600-14-6

Basic information

• Product Name: 2,3-Pentanedione
• Synonyms: 2,3-Pentadione;2,3-pentandione;Acethylpropionyl;CH3C(O)C(O)C2H5;2,3-PENTANEDITHIOL;2 3-PENTANEDIONE 96+% FCC;2,3-PENTANEDIONE 97%;2,3-PENTANEDIONE FEMA NO.2841
• CAS NO: 600-14-6
• Molecular Formula: C₅H₈O₂
• Molecular Weight: 100.12
• EINECS: 209-984-8
• Product Categories: Pharmaceutical Raw Materials;Organics;ketone Flavor
• Mol File: 600-14-6.mol
• Article Data: 46

Chemical Properties

• Melting Point: -52 °C
• Boiling Point: 110-112 °C(lit.)
• Flash Point: 66 °F
• Appearance: very deep green-yellow/Liquid
• Density: 0.958
• Vapor Pressure: 28.5 hPa (20 °C)
• Refractive Index: n20/D 1.404(lit.)
• Storage Temp.: 2-8°C
• Solubility: 60g/l
• Explosive Limit: 1.8-10.9%(V)
• Water Solubility: 60 g/L (15 ºC)
• Stability: Stable. Highly flammable - store cool. Incompatible with strong oxidizing agents, reducing agents, strong bases.
• BRN: 1699638
• CAS DataBase Reference: 2,3-Pentanedione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Pentanedione(600-14-6)
• EPA Substance Registry System: 2,3-Pentanedione(600-14-6)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36-37/39
• RIDADR: UN 1224 3/PG 2
• WGK Germany: 1
• RTECS: SA1850000
• F: 9-23
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 600-14-6(Hazardous Substances Data)

Usage

Chemical Properties

2,3-Pentanedione is a colourless or deep green-yellow colour liquid that has a somewhat sweet odor similar to quinone. This compound has a penetrating, buttery taste on dilution. It is used as flavoring agent or adjuvant.

Occurrence

2,3-Pentanedione occurs in butter, bread, milk, yogurt, chicken, meat, cocoa, coffee, potato chips, roasted almonds, pecans, beer, red and white wine, rum and whiskey. The organoleptic profile can be described as creamy, penetrating, cheesy, oily, sweet, buttery, almondlike, brown roasted, and somewhat caramellic, with a fruity nuance.

Uses

2,3-Pentanedione may be used as a reference standard in the determination of 2,3-pentanedione in beer samples using headspace-gas chromatographic technique (HS-GC).

Application

2,3-Pentanedione can be used as a reactant to synthesize:Bisphenol derivatives by acid-catalyzed condensation reaction with phenols.2-Ethyl-3-methyl-1H-indole by Pd-catalyzed reaction with aniline under reductive conditions.2-Ethyl-3-methylquinoxaline by condensation reaction with o-phenylenediamine using citric acid as a catalyst.

Definition

ChEBI: 2,3-Pentanedione is an alpha-diketone that is pentane substituted at the 2- and 3-positions by oxo groups. It has a role as a flavouring agent. It is an alpha-diketone and a methyl ketone. It derives from a hydride of a pentane.

Preparation

By oxidation of methyl propyl ketone with excess NaNO2 and diluted HCl in the presence of hydroxylamine hydrochloride under a nitrogen blanket.

Aroma threshold values

Detection: 20 ppb. Aroma characteristics at 1.0%: buttery diacetyl-like, fermented dairy and creamy, popcorn buttery.

Taste threshold values

Taste characteristics at 1 to 5 ppm: sweet buttery, creamy, cheesy, slightly toasted dairy, with a rich baked goods nuance and a good mouthfeel.

General Description

2,3-Pentanedione (acetylpropionyl) is one of the aroma active compounds of cereal coffee brew.

