CN111440093A - Preparation method of alkylbenzene sulfonate for binary composite flooding oil recovery - Google Patents
Preparation method of alkylbenzene sulfonate for binary composite flooding oil recovery Download PDFInfo
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- CN111440093A CN111440093A CN202010375659.0A CN202010375659A CN111440093A CN 111440093 A CN111440093 A CN 111440093A CN 202010375659 A CN202010375659 A CN 202010375659A CN 111440093 A CN111440093 A CN 111440093A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
- C07C2/68—Catalytic processes with halides
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
- C07C309/32—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings containing at least two non-condensed six-membered aromatic rings in the carbon skeleton
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- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
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- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
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Abstract
The invention discloses a preparation method of alkylbenzene sulfonate for binary composite flooding oil recovery, which comprises the following steps of firstly, taking diphenylmethane as a raw material, taking palladium chloride as a catalyst, and reacting with hexadecane/octadecylene to obtain corresponding alkylbenzene, wherein the reaction does not need a solvent, and the diphenylmethane can be changed into a liquid state by heating and used as the solvent; then, taking alkylbenzene as a raw material, sulfonating sulfur trioxide gas in a falling film reactor, aging after sulfonation, and neutralizing with a sodium hydroxide solution to obtain corresponding alkylbenzene sulfonate; the invention has good effect, good application prospect and popularization value.
Description
Technical Field
The invention relates to the technical field of oil exploitation, in particular to a preparation method of alkylbenzene sulfonate for binary composite flooding oil extraction.
Background
With the large-scale application of tertiary oil recovery, the role of sulfonate in tertiary oil recovery is obvious. In tertiary oil recovery, substances such as sulfonate, polymer, alkali and the like are added to reduce viscosity, reduce interfacial tension and improve the sweep coefficient of injection liquid, so that the aims of increasing the number of capillary tubes, improving the wettability of the surface of stratum rock, improving the dispersibility of crude oil and changing the rheological property of the crude oil are achieved, and the recovery ratio of the crude oil is improved.
The ternary combination flooding is a new technology for enhanced oil recovery developed in 80 s of 20 th century, and is an oil displacement technology formed by utilizing a mixture of three compounds of alkali, surfactant and polymer. Through the reduction of interfacial tension and the large spread range of alkali, the addition of the polymer is beneficial to the control of fluidity, the finger advance of a composite system is reduced, the spread volume is enlarged, and a plurality of triple-displacement mine field experiments are carried out in Daqing oil fields and Shengli oil fields, so that a good effect is achieved. The technology has the characteristics of small dosage of the active agent, high oil displacement efficiency and the like, and greatly reduces the high cost brought by surface active agent displacement. However, some problems are also exposed in the development, such as scaling prevention and produced fluid demulsification, and a certain amount of alkali is also added, and because a large amount of alkali is adsorbed in the stratum, the pore passages of the stratum are blocked, so that the stratum structure is damaged, and great difficulty is brought to further production.
The binary combination flooding is used as a new oil displacement method, can well overcome some defects of ternary flooding, and a binary system of a surfactant polymer can exert the viscoelasticity of the polymer to the maximum extent, reduce the negative effects caused by emulsion and thoroughly eliminate the scaling problem. However, the binary combination flooding also has the problems of poor performance of reducing interfacial tension, few performance researches of a polymer system, insufficient micro seepage exploration and the like, so that the development of a novel sulfonate surfactant is still needed.
The sulfonates currently used in tertiary oil recovery are mainly heavy alkylbenzene sulfonates and petroleum sulfonates, which are a class of benzene sulfonates containing 16 to 24 carbon chain lengths and have been found to have excellent surface tension-reducing properties through studies, and heavy alkylbenzene sulfonates are currently used as important surfactants in tertiary oil recovery. Petroleum sulfonateThe petroleum sulfonate is also obtained by directly sulfonating the petroleum sulfonate petroleum crude oil which is more than the sulfonate used for tertiary oil recovery at present and is obtained by reducing the oil content of two or three lines, has complex components, is similar to the original structure, has low production cost and is more in current application, but the petroleum sulfonate can only reduce the oil/water interfacial tension to l × 10-2The mN/m order of magnitude can not meet the requirement of ultra-low oil-water interfacial tension required by oil displacement, and the application of petroleum sulfonate in binary combination flooding is greatly limited.
