Hydroxyacetone

Base Information

• Chemical Name: Hydroxyacetone
• CAS No.: 116-09-6
• Molecular Formula: C3H6O2
• Molecular Weight: 74.0794
• Hs Code.: 29144090
• European Community (EC) Number: 204-124-8
• NSC Number: 102497
• UNII: 7I7YM0835W
• DSSTox Substance ID: DTXSID8051590
• Nikkaji Number: J2.470H
• Wikipedia: Hydroxyacetone
• Wikidata: Q20236702
• Metabolomics Workbench ID: 39108
• Mol file: 116-09-6.mol

Synonyms:acetol;hydroxyacetone

Chemical Property of Hydroxyacetone

Chemical Property:

• Appearance/Colour: colorless to yellow liquid
• Vapor Pressure: 1.91mmHg at 25°C
• Melting Point: -17 °C(lit.)
• Refractive Index: n20/D 1.425(lit.)
• Boiling Point: 145.5 °C at 760 mmHg
• PKA: 13.14±0.10(Predicted)
• Flash Point: 52.2 °C
• PSA: 37.30000
• Density: 1.019 g/cm³
• LogP: -0.43230
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: water: miscible
• Water Solubility.: Miscible with water, alcohol and ether.
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 74.036779430
• Heavy Atom Count: 5
• Complexity: 40.2

Purity/Quality:

99% ^*data from raw suppliers

Hydroxyacetone ^*data from reagent suppliers

Safty Information:

• Statements: 2017/10/16
• Safety Statements: 23-24/25-5

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: CC(=O)CO
• Uses: Hydroxyacetone is a chemical reagent used in various organic chemical reactions. It is a component of the Mannich reaction, amino acid caalyzes direct asymmetric aldol reactions. In the pharmaceutical setting, this compound is used in the synthesis of imidazoles acting as potent and orally active antihypertensive agents. Reagent in organic synthesis; protecting group for the synthesis of peptides. Hydroxyacetone is used as a reagent in organic chemical reactions. It also serves as a component for Mannich reaction and aldol reactions. It is also used in the syntheses of 2-oxo-propionaldehyde, imidazoles, polyols, acrolein, dyes and skin tanning agents. It yields (R)-1,2-propanediol upon reduction of hydroxyacetone in the presence of a microbial cell catalyst.

Technology Process of Hydroxyacetone

There total 462 articles about Hydroxyacetone 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: 24.6%

propylene glycol (57-55-6,63625-56-9) → 2-hydroxypropanal (3913-65-3) + hydroxy-2-propanone (116-09-6)

Guidance literature:

With 5% CuO-5% PdO-0.5% Bi2O3-0.5% In2O3/modified γ-Al2O3 catalyst; at 180 ℃;

Reference yield:

1,3-Dichloropropane (142-28-9) + 1-chloro-3-hydroxypropane (627-30-5) → glycidyl methyl ether (930-37-0) + 1,2-Epoxyhexane (1436-34-6) + 2,3-Dichloroprop-1-ene (78-88-6) + 2-chloroallyl alcohol (5976-47-6) + 1,2,2-trichloropropane (3175-23-3) + 1,2-Dichloropropane (26198-63-0,78-87-5) + cis-1,3-Dichloropropene (10061-01-5) + 1,2,3-trichloro-1-propene (13116-58-0) + (1Z)-1,2,3-trichloroprop-1-ene (96-19-5,13116-58-0,13116-57-9) + 1,3,3-trichloro-propene (2953-50-6) + 1t,3,3-trichloro-propene (2598-01-8) + chlorodibromomethane (124-48-1) + 1,1,2-trichloropropane (598-77-6) + 2,3-Dichloro-1-propanol (616-23-9) + 1,3-Dichloro-2-propanol (96-23-1) + 1,2,3-trichloropropane (96-18-4) + 3,3-dichloropropene (563-57-5) + 3,3-dichloroallyl chloride (2567-14-8) + acetaldehyde (75-07-0,9002-91-9) + allyl alcohol (107-18-6) + hydroxy-2-propanone (116-09-6) + chloroacetone (78-95-5) + cyclopentanone (120-92-3) + chlorobenzene (108-90-7) + isopropyl alcohol (67-63-0,8013-70-5) + 3-monochloro-1,2-propanediol (96-24-2) + acrolein (107-02-8,25068-14-8) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) + (E)-1,3-dichloro-prop-1-ene (10061-02-6)