Biochem/physiol Actions

Taste at 1-5.0 ppm

Safety Profile

Confirmed human carcinogen. Poison by intraperitoneal route. When heated to decomposition it emits acrid smoke and irritating fumes. See also NICKEL COMPOUNDS

InChI:InChI=1/C5H8O2/c1-3-5(7)4(2)6/h3H2,1-2H3

Synthetic route

CpRe(CO)2(COCH3)(CH3) + 3,4-hexanedione (4437-51-8) → tricarbonylcyclopentadienylrhenium + 2,3-Pentanedione (600-14-6) + dimethylglyoxal (431-03-8) + acetone (67-64-1)

Conditions	Yield
With CO In benzene-d6 Irradiation (UV/VIS); 355-385 nm;;	A 100% B 68% C 34% D 10%

LACTIC ACID (849585-22-4) → 2,3-Pentanedione (600-14-6)

Conditions	Yield
With aluminum oxide; potassium fluoride at 200℃; Reagent/catalyst;	81.5%
trockne Destillation des Zinksalzes;
With caesium supported on porous carrier at 260℃; Catalytic behavior; Temperature; Sealed tube;

1-(2-ethyl-1,3-dithian-2-yl)ethanone (129650-81-3) → 2,3-Pentanedione (600-14-6)

Conditions	Yield
In water; acetonitrile electrolysis; Pt-electrode;	80%

3,4-epoxy-2-pentanone (17257-79-3) → 2,3-Pentanedione (600-14-6)

Conditions	Yield
With titanium(IV) dichlorodiisopropylate In diethyl ether for 3h; Ambient temperature;	75%

LACTIC ACID (849585-22-4) → 2,3-Pentanedione (600-14-6) + acetaldehyde (75-07-0) + propionic acid (802294-64-0) + acrylic acid (79-10-7)

Conditions	Yield
With 12% Na2HPO4-modified NaY-20.1 (H2O/SiO2 molar ratio) In water at 340℃; for 2h; Catalytic behavior; Reagent/catalyst; Temperature;	A 5.2% B 5.1% C 1% D 74.3%
With NaY-20.1 (H2O/SiO2 molar ratio) In water at 340℃; for 2h; Catalytic behavior; Reagent/catalyst; Temperature;	A 2.5% B 13.6% C 1.1% D 42%
With calcium phosphate hydroxyapatite; ammonia; sodium hydroxide In water at 349.84℃; for 6h; Inert atmosphere;

3-chloro-3-(ethylthio)-2-pentanone (303186-51-8) → 2,3-Pentanedione (600-14-6)

Conditions	Yield
With water; mercury dichloride In dichloromethane at 20℃; for 20h; Hydrolysis;	73%
Multi-step reaction with 2 steps 1: 91 percent / sodium carbonate / 15 h / 20 °C 2: 57 percent / H2O; HgCl2 / CH2Cl2 / 3 h / Heating View Scheme

2-chloro-2-(ethylthio)-3-pentanone (303186-52-9) → 2,3-Pentanedione (600-14-6)

Conditions	Yield
With water; mercury dichloride In dichloromethane at 20℃; for 20h; Hydrolysis;	73%
Multi-step reaction with 2 steps 1: 97 percent / sodium carbonate / 15 h / 20 °C 2: 60 percent / H2O; HgCl2 / CH2Cl2 / 3 h / Heating View Scheme

LACTIC ACID (849585-22-4) → 2,3-Pentanedione (600-14-6) + acetaldehyde (75-07-0) + acetic acid (64-19-7) + propionic acid (802294-64-0) + acrylic acid (79-10-7)

Conditions	Yield
Stage #1: LACTIC ACID With Cs-doped hydroxyapatite In water at 300℃; under 760.051 Torr; Inert atmosphere; Stage #2: at 400℃; Reagent/catalyst; Calcination;	A 72.3% B n/a C n/a D n/a E n/a
With Mg0388Al2408O4 at 380℃; under 760.051 Torr; pH=7 - 8; Reagent/catalyst; Concentration; Gas phase;
With KNO3/TiPO (5:1) In water at 270℃; Catalytic behavior; Kinetics; Concentration; Reagent/catalyst; Temperature; Flow reactor;

2-(ethylthio)-2-methoxy-3-pentanone (303186-57-4) → 2,3-Pentanedione (600-14-6)

Conditions	Yield
With water; mercury dichloride In dichloromethane for 3h; Hydrolysis; Heating;	60%

D-Lactic acid (10326-41-7) → 2,3-Pentanedione (600-14-6) + acetaldehyde (75-07-0) + acrylic acid (79-10-7)

