US3567639A - Hydrocarbon-containing compositions - Google Patents
Hydrocarbon-containing compositions Download PDFInfo
- Publication number
- US3567639A US3567639A US636597A US3567639DA US3567639A US 3567639 A US3567639 A US 3567639A US 636597 A US636597 A US 636597A US 3567639D A US3567639D A US 3567639DA US 3567639 A US3567639 A US 3567639A
- Authority
- US
- United States
- Prior art keywords
- copolymer
- oil
- weight
- vinyl
- percent
- 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
- 239000000203 mixture Substances 0.000 title description 22
- 229930195733 hydrocarbon Natural products 0.000 title description 4
- 150000002430 hydrocarbons Chemical class 0.000 title description 4
- 239000004215 Carbon black (E152) Substances 0.000 title description 3
- 229920001577 copolymer Polymers 0.000 abstract description 33
- 239000010779 crude oil Substances 0.000 abstract description 17
- 229920001567 vinyl ester resin Polymers 0.000 abstract description 10
- 239000000295 fuel oil Substances 0.000 abstract description 9
- 239000003079 shale oil Substances 0.000 abstract description 9
- 229920002554 vinyl polymer Polymers 0.000 abstract description 6
- 230000000994 depressogenic effect Effects 0.000 abstract description 5
- 238000004821 distillation Methods 0.000 abstract description 4
- 229920006395 saturated elastomer Polymers 0.000 abstract description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical class C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 abstract 1
- 239000000446 fuel Substances 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 16
- 239000005977 Ethylene Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000003999 initiator Substances 0.000 description 10
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
- 239000001993 wax Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000002103 osmometry Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003350 kerosene Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- -1 saturated aliphatic monocarboxylic acid Chemical class 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- RLPIKSHMNSAWRK-UHFFFAOYSA-N ethenyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OC=C RLPIKSHMNSAWRK-UHFFFAOYSA-N 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
- LZWYWAIOTBEZFN-UHFFFAOYSA-N ethenyl hexanoate Chemical compound CCCCCC(=O)OC=C LZWYWAIOTBEZFN-UHFFFAOYSA-N 0.000 description 1
- QBDADGJLZNIRFQ-UHFFFAOYSA-N ethenyl octanoate Chemical compound CCCCCCCC(=O)OC=C QBDADGJLZNIRFQ-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IEDOGKKOPNRRKW-UHFFFAOYSA-N octadecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC IEDOGKKOPNRRKW-UHFFFAOYSA-N 0.000 description 1
- 239000003129 oil well Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000004291 sulphur dioxide Substances 0.000 description 1
- 235000010269 sulphur dioxide Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- C10L1/18—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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L31/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid; Compositions of derivatives of such polymers
- C08L31/02—Homopolymers or copolymers of esters of monocarboxylic acids
- C08L31/04—Homopolymers or copolymers of vinyl acetate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
-
- 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
- C10L1/16—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, 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
- C10L1/16—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, 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
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
-
- 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
- C10L1/20—Organic compounds containing halogen
- C10L1/206—Organic compounds containing halogen macromolecular compounds
- C10L1/207—Organic compounds containing halogen macromolecular compounds containing halogen with or without hydrogen
-
- 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
- C10L1/234—Macromolecular compounds
- C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
Definitions
- the pour point depressant is a copolymer of ethylene and a vinyl or C to C hydrocarbyl substituted vinyl ester of a C to C saturated aliphatic monocarboxylic acid, said copolymer having a number average molecular weight of about 4,000 to 60,000 and containing about 40 to 95 wt. percent ethylene.
- This invention relates to fuel compositions based on residua-containing fuels, and other base oils.
- pour point depressants Although various pour point depressants are known and have been used, they have been reasonably successful only with middle distillate fuels. It has been found difficult to obtain a potent pour point depressant for shale oils, residua or residua-containing fuels. We have now discovered certain polymers which are potent as pour point depressants in certain hydrocarbons, e.g, residua-containing fuels or crude oils.
- hydrocarbon-containing compositions comprise a major proportion by weight of a residua-containing fuel, shale oil or a crude oil and a minor proportion by weight of a copolymer of ethylene and vinyl (or hydrocarbyl substituted vinyl) ester of a carboxylic acid, said copolymer having a number average molecular weight of above 3,000 and preferably above 3,500.
- the residua-containing fuel is defined as a fuel comprising residua from the distillation of crude oil or shale oil or mixtures thereof.
