US2657984A - Fuel oils - Google Patents

Fuel oils Download PDF

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Publication number
US2657984A
US2657984A US191332A US19133250A US2657984A US 2657984 A US2657984 A US 2657984A US 191332 A US191332 A US 191332A US 19133250 A US19133250 A US 19133250A US 2657984 A US2657984 A US 2657984A
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US
United States
Prior art keywords
pour
point
weight
fuel oils
minor
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
US191332A
Inventor
Jr Charles Henry Braithwaite
Martin George Ambrose
Sutton Reid Edward
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Shell Development Co
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Shell Development Co
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Filing date
Publication date
Priority to NL79072D priority Critical patent/NL79072C/xx
Priority to BE506531D priority patent/BE506531A/xx
Application filed by Shell Development Co filed Critical Shell Development Co
Priority to US191332A priority patent/US2657984A/en
Priority to GB24309/51A priority patent/GB710515A/en
Priority to DEN4575A priority patent/DE894296C/en
Application granted granted Critical
Publication of US2657984A publication Critical patent/US2657984A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C10L1/2227—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond urea; derivatives thereof; urethane
    • 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
    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2425—Thiocarbonic acids and derivatives thereof, e.g. xanthates; Thiocarbamic acids or derivatives thereof, e.g. dithio-carbamates; Thiurams

Definitions

  • This invention relates to petroleum fuels and, more particularly, to novel fuel oil compositions having greatly improved pour-point characteristics.
  • pour-point One of the characteristics of fuel oils which is limited by standardized specifications is the property known as pour-point. Because of this requirement that fuel oils have a specified minimum pour point, rather severe limitations are inherently placed upon the relative quantities of gasolines, light distillate oils, residual fuels, etc., which may be produced from a given crude petroleum stock. For example, in order to meet the pour-point specification, a distillate furnace oil must contain a certain proportion of fairly light components, or cannot contain more than a certain proportion of heavy components. If, however, the pour point of the fuel is reduced in some manner, a smaller proportion of the volatile components is required in the furnace oil, and larger quantities of lighter distillates such as kerosene and gasoline can be produced. Likewise, during periods of peak demand for fuel oils, greater quantities of such oils can be produced by including therein larger amounts of heavier fractions. Other beneficial results of a suitable means of lowering the pour point of fuel oils will be obvious to those skilled in the art.
  • the preferred organic radicals are hydrocarbon radicals, which may be aliphatic or cyclic, straight or branched chain, saturated, unsaturated or aromatic or any combination thereof.
  • the hydrocarbon radicals may be, for example, alkyl, alkenyl, aryl, alkaryl, aralkyl, etc.
  • the ureas may be substituted with other than pure hydrocarbyl radicals.
  • the hydrocarbyl radical may be substituted with amino, hydroxy, alkoxy, aryloxy, carboxylate, oxo, halogen, or like substituents; or the nitrogen of the urea may be directly attached to a non-carbon atom, such as another nitrogen atom, to form semicarbazides, semicarbazones, and the like.
  • ureas are the preferred embodiment of the present invention
  • non-urea materials having the structure of Formula 1 may be used if desired.
  • amides or substituted amides, carbamates, amidines such as guanidine or stearamidine, etc, are all effective, provided the solubility requirement is met.
  • combinations of the above essential structure may be used, as in biuret, or derivatives thereof.
  • the No. 2 fuel has the following properties:
  • pour-point depressant was used at a concentration of 0.0015 per cent by weight.
  • R1 is a hydrocarbyl radical and R2 is selected from the group consisting of hydrogen atoms and hydrocarbyl radicals.
  • R1 is a hydrocarbyl radical and R2 is selected from the group consisting of hydrogen atoms and hydrocarbyl radicals.
  • X is a chalkogen having an atomic number of from 8 to 16, said compound having at least one hydrocarbyl group attached to a nitrogen atom.

