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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/16—Hydrocarbons
  • C10L1/1616—Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/16—Hydrocarbons
  • C10L1/1625—Hydrocarbons macromolecular compounds
  • C10L1/1633—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds
  • C10L1/1641—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds from compounds containing aliphatic monomers
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/16—Hydrocarbons
  • C10L1/1625—Hydrocarbons macromolecular compounds
  • C10L1/1633—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds
  • C10L1/165—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds from compounds containing aromatic monomers
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • C10L1/1955—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by an alcohol, ether, aldehyde, ketonic, ketal, acetal radical
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
  • C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
  • C10L1/1966—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof poly-carboxylic
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/192—Macromolecular compounds
  • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
  • C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/234—Macromolecular compounds
  • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
  • C10L1/2368—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing heterocyclic compounds containing nitrogen in the ring

Definitions

• Small size crystals are desirable so that the precipitated wax will not clog the fine mesh screens that are provided in fuel transportation, storage, and dispensing equipment. It is thus desirable to obtain not only fuel oils with low pour points but also oils that will form small wax crystals so that the clogging of filters will not impair the flow of the fuel at low operating temperatures.
• a paraffin hydrocarbon fraction preferably a naturally occurring fraction, that is substantially free of normal paraffm hydrocarbons, i.e., containing no more than about 5 wt. preferably 3 wt. or less, and most preferably no more than about one weight percent, of normal paraffin hydrocarbons, and that has a number average molecular weight of from about 600 to about 3,000, when'added to a middle distillate petroleum fuel oil in a concentration of about 0.01 to about 3 wt. preferably about 0.1 to 2 wt.
• the active components of the normal-paraffin-free fraction can be either isoparafiins or cycloparaffins or mixtures of both types.
• the distillate fuel oil can comprise straightrunor virgin gas oil or cracked gas oil or a blend in any proportion of straight run and thermally and/or catalytically cracked distillates.
• the most common petroleum middle distillate fuels are kerosine, diesel fuels, jet fuels and heating oils. Since jet fuels are normally refined to very low pour points there will be generally no need to apply the presentinvention to such fuels.
• the low temperature flow problem is most usually encountered with diesel fuels and with heating oils.
• a representative heating oil specification calls for a 10 percent distillation point no higher than about 440 F., a 50 percent point no higher than about 520 F., and a percentpoint of'at'least 540 F. and no higher than about 640 to 650 F., although some specifications set the 90 percent point as high as 675 F.
• Heating oils are preferably made of a blend of virgin distillate, e.g.,
• a representative specification for a diesel fuel includes a minimum flash point of F. and a 90 percent distillation point between 540 and 640 F. (See ASTM Designations D-396 and D-975) v
• the fractions of essentially saturated hydrocarbons that are used in accordance with the present invention as flow improvers and pour point depressants are generally amorphous solid materials having melting points within the range of about 80 to 140F. and having number average molecular weights within the range of about 600 to about 3,000. This molecular weight range is above the highest molecular weight of any hydrocarbons that are naturally present in the fuel oil.
• An amorphous hydrocarbon fraction that is useful as a fuel oil flow improver in accordance with this invention can be obtained by deasphalting a residual petroleum fraction and then adding a solvent such as propane, lowering thetemperature of the solvent-diluted residuum, and recovering the desired solid or semi-solid amorphous product by precipitation, followed by filtration.
• The-residual oil fractionsfrom which the desired amorphous hydrocarbons are obtained will have viscosities of at least 125 SUS at 210 F. Most of these residual oils are commonly referred to as bright stocks.
• products obtained by this procedure will be naturally low in normal paraffin hydrocarbons and can be used in the present invention without further treatment.
• a high molecular weight fraction can be obtained which has only a trace of normal paraftins, about 5 percent of isoparaffins, about 73 percent of cycloparafiins and about 22 percent of aromatic hydrocarbons.
• Removal of normal paraffins from an amorphous hydrocarbon mixture can be eff fected by complexing with urea, as will be illustrated hereinafter in one of the examples. Solvent extraction procedures can also be used, but in many instances they are not as effective as complexing techniques.
