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Publication numberUS2844448 A
Publication typeGrant
Publication dateJul 22, 1958
Filing dateDec 23, 1955
Priority dateDec 23, 1955
Publication numberUS 2844448 A, US 2844448A, US-A-2844448, US2844448 A, US2844448A
InventorsRobert Y Heisler, Stanley R Newman, Alpert Norman
Original AssigneeTexas Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Fuels containing a deposit-control additive
US 2844448 A
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Description  (OCR text may contain errors)

. lines which burn cleanly,

United States Patent- FUELS CONTAINING A'DEPOSIT-CONTROL ADDITIV E Robert Y. Heisler and Stanley R.

Norman Alpert, Pougbkeepsie, Texas Company, Delaware No Drawing. Application December 23, 1955 Serial No. 554,925

13 Claims. (Cl. 44-70) Newman, Fishkill, and

tained by the addition of a minor amount of a polyglycol carbonate ester of prescribed composition.

As automobile manufacturers annually raise the compression ratioof their automobile engines in therace for' higher horsepower, the need becomes :greaterforgasothat is, have lowv deposit-forming tendencies. Engine deposits-which findtheir. origin in the fuel are primarily responsible for surface ignition phenomena such as preignition. and "octane requirement increase (ORI) which is the tendency of spark ignition engines inIservice to require higher octane fuels *for'proper performance. As a consequence, gasoline manufacturers have'placed increasing stress on reducing the :depositforming tendencies of their. fuels andhave resorted to various additives either to reduce theamountof deposits or to minimize their effects. The present invention involves the discovery that a particular class of polyglycol derivatives are outstanding in controlling the depositforming tendencies of hydrocarbon fuels.

The improved hydrocarbon fuels-of this invention'contain a polyglycol carbonate ester of the general formula ROOCO (R0 COOR" wherein R is a divalent aliphatic radical containing-at least 2 carbon atoms, R and R are aliphatichydrocarbon radicals containing between 3 and 18 carbon atoms and n is an integer having a value of at least 2, in an amount sufiicient to reduce the deposit-forming tendencies of the fuels. The polyglycol carbonateester is effective in the motor fuel in concentrations as low as 0.01 volume percent but concentrations of 0.04 to 0.3 volume percent are normally employed. There is no critical upper limit of concentration, but economic considerations'dictate that concentrations less than 1.0 volume percent polyglycol carbonate be present in the fuel.

The polycarbonate esters which inhibit the depositforming tendencies of hydrocarbon fuels arereadily formed by a series of reactions involving the formation of an alcohol chloroformate by reaction of phosgene with an alcohol and subsequently reacting the alcohol chloroformate with a polyglycol in thepresence of a hydrogen chloride acceptor, such as pyridine or quinoline. An alternate reaction procedure involves formation of a polyglycol dichloroformate by reaction of polyglycol with phosgene and subsequent reaction of polyglycol dichloroformate with an aliphatic alcohol in the presence of .a hydrogen chloride acceptor. The preparation of compounds of this type is disclosed in U. S. Patents 2,370,567 and 2,370,569.

The hydrocarbon fuels of this invention are characterized by low deposit-forming tendencies with theresult that an engine operated therewith shows exceptionally clean intake system, combustion space, valves, ring belt' area and injection system if a diesel engine; Thelow deposit level in the engine minimizes surface ignition in all its.manifestations,.mainlypreignition and knock. In

N. Y., assignors to The New York, N. Y., a corporation of wherein R'is a divalent aliphatic radicalcontaining at TABLE I Approximate Molecu- Weight Boiling lar Wt. C to 0 Point, Ratio Ethylene glycol bis (allyl carbonate) 560 230 2. O0 Diethylene glycol bis (allyl carbonate). 660 274 1. 57 Diethyleneglycolbis(n-amylcarbonase). 720 334 1. 71 Diethylene glycol his (methyl atnyl carbonate) I 700 362 1.93 Tetraethylene glycol bis (allyl carbonate 790 362 1.33 Tetraethylene glycol bis (2-ethylhexyl carbonate 506 2. 18 Tetraethylene glycol bis(amyl' carbonate 795 422 1: 67 Polyglycol (av. mol Wt. 300) bis(2-ethylhexyl carbonate) 644 2.05 Polyglycol (av. mol wt. 400) bis (Z-ethylhexyl carbonate) 744 1. Diethylene glycol bis(n-buty1;carb0n-' ate) 670 306 1. 50-

2,844,448 Patented July 22, 1958 addition, the low deposit level reduces the engines octane requirement increase. In addition, deposits on surfaces contacted'by the lubricating oil, such as piston skirts and cylinder walls, are very markedly reduced.