Description

Patented Nov. 3, 1953 FUEL OILS Charles Henry Braithwaite, Jr., Wood River, and George Ambrose Martin and Reid Edward Sutton, East Alton, Ill., assignors to Shell Development Company, San Francisco, Calif., a corporation of Delaware No Drawing. Application October 20, 1950, Serial No. 191,332
11 Claims. 1
This invention relates to petroleum fuels and, more particularly, to novel fuel oil compositions having greatly improved pour-point characteristics.
One of the characteristics of fuel oils which is limited by standardized specifications is the property known as pour-point. Because of this requirement that fuel oils have a specified minimum pour point, rather severe limitations are inherently placed upon the relative quantities of gasolines, light distillate oils, residual fuels, etc., which may be produced from a given crude petroleum stock. For example, in order to meet the pour-point specification, a distillate furnace oil must contain a certain proportion of fairly light components, or cannot contain more than a certain proportion of heavy components. If, however, the pour point of the fuel is reduced in some manner, a smaller proportion of the volatile components is required in the furnace oil, and larger quantities of lighter distillates such as kerosene and gasoline can be produced. Likewise, during periods of peak demand for fuel oils, greater quantities of such oils can be produced by including therein larger amounts of heavier fractions. Other beneficial results of a suitable means of lowering the pour point of fuel oils will be obvious to those skilled in the art.
It has now been found that the pour point of a petroleum fuel oil may be lowered by the inclusion of small amounts of a compound containing the structural group,
if CN (1) where X is a chalkogen or an NH group. It will be noted that the above formula gives one a wide choice of satisfactory materials, the only limitation being that the compound should have a solubility in the oil greater than about 0.0005 per cent by weight, and preferably greater than about 0.001 per cent by weight. A particularly effective embodiment of the invention is obtained when the bond on the carbon atom in Formula 1 is I satisfied by an amino or substituted amino group and X is an oxygen or sulfur atom. These ureas,
ciently soluble in most fuel oils. The preferred organic radicals are hydrocarbon radicals, which may be aliphatic or cyclic, straight or branched chain, saturated, unsaturated or aromatic or any combination thereof. Thus, the hydrocarbon radicals may be, for example, alkyl, alkenyl, aryl, alkaryl, aralkyl, etc.
The ureas may be substituted with other than pure hydrocarbyl radicals. For example, the hydrocarbyl radical may be substituted with amino, hydroxy, alkoxy, aryloxy, carboxylate, oxo, halogen, or like substituents; or the nitrogen of the urea may be directly attached to a non-carbon atom, such as another nitrogen atom, to form semicarbazides, semicarbazones, and the like.
While the ureas are the preferred embodiment of the present invention, non-urea materials having the structure of Formula 1 may be used if desired. For example, amides or substituted amides, carbamates, amidines such as guanidine or stearamidine, etc, are all effective, provided the solubility requirement is met. Likewise, combinations of the above essential structure may be used, as in biuret, or derivatives thereof.