- the residua-containing fuel (hereinafter referred to simply as the fuel) will contain from about 35% to 100% by weight of residua, and will usually have kinematic viscosities ranging from 10 to 3,500 cs. at 100 F.
- the viscosity of some particularly waxy fuels may be difficult to measure accurately at 100 F., and it is well known in the art that the viscosity of such fuels is measured by the viscosity at a higher temperature. The viscosity at 100 F.
- R.E.F.U.T.A.S. viscosity temperature chart The extrapolated kinematic viscosity will then fall in the desired range at 100 F.
- the R.E.F.U.T.A.S temperature viscosity chart was designed by C. I. Kelly, M.S.C. Tech., F.I.C., M. Inst., P.T., A.M.I.A.E. Copyright reserved in Great Britain and U.S.A. by Paird & Tatlock (London) Ltd., 14-17 Cross Street, Hatton Garden, London, E.C.1. Fuels having kinematic viscosities of between 15 and 1500 cs. at 100 F. are preferred, and also fuels wherein at least 60% by weight of the fuel boils above 500 F. at atmospheric pressure are particularly suitable.
- the fuels to which this invention applies include therefore, light, medium, heavy and bunker or furnace fuels, the viscosities ranging from about 152000 cs. at 100 F., but usually, however, the maximum viscosity will be about 900 cs. at 100 F. Examples of suitable fuels are described in PB Industrial and Marine Fuels of BS2689: 1957.
- the preferred ethylene comonomers are vinyl (or bydrocarbyl, e.g. C to C hydrocarbyl, substituted vinyl) esters of C to C carboxylic acids.
- the carboxylic acid is preferably aliphatic, and saturated and preferably monocarboxylic.
- the particularly preferred ester is vinyl acetate.
- the resulting polymer should contain from to 40 weight percent, preferabl 90 to 60 weight percent, of ethylene.
- One method of preparing the copolymers involves feeding the monomers into a tubular reactor which has been previously purged with nitrogen. A small amount of oxygen, usually 0.005 to 0.05 wt. percent based on the weight of ethylene is also introduced into the reactor. Alternatively a peroxide initiator, e.g. di-t-butyl peroxide, or a mixture of peroxide initiator and oxygen may be introduced into the reactor in place of oxygen alone. A solvent (e.g. benzene, water, saturated hydrocarbons, methanol) may also be employed in the reaction.
- a solvent e.g. benzene, water, saturated hydrocarbons, methanol
- the pressure is maintained between 60 and 2700 atmospheres (900 and 40,000 p.s.i.g.), preferably between and 2000 atmospheres (2,000 and 30,000 p.s.i.g.).
- the temperature should be maintained between 40 C. and 300 C., preferably between 70 C. and 250 C.
- Another method of preparing the copolymers is via a batch process.
- a solvent for the reactants the solvent being for example toluene or hexane.
- the preferred solvent however is benzene.
- the reaction initiator may be any peroxy compound, preferably di-tbutyl peroxide.
- the temperature of the polymerisation reaction is dependent upon the particular peroxide initiator employed and should be high enough for suflicient decomposition of the initiator to occur. This temperature will usually be between 40 C. and 300 C.
- the most suitable temperature is between 130 C. and C.
- the pressure should be between 60 and 1000 atmospheres (900 and 15,000 p.s.i.g.), and preferably being between 75 and 470 atmospheres (1100 and 7000 p.s.i.g.).
- the autoclave or similar equipment containing the solvent, initiator and vinyl or hydrocarbyl substituted vinyl ester is purged with nitrogen and then with ethylene before charging with a sufficient amount of ethylene to yield the desired pressure when heated to the reaction tempertaure. During the polymerization addition ethylene is added to maintain the pressure at the desired level. Further amounts of initiator and/ or solvent, and/ or vinyl and hydrocarbyl substituted vinyl ester may also be added during the reaction. On completion of the reaction free solvent and unreacted monomers are removed by stripping or some other suitable process yielding the desired polymer.
- the copolymers useful in the invention preferably have a number average molecular weight from 3,000 to 60,000 as measured by Vapour Phase Osmometry (using a Mechrolab Vapour Phase Osmometer model 301A) and/or Membrane Osmometry (using a Mechrolab 1 Membrane Osmometer model 501).
- the number average Heehrolab Inc. 1062 Linda Vista Avenue, Mountain View, Calif.
- the copolymer can also be applied down oil wells to crude oil to inhibit the formation of paraffin deposits, or to dissolve existing deposits on the sides of the well casing.
- the copolymer can also be added to crude oils or residua above ground to facilitate their movement through pipe lines.
