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Patent 1165314 Summary

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(12) Patent: (11) CA 1165314
(21) Application Number: 386034
(54) English Title: STABILIZATION OF HYDROCARBON OILS WITH CERTAIN DIHYDROXY COMPONENTS
(54) French Title: STABILISATION D'HYDROCARBURES LIQUIDES A L'AIDE DE CERTAINS CONSTITUANTS DIHYDROXYLES
Status: Expired
Bibliographic Data
(52) Canadian Patent Classification (CPC):
  • 253/124
(51) International Patent Classification (IPC):
  • C10M 129/14 (2006.01)
(72) Inventors :
  • HUTCHISON, DAVID A. (United States of America)
(73) Owners :
  • ATLANTIC RICHFIELD COMPANY (United States of America)
(71) Applicants :
(74) Agent: OSLER, HOSKIN & HARCOURT LLP
(74) Associate agent:
(45) Issued: 1984-04-10
(22) Filed Date: 1981-09-16
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): No

(30) Application Priority Data:
Application No. Country/Territory Date
210,427 United States of America 1980-11-25

Abstracts

English Abstract


STABILIZATION OF HYDROCRACKED OILS WITH
CERTAIN DIHYDROXY COMPONENTS

ABSTRACT OF THE DISCLOSURE

Hydrocracked lubricating oils are effectively
stabilized against deterioration caused by light by the
inclusion of at least one of certain dihydroxy components.
Such component, e.g., 3,5-di-tert-butyl catechol and 4,6-
di-tert-butyl resorcinol, provide outstanding inhibition
to sunlight deterioration.


Claims

Note: Claims are shown in the official language in which they were submitted.



The embodiments of the invention in which an
exclusive property or privilege is claimed are defined
as follows:
1. A composition of matter comprising a
major amount by weight of a hydrocracked lubricating
oil and a minor amount by weight of at least one added
dihydroxy component having a structure:

Image

wherein each R is independently selected from the
group consisting of substantially monovalent hydrocarbonaceous
radicals containing 1 to about 24 carbon atoms, and
a and b are integers such that a is equal to at least
2 and the sum of a plus b equals 4.
2. The composition of claim 1 wherein said
hydrocracked lubricating oil comprises at least about
70% by weight of said composition.
3. The composition of claim 2 wherein said
R's are independently selected from the group consisting
of substantially aliphatic hydrocarbonaceous radicals.
4. The composition of claim 2 wherein said
added dihydroxy component comprises about 0.005% to
about 2.0% by weight of said composition.

5. The composition of claim 3 wherein said
dihydroxy component comprises about 0.01% to about
1.0% by weight of said composition.

6. The composition of claim 3 wherein a
is equal to 2 and said dihydroxy component comprises
about 0.01% to about 1.0% by weight of said composition.



7. The composition of claim 3 wherein said
R's are substantially saturated.
8. The composition of claim 6 wherein each
of said R's includes at least one tertiary carbon
atom.
9. The composition of claim 3 wherein each
of said R's has the same structure and contains 1
to about 10 carbon atoms.
10. The composition of claim 8 wherein each
of the R's is tertiary butyl.
11. A method of inhibiting a hydrocracked
lubricating oil from deterioration caused by sunlight
comprising combining with said oil an inhibiting amount
of at least one dihydroxy component having a structure:

Image

wherein each R is independently selected from the group
consisting of substantially monovalent hydrocarbonaceous
radicals containing 1 to about 24 carbon atoms, and a
and b are integers such that a is equal to at least 2
and the sum of a plus b equals 4.
12. The method of claim 11 wherein
said R's are independently selected from the group

consisting of substantially aliphatic hydrocarbonaceous
radicals.


13. The method of claim 11 wherein said
dihydroxy component comprises about 0.005% to about
2.0% by weight of said composition.
14. The method of claim 11 wherein said
dihydroxy component is present in an amount equal
to about 0.01% to about 1.0% by weight of said composition.
15. The method of claim 12 wherein a is
equal to 2 and said dihydroxy component comprises
about 0.01% to about 1.0% by weight of said composition.
16. The method of claim 12 wherein said
R's are substantially saturated.
17. The method of claim 15 wherein each
of said R's includes at least one tertiary carbon
atom.
18. The method of claim 16 wherein each
of said R's has the same structure and contains 1
to about 10 carbon atoms.
19. The method of claim 17 wherein each
of said R's is a tertiary butyl radical.


Description

Note: Descriptions are shown in the official language in which they were submitted.



