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  • C10L1/00—Liquid carbonaceous fuels
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  • 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
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/192—Macromolecular compounds
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  • 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
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  • C10L1/00—Liquid carbonaceous fuels
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  • 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
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  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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  • 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
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  • 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
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  • 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
  • C10L1/2364—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups
• • C—CHEMISTRY; METALLURGY
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/234—Macromolecular compounds
  • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
  • C10L1/2366—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amine groups
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  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
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  • 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
• • C—CHEMISTRY; METALLURGY
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/2666—Organic compounds containing phosphorus macromolecular compounds
  • C10L1/2675—Organic compounds containing phosphorus macromolecular compounds obtained by reactions involving only carbon to carbon unsaturated bonds; derivatives thereof
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
  • Y10T137/00—Fluid handling
  • Y10T137/0318—Processes
  • Y10T137/0391—Affecting flow by the addition of material or energy

Definitions

• ABSTRACT A method of transporting waxy crudes through conduits at reduced friction and preventing wax separation or precipitation so as to inhibit plugging and flow restriction and improve the pour point'properties of the crude by adding to such waxy crudes a small amount of a polymeric material containing aliphatic hydrocarbon side chains of at least 14 carbon atoms.
• This invention relates to decreasing friction loss in flowing waxy crudes through conduits, generally over great distances but also over short distances such as in well fracturing processes and also to improving the pour point of waxy crudes. More particularly, the invention is directed to crude oil compositions comprising a waxy crude oil and fractions thereof and polymers having aliphatic hydrocarbon side chains with at least 14 carbon atoms, so as to reduce the pour point, prevent wax separation and reduce its friction loss due to flow through pipelines over great distances and short distances.
• pour point is a criterion of the lowest permissible temperature during storage or transport or during a possible interruption of transport.
• the 'yield stress gives an impression of the shear stresses which may be expected if a stagnant oil is to be set in motion again.
• the viscosity is particularly related to the resistance which the oil experiences during pumping.
• the invention therefore relates to a crude oil composition
• a crude oil composition comprising a waxy crude oil and polymers containing aliphatic hydrocarbon side chains with at least 14 carbon atoms, which polymers may be taken to have been obtained by polymerization of olefinically unsaturated compounds.
• long hydrocarbon chains and long hydrocarbon side chains will be used hereinafter to designate aliphatic hydrocarbon chains and aliphatic hydrocarbon side chains with at least 14 carbon atoms, respectively.
• the polymers according to the invention are capable of improving the flow properties of waxycrude oils, the afore-mentioned problems, which arise during production, storage, transport and refining of waxy crude oils owing to insufficient flow, can be effectively solved by incorporating these polymers into the waxy crude oil.
• waxy crude oil When waxy crude oil is shipped, it is customary to keep the cargo during transport at an elevated temperature, for example by means of steam coils.
• the invention offers the possibility of shipping waxycrude oils without heating during the voyage being necessary. This means not only an appreciable saving for existing tankers, where the available energycan then be fully utilized to propel the ship, but particularly when constructing new tankers, where the installation of costly equipment for heating the cargo can be omitted. In spite of the cold shipment a low tum-out loss can be maintained. Shipment of unheated waxy crude oil containing polymers according to the invention permits the use of higher discharge pumping rates.
• the invention not only presents the possibility of reducing the required pump power, which'will reduce the cost of pumping, but by applying the invention the transport capacity of the line may be increased at the same pump power. Waxy crude oils which up to now were regarded as unacceptable for pipeline transport because of their flow properties, can now be rendered suitable for this,
• the present method has the advantage that, since only very residue.
• the polymers' should contain long hydrocarbon side chains with at least 14 carbon atoms.
• polymers are chosen with long hydrocarbon side chains, wherein the number of carbon atoms is at least 16 and at most 30, in particular at least 18 and at most
• the polymers that may be employed as pour point depressants according to the invention consist of a main chain built up of carbon atoms, which main chain carries long hydrocarbon side chains. These long hydrocarbon side chains may be attached either directly or indirectly to the main chain.
• the long hydrocarbon side chain is attached indirectly to the main chain, one or more other atoms such as carbon, oxygen, sulphur,-nitrogen or phosphorus atoms are present between the first carbon atom of the long hydrocarbon side chain and the carbon atom of the main chain to which the side chain is attached.
• polymers wherein the aliphatic hydrocarbon side chains are attached indirectly to the main chain via one or more oxygen and/or carbon atoms are-polymers-wherein the aliphatic hydrocarbon side chains are attached to the main chain via a carboxyl group or via an oxygen atom, or via at least two carbon atoms of an aromatic ring system.
• these polymers may basically be carried out in two manners.
