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431-03-8

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431-03-8 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 431-03-8 differently. You can refer to the following data:
1. 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.
2. 2,3-Butanedione has a very strong buttery odor in very dilute solution. It 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.

Uses

Different sources of media describe the Uses of 431-03-8 differently. You can refer to the following data:
1. 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. 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.

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.

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.

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.

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.

Definition

ChEBI: 2,3-Butanedione is an alpha-diketone that is butane substituted by oxo groups at positions 2 and 3. It is a metabolite produced during the malolactic fermentation. It has a role as a Saccharomyces cerevisiae metabolite and an Escherichia coli metabolite.

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

2,3-Butanedione appears as 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.

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.

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.

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.

Environmental Fate

Mechanisms of diacetyl-induced toxicity are not known, but some possible mechanisms of toxicity have been postulated. The adjacent carbonyl groups on diacetyl make it a reactive compound. In vitro studies have demonstrated that diacetyl can bind to arginine and inactivate proteins. The electron affinity of diacetyl suggests that it can undergo electron transfer activity, which can lead to oxidative stress by oxygen redox cycling. Redox cycling and oxidative stress may also be initiated during metabolism of diacetyl by DCXR (dicarbonyl/L-xylulose reductase). Reactive oxygen species are known to be produced from metabolic activation of dicarbonyl substrates by related carbonyl reductase enzymes in the presence of O2.

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.]

Toxicity evaluation

Diacetyl released to the environment is expected to be highly mobile in soil and is not expected to adsorb to suspended sediments and solids in water. Diacetyl is degraded by a bacterium tentatively identified as Pseudomonas. Bioconcentration of diacetyl by aquatic organisms is not likely. Diacetyl is expected to volatilize from soil and water surfaces, and diacetyl is likely to exist solely as a vapor in the ambient atmosphere. In the atmosphere, diacetyl is degraded by photochemically produced hydroxyl radicals and it undergoes photolysis.

Check Digit Verification of cas no

The CAS Registry Mumber 431-03-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,3 and 1 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 431-03:
(5*4)+(4*3)+(3*1)+(2*0)+(1*3)=38
38 % 10 = 8
So 431-03-8 is a valid CAS Registry Number.
InChI:InChI=1/C4H6O2/c1-3(5)4(2)6/h1-2H3

431-03-8 Well-known Company Product Price

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  • TCI America

  • (B0682)  Diacetyl  >98.0%(GC)

  • 431-03-8

  • 25mL

  • 198.00CNY

  • Detail
  • TCI America

  • (B0682)  Diacetyl  >98.0%(GC)

  • 431-03-8

  • 100mL

  • 300.00CNY

  • Detail
  • TCI America

  • (B0682)  Diacetyl  >98.0%(GC)

  • 431-03-8

  • 500mL

  • 624.00CNY

  • Detail
  • Alfa Aesar

  • (A14217)  2,3-Butanedione, 99%   

  • 431-03-8

  • 10g

  • 211.0CNY

  • Detail
  • Alfa Aesar

  • (A14217)  2,3-Butanedione, 99%   

  • 431-03-8

  • 100g

  • 321.0CNY

  • Detail
  • Alfa Aesar

  • (A14217)  2,3-Butanedione, 99%   

  • 431-03-8

  • 500g

  • 1040.0CNY

  • Detail
  • Sigma-Aldrich

  • (11038)  2,3-Butanedione  analytical standard

  • 431-03-8

  • 11038-1ML-F

  • 255.06CNY

  • Detail
  • Sigma-Aldrich

  • (11038)  2,3-Butanedione  analytical standard

  • 431-03-8

  • 11038-5ML-F

  • 993.33CNY

  • Detail

431-03-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name butane-2,3-dione

1.2 Other means of identification

Product number -
Other names 2,3-Butanedione

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:431-03-8 SDS

431-03-8Relevant articles and documents

-

Nakagawa et al.

, p. 269,273,274 (1960)

-

-

Waters

, (1947)

-

AZIRINYL AND DIAZIRINYL (CHLORIDE) ION PAIRS AS INTERMEDIATES

Krogh-Jespersen, Karsten,Young, Claire M.,Moss, Robert A.,Wiostowski, Marek

, p. 2339 - 2342 (1982)

Both ab initio calculations and experimental observations support the intermediacy of diazirinyl or azirinyl cation-chloride anion pairs in transformations (1), (2), and (4).

-

Avery,Cvetanovic

, p. 3727 (1965)

-

-

Cvetanovic

, p. 775 (1956)

-

Reaction Kitenics in Acetyl Chemistry over a Wide Range of Temperature and Pressure

Anastasi, Christopher,Maw, Paul R.