The foregoing describes in relatively general terms the structural requirements and physical properties of the additives of the present invention. For specific examples of satisfactory compounds, reference may be had to the tables presented below. The data therein were obtained by measuring the pour points (determined according to ASTM Specification 13-97-47 except that observations were made at temperature intervals of 2 F. rather than 5 F., and two or more determinations were made on each specimen and the average result reported) of a Numher 2 fuel 011 (ASTM Specification D-396-39T), f
with and without the various pour-point depressants of this invention.
The No. 2 fuel has the following properties:
Unless otherwise noted, the pour-point depressant was used at a concentration of 0.0015 per cent by weight.
depressing amount of a metal-free compound having the formula,
wherein R1 is a hydrocarbyl radical and R2 is selected from the group consisting of hydrogen atoms and hydrocarbyl radicals.
4. A distillate fuel oil having an initial pour point of at least about F. containing dissolved therein a minor but eiTective pour-point depressing amount of a metal-free compound having the formula,
wherein R1 is a hydrocarbyl radical and R2 is selected from the group consisting of hydrogen atoms and hydrocarbyl radicals.
5. A fuel oil having an initial pour point of at least about 10 F. containing dissolved therein a minor but effective pour-point depressing amount of a metal-free compound having the formula,
X N N wherein X is a chalkogen having an atomic number of from 8 to 16, said compound having at least one hydrocarbyl group attached to a nitrogen atom.
7. A distillate fuel oil having an initial pour point of at least 10 F. containing a minor but effective pour-point depressing amount of lauryl urea dissolved therein in amount greater than 0.0005% by weight and not greater than 1.0% by weight.
8. A distillate fuel oil having an initial pour point of at least 10 F. containing a minor but effective pour-point depressing amount of N- phenyl N n butyl N .phenylurea dissolved therein in an amount greater than 0.0005% by weight and not greater than 1.0% by weight.
9. A distillate fuel oil having an initial pour point of at least 10 F. containing a minor but efiective pour-point depressing amount of N- phenyl N n propyl-N-phenylurea dissolved therein in an amount greater than 0.0005% by weight and not greater than 1.0% by weight.
10. A distillate fuel oil having an initial pour point of at least 10 F. containing a minor but effective pour-point depressing amount of phenylthiourea dissolved therein in an amount greater than 0.0005% by weight and not greater than 1.0% by weight.
11. A distillate fuel oil having an initial pour point of at least 10 F. containing a minor but eifective pour-point depressing amount of stearylurea dissolved therein in an amount greater than 0.0005% by weight and not greater than 1.0% by weight.
CHARLES HENRY BRAITI-IWAITE, JR. GEORGE AMBROSE MARTIN. REID EDWARD SUTTON.
References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 2,263,445 Reiff Nov. 18, 1941 2,343,393 Bergen Mar. '7, 1944 2,373,049 Pedersen Apr. 3, 1945 2,393,934 Reifif Jan. 29, 1946 2,396,156 Clarkson Mar. 5, 1946 FOREIGN PATENTS Number Country Date 312,774 Great Britain June 6, 1929