Conditions	Yield
With Cs and Na exchanged beta zeolite at 360℃; for 2h; Reagent/catalyst;	A n/a B n/a C 60%
With Cs and Na exchanged beta zeolite at 360℃; for 2h; Reagent/catalyst;	A n/a B n/a C 46%

acetic anhydride (108-24-7) + propionaldehyde (123-38-6) → 2,3-Pentanedione (600-14-6) + 3,4-hexanedione (4437-51-8)

Conditions	Yield
cobalt(II) chloride In acetonitrile at 20℃; for 24h;	A 58% B 23%
With oxygen; CoCl2 In acetonitrile for 15h; Mechanism; other solvents; other aliphatic and aromatic aldehydes;

propionaldehyde (123-38-6) → 2,3-Pentanedione (600-14-6) + 3,4-hexanedione (4437-51-8)

Conditions	Yield
With acetic anhydride; cobalt(II) chloride In acetonitrile at 20℃; for 24h;	A 58% B 23%

3-(ethylthio)-3-methoxy-2-pentanone (303186-56-3) → 2,3-Pentanedione (600-14-6)

Conditions	Yield
With water; mercury dichloride In dichloromethane for 3h; Hydrolysis; Heating;	57%

acetaldehyde (75-07-0) + propionaldehyde (123-38-6) → 2,3-Pentanedione (600-14-6)

Conditions	Yield
Stage #1: acetaldehyde; propionaldehyde With 3-ethyl-4-methyl-5-hydroxyethylthiazolium chloride; sodium hydrogencarbonate at 120℃; for 3.5h; pH=9 - 10; Autoclave; Stage #2: With ozone; acetic acid at 10℃; Temperature;	51.6%
Stage #1: acetaldehyde; propionaldehyde With 3-ethyl 4-methyl-5-hydroxyethylthiazole chloride; sodium hydrogencarbonate at 120℃; for 3.5h; pH=9 - 10; Stage #2: With ozone; acetic acid In water at 10℃; Temperature;

D-Lactic acid (10326-41-7) → 2,3-Pentanedione (600-14-6) + acetaldehyde (75-07-0) + propionic acid (802294-64-0) + acrylic acid (79-10-7)

Conditions	Yield
With Cs beta zeolite at 360℃; for 10h;	A n/a B n/a C n/a D 44%

1,2,3,4,5-pentahydroxy-pentane (87-99-0, 488-81-3, 488-82-4, 2152-56-9, 6917-36-8, 7643-75-6) → furan (110-00-9) + 2,3-Pentanedione (600-14-6) + acetaldehyde (75-07-0) + Glycolaldehyde (141-46-8) + 1-Hydroxy-2-butanone (5077-67-8) + hydroxy-2-propanone (116-09-6)

Conditions	Yield
at 358℃; for 0.000833333h; Product distribution; Curie-point pyrolysis;	A 3.5% B 2.6% C 7.1% D 16.4% E 11.6% F 25.9%

dimethylsulfide (75-18-3) + 2-(dimethylaminomethylene)pentan-3-one (81609-25-8) → 2,3-Pentanedione (600-14-6)

Conditions	Yield
With ozone In methanol	19%

LACTIC ACID (849585-22-4) → 2,3-Pentanedione (600-14-6) + carbon monoxide (201230-82-2) + acetaldehyde (75-07-0) + propionic acid (802294-64-0) + hydroxy-2-propanone (116-09-6) + acrylic acid (79-10-7)

Conditions	Yield
sodium nitrate; silica gel; sodium lactate at 315℃; under 4500.4 Torr; for 2.2h; Product distribution; Rate constant; Thermodynamic data; ΔE(excit.); var. temp. and time;	A 14% B 9.1% C 12.5% D 1.6% E 3.1% F 7.8%

LACTIC ACID (849585-22-4) → 2,3-Pentanedione (600-14-6) + ethanol (64-17-5) + acetaldehyde (75-07-0) + propionic acid (802294-64-0) + hydroxy-2-propanone (116-09-6) + acrylic acid (79-10-7)

Conditions	Yield
With aluminum oxide; silica gel; sodium phosphate at 300℃; under 3750.3 Torr; Product distribution; Thermodynamic data; Equilibrium constant; mechanism, var. sodium phosphate salts, temp. and contact times;	A 4.3% B n/a C 1.9% D 0.9% E 0.6% F 2%

3-penten-2-one (625-33-2) → 2,3-Pentanedione (600-14-6)