Polyglycol carbonate esters usable in the process of the invention are exemplified by the following: diethylene glycol bis(allyl carbonate), triethylene glycol bis(allyl carbonate), tetraethylene glycol bis(allyl carbonate), diethylene glycol bis(n-amyl carbonate), triethylene glycol bis(n-amyl carbonate), tetraethylene glycol bis(namyl carbonate), dipropylene glycol bis(n-amyl carbonate), polyglycol (av. mol wt. 300) bis(n-amyl carbonate), polyglycol (av. mol wt. 400) bis(Z-ethylhexyl.carbon-. ate), tetraethylene glycol bis(2'-ethylhexyl carbonate), diethylene glycol bis(2-ethylbutyl' carbonate), diethylene glycol"bis(n-propyl carbonate), polyglycol (av. mol. wt.

400) bis(n-amyl carbonate), diethylene glycol bis(4- pentenyl carbonate), tripropylene glycol bis(2-ethylhexyl carbonate), diethylene glycol bis(isoamyl. carbonate),v


least 2 carbonatoms, R and R" are aliphatic hydrocarbon radicals containing at least 3 carbon atoms and: n isan integerhaving a value of at least2, are ineffective as deposit-control additives in hydrocarbon fuels. example, a monoglycol carbonate ester such as ethylene glycol bis(allyl carbonate) is ineffective while diethylene glycol carbonate esters such as diethylene glycol bis(allyl carbonate) are excellent deposit-control additives. Similarly, diethylene glycol-bis(ethy1 carbonate) is ineffec-- tive in controlling deposits while diethylene glycol bis (allyl carbonate), is a very good deposit-control additive.- As a result of intensive experimentation, the following generalizations have been made with regard to the properties required for a glycol carbonate ester to exhibit deposit-control properties.

The polyglycol carbonate esters that are effective in' reducing the deposit formation in hydrocarbon fuels are all characterized by boiling points above 650 F.', a. molecular weight above 270 and a carbon-to oxygen ratio by weight below 2.50. Apparently, the polyglycol care bonate ester must possess all of these properties simultaneously in order to impart deposit-control properties to hydrocarbon fuels. In Table'I below the boiling point,

molecular weight, and C to 0 ratio by weight for eifec tive and inelfective glycol carbonate esters are shown.

- Not distilled- -too high boiling.


In summary, the following conclusions can be made as to the requirements of each section of the additive molecule for the production of a glycol carbonate ester having deposit-control properties. The alkylene oxide unit, that is the (RO),, group, must contain at least 2 units; as many as 2 to repeating units can be used in this portion of the molecule; ethylene oxide and propylene oxide derivatives are preferred from the standpoint of cost, availability and effectiveness. Two carbonate radicals are required since polyglycol mono carbonate ester compounds are ineffective as deposit-control additives. The terminal aliphatic radicals must contain at least three carbon atoms; aliphatic radicals containing 3 to 10 carbon atoms are preferred. In both the alkylene oxide group and in the terminal aliphatic radicals, straight chain radicals are preferred to the branched chain hydrocarbon radicals although if the overall molecule is large, moderate branching can be tolerated. Similarly, primary alkyl carbonate esters are preferred to secondary and tertiary carbonate esters.

As a general rule, longer chain terminal radicals are combined with polyglycols containing a larger number of repeating alkylene oxide units while lower molecular weight terminal aliphatic radicals are combined with polyglycols containing a small number of repeating alkylene oxide units. Thus, a 2-ethylhexyl terminal radical is preferably used in the formulation of a tetraethylene glycol carbonate ester than in the formulation of a diethylene glycol carbonate ester. Formulating the polyglycol carbonate esters following this general rule assures that the resulting additive has a carbon to oxygen weight ratio less than 2.5.

