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Patented Nov. 19, 1946
,
2,411,158
UNITED STATES PATENT orncs
2,411,158
SATURATED POLYFLUORO CARBONYL COM
POUNDS AND THEIR PREPARATION
William Edward Hanford, Easton, Pa., assignor to
E. I. du Pont de Nemours 8: Company, Wilming
ton‘, DeL, a corporation oi Delaware
No Drawing. Application April 23, 1943,
1
Serial No. 484,298
8 Claims. (Cl. 260—-‘586)
2
This invention relates to the preparation of
.
A preferred form of the invention may be car
?uorinated organic compounds and to new or
‘ ganic ?uorine compounds. More particularly, the
invention comprises a new process for the prep
ried out by reacting tetra?uoroethylene with a
saturated organic carbonyl compound containing
at least two carbon atoms and containing only
aration of poly?uoro carbonyl compounds and in
cludes new chemical products consisting of sat~
carbon, hydrogen and oxygen atoms, preferably
urated organic carbonyl compounds containing .
one or more polyfluoroethylene groups per mole- -
in a closed system and in the presence of a cata
lyst. Saturated organic poly?uoro carbonyl com
pounds are obtained containing one or more
. tetra?uoroethylene units per molecule of car
Heretofore the only practical method for pre 10 bonyl compound. These resulting products may
, paring ?uorine-containing organic compounds
be represented by the general formula
cule.
has been to replace chlorine with ?uorine by
means of various inorganic reagents, such as
hydrogen ?uoride, silver ?uoride, antimony ?uo-‘
where n is a positive integer in'the range 1 to
rides, mercuric fluoride-and other metallic ?uo 15 about 25, and Z is the complementary portion of
rides. Such processes yield mixtures of inert prod
- the carbonyl reactant, being a monovalent sat
ucts, are very restricted in application and in
volve considerable expense.
It‘ has also previously been proposed to pro
urated organic radical consisting solely of car
bon, hydrogen and oxygen atoms and containing
duce organic ?uorine compounds by the reaction 20
of ?uorine with various organic materials. Prior
investigations have shown that this reaction of
at least two carbon atoms and at least one car
bonyl group.
I
The polyfluoroethylenes suitable for use in this
invention may be represented by the general for
mula CX2=CX2 where one X is selected from
?uorine is extremely energetic and generally
causes pyrolysis of the organic material, result
the group consisting of hydrogen and halogen
ing in the formation of carbon, tar or other un 25 and the other three X’s are halogen of which at
desirable carbonaceous decomposition products.
least two are ?uorine.
It is an object of this invention to provide a
new process for the preparation of saturated or
ganic polyfluoro carbonyl compounds. Another
object of this invention is to obtain new compo
sitions of matter consisting of ?uorinated or
Saturated organic carbonyl compounds suit
able for use in this invention are free of ethylenic
and acetylenic linkages, contain at least two car
30 bon atoms and at least one
0
ganic compounds containing the carbonyl func
tional group.
Still another object is to prepare
?uoro carbonyl compounds which have outstand
group and consist of only carbon, hydrogen and
ing thermal and chemical stability. A further ob ' oxygen atoms. These saturated organic carbonyl
ject is to provide a relatively simple and inex
compounds may be acyclic or cyclic, including
pensive process for readily preparing saturated
aliphatic, alicyclic,‘ aromatic and heterocyclic sat
organic carbonyl compounds containing one or
urated organic carbonyl compounds consisting
more poly?uoroethylene groups per molecule. _ A '
solely of carbon, hydrogen and oxygen atoms‘.
still further object is to obtain saturated organic 40 The general formula ZH may be used-to repre
?uorinated carbonyl compounds possessing many
sent these organic carbonyl compounds where Z
novel and useful properties. Other objects will
is the complementary portion of the carbonyl re
appear hereinafter.
actant, being a monovalent saturated organic
These objects are accomplished by reacting a
radical consisting solely of carbon, hydrogen and
poly?uoroethylene containing at least three halo 45 oxygen atoms and containing at least one
gen atoms of which at least two are ?uorine with
a saturated organic carbonyl compound contain- T
0
%
.__c_
ing at least two carbon atoms and containing only
carbon, hydrogen and oXygen atoms.’ This re
group and at least two carbon atoms.
action produces saturated organic polyfluoro car 50
The saturated organic ?uorinated carbonyl
bonyl products containing at least one poly?uoro
compounds prepared in accordance with this in
ethylene unit per molecule of carbonyl reactant.