• Olefinically unsaturated compounds of this type will hereinafter be termed olefinically unsaturated compounds containing a long hydrocarbon chain.
• a second manner in which these small quantities of polymer are necessary to re'achthe polymers can be prepared is by polymerization of olefinically unsaturated compounds containing no long hydrocarbon'chain and aftertreatment of the polymer, by means of which these long hydrocarbon chains are introduced into the polymer as side chains.
• the polymers applicable as pour point depressants according to the invention may be either homopolymers or copolymers.
• the material to be polymerized should invariably contain olefinically unsaturated compounds with long hydrocarbon chains.
• the starting material is one specific olefinically unsaturated monomer with a long hydrocarbon chain.
• the starting material is a monomer mixture which, in addition to a specific olefinically unsaturated monomer with a long hydrocarbon chain, contains one or more other monomers which may or may not contain a long hydrocarbon chain.
• the material to be polymerized need not contain any olefinically unsaturated compounds with long hydrocarbon chains.
• the starting material is one specific olefinically unsaturated monomer from which a polymer can be prepared that is suitable for the desired after-treatment.
• thestarting material is, for example, a mixture of monomers, which, in addition to one specific monomer from which a polymer can be prepared that is suitable for the desired aftertreatment, contains one or more other monomers which may or may not contain a long hydrocarbon chain.
• the molecular weight of the polymers applicable as flow improvers of the invention may vary between wide limits. For application in practice it is preferable to choose polymers whose average molecular weight (number of average M ranges between 1,000 and 1,000,000, in particular between 4,000and 100,000.
• olefinically unsaturated compounds containing long hydrocarbon chains suitable for the preparation of the polymers according to the invention, are vinyl esters and allyl esters of saturated monocarboxylicacids, such as vinyl esters and al'lyl esters of arachidic acid and behenic acid; alkyl esters of unsaturated monocarboxylic acids, such as n-octad'ecyl acrylate and n-eicosyl methacrylate alkyl amides of unsaturated monocarboxylic acids such as n-eicosyl acrylamide and n-docosyl methacrylamide; dialkyl esters of unsaturated dicarboxylic acids, such as di-noctadecyl maleate and di-n-tetracosyl fumarate; dialkylamides of unsaturated dicarboxylic acids, such as din-eicosylmaleic diamide and di-n-docosylfumaric diamide; imides of uns
• vinyl esters of unsaturated monocarboxylic acids such as vinyl acetate
• alkyl esters of unsaturated mono and dicarboxylic acids such as methyl methacrylate and diethyl maleate
• alkyl vinyl ethers such as octyl vinyl ether
• mono-oletms such as
• polymers'obtained by direct polymerization of olefinically unsaturated compounds of which at least a proportion consists of olefinically unsaturated compounds with long hydrocarbon chains are, for instance:
• Copolymers of vinyl esters of saturated monocarboxylic acids with one another are Copolymers of vinyl esters of saturated monocarboxylic acids with one another.
• Copolymers of vinyl esters of saturated monocarboxylic acids with mono-olefins are preferred.
• Copolymers of alkyl esters of unsaturated monocarboxylic acids with one another are possible.
• Copolymers of alkyl esters of unsaturated monocarboxylic acids with dialkyl esters of unsaturated dicarboxylic acids or with mono-olefins are preferred.
• Copolymers of dialkyl esters of unsaturated dicarboxylic acids with mono-olefins are copolymers of dialkyl esters of unsaturated dicarboxylic acids with mono-olefins.
• the polymers are copolymers they may be built up either of two or of more than two different monomers.
• terpolymers are, for instance, terpolymers obtained by copolymerization of a vinyl ester of a saturated monocarboxylic acid with a dialkyl ester of an unsaturated dicarboxylic acid and a mono-olefin or an alkyl ester of an unsaturated monocarboxylic acid.
• polymet9 tained by polymerization of olefinically unsaturated compounds containing no long hydrocarbon chains and where, by aftertreatment of the polymer, long hydrocarbon chains are introduced into the polymer as side chains, are, for example: a a
• Homopolymers of unsaturated alcohols which polymers have been after-treated with an aliphatic carboxylic acid or aliphatic carboxylic chloride containing a long hydrocarbon chain.
• Copolymers of anhydrides of unsaturated dicarboxylic acids with mono-olefins or other olefinically unsaturated compounds which polymers have been aftertreated with an aliphatic amine containing a long hydrocarbon chain.
• polymers which contain aliphatic hydrocarbon side chains with at least 14 carbon atoms and which may be taken to have been obtained by polymerization of olefinically unsaturated compounds are in 7 general suitable for improving the flow properties of waxy crude oils, preference is given to polymers which may be taken to have been obtained by polymerization of olefinically unsaturated compounds which consist at least partly of olefinically unsaturated aliphatic compounds containing a saturated hydrocarbon chain with at least 14 carbon atoms.
• Homoor copolymers of alkyl esters of unsaturated carboxylic acids such as homoor copolymers of alkyl esters of unsaturated monocarboxylic acids, in particular homoor copolymers of alkyl acrylates.
• alkyl 'acrylates are homopolymers of n-tetradecyl acrylate, homopolymers of n-hexadecyl acrylate, homopolymers of n-octadecyl acrylate and homopolymers of n-eicosyl acrylate.
• Copolymers of a mono-olefin and a dialkyl ester of an unsaturated dicarboxylic acid with at least. 14 carbon atoms in the alkyl groups in particular'copolymers of ethylene and di-n-octadecyl maleate.
• Homoor copolymers of vinylesters of saturated monocarboxylic acids in particular copolymers of vinyl esters of hydrogenated rape-seed oilfatty acids.
• homoor copolymers of alkyl esters of unsaturated carboxylic acids such as homoor copolymers of alkyl esters of unsaturated monocarboxylic acids, in particular homoor copolymers of alkyl acrylates.
• homoor copolymers of alkyl acrylates having 18 to 26 carbon atoms in the alkyl group in particular a homopolymer of noctadecyl acrylate and a homopolymer of n-eicosyl acrylate.
• the concentration in which the polymers may be applied may vary between wide limits', depending upon the nature, the structure and the molecular weight of the polymer to be employed, the nature of and the quantity of the paraffin waxes present in the crude oil, and the improvement of the flow properties envisaged.