The polyglycol carbonate 'ester is effective as a depositcontrol additive in concentrations between 0.01 and 1.0 volume percent of the fuel. Generally, dirtier fuels having a higher concentration of olefinic components require higher concentrations of the polyglycol carbonate ester whereas cleaner burning premium fuels are improved with respect to desposit-forming characteristics by smaller concentrations of the polyglycol carbonate ester. In general, dirtier gasolines require a polyglycol carbonate ester concentration between 011 and 0.3 volume percent whereas clean-burning premium fuels only need a polyglycol carbonate ester concentration of between 0.01 and 0.08 volume percent. As indicated previously, there is no critical upper limit from a functional viewpoint but economics dictate that the polyglycol carbonate ester concentration be less than 1 volume percent.

The polyglycol carbonate esters of the type described in this invention are effective in controlling deposits in hydrocarbon fuels having boiling points up to about 700 F., although benefits also result when the polyglycol carbonate esters are added to fuels containing residual stocks of higher boiling point. The major application of the additive is in gasoline for automotive engines wherein fuel-derived engine deposits have become a particularly vexing problem. The deposit-forming properties of diesel fuels and fuels designed for use in jets and gas turbines are also improved by the polyglycol carbonate esters of this invention. In diesel fuels the presence of the polyglycol carbonate ester maintains the injection system and combustion zone in a clean condition. This is particularly important with the increasing use of the so-called economy diesel fuels, that is fuels having a high sulfur content or containing cracked or residual stocks. P olyglycol carbonate esters find particular applicationin jet fuels which are used as cooling mediums prior to their consumption. A polyglycol carbonate ester containing jet fuel is an excellent heat exchange medium sinceit is relat-ively free from deposits in the cooling system and burner nozzle where deposits cannot be tolerated.

The deposit-forming properties of both regular and premium gasolines, both of the leaded and of the nonleaded type, are improved by the addition of polyglycol carbonate esters. The gasolines to which the polyglycol carbonate esters are added can be broadly defined as a hydrocarbon fuel having a boiling point up to approximately 400 F.

The action of polyglycol carbonate esters of the prescribed composition in controlling the deposit-forming tendencies of motor fuel was demonstrated by a Modified Chevrolet Deposits Test-CRC FL-2-650. The laboratory engines are operated under the standard conditions of this test with the except-ion that crankcase oil temperatures were 10 F. lower, the water jacket temperatures were 5 F. lower, and the crankcases of the test engines were ventilated. These modifications are in every case in the direction of making the test more severe and are intended to simulate low temperature conditions wherein deposit formation is most pronounced. After the termination of each run, the engine is disassembled and its parts are evaluated by a merit system adapted from the CRCL-41252 Test. This merit system involves visual examination of the engine part in question and their rating according to deposits by comparison with standards which have assigned ratings. For example, a rating of 10 on piston skirt designates a perfectly clean piston while a rating of zero represents the worst condition. Similarly, a rating of on total engine deposits represents a perfectly clean engine, etc.

In Table II there is shown the decrease in deposit formation resulting from the addition of various polyglycol carbonate esters to a high quality regular grade gasoline comprising a mixture of thermal cracked stock, fluid catalytically cracked stock and straight run gasoline. This regular base fuel had an 87.0 ASTM Research octane rating, contained 2.90 ml. of TEL per gallon, had an API gravity of 58.0 and a boiling range between 106 F. and 936 F.; the. base fuel was negative in the copper corrosion test and had an oxidation stability in the ASTM test of 530 minutes minimum. The reference fuel also contained minor amounts of gasoline inhibitors, namely N ,N-disecon-dary butyl-p-phenylenediamine, lecithin, and N,N-disalicylidene-l,2-diarninopropane. In all the runs in Table II, the laboratory engines in the Chevrolet S-II test were lubricated with Advanced Custom Made Havoline, a heavy duty type oil meeting Supplement I require- \ments and manufactured 'by The Texas Company.

In Table II the concentration of additives in the base fuel was 011 volume percent in each instance.