vention may be represented by the general for
The pre?x “poly” as used herein refers to the
mula H(CX2CX2)nZ where n is a positive integer
number of ‘?uorine atoms in the fluoroethylene
in the range 1 to about 25, one X is selected from
molecule and not to polymeric materials.
the group qqnsisting of hydrogen and halogen, the
I
2,411,158
4
number of (C&CX2) groups in the compound
and is a positive integer in the range 1 to about
other three X's are halogen of which at least two
are ?uorine, and Z is the complementary por
tion of the carbonyl reactant being a monovalent
saturated organic radical consisting solely of car
bon. hydrogen and oxygen atoms and containing
25, m is the number of (CXzCXr) groups con
tained in V and is an integral number in the
range 0 to about 25 but is not greater than n,
and V is a monovalent saturated organic radical
at least one
containing m(CXzCX2) groups and at least 1' ~ 10
0
carbon atoms exclusive. of those present in the
(0&CX2) portion of the radical and at least one
%
group and at least two carbon atoms. In the
preferred products n is a positive integer in the
10
0
%
__C....
range 1 to 15.
group but otherwise consisting solely of carbon,
It is also possible to obtain products in which
all of the ?uoroethylene units are not necessarily 15 hydrogen and oxygen atoms.
The method for carrying out the reactions var
connected together and which may be represent
ies to some extent with different types of car
ed by the general formula
bonyl compounds, but the usual procedure com
prises placing a given amount of a saturated or
where n'is a positive integer in the range 1 to
about 25, m is not greater than n and is an in
tegral number in the range from 0 to about 25,
one X in each parenthesis is selected from the
group consisting of hydrogen and halogen, the
other three X’s in each parenthesis are halogen
of which at least two are ?uorine and Y is the 25
ganic carbonyl compound and of a poly?uoro
ethylene, such as tetra?uoroethylene, with or
without a catalyst in a high-pressure reaction
vessel and then closing and heating to the de
sired reaction temperature while mechanically
agitating the reaction vesse1 for several hours.
In order to prepare the low molecular weight
complementary portion of the carbonyl reactant,
products which are characteristic of this inven
tion, it is usually desirable to carry out the reac
tions under pressure at elevated temperatures.
sisting solely of carbon, hydrogen and oxygen
The temperature at which thereaction is ef
atoms and containing at least one
30 fected may be varied over a wide range, depend
0
ing largely upon the nature of the reactants’, the
%
being a divalent saturated organic radical con
_.C_..
group and at least two carbon atoms. It is to
be understood that the units in parentheses cor
respond to the particular ?uoroethylene which is
employed in the reaction, although tetra?uoro
ethylene is the preferred reactant. The sum to
catalyst, the resultsdesired, and other conditions
of the reaction. However, the temperature should
be below that at which decomposition or pyrolysis
35
of either the reactants or products occurs. No
appreciable reaction is obtained below 50° C. and
it is usually necessary to heat the reaction mix
ture to 75° C. or higher in order to obtain a
tal of the atoms other than the ?uoroethylene
substantial
reaction in a reasonable time. The
units is equivalent to only one molecule of the 40 preferred temperature range is ‘IS-250° C., but
original organic carbonyl compound. Thus the
higher temperatures up to approximately 350° C.
saturated organic carbonyl compounds in this in
are sometimes desirable.
'
vention react with a ?uorocarbon, such as tetra
A series of products are usually obtained which
?uoroethylene, to yield a series of monomeric sat
vary from liquids to solids depending upon the.
urated organic poly?uoro carbonyl compounds.
carbonyl compound and the number of poly?uoro
The following speci?c example is given to fur
ethylene units per molecule of product. In gen
ther illustrate the invention:
eral, the liquid products are compatible with the
common organic solvents, whereas the low mo
0
50
lecular weight solid products have limited solu
bility or are insoluble in most solvents.
The invention is further illustrated by the fol
lowing examples in which the parts are by weight '
55 unless otherwise speci?ed.
This product may react with additional tetra
?oroethylene as illustrated below:
Further reaction with tetra?uoroethylene may
also occur. Thus the most general formula rep
resenting the new saturated poly?uoro carbonyl
products is H(CX2CX2)n—1n—V where one X is
selected from the group consisting of hydrogen
and halogen and the other three X’s are halogen
of which at least two are ?uorine, n is the total
Edcample' I
A silver-lined autoclave was flushed with nitro-v
gen and charged with 146 parts of freshly dis
tilled methyl formate and 1.5 parts of benzoyl per
oxide. ‘Aftér pressuring with tetra?uoroethylene
to_350 lbs/in.2 at 110° 0., the autoclave was closed
and heated with agitation for 8.5 hours at 110° C.
