US2445360A - Motor fuel - Google Patents
Motor fuel Download PDFInfo
- Publication number
- US2445360A US2445360A US694437A US69443746A US2445360A US 2445360 A US2445360 A US 2445360A US 694437 A US694437 A US 694437A US 69443746 A US69443746 A US 69443746A US 2445360 A US2445360 A US 2445360A
- Authority
- US
- United States
- Prior art keywords
- fuel
- aviation
- methylenecyclobutane
- accordance
- aviation fuel
- 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
Links
- 239000000446 fuel Substances 0.000 title description 36
- 238000009835 boiling Methods 0.000 description 12
- QIRVGKYPAOQVNP-UHFFFAOYSA-N methylidenecyclobutane Chemical compound C=C1CCC1 QIRVGKYPAOQVNP-UHFFFAOYSA-N 0.000 description 12
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- OYSVBCSOQFXYHK-UHFFFAOYSA-N 1,3-dibromo-2,2-bis(bromomethyl)propane Chemical compound BrCC(CBr)(CBr)CBr OYSVBCSOQFXYHK-UHFFFAOYSA-N 0.000 description 2
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Natural products CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical class NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000009194 climbing Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000694408 Isomeris Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 229940087654 iron carbonyl Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
- C10L1/023—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for spark ignition
Definitions
- the present invention relates to an aviation fuel and more particularly relates to a fuel composition which gives improved performance in the aviation motor.
- the problem of producing a proper fuel for use in the aviation motor is one that has attracted a large number of workers, due to the complexity of the requirements for a perfect fuel which will perform equally well under the different conditions encountered in the engine. For example,
- the fuel requirements of the aviation engine are quite different under cruising conditions" from the conditions obtaining when the engine is accelerating during take-off or while the airplane is climbing.
- the methylenecyclobutane may be employed in a fuel composition, the other constituents of which are predominantly isoparaifinic in nature.
- the fuel may comprise isopentane, isohexane, isoheptane, isooctane and the like.
- the improved fuel of my invention may also include amounts of tetraethyl lead, iron carbonyl and other anti-detonants such as the class of compounds illustrated by the amino toluenes.
- a fuel in accordance with the present invention which comprises methylenecyclobutane and quantities of the aromatics and/or naphthenes.
- fins, cracked gasoline components and the like either comprise the major portion of the fuel or be added thereto in substantial amounts.
- Addition of tetra-ethyl lead and other anti-detonants such as amino toluenes and their homologs has also been proposed. All of these expedients,
- an improved aviation fuel is produced by the employment of suitable quantities of the hydrocar- I bon methylenecyclobutane which has the structural configuration It is contemplated that the amount of methylenecyclobutane comprising the aviation fuel will 100 F. This limitation of vapor pressure is de- It may be pointed out that 6 Mixtures of the latter types of hydrocarbons with isoparafllns form suitable base stocks to which the methylenecyclobutane may be added.
- the isoparafllns may be obtained from naturally occurring sources or may be produced synthetically as :by the well known alkylation and/or isomeri'zation reactions. Irrespective of the source of the isoparaflins, it is preferred to employ them in my fuel composition in relatively pure form.
- Suitable fractions of crude petroleum from crude oils of the Coastal type, which boil in the gasoline boiling range, may also form the base stock of my improved fuel.
- the hydrocarbon fractions will not have a boiling point which exceeds 350 F.
- the tetraethyl lead may be employed in most instances, in amounts not exceeding 6 cc, per gallon of fuel.
- pentaerythrityl bromide As follows: g2 of pentaerythrityl bromide and 250 g. of zinc powder were placed in areaction flash and 250 cc. of 50% ethyl alcohol was slowly added. A hot water bath was placed around the flask until a localized reaction started. The product distilling over at 38 to 41 C. (l00.4-105.8 F.) was washed and dried over calcium chloride and-identified as methylenecyclobutane. It was tested by the A. S. T. M.
- an aviation fuel in accordance with the present invention may be prepared by addin: 20 parts of methylenecyclobutane to 80 parts of an alkylatehaving a vapor pressure of four major amount of isoparaflinic hydrocarbons boilpounds Reid.
- the vapor pressure of this composition is slightly over 6 pounds Reid and is satisfactory for use in an aviation motor.
- a fuel in accordance with the present invention, is prepared by blending 25 parts of methylene-cyolobutane with a mixture composed of equal parts of 2. 2,-dimethyl-butane, commonly called neohexane and iso-octane. This composition is also satisfactory for use as an aviation fuel.
