US3795495A - Gasoline anti-icing additives - Google Patents

Gasoline anti-icing additives Download PDF

Info

Publication number
US3795495A
US3795495A US3795495DA US3795495A US 3795495 A US3795495 A US 3795495A US 3795495D A US3795495D A US 3795495DA US 3795495 A US3795495 A US 3795495A
Authority
US
Grant status
Grant
Patent type
Prior art keywords
gasoline
phosphate
succinimide
additive
icing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
Inventor
W Howland
W Mallett
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Union Oil Co of California
Original Assignee
Union Oil Co of California
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Grant date

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/143Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/222Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224Amides; Imides carboxylic acid amides, imides
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/234Macromolecular compounds
    • C10L1/238Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/26Organic compounds containing phosphorus
    • C10L1/2633Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
    • C10L1/2641Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond) oxygen bonds only

Abstract

A combination of two specific types of known gasoline additives is found to provide, in addition to good overall carburetor detergency, a synergistic degree of anti-icing activity. One additive is an alkyl aminoalkyl phosphate, while the other is a succinimide condensation product of an alkylene polyamine wit an alkenyl succinic anhydride.

Description

United States Patent 91 Howland et al.

[ 1 Mar. 5, 1974 1 1 GASOLINE ANTI-ICING ADDITIVES [75] Inventors: Ward W. Howland, Anaheim;

William R. Mallett, Placentia, both of Calif.

[73] Assignee: Union Oil Company, Los Angeles,

Calif.

[22] Filed: Jan. 20, 1,971

[21] Appl No.: 108,015

[52] US. Cl 44/58, 44/63, 44/D1G. 1,

44/D1G. 4, 44/72 [51] Int. Cl C101 1/26 [58] Field of Search 44/58, 63, 56 D, 69 P [56] References Cited UNITED STATES PATENTS 3,384,466 5/1968 Popkin 44/D1G. 4 2,863,742 12/1958 Cantrell et a1. 44/D1G. 4

3,007,782 11/1961 Brown ct a1. 44/D1G. 4 3,460,923 8/1969 Dorcr, .lr. 44/D1G. 4 3,443,918 5/1969 Kautsky et a1. 44/63 3,219,666 11/1965 Norman ct a1 252/51.5 A

Primary Exuminer-Daniel E. Wyman Assistant Examiner-Mrs. Y. H. Smith Attorney, Agent, or Firm-Richard C. Hartman; Dean Sandford; Lannas S. Henderson 57 ABSTRACT 9 Claims, 1 Drawing Figure 1 GASOLINE ANTI-ICING ADDllTlVES BACKGROUND AND SUMMARY OF THE INVENTION A great variety of chemical additives have previously been proposed for use as detergents and/or dispersants in gasolines, for the primary purpose of removing and- /or preventing the formation of deposits of dirt, gum, lacquer and the like in the induction system of internal combustion engines, primarily on the internal surfaces of the carburetor throat and associated parts. Some of these detergent additives are known to be effective in varying degrees as anti-icing agents, while others are of littleor no value for that purpose. This is not particularly surprising, since the formation and removal of ice from carburetor surfaces bears little apparentanalogy to the formation and removal of dirt, gum-and lacquer deposits from such surfaces.

As is well known, the operation of carburetor-fed internal combustion engines under cool, humid weather conditions is apt to result in frequent stalling of the engine, especially during the warm-up period. Such stalling is a definite safety hazard as well as a decided inconvenience. It is now recognized that stalling of this nature is attributable to the formation of ice on the throttle plate and the nearby surfaces of the carburetor barrel. The water which forms the ice does not come from the gasoline, butfrom the air entering the carburetor. As noted above, stalling generally occurs in cool, humid weather when the temperature is between about 35 and 65F, andthe relative humidity is above about 65 percent. The most critical conditions are temperatures of about 40-60F., and 90-100 percent relative humidity.