TABLE II Piston Total en- Skirt gine deposits Base fuel 4. 7 77. 7 Base fuel plus the following:

Ethylene glycol bis(allyl carbonate) 3. 5 70. 5 Diethylene glycol bis(allyl carbonate) 8. 5 84. 5 Triethylene glycol bis (allyl carbonate) 8. 7 86. 7 Tetraethylene glycol bis(allyl carbonate) 9. 2 89.2 Diethylene glycol bis(amyl carbonate) 8. 8 87. 8 Tetraethylene glycol bis(amyl carbonate) 7. 5 82. 5 Diethylene glycol bis(n-butyl carbonate) 8. 5 87. 5 Diethylene glycol bis(2-ethylhexyl carbonate). 5.8 80. 8 Polyglycol (av. mol wt. 300) bis(Z-ethylhexyl carbonate) 9. 3 91. 3 Tetraethylene glycol bis(2-ethylhexyl carbonate 6. 8 84. 0 Triethylene glycol bis(allyl carbonate). 8. 7 86. 7 Triethylene glycol bis (amyl carbonate) 9. 0 91.0 Polyglycol (av. mol wt. 400) bis(2-ethylhexyl carbonate) 8. 7 87. 7 Polyglycol (av. mol wt. 300) bis(amyl carbonat 9. 5 89. 5 Polyglycol (av. mol wt. 400) bis(amylcarbonate) 9. 2 87. 2

The data in the above table clearly show that a polyglycol carbonate ester of the prescribed formula is necessary in order to producea motor fuel of decreased depositforming tendencies. Ethylene glycol bis(allyl carbonate) gave a dirtier piston skirt and a dirtier total engine rating than the base fuelwhereasdiethylene glycol bis(allyl car- 'bonate) substantially improved boththe piston skirt and totalengine rate. ,It isfalso significant that higher molecular weight alkyl radicals in the carbonate ester are "advantageously com- 6 of N,N'-disecondary butyhp-phenylenediamine, a gum inhibitor, per thousand barrels of gasoline, about 1.2 pounds of N,N'-disalicylidene-1,Z-diaminopropane, a metal deactivator, per thousand barrels of gasoline, and

bined with polyglycols of a large number of alkylene 5 about 1.1 pounds of lecithin, a tetraethyl lead stabilizer, oxide units than with lower molecular weight polyglycols. per thousand barrels of gasoline. This result is'evident'from' a'comparison of the ratings TABLE Iv obtained with diethyleneglycol bis(2-ethylhexyl carboni t d tetraethylene glycolfljis(z ethy]hexyl carbonate) Engine cleanliness m modified Chevrolet S-II test and polyglycol (av. molweight 300) bis(2-ethylhexyl carbonate). f Piston Total The data in Table II shows that regular gasoline fuels 8km 521515.; containing 0.1 volume percent polyglycol carbonate of prescribed composition are approximately equivalent to Base mp1 7,5 55,2 premium grade 'gasolines with regard to deposit-forming g lfl gg g g e p c t et ylene g y 8 0 87 o tendencies; The piston skirt ratings of 8.0 to 9.5 and Base {119L010 g-55.1.1 55.iigggeiggg'gieggi' the total engine ratings of 84 to 91+ are better ratlngs b1S(a11Y1carbnat) 857 than are obtained with some premium fuels. The ability I f p yg y carbonates to boost regular grade f s t The specificity of the polyglycol carbonate ester structhe engine cleanliness level of Premium grade fuels is a Q. tures is further shown'by a consideration of the informaignlficant advance and a ub ant a step forward to 801V- tion recorded in Table V. Numerous compounds were 111g The s uffa'ce ignition P ms encountered in g I evaluated that contained portions of the preferred overall compression engines. structure, but in no case was an outstanding deposit con The effect of varying concentrations of diethylene glytrol additive obtained. In some cases, the additive decol 'bis(allyl carbonate) in regular fuel are shown in graded the base fuel. Evaluation of the additives was Table The data in Table III indicate that a conmade in the high quality regular grade gasoline previously centration between 0.1 and 0.2 volume percent is necesdescribed. j

