CA2471413A1 - Use of sulphonated alkyl phenol formaldehydes in the stabilization of ashphaltenes in crude oil - Google Patents
Use of sulphonated alkyl phenol formaldehydes in the stabilization of ashphaltenes in crude oil Download PDFInfo
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- CA2471413A1 CA2471413A1 CA002471413A CA2471413A CA2471413A1 CA 2471413 A1 CA2471413 A1 CA 2471413A1 CA 002471413 A CA002471413 A CA 002471413A CA 2471413 A CA2471413 A CA 2471413A CA 2471413 A1 CA2471413 A1 CA 2471413A1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/52—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
- C09K8/524—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning organic depositions, e.g. paraffins or asphaltenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/10—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aromatic carbon atoms, e.g. polyphenylenes
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- Organic Chemistry (AREA)
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- Engineering & Computer Science (AREA)
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- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
Disclosed is the use of sulphonated alkyl phenol formaldehydes as stabilizers for asphaltenes in crude oil.
Description
Use of Sulfonated Alkyl Phenol Formaldehydes in the Stabilization of Asphaltenes in Crude Oil This invention relates to certain sulfonated alkylphenol formaldehydes and to their use for stabilizing asphaltenes in crude oil and to a process for preventing the precipitation of asphaltenes in crude oils.
Crude oil is a complex mixture of various paraffinic and aromatic hydrocarbons in which the individual constituents have very different chemical and physical properties. Accordingly both readily volatile, low viscosity constituents and wax-like, high-viscosity fractions are obtained in the distillation of crude oil. The second of these two groups includes petroleum resins and, to a predominant extent, asphaltenes which are colloidally dispersed in the oil phase.
The asphaltenes consist of a mixture of various saturated, unsaturated and aromatic hydrocarbons, more particularly naphthalene derivatives. They also contain heterocyclic hydrocarbons which, in part, also contain complexed metal ions. In addition, asphaltenes are rich in sulfur, nitrogen and oxygen compounds. Because of their complex composition, asphaltenes are generally characterized on the basis of their solubility. Thus, the petroleum fraction insoluble in heptane or pentane, but soluble in toluene is referred to as asphaltenes, the "dissolution" of asphaltenes involving a complex process for which there has as yet been no complete theoretical explanation (cf. E.Y. Scheu, O.C. Mullins, Asphaltenes - Fundamentals and Applications, Plenum Press, New York, 1995, Chapter I and Chapter III).
Asphaltenes are present as micelle colloids in the oil phase of crude oil, the individual micelles consisting of several different molecules. The micelles vary in size according to the temperature and composition of the oil phase. For example, it is known that relatively light aromatic hydrocarbons in crude oil stabilize the asphaltene micelles. Under the conditions prevailing in petroleum production, however, the asphaltenes are often precipitated which results in the formation of highly viscous, wax-like or solid residues on the surface of the production units and the petroleum-containing formation surrounding the well. The asphaltene residues block the pores of the formation which leads to a noticeable reduction in the production rates and, in the worst case, can make production completely impossible. Asphaltene residues on the surfaces of the production units, for example the delivery tube or the casing walls of pipelines or separators, can also considerably reduce production.
Accordingly, there are various known methods for keeping asphaltenes dispersed in crude oil and for preventing their precipitation.
DE 197 09 797 describes synergistic mixtures of alkyl phenol formaldehyde resins and certain alkoxylated amines as asphaltene dispersants. It is known from US 4,414,035 that alkyl aryl sulfonic acid derivatives, for example dodecyl benzenesulfonic acid, disperse asphaltenes in crude oils.
However, it has often been found in practice that known auxiliaries for stabilizing asphaltenes differ very considerably in their effectiveness according to the nature and origin of the crude oil. This is attributable in particular to the complex and highly variable structure of the asphaltenes.
Accordingly, efforts have been made to find new asphaltene stabilizers. In addition, known asphaltene stabilizers are often either toxic and/or ecologically unsafe. Because of this, it is preferred to avoid using them both for reasons of environmental safety and in the interests of safety at work.