, p. 2423 - 2434 (1982)

The molecular modulation spectrometer has been used to study the complex chemical kitenics involed in acetyl radical chemistry.This has involved direct monitoring of both acetyl and methyl radicals in the same experiment and over a variety of temperatures (263 /1019 molecule cm-3 = 2.7) conditions.These measurements have been complemented by a non-linear least-squares analysis of the experimental data and simple product studies.Rate data on four reactions and the absorption cross-section of the acetyl radical at 223 nm have been determined in this way.Unimolecular rate theory, based on Kassel integrals, has been applied to the pressure-dependent formation and decay of the radical to extract limiting values for the rate constants at T = 303 and 343 K.

Synthesis of 2,3-butanedione over TS-1, Ti-NCl, TiMCM-41, Ti-Beta, Fe-Si, Fe-Beta and VS-1 zeolites

Beltramone, Andrea,Gomez, Marcos,Pierella, Liliana,Anunziata, Oscar

, p. 610 - 611 (2000)

The purpose of this work is the synthesis of 2,3-butanedione (diacetyl) by selective oxidation of 2-butanone (methyl ethyl ketone) in the presence of O2 and H2O2 30% as oxidants. All the tests were performed over several selective oxidation zeolite catalysts, synthesized and characterized in our laboratory.

Synthesis of Dialkyl- and Alkylacylrhenium Complexes by Alkylation of Anionic Rhenium Complexes at the Metal Center. Mechanism of a Double Carbonylation Reaction That Proceeds via the Formation of Free Methyl Radicals in Solution

Goldberg, Karen I.,Bergman, Robert G.

, p. 1285 - 1299 (1989)

The site of alkylation of salts of acylrhenates such as Li(1+)(1-) (1) can be controlled by adjusting the hardness of the alkylating agent.Thus, treatment of 1 with the hard alkylating agent (CH3)3OPF6 gives predominantly the clssical Fischer carbene complex Cp(CO)2Re=C(OCH3)(CH3) (2), whereas reaction with the softer electrophile CH3I leads almost exclusively to the new metal-alkylated complex Cp(CO)2Re(CH3)(COCH3) (3).The structure of 3 has been determined by X-ray diffraction.The availability of this material, a relatively rare example of astable alkylacylmetal complex, has provided an opportunity to study the products and mechanisms of its carbon-carbon bond-forming decomposition reactions.Thermally, the alkyl acyl complex undergoes simple reductive elimination, leading (in the presence of a metal-scavenging ligand L) to a quantitative yield of acetone and CpRe(CO)2(L).Photochemically, a more complicated reaction takes place, especially under 20 atm of CO, where CpRe(CO)3 and 2,3-butanedione are formed.Strikingly, irradiation of Cp(CO)2Re(CH3)2 (9) under 20 atm of CO gives products identical with those formed from 3.Labeling experiments using (13)CO and mixtures of acetyl- and propionylrhenium complexes are inconsistent with a mechanism involving simple migratory CO insertion followed by reductive elimination.They are, however, consistent with metal-carbon bond homolysis leading to methyl and acetyl radicals, followed by carbonylation of the methyl radicals to give a second source of acetyl radicals; these reactive intermediates then dimerize to give 2,3-butanedione.Confirmation of this mechanism was obtained by trapping all the initially formed radicals withhalogen donors.BrCCl3, proved to be much more efficient than CCl4 for this purpose: irradiation of alkyl acyl complex 3 in the presence of BrCCl3 diverted the reaction completely from 2,3-butanedione production, giving instead CH3Br, CH3COBr, Cp(CO)2Re(CH3)Br, and Cp(CO)2Re(CH3CO)Br.

-

Arnett et al.

, p. 2482,2483, 2485 (1962)

-

OXIDATION OF ALIPHATIC KETONES BY BROMAMINE-B: A KINETIC STUDY

Mahadevappa, D.S.,Mohan, K.,Ananda, S.

, p. 4857 - 4866 (1986)

The kinetics of oxidation of propan-2-one, butan-2-one, pentan-2-one, pentan-3-one and 4-methyl pentan-2-one by sodium N-bromobenzenesulphonamide or bromamine-B (BAB) in perchloric acid medium was studied at 30 deg C.The rate shows a first order dependence each on and +> and is independent of .Variation of ionic strength of medium and addition of the reaction product benzenesulphonamide have no effect on the rate and the dielectric effect is positive.The proposed mechanism involves acid catalysed enolisation of ketone in the rate limiting step followed by a fast interaction with the oxidant.This is supported by the magnitude of inverse solvent isotope effect of 1.62 +/- 0.01 observed in D2O medium.Activation parameters Ea, ΔH*, ΔS*, ΔG* and log A have been calculated by studying the reaction at different temperatures (293-309 K).