Claims (1)

1. A DISTILLATE FUEL OIL HAVING AN INITIAL POURPOINT OF AT LEAST ABOUT 10* F. CONTAINING DISSOLVED THEREIN A MINOR BUT EFFECTIVE POUR-POINT DEPRESSING AMOUNT OF A METAL-FREE COMPOUND HAVING THE FORMULA.
US191332A 1950-10-20 1950-10-20 Fuel oils Expired - Lifetime US2657984A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
NL79072D NL79072C (en) 1950-10-20
BE506531D BE506531A (en) 1950-10-20
US191332A US2657984A (en) 1950-10-20 1950-10-20 Fuel oils
GB24309/51A GB710515A (en) 1950-10-20 1951-10-18 Fuel oil compositions
DEN4575A DE894296C (en) 1950-10-20 1951-10-20 Fuel oil mixtures

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US191332A US2657984A (en) 1950-10-20 1950-10-20 Fuel oils

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US2657984A true US2657984A (en) 1953-11-03

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DE (1) DE894296C (en)
GB (1) GB710515A (en)
NL (1) NL79072C (en)

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2683081A (en) * 1950-12-09 1954-07-06 Ethyl Corp Stabilized organic compositions
US2683082A (en) * 1950-12-09 1954-07-06 Ethyl Corp Nu-aryl-nu'-(p-hydroxyphenyl) ureas as antioxidants for petroleum hydrocarbon fuels
US2813783A (en) * 1953-05-18 1957-11-19 Universal Oil Prod Co Stabilization of organic compounds
US2842433A (en) * 1956-11-19 1958-07-08 Texas Co Motor fuel composition
US2879230A (en) * 1956-11-19 1959-03-24 Texas Co Motor lubricating oil composition
US2908647A (en) * 1954-01-28 1959-10-13 Tide Water Oil Company Pour point reduction
US3092474A (en) * 1960-04-25 1963-06-04 Standard Oil Co Fuel oil composition
US3164553A (en) * 1960-12-16 1965-01-05 Union Carbide Corp Process of treating synthetic lubricating oils with urea
US3166387A (en) * 1961-07-17 1965-01-19 Standard Oil Co Ammonium carboxylate pour point depressants for fuel oil composition
US3190763A (en) * 1960-12-17 1965-06-22 Hoechst Ag Process for the anti-static finishing of high molecular weight compounds
US3278292A (en) * 1963-01-02 1966-10-11 Du Pont Herbicidal compositions and methods employing 3-phenyl-3-alkoxyureas
US3296136A (en) * 1963-11-13 1967-01-03 Sinclair Research Inc Lubricant compositions of improved oxidation resistance
FR2436814A1 (en) * 1977-06-20 1980-04-18 Shell Int Research COMBUSTIBLE AND LUBRICATING OIL COMPOSITIONS
US4401439A (en) * 1981-12-31 1983-08-30 Shell Oil Company Fuel and lubricant compositions for octane requirement reduction
US4416669A (en) * 1982-02-22 1983-11-22 Shell Oil Company Fuel and lubricant compositions for octane requirement reduction
US4435187A (en) 1981-12-31 1984-03-06 Shell Oil Company Fuel and lubricant compositions for octane requirement reduction
US5425789A (en) * 1986-12-22 1995-06-20 Exxon Chemical Patents Inc. Chemical compositions and their use as fuel additives
US5746783A (en) * 1994-03-30 1998-05-05 Martin Marietta Energy Systems, Inc. Low emissions diesel fuel
US5997593A (en) * 1998-12-22 1999-12-07 Ethyl Corporation Fuels with enhanced lubricity
US6725651B2 (en) * 2000-11-16 2004-04-27 Toyota Jidosha Kabushiki Kaisha Reducing agent for emission control system, reducing-agent supply device, and emission control system using the reducing agent
WO2013131800A1 (en) 2012-03-07 2013-09-12 Basf Se Use of substituted ureas or urethanes in order to improve the use properties of mineral and synthetic nonaqueous industrial liquids, in particular fuels or lubricants
WO2013131837A1 (en) 2012-03-07 2013-09-12 Basf Se Use of substituted ureas or urethanes in order to further improve the cold flow properties of mineral oils and crude oils
US9458401B2 (en) 2012-03-07 2016-10-04 Basf Se Use of substituted ureas or urethanes for improvement of the use properties of mineral and synthetic nonaqueous industrial fluids

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1000121B (en) * 1954-07-30 1957-01-03 Hoechst Ag Antifoam agent for drilling oils
BE550110A (en) * 1955-08-08

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB312774A (en) * 1928-04-30 1929-06-06 Standard Oil Company Of New Yo Petroleum distillates and method of treating same with respect to discoloration
US2263445A (en) * 1940-04-10 1941-11-18 Socony Vacuum Oil Co Inc Mineral oil compositions and improving agent therefor
US2343393A (en) * 1940-12-19 1944-03-07 Phillips Petroleum Co Lubricant
US2373049A (en) * 1943-02-05 1945-04-03 Du Pont Stabilization of organic substances
US2393934A (en) * 1943-11-17 1946-01-29 Socony Vacuum Oil Co Inc Mineral oil composition
US2396156A (en) * 1942-08-12 1946-03-05 Du Pont Stabilization of organic substances