The in~ention rel~te~ ~o a method of ~tabilizing
d hydroc~a~ked oil~ ~ore particularly 7 ~t relate~
ts ~t~bil izinq ~c~ ga~t light de~eri~ration
~y ~dding there~ a l~as~ one Q~ certain ~i~ydroxy-


components.
~ t i8 ~tlDWll that Dils in qeneral will degrade~l~wly in the pre~ence of light. Oil~ ~uch as ~he
~c~nomica~ly v~lu~ble hydrocra~ed lubricating oils
used in hi~ invention, degrade in li~ht, especially
in the Dre~ence of air. Since the hydrocracked oils
are valuable, there has been considerable effort to
~ind ways to prevent their breakdown due to light.
U.S. Patent 4,036,770 ~eaches a method for
stabilizing hydrocracked oils which in~olves a~din~
nitro-containing aromatic amine c~mponent~. Such com~onents
~re relatively expensive and therefore m~y ~dd significantly
to the cost of the hydrocracked oils, Also~ such r~mponents
m~y impart a less than desirable ~olor an~/or odor to the final
product.
U~S. Patent 4,101,430 teache~ that oxidative
~egradation of lu~ricant co~po~ition6 containing certain
organo ~ulfur-c~ntaining nickel complexe~ is inhibited.

U.S. Patent~ 2,78~,18~ and 3,156,543 teach
the use ~f 3,3',5,5'-tetra alkyl-4t4~dihydroxy diphenyls
as o~idation ~tabilizer~ f~r hydr~Garbon fuels, ~uch
as gasoline. U.5. Pate~t 3,156,543 discloses ~ha~
~,4'~ (2-i~oprop~1-6 tert-butylphen~ s a light
yellow crystalline ~ub~thnce ~nd i~ highly soluble
in gasoline, ~iesel fuel and lu~ricating oil. ~owever,
~either of the~e xeferences teach either inhlbiti~

~f ~eterior~tion from livht expvsure ~r hydrocracked
lubricatiQg oil~.


~6,'~


One ~ject of the present inventi~n ih to
pr~Yide an improved me~hod for ~tabilizin~ hydrocracke~
lu~ricating ~ gain~ e aeteriorating effects
Df light~
AnDther object Or the inventi~n i~ -to provi~e
an impr~e CDm~iti~n o~ matter in~olvin~ a hydrocracked
?ubricating ~i~ ~hich has improved inhibi~ion again~t
deteriorati~n by light, Othes ~jects and advantages
Df the present invention will ~ecome apparent hereinafter.
An improved hydrocracked oil compo~ition
ha now been discovered. This com~osition comprises
a major amount, preferably at least about 70%, by
weight of a hydrocracked lubricating ~il an2 a minor
amoun~ by weigh~ ~f at least one added dihydroxy
~omponent havin~ a 6tructure:
;
lOH ,


(H)b 3_OH
~R) a




wherein each R is in~ependently selecte~ from the group
consisting o~ ~ubstantially monovalent hydrocarbonaceous
radicals containing 1 to abollt 24, pre~erably 1 to-
~be~ut 1~ and more prefer~bly 1 to about 10, carbon
atoms; and a and b are integers such that a is e~aual to
at least 2, preferably equal to 2, and the sum of a plus
b equals 4.
~ t is preferred that th~ hydrocarbonaceous
radical ~e ~ubstantially ~atura ed aliphatic radicals.


~ ~ 6~


Also, it is pxeferred that each of the R qrou~s include
at least ~ne textiary carbon atomO More preerably,
each of the R sroups has the same structure and, still more
preferab~y, each of the R groups i.s a tertiary butyl
group.
In a preferred emboaiment, the a~de~ dihydroxy-
diphenyl component compri~es about O . 005~ to ~bout 2 . 0%
more preferably, ab~ut 0.01% to about 1. 0%, by weight of
the total composition.

lQ The term "hydrocracked lubricating oil~ means
an oil, preferably a mineral oil, of lubricating viscosity
which is derived from a lubricating oil produced by
contac~ing a hydrocarhon feédstoc~ with hydrogen, preferably
: in the presence of ca~alyst effective to promote hydro
cracking, at hydrocarbon hydrocracking conditions to
~: produce an oil of lubricating viscosity having an increased
viscosity index relative to the visc~sity index of
: the hydrocarbon feedstock. In addition, the
hydrocracked lubricating oll may be subjected ~o addi~ional
processing, e.g., further contacting with hydrogen-
~: a~ain preferably in the ~resence of an effective catalyst-~
other purifying procedures and the like, to further
: ~mprove the guality, e~g~ 9 color, of the hydrocracked
lu~ricatinq oil, For example, hydrocracked lubricatin~
oils useful in the present inventi~n may be obtaine~
by the processes disclosed in U.S. Patent 3,642J610.
~ ypical examples of the ~ubstantially monovalent
hydrocarb~naceous radical~ from which R may be selected
incluaes alkyl,such a~ methyl, ethyl, propyl, butyl,