- the copolymer can be added to any North African crude, to lower the pour points so that they can be more readily pumped.
- copolymer concentrates in suitable hydrocarbon blend stocks.
- suitable solvents are those containing a high proportion of aromatic hydrocarbons, e.g. toluene, xylene, kerosene extract, this extract being the highly aromatic fraction separated from a crude kerosene by a liquid sulphur dioxide extraction process.
- suitable solvents are slack waxes, which are the waxes obtained without purification or refining from lubricating oil dewaxing processes. Such suitable slack waxes will usually have melting points between 20 C. and 62 C. and oil contents of to 50 wt. percent.
- a suitable composition of such copolymer/solvent blends is 5 to 50% by weight of copolymer, and 95 to 50% by weight of solvent.
- particularly suitable blends have been found to be a blend of to 30 e.g. by Weight of an ethylene/vinyl acetate copolymer and 90 to 70% e.g. 75% of a slack wax or a kerosene extract.
- These compositions can be readily blended into fuels to the required concentrations, e.g. up to 1% by weight, at temperatures of about 40 C. and above.
- copolymers may also be used in the fuels, crude oils, etc. in conjunction with other additives commonly used in fuels, e.g. rust-inhibitors, demulsifying agents, corrosion inhibitors, anti-oxidants or dispersants, or other flow improvers or pour depressants.
- additives commonly used in fuels, e.g. rust-inhibitors, demulsifying agents, corrosion inhibitors, anti-oxidants or dispersants, or other flow improvers or pour depressants.
- EXAMPLE 1 In this example, two copolymers were used, and added in different concentrations to two different fuels.
- Copolymer A was a random copolymer of ethylene (67 weight percent and vinyl acetate (33 weight percent) having a number average molecular weight of 13,000 as measured by Vapour Phase Osmometry using chloroform as solvent at 37 C.
- Copolymer B was a random copolymer of ethylene (82 weight percent) and vinyl acetate (18 weight percent) having a number average molecular weight of 12,000 as measured by Vapour Phase Osmometry using benzene as solvent at 37 C. Both A and B were separately blended with a slack wax so that the blends contained 25% by Weight of A and 25% by weight of B respectively. The slack wax had a melting point of 40 C. and contained 29 wt. percent of oil.
- the copolymer/slack wax blends were separately blended into two different residual-containing fuel oils C and D having the following characteristics.
- Fuel oil C contained 32% by weight of distillate fraction boiling between 350 and 680 F., and 68% by weight of residuum with a boiling point of 680+ F., and it had a kinematic viscosity of 43.2 cs. at 100 F.
- Fuel oil D had an initial boiling point Copolymer eoneen- Upper pour tration, Flow point, F. point, F.
- the polymers prepared in Examples 2 and 3 have the following properties:
- POLYMER PROPERTIES 1 Number average molecular Weight measured in toluene solution at 37 C. using a Mechrolab Vapour Phase Osmometer, Model 301A.
- composition according to claim 1 wherein said oil is crude oil and said ester is a vinyl ester.
- composition according to claim 2 wherein said molecular weight is in the range of 4,000 to 20,000.
- composition according to claim 3 wherein said ester is vinyl acetate.
- composition according to claim 1 wherein said oil is fuel oil having at least 60 wt. percent boiling above 500 F. at atmospheric pressure and having a viscosity between 15 and 3,500 cs. at F., and said ester is vinyl ester.
