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:

98+% ^*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:

N-acetylaziridine

1-acetyl-2-methyl-aziridine

hexahydro-2H-oxepin-2-one

cyclobutanone

Refernces

Application of ring expansions for the preparation of rac muscone and exaltone

10.1002/hlca.19750580821

The research focuses on the synthesis of complex organic compounds, specifically the preparation of rac-Muscone and Exaltone using ring expansions. Key chemicals involved include 1-morpholino-cyclododec-1-ene (7) and 1-morpholino-cyclotridec-1-en (15), which were reacted with ketene to form 4,6-Undecamethylene-2-pyron (8) and 4,6-Dodecamethylene-2-pyron (16), respectively. These compounds were then subjected to saponification and decarboxylation processes to produce mixtures of 3-methyl-cycloalkenones, which were subsequently hydrogenated to yield the desired products. The study also explores the application of the keton homologation method of Mock & Hartman, using diazoacetic ester and triethyl oxonium fluoroborate to synthesize higher homologs of cyclododecanone (1), resulting in cyclotridecanone (4) and cyclopentadecanone (5). Additionally, the research investigates the radical anion of 2,7-diazapyrene and its protonated forms, examining the changes in coupling constants and orbital sequences upon protonation.