So far, the sulfonate anionic active agents used in binary combination flooding are very few in types. CN01144907.1 alkylbenzene sulfonate surfactant, its preparation and application in tertiary oil recovery select heavy alkylbenzene as raw material, carry on sulfonation to get alkylbenzene sulfonic acid and mixture of sulfuric acid, divide acid to get intermediate product alkylbenzene sulfonic acid, get alkylbenzene sulfonate while carrying on neutralization, get final product alkylbenzene sulfonate surfactant after compounding. The technical proposal of the method is different from the preparation steps proposed by the inventor. A preparation method of a gemini long-chain alkyl sulfonate oil-displacing agent with Chinese patent publication number of CN101684405A (Wangyu), wherein N, N-dimethylformamide and the like are used as raw materials to prepare the gemini long-chain alkyl sulfonate oil-displacing agent, and a preparation method of an asymmetric gemini oil-displacing agent for oil extraction with Chinese patent publication number of 101659860A (Chengning) and an asymmetric gemini sulfonate oil-displacing agent are prepared; CN00120947.7 ternary complex composition containing alkylbenzene sulfonate surfactant and its application, the adopted system is alkylbenzene sulfonate surfactant-alkali or composite alkali-polymer ternary drive system, its component content is:
0.1 to 0.3 portion of alkylbenzene sulfonate
1.0-1.4 parts of alkali or compound alkali
0.08-0.15 part of polymer
Different from the technical scheme provided by the inventor, the steps are also different.
CN99106077.6 alkylbenzene sulfonate surfactant, its preparation method and its application in tertiary oil recovery are that heavy alkylbenzene is used as raw material to make sulfonation to obtain intermediate alkylbenzene sulfonate and make neutralization to obtain alkylbenzene sulfonate. The technical proposal of the method is different from the preparation steps proposed by the inventor.
The method for preparing the sulfonate, which is proposed by the above patents, has the disadvantages of rigorous preparation process requirements, more reaction steps and difficult industrialization. In order to better overcome the defects of the ternary combination flooding in the production process and meet the requirements of the binary combination flooding, the invention develops a novel alkylbenzene sulfonate for the application of the binary combination flooding and further improves the recovery ratio.
Disclosure of Invention
The invention aims to provide a preparation method of alkylbenzene sulfonate for binary composite flooding oil recovery, which mainly comprises the steps of alkylating diphenylmethane and hexadecahtadecadecene to synthesize hexadecahtadecaalkylbenzene, sulfonating the obtained alkylbenzene and sulfur trioxide gas, aging, and neutralizing by sodium hydroxide to obtain the required 2-benzyl-hexadecahtadecaalkylbenzene sulfonate. The invention designs novel 2-benzyl-hexadecyl/octadecyl benzene to further obtain corresponding alkylbenzene sulfonate. The 2-benzyl-hexadecyl/octadecyl benzene sulfonate related by the invention is good in effect for the first time, and has good application prospect and popularization value.
In order to achieve the purpose, the invention provides the following technical scheme:
a preparation method of alkylbenzene sulfonate for binary composite flooding oil recovery comprises the steps of firstly, taking diphenylmethane as a raw material, taking palladium chloride as a catalyst, and reacting with hexadecane/octadecylene to obtain corresponding alkylbenzene, wherein the reaction does not need a solvent, and the diphenylmethane can be changed into a liquid state by heating and used as the solvent; and then, taking alkylbenzene as a raw material, sulfonating sulfur trioxide gas in a falling film reactor, aging after sulfonation, and neutralizing with a sodium hydroxide solution to obtain the corresponding alkylbenzene sulfonate.
The catalyst is one or more of 5% of chlorination catalyst, 5% of ferric chloride catalyst, 5% of aluminum chloride catalyst and 5% of zinc chloride catalyst.