Conditions	Yield
With piperidine; diethyl ether; bromine Behandlung der von Piperidinhydrobromid befreiten Reaktionsgemische mit 10prozentiger Schwefelsaeure;

2-pentanol (584-02-1) → 2,3-Pentanedione (600-14-6) + 1,1-dinitroethane (600-40-8)

Conditions	Yield
With nitric acid

4-penten-3-one (1629-58-9) → 2,3-Pentanedione (600-14-6)

Conditions	Yield
With piperidine; diethyl ether; bromine Behandlung der von Piperidinhydrobromid befreiten Reaktionsgemische mit 10prozentiger Schwefelsaeure;

1-penten-4-yne-3-ol (14304-27-9) → 2,3-Pentanedione (600-14-6)

Conditions	Yield
With sulfuric acid; mercury(II) sulfate

2-hydroxy-3-pentanone (5704-20-1) → 2,3-Pentanedione (600-14-6)

Conditions	Yield
With copper at 250℃;

(E)-3-bromo-3-penten-2-one (65304-44-1) + potassium acetate (127-08-2) → 2,3-Pentanedione (600-14-6)

Conditions	Yield
durch nachfolgende Verseifung des Produkts mit Schwefelsaeure;

3-Hydroxy-2-pentanone (3142-66-3) → 2,3-Pentanedione (600-14-6)

Conditions	Yield
mit Oxydationsmittel;

2-ethoxy-pent-1-en-3-one (710327-87-0) → 2,3-Pentanedione (600-14-6)

Conditions	Yield
With hydrogenchloride

3,3-diethoxy-pentan-2-one (34451-09-7) → 2,3-Pentanedione (600-14-6)

Conditions	Yield
With hydrogenchloride

3-nitro-3-nitroso-pentan-2-one → 2,3-Pentanedione (600-14-6)

Conditions	Yield
durch Erhitzen;

2,3-Pentanedione (600-14-6) + Methoxytrimethylsilane (1825-61-2) + trans-1,2-cyclohexandiol (1460-57-7) → (2R,3R,4aS,8aS)-2-Ethyl-2,3-dimethoxy-3-methyl-octahydro-benzo[1,4]dioxine

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 3h;	97%

2,3-Pentanedione (600-14-6) → 2-hydroxy-2-methylcyclobutan-1-one (25733-27-1)

Conditions	Yield
With acetone for 1.1h; Flow reactor; UV-irradiation; Green chemistry;	96%
In acetonitrile at 25℃; Schlenk technique; Inert atmosphere; Irradiation;	95%
In benzene Irradiation;
Multi-step reaction with 2 steps 1.1: ethyl acetate / 30 h / Irradiation; Inert atmosphere 1.2: Inert atmosphere 2.1: sodium methylate / methanol / 2 h / 20 °C View Scheme

2,3-Pentanedione (600-14-6) + 1,2-diamino-benzene (95-54-5) → 2-ethyl-3-methylquinoxaline (37920-99-3)

Conditions	Yield
In water at 20℃; for 0.5h; Green chemistry;	95%
With ammonium chloride In methanol at 20℃; for 1h; Inert atmosphere;	94%
With poly(ethylene glycol)-600 In water at 20℃; for 0.0833333h;	89%

2,3-Pentanedione (600-14-6) + trans-1,2-Diaminocyclohexane (1121-22-8, 1436-59-5, 20439-47-8, 21436-03-3, 41013-43-8, 694-83-7) → 2-ethyl-3-methyl-4a,5,6,7,8,8a-hexahydroquinoxaline

Conditions	Yield
In water at 20℃; for 0.5h; Green chemistry;	95%

2,3-Pentanedione (600-14-6) + 4-nitro-benzoyl chloride (122-04-3) → (Z)-3-(p-nitrobenzoyloxy)-3-penten-2-one (179804-03-6)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; triethylamine In tetrahydrofuran at 20℃; for 36h;	94%

2,3-Pentanedione (600-14-6) + ethylenediamine (107-15-3) → 2-methyl-3-ethylpyrazine (15707-23-0)

Conditions	Yield
Stage #1: 2,3-Pentanedione; ethylenediamine In ethanol at -5 - 70℃; for 7h; Stage #2: With potassium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene at 30 - 70℃; for 5h; Time;	93.5%

chloro-trimethyl-silane (75-77-4) + 2,3-Pentanedione (600-14-6) → 2,3-bis(trimethylsilyloxy)-1,3-pentadiene