TABLE V Concen- Molec- Weight Piston Total Additive tration, uiar C to O Skirt Engine Volume Weight Ratio Rating Rating Percent N I 4.7 71.7 Diallyl 0. 05 9s 4. 5 5. 0 75. 0 130-- 0. 10 5. a s2. 3 Diallyl ether 0! diethylene glycol. 0. 10 186 2. 5 3. 7 74. 7 Dibutylether oftetraethylene glycoL 0.20 306' 2.4 5.0 76.0 Diethyl ether of diethylene glycol- 0. 20. 162 2. 0 5.0 71. 0 Allyl alcohol o. 05 7o 2. 25 4. 2 72. 2 Diallyl. carbonate 0. 10 142 1. 75 4. 8 75. 8 Di-Z-ethylhexyl carbonate 0. 10 296 4. 25 5. 7 81. 7

sary in order to obtain optimum results with diethylene glycol bis (allyl carbonate) in regular grade gasoline.

In Table IV the action of a polyglycol carbonate ester in reducing the deposit-forming properties of a premium grade fuel are shown. Since the premium grade fuel already has an excellent rating with respect to the tendency'to form'deposits, theaction of a polyglycol carbonate ester is not as striking jasin the regular grade fuel. However, significant improvement in the deposit-forming tendency in the premium grade fuel is eifected by the addition of the polyglycol' carbonate ester and smaller quantities of an additive are needed in order to obtain optimum results of the premium grade fuel.

'The'reference fuel employed'in Table IV was a" high quality premium grade fuel'comprising mainly. fluid catalytically cracked stock and straight run gasoline. The reference fuel had a 95 A. S. T. M. research octane rating, contained 2.74 ml. of TEL fluid per gallon, had an API gravity of 6 0 to 65 and a boiling point range between 100 and 398 F.; the base-fuel was negative in the copper corrosion test and hadan oxidation stability in the ASTM test of 240 minutes minimum. The reference fuel also contained minor amounts of conventional gasoline inhibitors, for example, approximately 6 poundsw Octane requirement increase.0ctane requirement in- A 45 crease of engines in service is'an old problem that becomes more severe with the modern high compression engines. An engine which has an initial octane requirements, of'85 often will develop a-need for a octane fuel during service. Ithas been postulated that octane requirement increase is attributable partially to engine design and partially to the fuel and lubricant.

Reduced octane requirement increase was demonstrated in-the laboratory for the additive-containing motor fuel of this invention in comparison with the reference fuel by the following procedure:

LAUSON H-Z ORI TEST PROCEDURE TABLE VI Variable Condition Test, Hours To equilibrium 0. R.=200 hr. Wattmeter Reading 1,5001,600.

Fuel Flow, lbs. per hr 1.6 :t; .04. Coolant Temp., "F 210 :1; 5. d: 5.

011 Temp., F-

e1 Check once each day.

0 Inches (each hour).

Record each hour.

Orifice Press. Drop "Octane requirement of. the engine was determined approximately every 24 hours. Before taking octane requirementthe oil level waszchecked and necessary addi- 1 r r tions made and the following 'items determined and recorded.

Compression pressure at operating throttle position Air temperature, F.

Barometer reading, in. Hg

Spark advance, B. T. D. C. (should be degrees) Amount of oil added Equilibrium octane requirement was reached when the engine had operated for 50 hours with a change in ORI of 2 numbers or less.

A modified Model H2 Lauson engine, which is a single cylinder, liquid cooled, four stroke spark ignition engine with a bore of 2% inches and a stroke of 2% inches giving a displacement of 14.89 cubic inches, was used. Power output was rated at 4.3 H. P. at 2400 R. P. M. Compression ratio of the engine was 6.5 :1

using a modified head. The original flywheel magneto was replaced with a BendiX-Scintella magneto, Type.

GER-4R and coupledto the forward end of the engine crankshaft to provide ignition. The engine was operated under the following conditions:

Engine speed 1800 R. P. M.

Engine load 1600 Watts.

Spark advance 20 B. T. C.

Fuel flow rate l.6#/hr.

Air-fuel ratio 13.5 :1

Coolant temperature 210 F.