As the gasoline evaporates in the carburetor, it reduces the temperature of the surrounding metal surfaces by as much as 4050F. Moisture in the incoming air comes in contact with these parts and begins to build up ice on the throttle plate and in the carburetor barrel. The higher the humidity, the faster is the buildup of ice. Then, when the engine is idling, the throttle plate closes and the ice chokes off the normal flow of air through the small clearance between the throttle plate and the carburetor wall. This causes the engine to stall. The engine-can usually be restarted when the heat from the exhaust manifold melts the ice sufficiently. However, stalling will continue until the engine is completely warmed up.

Carburetor icing occurs in some vehicles when cruising at speeds of 30-60 mph. Such icing is a considerable problem in the case of certain trucks and cars equipped with carburetors having venturi type fuel-air mixing tubes (emulsion tubes). The ice builds up on the tube and restricts the flow of air, thereby enriching the fuel mixture and reducing efficiency.

We have now discovered that these icing problems can be materially reduced by adding to the gasoline fuel certain, minor proportions of two different additives which have previously been suggested for use individually as detergent additives. Neither of the additives alone is exceptionally effective for anti-icing, but surprisingly, the combination is synergistic in that it is much more effective than the same proportion of either additive alone. The first additive, referred to herein as the Succinimide additive, is a complex condensation product of approximately equal mole-ratios of a relatively low molecular weight alkenyl succinic anhydride with an alkylene polyamine such as diethylene triamine. lt is almost completely ineffective for anti-icing when used alone. The second additive is a mono alkyl, mono(amino alkyl)phosphate, referred to herein as the phosphate ester additive. Used alone it is fairly effective for anti-icing, but considerably less effective than the combination. I

DETAILED DESCRlPTlON TABLE 1 Pounds per Thousand Barrels of Gasoline" Broad Range Preferred Range Phosphate Ester Succinimide (1) One pound per thousand barrels 4 part; per million.

In addition, the overall proportion of the combined additives should fall within the range of about l340, preferably l3.520 pounds per thousand barrels. It should be observed that these-additives are often supplied commercially as concentrates in an inert solvent; the proportions cited above are on a solvent-free basis.

Preferred synergistic weight ratios of the two additives to each other range between about 20/80 to 60/40 of phosphate ester to succinimide. A premixed package comprising the two additives in these relative proportions may be conveniently utilized, with or without an added solvent such as toluene or other petroleum distillate. Other additives may also be included in the package, such as a mineral lubricating oil to reduce intake valve deposits. In some cases, the presence of a lubricating oil may actually enhance the anti-icing effect of the two-component additive. Suitable lubricating oils may have a viscosity at 100F. of 200 to 700 SSU, a viscosity index above and an A.P.l. gravity of 25 to 32. A particularly suitable oil, referred'to herein as 300 neutral oil, has a viscosity of about 320 SSU at 100F. and at 210F. of about 52.2, a V.l. of about a flash point of 445F. and an A.P.l. gravity of about 28.6.

A preferred additive package for use herein is composed as follows:

Volume Succinimid 39 Phosphate Ester DMA-4 28 XyleneKerosene Solvent 33 (l) Described hereinafter wherein R is an alkylene group containing from 4 to about 25, preferably six to 20 carbon atoms, and R, is an alkyl group having from five to about 25, preferably -20 carbon atoms. The sum of the carbon atoms R and R, should be in the range of l8-36, preferably 2()3(). Suitable exemplary compounds include dodecyl 8-aminooctyl phosphate, octadecyl o-aminohexyl phosphate, dodecyl l2-aminododecyl phosphate, decyl 6- aminododecyl phosphate, and the like. A particularly suitable phosphate additive is marketed by the El. du- Pont de Nemours Co. under the trade name DMA-4, and contains 27 total carbon atoms, analyzing 64.7% C, 12.9% 0, 6.4% P, and 3.0% N. The Succinimide Additive This additive can best be described as a condensation product of approximately one mole of an alkenyl succinic anhydride of the formula:

with about 0.60 to 1.5 moles of an alkylene polyamine of the formula:

wherein R is an alkenyl group having from 8 to about 50, preferably l54(), carbon atoms, R, is a lower alkylene radical of about two to eight carbon atoms, and x is a number from 1 to about 10, preferably 2 to 6. The resulting product is a complex mixture of monomeric and polymeric amides and imides with an average molecular weight normally in the range of about 400 to 800. Where ethylene diamine is employed as the amine, representative reaction products are believed to include compounds such as:

but the presence of other specific amides, imides and amide-imides is not to be excluded.

The condensation reaction is carried out at temperatures of about l250 F., preferably ISO-200C, until about 1 mole of water per mole of alkenyl succinic anhydride employed has been split off. Preferably an in US. Pat. No. 2,182,178.

Suitable alkenyl succinic anhydride starting materials include compounds wherein R in the above formula is n-octenyl, iso-doceccnyl, di-isobutcnyl, tri-isobutenyl, tetra-isobutenyl, hexa-isobutenyl, deca-isobutenyl, and the like. Such compounds are well known in the art, and are normally prepared by reacting the appropriate olefin with maleic anhydride, as described in more detail in eg, US. Pat. Nos. 3,172,892 and 3,443,918.

Suitable exemplary alkylene polyamine reactants include ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, propylene diamine, dipropylene triamine, di(tetramethylene)triamine, and the like.

The succinimide reaction products prepared as described above are fairly effective as carburetor detergent gasoline additives. However, we have found that at concentration levels effective for carburetor detergency, they are almost completely ineffective for deicing. Strangely enough, at lower concentration levels which are relatively ineffective for carburetor deter gency, they appear to function somewhat more effectively for de-icing. But even at these low concentrations they are not as effective as the combination of additives when used at the herein prescribed concentrations.

-A preferred succinimide additive for use herein is marketed by the American Oil Co. under the trade name, Amoco 575.

Base Fuels The gasoline stocks to which the succinimide and allphatic amine may beadded with synergistic anti-icing effect include any petroleum fraction boiling in the conventional gasoline range of about to 400F., and preferably having an ASTM 50 percent boiling point between about 180'and 220F. The 50 percent boiling point of a gasoline is a critical indicia of its icing propensity. As a rule of thumb, gasolines with 50 percent. boiling points below 180F. are considered severe, such that the surfactant-type additives utilized herein are relatively ineffective; for these highly volatile gasolines freeze point depressants such as alcohols or glycols may berequired. Gasolines having a 50 percent point above about 220F. are unlikely to cause icing. Hence, for practical purposes the principal utility of the combined additives of this invention resides in their use in gasolines having a 50 percent boiling point between I about 180 and 220F.

Typical commercial gasolines which may be utilized herein may comprise straight run gasolines, catalytically cracked gasolines, catalytic reformates and alkylates, and blends thereof. The fuel may also contain other conventional additives such as lead alkyls, or ganic halide lead scavengers, phenolic anti-oxidants, metal deactivators such as disalicylal-ethylene diamine,

etc.

EXAMPLES To demonstrate the above described synergistic results, a series of anti-icing test runs was carried out using various combinations and proportions of the respective additives. The base gasoline employed in all runs was a leaded blend of a light hydrocracked gasoline, a reformate, and a heavy catalytically cracked gasoline, the blend having an ASTM boiling range substantially as follows:

Percent cylinder during stabilization periods when the carburetor was without fuel.