The reaction mixture was steam distilled to yield
(35 .4 part of steam-volatile solid melting at about
100° C. and 7.2 partsvof non-steam-volatlle solid
melting at about 250°-260° C.
.
F
. v
.
.
Analysis of nonsteam-volatile solid melting at about 250°-260° 0..
Calculated for CILHIFMOI ..................... __'_' ..... -. ...... _.
Per cent
69. 38
_ 69. 1
\
Average ratio
O
H
(mm/Hoooom
Per cent
Per cent
25. 81
0. 86
____________________ __
25. 45
0.61
6/1
2,411,158
5
.
Example II
volatile products and 6 parts of waxy nonsteam
A mixture of 150 parts of ethyl propionate and
1.5 parts of benzoyl peroxide was‘ reacted with
volatile solid melting at about 210° C. were ob
tamed
tetra?uoroethylene under 350 lbs./in.=.I pressure at
Emmgle VII
110° C. for 9 hours as described in Example I. b
A mixture of 150 parts of ethylene glycol di
Steam distillation and removal of the unreacted
ethyl propionate gave about 6 parts of steam-vol-
acetate, 1.5 parts of benzoyl peroxide and 50 parts
of tetra?uoroethylene was reacted in an auto
atile liquid products and '7 parts of greasy non-
.
clave at 110° C‘. for 8 hours.
steam-volatile solid products.
There was obtained
1.3 parts of steam-volatile solid melting at about
Analysis 01' greasy nonsteam-volatile solid products ...... ._
Calculated I01‘ CoHmFsO: ------------------------------- -_
F
C
Per cent
45. 58
50._3
Per cent
40. 08 '
35. 6
' The Solid Products exhibited good lubricating
A
E
i
(omoygfli-igforstooolm
Per cent
3. 72
__________________________ __
3. 29
2/1
99° C. and 5 parts of nonsteam-volatile solid melt
properties.
20 ing at about 250°-255° C.
Example III
E
m 1 VI"
A mixture of 150 parts of glacial acetic acid and
x?‘ p e
1.5 parts of benzoyl peroxide was reacted with
A mixture of 150 parts of cyclohexanone and
tetra?uoroethylene under 350 lbs./in.2 pressure at
1.5 parts of lauroyl peroxide was reacted with tet
110“ C. for 9 hours. Steam distillation of the 25 ra?uoroethylene under 350 lbs/in.2 pressure at
reaction mixture yielded?parts of nonsteam-vol110° C. for 8.5 hours. There was obtained 10
atile solid melting at about 260°-285° 0.
parts of steam-volatile liquid products which were
A
ti
F l 0 I H . was
tea].
Per cent
65.03
Analysis of nonsteam-volatile solid melting at about 260°—285° C.
Calculated for CwHrFmoz ..................................... ._
Per cent
27. 32
66. 1
Example IV
.
26.1
Per cent
0. 61
____________________ __
0. 87
4/1
‘heavier than water and could be separated by
on repeatingExamme In using 150 parts of
fractional distillation into various fractions cor
propionic acid instead of glacial acetic acid, 2.4 40 respondmg to the 1/1 and hlghel‘ tetra?uoroeth
parts of steam-volatile water-insoluble solid .
melting at about 45°-50° C. and 8 parts of non
steam-volatile solid melting at about 225° C. were
obtained.
ylene/cyclohexanone reactlon Products
Emmple IX
The products were readily soluble in
dilute sodium hydroxide and alcohol.
’
45
A mixture of 140 parts of methyl ethyl ketone.
.
F
‘ '
Analysis oisteam-volatile solid_.___' ___________________________ __
H
Per cent
56.22
Per cent
27. 74
55.4
30. 65
2.19
66.13
26. 83
1.56
66. 2
27- 2
1. 05
Calculated for C7H5F5oz ________________________ ___-Analysis of nonsteam-volatile solid. _______________ __
0
_-_
0810111812611 for 01311915300: _____________________________________ __
Example V
A
t.’
m?‘it‘f?iéé‘tn
Per cent
1.78 ~ ____________________ __
2/1
____________________ _
5/1
1.5 parts of benzoyl peroxide and 50 parts of
.
