US2982633A - N-substituted alkenyl succinamic acid deicer - Google Patents
N-substituted alkenyl succinamic acid deicer Download PDFInfo
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- US2982633A US2982633A US787133A US78713359A US2982633A US 2982633 A US2982633 A US 2982633A US 787133 A US787133 A US 787133A US 78713359 A US78713359 A US 78713359A US 2982633 A US2982633 A US 2982633A
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- Prior art keywords
- carburetor
- gasoline
- engine
- ice
- succinic acid
- Prior art date
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- 239000002253 acid Substances 0.000 claims description 9
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 8
- 239000001384 succinic acid Substances 0.000 claims description 7
- -1 alkenyl succinic acid Chemical compound 0.000 description 14
- 239000000446 fuel Substances 0.000 description 14
- 239000003570 air Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 150000008064 anhydrides Chemical group 0.000 description 5
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CJYDNDLQIIGSTH-UHFFFAOYSA-N 1-(3,5,7-trinitro-1,3,5,7-tetrazocan-1-yl)ethanone Chemical compound CC(=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 CJYDNDLQIIGSTH-UHFFFAOYSA-N 0.000 description 2
- GGQRKYMKYMRZTF-UHFFFAOYSA-N 2,2,3,3-tetrakis(prop-1-enyl)butanedioic acid Chemical compound CC=CC(C=CC)(C(O)=O)C(C=CC)(C=CC)C(O)=O GGQRKYMKYMRZTF-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 2
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 1
- PFBBCIYIKJWDIN-BUHFOSPRSA-N 2-[(e)-tetradec-1-enyl]butanedioic acid Chemical compound CCCCCCCCCCCC\C=C\C(C(O)=O)CC(O)=O PFBBCIYIKJWDIN-BUHFOSPRSA-N 0.000 description 1
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 1
- UWERUIGPWOVNGG-UHFFFAOYSA-N 3-dec-1-enyloxolane-2,5-dione Chemical compound CCCCCCCCC=CC1CC(=O)OC1=O UWERUIGPWOVNGG-UHFFFAOYSA-N 0.000 description 1
- DEILKUZHRZGBOK-UHFFFAOYSA-N 3-hept-1-enyloxolane-2,5-dione Chemical compound CCCCCC=CC1CC(=O)OC1=O DEILKUZHRZGBOK-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 238000010640 amide synthesis reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000006079 antiknock agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- KCYQMQGPYWZZNJ-BQYQJAHWSA-N hydron;2-[(e)-oct-1-enyl]butanedioate Chemical compound CCCCCC\C=C\C(C(O)=O)CC(O)=O KCYQMQGPYWZZNJ-BQYQJAHWSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS 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
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/224—Amides; Imides carboxylic acid amides, imides
Definitions
- This invention relates to gasoline compositions adapted to improve the operation of internal combustion engines. It is more particularly concerned with motor fuels that provide improved engine operation under cool, humid weather conditions.
- stalling during the warmup period is attributable to the formation of ice on the throttle plate and the carburetor barrel near it.
- the water which forms the ice does not come from the gasoline, i.e., as entrained water, but from the air that enters the carburetor.
- stalling generally occurs in cool, humid weather, when the temperatures are above about 30 F. and below about 60 F. and the relative humidity is about 65 percent and higher, up to 100 percent.
- the most critical conditions are temperatures of 3540 F. and 100 percent relative humidity.
- Icing may also occur in the carburetors of some vehicles when cruising at speeds of 30-60 m.p.h. Such icing is a particular problem in the case of certain trucks and cars equipped with carburetors having Venturi-type fuel-air mixing tubes (emulsion tubes). Such carburetors are found in trucks and in many European cars. The ice builds up in the tube and restricts the flow of air, thereby enriching the fuel mixture and reducing efiiciency. Eventually the engine may stall.
