US 2110274 A
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Patented Mar. 8, 19 38 2,110,274 LIGHT STABILIZER- FOR HYDROCABBONS I 7 Louis A. Mikeska, Elizabeth, and John B. Holtzclaw, Roselle, N. J., assignor's to Standard'0il Development Company, a corporation ware of Dela- No Drawing. Application May 25, 1935,
This invention relates to the improvement of come these difliculties by adding to the fuels, small but efiective quantities of oil soluble aliphatic or aromatic alcohol amine esters, or ethers.
These esters may be obtained by the action of the corresponding acids, acid chlorides, acid an-v hydrides or other compounds which give esters or' ethers, by reacting with aliphatic or aromatic hydroxyamines as, for example, according to the following equation:
value from 1 toil.-
' The products formed according to this reaction are generally recovered as the salts of the acid employed in the esterification. These salts may be neutralized with weak bases, if it be so desired, in order to produce the free amines for use according to this invention. However the salts J themselves may be-employed for the same purpose,
and it is our intention toemploy such salts or even salts containing different acid groups than those where R and R are aliphatic or cyclic radicals, while a: is any value from 0 to 2, and n is any' present in the ester radicals, as exemplified by the formula (ROOR') nNHxHR" where HR may 0' be an aliphatic or cyclic carboxylic acid or phenol.
The hydrocarbon radicals R and Rf may be either normal or branched. I Although any aliphatic hydroxy compound may be employed as a raw material, it is preferred to use the water-soluble amines, suchas the ethanol amines, propanol amines and the like, because of their effectiveness in stabilizing fuels.
In the case of the polyhydroxy alkyl amines, it is possible to esterify sufilcient hydroxy groups to make the products oil-soluble, thereby often leaving some free hydroxy groups in the molecule, although it is preferable to esterify all the hydroxy groupsso as to produce a more stable compoimd. Examples of the materials suitable for the purposes of the present invention are: triacetoxy-- triethanolamine (CHsCOOCHzCHahN, triacetoxy-triethanolamine laurate, tripropionyl-tripropanolamine .0 amine phenolate, acetlyated triethanolamine salts benzoate, dibenzoyl triethanolof hydroxylstearic acid or of tertiary butyl phenol. Tributyryl, divalyryl, mono-oleyl and distearyl and similar esters of triethanolamine and similar compounds may also be used.
These compounds may be added to the fuels in proportions of 0.01% to 0.5% depending on the stability of the fuel and the effectiveness of the inhibitor.
In the case of triacetoxy-triethanolamine in a freshly prepared cracked U. S. grade motor gasoline, the quantity of inhibitor employed to give satisfactory results was in the neighborhood of 0.05%.
The alcoholamine esters herein described may be employed to stabilize gasolines, naphthas, kerosenes and similar products with boiling ranges up to 650 F.
For instance, gasoline rich in cracked products, benzol or other cyclic materials, such as the fuels prepared by' vapor phase or liquid phase crack ing of petroleum oils or coal tar oils, are satisfactorily stabilized according to this invention.
Blended fuels as, for example, gasoline containing alcohols, metallo-organic anti-knock compounds, dyes, lubricating agents, soaps, thickeners and the like may also be treated in the same 8011.000H+(HOOH,CH,);N (OH|O0.0OHIOHmN+aHIO trlaootoxytriothanolamino mm Y A cracked gasoline was blended with varying quantities of triacetoxytriethanolamine and ex-.
posed to the sunlight in 4 oz. sample bottles together with a blank sample of the same gasoline. The following results were obtained after the exposed sample stood for six months:
I Sample I Color Residue 283" Odor Sweet. I
s s b Dark reddish brown. Wat! white.
Original gasoline.-- Bcm e+0.1% inhibr. Bambi- .2% inhlbitor.
These tests show the exceptional stabilizing prop.-
erties of the inhibitors prepared according to the invention.
It will be understood that the invention is not limited to the description given above nor to the examples cited, and other acids and other hydroxya'mines may be used to prepare other esters and other compounds of the same general type as those shown in the equation which has been given.
The invention is not to be limited to any theoretical statements which have been presented herein solely for purposes of illustration, but is limited only by the following claims in which it is intended to claim all novelty insofar as prior art permits.
1. The process of stabilizing a hydrocarbon liquid which comprises adding thereto approximately 0.01 to 0.5% of a substance selected from the group consisting of esters having the general for- 'mula (RCOOR )7lNHI, in which R is an aliphatic or aromatic hydrocarbon radical and R is an aliphatic hydrocarbon radical while a: is any value from to 2 and n is any value from 1 to 3.
2. The process of stabilizing motor fuels which comprises adding thereto approximately 0.01 to 0.5% of triacetoxytriethanolamine.
3. The process of stabilizing motor fuels which comprises addingthereto approximately0.01 to 0.5% of tripropionyltrihydroxy-trialkylamines.
' 4. The process of stabilizing motor fuels which comprises adding thereto approximately. 0.01 to 0.5% of tributyryltriethanolamine.
5. A hydrocarbon fuel which has been stabilized against deterioration by the action of light by adding thereto approximately 0.01 to 0.5% of a.
substance selected from the group consisting of esters having the general formula gacooaomm,
in which R is an aliphatic or aromatic hydrocarbon radical and R is an aliphatic hydpcarbon radical while a: is any value from 0 to 2 and n is any value from 1 to 3.
6. A hydrocarbon fuel which has been stabilized against deterioration/bythe action of light by '(RCOOR')nNH.-c and in which R is-an aliphatic or aromatic hydrocarbon radical and R is an aliphatic hydrocarbon radical, while a: is any value from 0 to 2 and n is any value from 1 to 3.
10. A hydrocarbon fuel which has been stabilized against deterioration by the action ofllght by adding thereto approximately 0.01 to 0.5% of a substance selected from the group consisting of esters having the general formula (RcooRomra,
and in which R is an aliphatic or aromatic hydrocarbon radical and R is an aliphatic hydrocarbon radical, while a: is any value from 0 to 2, and n is any value from 1 to 3.
LOUIS A. MIKESKA. JOHN B. HOLTZCLAW.