Conditions	Yield
With triethylamine; lithium bromide In tetrahydrofuran	93%

2,3-Pentanedione (600-14-6) → 1,4-dibromo-2,3-pentanedione (21619-26-1)

Conditions	Yield
With sodium bromate; hydrogen bromide In chloroform at 25 - 35℃; for 11.5h;	92%
With bromine
With bromine at 20℃; for 1.5h;
With bromine for 1.5h;

2,3-Pentanedione (600-14-6) + Norpseudoephedrine (37577-07-4) → (2S,5R,6R)-2-hydroxy-5,6-dihydro-2-ethyl-3,5-dimethyl-6-phenyl-2H-1,4-oxazine

Conditions	Yield
In diethyl ether at 0℃; for 0.5h;	91%

2,3-Pentanedione (600-14-6) + 4,5-dimethyl-1,2-phenylenediamine (3171-45-7) → 2-ethyl-3,6,7-trimethylquinoxaline (1350827-61-0)

Conditions	Yield
With ammonium chloride In methanol at 20℃; for 1h; Inert atmosphere;	91%

2,3-Pentanedione (600-14-6) + 4-methylthiosemicarbazide (6610-29-3) → 2,3-pentanedione bis(4-methyl-3-thiosemicarbazone)

Conditions	Yield
With acetic acid In ethanol Reflux;	91%
Stage #1: 2,3-Pentanedione With hydrogenchloride In methanol at 20℃; Stage #2: 4-methylthiosemicarbazide With hydrogenchloride In methanol at 20℃; for 72h;

2,3-Pentanedione (600-14-6) + (1R,2S)-norephedrine (492-41-1) → (2S,5S,6R)-2-hydroxy-5,6-dihydro-2-ethyl-3,5-dimethyl-6-phenyl-2H-1,4-oxazine

Conditions	Yield
In diethyl ether at 0℃; for 0.5h;	90%

2,3-Pentanedione (600-14-6) + (R)-Phenylglycinol (56613-80-0) → (2S,5R)-2-hydroxy-5,6-dihydro-2-ethyl-3-methyl-5-phenyl-2H-1,4-oxazine

Conditions	Yield
In tetrahydrofuran at 20℃; for 24h; Cyclization;	90%

2,3-Pentanedione (600-14-6) + N-ethylthiosemicarbazide (13431-34-0) → 2,3-pentanedione bis(4-ethylthiosemicarbazone)

Conditions	Yield
With acetic acid at 20℃;	90%

2,3-Pentanedione (600-14-6) + acetic anhydride (108-24-7) → 4-oxopent-2-en-3-yl acetate (50625-84-8)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 65℃; for 48h;	90%

2,3-Pentanedione (600-14-6) + triisopropyl(prop-1-en-2-yloxy)silane (153645-78-4) → (S)-4-hydroxy-4-methyl-6-triisopropylsilanyloxy-hept-6-en-3-one (1379680-61-1)

Conditions	Yield
With silver hexafluoroantimonate; Pd((R)-2,2'-bis(diphenylphosphino)-4,4'-Me-biphenyl)Cl2 In dichloromethane at -78℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	89%

2,3-Pentanedione (600-14-6) + 2-Amino-5-chlorobenzophenone (719-59-5) → 6-chloro-4-phenyl-2-propanoylquinoline

Conditions	Yield
With indium(III) triflate; 1-butyl-3-methylimidazolium Tetrafluoroborate at 100℃; for 2h; Friedlaender Quinoline Synthesis; Ionic liquid;	89%

2,3-Pentanedione (600-14-6) + 2-(trimethylsilyl)methylallyl iodide (80121-73-9) → (1S,2R)-1-Ethyl-2-methyl-4-methylene-cyclopentane-1,2-diol

Conditions	Yield
With stannous fluoride In tetrahydrofuran Ambient temperature;	88%

2,3-Pentanedione (600-14-6) + 2,4,6-trimethylaniline (88-05-1) → C23H30N2 (202405-42-3)

Conditions	Yield
In ethanol; water at 25℃; Inert atmosphere;	88%

2,3-Pentanedione (600-14-6) + (Z)-1-(tert-butylthio)-1-trimethylsilyloxyprop-1-ene (76943-94-7) → (2S,3S)-tert-butyl 2,3-dimethyl-3-hydroxy-4-oxohexanethioate