- emulsion tubes Venturi-type fuel-air mixing tubes
- Gasoline is a mixture of hydrocarbons having an initial boiling point falling between about 75 F. and about 135 F. and an end-boiling point falling between about 250 F. and about 450 F.
- the boiling range of the gasoline reflects on its volatility. Thus, a higher boiling gasoline will be less volatile and give less stalling difficulty.. It has been proposed in the art that a gasoline having an A.S.T.M. mid-boiling (50%) point of 310 F.
- Another object is to provide a motor fuel adapted to prevent stalling during engine.
- this invention provides a motor gasoline containing a small amount, sufiicient to inhibit stalling, of the N-(N'aminoethyl)-aminoethyl alkenylsuccinamic acid of an alkenyl succinic acid having the formula:
- R is an alkenyl radical containing between 8 and 16 carbon atoms.
- alkenyl succinamic acids contemplated herein are readily prepared by reacting equimolar amounts of an alkenyl succinic acid anhydride and diethylenetriamine, without formation of water of condensation.
- the condensation takes place readily upon heating the acid anhydride reactant and the diethylenetriamine at temperatures ranging from ambient temperatures and upwards.
- the reaction is an amide formation reaction effected by the well-known addition of the anhydride group to an amino group. This addition proceeds at any temperature, but temperatures of about C. or lower are preferred.
- the time of reaction is dependent on the size of the charge and the reaction temperature selected.
- Ordinarily addition of the acid anhydride is substantially com- CHg-C wherein R is an alkenyl radical having between 8 and.16
- Non-limiting examples are octenylsuccinic acid” anhydride, diisobutenyl succinic acid anhydride, 2-methyl-g heptenyl succinic acid anhydride, 4-ethyl-hexenyl succinicf acid anhydride, nonenyl succinic acid anhydride,*decenyl succinic acid anhydride, undecenyl succinic acid; anhyrii dride, dodecenyl succinic acid anhydride, triisobutenyl succinic acid anhydride, tetrapropenyl succinic acid 61 ,3. hydride, tetradecenyl succinic acid anhydride, and hexadecenyl succinc acd anhydride.
- the compounds contemplated can be prepared from the corresponding alkenyl succinic acid.
- the diethylene triamine is accompanied by formation of one mole of water of condensation per mole of amine.
- the reaction in this case, is carried out at temperatures of between about 130 C. and about 160 C., although the reaction can be effected at temperatures above and below this range.
- the reaction will proceed until one mole of water is evolved per mole of alkenyl succinic acid reactant, usually six to ten hours.
- a hydrocarbon solvent which forms an azeotropic mixture with water can be added to the reaction mixture. Heating is continued until removal of water by azeotropic distillation has substantially ceased. Examples of wellknown solvents that form azeotropes are benzene, toluene, and xylene.
- the alkenyl suceinamic acid can exist in either or both of the following structural forms:
- N-(Naminoethyl) aminoethyl alkenylsuccinami acid that is added to the motor gasoline will vary between about 0.005 percent and about 0.5 percent, by weight, of the gasoline. In preferred practice, amounts varying between about 0.01 percent and about 0.05 percent, by weight, are used
- the antistall additives of the invention may be used in the gasoline along with other antlstall addition agents or other additives designed to impart other improved properties thereto. Thus, anti-knock agents, pre-ignition inhibitors, anti-rest agents, metal-deactivators, dyes, antioxidants, detergents, etc., may be present in the gasoline.
- the gasoline may contain a small amount, from about 0.01 percent to about 1 percent, by weight, of a solvent oil or upperlube.
- Suitable oils include Coastal and Mid-Continent distillate oils having viscosities within the range of from about 50 to about 500 S.U.S. at 100 F.
- Synthetic oils such as diester oils, polyalkylene glycols, silicones, phosphate esters, polypropylenes, polybutylenes and the like, may also be used.
- HILLMAN-MINX ENGINE TEST A downdraft Solex FAI 30 carburetor was mounted on a standard 1953 Hillman-Minx engine. The engine was connected to a 7.5 horsepower induction motor and operated under load at 2800 rpm. This was equiva-- lent to driving at about 40 miles per hour.