- An aviation fuel consisting essentially of a minor portion of methylenecyclobutane and a major portion of hydrocarbons boiling in the gasoline boiling range.
- An aviation fuel in accordance with 'claim 5 inwhich the. minor amount of methylenecyclobutlane comprises less than 50% by volume of the fue '7.
- An aviation fuel in accordance with claim 1 which comprises tetraethyi lead.
- An aviation fuel in accordance with claim 5 which comprises tetraethyl lead.
- An aviation fuel consisting essentially of methylenecyciobutane as a minor component and a mixture of isoparaflinic, naphthenic and aromatic hydrocarbons boiling in the gasoline boiling range as a major component.
- An aviation fuel in accordance with claim 9 which comprises tetraethyl lead.
- An aviation fuel containing anti-detonants consisting essentially of a minor portion of metlhylenecyclobutane and a major portion of boiling in the gasoline boiling range.
Landscapes
- 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
Patented July 20, 1948 Pharis Miller, Mountainside, N. l auignor to Standard Oil Development Company, a corporation of Delaware No 1mm. Application sum a1, 1940, Serial No. seem 11 Claims. (Cl. 4H9) The present invention relates to an aviation fuel and more particularly relates to a fuel composition which gives improved performance in the aviation motor.
The problem of producing a proper fuel for use in the aviation motor is one that has attracted a large number of workers, due to the complexity of the requirements for a perfect fuel which will perform equally well under the different conditions encountered in the engine. For example,
the fuel requirements of the aviation engine are quite different under cruising conditions" from the conditions obtaining when the engine is accelerating during take-off or while the airplane is climbing.
As a solution to the problem of providing a proper aviation fuel suitable for use under the different conditions of operations, ithas been proposed that aromatics, naphthenes, isoparafsigned to prevent vapor lock and excessive evap'oration of the fuel. 7
The methylenecyclobutane may be employed in a fuel composition, the other constituents of which are predominantly isoparaifinic in nature.
' Thus. besides methylenecyclobutane, the fuel may comprise isopentane, isohexane, isoheptane, isooctane and the like. The improved fuel of my invention may also include amounts of tetraethyl lead, iron carbonyl and other anti-detonants such as the class of compounds illustrated by the amino toluenes.
In some instances it may be desirable to pre pare a fuel in accordance with the present invention which comprises methylenecyclobutane and quantities of the aromatics and/or naphthenes.
fins, cracked gasoline components and the like either comprise the major portion of the fuel or be added thereto in substantial amounts. Addition of tetra-ethyl lead and other anti-detonants such as amino toluenes and their homologs has also been proposed. All of these expedients,
while improving the various aviation fuel base stocks, provide an improvement in the fuels performance during either cruising conditions or during take-off or while the plane is climbing but not satisfying thefuel requirements suitable for both types of operation of the motor.
In accordance with the present invention, an improved aviation fuel is produced by the employment of suitable quantities of the hydrocar- I bon methylenecyclobutane which has the structural configuration It is contemplated that the amount of methylenecyclobutane comprising the aviation fuel will 100 F. This limitation of vapor pressure is de- It may be pointed out that 6 Mixtures of the latter types of hydrocarbons with isoparafllns form suitable base stocks to which the methylenecyclobutane may be added.
u The isoparafllns may be obtained from naturally occurring sources or may be produced synthetically as :by the well known alkylation and/or isomeri'zation reactions. Irrespective of the source of the isoparaflins, it is preferred to employ them in my fuel composition in relatively pure form. v
Suitable fractions of crude petroleum from crude oils of the Coastal type, which boil in the gasoline boiling range, may also form the base stock of my improved fuel. Generally, the hydrocarbon fractions will not have a boiling point which exceeds 350 F. 'When using crude petro leum fractions with methylenecyclobutane, it may be desirable to employ other blending agents such as alkylates and tetraethyl lead to obtain maximum utilization of the qualities of the admixture. The tetraethyl lead may be employed in most instances, in amounts not exceeding 6 cc, per gallon of fuel.
The compound methylenecyclobutane has been described in the literature (see for example Berichte der deutschen chemischen Gesellschaft v. 72:2021-2026 (1939) and Journal American Chemical Society v. 64:1142-7 (1942)).
