Tetrafluoroethylene

Base Information

• Chemical Name: Tetrafluoroethylene
• CAS No.: 116-14-3
• Deprecated CAS: 9014-83-9,1449755-53-6
• Molecular Formula: C2F4
• Molecular Weight: 100.016
• Hs Code.: 3904610000
• European Community (EC) Number: 204-126-9
• ICSC Number: 1779
• UN Number: 1081
• UNII: OMW63Z518S
• DSSTox Substance ID: DTXSID6021325
• Nikkaji Number: J1.147.712G,J2.471F
• Wikipedia: Tetrafluoroethylene
• Wikidata: Q412460
• NCI Thesaurus Code: C44452
• Metabolomics Workbench ID: 56044
• ChEMBL ID: CHEMBL541730
• Mol file: 116-14-3.mol

Synonyms:tetrafluoroethene;tetrafluoroethylene;tetrafluoroethylene, ion(1+);tetrafluoroethylene, ion(1-)

Chemical Property of Tetrafluoroethylene

Chemical Property:

• Appearance/Colour: colourless gas
• Vapor Pressure: 20000mmHg at 25°C
• Melting Point: -142 °C
• Refractive Index: 1.241
• Boiling Point: -76.301 °C at 760 mmHg
• Flash Point: -119.677 °C
• PSA: 0.00000
• Density: 1.306 g/cm³
• LogP: 1.99100
• Water Solubility.: 110mg/L at 28℃
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 99.99361265
• Heavy Atom Count: 6
• Complexity: 55.6
• Transport DOT Label: Flammable Gas

Purity/Quality:

98% ^*data from raw suppliers

TETRAFLUOROETHYLENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,F
• Hazard Codes: C,F
• Statements: 11
• Safety Statements: 16-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Aliphatics, Unsaturated
• Canonical SMILES: C(=C(F)F)(F)F
• Inhalation Risk: On loss of containment this substance can cause serious risk of suffocation when in confined areas.
• Effects of Short Term Exposure: Asphyxiation. The liquid may cause frostbite.
• Effects of Long Term Exposure: The substance may have effects on the kidneys, liver and blood. This may result in impaired functions of organs. This substance is probably carcinogenic to humans.
• General Description: Tetrafluoroethylene (TFE) serves as a critical reactant in nickel-catalyzed carbon-carbon bond-forming reactions, particularly in oxidative cyclization with ethylene to generate 2,2,3,3-tetrafluoronickelacyclopentanes. These nickelacycles act as key intermediates, enabling further transformations such as cotrimerization to produce fluorinated alkenes like 5,5,6,6-tetrafluoro-1-hexene, as well as cross-trimerization with enones. The reactivity and structural confirmation of these intermediates highlight TFE's utility in synthesizing fluorinated organic compounds through transition-metal catalysis.

Technology Process of Tetrafluoroethylene

There total 295 articles about Tetrafluoroethylene 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: 99.0%

1,2,2,3,3-pentafluoro-1-difluoromethylcyclopropane (379-14-6) + cyclohexene (110-83-8) → polytetrafluoroethylene (116-14-3,82785-14-6) + pentafloropropylene (433-66-9) + carbon monoxide (201230-82-2) + Octafluorocyclobutane (115-25-3) + 7,7-difluoronorcarane (823-70-1) + silicon tetrafluoride (7783-61-1)

Guidance literature:

With Pyrex tube; at 200 ℃; for 320h; Product distribution; Mechanism; further periods of contact time, other temperatures;

Reference yield:

halon-1211 (353-59-3) → hydrogenchloride (7647-01-0,15364-23-5) + polytetrafluoroethylene (116-14-3,82785-14-6) + hydrogen fluoride (7664-39-3,12381-92-9,32057-09-3,74835-82-8) + hydrogen bromide (10035-10-6,12258-64-9) + pyrographite (7440-44-0)

Guidance literature:

With hydrogen; In neat (no solvent); reaction with H2 at 400-600°C; mechanism discussed; further product;;

Reference yield:

dibromodifluoromethane (75-61-6) → polytetrafluoroethylene (116-14-3,82785-14-6) + hydrogen fluoride (7664-39-3,12381-92-9,32057-09-3,74835-82-8) + hydrogen bromide (10035-10-6,12258-64-9) + bromine (7726-95-6)

Guidance literature:

In neat (no solvent); thermal decomposition on passing through a tube at 900°C;;

upstream raw materials:

carbon tetrafluoride

1,1,2,2-tetrafluoro-1-bromo-2-chloroethane

Chlorodifluoromethane

2-chloro-1,1,2,2-tetrafluoroethane

Downstream raw materials:

1,1,2,2-tetrafluoro-3-phenylcyclobutane

dichloro-methyl-(1,1,2,2-tetrafluoro-ethyl)-silane

dichloro-methyl-(4H-octafluoro-butyl)-silane

2,2,3,3-tetrafluoropropanol

Refernces

2,2,3,3-tetrafluoronickelacyclopentanes generated via the oxidative cyclization of tetrafluoroethylene and simple alkenes: A key intermediate in nickel-catalyzed C-C bond-forming reactions

10.1021/acs.organomet.5b00218

The research primarily investigates the oxidative cyclization of tetrafluoroethylene (TFE) with ethylene using Ni(0) to form a five-membered nickelacycle, which is a key intermediate in nickel-catalyzed carbon-carbon (C?C) bond-forming reactions. The study focuses on the synthesis and characterization of 2,2,3,3-tetrafluoronickelocyclopentanes, which are generated through this cyclization process. The nickelacycle was isolated using PPh3 as an auxiliary ligand, and its structure was confirmed through X-ray analysis. Experiments involved reacting TFE and ethylene with Ni(0) in the presence of PPh3, leading to the formation of the nickelacycle, which was then further reacted with ethylene to produce a cotrimerization product, 5,5,6,6-tetrafluoro-1-hexene. The reactivity of the nickelacycle with various enones was also explored, resulting in cross-trimerization products. The research utilized various analytical techniques, including NMR and X-ray diffraction, to characterize the intermediates and products. The study also attempted to apply these reactions catalytically, achieving selective cotrimerization of TFE with ethylene to form the desired product with a low turnover number.