- the Solex carburetor was especially prone to icing .on its spraying well which is located in the center of the carburetor throat.
- the spraying well is a cylindrical metal tube with apertures through which a fuel-air mixture. is. sprayed. into. the..carburetor throat. Evaporation. of the fuel refrigerates the spraying well.
- a fuel rating was obtained by using these pressure readings to calculate the percentage of the carburetor throat area that would be blocked with ice after 20 minutes.
- the percent of annular area in the carburetor that is blocked by ice determines the amount of pressure drop across the annular opening in any given installation.
- the amount of throat area blocked by ice is related to the amount of pressure drop above and below'the point of ice deposition.
- the relationship between pressure drop and area blocked was determined to'calibrate the carburetor, as follows:
- a series of flanged cylinders were prepared, which fitted over the emulsion tube and blocked a portion of the annular opening.
- Each tube had a different, but known size flange. Thus, it was known what fraction of the annular area was blocked by each flange.
- the engine was operated with a flanged cylinder in the carburetor and the amount of pressure drop was noted and recorded. This operation was repeated with each flange.
- i Z anhydride is a C radical obtained from tetrapropylene, i.-e., propylene tetramer. Blends of this N-( N aminoethyl) aminoethyl tetrapropenylsuccinamic acid in test gasoline were subjected to the Hillman-Minx engine test. Pertinent data and test results are set forth in Table I.
- R-CH-COOH Ha-COOH wherein R is an alkenyl radical containing between v8 and 16 carbon atoms.
- a motor gasoline containing between about 0.005 percent and about 0.5 percent, by weight, of the N-(N'- am-inoethyl)-aminoethyl alkenylsuccinamic acid of an alkenyl succinic acid having the formula:
- R is an alkenyl radical containing between 8 and 16 carbon atoms.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Liquid Carbonaceous Fuels (AREA)
Description
N-SUBSTITUTED ALKENYL SUCCINAMIC ACID DEICER Harry Andress, Jr., Pitman, NJ., assignor to Socony Mobil Oil Company, Inc., a corporation of New York No Drawing. Filed Jan. 16, 1959, Ser. No. 787,133
3 Claims. (Cl. 44-71) This invention relates to gasoline compositions adapted to improve the operation of internal combustion engines. It is more particularly concerned with motor fuels that provide improved engine operation under cool, humid weather conditions.
As is well-known to those skilled in the art, frequent stalling of automobile engines, especially during the warmup period, has been a common occurrence. This difliculty is most pronounced in postwar cars having automatic transmissions and a consequent limit on the maximum permissible idle speed, although it also occurs in cars without automatic transmissions. Stalling of this type, of course, is a definite safety hazard, as Well as a dccided inconvenience in frequent restarting of the engine.
It is now recognized that stalling during the warmup period is attributable to the formation of ice on the throttle plate and the carburetor barrel near it. The water which forms the ice does not come from the gasoline, i.e., as entrained water, but from the air that enters the carburetor. As has been mentioned hereinbefore, stalling generally occurs in cool, humid weather, when the temperatures are above about 30 F. and below about 60 F. and the relative humidity is about 65 percent and higher, up to 100 percent. The most critical conditions are temperatures of 3540 F. and 100 percent relative humidity.
As the gasoline evaporates in the carburetor, it reduces the temperature of the surrounding metal by as much as 40 F. 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 more moist this air is, the greater the buildup of ice. Then, when the engine is idled, the throttle plate closes and the ice chokes ofi the normal small 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.
Icing may also occur in the carburetors of some vehicles when cruising at speeds of 30-60 m.p.h. Such icing is a particular problem in the case of certain trucks and cars equipped with carburetors having Venturi-type fuel-air mixing tubes (emulsion tubes). Such carburetors are found in trucks and in many European cars. The ice builds up in the tube and restricts the flow of air, thereby enriching the fuel mixture and reducing efiiciency. Eventually the engine may stall.
