2,3-Butanedione

Product Name:

2,3-Butanedione

Synonyms:

dimnertong;2,3-Butanedione 2,3-Diketobutane Dimethylglyoxal;2,3-Butanedione 97%;Two2,3-butylketone;2, 3 - butyl diketone;2,3-DIOXOBUTANE;2,3-DIKETOBUTANE;2,3-BUTANEDIONE

CAS:

431-03-8

MF:

C4H6O2

MW:

86.09

EINECS:

207-069-8

Product Categories:

Ketones;Organic Building Blocks;B;Bioactive Small Molecules;Building Blocks;C3 to C6;Organics;Biochemistry;Reagents for Oligosaccharide Synthesis;ketone Flavor;Carbonyl Compounds;Cell Biology;Chemical Synthesis

Mol File:

431-03-8.mol

Melting point 

-4--2 °C

Boiling point 

88 °C(lit.)

density 

0.985 g/mL at 20 °C

vapor density 

3 (vs air)

vapor pressure 

52.2 mm Hg ( 20 °C)

FEMA 

2370 | DIACETYL

refractive index 

n20/D 1.394(lit.)

Fp 

45 °F

storage temp. 

2-8°C

solubility 

200g/l

form 

Liquid

color 

Clear yellow

explosive limit

2.4-13.0%(V)

Odor Threshold

0.00005ppm

Water Solubility 

200 g/L (20 ºC)

JECFA Number

408

Merck 

14,2966

BRN 

605398

Stability:

Stable. Flammable. Incompatible with acids, strong bases, metals, reducing agents, oxidizing agents. Protect from moisture and water. Note low flashpoint.

InChIKey

QSJXEFYPDANLFS-UHFFFAOYSA-N

CAS DataBase Reference

431-03-8(CAS DataBase Reference)

NIST Chemistry Reference

2,3-Butanedione(431-03-8)

EPA Substance Registry System

2,3-Butanedione (431-03-8)

Hazard Codes 

F,Xn

Risk Statements 

11-20/22-38-41-36/38-20/21/22-37/38

Safety Statements 

9-16-26-37/39-36/37/39-39

RIDADR 

UN 2346 3/PG 2

WGK Germany 

2

RTECS 

EK2625000

F 

13

Autoignition Temperature

365 °C

TSCA 

Yes

HazardClass 

3

PackingGroup 

II

HS Code 

29141990

Hazardous Substances Data

431-03-8(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 1580 mg/kg (Jenner)

Content analysis

The content of 2,3-Butanedione is analyzed according to method 1(hydroxylamine method) of the aldehyde and ketone analyzing methods (OT-7). The sample weight is 500mg. The equivalent factor (e) in calculation is 21.52 .It is Fit to be analyzed using nonpolar column in GT-10-4.

Toxicity

Not specified by ADI (FAO/WHO，1994)
GRAS(FEMA；FDA，§184．1278，2000)

Quantity restrictions

FEMA(mg/kg)：FEMA(mg/kg)：soft drinks 2.5；cold drinks 5.9；sweets 21；bakery products44；puddings 19；chewing gum 35；shortening 11.

Chemical Properties

Yellow to yellow green liquid, a creamy fragrance after bulk dilution (1mg/kg), high vapor pressure is, evaporate quickly at room temperature, melting point-3～-4℃，boiling point 87～88℃, flash point 13℃. Soluble in ethanol, ether, most non-volatile oil and propylene glycol, soluble in glycerin and water, insoluble in mineral oil. Natural products exist in laurel oil, ajawa oil, angelica root oil, raspberry, strawberry, cream, Wine etc. Because it is volatile, it only exists in in the primary distillate and distilled water. 

Usage

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.

Production

In nature, Diacetyl exists widely in many Plant essential oils, such as iris oil, angelica oil, laurel oil, etc. It is the main component of butter and other natural products fragrance.
In industry, methyl ethyl ketone was treated with nitrite acid to generate diacetylmonoxime. Diacetylmonoxime is then decomposed by sulfuric acid to produce Butanedione. 
Diacetyl can be obtained by chemical ionization method from high content of essential oil. Two parts of phosphoric acid were added to one part of essential oil to
produce crystalline adduct CH3CO-COCH3. Butanedione was released after the addition of water. Excessive addition of phosphoric acid will lead to liquid adduct product.
Diacetyl can be obtained by special fermentation of glucose.
Diacetyl can be synthesized using methyl ethyl ketone as raw material.
Diacetyl was oxidized by sodium nitrite in the presence of hydrochloric acid,
Then, the process of istillation is carried out after hydrolysis in the presence of sulfuric acid to produce Butanedione.

Category

flammable liquid

Acute toxicity

Oral-rat  LD50: 1580mg/kg, oral-mice: 250 mg/kg

Stimulus data

Skin-rabbit 500 mg/24h middle

Flammability and Hazardous characteristics

Flammable in case of fire, high temperature and oxidant, Combustion produces irritating smoke.

Storage

Ventilated and dry warehouse with low temperature. Separated from oxidant, acid.

Chemical Properties

liquid with a butter-like odour

Chemical Properties

2,3-Butanedione is a constituent of many fruit and food aromas and well-known as a constituent of butter. Many methods are known for itsmanufacture, for example, dehydrogenation of 2,3-butanediol with a copper chromite catalyst. Biotechnological production on an industrial scale is referred. It is used mainly in aromas for butter and roasted notes. Large quantities are used for flavoring margarine; small amounts are used in perfumes.

Chemical Properties

Diacetyl has a very strong buttery odor in very dilute solution.