- composition according to claim 5 wherein said molecular weight is in the range of 4,000 to 20,000.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24368/66A GB1147904A (en) | 1966-06-01 | 1966-06-01 | Fuel compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3567639A true US3567639A (en) | 1971-03-02 |
Family
ID=10210617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US636597A Expired - Lifetime US3567639A (en) | 1966-06-01 | 1967-05-08 | Hydrocarbon-containing compositions |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3567639A (de) |
| BE (1) | BE699350A (de) |
| DE (1) | DE1645873A1 (de) |
| ES (1) | ES341195A1 (de) |
| GB (1) | GB1147904A (de) |
| NL (2) | NL6707475A (de) |
| NO (1) | NO118198B (de) |
| SE (1) | SE320542B (de) |
Cited By (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3682249A (en) * | 1971-01-08 | 1972-08-08 | Paul W Fischer | Method for inhibiting the deposition of wax from wax-containing soluble oils and micellar dispersions and soluble oil and micellar compositions inhibited thereby |
| US3792984A (en) * | 1970-06-25 | 1974-02-19 | Texaco Inc | Fuel oil blending to improve pour reduction |
| US3841850A (en) * | 1967-11-30 | 1974-10-15 | Exxon Research Engineering Co | Hydrocarbon oil containing ethylene copolymer pour depressant |
| US3850587A (en) * | 1973-11-29 | 1974-11-26 | Chevron Res | Low-temperature flow improves in fuels |
| US3862825A (en) * | 1969-12-02 | 1975-01-28 | William M Sweeney | Low pour point gas fuel from waxy crudes |
| US3880613A (en) * | 1972-02-07 | 1975-04-29 | Alexis A Oswald | Higher alkyl trimethyl ammonium salt liquid hydrocarbon compositions |
| USB407812I5 (de) * | 1969-05-09 | 1976-03-23 | ||
| US3947368A (en) * | 1971-02-25 | 1976-03-30 | Texaco Inc. | Lubricating oil compositions |
| US3961916A (en) * | 1972-02-08 | 1976-06-08 | Exxon Research And Engineering Company | Middle distillate compositions with improved filterability and process therefor |
| US4115343A (en) * | 1975-06-06 | 1978-09-19 | Rhone-Poulenc Industries | Homogeneous dispersions of diorganopolysiloxane compositions in mineral oils |
| US4149984A (en) * | 1977-09-08 | 1979-04-17 | Rohm Gmbh | Lubricating oil additives |
| US4156434A (en) * | 1972-06-21 | 1979-05-29 | Texaco Inc. | Low pour point fuel compositions |
| US4417038A (en) * | 1980-12-12 | 1983-11-22 | Basf Aktiengesellschaft | Ethylene-alkyne copolymers, their preparation and their use as additives to petroleum distillates |
| US4564460A (en) * | 1982-08-09 | 1986-01-14 | The Lubrizol Corporation | Hydrocarbyl-substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
| US4575526A (en) * | 1982-08-09 | 1986-03-11 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same |
| US4613342A (en) * | 1982-08-09 | 1986-09-23 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
| US4623684A (en) | 1982-08-09 | 1986-11-18 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
| US4906682A (en) * | 1986-04-19 | 1990-03-06 | Rohm Gmbh | Ethylene-vinyl ester copolymer emulsions |
| US4932980A (en) * | 1987-07-29 | 1990-06-12 | Rohm Gmbh | Polymeric fluidizer for middle distillates |
| US5078917A (en) * | 1989-11-01 | 1992-01-07 | Functional Products Incorporated | White oil pour point depressants |
| WO1992004428A1 (en) * | 1990-08-31 | 1992-03-19 | Olin Corporation | Fire resistant hydraulic fluid composition |
| US5141663A (en) * | 1990-08-31 | 1992-08-25 | Olin Corporation | Fire resistant hydraulic fluid composition |
| US6010989A (en) * | 1997-09-08 | 2000-01-04 | Clariant Gmbh | Additive for improving the flow properties of mineral oils and mineral oil distillates |
| US6099601A (en) * | 1996-02-29 | 2000-08-08 | Basf Aktiengesellschaft | Ethylene-vinyl formate copolymers, process for their preparation, their use as flow improvers, and fuel and propellant compositions comprising them |
| US6495495B1 (en) | 1999-08-20 | 2002-12-17 | The Lubrizol Corporation | Filterability improver |
| US20080073247A1 (en) * | 2005-07-18 | 2008-03-27 | Oiltreid Limited Liabilities Company | Heavy Oil Fuel |
| WO2012170242A1 (en) | 2011-06-10 | 2012-12-13 | Dow Global Technologies Llc | Method t0 make an aqueous pour point depressant dispersion composition |