pentyl~ hexyl gincluding cyclohexyl), 05tvl, decyl,



the like; ~yl, ~uch ~ phenyl~ benzyl and the like;
alkaryl ~u~h a~ ~ethy~ phenyl, ethyl phenyl, butyl
phenyl, octyl ph~yl, ~ea~l phenyl And ghe like;
alkenaryl ~ch ~ e~hylenyl phenyl, octenyl phenyl,
oleyl phenyl and the like; ~ralkyl ~uch as ph~nyl ethyl,
phenyl o~tyl, phen~l stearyl a~d *he like; and ar~lkenyl
~uch as phenyl ~thylenyl, p~enyl butenyl, phenyl octenyl,
phenyl oleyl and ~he like. ~s no~ed above, it is preferred
that such hydrocarbonaceous radical~ be substantially

10 ~aturated.
By n substantially hydrocarbonaceo~s~ radical
is meant those radical~ which are comp~sed
mainly of hydro~en and carbon, and include such radicals ;~
which contain, in addition, minor amounts of ubstituents,
such as chlorine, bromine, ~ulfur, nitrogen and the
like, which do not substantially affect their hydrocarbon
characterO Preferably, such substantial.ly hydrocarbonaceous
radical~ include only ~rbon ~nd hydrogen ~toms.
The presen ly useful dihydroxy component m~y
be produced using procedures well known in the art.
The following example~ illustrate ~ore ~lear~y
the compositions and methods Df the present invention,
~owever, the6e illustra~ion~ 2re not to be interpreted
~pecific limitationfi on this inventicn.
EXAMæLES
These exam~les illustrate certain of the advantages
of the present invention.
A commercially available hydrocracked oil of
lubricating viscosity was selected for testing.
~his hydrocracked oil had the following properties.
Initial Boiling Point, F. ;~ 600
Viscosity, SU5 at 100~. 156.0

Viscosity Index 106

t~

This oil was deriv~d using a well known lube oil hydrocracking
process.
Varying amounts of 3~-di-tert-~uty~ catechol
were blended into samples of the hydrocracked ~il.
In order ~o ~etern~ine .he susce?tibi~.ity
~f the oils ~n~ ~len~ to lig~t deterioration, 10 gram
~amples were p~aced In ~5D ml. beaker~ ana exposed
to tw~ 12) 275 watt ~.V~ ~unlamps at se~en(7) in~hes
~n a r~tating table ~r a period of fifteen (15) hours.
After the fifteen (15~ ~our exposure periodr each of
the samples was processed to determine the amount of
E~l~ds Isludge) formation. The followi~ results were
obtained:

ydrocracked Oil 3,5-di-tert- Solids ~fter Exposure
butyl catechol mg.~ oil
weight percent

Sample 1 0.00 1.23
2 0.01 1.01
20 3 0.025 0.94
4 ~.05 ~.77
0.10 0 55
6 0.15 0.36
7 0.20 0.30
8 0.40 ~.16
9 0.70 0.~8
1~ ~.00 0.07
A series of fi~e additional compositions were
blended using the hydrocracked oil noted abo~e and 4,6-

di-tert-~utyl resorcinol. These five compositions were

tested using the above described procedure and the following
results were obtained:


~6~3~


4,6 di-tert- ~Glids After Exposure
buty~ re~orc~nol _ m~ m. oil
~ . .
0.20 0.43
1~ 0.40 ~.11
12 0.60 0.02
13 0.~0 0.00
14 ~.0~ 0.01


These results indicate that hydrocracked lubricating

oll alone is susceptible: to deterioration by sunlight.
~ he dihydroxy components, as set forth in the
present in~ention, are shown to provide ~ubstantial inhibition
of deterioration of hydrocracked oil by sunlight.
In addition, such dihydroxy components impart little or
no distaste~ul odor ~o the hydrocracked oil compositions.
This is in significant contrask to ~and is a substantial
benefit relative to) compositions which include various
of the nitrogen-containing materials which have been suggested
20 ~y the prior art for inhibiting light deterioration of h
hydrocxacked oils~ .
. While this invention has been described with
respect ~o various specific examples and embodiments, it
is to be understood that the inventisn is not limited thereto
: ~ and that it can be variously pra~ticed within the ~cope
~ f the fO11DWing claims:

Representative Drawing

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Administrative Status

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Administrative Status

Title Date
Forecasted Issue Date 1984-04-10
(22) Filed 1981-09-16
(45) Issued 1984-04-10
Expired 2001-04-10

Abandonment History

There is no abandonment history.

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Application Fee $0.00 1981-09-16
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
ATLANTIC RICHFIELD COMPANY
Past Owners on Record
None
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
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Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Description 1993-12-02 6 251
Drawings 1993-12-02 1 21
Claims 1993-12-02 3 95
Abstract 1993-12-02 1 17
Cover Page 1993-12-02 1 20