Gasoline is a mixture of hydrocarbons having an initial boiling point falling between about 75 F. and about 135 F. and an end-boiling point falling between about 250 F. and about 450 F. The boiling range of the gasoline, of course, reflects on its volatility. Thus, a higher boiling gasoline will be less volatile and give less stalling difficulty.. It has been proposed in the art that a gasoline having an A.S.T.M. mid-boiling (50%) point of 310 F.
or higher will not be subject to stalling. Although this may be the case for a given series of gasoline, however,
. Patented May 2, 1 961 2 a it .is not the sole and controlling factor. Gasolines of higher mid-boiling point but a low initial boiling point (e.g., full boiling range gasolines) can induce stalling when the aforementioned stall-inducing atmospheric conditio'ns are prevalent. Thus, any gasoline will give difliculty in damp, cool'weather. In modern engine operation, however, control of stalling by means of volatility is not feasible, because other performance characteristics. are affected.
It has now been found that stalling during engine warmup can be overcome simply and economically. It has been discovered that small amounts of certain N-substituted alkenylsuccinamic acids, when added to motor gasoline, will overcome stalling difficulties attributable to carburetor icing.
Accordingly, it is an object of this invention to provide an improved moto'r fuel. Another object is to provide a motor fuel adapted to prevent stalling during engine.
warmup in cool, humid weather. A specific object is to provide an antistall gasoline containing certain alkenylsuccinamic acids. Other-objects and advantages of this invention will become apparent to those skilled in the art, from the following detailed description.
In general, this invention provides a motor gasoline containing a small amount, sufiicient to inhibit stalling, of the N-(N'aminoethyl)-aminoethyl alkenylsuccinamic acid of an alkenyl succinic acid having the formula:
wherein R is an alkenyl radical containing between 8 and 16 carbon atoms.
The alkenyl succinamic acids contemplated herein are readily prepared by reacting equimolar amounts of an alkenyl succinic acid anhydride and diethylenetriamine, without formation of water of condensation. The condensation takes place readily upon heating the acid anhydride reactant and the diethylenetriamine at temperatures ranging from ambient temperatures and upwards. The reaction is an amide formation reaction effected by the well-known addition of the anhydride group to an amino group. This addition proceeds at any temperature, but temperatures of about C. or lower are preferred. The time of reaction is dependent on the size of the charge and the reaction temperature selected. Ordinarily addition of the acid anhydride is substantially com- CHg-C wherein R is an alkenyl radical having between 8 and.16
carbon atoms and preferably between 10 and 14 carbon? atoms. Non-limiting examples are octenylsuccinic acid" anhydride, diisobutenyl succinic acid anhydride, 2-methyl-g heptenyl succinic acid anhydride, 4-ethyl-hexenyl succinicf acid anhydride, nonenyl succinic acid anhydride,*decenyl succinic acid anhydride, undecenyl succinic acid; anhyrii dride, dodecenyl succinic acid anhydride, triisobutenyl succinic acid anhydride, tetrapropenyl succinic acid 61 ,3. hydride, tetradecenyl succinic acid anhydride, and hexadecenyl succinc acd anhydride.
Although the anhydride is preferred, the compounds contemplated can be prepared from the corresponding alkenyl succinic acid. In this case, thereactionwiththe diethylene triamine is accompanied by formation of one mole of water of condensation per mole of amine. The reaction, in this case, is carried out at temperatures of between about 130 C. and about 160 C., although the reaction can be effected at temperatures above and below this range. The reaction will proceed until one mole of water is evolved per mole of alkenyl succinic acid reactant, usually six to ten hours. In' order to facilitate the removal of water, to effect a more complete reaction in accordance with the principle of Le Chatelier, a hydrocarbon solvent which forms an azeotropic mixture with water can be added to the reaction mixture. Heating is continued until removal of water by azeotropic distillation has substantially ceased. Examples of wellknown solvents that form azeotropes are benzene, toluene, and xylene.