Test Procedure The actual test procedure consisted in running the Overhead OF 5 engine at constant speed while the throttle was cycled on a fixed time schedule between a cruise and an idle LB.P. 3? setting. The number of cycles required to develop 8 40 enough ice to cause a l inch Hg increase in manifold 50 1% vacuum at the idle setting was taken as an arbitrary 3 l0 stalling condition. El. 432 Each test was preceded by a careful purge and restabilization procedure. During the purge period an auxiliary air heater mounted in the carburetor inlet Test h h tube was energized. This added heat dried out moisture A single cylinder CFR engine coupled to a constant condensed during the preceding test and brought the h dyhamometer was j for the teStS The mst carburetor throttle body back to test conditions more gasoline was fed to the engine through a special carbuquickly The temperature of the throttle body dropped remr operatmgfi} ah atmcsphere of cohtrohed temper to about F. during each test. After the throttle body and y' when carburetor fomled S 0 was heated to 50F, the auxiliary heater was turned off mg f test the Constant sheed dyhamometer malhtamed 2 and the engine was stabilized for an additional 3 minehghe Speed so the ehghe wohld hm Stah- T pres utes with fuel supplied directly to the cylinder by the ence and amount of carburetor ice formed as indicated injection System Fuel flowfid through the carburetor by an Increase in manifold vacuum. A vacuum transonly during the actual test period ducerdand strip chart recorder ell'g used to provide a 25 Additives recor of t e variation in mani 0 vacuum as a test The succlmmide additive (Succmtmrde B was progrehsed' A identified as a condensation roduct of one mole of a A spill-type carburetor was used to assure a constant polyisobutenyl succmic anhydride having an average of air-fuel ratio. The conventional float and needle valve approximately 29 carbon atoms 1n the polyisobutenyl assembly was removed and a Circular (Overflow radical with about 0 75 mole of dieth lene triamine drain) installed inside the float chamber. The gasoline y how to the carhhretor was adlusted so that a Small The resulting product was a mixture of amides and imhh of gasohne would Y h thereby always ides having a number average molecular weight of providing a fixed level of gasoline in the float chamber. about 700, and analyzing 4'9 weight percem nitrogen.

An atmosphere of controlled temperature and huh y hpp q to the 'h h y means of an The phosphate ester was the above described duPont air conditioning unit. A gasoline in ection system, in- DMA 4 lecting gasoline into the Cylinder was used to fire the The results of the various runs were as follows:

TABLE 2 Concentration, Anti-lcing Rating, Run No. Additive Lbs/M Bbl Cycles to Stall l None i 6 2 None 6 3 Succinimide B 7 8 4 Succinimide B 7 8 5 Succinimidc B 7 8 6 Succinimide B 7 9 7 Succinimide B 14 7 8 Succinimide B 14 7 9 Succinimide B 14 7 ll) Succinimide B 14 7 ll Succinimide B l4 7 l2 Succinimide B l4 7 l3 Phosphate Ester 4.8 8 l4 Phosphate Ester 4.8 9 l5 Phosphate Ester 4.8 l0 l6 Phosphate Ester 4.8 l0 l7 Phosphate Ester 8.0 8 l8 Phosphate Ester 8.0 9 l9 Phosphate Ester 8.0 9 20 Phosphate Ester 8.0 9 21 Phosphate Ester l6 I2 22 Phosphate Ester 24 12 23 (Succinimide B 3.5) 7

(Phosphate Ester 2.4)

24 Repeat of run 23 I 7 25 (Succinimide B 7 8 (Phosphate Ester 4.0)

26 Repeat of run 25 8 27 (Succinimidc B 9.1) IS (Phosphate Ester 5.6)

TABLE 2 Continued 29 Repeat of run 27 (I) Solvent-frec basis.

Concentration in Gasoline Additive Lbs/M Barrels Succinimidc c so Octyl, lZ-amino dodccyl phosphate 60 Succinimidc D 10.0 Lauryl, lZ-amino lauryl phosphate 5.0 Succinimidc E 12.0 Hexyl, l2-amino octadeeyl phosphate 8.0

(l) A condensation product of 0.8 moles of propylene diamine with one mole of a 625 Av. molecular weight polyisobutcnyl succinic anhydride.