The olefin is hexadecene/octadecylene, hexadecene, octadecene, 20-24 ene, dodecene and tetradecene.
The reaction temperature of the alkylation is 60-120 ℃.
The reaction time of the alkylation is 10-12 h.
The collection distillation temperature of the vacuum distillation after the alkylation treatment is 340-420 ℃.
The circulating water temperature of the falling film reactor during the sulfonation reaction is 40-60 ℃.
The concentration of sulfur trioxide gas during sulfonation is 3-6%.
The flow rate of the alkylbenzene during sulfonation is 30-40L/h.
The aging time after sulfonation is 2-4 h.
The concentration of the sodium hydroxide solution during neutralization is 30-40%.
The invention has the beneficial effects
The interfacial tension of a binary composite system obtained by compounding the novel alkylbenzene sulfonate obtained by the reaction reaches 10-4The mN/m is an order of magnitude, the good capability of reducing interfacial tension is shown, the viscosity reduction effect on thick oil is good, the salt resistance and high temperature resistance are good, and the performance is superior to that of the currently used heavy alkylbenzene sulfonate and petroleum sulfonate.
Detailed Description
The technical solution of the present patent will be described in further detail with reference to the following embodiments.
Example 1:
step 1, accurately weighing 200kg of diphenylmethane and 10kg of palladium chloride catalyst, adding the diphenylmethane and the palladium chloride catalyst into a 1000L reaction kettle, and heating;
step 2, stirring is started when the temperature of the diphenylmethane in the step 1 is increased to 60 ℃, and after the temperature is continuously increased to 120 ℃, heat preservation and stirring are carried out;
step 3, adding 300kg of hexadecane/octadecane mixed alkene into the step 2 for reaction;
step 4, keeping the reaction of the step 3 at 120 ℃, and reacting for 10 hours to ensure that the alkylation reaction can be completely carried out;
stirring and cooling the reactants in the step 3, and discharging after the reactants are cooled to room temperature;
and (3) carrying out reduced pressure distillation on the material in the step (3), and collecting the fraction at 340-420 ℃ to obtain the alkylbenzene.
Step 5, carrying out sulfonation reaction on the alkylbenzene obtained in the step 4, wherein the concentration of the introduced sulfur trioxide gas is 5%, the circulating water temperature of the falling-film reactor is controlled to be 50-60 ℃, and the material flow rate is 40L/h, so that corresponding alkylbenzene sulfonic acid can be obtained;
and 6, detecting the aging of the alkylbenzene sulfonic acid obtained in the step 5 for 3 hours.
And 7, detecting the alkylbenzene sulfonic acid obtained in the step 6, neutralizing with 40% sodium hydroxide, and neutralizing until the pH value is 7 to obtain the corresponding alkylbenzene sulfonate.
Sample detection, wherein the crude product in the step 7, crude oil and sewage samples of Tuha oil field and relative molecular mass of 2.5 × 107The polyacrylamide is compounded into a binary flooding crude oil system containing 0.3 percent of alkylbenzene sulfonate.
Crude oil data:
sewage data:
nature of sewage (PH 7)
The interfacial tension surface tension is measured by a TX-500C type interfacial tension surface tensiometer of the American Biaowei company
The interfacial tension is 1.1 × 10 measured at 40 ℃ and 5000r/min-4mN/m。
Example 2:
step 1, accurately weighing 200kg of diphenylmethane and 10kg of ferric chloride catalyst, adding the diphenylmethane and the ferric chloride catalysts into a 1000L reaction kettle, and heating.
And 2, starting stirring when the temperature of the diphenylmethane in the step 1 is increased to 60 ℃, continuously heating to 120 ℃, and keeping the temperature and stirring.
And 3, adding 300kg of sixteen/eighteen mixed alkene into the mixture obtained in the step 2.