Accordingly, the problem addressed by the present invention was to provide effective alternatives to the stabilizers known from the prior art for stabilizing asphaltenes in crude oils, despite very different crude oil qualities. It has been found that certain sulfonated alkyl phenol formaldehydes solve this problem.
In a first embodiment, therefore, the present invention relates to the use of products obtainable by sulfonation of compounds corresponding to formula (I) or (II):
R
R-Ph-[Ph]n Ph-R (I) R
- [Ph-CHZ-] n- (II) in which n is a number of 2 to 12 and R is a C3_2a alkyl, C6_~2 aryl or hydroxyaryl or C~_~2 aralkyl group, as stabilizers for asphaltenes in crude oil. In addition, Ph in formula(I) and (II) is a phenol residue.
The sulfonation products used in accordance with the invention are obtained by sulfonation of compounds known per se corresponding to general formulae (I) and/or (II). These starting products are known, for example, from DE 197 09 797 A1. Reference is made here to formulae (I) and (II) in claim 1 of DE 197 09 797 A1, to the disclosure on page 2, lines 40 to 44 and to the disclosure on page 3 of that document. The disclosures of those passages are specifically included in the disclosure of the present application. Formulae (I) and (II) in DE 197 09 797 are identical with those of the present application. The compounds in question are resins which are obtainable, for example, under the name of Dowfax DM 645 (Dow Chemicals).
The educts corresponding to formulae (I) and (II) are sulfonated in known manner with gaseous S03. According to the invention, however, the sulfonation products are not neutralized, but are present as free acids. The sulfonation of the educts is preferably carried out by a continuous process in a falling film reactor. The gaseous sulfur trioxide is produced in situ by pyrolysis of pure sulfur. The polyalkyl formaldehyde resin used is preferably reacted with sulfur trioxide in an equimolar ratio. The reaction itself advantageously takes place at a temperature of 75 to 80°C. The end product is preferably not neutralized. The products according to the invention are obtained in the form of aqueous solutions which may be directly formulated and used as asphaltene dispersants without any further steps. The sulfonated products surprisingly exhibit distinctly better properties as asphaltene inhibitors or asphaltene stabilizers than the compounds known from the prior art or mixtures thereof according to the teaching of DE 197 09 797 A1.
Crude oil in the context of the present invention is understood to be the unrefined petroleum coming directly from the ground. This unrefined petroleum consists of complex mixtures of, predominantly, hydrocarbons with densities of 0.65 to 1.02 g/cm3 and calorific values of 38 to 46 MJ/kg.
The boiling points of the most important constituents of crude oil are in the temperature range from 50 to 350°C (cf. Rompp, Chemielexikon, Vol. 2, 1997, pages 1210 to 1213).
The use of the sulfonated alkylphenol formaldehydes in accordance with the invention, i.e. their addition to crude oils, effectively prevents the precipitation of asphaltenes and the formation of residues. In order to prevent the precipitation of asphaltenes, it is of advantage to add the sulfonated alkylphenol formaldehydes to the crude oil in quantities of 50 to 2500 ppm, preferably in quantities of 100 to 1000 ppm and more particularly in quantities of 150 to 500 ppm (active substance).
The present invention also relates to a process for preventing the precipitation of asphaltenes from crude oils, characterized in that sulfonated alkylphenol formaldehydes corresponding to the foregoing description are added to the crude oils as stabilizers in quantities of 100 to 2500 ppm.
The present technical teaching also encompasses the use of the sulfonated alkylphenol formaldehydes in the form of dilute solutions in aromatic solvents, preferably toluene. These dilute solutions contain the polyester amides in quantities of preferably 2 to 50% by weight, more preferably 2 to 20% by weight and most preferably 2 to 15% by weight.
Corresponding formulations may also contain other additives, such as corrosion inhibitors or defoamers.