(2) A condensation product of 0.9 mole of tctracthylene pcntamine with one mole of a 350 Av. molecular weight polyisobutcnyl succinic anhydride.

(3) A condensation product of 11 moles of dipropylenc triamine with one mole of a 550 Av. molecular weight polyethylene succinic anhydride.

The following claims are believed to define the true scope'of the invention.

We claim:

1. An anti-icing gasoline composition comprising a base gasoline boiling substantially in the range of about 100-400F., and dissolved therein:

1. between about 3 and 20 pounds per thousand barrels of an alkyl aminoalkyl phosphate having the formula:

1 1 HO-P-ORNH:

wherein R is an alkylene group having from four to about 25 carbon atoms, and R is an alkyl group having from five to about 25 carbon atoms, the sum of the carbon atoms in R and R being in the range of 18-36; and

, 2. between about and 30 pounds per thousand barrels of a succinimide condensation product of one mole of an alkenyl succinic anhydride of the formula:

with about 0.6 to 1.5 moles of an alkylene polyamine of the formula:

wherein R is an alkenyl group having from eight to about 50 carbon atoms, R is a lower alkylene radical of about two to eight carbon atoms, and x is a number from 1 to about 10; and wherein the combined proportion of components 1 and 2 in the gasoline is between about 13 and 40 pounds per thousand barrels.

2. A composition as defined in claim 1 wherein the weight-ratio of component 1 to component 2 is between about 20/80 and 60/40.

3. A composition as defined in claim 1 wherein said alkylene polyamine is diethylene triamine.

4. A composition as defined in claim 1 wherein the combined proportion of said components 1 and 2 in the gasoline is between about 13.5 and 20 pounds per thousand barrels.

5. A composition as defined in claim 1 wherein said base gasoline has a 50 percent boiling point between about 180 and 220F.

6. A composition as defined in claim 1 wherein the weight-ratio of component 1 to component 2 is between about 20/ and 60/40; said alkylene polyamine is ethylene diamine or diethylene triamine; the combined proportion of said components 1 and 2 in the gasoline is between about 13.5 and 20 pounds per thousand barrels; and wherein said base gasoline has a 50 percent boiling point between about and 220F.

7. A synergistic anti-icing additive for gasoline comprising:

1. an alkyl aminoalkyl phosphate having the formula:

HO-P-O RNHz wherein R is an alkylene group having from four to about 25 carbon atoms, and R is an alkyl group having from 50, to about 25 carbon atoms, the sum of the carbon atoms in Rand R being in the range of 18 to 36; and

2. a succinimide condensation product of one mole of an alkenyl succinic anhydride of the formula:

with about 0.6 to 1.5 moles of an alkylene polyamine of the formula:

between about /80 and 60/40. H2N(RNH 8. An additive as defined in claim 7 including in addiwherein R is an alkenyl group having from eight to tion a paraffinic lubricating oil.

about 50 carbon atoms, R is alower alkylene radi- 9. An additive as defined in claim 7 wherein said cal of about two to eight carbon atoms, and x is a 5 component 2 has an average molecular weight between number from 1 to about H); about 400 and 800.

the weight ratio of component 1 to component 2 being

Claims (10)

