprising the glycolaldehyde dimer, the oxidizing agent, the glycolide product and an aprotic solvent.

Preparation method of glycolide

The invention provides a preparation method of glycolide, which comprises the following steps: adding methyl glycolate and stannous octoate, stirring, continuously introducing nitrogen, heating to 150-180 DEG C to start reaction, heating to 200-210 DEG C to continue the reaction, keeping the temperature of the distillation head above the boiling point of methanol in the reaction process, ending the reaction when no methanol is evaporated, thereby obtaining the glycolide, wherein the generated yellowish-brown solid is the methyl glycolate oligomer, heating the methyl glycolate oligomer to 240-260 DEG C, keeping the vacuum degree in the reaction system at 1.0-1.5 kPa, reacting to obtain a faint yellow crystal which is a glycolide crude product, taking out the glycolide crude product, washingwith distilled water, and recrystallizing the washed glycolide crude product to obtain glycolide. According to the preparation method of glycolide provided by the invention, the intermediate productof ethylene glycol prepared by coal chemical industry is used as a raw material to obtain high-purity glycolide, the process is simple, and industrial promotion is facilitated.

METHOD FOR PRODUCING GLYCOLIDE

PROBLEM TO BE SOLVED: To provide a method for producing glycolides, with which glycolides can be produced more rapidly. SOLUTION: The method for producing glycolides comprises: an oligomer preparation step for obtaining a glycolic acid oligomer by heating an aqueous glycolic acid solution and by the dehydropolycondensation of the glycolic acid contained in the aqueous glycolic acid solution; and a depolymerization step for obtaining a glycolide by depolymerization of the glycolic acid oligomer in the presence of divalent iron ions. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

METHOD FOR PRODUCING GLYCOLIDE

PROBLEM TO BE SOLVED: To provide a method for producing glycolides, with which glycolides can be produced more rapidly. SOLUTION: The method for producing glycolides comprises: a step of adding metal iron to an aqueous glycolic acid solution; a step for obtaining a glycolic acid oligomer by the dehydropolycondensation of a glycolic acid contained in the aqueous glycolic acid solution having the metal iron added thereto; and a step for obtaining a glycolide by heating the glycolic acid oligomer for depolymerization. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

METHOD FOR PRODUCING a-HYDROXYCARBOXYLIC ACID DIMERIC CYCLIC ESTER

Provided is a method for producing a high purity α-hydroxycarboxylic acid dimeric cyclic ester while heavy-component formation from an α-hydroxycarboxylic acid oligomer is suppressed. An α-hydroxycarboxylic acid dimeric cyclic ester is obtained by performing a depolymerization reaction in the coexistence of an inorganic acid or an inorganic acid salt or a mixture thereof; and an organophosphorus compound.

Synthetic method of glycolide

The invention discloses a synthetic method of glycolide. The synthetic method comprises the following steps: placing chloroacetyl chloride and glycollic acid molten in a heating manner into a reactor,adding carbonate, reacting, and obtaining chloracetylglycollic acid; and mixing chloracetylglycollic acid and carbonate, stirring, decompression distilling, and distilling out a glycolide crude product, wherein the reaction formula is shown in the description. The raw materials chloroacetyl chloride, glycollic acid and carbonate used in the synthetic method are massively available in the market,and no massive acidic waste water is produced in the synthesis process, so that the environmental pollution is greatly reduced. According to the synthetic method, no organic solvent is used, so that not only can the cost be reduced, but also the environmental pollution is avoided, and the harm on the body of the working personnel is reduced. Chloroacetyl chloride used in the invention is low in price; compared with the traditional process completely using glycolic acid, the production cost is greatly reduced; meanwhile, no catalyst is needed, so that the production operation is simpler. The yield of glycolide is correspondingly increased.

Mild Access to N-Formylation of Primary Amines using Ethers as C1 Synthons under Metal-Free Conditions

A new synthetic protocol has been developed for the synthesis of N-formamide derivatives using ethers as a C1 synthon under metal-free reaction conditions. The reaction is proposed to proceed through C?H functionalization, C?O cleavage, and C?N bond formation. This protocol is applicable to a variety of primary amines resulting in N-formamides in moderate to good yields. 1,4-dioxane was chosen as best C1 synthon after screening with various ethers. Mechanistic studies disclosed that the reaction proceeds through a radical pathway. While using α-amino ketones a α-alkylation product was formed rather than formylation. By replacing dioxane with Tetramethylethylenediamine (TMEDA) under standard conditions also gave the N-formamide derivatives in moderate yields. (Figure presented.).

Catalytic Gas-Phase Cyclization of Glycolate Esters: A Novel Route Toward Glycolide-Based Bioplastics

A catalytic process to produce glycolide, the cyclic dimer of glycolic acid (GA), is proposed. Glycolide is the key building block of the biodegradable plastic polyglycolic acid. Instead of the current industrial two-step route, which involves the polycondensation of GA and a subsequent backbiting reaction, a new route based on the gas-phase transesterification of methyl glycolate (MGA) over a fixed catalyst bed is presented. With specific supported TiO2 catalysts, a high glycolide selectivity of 75–78 % can be achieved at the thermodynamically-limited equilibrium conversion of MGA (54 % at 300 °C, 5.6 vol% MGA, 1 atm). The absence of solvent and the continuous nature of the process should allow for easy product separation and recycling of unconverted esters, while the few side-products, i. e. linear alkyl glycolate dimers and trimers seem recoverable via methanolysis. The reaction is compared to the cyclization of other α-hydroxy esters, such as methyl lactate to lactide, over the same catalysts, in terms of kinetics and thermodynamics. The absence of a methyl substitution on the α-carbon seems to lead to faster cyclization kinetics of MGA when compared to methyl lactate or the double-substituted methyl-2-hydroxy-isobutyrate. Contrarily, glycolide production is less favored thermodynamically compared to lactide. The absence of glycolide decomposition at temperatures up to 300 °C however allows to increase equilibrium conversion by taking the endergonic reaction to higher temperatures.

METHOD FOR PRODUCING GLYCOLIDE, WHICH IS PROVIDED WITH RECTIFICATION STEP BY MEANS OF GAS-LIQUID COUNTERCURRENT CONTACT, AND METHOD FOR PURIFYING CRUDE GLYCOLIDE

A method for producing glycolide provided with: step (1) wherein a GAO composition, which preferably contains a high-boiling-point organic solvent or a solubilizing agent, is supplied into a reactor and heated to a temperature at which a depolymerization reaction of the GAO occurs; step (2) wherein the heating is continued to subject the GAO to the depolymerization reaction, thereby producing glycolide; step (3) wherein glycolide is distilled out of the reactor; step (4) wherein the distillate is introduced into a rectifier and is rectified by means of gas-liquid countercurrent contact; and step (5) wherein glycolide is recovered. A method for purifying crude glycolide provided with: step (i) wherein a crude glycolide composition, which preferably contains a high-boiling-point organic solvent or a solubilizing agent, is supplied into a reactor and heated so that glycolicde is distilled; step (ii) wherein the distillate is introduced into a rectifier and is rectified by means of gas-liquid countercurrent contact; and step (iii) wherein glycolide is recovered. A glycolide producing apparatus and a crude glycolide purifying apparatus, each of which is provided with a reactor and a rectifier.