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E.O. Lawrence Berkeley
National Laboratory
APPLICATION OF TECHNOLOGY:
- Used in conjunction with the Simons electrochemical fluorination
(ECF) method, would bring about enhanced efficiency of fluorination
of bulk chemicals
- Particularly attractive for fluorination of costly, low-volatility
and low-solubility (in aHF) organic compounds that are less amenable
to the ECF method in general use at this time
ADVANTAGES:
- Reactions take place at or below room temperature
- Most of the hydrogen atoms in organic molecules are replaced
quickly and cleanly
- Oxidant, unlike elemental fluorine, is also effective in fluorinating
cationic species
- Procedure uses only the required amount of oxidant in a one-container
procedure, generates the perfluorinated compound free of underfluorinated
products, and produces the perfluorinated product in essentially
quantitative yield
ABSTRACT:
Berkeley Lab researchers have devised a series of simple, controlled
reactions, which take place at or below room temperature, by which
hydrogen is substituted by fluorine in organic compounds. Berkeley
Labs new fluorination reactions are carried out in liquid
anhydrous hydrogen fluoride (aHF), which is easily and quantitatively
recovered. Most of the hydrogen atoms in organic molecules are replaced
quickly and cleanly by simply using a solution of a NiF62- salt for the oxidation of
H to F. Solubility of an organic compound in aHF is not necessary
for efficient fluorination, since NiF62- effectively carries the oxidizer
to insoluble compounds. This oxidant, unlike elemental fluorine,
is also effective in fluorinating cationic species. Only hydrogen
atoms at tertiary carbon sites in highly fluorinated molecules require
the more powerful oxidizers, NiF4 and NiF3, for their oxidation.
These binary fluorides are generated from the NiF62- salts using boron trifluoride,
BF3. Berkeley Labs new approach
to fluorination uses only the required amount of oxidant in a one-container
procedure, generates the perfluorinated compound free of underfluorinated
products, and produces the perfluorinated product in essentially
quantitative yield. This new process is particularly attractive
for the fluorination of costly, low-volatility and low-solubility
(in aHF) organic compounds that are less amenable to the Simons
electrochemical fluorination (ECF) method in general use at this
time. In addition, use of Berkeley Labs new process in conjunction
with the ECF method would bring about enhanced efficiency of fluorination
of bulk chemicals.
STATUS: U.S. Patent #6,160,158. Available
for licensing
REFERENCE NUMBER: IB-1216
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CONTACT:
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Technology
Transfer Department
E.O. Lawrence Berkeley National Laboratory
MS 90-1070
Berkeley, CA 94720
(510) 486-6467 FAX: (510) 486-6457
TTD@lbl.gov |
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