  1. 2. A composition as defined in claim 1 wherein the weight-ratio of component 1 to component 2 is between about 20/80 and 60/40.
  2. 2. between about 5 and 30 pounds per thousand barrels of a succinimide condensation product of one mole of an alkenyl succinic anhydride of the formula:
  3. 2. a succinimide condensation product of one mole of an alkenyl succinic anhydride of the formula:
  4. 3. A composition as defined in claim 1 wherein said alkylene polyamine is diethylene triamine.
  5. 4. A composition as defined in claim 1 wherein the combined proportion of said components 1 and 2 in the gasoline is between about 13.5 and 20 pounds per thousand barrels.
  6. 5. A composition as defined in claim 1 wherein said base gasoline has a 50 percent boiling point between about 180* and 220*F.
  7. 6. A composition as defined in claim 1 wherein the weight-ratio of component 1 to component 2 is between about 20/80 and 60/40; said alkylene polyamine is ethylene diamine or diethylene triamine; the combined proportion of said components 1 and 2 in the gasoline is between about 13.5 and 20 pounds per thousand barrels; and wherein said base gasoline has a 50 percent boiling point between about 180* and 220*F.
  8. 7. A synergistic anti-icing additive for gasoline comprising:
  9. 8. An additive as defined in claim 7 including in addition a paraffinic lubricating oil.
  10. 9. An additive as defined in claim 7 wherein said component 2 has an average molecular weight between about 400 and 800.
US3795495A 1971-01-20 1971-01-20 Gasoline anti-icing additives Expired - Lifetime US3795495A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US10801571 true 1971-01-20 1971-01-20

Publications (1)

Publication Number Publication Date
US3795495A true US3795495A (en) 1974-03-05

Family

ID=22319778

Family Applications (1)

Application Number Title Priority Date Filing Date
US3795495A Expired - Lifetime US3795495A (en) 1971-01-20 1971-01-20 Gasoline anti-icing additives

Country Status (1)

Country Link
US (1) US3795495A (en)

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3873276A (en) * 1970-01-19 1975-03-25 Inst Francais Du Petrole Organic compounds for use as additives for motor-fuels
US4471091A (en) * 1982-08-09 1984-09-11 The Lubrizol Corporation Combinations of carboxylic acylating agents substituted with olefin polymers of high and low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4486573A (en) * 1982-08-09 1984-12-04 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4489194A (en) * 1982-08-09 1984-12-18 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high/low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4509955A (en) * 1982-08-09 1985-04-09 The Lubrizol Corporation Combinations of carboxylic acylating agents substituted with olefin polymers of high and low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
EP0155171A2 (en) * 1984-03-12 1985-09-18 Exxon Research And Engineering Company Additive concentrates for distillate fuels
US4564460A (en) 1982-08-09 1986-01-14 The Lubrizol Corporation Hydrocarbyl-substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4575526A (en) 1982-08-09 1986-03-11 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same
US4596663A (en) * 1982-08-09 1986-06-24 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4613342A (en) 1982-08-09 1986-09-23 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4623684A (en) 1982-08-09 1986-11-18 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US5041622A (en) * 1988-04-22 1991-08-20 The Lubrizol Corporation Three-step process for making substituted carboxylic acids and derivatives thereof
FR2696747A1 (en) * 1992-10-09 1994-04-15 Inst Francais Du Petrole New amine phosphate(s) contg. terminal imide gp.
EP0593331A1 (en) * 1992-10-09 1994-04-20 Institut Francais Du Petrole Amines phosphates having a terminal imide cycle, their preparation and their use as additives for motor-fuels
FR2699551A1 (en) * 1992-12-18 1994-06-24 Inst Francais Du Petrole New amine phosphate(s) contg. terminal imide gp.
US5393309A (en) * 1991-09-13 1995-02-28 Chevron Research And Technology Company Fuel additive compositions containing polyisobutenyl succinimides
US5837126A (en) * 1990-12-13 1998-11-17 Union Oil Company Of California Gasoline fuel
US20030173250A1 (en) * 2002-03-13 2003-09-18 Blackwood David Macdonald Unleaded gasoline compositions
FR2839315A1 (en) * 2002-05-03 2003-11-07 Totalfinaelf France Additive for improving the thermal stability of oil compositions
US20050028434A1 (en) * 2003-06-23 2005-02-10 Envirofuels, L.P. Additive for hydrocarbon fuel and related process
US20060101710A1 (en) * 2004-11-15 2006-05-18 Envirofuels L.P. Additive for solid hydrocarbon fueled direct fired burners, furnaces, open flames and related processes
US20060179709A1 (en) * 2004-09-28 2006-08-17 Envirofuels L.P. Additive for liquid or liquified hydrocarbon fueled direct fired burners, open flames and related processes
US20060236596A1 (en) * 2005-04-22 2006-10-26 Envirofuels L.P. Additive for hydrocarbon fuel consisting of non-acidic inorganic compounds of boron and related processes
US20070049693A1 (en) * 2005-08-22 2007-03-01 Envirofuels, Llc Flow enhancement compositions for liquid and gases in tubes and pipes
US20080263939A1 (en) * 2006-12-08 2008-10-30 Baxter C Edward Lubricity improver compositions and methods for improving lubricity of hydrocarbon fuels

