513-86-0

Basic information

• Product Name: 3-Hydroxy-2-butanone
• Synonyms: DIMETHYLKETOL;FEMA 2008;GAMMA-HYDROXY-BETA-OXOBUTANE;2,3-BUTANOLONE;ACETOIN;ACETYL METHYL CARBINOL;AMC;3-HYDROXYBUTAN-2-ONE
• CAS NO: 513-86-0
• Molecular Formula: C₄H₈O₂
• Molecular Weight: 88.11
• EINECS: 208-174-1
• Product Categories: Pharmaceutical Raw Materials;ketone;ketone Flavor;Other APIs
• Mol File: 513-86-0.mol

Chemical Properties

• Melting Point: 15 °C (monomer)
• Boiling Point: 148 °C(lit.)
• Flash Point: 123 °F
• Appearance: Pale yellow to green-yellow or white to yellow/Liquid (Monomer) or Powder or Crystals (Dimer)
• Density: 1.013 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.92mmHg at 25°C
• Refractive Index: n20/D 1.417(lit.)
• Storage Temp.: 2-8°C
• Solubility: H2O: 0.1 g/mL, clear
• PKA: 13.21±0.20(Predicted)
• Water Solubility: SOLUBLE
• Merck: 14,64
• BRN: 385636
• CAS DataBase Reference: 3-Hydroxy-2-butanone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxy-2-butanone(513-86-0)
• EPA Substance Registry System: 3-Hydroxy-2-butanone(513-86-0)

Safety Data

• Hazard Codes: Xi,F
• Statements: 10-36/38-38-11
• Safety Statements: 26-36-36/37
• RIDADR: UN 2621 3/PG 3
• WGK Germany: 1
• RTECS: EL8790000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 513-86-0(Hazardous Substances Data)

Usage

Uses

Used in Food Flavoring and Fragrances:
3-Hydroxy-2-butanone is used as an aroma carrier in the preparation of flavors and essences, particularly for butter, milk, yogurt, and strawberry flavors. It is also used as an intermediate of the butanediol cycle in microorganisms and is found in some fruits and vegetables, such as fresh apple, butter, cheddar cheese, coffee, cocoa, honey, wheat bread, and wine.
Used in Pharmaceutical Intermediates:
3-Hydroxy-2-butanone is used as a pharmaceutical intermediate, mainly for the preparation of cream, dairy, yogurt, and strawberry spices.
Taste and Aroma Characteristics:
At 10 ppm, 3-Hydroxy-2-butanone has a taste profile described as sweet, creamy, dairy, and butter-like. At 1.0%, its aroma characteristics are strong buttery and creamy.

Content analysis

It was determined by gas chromatography (GT-10). Use thermal conductivity detector. Use a column of 1.5 m (length), 6.35 mm (inner diameter). The column contains 20% polyethylene glycol 20M (Carbowax 20M) which is loaded on the 60/80 mesh diatomaceous earth carrier. Alternatively we can use other components that can separate diacetyl, water and methylacetyl alcohol. The following conditions were used: the sample was 2 μg; the injection temperature was about 195 ° C; the column temperature was about 130 ° C and the detector was about 230 ° C; the flow rate of the carrier gas was about 35 ml per minute. The average residence time: 2 min 15S for diacetyl, 3 min for water, and 12 mins for methyl acetyl alcohol. The peak area of the resulting methylacetyl alcohol shall not be less than 96.0% of the total area of all peaks.

As a flavor ingredient

Acetoin is a yellowish liquid with a bland, woody, yogurt odor and a fatty creamy “tub” butter taste. It is useful as a flavor ingredient in butter, milk, yogurt or strawberry flavors. Identification: ▼▲ CAS.No.:? 513-86-0? FL.No.:? 7.051 FEMA.No.:? 2008 NAS.No.:? 2008 CoE.No.:? 749 EINECS.No.:? 208-174-1? JECFA.No.:? 405 　 　 Regulatory Status: CoE: Approved. Bev.: 5 ppm; Food: 50 ppm FDA: 21 CFR 182.60, 184.1848, 582.60 FDA (other): n/a JECFA: ADI: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (1998). Reported uses (ppm): (FEMA, 1994) ▼▲ Food Category? Usual? Max.? Alcoholic.beverages? 3.1 3.1 Baked.goods? 380 750 Breakfast.cereals? 0.67 0.67 Cheese? 10 10 Chewing.gum? 0.42 0.42 Condiments,.relishes? 2 8 Confection,.frosting? 21 100 Fats,.oils? 50 750 Frozen.dairy? 10 50 Fruit.juice? 0.03 0.03 Gelatins,.puddings? 81 81 Gravies? 0.029 0.029 Hard.candy? 18.2 84.89 Imitation.dairy? 50 100 Meat.products? 12.29 24.27 Milk.products? 0.012 0.03 Nonalcoholic.beverages? 1.8 17 Other.grains? 200 400 Reconstituted.vegetables? 32 200 Seasoning,.flavors? 30 90 Snack.foods? 36 98 Soft.candy? 9.8 50 Soups? 0.05 0.05 Sweet.sauce? 98 98 Natural occurrence: Reported found in fresh apple, butter, cheddar cheese, coffee, cocoa, honey, wheat bread and wine.