Carburetor air temp 100 F. v Oil temperature- 175 F.

Test duration App. 200 hr. to equilibrium octane requirement.

The octane requirement of the engine was determined with primary reference fuels on the clean engine and?" after each period of operation until equilibrium octane The loss in weight of the two compression rings is taken as a measure of the low temperature wear properties of the fuel and oil combination. By holding the 'oil constant, the relative wear characteristics of fuels can be determined. Using Advanced Custom Made Havoline oil, previously described, the results shown in Table VI], below, were obtained with a premium fuel with and without a polglycol carbonate ester:

TABLE VII Low temperature wear Mg. Weight Fuel Loss of Compression Rings Premium fuel 50 Premium fuel plus 0.2% by volume diethylene glycol bis (allyl carbonate) 42 The test used for high temperature wear and corrosion is an extended version of the CRCL41252 Test. In the extended test, the total test time is 72 hours inljstead of the usual 36. This increase in test time makes the test more severe.

Bearing weight loss is the criterion for possible corrosive or wear action. Asindicated in requirement was attained. The difference betweenthe initial (clean) octane requirement and the equilibrium octane requirement is known as the octane requirement increase or ORI.

The premium grade fuel employed in Table IV gave an octane requirement increase of 20 units in the above test whereas the same fuel plus 0.2 volume percent diethylene glycol bis(allyl carbonate) showed a maximum increase of 17 units in this test. Of more significance is the fact that the octane requirement increase would successively build up to a maximum of about 17 using the additivecontaining fuel and then would quickly drop to an increase of 7 units followed by successive buildups and drops of a similar magnitude. It has been theorized that these periodic drops in octane requirement increase in the engine are a consequence of large areas of deposits being rapidly removed by the action of the polyglycol carbonate esters during engine operation.

Effect of additives on engine wear. Frequently, in the course of developmentof useful additives for improved fuels, deleterious effects will be encountered. The deleterious effects may greatly overshadow possible benefits. Deleterious action is frequently associated with increase in engine wear of such engine parts as piston rings, cyl

inder walls, bearings, and valves. The fuels obtained by the addition of a minor amount of a polyglycol carbonate ester of prescribed composition are unusual in that no deleterious effects have been encountered in the large amount of engine testing conducted. In fact, with respect to wear of vital engine parts, it has been found that wear is actually decreased under both low and high temperature conditions.

The test used for low temperature wear evaluations uses a 1949 Pontiac 8 piston and Sealed Power IB-10 compression piston rings installed in a CFR high-speed crankcase. operating conditions are as follows:

The cylinder liner is nitridedcast'iron. The

Table VIII, below, no deleterious eifect was noted for a polyglycol carbonate ester.

TABLE VIII High temperature wear CRC-L-4 extended test Gram Weight; Fuel Loss of Bearing Regular Grade Fuel 0.079 Regular G rade Fuel plus 0.2% by volume diethylene glycol b1s(a11y1 carbonate) 0. 044

The foregoing data prove that the polyglycol carbonate esters of prescribed composition are outstanding. fuel additives for controlling deposits and at the same time do not possess any deleterious effects with regard to engine wear.

Obviously, many modifications and variations ofthe invention, as hereinbefore set forth, may be made Without departing from the spirit and scope thereof, and, therefore, only such limitations should be imposed as are indicated in the appended claims.

We claim:

l. A normally liquid hy rocarbon fuel for internal combustion engines containing a polyglycol carbonate ester having a carbonto oxygen'weight ratio below 2.5

and a boiling point above 650 F. and the following general formula ROOCO (R0) COOR" wherein Ris a divalent aliphatic hydrocarbon radical containing at least 2 carbon. atoms, R and R-' are aliphatic hydrocarbon radicals containing between 3 and 18' carbon atoms and n is an' integer having a value of 2 to 10, said glycol carbonate ester. being present in an amount suflicient to reduce the deposit-forming property of said fuel.