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB312774A (en) * 1928-04-30 1929-06-06 Standard Oil Company Of New Yo Petroleum distillates and method of treating same with respect to discoloration
US2263445A (en) * 1940-04-10 1941-11-18 Socony Vacuum Oil Co Inc Mineral oil compositions and improving agent therefor
US2343393A (en) * 1940-12-19 1944-03-07 Phillips Petroleum Co Lubricant
US2396156A (en) * 1942-08-12 1946-03-05 Du Pont Stabilization of organic substances
US2373049A (en) * 1943-02-05 1945-04-03 Du Pont Stabilization of organic substances
US2393934A (en) * 1943-11-17 1946-01-29 Socony Vacuum Oil Co Inc Mineral oil composition

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2683081A (en) * 1950-12-09 1954-07-06 Ethyl Corp Stabilized organic compositions
US2683082A (en) * 1950-12-09 1954-07-06 Ethyl Corp Nu-aryl-nu'-(p-hydroxyphenyl) ureas as antioxidants for petroleum hydrocarbon fuels
US2813783A (en) * 1953-05-18 1957-11-19 Universal Oil Prod Co Stabilization of organic compounds
US2908647A (en) * 1954-01-28 1959-10-13 Tide Water Oil Company Pour point reduction
US2842433A (en) * 1956-11-19 1958-07-08 Texas Co Motor fuel composition
US2879230A (en) * 1956-11-19 1959-03-24 Texas Co Motor lubricating oil composition
US3092474A (en) * 1960-04-25 1963-06-04 Standard Oil Co Fuel oil composition
US3164553A (en) * 1960-12-16 1965-01-05 Union Carbide Corp Process of treating synthetic lubricating oils with urea
US3190763A (en) * 1960-12-17 1965-06-22 Hoechst Ag Process for the anti-static finishing of high molecular weight compounds
US3166387A (en) * 1961-07-17 1965-01-19 Standard Oil Co Ammonium carboxylate pour point depressants for fuel oil composition
US3278292A (en) * 1963-01-02 1966-10-11 Du Pont Herbicidal compositions and methods employing 3-phenyl-3-alkoxyureas
US3296136A (en) * 1963-11-13 1967-01-03 Sinclair Research Inc Lubricant compositions of improved oxidation resistance
FR2436814A1 (en) * 1977-06-20 1980-04-18 Shell Int Research COMBUSTIBLE AND LUBRICATING OIL COMPOSITIONS
US4401439A (en) * 1981-12-31 1983-08-30 Shell Oil Company Fuel and lubricant compositions for octane requirement reduction
US4435187A (en) 1981-12-31 1984-03-06 Shell Oil Company Fuel and lubricant compositions for octane requirement reduction
US4416669A (en) * 1982-02-22 1983-11-22 Shell Oil Company Fuel and lubricant compositions for octane requirement reduction
US5425789A (en) * 1986-12-22 1995-06-20 Exxon Chemical Patents Inc. Chemical compositions and their use as fuel additives
US5746783A (en) * 1994-03-30 1998-05-05 Martin Marietta Energy Systems, Inc. Low emissions diesel fuel
US5997593A (en) * 1998-12-22 1999-12-07 Ethyl Corporation Fuels with enhanced lubricity
US6725651B2 (en) * 2000-11-16 2004-04-27 Toyota Jidosha Kabushiki Kaisha Reducing agent for emission control system, reducing-agent supply device, and emission control system using the reducing agent
WO2013131800A1 (en) 2012-03-07 2013-09-12 Basf Se Use of substituted ureas or urethanes in order to improve the use properties of mineral and synthetic nonaqueous industrial liquids, in particular fuels or lubricants
WO2013131837A1 (en) 2012-03-07 2013-09-12 Basf Se Use of substituted ureas or urethanes in order to further improve the cold flow properties of mineral oils and crude oils
US9458401B2 (en) 2012-03-07 2016-10-04 Basf Se Use of substituted ureas or urethanes for improvement of the use properties of mineral and synthetic nonaqueous industrial fluids

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Publication number Publication date
BE506531A (en)
NL79072C (en)
GB710515A (en) 1954-06-16
DE894296C (en) 1953-10-22

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