Air & Water Reactions

Flammable. Slightly soluble in water.

Reactivity Profile

3-Hydroxy-2-butanone is a ketone and alcohol. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

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

Experimental reproductive effects. LWdly toxic by subcutaneous route. A moderate skin irritant. Flammable liquid. When heated to decomposition it emits acrid smoke and fumes. See also KETONES

Synthesis

From diacetyl by partial reduction with zinc and acid. It is also a product of fermentation. Acetoin is an optically active compound. The d(–)acetyl methyl carbinol is obtained from fermentation and, in mixture with other products, from the catalytic oxidation of 2,3-butanediol. The 1(+)acetyl methyl carbinol is also obtained from fermentation. The optically pure form has not been isolated; the optically inactive form is prepared synthetically

Purification Methods

Wash acetoin with EtOH until colourless, then with diethyl ether or acetone to remove biacetyl. Dry it in air by suction and dry further in a vacuum desiccator. [Beilstein 1 IV 3991.]

InChI:InChI=1/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3/t3-/m0/s1

Upstream product

• 50-00-0 formaldehyd 
• 849585-22-4 LACTIC ACID 
• 64-17-5 ethanol 
• 1029272-42-1 (2R,3S)-2,3-butanediol 
• 24347-58-8 (R,R)-2,3-butandiol 
• 473-81-4 glyceric acid 
• 69-65-8 mannitol 
• 14088-58-5 3-diazo-2-butanone 
• 918-44-5 alpha-acetyllactic acid 
• 75-07-0 acetaldehyde 
• 127-17-3 2-oxo-propionic acid 
• 141-78-6 ethyl acetate 
• 616-27-3 1-chlorobutan-2-one 
• 2835-06-5 phenylglycin 

Downstream Products

• 42479-40-3 biacetyl bis(N-methyl-N-phenylhydrazone) 
• 2861-48-5 butane-2,3-dione-bis-phenylhydrazone 
• 1245-13-2 2,2'-biquinoline-4,4'-dicarboxylic acid 
• 2302-39-8 4,5-dimethylimidazole 
• 513-85-9 2.3-butanediol 
• 4906-24-5 3-acetoxy-2-butanone 
• 40722-10-9 N,N'-bis(cyclohexyl)-2,3-butanediimine 
• 13682-20-7 4,5-dimethyl-2-phenyl-1H-imidazole 
• 117668-70-9 3-(p-tolylamino)butan-2-one 
• 2199-54-4 2,4,5-trimethyl-3-ethoxycarbonylpyrrole 
• 21478-63-7 benzoic acid 1-methyl-2-oxo-propyl ester 
• 822-90-2 2,4,5-trimethyl-1H-imidazole 
• 101258-83-7 3-Butylamino-butanon-(2) 
• 94622-67-0 butane-2,3-dione-bis-(4-nitro-phenylhydrazone) 

Relevant articles and documents

Vapor-phase catalytic dehydration of 2,3-butanediol to 3-buten-2-ol over ZrO2 modified with alkaline earth metal oxides

Vapor-phase catalytic dehydration of 2,3-butanediol (2,3-BDO) to produce 3-buten-2-ol (3B2OL) was investigated over several monoclinic ZrO2 (m-ZrO2) catalysts modified with alkaline earth metal oxides (MOs), such as SrO, BaO, and MgO, to compare with the previously reported CaO/m-ZrO2. It was found that these modifiers enhanced the 3B2OL formation to the same level as CaO did by loading an appropriate MO content. Among all the tested catalysts, the BaO/m-ZrO2 calcined at 800?°C with a low BaO content (molar ratio of BaO/ZrO2?=?0.0452) shows the highest 2,3-BDO conversion (72.4%) and 3B2OL selectivity (74.4%) in the initial stage of 5?h at 350?°C. In order to characterize those catalysts, their catalytic activities, crystal structures, and basic properties were studied in detail. In X-ray diffraction (XRD) and X-ray photoelectron spectroscopy (XPS) experiment, it was elucidated that highly dispersed M-O-Zr (M?=?Ca, Sr, and Ba) hetero-linkages were formed on the surface by loading these MOs onto m-ZrO2 with an appropriate content and then calcining at 800?°C. It can be concluded that the M-O-Zr hetero-linkages generate the proper base-acid balance for the efficient formation of 3B2OL from 2,3-BDO.

Synthesis of quadruply carbon-13 labeled tetramethyltetrathiafulvalene

A short synthesis of tetramethyltetrathiafulvalene quadruply labeled with carbon-13 is described.