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2863742A (en) * 1954-10-04 1958-12-09 Gulf Oil Corp Gasoline fuel compositions
US3007782A (en) * 1958-07-31 1961-11-07 Standard Oil Co Motor fuel composition
US3219666A (en) * 1959-03-30 1965-11-23 Derivatives of succinic acids and nitrogen compounds
US3384466A (en) * 1967-02-21 1968-05-21 Esso Res And Engienering Compa Amine-phosphates as multi-functional fuel additives
US3443918A (en) * 1965-09-21 1969-05-13 Chevron Res Gasoline composition
US3460923A (en) * 1964-08-03 1969-08-12 Lubrizol Corp Fuels containing amine phosphate anti-icing compositions

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2863742A (en) * 1954-10-04 1958-12-09 Gulf Oil Corp Gasoline fuel compositions
US3007782A (en) * 1958-07-31 1961-11-07 Standard Oil Co Motor fuel composition
US3219666A (en) * 1959-03-30 1965-11-23 Derivatives of succinic acids and nitrogen compounds
US3460923A (en) * 1964-08-03 1969-08-12 Lubrizol Corp Fuels containing amine phosphate anti-icing compositions
US3443918A (en) * 1965-09-21 1969-05-13 Chevron Res Gasoline composition
US3384466A (en) * 1967-02-21 1968-05-21 Esso Res And Engienering Compa Amine-phosphates as multi-functional fuel additives

