EP1357172B1 - Produits de réaction imine-acide, solubles dans l'huile comme dispersants d'asphaltène dans le pétrole brut - Google Patents

Produits de réaction imine-acide, solubles dans l'huile comme dispersants d'asphaltène dans le pétrole brut Download PDF

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Publication number
EP1357172B1
EP1357172B1 EP20030252271 EP03252271A EP1357172B1 EP 1357172 B1 EP1357172 B1 EP 1357172B1 EP 20030252271 EP20030252271 EP 20030252271 EP 03252271 A EP03252271 A EP 03252271A EP 1357172 B1 EP1357172 B1 EP 1357172B1
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Prior art keywords
group
imine
salt
alkyl
acid
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EP1357172A3 (fr
EP1357172A2 (fr
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Ravindranath Mukkamala
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Rohm and Haas Co
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Rohm and Haas Co
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    • 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
    • C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
    • 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
    • C10L1/2493—Organic compounds containing sulfur, selenium and/or tellurium compounds of uncertain formula; reactions of organic compounds (hydrocarbons, acids, esters) with sulfur or sulfur containing 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, 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
    • C10L1/26—Organic compounds containing phosphorus
    • C10L1/2691—Compounds of uncertain formula; reaction of organic compounds (hydrocarbons acids, esters) with Px Sy, Px Sy Halz or sulfur and phosphorus containing 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, 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
    • C10L1/1608—Well defined compounds, e.g. hexane, benzene
    • 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
    • C10L1/1616—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, 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
    • C10L1/188—Carboxylic acids; metal salts 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • 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
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/189—Carboxylic acids; metal salts thereof having at least one carboxyl group bound to an aromatic carbon atom
    • 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
    • C10L1/228—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
    • C10L1/2283—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen double bonds, e.g. guanidine, hydrazone, semi-carbazone, azomethine
    • 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
    • C10L1/2431—Organic compounds containing sulfur, selenium and/or tellurium sulfur bond to oxygen, e.g. sulfones, sulfoxides
    • C10L1/2437—Sulfonic acids; Derivatives thereof, e.g. sulfonamides, sulfosuccinic acid esters
    • 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
    • C10L1/26—Organic compounds containing phosphorus
    • C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond

Definitions

  • This invention relates generally to oil-soluble imine-acid reaction products useful in processing of crude oil.
  • GB-A-1 506 786 discloses an oil composition comprising a major proportion of an oil and 0.01-15% by weight of a basic dispersant.
  • Said dispersant is the reaction product of an alkyl or alkenyl succinic acid or anhydride with a polymer of an alkylene imine.
  • US-A-6 140 276 discloses a method of reducing the deposition of wax from crude oil containing wax, which comprises adding thereto at least one N-substituted polyalkylene imine which has at least one organic substituent that is a hydroxy-substituted alkyl group of 12-24 carbon atoms.
  • US-A-6171 521 teaches a zwitterionic water-soluble imine.
  • the problem addressed by this invention is to find materials suitable for improving processing of petroleum products.
  • This invention is directed to a composition
  • a composition comprising: (a) 0.001% to 20% of at least one reaction product of (i) an imine; and (ii) an organic acid; and (b) crude oil wherein said reaction product is a salt of a carboxylic, phosphonic or sulphonic acid, and the salt has a polar group located two to ten chemical bonds from either : (i) a carbonyl carbon of a carboxylate group, a phosphorus atom of a phosphonate group or a sulfur atom of a sulfonate group; or (ii) a nitrogen atom of a protonated imine group; further wherein the salt has cation and an anion and is not zwitterionic.
  • This invention is directed further to a method for dispersing asphaltenes in a petroleum product by adding to the petroleum product 0.001% to 20% of at least one reaction product of: (a) an imine; and (b) an organic acid.
  • a "polar” group is a functional group selected from among the following: hydroxy, oxime, amide, alkyl amide, ester, ammonium, alkylammonium, nitroso, mercapto, alkylthio, alkylsulfonyl, alkylsulfenyl, and alkylsulfinyl.
  • An “organic acid” is an acid which is not a mineral acid.
  • An “alkyl” group is a hydrocarbyl group having from one to twenty-two carbon atoms in a linear, branched or cyclic arrangement. Alkyl groups optionally have one or more double or triple bonds.
  • alkyl groups are substituted by one or more halo substituents.
  • a "heteroalkyl” group is an alkyl group in which at least one carbon has been replaced by O, NR, or S, wherein R is hydrogen, alkyl, heteroalkyl, aryl or aralkyl.
  • An "aryl” group is a substituent derived from an aromatic hydrocarbon compound. An aryl group has a total of from six to twenty ring atoms, and has one or more rings which are separate or fused.
  • An “aralkyl” group is an “alkyl” group substituted by an “aryl” group.
  • a “heterocyclic” group is a substituent derived from a heterocyclic compound having from five to twenty ring atoms, at least one of which is nitrogen, oxygen or sulfur. Preferably, heterocyclic groups do not contain sulfur. Substitution on aryl or heterocyclic groups of one or more of halo, cyano, alkyl, heteroalkyl, alkoxy or the aforementioned polar groups is permitted, with substitution by one or more halo groups being possible on alkyl, heteroalkyl or alkoxy groups.
  • An “aromatic heterocyclic” group is a heterocyclic group derived from an aromatic heterocyclic compound. Preferably, heterocyclic groups in compounds used in this invention are aromatic heterocyclic groups.
  • an "organic functional group” is a functional group which does not contain metal atoms, and which has from one to twenty-two carbon atoms, hydrogen atoms, and optionally, contains heteroatoms, including but not limited to: nitrogen, oxygen, sulfur, phosphorus and halogen atoms.
  • An organic functional group optionally contains double and/or triple bonds; rings, which are linked or fused; and if it is wholly or partly acyclic, the acyclic part can be linear or branched.
  • an organic functional group is an alkyl, heteroalkyl, aryl, aralkyl, heterocyclic or heterocyclic-alkyl group.
  • At least one of the organic functional groups is a C 2 -C 22 alkyl or heteroalkyl group, more preferably a C 7 -C 22 alkyl or heteroalkyl group, more preferably a C 9 -C 22 alkyl or heteroalkyl group, and most preferably, a C 15 -C 22 alkyl group.
  • alkyl and heteroalkyl groups are unsubstituted.
  • reaction product of an imine and an acid is added to a petroleum product, with the total amount of said reaction product(s) being from 0.001% to 20%, preferably from 0.001% to 10%, more preferably from 0.01% to 10%, more preferably from 0.01% to 1%, and most preferably from 0.02% to 0.2%.
  • the reaction product has no new covalent bonds, i.e., bonds not present in the imine or the acid.
  • the reaction product is either a salt or a physical mixture or complex of the imine and the acid.
  • the reaction product used in this invention is a salt, preferably one that is soluble in oil at least at the aforementioned levels.
  • the salt has at least ten carbon atoms, more preferably at least 15 carbon atoms.
  • a salt used in this invention is aliphatic.
  • a salt used in this invention is acyclic.
  • the salt used in this invention has a cation and an anion, and is not zwitterionic.
  • the organic acid used in this invention is a carboxylic, phosphonic or sulfonic acid.
  • the acid is a carboxylic acid having no other acidic functional groups, i.e., groups having pK a ⁇ 6.
  • the acid is a phosphonic acid having no other acidic functional groups.
  • the acid is a sulfonic acid having no other acidic functional groups.
  • the separation between a polar group and a carboxylate, phosphonate or sulfonate ion is measured by the number of covalent chemical bonds intervening between either: (i) the atom of the polar group through which it is attached (e.g., the oxygen of hydroxy; the nitrogen of amino or nitroso; or the sulfur of sulfur-containing groups); or (ii) a carbonyl or imine carbon of the polar group (e.g., the carbonyl carbon of amide or the imine carbon of oxime); and one of: the carboxylate carbon, the phosphorus atom of a phosphonate, the sulfur atom of a sulfonate and the imine nitrogen atom.
