Dimethyl dicarbonate

Base Information

• Chemical Name: Dimethyl dicarbonate
• CAS No.: 4525-33-1
• Molecular Formula: C4H6O5
• Molecular Weight: 134.089
• Hs Code.: 2920 90 10
• European Community (EC) Number: 224-859-8
• UNII: 1AY9229ZMG
• DSSTox Substance ID: DTXSID2052108
• Nikkaji Number: J205.896K
• Wikipedia: Dimethyl_dicarbonate
• Wikidata: Q416985
• Metabolomics Workbench ID: 45763
• Mol file: 4525-33-1.mol

Synonyms:dimethyl dicarbonate;dimethyl pyrocarbonate;Velcorin

Chemical Property of Dimethyl dicarbonate

Chemical Property:

• Vapor Pressure: 1.4mmHg at 25°C
• Melting Point: 15-17oC
• Refractive Index: n20/D 1.392(lit.)
• Boiling Point: 171.4 °C at 760 mmHg
• Flash Point: 80 °C
• PSA: 61.83000
• Density: 1.243 g/cm³
• LogP: 0.53580
• Storage Temp.: 2-8°C
• Solubility.: 35g/l (decomposition)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 134.02152329
• Heavy Atom Count: 9
• Complexity: 104

Purity/Quality:

99% ^*data from raw suppliers

Dimethyl dicarbonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 21/22-23-34
• Safety Statements: 18-26-28-36/37/39-38-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)OC(=O)OC
• Description: Dimethyl dicarbonate (DMDC), also known as Viguolin, is a kind of fruit juice beverage preservative (INS No. 242) that is allowed to be used in my country's food additive use standards. Under normal or even low temperature conditions, DMDC has a strong ability to kill many contaminating bacteria in fruit juice drinks, and its antiseptic effect is closely related to the modification and inactivation of key enzyme proteins in the bacteria by DMDC. Compared with other physical sterilization technologies, the use of DMDC is low in cost, simple and safe to operate, and does not affect the taste, smell and color of the product. It has become one of the hotspots in the research of emerging non-thermal sterilization technologies.
• Uses: Dimethyl dicarbonate (DMDC), a chemical used to combat brettanomyces in wine, is classified as an additive.DMDC is allowed for the preservation of nonalcoholic flavored drinks, alcohol-free wine, and liquid-tea concentrate in ingoing amounts up to 250 mg/L.Because of its reactivity to nucleophilic groups present in proteins, it easily binds to these, which, in the case of enzymes, leads to inactivation of these and hence to inactivation of microorganisms.150In an aqueous medium, it undergoes complete hydrolysis to methanol and carbon dioxide within a few hours. The EC Directive provides a remark that dimethyl dicarbonate residues are not detectable in drinks. Dimethyl Dicarbonate(DMDC) is a microbial control agent used in wine; ready-to-drink teas; nonjuice-containing beverages; carbonated,dilute beverages containing juice, fruit flavor or both with the juice content not exceeding 50%.Dimethyl Dicarbonate has been commonly used as a antimicrobial agent for a broad spectrum of microorganisms. The primary target microorganisms of DMDC are yeasts, including Saccharomyces, Zygosaccharomyces, Rhodotorula, Candida, Pichia, Torulopsis, Torula, Endomyces, Kloeckera and Hansenula. DMDC is also bactericidal to a number of species including Acetobacter pasteurianus, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, several Lactobacillus species and Pediococcus cerevisiae DMDC has also been shown to be bactericidal against Escherichia coli O157:H7.The antimicrobial effect of DMDC results from the deactivation of microbial enzymes, mainly through reaction with protein imidazole and amine groups, leading to the destruction of the microorganisms. The remaining unreacted DMDC breaks down rapidly into methanol and carbon dioxide. The DMDC activity is based on the hydrolysis rate. Hydrolysis occurs when DMDC reacts with water and the rate is dependent on the temperature of the beverage or wine. It takes about four hours at 10°C (50°F) or two hours at 20°C (68°F) for DMDC completely breaking down.

Technology Process of Dimethyl dicarbonate

There total 4 articles about Dimethyl dicarbonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

methyl chloroformate (79-22-1) → dimethyl dicarbonate (4525-33-1)

Guidance literature:

With sodium hydroxide; triisooctyl amine; In water; toluene; at 17 ℃; for 1.25h; Product distribution / selectivity; Alkaline conditions;

Reference yield:

phosgene (75-44-5) + sodium methyl carbonate (6482-39-9) → dimethyl dicarbonate (4525-33-1)

Guidance literature:

DOI:10.1021/jo01052a516

Reference yield:

methyl chloroformate (79-22-1) → dimethyl dicarbonate (4525-33-1)

Guidance literature:

upstream raw materials:

methyl chloroformate

phosgene

sodium methyl carbonate

Downstream raw materials:

carbon dioxide

carbonic acid dimethyl ester

methyl 3-pyridinecarboxylate

(4-(chlorosulfonyl)phenyl)methylene diacetate

Refernces

• 1、 -. "METHOD FOR PREPARING DIALKYL DICARBONATES USING AMINE OXIDES". Paragraph 0044; 0045; 0046; 0047; 0048; 0049; 0050. . Retrieved 2020/01/24.
• 2、 -. "METHOD FOR PRODUCING DIALKYL DICARBONATES". Page/Page column 6. . Retrieved 2008/06/13.