Crude oil is a complex mixture of various paraffinic and aromatic hydrocarbons in which the individual constituents have very different chemical and physical properties. Accordingly both readily volatile, low viscosity constituents and wax-like, high-viscosity fractions are obtained in the distillation of crude oil. The second of these two groups includes petroleum resins and, to a predominant extent, asphaltenes which are colloidally dispersed in the oil phase.
The asphaltenes consist of a mixture of various saturated, unsaturated and aromatic hydrocarbons, more particularly naphthalene derivatives. They also contain heterocyclic hydrocarbons which, in part, also contain complexed metal ions. In addition, asphaltenes are rich in sulfur, nitrogen and oxygen compounds. Because of their complex composition, asphaltenes are generally characterized on the basis of their solubility. Thus, the petroleum fraction insoluble in heptane or pentane, but soluble in toluene is referred to as asphaltenes, the "dissolution" of asphaltenes involving a complex process for which there has as yet been no complete theoretical explanation (cf. E.Y. Scheu, O.C. Mullins, Asphaltenes - Fundamentals and Applications, Plenum Press, New York, 1995, Chapter I and Chapter III).
Asphaltenes are present as micelle colloids in the oil phase of crude oil, the individual micelles consisting of several different molecules. The micelles vary in size according to the temperature and composition of the oil phase. For example, it is known that relatively light aromatic hydrocarbons in crude oil stabilize the asphaltene micelles. Under the conditions prevailing in petroleum production, however, the asphaltenes are often precipitated which results in the formation of highly viscous, wax-like or solid residues on the surface of the production units and the petroleum-containing formation surrounding the well. The asphaltene residues block the pores of the formation which leads to a noticeable reduction in the production rates and, in the worst case, can make production completely impossible. Asphaltene residues on the surfaces of the production units, for example the delivery tube or the casing walls of pipelines or separators, can also considerably reduce production.
Accordingly, there are various known methods for keeping asphaltenes dispersed in crude oil and for preventing their precipitation.
DE 197 09 797 describes synergistic mixtures of alkyl phenol formaldehyde resins and certain alkoxylated amines as asphaltene dispersants. It is known from US 4,414,035 that alkyl aryl sulfonic acid derivatives, for example dodecyl benzenesulfonic acid, disperse asphaltenes in crude oils.
However, it has often been found in practice that known auxiliaries for stabilizing asphaltenes differ very considerably in their effectiveness according to the nature and origin of the crude oil. This is attributable in particular to the complex and highly variable structure of the asphaltenes.
Accordingly, efforts have been made to find new asphaltene stabilizers. In addition, known asphaltene stabilizers are often either toxic and/or ecologically unsafe. Because of this, it is preferred to avoid using them both for reasons of environmental safety and in the interests of safety at work.
Accordingly, the problem addressed by the present invention was to provide effective alternatives to the stabilizers known from the prior art for stabilizing asphaltenes in crude oils, despite very different crude oil qualities. It has been found that certain sulfonated alkyl phenol formaldehydes solve this problem.
In a first embodiment, therefore, the present invention relates to the use of products obtainable by sulfonation of compounds corresponding to formula (I) or (II):
R
R-Ph-[Ph]n Ph-R (I) R
- [Ph-CHZ-] n- (II) in which n is a number of 2 to 12 and R is a C3_2a alkyl, C6_~2 aryl or hydroxyaryl or C~_~2 aralkyl group, as stabilizers for asphaltenes in crude oil. In addition, Ph in formula(I) and (II) is a phenol residue.
The sulfonation products used in accordance with the invention are obtained by sulfonation of compounds known per se corresponding to general formulae (I) and/or (II). These starting products are known, for example, from DE 197 09 797 A1. Reference is made here to formulae (I) and (II) in claim 1 of DE 197 09 797 A1, to the disclosure on page 2, lines 40 to 44 and to the disclosure on page 3 of that document. The disclosures of those passages are specifically included in the disclosure of the present application. Formulae (I) and (II) in DE 197 09 797 are identical with those of the present application. The compounds in question are resins which are obtainable, for example, under the name of Dowfax DM 645 (Dow Chemicals).