  • conjuggate base group e.g., the oxygen of hydroxy; the nitrogen of amino or nitroso; or the sulfur of sulfur-containing groups
  • a carbonyl or imine carbon of the polar group e.g., the carbonyl carbon of amide or the imine carbon of oxime
  • the oxygen of the hydroxy group is two bonds from the carbonyl carbon of the carboxylate group.
  • at least one polar group in a compound of this invention is located two to eight chemical bonds from either a conjugate acid or base functional group, more preferably from two to seven chemical bonds, and most preferably two, three, four, five or six chemical bonds from either a conjugate acid or base functional group.
  • a compound used in this invention optionally contains other carboxylate, phosphonate, sulfonate or protonated imine functional groups on one or more of the organic functional groups, preferably for a total of one to five conjugate acid functional groups and one to five conjugate base functional groups.
  • the compound has one conjugate acid group and one conjugate base group.
  • a polar group is a hydrogen bond donor, e.g., a hydroxy, oxime, amide, or alkyl amide functional group; or a nitro group. More preferably, a polar group is a hydroxy or amide functional group. Most preferably, a polar group is a hydroxy group.
  • the salt has formula (I), wherein R 1 , R 2 , R 3 and R 4 independently are hydrogen or organic functional groups. Other carboxylate groups or other protonated imine groups optionally are present on R 1 , R 2 , R 3 or R 4 .
  • R 1 , R 2 , R 3 and R 4 independently are hydrogen, alkyl, heteroalkyl, aryl, aralkyl or heterocyclic.
  • R 1 , R 2 , R 3 and R 4 do not contain other carboxylate groups.
  • R 2 is C 2 -C 22 alkyl, more preferably C 7 -C 22 alkyl, more preferably C 9 -C 22 alkyl, and most preferably, C 15 -C 22 alkyl.
  • the imine part of the compound of formula (I) is derived from an unsubstituted C 15 -C 22 alkyl amine, R 2 NH 2 , preferably one which is an oil-soluble amine.
  • the alkyl amine is a tertiary alkyl primary amine, i.e., a primary amine in which the alkyl group is attached to the amino group through a tertiary carbon.
  • tertiary alkyl primary amines examples include the Primene TM amines available from Rohm and Haas Company, Philadelphia, PA.
  • a polar group is present and is located two to ten chemical bonds from either: a carbonyl carbon of a carboxylate group; or a nitrogen atom of a protonated imine group.
  • the carboxylate ion of a salt used in this invention has formula (II) wherein R 5 and R 6 independently are hydrogen, alkyl or hydroxy; X is O - or R 7 R 8 N; and R 7 and R 8 independently are hydrogen, alkyl, aryl, aralkyl or heteroalkyl.
  • R 7 is hydrogen and R 8 is 2-hydroxyethyl.
  • R 5 and R 6 both are hydroxy and X is O - .
  • R 5 is alkyl
  • X is R 7 R 8 N
  • R 6 is hydrogen; preferably, at least one of R 5 , R 7 and R 8 is C 8 -C 22 alkyl, more preferably C 15 -C 22 alkyl.
  • the carboxylate ion of formula (II) occurs in a salt with at least one protonated imine.
  • the carboxylate ion of a salt is selected from the group consisting of: and wherein R 9 , R 10 , R 11 , and R 12 independently are alkyl, aryl, aralkyl or heteroalkyl; m is zero or one; and n is one, two or three.
  • the composition of the present invention typically also increases demulsibility, reduces sediment formation, reduces surface fouling and reduces corrosion.
  • the composition of the present invention can be injected directly into an injection well, or preferably diluted with solvent prior to injection.
  • Suitable solvents include but are not limited to: petroleum distillates such as kerosene and gas oil; linear and branched aliphatic solvents such as pentane, hexanes, mixtures of nonanes and 2-ethylhexanes; cycloaliphatic mixtures commonly known as naphtha; aromatic solvents such as toluene, xylenes and commercial aromatic solvent mixtures; esters; ethers; alcohols such as ethanol, isopropanol, octanol and dodecanol; ketones such as acetone, cyclohexanone and acetophenone; and other polar solvents.
  • petroleum distillates such as kerosene and gas oil
  • linear and branched aliphatic solvents such as pentane, hexanes, mixtures of nonanes and 2-ethylhexanes
  • cycloaliphatic mixtures commonly known as naphtha
  • aromatic solvents such as toluen
  • Preferred dilutions are 0.01 to 50 wt% of the compound in the solvent, more preferred dilutions being 0.01 to 20 wt%, more preferred dilutions being 0.1 to 10%, and most preferred dilutions being 1 to 10 wt %.
  • Asphaltene Dispersancy-test tube method This test requires a previously made dispersion of asphaltene in xylenes (Aromatic 150 solvent) or asphaltenic heavy crude diluted in xylenes (Aromatic 150 solvent) at a known concentration.
  • a solution of an additive formulation (0.1 mL, the active ingredient was typically at 5-10 wt%, making the treat rate 500-1000 ppm) was taken in to a 15.0 mL graduated glass centrifuge tube, and hexanes added such that the total volume in the tube became 10.0 mL.
  • asphaltenic stock solution 0.1 mL
  • the test tube was then capped, shaken vigorously for about a minute or 40-60 times by hand and allowed to stand.
  • the volume of any precipitated asphaltenes settled at the bottom of the tube was recorded at 10, 30, 60, 90 and 1440 (24 h) min intervals.
  • the volume of asphaltenes precipitated in the first 0.5-1 h was 0.4-0.5 mL (4-5%); in fact, it was important to initially adjust the concentration of the asphaltene stock in such a way that under these conditions of dilution with paraffinic solvents, a 4-5 vol% of asphaltenic precipitation occurred.
  • the methylene imines were prepared by treating the indicated amine with formaldehyde.
  • the treat rate is the concentration of the salt in the crude oil.
  • Primene TM amines are tertiary alkyl primary amines in which the alkyl groups are a mixture of isomers.
  • the alkyl group is a mixture of C 10 -C 15 alkyl groups; and in Primene TM JM-T amine, of C 16 -C 22 alkyl groups.