Conditions	Yield
With (S,S)-Cu(II) complex from bis(oxazolinyl) ligand and Cu(OTf)2 In dichloromethane at -78℃;	85%
Multi-step reaction with 2 steps 1: C48H40P2Pd(2+)*2F6Sb(1-) / dichloromethane / 3 h / -78 °C 2: hydrogenchloride; water / tetrahydrofuran / 2 h / 20 °C View Scheme

2,3-Pentanedione (600-14-6) + aniline (62-53-3) → (E)-2-(phenylimino)pentan-3-one (1058163-18-0)

Conditions	Yield
In methanol at 20℃; for 12h; Inert atmosphere;	85%

2,3-Pentanedione (600-14-6) + triisopropyl(prop-1-en-2-yloxy)silane (153645-78-4) → C17H34O3Si (959129-11-4)

Conditions	Yield
With silver hexafluoroantimonate; PdCl2[(S)-SEGPHOS] In dichloromethane at -78℃; for 18h;	84%

2,3-Pentanedione (600-14-6) + (2-amino-5-chloro-phenyl)-(2-chloro-phenyl)-methanone (2958-36-3) → 6-chloro-4-(2'-chlorophenyl)-2-propanoylquinoline

Conditions	Yield
With indium(III) triflate; 1-butyl-3-methylimidazolium Tetrafluoroborate at 100℃; for 2h; Friedlaender Quinoline Synthesis; Ionic liquid;	84%

2,3-Pentanedione (600-14-6) + 2,3-diaminomaleonitrile (18514-52-8) → 2-ethyl-3-methyl-5,6-di(1H-tetrazol-5-yl)pyrazine (119298-81-6)

Conditions	Yield
Stage #1: 2,3-Pentanedione; 2,3-diaminomaleonitrile With sodium azide In dimethyl sulfoxide at 100℃; for 3h; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide	83%

2,3-Pentanedione (600-14-6) + thiosemicarbazide (79-19-6) → 2,3-pentanedione bis(thiosemicarbazone) (18667-57-7)

Conditions	Yield
With acetic acid In ethanol Reflux;	82.8%
With hydrogenchloride In methanol; water at 20℃; for 72h;	4.5 g
Stage #1: 2,3-Pentanedione With hydrogenchloride In methanol at 20℃; Stage #2: thiosemicarbazide With hydrogenchloride In methanol at 20℃; for 72h;

2,3-Pentanedione (600-14-6) → 2,2,3,3-Tetrafluoro-pentane (83225-47-2)

Conditions	Yield
With sulfur tetrafluoride; hydrogen fluoride at 15℃; for 2h; in an autoclave;	82%

2,3-Pentanedione (600-14-6) + cobalt(II) thiocyanate (3017-60-5) + ethylenediamine (107-15-3) → Co(CH3CCCH2CH3N2CH2CH2)2(NCS)2 (915946-36-0)

Conditions	Yield
With LiOH In ethanol hot EtOH soln. of metal salt mixed with hot EtOH soln. of ethylenediamine, EtOH soln. of 2,3-pentanedione and LiOH added with stirring, refluxedfor 8 h, cooled; ppt. filtered, washed with EtOH, dried under vac. over P4O10; elem. anal.;	82%

2,3-Pentanedione (600-14-6) + ethylenediamine (107-15-3) + copper dichloride → Cu(CH3C2CH2CH3N2CH2CH2)2(2+)*2Cl(1-)=Cu(CH3CCCH2CH3N2CH2CH2)2Cl2

Conditions	Yield
With LiOH In ethanol hot EtOH soln. of metal salt mixed with hot EtOH soln. of ethylenediamine, EtOH soln. of 2,3-pentanedione and LiOH added with stirring, refluxedfor 8 h, cooled; ppt. filtered, washed with EtOH, dried under vac. over P4O10; elem. anal.;	82%