The educts corresponding to formulae (I) and (II) are sulfonated in known manner with gaseous S03. According to the invention, however, the sulfonation products are not neutralized, but are present as free acids. The sulfonation of the educts is preferably carried out by a continuous process in a falling film reactor. The gaseous sulfur trioxide is produced in situ by pyrolysis of pure sulfur. The polyalkyl formaldehyde resin used is preferably reacted with sulfur trioxide in an equimolar ratio. The reaction itself advantageously takes place at a temperature of 75 to 80°C. The end product is preferably not neutralized. The products according to the invention are obtained in the form of aqueous solutions which may be directly formulated and used as asphaltene dispersants without any further steps. The sulfonated products surprisingly exhibit distinctly better properties as asphaltene inhibitors or asphaltene stabilizers than the compounds known from the prior art or mixtures thereof according to the teaching of DE 197 09 797 A1.
Crude oil in the context of the present invention is understood to be the unrefined petroleum coming directly from the ground. This unrefined petroleum consists of complex mixtures of, predominantly, hydrocarbons with densities of 0.65 to 1.02 g/cm3 and calorific values of 38 to 46 MJ/kg.
The boiling points of the most important constituents of crude oil are in the temperature range from 50 to 350°C (cf. Rompp, Chemielexikon, Vol. 2, 1997, pages 1210 to 1213).
The use of the sulfonated alkylphenol formaldehydes in accordance with the invention, i.e. their addition to crude oils, effectively prevents the precipitation of asphaltenes and the formation of residues. In order to prevent the precipitation of asphaltenes, it is of advantage to add the sulfonated alkylphenol formaldehydes to the crude oil in quantities of 50 to 2500 ppm, preferably in quantities of 100 to 1000 ppm and more particularly in quantities of 150 to 500 ppm (active substance).
The present invention also relates to a process for preventing the precipitation of asphaltenes from crude oils, characterized in that sulfonated alkylphenol formaldehydes corresponding to the foregoing description are added to the crude oils as stabilizers in quantities of 100 to 2500 ppm.
The present technical teaching also encompasses the use of the sulfonated alkylphenol formaldehydes in the form of dilute solutions in aromatic solvents, preferably toluene. These dilute solutions contain the polyester amides in quantities of preferably 2 to 50% by weight, more preferably 2 to 20% by weight and most preferably 2 to 15% by weight.
Corresponding formulations may also contain other additives, such as corrosion inhibitors or defoamers.
Examples Production of the sulfonation products:
The educts were sulfonated by a continuous process in a falling film reactor. The gaseous sulfur trioxide was produced in situ by pyrolysis of pure sulfur. The polyalkyl formaldehyde resin used was reacted with sulfur trioxide in an equimolar ratio. The reaction itself was carried out at a temperature of 75 to 80°C. The end product was not neutralized. The active substance content as measured by Epton titration, the molecular weight and the acid number were determined as characteristics.
Typical values for a resin based on Dowfax DM 650 are shown by way of example below:
AdditiveAcid valueMolecular weight Active substance content [glmol] [%]
Testing of the dispersing properties:
The test is based on the fact that asphaltenes are soluble in aromatic hydrocarbons, but not in aliphatic hydrocarbons. Accordingly, dispersants can be tested by dissolving the oil or extracted asphaltenes in an aromatic solvent and then adding a nonaromatic solvent to produce a deposit. Since asphaltenes are dark in color, the size of the deposit can be determined by UV-spectroscopic measurement of the supernatant liquid.
The educts were sulfonated by a continuous process in a falling film reactor. The gaseous sulfur trioxide was produced in situ by pyrolysis of pure sulfur. The polyalkyl formaldehyde resin used was reacted with sulfur trioxide in an equimolar ratio. The reaction itself was carried out at a temperature of 75 to 80°C. The end product was not neutralized. The active substance content as measured by Epton titration, the molecular weight and the acid number were determined as characteristics.