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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)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Claims (9)

  1. Composition comprenant :
    (a) 0,001 % à 20 % d'au moins un produit de réaction de (i) une imine ; et (ii) un acide organique ; et
    (b) du pétrole brut ;
    dans laquelle ledit produit de réaction est un sel d'un acide carboxylique, phosphonique ou sulfonique, et le sel comporte un groupe polaire situé à deux à dix liaisons chimiques de soit : (i) un atome de carbone de carbonyle d'un groupe carboxylate, un atome de phosphore d'un groupe phosphonate ou un atome de soufre d'un groupe sulfonate ; soit (ii) un atome d'azote d'un groupe imine protoné, dans laquelle en outre le sel a un cation et un anion et n'est pas zwitterionique.
  2. Composition selon la revendication 1, dans laquelle ledit groupe polaire est un groupe hydroxy, oxime, nitro, ester, amide ou alkyl amide.
  3. Composition selon la revendication 1, dans laquelle ledit groupe polaire est un groupe hydroxy, et est situé à deux à six liaisons chimiques de soit : (i) un atome de carbone de carbonyle d'un groupe carboxylate, un atome de phosphore d'un groupe phosphonate ou un atome de soufre d'un groupe sulfonate ; soit (ii) un atome d'azote d'un groupe imine.
  4. Composition selon la revendication 3, dans laquelle ledit au moins un sel est un sel d'une imine et d'un acide carboxylique, et n'a aucun autre groupe fonctionnel acide.
  5. Procédé de dispersion d'asphaltènes dans un produit de pétrole ; ledit procédé comprenant l'addition au produit de pétrole de 0,001 % à 20 % d'au moins un sel de :
    (a) une imine ; et
    (b) un acide organique.
  6. Procédé selon la revendication 5, dans lequel ledit produit de réaction est un sel d'un acide carboxylique, phosphonique ou sulfonique, et le sel comporte un groupe polaire situé à entre deux et dix liaisons chimiques de soit : (i) un atome de carbone de carbonyle d'un groupe carboxylate, un atome de phosphore d'un groupe phosphonate ou un atome de soufre d'un groupe sulfonate ; soit (ii) un atome d'azote d'un groupe imine protoné.
  7. Procédé selon la revendication 6, dans lequel ledit groupe polaire est un groupe hydroxy, oxime, nitro, ester, amide ou alkyl amide.
  8. Procédé selon la revendication 7, dans lequel ledit groupe polaire est situé à deux à six liaisons chimiques de soit : (i) un atome de carbone de carbonyle d'un groupe carboxylate, un atome de phosphore d'un groupe phosphonate ou un atome de soufre d'un groupe sulfonate ; soit (ii) un atome d'azote d'un groupe imine.
  9. Procédé selon la revendication 8, dans lequel ledit au moins un sel est un sel d'une imine et d'un acide carboxylique, et n'a aucun autre groupe fonctionnel acide.
EP20030252271 2002-04-23 2003-04-10 Produits de réaction imine-acide, solubles dans l'huile comme dispersants d'asphaltène dans le pétrole brut Expired - Fee Related EP1357172B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US37487702P 2002-04-23 2002-04-23
US374877P 2002-04-23