Kinetics and Mechanisms of Oxidations by Metal Ions. V. Oxidation of 4-Oxopentanoic Acid by the Aquavanadium(V) Ion

The outer sphere oxidation of 4-oxopentanoic acid (4-OPA), studied at 50 deg C by aquavanadium (V) ion, is H(1+)-catalyzed reaction.The reaction has a first-order dependence on each of , , and .The H(1+) catalysis can not be ascribed to keto enol equilibrium because of the knowledge that a γ-keto acid is the least enolized amongst keto acids.Hence V(OH)3(2+)(aq) ion is the active oxidant.The proposed mechanism, assumed to involve the initial decarboxylation, is supported by the spot test characterization of acetoin as the intermediate oxidation product.Acetoin is further oxidized to two moles of acetic acid which is the final oxidation product.The overall energy of activation (ΔH1=26+/-3 kJ mol-1) is lower than the normal value (84 kJ mol-1) and therefore the highly negative value of the overall entropy of activation (ΔS1=-268+/-8 JK-1 mol-1) is considered to be responsible for the observed slowrate of oxidation.

Influence of Br- Concentration on (Br)+-Mediated Indirect Electrooxidation of Alcohols to the Corresponding Carbonyl Compounds

Current efficiency for the (Br)+ (positive bromine species)-mediated indirect electrooxidation of alcohols to the corresponding carbonyl compounds decreased with increase in Br- concentration in dichloromethane and aqueous acidic solutions, while no concentration dependence was observed in an aqueous neutral solution.These facts suggested a general practical guideline for the indirect electrooxidation, i.e. low Br- concentration is favorable in an electrolytic solution of low nucleophilicity.It was also found that the kind of (Br)+ species formed anodically in the absence of the alcohols in dichloromethane celarly depended on charge(Q) passed as follows:Br3- at Q-1 (1F = 96480 C), Brn- (n>3) at 2/3-1, and Br2 at Q = 1F mol-1.Among these species, Br3- and Br2 seemed to be the weakest and strongest oxidizing agents, respectively.Lower efficiency for the direct electrooxidation in higher Br- concentration was rationalized as due to more predominant formation of Br3- and/or Brn- with smaller n values.

Influence of Calcium Ions on the Mechanism of Oxime Formation from Acetoin

The effect of calcium ions on the reaction of acetoin with hydroxylamine was studied. This reaction proceeds by a two-step mechanism: the attack of hydroxylamine on the carbonyl compound to give a tetrahedral addition intermediate, and the dehydration of this intermediate to form the oxime. The presence of calcium ions decreases the value of the equilibrium constant of the tetrahedral addition intermediate formation, but increases the overall rate constant of the reaction when dehydration is the rate-determining step. Evidence suggests that the effect of calcium ions is through the formation of a complex with the hydroxyl groups of the tetrahedral addition intermediate, facilitating the dehydration step of the reaction.

A highly efficient thiazolylidene catalyzed acetoin formation: Reaction, tolerance and catalyst recycling

An efficient formation of acetoin from acetaldehyde was achieved under thiazolylidene catalysis. High yields and TON were achieved. Its sufficient tolerance toward ethanol and moisture renders it a practical key step of the ethanol upgrading process. A new type of solid supported thiazolylidene catalyst was designed to make catalyst recycling achievable. This journal is

New Enantioselective Reactions catalysed by Cinchonidine-modified Platinum

The conjugated diketones butane-2,3-dione and hexane-3,4-dione can be hydrogenated enantioselectively over Pt/silica modified by cinchonidine giving enantiomeric excesses in favour of (R)-(-)-3-hydroxybutan-2-one of up to 38percent and of (R)-(-)-4-hydroxyhexan-3-one up to 33percent.

Practical tethering of vitamin B1 on a silica surface via its phosphate group and evaluation of its activity

A convenient immobilization of thiamine pyrophosphate molecules on a silica surface through the phosphate group is developed, leading to a very active heterogenised biocatalyst for pyruvate decarboxylation.

Selective hydrogenation by novel composite supported Pd egg-shell catalysts

Two organic-inorganic mixed phase supports were prepared, comprising an alumina filler and polymers of different chemical nature. Four low loaded Pd catalysts were prepared. Good activities and selectivities were obtained during the hydrogenations of styrene, 1-heptyne and 2,3-butanedione. The catalysts were found to have excellent mechanical properties and could be used in applications needing high attrition resistance and crushing strength. In this sense, processes for fine chemicals using slurry reactors or processes for commodities using long packed beds could advantageously use them.

Vapor-phase catalytic dehydration of 2,3-butanediol into 3-buten-2-ol over Sc2O3

Vapor-phase catalytic dehydration of 2,3-butanediol (2,3-BDO) was investigated over rare earth oxide (REO) catalysts as well as In2O3. In the dehydration of 2,3-BDO, 3-buten-2-ol (3B2OL) was produced together with 3-hydroxy-2-butanone (3H2BO), butanone (MEK), 2-methylpropanal (IBA), 2-methyl-1-propanol (IBO), etc. Sc2O3 and In2O3 showed hi gher 3B2OL select ivities than other REOs. In particular, Sc2O3 converted 2,3-BDO into 3B2OL with an excellent selectivity of 85.0% at 99.9% conversion.