-

Gandini,Hackett

, p. 6195,6198 - 6204 (1977)

-

Atmospheric Chemistry of Selected Hydroxycarbonyls

Aschmann, Sara M.,Arey, Janet,Atkinson, Roger

, p. 3998 - 4003 (2000)

Using a relative rate method, rate constants have been measured at 296 ± 2 K for the gas-phase reactions of the OH radical with 1-hydroxy-2-butanone, 3-hydroxy-2-butanone, 1-hydroxy-3-butanone, 1-hydroxy-2-methyl-3-butanone, 3-hydroxy-3-methyl-2-butanone, and 4-hydroxy-3-hexanone, with rate constants (in units of 10-12 cm3 molecule-1 s-1) of 7.7 ± 1.7, 10.3 ± 2.2, 8.1 ± 1.8, 16.2 ± 3.4, 0.94 ± 0.37, and 15.1 ± 3.1, respectively, where the error limits include the estimated overall uncertainty in the rate constant for the reference compound. Rate constants were also measured for reactions with NO3 radicals and O3. Rate constants for the NO3 radical reactions (in units of 10-16 cm3 molecule-1 s-1) were 1-hydroxy-2-butanone, 3 were observed, and upper limits to the rate constants of -19 cm3 molecule-1 s-1 were derived for all six hydroxycarbonyls. The dominant tropospheric loss process for the hydroxycarbonyls studied here is calculated to be by reaction with the OH radical.

-

Nodzu,Goto

, (1940)

-

Photo-oxidations of Acetoin and Biacetyl catalyzed by Tetrabutylammonium Decatungstate(4-) in Acetonitrile under Excess of Oxygen

Nomiya, Kenji,Maeda, Katsunori,Miyazaki, Toshiaki,Miwa, Makoto

, p. 961 - 962 (1987)

Under an excess of oxygen, the photo-oxidation of acetoin catalysed by (NBu4)4(W10O32) and based on irradiation (λ > 300 nm) of the charge-transfer band in acetonitrile solution has been investigated.After irradiating for 30 h the products were biacetyl and acetic acid.The acetic acid was produced from both the acetoin and biacetyl.The rate constant for each path was determined by computer simulation.The production of biacetylis based on dehydrogenation of acetoin in conjunction with the redox cycle of (W10O32)4- attained by reaction with O2, whereas the production of acetic acid from biacetyl is based on the photoexcitation of biacetyl complexed with (W10O32)4- and subsequent reactions with O2 and water.

-

Davis,Rogers,Thiel

, p. 558 (1939)

-

A study on the cataluminescence of propylene oxide on FeNi layered double hydroxides/graphene oxide

Li, Ming,Hu, Yufei,Li, Gongke

, p. 11823 - 11830 (2021/07/11)

In this work, FeNi layered double hydroxides/graphene oxide (FeNi LDH/GO) was prepared, which exhibits excellent selective cataluminescent performance towards propylene oxide. The selectivity and sensitivity of the cataluminescence (CTL) reaction were investigated in detail. Moreover, the catalytic reaction mechanism, including the intermediate products and the conversion of reactants to products, was discussed based on both the experimental and computational results. Furthermore, the proposed FeNi LDH/GO based CTL sensor was successfully applied for the determination of propylene oxide residue in fumigated raisins, which indicates extensive application potential for rapid food safety evaluation.

Bioinspired oxidation of oximes to nitric oxide with dioxygen by a nonheme iron(II) complex

Bhattacharya, Shrabanti,Lakshman, Triloke Ranjan,Sutradhar, Subhankar,Tiwari, Chandan Kumar,Paine, Tapan Kanti

, p. 3 - 11 (2019/11/11)

The ability of two iron(II) complexes, [(TpPh2)FeII(benzilate)] (1) and [(TpPh2)(FeII)2(NPP)3] (2) (TpPh2 = hydrotris(3,5-diphenylpyrazol-1-yl)borate, NPP-H = α-isonitrosopropiophenone), of a monoanionic facial N3 ligand in the O2-dependent oxidation of oximes is reported. The mononuclear complex 1 reacts with dioxygen to decarboxylate the iron-coordinated benzilate. The oximate-bridged dinuclear complex (2), which contains a high-spin (TpPh2)FeII unit and a low-spin iron(II)–oximate unit, activates dioxygen at the high-spin iron(II) center. Both the complexes exhibit the oxidative transformation of oximes to the corresponding carbonyl compounds with the incorporation of one oxygen atom from dioxygen. In the oxidation process, the oxime units are converted to nitric oxide (NO) or nitroxyl (HNO). The iron(II)–benzilate complex (1) reacts with oximes to afford HNO, whereas the iron(II)–oximate complex (2) generates NO. The results described here suggest that the oxidative transformation of oximes to NO/HNO follows different pathways depending upon the nature of co-ligand/reductant.

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