Guidance literature:

With sodium hydroxide; water; at 45 - 62.4 ℃; under 112.511 - 750.075 Torr; Product distribution / selectivity;

Reference yield:

glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → propylene glycol (57-55-6,63625-56-9) + ethanol (64-17-5) + carbon dioxide (124-38-9,18923-20-1) + hydrogen (1333-74-0) + ethylene glycol (107-21-1) + hydroxy-2-propanone (116-09-6)

Guidance literature:

With prereduced 3 wtpercent Pt modified Ir supported on silica; In water; at 189.84 ℃; for 4h; under 15001.5 Torr; Inert atmosphere;

DOI:10.1016/j.cattod.2015.10.023

upstream raw materials:

1,4-dihydroxybut-2-yne

methanol

bromo-2 propanal

potassium formate

Downstream raw materials:

Acetol acetate

ethyl 2,4-dimethylfuran-3-carboxylate

2-(cyclohexylamino)propan-1-ol

2,3-hexanedione

Refernces

• 1、 Bridier, Isabelle,Veyret, Bernard,Lesclaux, Robert,Jenkin, Michael E.. "Flash Photolysis Study of the UV Spectrum and Kinetics of Reactions of the Acetonylperoxy Radical". . p. 2993 - 2997. Retrieved 1993.
• 2、 Venkatakrishnan, Vinod Kumar,Degenstein, John C.,Smeltz, Andrew D.,Delgass, W. Nicholas,Agrawal, Rakesh,Ribeiro, Fabio H.. "High-pressure fast-pyrolysis, fast-hydropyrolysis and catalytic hydrodeoxygenation of cellulose: Production of liquid fuel from biomass". . p. 792 - 802. Retrieved 2014.
• 3、 Montes,Boutonnet,J?r?s,Marinas,Marinas,Urbano. "Selective transformation of glycerol into 1,2-propanediol on several Pt/ZnO solids: Further insight into the role and origin of catalyst acidity". . p. 246 - 258. Retrieved 2015.
• 4、 Dey, Sangeeta,Karukurichi, Kannan R.,Shen, Weijun,Berkowitz, David B.. "Double-cuvette ISES: In situ estimation of enantioselectivity and relative rate for catalyst screening". . p. 8610 - 8611. Retrieved 2005.
• 5、 Ang, Ee Lui,Cao, Peng,Chen, Jiawei,Li, Yaxin,Lin, Lianyun,Liu, Jiayi,Liu, Yangping,Liu, Yanhong,Lu, Qiang,Teng, Lin,Wei, Yifeng,Xu, Runyao,Yin, Jinyu,Yuchi, Zhiguang,Zhai, Weixiang,Zhang, Yan,Zhao, Huimin,Zheng, Yuchun. "Two radical-dependent mechanisms for anaerobic degradation of the globally abundant organosulfur compound dihydroxypropanesulfonate". . p. 15599 - 155608. Retrieved 2020.
• 6、 Prey,Waldmann. "". . p. 65. Retrieved 1952.
• 7、 Paizs, Csaba,Tosa, Monica,Majdik, Cornelia,Bodai, Viktoria,Novak, Lajos,Irimie, Florin-Dan,Poppe, Laszlo. "Chemo-enzymatic preparation of hydroxymethyl ketones". . p. 2400 - 2402. Retrieved 2002.
• 8、 Gandarias, Inaki,Arias, Pedro Luis,Fernández, Sara G.,Requies, Jesús,El Doukkali, Mohammed,Güemez, María Belén. "Hydrogenolysis through catalytic transfer hydrogenation: Glycerol conversion to 1,2-propanediol". . p. 22 - 31. Retrieved 2012.
• 9、 Slates et al.. "-". . p. 457. Retrieved 1969.
• 10、 Dieuzeide,de Urtiaga,Jobbagy,Amadeo. "Vapor phase hydrogenolysis of glycerol to 1,2-propanediol at atmospheric pressure over copper catalysts supported on mesoporous alumina". . p. 19 - 25. Retrieved 2017.