On repeating Example II usmg
1000 lbs./in.2
tetra?uoroethylene
was ‘ reacted 8.5 hours at
o
tetra?uoroethylene pressure instead of 350
no
_Th_ere was obtamed 4 parts of Steam‘
1bs_/in.2, parts of Steam_volatile
products
Volatile
products heavier than Water and
and 35 parts of nonsteam-volatile granular 501141 60 7.1 parts of non-volatile solid products melting at
'were obtained.
about 230° C. .
F
Average ratio
(C1FOIG2H5COOC2H5
Per cent
Analysis of nonsteam-volatile granular solid.
Calculated f0!‘ C?HmF?Qz ................ __
65. 03
64- 9
__________________________ __
(ill
Example VI
'
Example X
A mixture of 150 parts'of diethyl malonate and
1.5 parts of benzoyl peroxide was reacted with
A mixture of ‘155 parts of acetic anhydride, 1.5
parts of benzoyl peroxide and 50 parts of tetra
tetra?uoroethylene under 350 lbs/in.2 pressure
- ?uoroethylene was reacted 9.5 hours at 110° C.
at 110° C. for 9hours. About 1.5 parts of steam- 75 There was obtained .5 part of steam-volatile
2,411,158
7
8
liquid product and 15.4 parts of nonsteam
volatile solid products.
pentaacetate, sucrose octaacetate and cellulose
acetate; and polyvinyl acetate.
F
-
Analysis of steam-volatile liquid products..Calculated for C'HQFIO‘ .................. -_
Ratio (O,F4)/(OH;CO),0
Per cent
45-02
50- 3
.......................... __
2/1
Example XI
10
It is often desirable to use a catalyst, although a
catalyst is not always necessary. A wide variety
A mixture of 150 parts of methoxyethyl
of catalysts are operable including organic and
methoxyethoxy-acetate, 50 parts of tetra;
inorganic peroxygen compounds, alkaline cata
?uoroethylene and 1.5 parts of benzoyl peroxide
lysts, and various acid type catalysts. The per
was reacted 10 hours at 110° C. There was ob
tained 1.5 parts of steam-volatile liquid products 15 oxygen type catalysts are preferred for use in
this invention and examples of them are diacyl
heavier than water and 15.2 parts of steam
volatlle oil heavier than water which on frac
peroxide, benzoyl peroxide, lauroyl peroxide,
111325‘ °-=1.3741, had the following composition:
catalysts for use in this invention are borax,
ethyl peroxide, sodium peroxide, hydrogen
tional distillation yielded products with increas
peroxide, barium peroxide, oxygen, ozone, air
ing percentage of ?uorine with increase in boiling
point. Fraction distilling at 125°-139° C./1 mm., 20 and ammonium persulfate. Examples of alkaline
Ratio
F
O
H
'
(cam/08111.05.
Analysis of fraction distilling Per cent Per cent Per cent
at USP-139° C./l mm ______ __
Calculated for CHHNFHQL--.
44. 66
33. 14
3. 85
__________________ __
46.3
34.15
3.25
3/1
Among the poly?uoroethylenes which are ap
plicable in this invention are tri?uorochloro
ethylene,
di?uorodichloroethylene,
bromoethylene and tri?uoroethylene.
'
30 disodium phosphate, sodium alcoholate, hy
tri?uoro
drazine, hydrazine salts, trimethylamine oxide,
hexachloroethane-trimethylamine oxide, hexa
However,
chloroethane,
hexachloroethane - borax
and
peroxide-,borax. Among the acid type catalysts
poly?uoroethylenes containing three ?uorine
atoms react more readily than the di?uoroethy 35 which may be used in this invention are Friedel
Crafts type catalysts, zinc chloride and phos
‘
Tetra?uoroethylene is particularly pre
lenes.
ferred as it reacts the most readily.
The preferred saturated organic carbonyl
compounds are those containing a single
' phoric acid.
The proportion of catalyst may vary within‘
relatively wide limits depending largely upon the '
40 nature of the reactants and the products desired.