Typical values for a resin based on Dowfax DM 650 are shown by way of example below:
AdditiveAcid valueMolecular weight Active substance content [glmol] [%]
Testing of the dispersing properties:
The test is based on the fact that asphaltenes are soluble in aromatic hydrocarbons, but not in aliphatic hydrocarbons. Accordingly, dispersants can be tested by dissolving the oil or extracted asphaltenes in an aromatic solvent and then adding a nonaromatic solvent to produce a deposit. Since asphaltenes are dark in color, the size of the deposit can be determined by UV-spectroscopic measurement of the supernatant liquid.
Dispersing test - procedure a) A 20% solution of isolated asphaltenes in toluene is prepared;
b) 9.5 ml heptane as precipitant for asphaltenes, 0.5 ml of the asphaltene solution in toluene and the corresponding quantity of dispersant solution for the required concentration are mixed and thoroughly shaken in a 10 ml graduated glass tube;
c) a test tube without any dispersant solution is prepared as a negative sample and the solvent heptane is replaced by toluene as a positive sample; two commercial products (Anticor DSA 800 and 711 ) were included in the tests for further comparison;
d) the test tubes were observed for 3 hours and the precipitation time of the asphaltenes was recorded, the sediment collecting at the bottom of the test tubes;
g) evaluation of the sediment volume and appearance of the solution was carried out in comparison with the positive and negative samples. Evaluation of the sediment volume was based on a scale of 1 to 3 where 3 represents the largest volume.
The results of the precipitation tests at three concentrations of various formulations A to H according to the invention are set out in the following Table.
Formulation 100 ppm 500 ppm 1000 ppm Negative sampleT = 30 mins T = 30 mins T = 30 mins.
SV=3 SV=3 SV=3 A No SV No SV No SV
B No SV No SV T = 30 mins.
SV=2 C No SV No SV T = 30 mins.
SV = 2 D No SV No SV No SV
E No SV No SV No SV
F ~ NoSV ~oSV NoSV
b) 9.5 ml heptane as precipitant for asphaltenes, 0.5 ml of the asphaltene solution in toluene and the corresponding quantity of dispersant solution for the required concentration are mixed and thoroughly shaken in a 10 ml graduated glass tube;
c) a test tube without any dispersant solution is prepared as a negative sample and the solvent heptane is replaced by toluene as a positive sample; two commercial products (Anticor DSA 800 and 711 ) were included in the tests for further comparison;
d) the test tubes were observed for 3 hours and the precipitation time of the asphaltenes was recorded, the sediment collecting at the bottom of the test tubes;
g) evaluation of the sediment volume and appearance of the solution was carried out in comparison with the positive and negative samples. Evaluation of the sediment volume was based on a scale of 1 to 3 where 3 represents the largest volume.
The results of the precipitation tests at three concentrations of various formulations A to H according to the invention are set out in the following Table.
Formulation 100 ppm 500 ppm 1000 ppm Negative sampleT = 30 mins T = 30 mins T = 30 mins.
SV=3 SV=3 SV=3 A No SV No SV No SV
B No SV No SV T = 30 mins.
SV=2 C No SV No SV T = 30 mins.
SV = 2 D No SV No SV No SV
E No SV No SV No SV
F ~ NoSV ~oSV NoSV
Formulation 100 ppm 500 ppm 1000 ppm G T = 45 mins. No SV No SV
SV=1 H No SV No SV No SV
Positive sam No SV No SV No SV
le Anticor DSA T = 2 h T =16 h No SV
800 T=1-2 SV=1 Anticor DSA T = 60 mina. T =16 h No SV
711 SV=2 SV=1 Table 1:
Asphaltene test for various formulations T = precipitation time, SV = sediment volume (3 = maximum) In order to be able to compare the results of the spectroscopic analysis, the absorption values of the experimental formulations were divided by the corresponding value of the positive sample (pure toluene) -shown in the Tables as relative absorption. The nearer the values are to 1.0, the better the effect of the dispersant formulation. The values are set out in the following Table.