The alkenyl suceinamic acid can exist in either or both of the following structural forms:
R-CH-L-NH CHzCHzNH CHzCHzNH:
O CHr-OH The amount of N-(Naminoethyl) aminoethyl alkenylsuccinami acid that is added to the motor gasoline will vary between about 0.005 percent and about 0.5 percent, by weight, of the gasoline. In preferred practice, amounts varying between about 0.01 percent and about 0.05 percent, by weight, are used The antistall additives of the invention may be used in the gasoline along with other antlstall addition agents or other additives designed to impart other improved properties thereto. Thus, anti-knock agents, pre-ignition inhibitors, anti-rest agents, metal-deactivators, dyes, antioxidants, detergents, etc., may be present in the gasoline. Also, the gasoline may contain a small amount, from about 0.01 percent to about 1 percent, by weight, of a solvent oil or upperlube. Suitable oils, for example, include Coastal and Mid-Continent distillate oils having viscosities within the range of from about 50 to about 500 S.U.S. at 100 F. Synthetic oils, such as diester oils, polyalkylene glycols, silicones, phosphate esters, polypropylenes, polybutylenes and the like, may also be used.
The following examples are for the purpose of illustrating this invention and demonstrating the effectiveness thereof. This invention is not to be limited to the specific compositions set forth in the examples or to 'the operations and manipulations involved. Other materials and formulations as described hereinbefore can be used, as those skilled in the art will readily understand.
The ability of an additive to inhibit icing is demonstrated in the following test:
HILLMAN-MINX ENGINE TEST A downdraft Solex FAI 30 carburetor was mounted on a standard 1953 Hillman-Minx engine. The engine was connected to a 7.5 horsepower induction motor and operated under load at 2800 rpm. This was equiva-- lent to driving at about 40 miles per hour.
The Solex carburetor was especially prone to icing .on its spraying well which is located in the center of the carburetor throat. The spraying well is a cylindrical metal tube with apertures through which a fuel-air mixture. is. sprayed. into. the..carburetor throat. Evaporation. of the fuel refrigerates the spraying well.
As ice formed on the wellit restricted the flow of air through the'carburetor and caused a drop in pressure. This pressure change was recorded by a manometer connected above and below the point of ice deposition. Temperatures at this point were measured by a thermocouple. attached to the well. The entire carburetor was enclosed in an asbestos chamber that was connected to an ice tower. Air at 34-37 F. and 90-100 percent relative humidity was passed through the carburetor at constant velocity.
In conducting a test the engine was first run until the spraying well reached an equilibrium temperature of about 2025 F. The fuel flow was then stopped and the engine was driven by the induction motor until the spraying well reached 45 F. (warm ambient air was admitted to the carburetor during this period). Fuel flow was now restored to the engine and the run was: started. As the engine operated under load, ice deposited. on the spraying well. The pressure drop across the ice formation was recorded at one-minute intervals for 20 minutes. Several tests were made on each fuel blend and the results were averaged.
A fuel rating was obtained by using these pressure readings to calculate the percentage of the carburetor throat area that would be blocked with ice after 20 minutes. The percent of annular area in the carburetor that is blocked by ice determines the amount of pressure drop across the annular opening in any given installation. Thus, for each carburetor, the amount of throat area blocked by ice is related to the amount of pressure drop above and below'the point of ice deposition. The relationship between pressure drop and area blocked was determined to'calibrate the carburetor, as follows:
A series of flanged cylinders were prepared, which fitted over the emulsion tube and blocked a portion of the annular opening. Each tube had a different, but known size flange. Thus, it was known what fraction of the annular area was blocked by each flange. The engine was operated with a flanged cylinder in the carburetor and the amount of pressure drop was noted and recorded. This operation was repeated with each flange.