It is suitably prepared from pentaerythrityl bromide as follows: g2 of pentaerythrityl bromide and 250 g. of zinc powder were placed in areaction flash and 250 cc. of 50% ethyl alcohol was slowly added. A hot water bath was placed around the flask until a localized reaction started. The product distilling over at 38 to 41 C. (l00.4-105.8 F.) was washed and dried over calcium chloride and-identified as methylenecyclobutane. It was tested by the A. S. T. M.
motor method and found to have a blending octane number of 99.
As a example ofthe, improved fuel composition, an aviation fuel in accordance with the present invention may be prepared by addin: 20 parts of methylenecyclobutane to 80 parts of an alkylatehaving a vapor pressure of four major amount of isoparaflinic hydrocarbons boilpounds Reid. The vapor pressure of this composition is slightly over 6 pounds Reid and is satisfactory for use in an aviation motor.
In another example, a fuel, in accordance with the present invention, is prepared by blending 25 parts of methylene-cyolobutane with a mixture composed of equal parts of 2. 2,-dimethyl-butane, commonly called neohexane and iso-octane. This composition is also satisfactory for use as an aviation fuel.
The nature and objects of the present invention having been described and illustrated, what is claimed as new and useful and desired to be secured by Letters Patent is:
1. An aviation fuel consisting essentially of a minor portion of methylenecyclobutane and a major portion of hydrocarbons boiling in the gasoline boiling range.
2. An aviation fuel in accordance with claim 1 in which the hydrocarbons boiling in the gasoline boiling range are obtained from crude petroleum.
3. An aviation fuel in accordance with claim 1 in which the hydrocarbons boiling in the gasoline range are produced synthetically.
4. An aviation fuel in accordance with claim 1 in which the methvlenecyclobutane comprises less than 50% by volume of the fuel.
5.'An aviation fuel consisting essentially of a minor amount of methylenecyclobutane and a hydrocarbons ing in the asoline boiling range.
a. An aviation fuel in accordance with 'claim 5 inwhich the. minor amount of methylenecyclobutlane comprises less than 50% by volume of the fue '7. An aviation fuel in accordance with claim 1 which comprises tetraethyi lead.
8. An aviation fuel in accordance with claim 5 which comprises tetraethyl lead.
9. An aviation fuel consisting essentially of methylenecyciobutane as a minor component and a mixture of isoparaflinic, naphthenic and aromatic hydrocarbons boiling in the gasoline boiling range as a major component.
10. An aviation fuel in accordance with claim 9 which comprises tetraethyl lead. v
11. An aviation fuel containing anti-detonants consisting essentially of a minor portion of metlhylenecyclobutane and a major portion of boiling in the gasoline boiling range.
PHARIS MILLER.
,BEFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS nautics, Technical Note 1023, February 1946, pages i-9.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US694437A US2445360A (en) | 1946-08-31 | 1946-08-31 | Motor fuel |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US694437A US2445360A (en) | 1946-08-31 | 1946-08-31 | Motor fuel |
Publications (1)
Publication Number | Publication Date |
---|---|
US2445360A true US2445360A (en) | 1948-07-20 |
Family
ID=24788820
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US694437A Expired - Lifetime US2445360A (en) | 1946-08-31 | 1946-08-31 | Motor fuel |
Country Status (1)
Country | Link |
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US (1) | US2445360A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2622971A (en) * | 1947-12-17 | 1952-12-23 | California Research Corp | Amino phenols as rich mixture additives |
US2712497A (en) * | 1949-10-28 | 1955-07-05 | Phillips Petroleum Co | Jet engine fuel |
US2761770A (en) * | 1951-09-26 | 1956-09-04 | Phillips Petroleum Co | Aviation gasoline |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2407717A (en) * | 1942-07-01 | 1946-09-17 | Standard Oil Co | Aviation superfuel |
US2411582A (en) * | 1944-06-10 | 1946-11-26 | Standard Oil Dev Co | Aviation fuel |
-
1946
- 1946-08-31 US US694437A patent/US2445360A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2407717A (en) * | 1942-07-01 | 1946-09-17 | Standard Oil Co | Aviation superfuel |
US2411582A (en) * | 1944-06-10 | 1946-11-26 | Standard Oil Dev Co | Aviation fuel |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2622971A (en) * | 1947-12-17 | 1952-12-23 | California Research Corp | Amino phenols as rich mixture additives |
US2712497A (en) * | 1949-10-28 | 1955-07-05 | Phillips Petroleum Co | Jet engine fuel |
US2761770A (en) * | 1951-09-26 | 1956-09-04 | Phillips Petroleum Co | Aviation gasoline |
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