Formulation 100 ppm 500 ppm 1000 ppm A 0.81 0.85 0.86 B 0.79 0.81 0.72 C 0.76 0.79 0.73 D 085 0.87 0.89 E 0.84 0.82 0.86 F 0.79 0.80 0.84 G 0.76 0.79 0.83 H 0.82 0.86 0.87 Positive sam 1 1 1 le Anticor DSA 0.74 0.76 0.78 Anticor DSA 0.75 0.78 0.78 Table 2:
Relative absorption values of the asphaltene solutions
SV=1 H No SV No SV No SV
Positive sam No SV No SV No SV
le Anticor DSA T = 2 h T =16 h No SV
800 T=1-2 SV=1 Anticor DSA T = 60 mina. T =16 h No SV
711 SV=2 SV=1 Table 1:
Asphaltene test for various formulations T = precipitation time, SV = sediment volume (3 = maximum) In order to be able to compare the results of the spectroscopic analysis, the absorption values of the experimental formulations were divided by the corresponding value of the positive sample (pure toluene) -shown in the Tables as relative absorption. The nearer the values are to 1.0, the better the effect of the dispersant formulation. The values are set out in the following Table.
Formulation 100 ppm 500 ppm 1000 ppm A 0.81 0.85 0.86 B 0.79 0.81 0.72 C 0.76 0.79 0.73 D 085 0.87 0.89 E 0.84 0.82 0.86 F 0.79 0.80 0.84 G 0.76 0.79 0.83 H 0.82 0.86 0.87 Positive sam 1 1 1 le Anticor DSA 0.74 0.76 0.78 Anticor DSA 0.75 0.78 0.78 Table 2:
Relative absorption values of the asphaltene solutions
Claims (5)
1. The use of products obtainable by sulfonation of compounds corresponding to formula (I) or (II):
in which Ph is a phenol residue, n is a number of 2 to 12 and R is a C3-24 alkyl, C6-12 aryl or hydroxyaryl or C7-12 aralkyl group, as stabilizers for asphaltenes in crude oil.
in which Ph is a phenol residue, n is a number of 2 to 12 and R is a C3-24 alkyl, C6-12 aryl or hydroxyaryl or C7-12 aralkyl group, as stabilizers for asphaltenes in crude oil.
2. The use claimed in claim 1, characterized in that the compounds of formula (I) and/or (II) are added to the crude oils in quantities of 50 to ppm, preferably in quantities of 100 to 1000 ppm and more particularly in quantities of 150 to 500 ppm.
3. A process for preventing the precipitation of asphaltenes in crude oils, characterized in that the sulfonated compounds according to claim 1 are added to the crude oils as stabilizers in quantities of 100 to 2500 ppm.
4. Sulfonated alkylphenol formaldehyde resins, characterized in that they are obtained by sulfonation of the compounds of formulae (I) and/or (II) in claim 1.
