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Патент USA US2387286

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Patented‘ Oct. 23, 1945
‘ . 2,387,286
UNITED STATE 5
PATENT "OFFICE '
2,387,286 .
- SULPHURIZED CARDANOL ETHERS
, Ferdinand r. Otto, Woodbury, N. J., assignor to
Socony-Vacuum Oil Company, Incorporated, a
corporation of New York '
‘
No Drawing. Application November 25, 1943.
Serial No. 511,703
'
'
'
__8-Claims.' (credo-1'25). .'
This invention has to do with new chemical
compounds or reaction products which may be
generally designated as sulphurized cardanol eth
ers or as sulphur-containing reaction products of
cardanol ethers and elementary sulphur.
(
Making use of this term. the following ‘structural
The present invention is predicated upon the
discovery that the compounds or reaction prod
uctsFcontempIated herein when blended with a
viscous mineral oil fraction such as a hydrocarbon
formula represents cardansl ethyl ether
'4
0 CH5
lubricating ,oil, will improve various properties of
I
1
i‘ '
.
the oil.‘ For example, these compounds or reac-"
0101121
tion products will inhibit oxidation of the oil,
thereby retarding the formation of sludge and
acidic products. They also'retard changes in vis
co'sity,‘in the oil, with temperature change during
It is to be understood that all cardanol others
are contemplated herein for reaction with ele
mentary sulphur and'that all organic radicals
may replace the ethyl (,—CaHs) radical. shown
‘It is to be understood, however, that the pres
ent invention is not concerned with mineraloil
compositions, such compositions forming the sub
ject matter of my copending application Serial
No. 424,127, ?led December 23, 1941, ofwhich the
, above. '~ In this resarchthe orsaniclradical may be
alkyl such as methyl; propyl, butyl, decyl, etcyl,v "
20
, representedby methyl phenyl and methyl naph
present application is a continuation~in-part and
thyl, etc.; cycloalkyl as represented by cyclo
p to which reference is made for further details in
the composition of these compounds or reaction
products.
.
octadecyi, etc.; aralhl such as benzyl, etc; aryl
as typi?ed by phenyl, naphthyl, etc.;~ allsaryl as
phenyl; etc.
-
While ‘the. mechanism of the reaction of car-a
danol ethers‘ with elementary sulphur is, as yet.
25
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It is also to be understood that the‘ use of the
compounds or reaction products contemplated
notwhoily understood, it is most probable that
herein is not confined to the improvement of '
sulphur reacts with‘ the carbon atoms of the un
mineral oils. For example, they may be used as
saturated bond of the
cutting oils, rubber accelerators, 'etc., and as in 30 following manner,
termediates in the production of other chemical
1 group —CnH§a-:, in the -
compositions. ‘Numerous other uses and applica- ‘
tions of these compounds or reaction products
will be readih'r apparent to those skilled in the art 1
from the description of their composition and as.
typical methods for preparing them, as provided
hereinafter.
'
wherein R is an organic radical.
=
As aforesaid, the compounds or reaction prod- -
dots of the present invention are obtained by re
action of cardanol ethers and elementary sulphur.
The term “cardariol? as described in U. 5.‘ Patent ,
2,181,119, denotes a phenol ha
an empirical
_
formula oi Gaol-Iss0, and probable structural for
mula of I-ImGmCaHrQOI-I with one unsaturated
bond in the HarzCm-radical, which is meta to the
-OH radical. The ethers of cardanol, or» car
danol ethers, contemplated herein are those in
which the hydrogen of the —OI-l radical has been
replaced by an organic radical, as, for example, an 50
aromatic or an aliphatic radical, with preference
given to the cardan'yl alkyl ethers.
The term “cardanyl" as used herein describes
‘
-
not in any way to be construed so as to limit the ‘
scope of this invention, for the ‘sulphurized car
danol others herein descrimd are contemplated .
broadly as the reaction products of elementary
sulphur and cardanol others.
,
The reactlonproducts contemplated herein are
illustrated by those shown in the following typical
examples.
>
EXPLE 1
Rrmcrron Pnonucr 0am... ' ARY SULPHUR as
‘
I
'
The foregoing suggested expltion oi the re
' .action mechanism is merely speculation and is
CARDANYL Ems Emma
'
One hundred, and sixty- grams of cardanyl '
that group or radical which remains on the re
ethyl ether and 16.2'era'ms of elementary, sulphur.
moval of the —OH group from cardanol, as
were heated in the presence of .a non-oxidizing '
1
' ‘2,887,286
reaction temperatures used therein may be varied
gas‘, such as nitrogen, at approximately 175°, C.
p for a period of 24 hours.
considerably. For example, temperatures in the
During the reaction,
practically no hydrogen sulphide was evolved, an
neighborhood of from about 110° C. to about 200° '
indication that the major portion of the sulphur
C. are satisfactory, but preference-is given to re
action temperatures of the orderoi about 150° C.
reacts withthe unsaturated group of the alkyl
side chain of the cardanyl ethyl ether. A copper
to about 175° C.