| WO2016137922A1 (en) | 2015-02-27 | 2016-09-01 | Dow Global Technologies Llc | Hydrocarbon solvent stable aqueous pour point depressant dispersion composition |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2102469C2 (de) * | 1971-01-20 | 1989-06-29 | Basf Ag, 6700 Ludwigshafen | Verwendung von Äthylencopolymerisaten als Zusatz zu Erdöl und Erdölfraktionen |
| DE3031344A1 (de) * | 1980-08-20 | 1982-04-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von polymerisat-sekundaerdispersionen und die verwendung der sekundaerdispersionen als stockpunktserniedriger fuer mineraloele |
| DE3445811A1 (de) * | 1984-12-15 | 1986-06-19 | Ruhrchemie Ag, 4200 Oberhausen | Verwendung von ethylencopolymerisaten als rohoeladditive |
| AR100387A1 (es) | 2014-02-18 | 2016-10-05 | Basf Se | Copolímeros que comprenden etileno, ésteres de vinilo y ésteres de ácido (met)acrílico, sus formulaciones y usos como depresor del punto de fluidez, inhibidor de cera y potenciador de flujo para petróleos crudos |
| US20210017341A1 (en) | 2018-03-26 | 2021-01-21 | Basf Se | Hyperbranched polyethers and their use, especially as pour point depressant and wax inhibitors |
-
0
- NL NL134313D patent/NL134313C/xx active
-
1966
- 1966-06-01 GB GB24368/66A patent/GB1147904A/en not_active Expired
-
1967
- 1967-05-08 US US636597A patent/US3567639A/en not_active Expired - Lifetime
- 1967-05-29 DE DE19671645873 patent/DE1645873A1/de active Pending
- 1967-05-30 NO NO168373A patent/NO118198B/no unknown
- 1967-05-30 NL NL6707475A patent/NL6707475A/xx unknown
- 1967-05-31 SE SE7649/67*A patent/SE320542B/xx unknown
- 1967-05-31 ES ES341195A patent/ES341195A1/es not_active Expired
- 1967-06-01 BE BE699350D patent/BE699350A/xx not_active IP Right Cessation
Cited By (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3841850A (en) * | 1967-11-30 | 1974-10-15 | Exxon Research Engineering Co | Hydrocarbon oil containing ethylene copolymer pour depressant |
| US4010006A (en) * | 1969-05-09 | 1977-03-01 | Exxon Research And Engineering Company | Flow improvers |
| USB407812I5 (de) * | 1969-05-09 | 1976-03-23 | ||
| US3862825A (en) * | 1969-12-02 | 1975-01-28 | William M Sweeney | Low pour point gas fuel from waxy crudes |
| US3792984A (en) * | 1970-06-25 | 1974-02-19 | Texaco Inc | Fuel oil blending to improve pour reduction |
| US3682249A (en) * | 1971-01-08 | 1972-08-08 | Paul W Fischer | Method for inhibiting the deposition of wax from wax-containing soluble oils and micellar dispersions and soluble oil and micellar compositions inhibited thereby |
| US3947368A (en) * | 1971-02-25 | 1976-03-30 | Texaco Inc. | Lubricating oil compositions |
| US3880613A (en) * | 1972-02-07 | 1975-04-29 | Alexis A Oswald | Higher alkyl trimethyl ammonium salt liquid hydrocarbon compositions |
| US3961916A (en) * | 1972-02-08 | 1976-06-08 | Exxon Research And Engineering Company | Middle distillate compositions with improved filterability and process therefor |
| US4156434A (en) * | 1972-06-21 | 1979-05-29 | Texaco Inc. | Low pour point fuel compositions |
| US3850587A (en) * | 1973-11-29 | 1974-11-26 | Chevron Res | Low-temperature flow improves in fuels |
| US4115343A (en) * | 1975-06-06 | 1978-09-19 | Rhone-Poulenc Industries | Homogeneous dispersions of diorganopolysiloxane compositions in mineral oils |
| US4149984A (en) * | 1977-09-08 | 1979-04-17 | Rohm Gmbh | Lubricating oil additives |
| US4417038A (en) * | 1980-12-12 | 1983-11-22 | Basf Aktiengesellschaft | Ethylene-alkyne copolymers, their preparation and their use as additives to petroleum distillates |
| US4564460A (en) * | 1982-08-09 | 1986-01-14 | The Lubrizol Corporation | Hydrocarbyl-substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
| US4613342A (en) * | 1982-08-09 | 1986-09-23 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
| US4623684A (en) | 1982-08-09 | 1986-11-18 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
| US4575526A (en) * | 1982-08-09 | 1986-03-11 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same |
| US4906682A (en) * | 1986-04-19 | 1990-03-06 | Rohm Gmbh | Ethylene-vinyl ester copolymer emulsions |
| US4932980A (en) * | 1987-07-29 | 1990-06-12 | Rohm Gmbh | Polymeric fluidizer for middle distillates |