• a quantity of 0.001 percent w, calculated on the crude oil composition is already sufficient for attaining the desired improvement in flow properties. in mostcases, a quantity of 2.0 percentgw is amply sufficient.
• the polymers Preferably, from 0.002 percent w to 0.2 percent w of the polymers is incorporated into the crude oil.
• the present polymers have so far been designated in the specification as flow improvers of waxycrude oils. Their features include properties to reduce the pour point, the viscosity and the yield stress of waxy crude oils. With regard to each of these properties: separately they can, if desired, also be designated as pour point depressants, viscosity depressants and yield stress depressants. In this connection it should be observed that a compound may in general be regarded as belonging to the class of pour point depressants only if it is capable of effecting a pour point reduction of at least 6C when it is applied in a concentration of at most 0.2 percent w.
• the waxy crude oil to which the polymers according The present polymers which are particularly important as additives to ease the transport of waxy crude oils through pipelines, by tankers or by other means, can also be very suitably used in oil wells producing waxy crude to prevent the-formation of waxy deposits or to dissolve such deposits formed on the walls of the well.
• Crude Oil I Crude Oil 11 A crude oil originating from South America, with a kinematic viscosity of 1.82 cS at C, a wax content of 17.5 percent w (setting point of the wax 54.5C), a pour point of 26C, determined according to method A, and a pour 'point'of 29C, determined according to method C.
• Crude Oil III A crude oil originating from North Africa, with a kinematic viscosity of 5.13 cS at 37.8C, a wax content of 7.0 percent w'(setting point, of the wax 58.0C), a pour point of 4C, determined according to method A, and a pour point of +2C, determined according to method Crude on [V A crude oil originating from North Africa, with a kinematic viscosity of 3.66 cS at 37.8C, a wax content of 7.8 percent w (setting point of the wax 51.5C), a pour point of +2C, determined according to method A, and a pour point of +5C, determined according to method Crude Oil Vv A crude oil originating from West Africa, with a kinematic viscosity of 15.0 cS at 50C, a wax content of 17.8 percent w (setting point of the wax 56.0C), a pour point of 20C, determined according to method B, and a pour point of 32C, determined according to method
• Crude Oil VI A crude oil originating from West Africa, with a kinematic viscosity of 2.70 cS at 50C, a wax content of 7.0
• the pour point of a waxy crude oil is often dependent upon the thermal pre-treatment to which the oil has been subjected.
• the methods suitable for the determination of the pour point of waxy crude oils may be divided into two groups, viz.:
• the polymers of the invention are capable of depressing the pour point in a general sense, i.e., independent of whether or not the thermal pre-treatment is carried out.
• METHOD B As described under method A, but in its first line read 100C instead of 65C.
• YIELD STRESS A sample of crude oil is heated to 65C, at which temperature the desired quantity of polymer is added to the sample. After cooling to room temperature a metal U-tube with a length of 54 cm and an inside diameter of 3.8 mm is filled with the oil to be tested. Subsequently, the oil in the tube is cooled down to the de;
• the pressure (P,,) at which the first flow is observed is used for calculating the yield stress.
• the yield stress (defined as the shear stress required for setting a congealed oil into motion) is calculated from the observed P with the aid of the equation:
• a sample of crude oil is heated to C, at which temperature the desired quantity of polymer is added to the sample. After cooling down to room temperature the reservoir of the viscometer is filled with the oil to be tested.
• test sec 36.9 164 628 temperatue, C 21.4 56 c? 34 cP 32 cP 18.3 82 c? 46 cl 37 c? 15.5 110 cl 52 c? 41 0P 9.7 159 c? 69 CP 47 c? 5.2 223P s7 cP 47 of When the cargo was loaded in North Africa for the 1st voyage, threesamples of crude oil VII were taken.
• Sample 2 crude oil VII 1 0.02 percent w poly-n-C alkyl acrylate.
• the oil undertest was pumped at itstemperature of arrival into the circuit, after which the pump was stopped for some days (shut-in time), so that the oil was allowed to cool down. Subsequently the pressure at the inlet of the circuit was raised by means of a pump in steps until the oil began to flow.
• the yield stress was calculated from the highest pressure drop over the noninsulated (i.e., cooled) pipe section by means of the afore-mentioned formula:
• the flow improver used was 0.015 percent w poly-n-C alkyl acrylate.
• ViscosityKFerranti viscometer rate of shear, test sec" 36.9 164 328 temperature, CC V 22.7 37 cl 30 c? 29 cP 10.2 13161 81 cP CE 4.8 210 CP 119 cP 93 cP It was found that the rate of discharge of the doped oil from the tanker was 15 percent higher than that of the undoped oil.
• a composition of matter having improved flow and friction-reducing properties comprising 1 a major amount of waxy crude oil having incorporated therein from 0.001 to 2 percent of an oil-soluble polymer containing aliphatic hydrocarbon side chains having the formula CH,-(Cl-l,),,-CH where n is an integer of from 14 to 30, said polymer having a molecular weight of from 1,000 to 1,000,000 and being a member selected from the group consisting of (a) homopolymers of alkyl vinyl ethers or copolymers of alkyl vinyl ethers with one another and (b) copolymers of a mono-olefin and a dialkyl ester of an unsaturated dicarboxylic acid.
• composition of claim 1 in which the polymer is obtained by homopolymerization of an alkyl vinyl ether containing an aliphatic hydrocarbon chain or from 14 carbon atoms.
• composition of claim 1 in which the polymer is obtained by copolymerization of a mono-olefin with a dialkyl ester of an unsaturated dicarboxylic acid, which ester contains aliphatic hydrocarbon chains or from 14 to 30 carbon atoms in the parts of the molecule derived from the alcohol.
• a method of transporting waxy crude oil through a pipeline under reduced friction and without causing plugging of the pipeline comprising adding to the waxy crude oil from 0.001 to 2 percent of an oil-soluble polymer containing aliphatic hydrocarbon side chains having the formula CH -(CH ),,Cl-l where n is an integer of from 14 to 30; said polymer having a molecular weight of from 1,000 to 1,000,000 and being a member selected from the group consisting of (a) homopolymers of alkyl vinyl ethers or copolymers of alkyl vinyl ethers with one another and (b) copolymers of a monoolefin and a dialkyl ester of an unsaturated dicarboxylic acid.