.
'.- j
.
' Simila?t, it is preferred to react from about 0.5
to about 2.0 atomic proportions‘ of sulphur with
strip test on a 1 per cent blend of the reaction
product in a mineral oil, heated for ,3 hours at
150° C. gave no appreciable discoloration of the
one mol of cardanyl ether in order to prepare the
copper strip, therefore indicating that all of the 10 reaction products of this invention._ Particularly
preferred products, however, are prepared by re
sulphur had been chemically combined. The
acting one atomic proportion of sulphur with one
product may be improved in color by contacting
it for approximately 1/2 hour with 10 per cent to , mol of a cardanyl ether under the foregoing re
action conditions.
,
20 per cent of superé?ltrol clay, followed by ?l
It is to be further ‘understood that although I
_ tration through more clay to obtain the ?nished 15
product, which is a light brown oil and contains . have described certain preferred procedures for
preparing the reaction products contemplated '
about 9 per cent sulphur.
herein and have shown illustrative reaction prod
ucts, the invention is not limited to the particular
Rnaorron Pnonucr or Erasmus“ Super-run m 20 procedures or products, but includes within its
EXAMPLE 2
CARDANYL Ocranrcrr. Erma
_ scope such changes and modi?cations as fairly
(a) Preparation of cardanyl octadecyl ether
come within the spirit of the appended claims.
I claim:
reaction mixture
-
Cardanol
_
'72
n-Octadecyl chloride _________ __'__- _______ __
I
1.- As a new composition of matter, an oily, sul
25 phur-containing reaction product obtained by re
action of a cardanol ether and elementary sul
Grams
72
phur.
Sodium dissolved in 150 cc. of butanoi _____ __ 5.8
‘
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2. As a new composition of matter, an oily, sul
phur-containing reaction product obtained by re
The cardanol was added to the stirred solution 30 acting a cardanol ether and elementary sulphur
at a temperature between about 110° C. and about
of sodium butylate to. form the corresponding so
, Procedure
-
.
200° C.
dium cardanolate. Octadecyl chloride was then
_ 3. As a newcomposition of matter, an oily, sul
i added and the mixture was heated for 14 hours
phur-containing reaction product obtained by re
at 120° C. in an atmosphere of nitrogen. The
butanol was then allowed to distill from the mix 35 action of from about 0.5 to about 2.0 atomic pro
.‘portions of elementary sulphur and about 1.0 mol
ture and the temperature was gradually raised to
of a cardanol ether at a temperature between
200° C. After heating for 5 hours at this tem
about 110° 0. and about 200° C.
perature the product was cooled, diluted with
4. As a new composition of matter, an oily, sul
benzol, acidi?ed with dilute hydrochloric acid.
and water washed until neutral. The mixture 40 phu‘r-containing reaction product obtained by re
acting a cardanyl alkyl ether and elementary
was then topped under diminished pressure to
sulphur at a temperature between about 110° C.
340°~ C. to remove unreacted cardanol vand octa
decyl chloride.
and about 200° C.
The residue, representing the
sulphur reaction mixture
portions of elementary sulphur and about 1.0 mol
.Grams
of a cardanyl alkyl ether at a-temperature be
tween about 110° C. and about 200° C.
50 _6. As a new composition of matter, an oily, sul
Cardanyl octadecyl ether_________________ __ 50
'
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'
3
' phur-containing reaction product obtained by re
Procedure
The cardanyl, octadecyl ether (prepared in
(a)) and sulphur were heated, with stirring, for
a period of 3 hours at 170° C. in the presence 0!
a non-oxidizing gas such as nitrogen.
action of cardanyl ethyl ether and elementary '
sulphur at a temperature between aboutv 150° C.
and about 175° C.
so
The re
action mixture .was then ?ltered to obtain the
?nished compound. 'A polished copper strip, im
mersed in a one per‘ cent blend of the productin '‘
mineral oil, showed no discoloration after heating
for 24 hours at 100° 0.. thereby indicating that
all the sulphur was chemically combined.
The ’
_
,
The preparation of typical reaction products
shown above is but illustrative inasmuch as the
‘
,
>
'1. As a new composition of matter, an oily, sul
phur-containing reaction product obtained by re
action of one mol of cardanyl ethyl ether and one
atomic proportion of elementary sulphur at about
175° C.
'
'
. -
8. As a new composition or matter, an oily, sul
sulphurized cardanyl octadecyl ether is a viscous
brown 011 containing 5.9% sulphur.
‘
45 phur-containing reaction product obtained by re- ‘
action of from about 0.5 to about 2.0 atomic pro
(b) Reaction product of (a) and elementary
Sulphur
'
5. As a new composition of matter, an oily, sul
cardanyl octadecyl ether, was a ?uid brown oil.
phur-containing reaction product obtained by re.
action of one mol of cardanyl octadecyl ether and
one atomic proportion oi‘ elementary sulphur at
about 170° C.
4
FERDINAND P. UI'TO.
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