• amorphous hydrocarbon mixture can be dissolved in heptane at its boiling point and then when the solution is cooled to room temperature the normal paraftins will be predominantly precipitated and the resultant supernatant solution will give a mixture containing some normal paraffins but predominating in cycloparaffins a'nd isoparaffins.
• Vacuum distillation can also be used for the removal of normal paraffin hydrocarbons from a high molecular weight paraffinic fraction, but such a procedure requires a very high vacuum, i.e., less than 5 mm'Hg, absolute. pressure, preferably a pressure below 3 mm Hg, absolute, e.g., 2 mm or micronsJf thepressure used is 5 mm or higher, the necessary temperature for the distillation is high enough to cause cracking of the constituents, which is undesirable.
• the action of the high molecular weight hydrocarbon fraction in improving fuel oil low temperature flow properties can be enhanced by employing in conjunction with the added hydrocarbon fraction a small amount e.g., 0.001 to 1 wt. of a wax-modifying pour-point depressant of the type comprising a copolymer of ethylene with another ethylenically unsaturated monomer, wherein the ethylene forms a backbone along which there are randomly distributed side chains consisting of hydrocarbon groups or oxy-substituted hydrocarbon groups of up to 16 carbon atoms.
• a wax-modifying pour-point depressant of the type comprising a copolymer of ethylene with another ethylenically unsaturated monomer, wherein the ethylene forms a backbone along which there are randomly distributed side chains consisting of hydrocarbon groups or oxy-substituted hydrocarbon groups of up to 16 carbon atoms.
• a distillate fuel oil having a distillation range of about 320 to 654 F., 0.2 w
• the pour point depressants of the type comprising a copolymer of ethylene and at least one second unsaturated monomer can include as the second unsaturated monomer another monoolefin, e.g., a C to C alpha-monoolefin or an unsaturated ester, as for example vinyl acetate, vinyl butyrate, vinyl propionate, lauryl methacrylate, ethyl acrylate or the like. (See Canadian Patents 676,875 and 695,699).
• Other second monomers include N-vinyl pyrrolidone.
• the second monomer can also be a mixture of an unsaturated monoester or diester and a branched or straight chain alpha monoolefin.
• Copolymers can also be used, as for example mixtures of a copolymer of ethylene and vinyl acetate with an alkylated polystyrene or acylated polystyrene (see U.S. Pat. No. 3,037,850 and 3,069,245).
• the copolymer pour depressants will consist essentially of about 3 to 40, and preferably 3 to 20, molar proportions of ethylene per molar proportion of the ethylenically unsaturated monomer, which latter monomer can be a single monomer or a mixture of such monomers in any proportion, said polymer being oil-soluble and having a number average molecular weight in the range of about 1,000 to 50,000, preferably about 1,500 to about 5,000 molecular weight.
• Molecular weights can be measured by cryoscopic methods or by vapor-phase osmometry, for example by using a Mechrolab Vapor Phase Osmometer Model 310A.
• ethylene copolymers wherein the number of methyl terminating side branches per 100 methylene groups of the copolymer does not exceed about 6.
• Such copolymers are prepared by copolymerizing the monomers in an inert solvent such as benzene or hexane at a temperature of about 70 to 130 C. using a free radical catalyst with a halflife'ofless than 1 hour at 130 C., e.g., di-lauroyl peroxide.
• the unsaturated monomers, copolymerizable with ethylene include unsaturated acids, acid anhydrides, and mono and diesters of the general formula:
• R is .hydrogen or methyl; R is a -OOCR or COOR, group wherein R is hydrogen or a C to C preferably a C to C straight or branched chain alkyl group and R is hydrogen or COOR
• the monomer, when R to R are hydrogen and R is -OOCR includes vinyl alcohol esters of C to C monocarboxylic acids. Examples of such esters include vinyl acetate, vinyl isobutyrate, vinyl laurate, vinyl myristate, vinyl palmitate, etc. When R is -COOR., such esters include iso-octyl acrylate, methyl acrylate, methyl methacrylate,
• lauryl acrylate isobutyl methacrylate, palmityl alcohol ester of alpha-methyl-acrylic acid, mixed C isomeric alcohol esters of methacrylic acid, etc.
• monomers wherein R is hydrogen and R and R are OOCR., groups include mono iso-octyl alcohol fumarate, di-isopropyl maleate; di-lauryl fumarate; ethyl methyl fumarate, fumaric acid, maleic acid, etc;
• Other unsaturated monomers copolymerizable with ethylene to prepare pour point depressants include C to C branched chain or straight-chain alpha monoolefins, as for example propylene, n-octane-l, 2-ethyl decene-l, n-decene-l, etc.
• a copolymer of 3 to 40 moles of ethylene with one mole of a mixture of 30 to 99 mole percent of unsaturated ester and 70 to 1 mole percent of olefin could be used.
• copolymers that are formed are random copolymers consisting primarily of I an ethylene polymer backbone along which are distributed side chains of hydrocarbon or oxy-substituted hydrocarbon.
• pour depressants that can be used include the acylated polystyrenes and the alkylated polystyrenes. (See US. Pat. No. 3,069,245)
• EXAMPLE 1 An amorphous hydrocarbon fraction (mp. 11 1 F.) obtained by propane precipitation from the deasphalted residuum of a Texas coastal crude oil was found by mass spectrographic analysis, and by gas chromatography, to contain 5 wt. of isoparaffins, 22 wt. of aromatic hydrocarbons, 73 percent of cycloparaffins, and no more than a trace of normal paraffin hydrocarbons. The number average molecular weight of this material was about 775 as determined by osmometry.