Upstream product

• 849585-22-4 LACTIC ACID 
• 625-33-2 3-penten-2-one 
• 584-02-1 2-pentanol 
• 1629-58-9 4-penten-3-one 
• 14304-27-9 1-penten-4-yne-3-ol 
• 34451-09-7 3,3-diethoxy-pentan-2-one 
• 716347-22-7 4-ethyl-3-methyl-hex-1-yne-3,4-diol 
• 1600-27-7 mercury(II) diacetate 
• 64-19-7 acetic acid 
• 609-29-0 pentane-2,3-dione 3-oxime 
• 76216-43-8 3-ethyl-2,4-pentanedione 
• 54001-61-5 5-Methyl-2,2,5-triethyl-2H-imidazole 
• 5436-14-6 3-ethyl-furan-2,4-dione 
• 7664-93-9 sulfuric acid 

Downstream Products

• 37711-21-0 pentane-2,3-dione-2-phenylhydrazone 
• 3896-13-7 pentane-2,3-dione-bis-phenylhydrazone 
• 42027-23-6 2,3-pentanediol 
• 3142-66-3 3-Hydroxy-2-pentanone 
• 18667-57-7 pentane-2,3-dione-bis thiosemicarbazone 
• 527-17-3 Duroquinone 
• 1180-59-2 2,3-pentadione bis(2,4-dinitrophenylhydrazone) 
• 56424-49-8 2-(N-methyl-anilino)-pentan-3-one 
• 21619-25-0 4-bromopentane-2,3-dione 
• 540-88-5 acetic acid tert-butyl ester 
• 107-71-1 tert-butyl peroxyacetate 
• 20487-40-5 tert-butyl propionate 
• 14206-05-4 tert-butyl peroxy propionate 
• 75-65-0 tert-butyl alcohol 

Relevant articles and documents

MECHANISM OF OXIDATION OF SOME ALIPHATIC KETONES BY N-BROMOSUCCINIMIDE IN ACIDIC MEDIA

Kinetics of the oxidation of methyl n-propyl ketone and methyl isobutyl ketone by N-bromosuccinimide (NBS) have been studied in perchloric acid media in presence of mercuric acetate.A zero order dependence to N-bromosuccinimide and a first order dependence to both ketones and hydrogen ion concentrations have been observed.Sodium perchlorate, mercuric acetate and succinimide additions have negligible effect while methanol addition has a positive effect on the reaction rate.A solvent isotope effect (k0D2O/K0H2O=2.3-2.7 and 2.4-2.8 for MeCOn.pr and MeCOi-Bu, respectively) has been observed at 35 deg.Kinetic investigations have revealedthat the order of reactivity is methyl n-propyl ketone>methyl isobutyl ketone.Various thermodinamic parameters have been computed and corresponding 1,2-diketones were found to be the products.A suitable mechanism in conformity with the above observations has been proposed.

An efficient and durable hierarchically porous KLA/TiPO catalyst for vapor phase condensation of lactic acid to 2,3-pentanedione

Sustainable production of 2,3-pentanedione from bio-lactic acid via a vapor condensation reaction over KLA/TiPO (KLA: potassium lactate) was investigated in this work. A KNO3 precursor supported on the surface of TiPO was in situ converted to basic sites in a KLA/TiPO catalyst. KLA together with Ti4+(Lewis acidic site) make up the acid-base pairs in the KLA/TiPO catalyst, resulting in excellent activity for the condensation of lactic acid to 2,3-pentanedione. The loading amount of KNO3 was shown to have an important influence on the catalytic performance, since the acid-base properties of the catalysts were found to vary with the addition of KNO3. Reaction conditions such as lactic acid feed flow rate and lactic acid concentration were also discussed. Both lactic acid conversion and 2,3-pentanedione selectivity increased with elevated lactic acid feed flow rates, indicating the existence of an external diffusion resistance of the lactic acid reactant during the catalytic reactions. However, the lactic acid feed flow rate increased to 1.0 mL h?1 (corresponding to LA liquid hourly space velocity (LHSV) = 2.6 H?1), and the external diffusion resistance was efficiently eliminated. Enhancing the LA concentration improved the selectivity of 2,3-pentanedione, suggesting that the reaction order of the lactic acid molecule for lactic acid conversion to 2,3-pentanedione is higher than the other side reactions. Encouragingly, in retaining 30-45% of the lactic acid conversion, the condensation reaction with a 2,3-pentanedione selectivity of around 73% proceeded efficiently for at least 116 h on stream. The long-term stability of the present catalyst was found to be related to its hierarchical pores, which ameliorated the mass transfer effect of the reactant and product, except for the appropriate acid-base properties for lactic acid condensation to 2,3-pentanedione.