From thedata, thus obtained, the relationship between pressure drop and amount of throat area blocked was plotted. Then, when runs were made using blank fuel or inhibited (test) fuel, but with no flanged inserts in the carburetor, the throat area blocked by ice was determined from the amount of pressure drop. The average area blocked during the 20-minute run is obtained from the summation of the one-minute observations.
. It will be appreciated, of course, that calibration curves will vary with each carburetor, but any carburetor can be readily calibrated as aforedescribed. As is the case in many test procedures, results can vary from time to time, because of slight variations in test conditions, vapor pressure of fuel, and even techniques of individual operators. Thus, each day a test run is made, a blank fuel should be run. This provides a reference point, so that even if values determined may not be finite, comparison of a testfuel result with the resulton the blank fuel gives Example A succinamic acid was prepared by heating one mole of tetrapropenyl succinic acid anhydride with a mcie of. diethylenetriamine, using a xylene diluent, at. a tempera ture of -90 C for 2 hours. The alkenylgroup of this.
i Z anhydride is a C radical obtained from tetrapropylene, i.-e., propylene tetramer. Blends of this N-( N aminoethyl) aminoethyl tetrapropenylsuccinamic acid in test gasoline were subjected to the Hillman-Minx engine test. Pertinent data and test results are set forth in Table I.
It will be apparent from the data in Table I, that the additives of this invention are effective antistall additives for gasoline. They are not all equivalent in performance, however.
Although the present invention has been described with preferred embodiments, it is to be understood that modifications and variations may be resorted to, without departing from the spirit and scope of this invention, as those skilled in the art will readily understand. Such variations and modifications are considered to be within the purview and scope of the appended claims.
What is claimed is:
1. A motor gasoline containing a small amount, sulficient to inhibit icing, of the N-(N'aminoethyl)-aminoethyl alkenylsuccinamic acid of an alkenyl succinic acid having the formula:
R-CH-COOH Ha-COOH wherein R is an alkenyl radical containing between v8 and 16 carbon atoms.
2. A motor gasoline containing between about 0.005 percent and about 0.5 percent, by weight, of the N-(N'- am-inoethyl)-aminoethyl alkenylsuccinamic acid of an alkenyl succinic acid having the formula:
- R-OH-COOH CHz-COOH 10 wherein R is an alkenyl radical containing between 8 and 16 carbon atoms.
3. A motor gasoline containing between about 0.01
percent and about 0.05 percent, by weight, of the N- (N'aminoethyl) -aminoethyl tetrapropenylsuccinamic acid.-
References Cited in the file of this patent UNITED STATES PATENTS OTHER REFERENCES Petroleum Refining with Chemicals, Kalichevsky and Kobe, Elsevier Pub. Co., 1956, page 480.
Claims (1)
1. A MOTOR GASOLINE CONTAINING A SMALL AMOUNT, SUFFICIENT TO INHIBIT ICING, OFTHE N-(N''AMINOETHYL)-AMINOETHYL ALKENYLSUCCIAMIC ACID OF AN ALKENYL SUCCINIC ACID HAVING THE FORMULA:
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US787133A US2982633A (en) | 1959-01-16 | 1959-01-16 | N-substituted alkenyl succinamic acid deicer |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US787133A US2982633A (en) | 1959-01-16 | 1959-01-16 | N-substituted alkenyl succinamic acid deicer |
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US2982633A true US2982633A (en) | 1961-05-02 |
Family
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Application Number | Title | Priority Date | Filing Date |
