2,3-Butanedione

Base Information

• Chemical Name: 2,3-Butanedione
• CAS No.: 431-03-8
• Deprecated CAS: 151677-70-2
• Molecular Formula: C4H6O2
• Molecular Weight: 86.0904
• Hs Code.: 29141990
• European Community (EC) Number: 207-069-8
• ICSC Number: 1168
• NSC Number: 8750
• UN Number: 2346
• UNII: K324J5K4HM
• DSSTox Substance ID: DTXSID6021583
• Nikkaji Number: J2.586K
• Wikipedia: Diacetyl
• Wikidata: Q408916
• Metabolomics Workbench ID: 5418
• ChEMBL ID: CHEMBL365809
• Mol file: 431-03-8.mol

Synonyms:2,3 Butanedione;2,3-Butanedione;Biacetyl;Diacetyl;Diketobutane;Dimethyldiketone;Dimethylglyoxal

Chemical Property of 2,3-Butanedione

Chemical Property:

• Appearance/Colour: liquid with a butter-like odour
• Vapor Pressure: 52.2 mm Hg ( 20 °C)
• Melting Point: -4--2 °C
• Refractive Index: n20/D 1.394(lit.)
• Boiling Point: 88 °C at 760 mmHg
• Flash Point: 5.5 °C
• PSA: 34.14000
• Density: 0.969 g/cm³
• LogP: 0.16440
• Storage Temp.: 2-8°C
• Solubility.: 200g/l
• Water Solubility.: 200 g/L (20 ºC)
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 86.036779430
• Heavy Atom Count: 6
• Complexity: 71.5
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

2,3-Butanedione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, Xn
• Hazard Codes: F,Xn
• Statements: 11-20/22-38-41-36/38-20/21/22-37/38
• Safety Statements: 9-16-26-37/39-36/37/39-39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aliphatic Ketones, Other
• Canonical SMILES: CC(=O)C(=O)C
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes. The substance is irritating to the skin and respiratory tract. The substance may cause effects on the central nervous system, lungs and respiratory tract. Exposure at high levels could cause lowering of consciousness.
• Effects of Long Term Exposure: Lungs may be affected by repeated or prolongated exposure to the vapour. This may result in impaired functions.
• Uses: Diacetyl (2,3-butanedione) is a naturally occurring product and can be found in numerous foods such as butter, milk, cheese, smoked or roasted meats, breads, fruits, vegetables, coffee, beer, and wine. Diacetyl is synthesized to be used as a food additive to impart a buttery flavor and has been designated as a generally recognized as safe (GRAS) substance with low acute toxicity (FDA, 1980). Desirable flavor concentrations in food are approximately 0.05–5.0 ppm and above that range it imparts a disagreeable taste. The most recognized recent use has been in microwave popcorn, but it has also been used for many other products (NTP, 1994, 2007). Diacetyl may be used in additives as a liquid, paste, or powder (Boylstein et al., 2006). It meets GB 2760—1996 standards of edible spices for the moment. It is mainly used for the preparation of food essence like cream, cheese fermentation and coffee typed essence,used in milk, butter, margarine, cheese, sweets and other flavors, such as berry, caramel, chocolate, coffee, cherry, vanilla bean, honey, cocoa, fruit, wine, aroma, rum, nuts, almonds, ginger and so on. It can also be used in fresh fruit fragrance essence for makeup or new type essence in trace amount, and be used as gelatin hardening agent and photographic adhesive agent. 2,3-Butanedione is a flavoring agent that is a clear yellow to yellowish green liquid with a strong pungent odor. It is chemically synthesized from methyl ethyl ketone. It is miscible in water, glycerin, alcohol, and ether, and in very dilute water solution it has a typical buttery odor and flavor. It is used as Carrier of aroma of butter, vinegar, coffee, and other foods. It is also used Inactivates aminopeptidase-N, precursor to α-diones, Cyclocondensation with amines has been used to form triazine and pteridine ring systems.
• Description: 2,3-Butanedione, also known as Diacetyl, is a reactive diketone in artificial butter flavors. It is a water-soluble and volatile, alpha-diketone compound that has a buttery odor. Diacetyl occurs naturally in plants, fruits, coffee, honey, cocoa, and dairy products. It is a natural by-product of fermentation and is found in beer and wine. Diacetyl is also present in cigarette smoke.Diacetyl can be synthesized by converting 2-butanone to an isonitroso compound and then hydrolyzing it with hydrochloric acid. Other methods for producing diacetyl include oxidation of 2-butanone over a copper catalyst at 300°C and dehydrogenation of 2,3-butanediol over a copper or silver catalyst. In addition, diacetyl can be synthesized through the acid catalyzed condensation of 1-hydroxyacetone and formaldehyde. Naturally occurring diacetyl is also available from starter distillate, a by-product of dairy product fermentation. Although diacetyl and starter distillates are liquids, they can be converted to a powdered form by encapsulating them within a solid material to prevent volatility. Diacetyl in powdered form is also found in flavorings that have been spray dried. The boiling point of diacetyl is 88°C with a calculated vapor pressure of 55 mmHg at 20°C.