Potassium-Ion-Exchanged Zeolites for Sustainable Production of Acrylic Acid by Gas-Phase Dehydration of Lactic Acid

Development of high-performance solid acid catalysts for chemicals and materials production from bioresourced feedstock has become an important research topic in heterogeneous catalysis for renewable energy and green chemistry. We provide herein a comprehensive study on the catalytic performance of various K+-exchanged zeolites (KxNa1-xZ-y, x = 0.90-0.98) with similar molar K/Al ratios for acrylic acid (AA) production by gas-phase dehydration of lactic acid (LA) and discuss the effects of zeolite type (Z = ZSM-22, ZSM-35, MCM-22, ZSM-11, ZSM-5, ZSM-5/ZSM-11, and β) and SiO2/Al2O3 ratio (y). ZSM-5 and β are found more efficient than the other zeolites for this LA-to-AA reaction. Variation of y in the zeolite (β and ZSM-5) is shown to significantly affect the catalytic performance: not only higher AA selectivity and yield but also better catalytic stability is achieved by lowering y. A K0.97Na0.03ZSM-5-27 is then identified as the best-performing catalyst, offering very high AA selectivity (80-81 mol%) and yield (74-78 mol%) at 360 °C under high LA space velocity (WHSVLA = 2.1 h-1). This catalyst also shows a remarkable long-term stability, being capable to maintain a high AA selectivity (>70 mol%) and yield (>55 mol%) for longer than 80 h. Furthermore, an in situ calcination of the used catalyst with flowing air at 450 °C is shown to be efficient for complete catalyst regeneration. Correlating the catalyst performance with its surface acid-base property measured by NH3- and CO2-TPD clearly uncovers that balance between the surface acidity and basicity would be a key, besides Z and y of the zeolite, to the catalyst performance.

Selective conversion of lactic acid into acrylic acid over hydroxyapatite catalysts

Lactic acid conversion into acrylic acid was carried out over Ca-HAP catalysts at 623 K. Stoichiometric Ca-HAP catalyst gave a high acrylic acid yield of about 60 C-%. Furthermore, non-stoichiometric calcium deficient Ca-HAP catalysts containing the specific amounts of sodium ions, which were prepared under hydrothermal conditions, exhibited remarkably high acrylic acid yields of about 80 C-%. In contrast, non-stoichiometric Ca-HAP catalysts with vacancy sites and Ca-HAP catalysts with excess amounts of sodium species showed relatively low acrylic acid yields and high selectivities into acetaldehyde and 2,3-pentanedione.

Confined alkali metal ions in two-dimensional aluminum phosphate promoted activity for the condensation of lactic acid to 2,3-pentanedione

The sustainable production of 2,3-pentanedione from bio-lactic acid was investigated over alkali metal ion-intercalated laminar aluminum phosphate. The confined alkali metal ion through the adjacent layers of aluminum phosphate offered excellent stability for the condensation of lactic acid to 2,3-pentanedione at least 80 h on stream, remaining constant at 55% conversion of lactic acid as well as around 80% of 2,3-pentanedione selectivity. The intercalated alkali metal ions can efficiently stabilize the enol intermediate, promoting the activity of lactic acid condensation. Besides, it can also prevent the occurrence of a layered stack of aluminum phosphate, providing an excellent mass transfer space for molecular diffusion, which is demonstrated by the calculation of the relation between molecular mean free paths for lactic acid and 2,3-pentanedione and the interlamellar spacing of aluminum phosphate. As a result, the alkali metal ion-intercalated laminar aluminum phosphate exhibited excellent performance for the condensation of lactic acid to 2,3-pentanedione at 270 °C, achieving 90% of lactic acid conversion and 80% of selectivity towards 2,3-pentanedione.

PREPARATION METHOD OF ACRYLIC ACID FROM LACTIDE BY USING ION EXCHANGE RESIN

The present invention relates to a method for manufacturing acrylic acid by dehydration of lactide derived from a biomass using a strongly acidic cation exchange resin. An object of the present invention is to provide the method for manufacturing acrylic acid, which is a high moisture absorbent raw material, in an environmentally friendly manner at a high yield and a high selectivity by using the strongly acidic cation exchange resin.COPYRIGHT KIPO 2019