• Oil E Boiling range 368654 F.; 80 percent Cat Cycle Stock 20 percent Virgin Naphtha.
• PFT test programmed fluidity test
• a 40 milliliter sample of the oil to be tested is placed in an hourglass-shaped device, having upper and lower sections connected by an opening between the two sections having a diameter of about 2.25 mm, the opening being initially closed by a thin aluminum disc.
• the tester containing the oil is placed in a cold box and the oil is cooled from a point 10 F. above the cloud point to a temperature ofl F., at the rate of 4 F./hr.
• the tester is inverted and the oil is allowed to settle for one minute.
• the aluminum disc is punctured so that the oil fiows from the upper chamber through the aforesaid opening into the lower chamber.
• the oil has passed the test when at least 85 volume percent of the oil flows from the upper chamber to the lower chamber in a time of 3 minutes or less.
• the other low temperature flow test is conducted as follows: A 200 milliliter sample of the oil is cooled at a controlled rate of 4 F. per hour until a temperature of either 10" F. or of 20 F. is reached, these being the temperatures at which the flow test is conducted. The oil is then permitted to flow by gravity at the test temperature through a 20 mesh screen of9 millimeters diameter for 25 seconds. The volume percentage of oil that has flowed through the screen at the end of this time is then measured. If more than 85 volume percent of the oil has gone through the screen at the end of the 25 seconds, the oil is considered to have passed the test.
• compositions of the various oil blends tested, their measured ASTM pour points, and the test results obtained in the low temperature flow tests are given in Table I, which follows.
• the weight percentages of the added materials are based on the total composition in each instance. It will be seen from the data that the added normaI-paraffin-free hydrocarbon fraction was quite effective in improving the low temperature properties of each of the heating oils.
• the combined filtrate and washings were transferred to a separatory funnel and extracted seven times with 100 milliliter portions of water in order to remove any dissolved urea that might be present.
• the hydrocarbon layer in the separatory funnel was then transferred to a distillation flask and all of the solvents were removed by distillation.
• the distillation residue which amounted to 16 grams, i.e., percentof the original solid hydrocarbon mixture, had a pasty appearance.
• the product is hereinafter referred to as non-normal-parafiin hydrocarbon mixture A, or more simply hydrocarbon mixture A.
• the product had a number average molecular weight of I 817 as determined by osmometry and a melting point of 1 13 F.
• EXAMPLE 3 A portion of the original mixture of solid hydrocarbons of I example 2, containing 20 wt. of normal paraffins, was subjected to vacuum distillation at 2 mm Hg absolute pressure to a final still temperature of 650 F., the final vapor temperature being 583 R, which is equivalent to 965 F. at atmospheric pressure. The distillation took about 25 percent of the material, leaving about 75 percent bottoms. The bottoms product, when checked by gas chromatography, showed that no normal paraffins were present. When 0.4 wt. of the bottoms product was blended into fuel oil E, the blend gave 97 percent recovery at -10 F. through a 30 mesh screen and 100 percent recovery at 0 F. through a 40 mesh screen using the filterability test described in example 2.
• EXAMPLE 4 A quantity of the solid hydrocarbon fraction described in example 1 was subjected to vacuum distillation in a molecular still at pressures in the range of from 5 to 20 microns absolute, and at temperatures ranging from 191 to 342 C. Various fractionsobtained in this vacuum distillation were tested for their effect in improving the flow properties of a fuel oil by blending 0.75 wt. of each of several of the fractions in separate portions of fuel oil E described above. These blends were then subjected to the PFT test at 10 F. Also tested was a blend prepared by adding, to fuel oil E, 0.75 wt. ofa solid hydrocarbon mixture of 75 F.
• the effect of the aromatic hydrocarbons present in the solid hydrocarbon fractions used in demonstrating this invention was found to be negligible. This is shown by the following test.
• the solid hydrocarbon fraction used in example I was separated into an aromatic hydrocarbon fraction (22 percent) and a non-aromatic hydrocarbon fraction (78 percent) by a silica gel separation technique wherein the the original hydrocarbon mixture was dissolved in normal heptane and the solution was percolated through a column of silica gel, the
• J t I I .Wl-lAT IS CLAIMED IS ILA wax-containing petroleum distillate fuel having a boiling range within the limits of about 250 and 700? F. which has been improved with respect to its low temperature flow properties by adding thereto from about 0.01 to about 3 wt. of

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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)

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Cited By (12)

Citations (3)

• 1969
  • 1969-03-17 US US807953A patent/US3660058A/en not_active Expired - Lifetime
• 1970
  • 1970-03-02 CA CA076229A patent/CA917920A/en not_active Expired
  • 1970-03-03 GB GB1301326D patent/GB1301326A/en not_active Expired

Patent Citations (3)

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