| US5078917A (en) * | 1989-11-01 | 1992-01-07 | Functional Products Incorporated | White oil pour point depressants |
| WO1992004428A1 (en) * | 1990-08-31 | 1992-03-19 | Olin Corporation | Fire resistant hydraulic fluid composition |
| US5141663A (en) * | 1990-08-31 | 1992-08-25 | Olin Corporation | Fire resistant hydraulic fluid composition |
| US6235069B1 (en) * | 1996-02-29 | 2001-05-22 | Basf Aktiengesellschaft | Ethylene-vinyl formate copolymers, process for their preparation, their use as flow improvers, and fuel and propellant compositions comprising them |
| US6099601A (en) * | 1996-02-29 | 2000-08-08 | Basf Aktiengesellschaft | Ethylene-vinyl formate copolymers, process for their preparation, their use as flow improvers, and fuel and propellant compositions comprising them |
| US6010989A (en) * | 1997-09-08 | 2000-01-04 | Clariant Gmbh | Additive for improving the flow properties of mineral oils and mineral oil distillates |
| US6495495B1 (en) | 1999-08-20 | 2002-12-17 | The Lubrizol Corporation | Filterability improver |
| US20080073247A1 (en) * | 2005-07-18 | 2008-03-27 | Oiltreid Limited Liabilities Company | Heavy Oil Fuel |
| US7708876B2 (en) | 2005-07-18 | 2010-05-04 | Oiltreid Limited Liabilities Company | Heavy fuel oil |
| WO2012170242A1 (en) | 2011-06-10 | 2012-12-13 | Dow Global Technologies Llc | Method t0 make an aqueous pour point depressant dispersion composition |
| WO2016137922A1 (en) | 2015-02-27 | 2016-09-01 | Dow Global Technologies Llc | Hydrocarbon solvent stable aqueous pour point depressant dispersion composition |
Also Published As
| Publication number | Publication date |
|---|---|
| ES341195A1 (es) | 1968-06-16 |
| NL6707475A (de) | 1967-12-04 |
| BE699350A (de) | 1967-12-01 |
| GB1147904A (en) | 1969-04-10 |
| SE320542B (de) | 1970-02-09 |
| DE1645873A1 (de) | 1970-07-09 |
| NO118198B (de) | 1969-11-24 |
| NL134313C (de) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3567639A (en) | Hydrocarbon-containing compositions | |
| US4985048A (en) | Polymer mixtures for improving the low-temperature flow properties of mineral oil distillates | |
| US3961916A (en) | Middle distillate compositions with improved filterability and process therefor | |
| US3620696A (en) | Fuel oil with improved flow properties | |
| US4365973A (en) | Middle distillate fuel additive | |
| JP2925078B2 (ja) | エチレンのターポリマー、その製法および鉱油留分の添加物としてのそれの用途 | |
| JP4299389B2 (ja) | エチレンコポリマーの製造方法、及びこれを鉱油及び鉱油蒸留物の添加剤として使用する方法 | |
| US3642459A (en) | Copolymers of ethylene with unsaturated esters and oil compositions containing said copolymers | |
| ES2218748T3 (es) | Aceites combustibles que contienen copolimeros de etileno con un contenido de grupos hidroxilo. | |
| US3726653A (en) | Polymeric pour point depressant for residual fuels | |
| KR940006450B1 (ko) | 에틸렌의 삼원공중합체, 그의 제조방법 및 광유 증류물용 첨가제로서의 그의 용도 | |
| US3660057A (en) | Increasing low temperature flowability of middle distillate fuel | |
| US5039432A (en) | Copolymers of (meth) acrylic acid esters as flow improvers in oils | |
| DE19620119C1 (de) | Terpolymerisate des Ethylens, ihre Herstellung und ihre Verwendung als Additive für Mineralöldestillate | |
| US3841850A (en) | Hydrocarbon oil containing ethylene copolymer pour depressant | |
| DE4042206A1 (de) | Terpolymerisate des ethylens, ihre herstellung und ihre verwendung als additive fuer mineraloeldestillate | |
| US3640691A (en) | Enhancing low-temperature flow properties of fuel oil | |
| US3467597A (en) | Grafted terpolymers,their process of production,and use as additives for lubricants and fuels | |
| US4178950A (en) | Residual fuel compositions with low pour points | |
| US4862908A (en) | Mineral oils and mineral oil distillates having improved flowability and method for producing same | |
| US4160459A (en) | Low pour crude oil compositions | |
| US3454379A (en) | Hydrocarbon oil composition having improved low temperature pumpability | |
| US3847561A (en) | Petroleum middle distillate fuel with improved low temperature flowability | |
| JPH072955A (ja) | グラフト共重合体、その製法および原油、残油および中間留出物の為の流動点降下剤および流動性改善剤としてのそれの用途 | |
| US3832150A (en) | Fuel oil with improved low temperature flowability |