2. A hydrocarbon fuel according to claim 1 containing 0.01 to 1.0 volume percent of polyglycol carbonate ester.

3. A hydrocarbon fuel according to claim 1 containing 0.04 to 0.3 volume percent of a polyglycol carbonate ester.

4. A hydrocarbon fuel according to claim 1 in which said R and R contain 3 to 10 carbon atoms.

5. A gasoline containing a polyglycol carbonate ester having a carbon to oxygen weight ratio below 2.5 and a boiling point above 650 F. and the following general formula ROOCO(RO),,COOR" wherein R is a divalent aliphatic hydrocarbon radical containing at least 2 carbon atoms, R and R" are aliphatichydrocarbon radicals containing between 3 and 18 carbon atoms and n is an integer having a value of 2 to 10, said glycol carbonate ester being present in an amount suflicient to reduce the deposit-forming property of said fuel.

6. A gasoline according to claim 5 containing 0.01 to 1.0 volume percent of polyglycol carbonate ester.

7. A gasoline according to claim 5 containing 0.04 to 0.3 volume percent of a polyglycol carbonate ester.

8. A gasoline according to claim 5 in which said R and R" contain 3 to 10 carbon atoms.

9. A gasoline containing 0.1 to 1.0 volume percent diethylene glycol bis (allyl carbonate).

10. A gasoline containing 0.1 to 1.0 volume percent diethylene glycol bis(amyl carbonate).

11. A gasoline containing 0.1 to 1.0 volume percent tetraethylene glycol bis(allyl carbonate).

12. A gasoline containing 0.1 to 1.0 volume percent polyglycol (av. molecular weight 300) bis(2-ethylhexy1 carbonate).

13. A gasoline containing 0.1 to 1.0 volume percent triethylene glycol bis (allyl carbonate).

References Cited in the file of this patent UNITED STATES PATENTS 2,331,386 Gaylor Oct. 12, 1943 2,379,252 Muskat et al. June 26, 1945 2,651,657 Mikeska et al Sept. 8, 1953 2,789,891 Brandes et a1 Apr. 23, 1957 UNITED STATES PATENT OFFICE CERTIFICATE OF CORBECTIQN Patent No. 2,844,448 1958 Robert. L Heisler at El It is herebyl certif-ied that error appears in the printed epeoification of the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.

Column 2, line 62, Table I, first column thereof, thirtl item, for "bis(n amyl carbonase)" read ==bisxfin amyl carbonate); oollmm 4,, line 34, for "936 F," read 396 Fo columns 5 and. 6, Table V first column thereof, second. item, for "Diallyl" read Dflallyl ethcr -o Signed and sealed this 14th day of October 1958;"

SEAL fittest:

KARL VAQUJINE ROBERT E. WATSON Attesting Officer Commissioner of Patents

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Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3047374 *Mar 2, 1960Jul 31, 1962Atlantic Refining CoMotor fuel compositions
US3881452 *Jan 22, 1973May 6, 1975Mcculloch CorpMethod and apparatus for operating an engine-driven chain saw in an environment where ice may form in the carburetor of the engine
US4380455 *Mar 1, 1982Apr 19, 1983The Dow Chemical CompanyDialkyl carbonates as phase separation inhibitors in liquid hydrocarbon fuel and ethanol mixtures
US4490154 *May 20, 1983Dec 25, 1984Texaco Inc.Fuels containing an alkenylsuccinyl polyglycolcarbonate ester as a deposit-control additive
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US5326486 *Sep 25, 1992Jul 5, 1994Mitsui Petrochemical Industries, Ltd.Lubricating oil composition
US5505869 *Jul 18, 1994Apr 9, 1996Euron S.P.A.Two-cycle internal combustion engine with lubricant comprising carbonate ester of aliphatic triol or tetraol
DE1221845B *May 29, 1962Jul 28, 1966Inst Francais Du PetroleDieselkraftstoffe
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EP0306108A2 *Sep 2, 1988Mar 8, 1989Theofil Wenzel RejdaMethod for combating corrosion of hydrocarbon containers and liquid hydrocarbons having corrosion inhibiting properties
U.S. Classification44/387, 558/266, 558/265
International ClassificationC10L1/18
Cooperative ClassificationC10L1/1915, C10L1/191, C10L1/18, C10L1/1986, C10L1/1985
European ClassificationC10L1/18