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US787133A Expired - Lifetime US2982633A (en) | 1959-01-16 | 1959-01-16 | N-substituted alkenyl succinamic acid deicer |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3148960A (en) * | 1961-07-11 | 1964-09-15 | Socony Mobil Oil Co Inc | Nu-aminoethyl alkenyl succinamic acid deicer |
US3280033A (en) * | 1962-08-30 | 1966-10-18 | Exxon Research Engineering Co | Alkenyl succinamic acids as rust inhibitors and dispersants |
US3409646A (en) * | 1965-08-10 | 1968-11-05 | Rohm & Haas | Aminoamides |
EP0008953A2 (en) * | 1978-09-11 | 1980-03-19 | Mobil Oil Corporation | Fuel containing novel detergent |
EP0393769A1 (en) * | 1989-04-21 | 1990-10-24 | AGIP PETROLI S.p.A. | Detergent, dispersant and anti-rust additive for fuels and lubricating oils |
Citations (7)
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US2604451A (en) * | 1948-09-16 | 1952-07-22 | Gulf Research Development Co | Mineral oil compositions |
US2638450A (en) * | 1950-01-17 | 1953-05-12 | Socony Vacuum Oil Co Inc | Reaction products of nu-alkylated polyalkylenepolyamines and alkenyl succinic acid anhydrides |
US2706677A (en) * | 1950-06-28 | 1955-04-19 | Exxon Research Engineering Co | Amines and amides as anti-stalling additives |
US2843464A (en) * | 1956-04-06 | 1958-07-15 | Gulf Research Development Co | Non-stalling gasoline fuel compositions |
US2862800A (en) * | 1956-11-06 | 1958-12-02 | Gulf Oil Corp | Gasoline fuels |
US2886423A (en) * | 1956-07-09 | 1959-05-12 | American Cyanamid Co | Hydrocarbon fuels containing betaine antifreeze compositions |
US2906613A (en) * | 1956-06-21 | 1959-09-29 | Sun Oil Co | Suppression of fuel icing |
-
1959
- 1959-01-16 US US787133A patent/US2982633A/en not_active Expired - Lifetime
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2604451A (en) * | 1948-09-16 | 1952-07-22 | Gulf Research Development Co | Mineral oil compositions |
US2638450A (en) * | 1950-01-17 | 1953-05-12 | Socony Vacuum Oil Co Inc | Reaction products of nu-alkylated polyalkylenepolyamines and alkenyl succinic acid anhydrides |
US2706677A (en) * | 1950-06-28 | 1955-04-19 | Exxon Research Engineering Co | Amines and amides as anti-stalling additives |
US2843464A (en) * | 1956-04-06 | 1958-07-15 | Gulf Research Development Co | Non-stalling gasoline fuel compositions |
US2906613A (en) * | 1956-06-21 | 1959-09-29 | Sun Oil Co | Suppression of fuel icing |
US2886423A (en) * | 1956-07-09 | 1959-05-12 | American Cyanamid Co | Hydrocarbon fuels containing betaine antifreeze compositions |
US2862800A (en) * | 1956-11-06 | 1958-12-02 | Gulf Oil Corp | Gasoline fuels |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3148960A (en) * | 1961-07-11 | 1964-09-15 | Socony Mobil Oil Co Inc | Nu-aminoethyl alkenyl succinamic acid deicer |
US3280033A (en) * | 1962-08-30 | 1966-10-18 | Exxon Research Engineering Co | Alkenyl succinamic acids as rust inhibitors and dispersants |
US3409646A (en) * | 1965-08-10 | 1968-11-05 | Rohm & Haas | Aminoamides |
EP0008953A2 (en) * | 1978-09-11 | 1980-03-19 | Mobil Oil Corporation | Fuel containing novel detergent |
EP0008953A3 (en) * | 1978-09-11 | 1980-04-02 | Mobil Oil Corporation | Fuel containing novel detergent |
EP0393769A1 (en) * | 1989-04-21 | 1990-10-24 | AGIP PETROLI S.p.A. | Detergent, dispersant and anti-rust additive for fuels and lubricating oils |
AU621217B2 (en) * | 1989-04-21 | 1992-03-05 | Agip Petroli S.P.A. | Detergent, dispersant and anti-rust additive for fuels and lubricating oils |
US5156654A (en) * | 1989-04-21 | 1992-10-20 | Agip Petroli S.P.A. | Detergent, dispersant and anti-rust additive for fuels and lubricating oils |
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