Occurrence

Reported in the oils of: Finnish pine, angelica and lavender; in the flowers of Polyalthia canangioides Boerl. var. angustifolia and Fagroea racemosa Jack. The following plants are also reported to contain diacetyl: Monodora grandiflora Benth., Magnolia tripetale L., Ximenia aegyptiaca L., Petasites fragrans Presl., various narcissi and tulips. It has been identified in certain types of wine, the natural aromas of raspberry and strawberry, and the oils of lavender, lavandin, Réunion geranium, Java citronella, and Cistus ladaniferus L. It is also reported to be found in ligonberry, guava, raspberry, strawberry, cabbage, peas, tomato, vinegar, various cheeses, yogurt, milk, butter, chicken, beef, mutton, pork, cognac, beer, wines, whiskies, tea and coffee.

Uses

2,3-Butanedione is a flavoring agent that is a clear yellow to yellowish green liquid with a strong pungent odor. It is also known as 2,3-butanedione and 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.

Uses

Inactivates aminopeptidase-N.1 Cyclocondensation with amines has been used to form triazine2 and pteridine ring systems.3 Also used as a precursor to α-diones.4

Uses

Carrier of aroma of butter, vinegar, coffee, and other foods.

Definition

ChEBI: An alpha-diketone that is butane substituted by oxo groups at positions 2 and 3. It is a metabolite produced during the malolactic fermentation.

Preparation

From methyl ethyl ketone by converting to the isonitroso compound and then decomposing to diacetyl by hydrolysis with HCl; by fermentation of glucose via methyl acetyl carbinol.

Aroma threshold values

Detection: 0.3 to 15 ppb: recognition: 5 ppb

Taste threshold values

Taste characteristics at 50 ppm: sweet, buttery, creamy and milky.

General Description

A clear colorless liquid with a strong chlorine-like odor. Flash point 80°F. Less dense than water. Vapors heavier than air.

Air & Water Reactions

Highly flammable. Soluble in water.

Reactivity Profile

2,3-Butanedione is a flammable liquid, b.p. 88° C, moderately toxic. When heated to decomposition 2,3-Butanedione emits acrid smoke and fumes [Sax, 9th ed., 1996, p. 544].

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety Profile

A poison by ingestion and intraperitoneal routes. A skin irritant. Human inhalation hazard in popcorn manufacture. Human mutation data reported. Flammable liquid. Dangerous fire hazard when exposed to heat or flame. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and fumes. See also KETONES.

Toxicology

Diacetyl is an intensely yellowish or greenish-yellow mobile liquid. It has a very powerful and diffusive, pungent, buttery odor and typically used in flavor compositions, including butter, milk, cream, and cheese. Diacetyl was found to be mutagenic in Ames test conducted under various different conditions with Salmonella typhimurium strains. For example, diacetyl was mutagenic by TA100 in the absence of S9 metabolic activation at doses up to 40 mM/plate. It was mutagenic in a modified Ames assay in Salmonella typhimurium strains TA100 with and without S9 activation. The acute oral LD50 of diacetyl in guinea pigs was calculated to be 990 mg/kg. The acute oral LD50 of diacetyl in male rats was calculated to be 3400 mg/kg, and in female rats, the LD50 was calculated to be 3000 mg/kg. When male and female rats were administered via gavage a daily dose of 1, 30, 90, or 540 mg/kg/day of diacetyl in water for 90 days, the high-dose produced anemia, decreased weight gain, increased water consumption, increased leukocyte count, and an increase in the relative weights of liver, kidneys, and adrenal and pituitary glands. The data for teratogenicity and carcinogenicity are not available. Although the FDA has affirmed diacetyl GRAS as a flavoring agent, low molecular weight carbonyls, such as formaldehyde, acetaldehyde, and glyoxal have been reported to possess a certain chronic toxicity.

Carcinogenicity

Diacetyl was tested for its ability to induce primary lung tumors in strain A/He mice. The mice received three IP injections of diacetyl per week for 8 weeks and were killed 24 weeks after the first injection. The total dose of diacetyl given was 1.7 or 8.4 g/kg. The number of lung tumors in diacetyl exposed mice was not significantly different from the control mice.
Inhalation carcinogenicity bioassays withWistar Han rats and B6C3F1 mice at exposure levels of 0, 12.5, 25, and 50 ppm are underway according to the National Toxicology Program.

Purification Methods

Dry biacetyl over anhydrous CaSO4, CaCl2 or MgSO4, then distil it in a vacuum under nitrogen, taking the middle fraction and storing it at Dry-Ice temperature in the dark (to prevent polymerization). [Beilstein 1 IV 3644.]

Preparation Products

1,4-Butanediol-->Acetonylacetone-->Ursodeoxycholic acid-->2-AMINO-6,7-DIMETHYL-4-HYDROXYPTERIDINE-->Tetramethylpyrazine-->Clethodim-->2-AMINO-6,7-DIMETHYL-4-HYDROXY-5,6,7,8-TETRAHYDROPTERIDINE MONOHYDROCHLORIDE-->DL-Tyrosine-->3-Hydroxy-2-butanone-->2,3-Dimethylpyrazine-->pigment yellow 155-->diacetyl tartaric acid ester ofmono-and diglycerides-->Starter distilIate

Raw materials

Etanol-->Sulfuric acid-->Sodium nitrite-->2-Butanone-->Selenium dioxide-->Methyl vinyl ketone-->AROMA-->1-BUTEN-3-YNE-->Orris oil-->LAUREL OIL FROM LAURUS NOBILIS-->Angelica oil-->Polishing compound,yellow