Step 4, the reaction in the step 3 is kept at 120 ℃ for 10 hours, so that the alkylation reaction can be completely carried out;
stirring and cooling the reactants in the step 3, and discharging after the reactants are cooled to room temperature;
and (3) carrying out reduced pressure distillation on the material in the step (3), and collecting the fraction at 340-420 ℃ to obtain the alkylbenzene.
Step 5, carrying out sulfonation reaction on the alkylbenzene obtained in the step 4, controlling the concentration of the introduced sulfur trioxide gas to be 5%, controlling the circulating water temperature of the falling-film reactor to be 50-60 ℃ and the material flow rate to be 40L/h, thus obtaining corresponding alkylbenzene sulfonic acid,
and 6, detecting the aging of the alkylbenzene sulfonic acid obtained in the step 5 for 3 hours.
And 7, detecting the alkylbenzene sulfonic acid obtained in the step 6, neutralizing with 40% sodium hydroxide, and neutralizing until the pH value is 7 to obtain the corresponding alkylbenzene sulfonate.
The measurement method is the same as that of example 1, and the interfacial tension of the obtained novel alkylbenzene sulfonate binary composite flooding is 2.1 × 10-4mN/m。
Example 3:
step 1, accurately weighing 200kg of diphenylmethane and 10kg of aluminum chloride catalyst, adding the diphenylmethane and the aluminum chloride catalysts into a 1000L reaction kettle, and heating.
And 2, starting stirring when the temperature of the diphenylmethane in the step 1 is increased to 60 ℃, continuously heating to 120 ℃, and keeping the temperature and stirring.
And 3, adding 300kg of hexadecene into the mixture obtained in the step 2.
And 4, keeping the reaction of the step (3) at 120 ℃ for 10 hours so that the alkylation reaction can be completely carried out.
And (4) stirring and cooling the reactants in the step (3), and discharging after the reactants are cooled to room temperature.
And (4) carrying out reduced pressure distillation on the material in the step (3), and collecting the fraction at 340-420 ℃ to obtain the alkylbenzene.
And 5, carrying out sulfonation reaction on the alkylbenzene obtained in the step 4, wherein the concentration of the introduced sulfur trioxide gas is 5%, the circulating water temperature of the falling-film reactor is controlled at 50-60 ℃, and the material flow rate is 40L/h.
And 6, detecting the aging of the alkylbenzene sulfonic acid obtained in the step 5 for 3 hours.
And 7, detecting the alkylbenzene sulfonic acid obtained in the step 6, neutralizing with 40% sodium hydroxide, and neutralizing until the pH value is 7 to obtain the corresponding alkylbenzene sulfonic acid salt.
The measurement method is the same as that of example 1, and the interfacial tension of the obtained novel alkylbenzene sulfonate binary composite flooding is 1.6 × 10-4mN/m。
Example 4:
step 1, accurately weighing 200kg of diphenylmethane and 10kg of palladium chloride catalyst, adding the diphenylmethane and the palladium chloride catalyst into a 1000L reaction kettle, and heating.
And 2, starting stirring when the temperature of the diphenylmethane in the step 1 is increased to 60 ℃, continuously heating to 120 ℃, and keeping the temperature and stirring.
And 3, adding 300kg of octadecene into the step (2) for reaction.
Step 4, keeping the reaction of the step (3) at 120 ℃ for reacting for 10 hours, so that the alkylation reaction can be completely carried out;
and (4) stirring and cooling the reactants in the step (3), and discharging after the reactants are cooled to room temperature.
And (4) carrying out reduced pressure distillation on the material in the step (3), and collecting the fraction at 340-420 ℃ to obtain the alkylbenzene.
And 5, carrying out sulfonation reaction on the alkylbenzene obtained in the step 4, wherein the concentration of the introduced sulfur trioxide gas is 5%, the circulating water temperature of the falling-film reactor is controlled at 50-60 ℃, and the material flow rate is 40L/h.
And 6, detecting the aging of the alkylbenzene sulfonic acid obtained in the step 5 for 3 hours.
And 7, detecting the alkylbenzene sulfonic acid obtained in the step 6, neutralizing with 40% sodium hydroxide, and neutralizing until the pH value is 7 to obtain the corresponding alkylbenzene sulfonic acid salt.