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EP1357172A2 EP1357172A2 (fr) 2003-10-29
EP1357172A3 EP1357172A3 (fr) 2004-03-17
EP1357172B1 true EP1357172B1 (fr) 2006-07-05

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EP20030252271 Expired - Fee Related EP1357172B1 (fr) 2002-04-23 2003-04-10 Produits de réaction imine-acide, solubles dans l'huile comme dispersants d'asphaltène dans le pétrole brut

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EP (1) EP1357172B1 (fr)
CA (1) CA2424915A1 (fr)
DE (1) DE60306574D1 (fr)
MX (1) MXPA03003359A (fr)
NO (1) NO20031602L (fr)

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Publication number Priority date Publication date Assignee Title
CA2424811C (fr) * 2002-04-23 2008-08-05 Rohm And Haas Company Carbonyles, thiocarbonyles ou imines utilises comme dispersants d'asphaltenes dans du petrole brut
US7097759B2 (en) 2003-05-23 2006-08-29 Rohm And Haas Company Carbonyl, thiocarbonyl or imine containing compounds as asphaltene dispersants in crude oil
EP3201297B1 (fr) 2014-10-02 2020-07-15 Croda, Inc. Inhibition de l'asphaltène
WO2017223028A1 (fr) 2016-06-24 2017-12-28 Croda, Inc. Procédé et composition destinés à la dispersion d'asphaltènes
GB2573348A (en) * 2018-05-05 2019-11-06 Innospec Ltd Method

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US3326975A (en) * 1963-02-11 1967-06-20 Eastman Kodak Co Amide or imine hydrocarbon fuel stabilizers
GB1506786A (en) * 1976-02-20 1978-04-12 Shell Int Research Oil compositions
GB9526325D0 (en) * 1995-12-22 1996-02-21 Bp Exploration Operating Inhibitors
US5993693A (en) * 1998-11-09 1999-11-30 Nalco/Exxon Energy Chemicals, L.P. Zwitterionic water-soluble substituted imine corrosion inhibitors
NO20031605L (no) * 2002-04-23 2003-10-24 Rohm & Haas Amin-syre-reaksjonsprodukter som asfaltendispergenter i råolje
CA2424811C (fr) * 2002-04-23 2008-08-05 Rohm And Haas Company Carbonyles, thiocarbonyles ou imines utilises comme dispersants d'asphaltenes dans du petrole brut

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Publication number Publication date
DE60306574D1 (de) 2006-08-17
EP1357172A3 (fr) 2004-03-17
CA2424915A1 (fr) 2003-10-23
NO20031602L (no) 2003-10-24
NO20031602D0 (no) 2003-04-09
EP1357172A2 (fr) 2003-10-29
MXPA03003359A (es) 2005-08-16

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