Technology Process of 2,3-Butanedione

There total 453 articles about 2,3-Butanedione 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: 82.0%

acetic anhydride (108-24-7) + (2E)-3-phenyl-2-propen-1-ol (4407-36-7) → Cinnamyl acetate (21040-45-9) + dimethylglyoxal (431-03-8)

Guidance literature:

With cobalt(II) chloride; In acetonitrile; at 25 ℃; for 4h;

DOI:10.1021/jo00033a020

Reference yield: 68.0%

methoxybenzene (100-66-3) + acetyl chloride (75-36-5) → 2-Methoxyacetophenone (579-74-8) + 2,2'-Dimethoxybiphenyl (4877-93-4) + 4-acetyloxyacetophenone (13031-43-1) + dimethylglyoxal (431-03-8) + 1-(4-methoxyphenyl)ethanone (100-06-1)

Guidance literature:

CoCl₂; In acetonitrile; at 80 ℃; Product distribution; Mechanism; other acid chlorides; also with benzene, toluene, thioanisole, p-methylanisole; effect of added 2,6-di-t-butyl-4-methylphenol;

DOI:10.1016/S0040-4039(00)93460-9

Reference yield: 22.0%

dibenzyl ether (103-50-4) + acetyl chloride (75-36-5) → N-(phenylmethyl)acetamide (588-46-5) + Benzyl acetate (140-11-4) + benzyl chloride (100-44-7) + dimethylglyoxal (431-03-8)

Guidance literature:

CoCl₂; In acetonitrile; Yields of byproduct given; Ambient temperature;

DOI:10.1016/S0040-4020(01)96041-7

upstream raw materials:

diazomethane

diethyl ether

Glyoxal

2-oxopropanal

Downstream raw materials:

dimethyl-2,3 pyrido<2,3-b>pyrazine

butane-2,3-dione bis(2′-pyridylhydrazone)

2,3-Dimethyl-1,4,5,8-tetraaza-naphthalin

6,7-dimethyl-pteridine

Refernces

• 1、 Pound. "". . p. 1449. Retrieved 1947.
• 2、 Fraser, Mark S.,Hamilton, Gordon A.. "Models for Oxygenases That Catalyze the Cleavage of Carbon-Carbon Bonds: Kinetics and Mechanism of the Decomposition of 2,3-Dimethyl-3-peroxyindolenines in Aqueous Solution". . p. 4203 - 4211. Retrieved 1982.
• 3、 Singh, Bharat,Saxena, B. B. L.,Samant, A. K.. "KINETICS AND MECHANISM OF THE OXIDATION OF SOME ALIPHATIC KETONES BY N-BROMOACETAMIDE IN ACIDIC MEDIA". . p. 3321 - 3324. Retrieved 1984.
• 4、 Sleiman,El Dib,Ballesteros,Moreno,Albaladejo,Canosa,Chakir. "Kinetics and mechanism of the tropospheric reaction of 3-hydroxy-3-methyl- 2-butanone with Cl atoms". . p. 6163 - 6170. Retrieved 2014.
• 5、 Michaelian,Hoecker,Hammer. "-". . . Retrieved 1938.
• 6、 Ho et al.. "-". . p. 1632,1633, 1634. Retrieved 1975.
• 7、 Gierczak,Rajakumar,Flad, Jonathan E.,Burkholder, James B.. "Rate coefficients for the reaction of the acetyl radical, CH3CO, with Cl2 between 253 and 384 K". . p. 543 - 553. Retrieved 2009.
• 8、 Johlin. "-". . p. 892. Retrieved 1915.
• 9、 Spence,Wild. "-". . . Retrieved 1937.
• 10、 Sakuraba,Matsushima. "-". . p. 911. Retrieved 1972.