5. A process for the production of sulfonated alkylphenol formaldehyde resins in which the compounds of formulae (I) and/or (II) in claim 1 are reacted in an equimolar ratio with gaseous SO3 in a falling film reactor at temperatures of 75 to 80°C, characterized in that the reaction products are not neutralized.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10163244.4 | 2001-12-21 | ||
| DE10163244A DE10163244A1 (en) | 2001-12-21 | 2001-12-21 | Use of sulfonated alkylphenol formaldehydes to stabilize asphaltenes in crude oil |
| PCT/EP2002/014127 WO2003054348A1 (en) | 2001-12-21 | 2002-12-12 | Use of sulphonated alkyl phenol formaldehydes in the stabilization of ashphaltenes in crude oil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2471413A1 true CA2471413A1 (en) | 2003-07-03 |
Family
ID=7710367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002471413A Abandoned CA2471413A1 (en) | 2001-12-21 | 2002-12-12 | Use of sulphonated alkyl phenol formaldehydes in the stabilization of ashphaltenes in crude oil |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20050091915A1 (en) |
| EP (1) | EP1458951A1 (en) |
| BR (1) | BR0215153A (en) |
| CA (1) | CA2471413A1 (en) |
| DE (1) | DE10163244A1 (en) |
| WO (1) | WO2003054348A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102584641B (en) * | 2011-12-14 | 2013-12-04 | 中国日用化学工业研究院 | Process for preparing alkylphenol formaldehyde oligomer sulfonate |
| US9921205B2 (en) | 2012-11-13 | 2018-03-20 | Chevron U.S.A. Inc. | Method for determining the effectiveness of asphaltene dispersant additives for inhibiting or preventing asphaltene precipitation in a hydrocarbon-containing material subjected to elevated temperature and presssure conditions |
| US9523054B2 (en) | 2013-08-21 | 2016-12-20 | Baker Hughes Incorporated | Asphaltene stabilization in petroleum feedstocks by blending with biological source oil and/or chemical additive |
| CN108290876A (en) * | 2015-11-30 | 2018-07-17 | Bp北美公司 | Screening technique for asphalitine stabilizer |
| US10907473B2 (en) | 2017-11-14 | 2021-02-02 | Chevron U.S.A., Inc. | Low volume in-line filtration methods for analyzing hydrocarbon-containing fluid to evaluate asphaltene content and behavior during production operations |
| US20240117238A1 (en) | 2022-09-28 | 2024-04-11 | Championx Llc | Extended release asphaltene inhibitor composition |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2639227A (en) * | 1950-09-02 | 1953-05-19 | Shell Dev | Anticlogging fuel oil compositions |
| US3872056A (en) * | 1974-01-14 | 1975-03-18 | Ewald Daubach | Manufacture of phenol/formaldehyde resins |
| US4414035A (en) * | 1979-05-21 | 1983-11-08 | Petrolite Corporation | Method for the removal of asphaltenic deposits |
| DE3538910A1 (en) * | 1985-11-02 | 1987-05-14 | Henkel Kgaa | METHOD FOR PRODUCING MOVABLE PASTE OF WASHING ACTIVE ALPHA SULFOURIC ACID ESTER SALTS HIGH SOLIDS |
| DE3803110A1 (en) * | 1988-02-03 | 1989-08-17 | Hoechst Ag | METHOD FOR PRODUCING SULFATED ALKANOL OR ALKYLPHENOL OXETHYLATES WITH A LOW CONTENT OF 1,4-DIOXANE |
| US20020091069A1 (en) * | 1996-11-26 | 2002-07-11 | William F. King | Overbased alkyl oxy benzene sulfonates as detergents |
| DE19709797A1 (en) * | 1997-03-10 | 1998-09-17 | Clariant Gmbh | Synergistic mixtures of alkylphenol formaldehyde resins with oxalkylated amines as asphaltene dispersants |
| US6048904A (en) * | 1998-12-01 | 2000-04-11 | Exxon Research And Engineering Co. | Branched alkyl-aromatic sulfonic acid dispersants for solublizing asphaltenes in petroleum oils |
-
2001
- 2001-12-21 DE DE10163244A patent/DE10163244A1/en not_active Withdrawn
-
2002
- 2002-12-12 EP EP02798329A patent/EP1458951A1/en not_active Withdrawn
- 2002-12-12 US US10/499,765 patent/US20050091915A1/en not_active Abandoned
- 2002-12-12 BR BR0215153-7A patent/BR0215153A/en not_active IP Right Cessation
- 2002-12-12 WO PCT/EP2002/014127 patent/WO2003054348A1/en not_active Application Discontinuation
- 2002-12-12 CA CA002471413A patent/CA2471413A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003054348A1 (en) | 2003-07-03 |
| EP1458951A1 (en) | 2004-09-22 |
| BR0215153A (en) | 2004-10-19 |
| US20050091915A1 (en) | 2005-05-05 |
| DE10163244A1 (en) | 2003-07-10 |
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