Although ef?cient reaction may be effected with
_._C_..
out the use of catalysts, it is generally preferred
group per molecule. Ketones are a particular
to employ a catalyst in this invention. Further
preferred class of compounds foruse in this in
more, the use of small amounts of catalyst're
vention. However, the invention is applicable to 45 duces the temperature, time and cost'of opera- '
other saturated organic carbonyl compounds
tion. Highly desirable results may be obtained
0
H
‘ containing at least two carbon atoms and con
with the use of an amount of catalyst corre
taining only carbon, hydrogen and oxygen atoms,
such as aldehydes, including for example,
sponding to about .001 to 10.0% by weight of the
reactants employed. Advantageous results are
acetaldehyde, propionaldehyde, n-butyraldehyde, 50 also sometimes obtained by using a combination
isobutyraldehyde, heptaldehyde and lauralde
of catalysts.
hyde; ketones, including for example, acetone,
Although a mixture of saturated organic car
methyl ethyl ketone, methyl propyl ketone,
bonyl compounds may be employed in this inven
diethyl ketone, methyl isobutyl ketone, methyl
tion, it is preferable to use a single saturated or
tert.-butyl ketone, diisopropyl ketone, methyl 55 ganic carbonyl compound.‘ It is also preferable
that the carbonyl compounds not be contami
nonyl ketone, laurone, stearone, cyclohexanone
and acetophenone; carboxylic acids, including for
nated with other type organic compounds. Gen
example, acetic, propionic, isobutyric, pivalic,
erally a relatively large molar excess of the car
bonyl reactant is used as compared to the more
caprylic, lauric, stearic, adipic and sebacic acids;
carboxylic acid anhydrides, such as acetic, 60 expensive poly?uoroethylene in order to prepare
propionic, succinic and glutaric anhydrides; and
esters of carboxylic acids, including for example,
methyl formate, ethyl acetate, methyl propionate,
methyl isobutyrate, ethyl butyrate, lauryl acetate,
phenyl acetate,‘ diethyl oxalate, diethyl malonate;
diethyl .succinate, diethyl adipate, dimethyl
sebacate, methylene diacetate,. ethylene glycol
low molecular weight products. However,_the de
sired products may often be obtained by using a
relatively small amount of the organic carbonyl
compounds since the ratio of- poly?uoroethylene
65 units per unit of ‘carbonyl compound in the prod
ucts varies' from 1 to about 25 depending upon the
conditions. Usually the molar ratio of carbonyl
compound to poly?uoroethylene in the reaction
diacetate, ethyl benzoate and ethyl furoate. Of
the aromatic compounds, those containing an
mixture may vary from .04 to 20 but it is prefer
aliphatic radical such as acetophenone, phenyl 70 able to work in the range .1 to 10 in order to ob
acetate and ethyl benzoate are preferred as they
tain the low molecular weight products which
react more readily. Carbonyl compounds of
are characteristic of this invention.
higher molecular weight which are operable in
It will be understood that the operating condi
tions may vary widely depending upon the na
the process of this invention include the esters
of mono-, di- and polysaccharides such as glucose 76 ture of the compounds being reacted and also.
9,411,158.
upon the results desired. The time required for
carrying out the reactions may vary from a few
minutes to several days depending upon the na
ture of the reactants and the other operating con
ditions such as temperature, pressure and cata
lyst.
'
The process may be operated continuously or
intermittently. The reaction may be carried out
in a closed system or the reaction may be car
10
bonyl products of this invention are useful as
. lubricants since they have outstanding thermal
and chemical stability.
This invention is particularly advantageous in '
that it affords a safe, ?exible, practical and eco
nomical process for producing highly ?uorinated
saturated organic carbonylcompounds. One of
the advantages of this invention is that the proc
ess may be operated with none or a relatively
ried out in the vapor phase by mixing the vapors 10
small amount of catalyst and the reaction pro
of the organic carbonyl compound and poly
ceeds smoothly and easily without undesirable
?uoroethylene and passing the mixture of vapors
side reactions.
‘ through a hot reaction tube which if desired may
As many apparently widely different embodi
contain a catalyst. The reaction may be carried
out under subatmospheric, atmospheric, or su 15 ments of this invention may be made without
departing from the spirit and scope thereof, it is
peratmospheric pressure in the range of .1 to
to be understood that I do not limit myself to the
1000 atmospheres. The preferred pressure range
specific embodiments thereof except as de?ned
is 1 to 200 atmospheres.
in the appended claims.
Although there is no objection to the presence
I claim:
,
of small amounts of water in carrying out the 20
1.
The
process
for
obtaining
a
mixture
of tet
process of this invention, it is preferable that the
ra?uoroethyl carbonylic compounds which com
reaction be conducted under substantially anhy
prises heating tetrafluoroethylene with a satu
drous conditions. However in certain instances,
rated organic compound of at least two carbon
the presence of water may be advantageous to
atoms containing only carbon, hydrogen and oxy
help dissipate the heat of the reaction.