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3873276A (en) * 1970-01-19 1975-03-25 Inst Francais Du Petrole Organic compounds for use as additives for motor-fuels
US4564460A (en) 1982-08-09 1986-01-14 The Lubrizol Corporation Hydrocarbyl-substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4486573A (en) * 1982-08-09 1984-12-04 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4489194A (en) * 1982-08-09 1984-12-18 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high/low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4509955A (en) * 1982-08-09 1985-04-09 The Lubrizol Corporation Combinations of carboxylic acylating agents substituted with olefin polymers of high and low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4623684A (en) 1982-08-09 1986-11-18 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4471091A (en) * 1982-08-09 1984-09-11 The Lubrizol Corporation Combinations of carboxylic acylating agents substituted with olefin polymers of high and low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4575526A (en) 1982-08-09 1986-03-11 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same
US4613342A (en) 1982-08-09 1986-09-23 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4596663A (en) * 1982-08-09 1986-06-24 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
EP0155171A3 (en) * 1984-03-12 1986-06-04 Exxon Research And Engineering Company Additive concentraties for distillate fuels
EP0155171A2 (en) * 1984-03-12 1985-09-18 Exxon Research And Engineering Company Additive concentrates for distillate fuels
US5041622A (en) * 1988-04-22 1991-08-20 The Lubrizol Corporation Three-step process for making substituted carboxylic acids and derivatives thereof
US6030521A (en) * 1990-12-13 2000-02-29 Union Oil Company Of California Gasoline fuel
US5837126A (en) * 1990-12-13 1998-11-17 Union Oil Company Of California Gasoline fuel
US5393309A (en) * 1991-09-13 1995-02-28 Chevron Research And Technology Company Fuel additive compositions containing polyisobutenyl succinimides
EP0593331A1 (en) * 1992-10-09 1994-04-20 Institut Francais Du Petrole Amines phosphates having a terminal imide cycle, their preparation and their use as additives for motor-fuels
FR2696747A1 (en) * 1992-10-09 1994-04-15 Inst Francais Du Petrole New amine phosphate(s) contg. terminal imide gp.
US5449386A (en) * 1992-10-09 1995-09-12 Institut Francais Du Petrole Amine phosphates having a terminal cyclic imide
FR2699551A1 (en) * 1992-12-18 1994-06-24 Inst Francais Du Petrole New amine phosphate(s) contg. terminal imide gp.
US20030173250A1 (en) * 2002-03-13 2003-09-18 Blackwood David Macdonald Unleaded gasoline compositions
FR2839315A1 (en) * 2002-05-03 2003-11-07 Totalfinaelf France Additive for improving the thermal stability of oil compositions
WO2003095593A1 (en) * 2002-05-03 2003-11-20 Total France Additive for improving the thermal stability of hydrocarbon compositions
US20050223627A1 (en) * 2002-05-03 2005-10-13 Frank Eydoux Additive for improving the thermal stability of hydrocarbon compositions
US20050028434A1 (en) * 2003-06-23 2005-02-10 Envirofuels, L.P. Additive for hydrocarbon fuel and related process
US7604672B2 (en) 2003-06-23 2009-10-20 Envirofuels, Llc Additive for hydrocarbon fuel and related process
US20060179709A1 (en) * 2004-09-28 2006-08-17 Envirofuels L.P. Additive for liquid or liquified hydrocarbon fueled direct fired burners, open flames and related processes
US20060101710A1 (en) * 2004-11-15 2006-05-18 Envirofuels L.P. Additive for solid hydrocarbon fueled direct fired burners, furnaces, open flames and related processes
US20060236596A1 (en) * 2005-04-22 2006-10-26 Envirofuels L.P. Additive for hydrocarbon fuel consisting of non-acidic inorganic compounds of boron and related processes
US20070049693A1 (en) * 2005-08-22 2007-03-01 Envirofuels, Llc Flow enhancement compositions for liquid and gases in tubes and pipes
US20080263939A1 (en) * 2006-12-08 2008-10-30 Baxter C Edward Lubricity improver compositions and methods for improving lubricity of hydrocarbon fuels

Similar Documents

Publication Publication Date Title
US3434814A (en) Emission control additive
US3676089A (en) Motor fuel composition
US3310492A (en) Oils for two-cycle engines containing basic amino-containing detergents and aryl halides
US5279626A (en) Enhanced fuel additive concentrate
US5575823A (en) Diesel fuel compositions
US3822119A (en) Anti-pollution anti-knock gasoline
US3849085A (en) Motor fuel composition
US3687644A (en) Gasoline compositions
US5819529A (en) Method for reducing emissions from two-stroke engines
US3994698A (en) Gasoline additive concentrate composition
US4881945A (en) Fuel compositions containing very long chain alkylphenyl poly(oxyalkylene) aminocarbonates
US2741548A (en) Leaded motor fuel containing boron compounds
Bolt A survey of alcohol as a motor fuel
US3948619A (en) Gasoline composition
US4171959A (en) Fuel composition containing quaternary ammonium salts of succinimides
US3901665A (en) Multi-functional fuel additive compositions
US4022589A (en) Fuel additive package containing polybutene amine and lubricating oil
US4390345A (en) Fuel compositions and additive mixtures for reducing hydrocarbon emissions
US3920698A (en) New organic compounds for use as fuel additives
US5006130A (en) Gasoline composition for reducing intake valve deposits in port fuel injected engines
US5004478A (en) Motor fuel for internal combustion engines
US5458793A (en) Compositions useful as additives for lubricants and liquid fuels
US5752989A (en) Diesel fuel and dispersant compositions and methods for making and using same
US3756793A (en) Fuel composition
US4604103A (en) Deposit control additives--polyether polyamine ethanes