ketene

Base Information

• Chemical Name: ketene
• CAS No.: 463-51-4
• Deprecated CAS: 32834-27-8,32834-35-8,32834-35-8
• Molecular Formula: C2H2O
• Molecular Weight: 42.0373
• Hs Code.: 2914190090
• European Community (EC) Number: 207-336-9
• ICSC Number: 0812
• UNII: LEP3SM032A
• DSSTox Substance ID: DTXSID1052113
• Nikkaji Number: J2.590I
• Wikipedia: Ethenone,Ketene,Dicarbon_monoxide
• Wikidata: Q421032
• Metabolomics Workbench ID: 56873
• Mol file: 463-51-4.mol

Synonyms:Ketene(8CI);Carbomethene;

Chemical Property of ketene

Chemical Property:

• Appearance/Colour: COLOURLESS GAS, WITH CHARACTERISTIC ODOUR
• Vapor Pressure: 12600mmHg at 25°C
• Melting Point: -150°
• Refractive Index: 1.303
• Boiling Point: bp -56°
• PSA: 17.07000
• Density: 0.712 g/cm³
• LogP: 0.00400
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 42.010564683
• Heavy Atom Count: 3
• Complexity: 25.8
• Transport DOT Label: Poison Inhalation Hazard Flammable Liquid

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Other Toxic Gases & Vapors
• Canonical SMILES: C=C=O
• Inhalation Risk: A harmful concentration of this gas in the air will be reached very quickly on loss of containment.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. Inhalation of this gas may cause lung oedema. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged inhalation may cause effects on the lungs. This may result in emphesema and fibrosis.
• Uses: Organic chemical syntheses; conversion of higher acids into their anhydrides; for acetylation in the manufacture of cellulose acetate and aspirin For the conversion of higher acids into their anhydrides; for acetylation in the manufacture of cellulose acetate and aspirin. Ketene is used as an acetylating agent inthe production of cellulose acetate, aspirin,acetic anhydride, and in various organicsyntheses.

Technology Process of ketene

There total 263 articles about ketene 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: 70.0%

{Co2(μ-CH2)(μ-CHCH3)(CO)4(μ-dppm)} → Ketene (463-51-4) + Co2(CO)4(μ-CO)2(μ-bis(diphenylphosphino)methane) (52615-19-7) + prop-1-en-1-one (6004-44-0)

Guidance literature:

With carbon monoxide; In neat (no solvent); pyrolysis under CO atmosphere at 25°C;; not isolated; detected by NMR spectroscopy; ketenes trapped by reaction with CD3OD with formation of the corresponding esters;;

Reference yield: 25.0%

{Co2(μ-CH2)(μ-CHCH3)(CO)4(μ-dppm)} + hexafluoro-2-butyne (692-50-2) → Ketene (463-51-4) + {Co2(μ-CF3CCCF3)(CO)4(μ-dppm)} (84896-13-9,108151-17-3) + prop-1-en-1-one (6004-44-0)

Guidance literature:

In neat (no solvent); not isolated; detected by NMR spectroscopy; ketenes trapped by reaction with CD3OD with formation of the corresponding esters;;

Reference yield: 15.0%

{Co2(μ-CH2)(μ-CHCH3)(CO)4(μ-dppm)} → Ketene (463-51-4) + {Co2(μ-SO2)2(CO)4(μ-dppm)} + prop-1-en-1-one (6004-44-0)

Guidance literature:

With sulfur dioxide; In neat (no solvent); reaction for a longer period of time;; not isolated; detected by NMR spectroscopy; ketenes trapped by reaction with CD3OD with formation of the corresponding esters;;

upstream raw materials:

pyridine

triethyl phosphate

ethyl acetate

4-methyleneoxetan-2-one

Downstream raw materials:

1-acetyl-1-aza-spiro[2.5]octane

N-cyclohex-1-enylmethyl-acetamide

(1-acetoxy-vinyl)-phosphonic acid dimethyl ester

dimethyl acetylphosphonate

Refernces

• 1、 Beach,Eyermann,Smit,Xiang,Xiang. "APPLICATIONS OF THE EQUIVALENT CORES APPROXIMATION. THE DETERMINATION OF PROTON AFFINITIES AND ISOCYANIDE-TO-NITRILE ISOMERIZATION ENERGIES FROM CORE BINDING ENERGIES.". . p. 536 - 539. Retrieved 1984.
• 2、 Akita, Munetaka,Andoh, Hitoshi,Mitani, Osamu,Oku, Tomoharu,Moro-Oka, Yoshihiko. "Reactivities of ketene ligands on polymetallic systems". . p. 107 - 116. Retrieved 1989.
• 3、 Devriendt, K.,Van Poppel, M.,Boullart, W.,Peeters, J.. "Kinetic Investigation of the + H -> CH(X2II) + H2 Reaction in the Temperature Range 400 K < T < 1000 K". . p. 16953 - 16959. Retrieved 1995.
• 4、 Rice,Vollrath. "-". . . Retrieved 1930.
• 5、 Zaleski, Daniel P.,Sivaramakrishnan, Raghu,Weller, Hailey R.,Seifert, Nathan A.,Bross, David H.,Ruscic, Branko,Moore, Kevin B.,Elliott, Sarah N.,Copan, Andreas V.,Harding, Lawrence B.,Klippenstein, Stephen J.,Field, Robert W.,Prozument, Kirill. "Substitution Reactions in the Pyrolysis of Acetone Revealed through a Modeling, Experiment, Theory Paradigm". . p. 3124 - 3142. Retrieved 2021.
• 6、 Sheridan, Robert S.,Kasselmayer, Mark A.. "Infrared Spectrum and Photochemistry of Methoxychlorocarbene". . p. 436 - 437. Retrieved 1984.
• 7、 Bouchoux, Guy,Salpin, Jean-Yves. "Thermokinetic Determination of Gas-Phase Basicities. Application to Ketene, Methylketene, and Formaldimine". . p. 16555 - 16560. Retrieved 1996.
• 8、 Keul, Felix,Mardyukov, Artur,Schreiner, Peter R.. "Preparation and characterization of the enol of acetamide: 1-aminoethenol, a high-energy prebiotic molecule". . p. 12358 - 12363. Retrieved 2020.
• 9、 Braun, Walter,McNesby, J. R.,Scheer, Milton D.. "A Comparative Rate Method for the Study of Unimolecular Falloff Behavior". . p. 1846 - 1850. Retrieved 1984.
• 10、 Bibas, Herve,Wong, Ming Wah,Wentrup, Curt. "The vinylketene-acylallene rearrangement: Theory and experiment". . p. 237 - 248. Retrieved 1997.