The measurement method is the same as that of example 1, and the interfacial tension of the obtained novel alkylbenzene sulfonate binary composite flooding is 1.3 × 10-4mN/m。
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Furthermore, it should be understood that although the present description refers to embodiments, not every embodiment may contain only a single embodiment, and such description is for clarity only, and those skilled in the art should integrate the description, and the embodiments may be combined as appropriate to form other embodiments understood by those skilled in the art.
Claims (10)
1. A preparation method of alkylbenzene sulfonate for binary composite flooding oil extraction is characterized by comprising the following specific steps:
step 1, accurately weighing diphenylmethane, adding a palladium chloride catalyst into a reaction kettle, and heating;
step 2, when the temperature of the diphenylmethane in the step 1 is increased to the temperature, stirring, continuously heating, and keeping the temperature and stirring;
step 3, adding hexadecane/octadecene into the step 2 for reaction;
step 4, the alkylation reaction in the step 3 can be completely carried out;
stirring and cooling the reactants in the step 3, and discharging after the reactants are cooled to room temperature;
carrying out reduced pressure distillation on the material in the step 3, and collecting fractions to obtain alkylbenzene;
step 5, carrying out sulfonation reaction on the alkylbenzene obtained in the step 4, wherein the concentration of the introduced sulfur trioxide gas is 5%, the circulating water temperature of the falling-film reactor is controlled to be 50-60 ℃, and the material flow rate is 40L/h, so that corresponding alkylbenzene sulfonic acid can be obtained;
step 6, detecting the aging of the alkylbenzene sulfonic acid obtained in the step 5 for 3 hours;
and 7, detecting the alkylbenzene sulfonic acid obtained in the step 6, neutralizing with 40% sodium hydroxide, and neutralizing until the pH value is 7 to obtain the corresponding alkylbenzene sulfonate.
2. The method for preparing alkylbenzene sulfonate for binary combination flooding oil recovery according to claim 1, wherein the catalyst is one or more of 5% chlorination catalyst, 5% ferric chloride catalyst, 5% aluminum chloride catalyst and 5% zinc chloride catalyst.
3. The method for preparing alkylbenzene sulfonate for binary composite flooding oil recovery according to claim 1, wherein the hexadecene/octadecylene can be replaced by any one of hexadecene, octadecene, 20-24 olefin, dodecene and tetradecene.
4. The process of claim 1, wherein the alkylation reaction temperature is 60-120 deg.C, and the alkylation reaction time is 10-12 h.
5. The method for preparing alkylbenzene sulfonate for binary composite flooding oil recovery as claimed in claim 1, wherein the collection distillation temperature of vacuum distillation after alkylation is 340-420 ℃.
6. The method for preparing alkylbenzene sulfonate for binary composite flooding oil recovery according to claim 1, wherein the temperature of circulating water in the falling film reactor during sulfonation reaction is 40-60 ℃.
7. The method for preparing alkylbenzene sulfonate for binary combination flooding oil recovery according to claim 1, wherein the concentration of sulfur trioxide gas during sulfonation is 3-6%.
8. The process of claim 1, wherein the alkylbenzene sulfonate for binary composite flooding oil recovery has a flow rate of 30-40L/h.
9. The method for preparing alkylbenzene sulfonate for binary composite flooding oil recovery according to claim 1, wherein the aging time after sulfonation is 2-4 h.
10. The method for preparing alkylbenzene sulfonate for binary composite flooding oil recovery according to claim 1, wherein the concentration of sodium hydroxide solution during neutralization is 30-40%.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117049985A (en) * | 2023-08-11 | 2023-11-14 | 安徽金桐精细化学有限公司 | High-carbon sodium alkylbenzenesulfonate and preparation method and application thereof |
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| CN117049985A (en) * | 2023-08-11 | 2023-11-14 | 安徽金桐精细化学有限公司 | High-carbon sodium alkylbenzenesulfonate and preparation method and application thereof |
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Application publication date: 20200724 |