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• Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Engineering & Computer Science (AREA)
• Organic Chemistry (AREA)
• Combustion & Propulsion (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
• Lubricants (AREA)
• Liquid Carbonaceous Fuels (AREA)

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Citations (7)

• 1967
  • 1967-07-07 NL NL6709453A patent/NL6709453A/xx unknown
• 1968
  • 1968-06-04 SE SE741068A patent/SE355377B/xx unknown
  • 1968-06-04 IE IE656/68A patent/IE32096B1/xx unknown
  • 1968-06-05 NO NO02197/68A patent/NO127015B/no unknown
  • 1968-06-17 YU YU138868A patent/YU138868A/xx unknown
  • 1968-06-18 GB GB2894068A patent/GB1161188A/en not_active Expired
  • 1968-06-19 DK DK289168A patent/DK138374B/da not_active IP Right Cessation
  • 1968-06-19 FI FI171768A patent/FI51712C/fi active
  • 1968-06-21 AT AT598968A patent/AT289993B/de not_active IP Right Cessation
  • 1968-06-24 DE DE19681770695 patent/DE1770695A1/de active Pending
  • 1968-06-26 CH CH948868A patent/CH496794A/de not_active IP Right Cessation
  • 1968-06-27 BE BE717234D patent/BE717234A/xx unknown
  • 1968-07-01 SU SU1252377A patent/SU365898A3/ru active
  • 1968-07-01 US US3776247D patent/US3776247A/en not_active Expired - Lifetime
  • 1968-07-05 FR FR1575984D patent/FR1575984A/fr not_active Expired
  • 1968-07-05 CA CA024,453A patent/CA980118A/en not_active Expired
  • 1968-07-06 ES ES355848A patent/ES355848A1/es not_active Expired
  • 1968-07-06 OA OA53317A patent/OA02849A/xx unknown

Patent Citations (7)

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