25 gen selected from the class consisting of aliphatic
The reactions may be carried out in any suita
and cycloaliphatic acids, esters and ketones, the
ble reaction vessel, such as stainless steel, iron,
mole ratio of said saturated carbonylic compound
silver, aluminum and other metals and alloys
to said tetrafluoroethylene being from .1 to 10,
which are capable of withstanding heat and pres
said heating being effected in the presence of a
sure. The reaction is preferably carried out with
agitation, although agitation is not always. nec 30 peroxygen catalyst at a temperature within the
essary.
range of from 50° C. to 350° C.
.
The present invention is useful for the produc
tion of a wide variety of organic ?uoro-substi
tuted carbonyl compounds. Although it is under
stood that usually a mixture of compounds with
varying ratios of ?uoroethylene units per car
bonyl molecule is obtained, the mixture can gen;
erally be separated into various de?nite fractions
by various methods such as steam distillation, 40
fractional distillation, extraction and fractional
'
2. The process for obtaining a mixture of tet
ra?uoroethyl carbonylic compounds which com
prises heating tetra?uoroethylene with a satu
rated aliphatic ketone containing only carbon,
hydrogen and oxygen, the mole ratio of said ke
tone to said tetra?uoroethylene being from .1 to
10, said heating being effected under pressure in
the presence of a peroxygen catalyst at a temper- '
ature within the range of from 75° C. to 250° C.
3. ‘The process for obtaining a mixture of tet
crystallization. Products with a given ratio of
ra?uoroethyl carbonylic compounds, which com,
poly?uoroethylene units per molecule of car
»prises heating tetra?uoroethylene with a satu
bonyl compound can often be prepared by the
rated cycloaliphatic ketone containing only car
proper choice of conditions and catalyst. In 45 bon, hydrogen and oxygen, the mole ratio of said
crease in pressure favors an increase in molecular
ketone to said tetrafluoroethylene being from .1
weight and thus a higher ratio of ?uoroethylene
to 10, said heating being effected under‘ pressure
units per molecule of product.
in the presence of a peroxygen catalyst at a tem- The products can readily be distinguished from
perature within the range of from 75° C. to 250° C.
the reactants by analysis and by their physical 50 4. The process for obtaining a mixture of tet—
properties. In general, the specific gravity and
ra?uoroethylcarbonylic compounds, which com
stability of the products increase while the re
prises heating tetra?uoroethylene with cyclohex
fractive index decreases with increase in per
anone, the mole ratio of said cyclohexanone to I
centage of ?uorine in the products. The products
said tetra?uoroethylene being from .1 to 10, said
of this invention vary from liquids to relatively 55 heating being effected under pressure in the pres
low molecular weight solids which usually soften _ ence of lauroyl peroxide at a temperature within
or melt below 300° C. when heated in air on a cop
the range of from 75° C. to 250° C.
per block. The liquid products are generally
5. A mixture of saturated organic tetrafluorow
compatible with the common organic solvents but.
ethyl compounds having the'following general
the solid products have a rather limited solubility 60 formula: ’
in most solvents.v
The reaction and the separation or isolation of
wherein ZH is a saturated organic compound of
the products may be carried out simultaneously
at least two carbon atoms containing only car
or in separate steps. The products may be sepa
bon, hydrogen and oxygen selected from the class
rated by ?ltration, extraction, distillation or crys
consisting of aliphatic and cycloaliphatic acids,
tallization depending upon the nature of the
products.
esters and ketones, and n is an integer between
1 and 25.
.
,
The products of this invention are useful for
6.
A
mixture
of
saturated
organic
tetra?uoro
various commercial purposes. Since all of the
ethyl compounds having the following general
products of this invention are extremely stable, 70 formula:
they are generally applicable for use as solvents
and reaction media. Many of the products have
been found to be very desirable in that they are
wherein ZH is a. saturated aliphatic ketone con
substantially non-?ammable, non-corrosive and
taining
only carbon, hydrogen and oxygen, and n
non-toxic. The saturated organic ?uoro car 75 is an integer
between 1 and 25.
v
2,411,158
11
'7. A mixture of saturated organic tetra?uoro- v
12
8. A mixture of saturated organic tetra?uoro
ethyl compounds having the following general
ethyl compounds having the following general
formula:
formula:
H(CFaCFz)nZ
H(CF2CF2)1:Z
wherein ZH is a saturated cycloaliphatic ketone 5 wherein ZH is cyclohexanone and n is an integer
containing‘v only carbon, hydrogen and oxygen,
between 1 and 25.
and n is an integer between 1 and 25.
-
WILLIAM EDWARD HANF‘ORD.
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