CN116283670B - Thickened oil viscosity reducer and preparation method thereof - Google Patents
Thickened oil viscosity reducer and preparation method thereof Download PDFInfo
- Publication number
- CN116283670B CN116283670B CN202310260090.7A CN202310260090A CN116283670B CN 116283670 B CN116283670 B CN 116283670B CN 202310260090 A CN202310260090 A CN 202310260090A CN 116283670 B CN116283670 B CN 116283670B
- Authority
- CN
- China
- Prior art keywords
- viscosity reducer
- oil viscosity
- thick oil
- dodecyloxy
- benzaldehyde
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000003638 chemical reducing agent Substances 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 66
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 28
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims abstract description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000007787 solid Substances 0.000 claims abstract description 20
- QPAKGKFSBBAHMS-UHFFFAOYSA-N 2,6-didodecoxybenzaldehyde Chemical compound CCCCCCCCCCCCOC1=CC=CC(OCCCCCCCCCCCC)=C1C=O QPAKGKFSBBAHMS-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000010992 reflux Methods 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000000243 solution Substances 0.000 claims abstract description 16
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 235000019253 formic acid Nutrition 0.000 claims abstract description 14
- 238000010438 heat treatment Methods 0.000 claims abstract description 14
- AKTHLFYZKHPYBY-UHFFFAOYSA-M sodium;1-chloroethanesulfonate Chemical compound [Na+].CC(Cl)S([O-])(=O)=O AKTHLFYZKHPYBY-UHFFFAOYSA-M 0.000 claims abstract description 14
- 229960003080 taurine Drugs 0.000 claims abstract description 14
- 239000008367 deionised water Substances 0.000 claims abstract description 12
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000001816 cooling Methods 0.000 claims abstract description 10
- 230000001105 regulatory effect Effects 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 9
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- 239000003208 petroleum Substances 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 6
- 230000008569 process Effects 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000001308 synthesis method Methods 0.000 abstract description 2
- 239000003921 oil Substances 0.000 description 45
- 230000009467 reduction Effects 0.000 description 28
- 235000011121 sodium hydroxide Nutrition 0.000 description 18
- 239000010779 crude oil Substances 0.000 description 12
- 239000012295 chemical reaction liquid Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 6
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 4
- 239000000295 fuel oil Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 230000001804 emulsifying effect Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 238000010793 Steam injection (oil industry) Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C303/22—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 from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
-
- 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
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of petroleum exploitation, and particularly relates to a thick oil viscosity reducer and a synthesis method thereof. The preparation method comprises the following steps: sequentially adding 2, 6-bis (dodecyloxy) benzaldehyde, 2-aminoethanesulfonic acid, 30wt% formic acid aqueous solution and deionized water into a four-neck flask with a condenser tube, heating and refluxing, cooling to below 40 ℃, transferring the reaction solution into a rotary evaporator, and distilling under reduced pressure to obtain a brown yellow oily substance; transferring the oily substance into a four-necked flask by using 95wt% ethanol, regulating the pH value to 9-10 by using 2mol/L sodium hydroxide solution, adding sodium chloroethanesulfonate, heating and refluxing, maintaining the pH value to 9-10 by using 2mol/L sodium hydroxide during the reaction period, and distilling under reduced pressure to obtain a viscous brown solid; and (3) recrystallizing with cyclohexane to obtain a light yellow solid, namely the thick oil viscosity reducer. The thick oil viscosity reducer has the advantages of simple synthesis process, low consumption and good effect.
Description
Technical Field
The invention belongs to the technical field of petroleum exploitation, and particularly relates to a thick oil viscosity reducer and a synthesis method thereof.
Background
Thickened oil resources account for a significant proportion of world oil and gas resources. The thick oil is also called as heavy crude oil, and has the characteristics of high density, high viscosity, high flow resistance, difficult exploitation and the like. The thick oil occupies a considerable proportion in world oil gas resources, and the thick oil in China occupies about 30% of crude oil reserves, thus being an important strategic resource. With the continuous reduction of low-viscosity easy-to-recover crude oil, high-viscosity thick oil recovery is increasingly gaining importance.
The current common viscosity reduction methods used in the thick oil exploitation process at home and abroad mainly comprise heating viscosity reduction, hydrothermal cracking viscosity reduction, microorganism viscosity reduction and chemical viscosity reduction. The chemical viscosity reduction mainly adopts a water-soluble emulsifying viscosity reducer, on one hand, under the action of the water-soluble emulsifying viscosity reducer, a low-viscosity O/W emulsion is formed, and the internal friction between oil and oil is converted into the friction between water and water, so that the viscosity of thick oil is greatly reduced; on the other hand, the viscosity reducer can reversely change the interface lipophilicity into hydrophilicity to form a continuous water film, so that the flow resistance of the thickened oil is reduced.
CN1221650 discloses a surfactant mainly used for viscosity reduction of thick oil in oil field, its formula contains (by weight) lignin 15-20%, caustic soda 5-15%, soap powder 2-8% or soap 1-6%, synthetic detergent 10-15% and water the rest. The surfactant has cheap and easily available raw materials, simple preparation method, viscosity reduction rate of more than 95 percent, and no performance reduction especially under the condition of high temperature of more than 300 ℃. However, in the use process, 5-15% of caustic soda is usually required to be compounded, so that the high-viscosity-reducing emulsion has a good emulsifying and viscosity-reducing effect on thick oil, and the addition of alkaline substances can bring the adverse effects of difficult later demulsification, crude oil deep processing and the like.
CN1115778 discloses a viscosity reducer and a preparation method thereof, the molecular formula of the viscosity reducer is: (X-CH 2-X)m3-CH2-Y-CH2 -Z, wherein m 3 =3-10, the molecular formulas of X and Y, Z are respectively that the agent is injected in the steam injection exploitation of thick oil in an oil field, the temperature resistance is up to 320 ℃, the agent is stable and not decomposed, the viscosity reduction rate is up to 98%, and the requirement of oil field production is met.
Disclosure of Invention
Aiming at the problems of thick oil viscosity reduction in crude oil exploitation in China at present, the invention provides the thick oil viscosity reducer and the preparation method thereof, and the thick oil viscosity reducer has the advantages of simple synthesis process, low dosage and good effect.
The invention discloses a thick oil viscosity reducer, which has the following molecular structural formula:
The invention also aims to provide a preparation method of the thick oil viscosity reducer, which specifically comprises the following steps:
(1) Sequentially adding 2, 6-bis (dodecyloxy) benzaldehyde, 2-aminoethanesulfonic acid, 30wt% formic acid aqueous solution and deionized water into a four-neck flask with a condenser tube, heating and refluxing, cooling to below 40 ℃, transferring the reaction solution into a rotary evaporator, and distilling under reduced pressure to obtain a brown yellow oily substance;
(2) Transferring the oily substance into a four-necked flask by using 95wt% ethanol, regulating the pH value to 9-10 by using 2mol/L sodium hydroxide solution, adding sodium chloroethanesulfonate, heating and refluxing, maintaining the pH value to 9-10 by using 2mol/L sodium hydroxide during the reaction period, and distilling under reduced pressure to obtain a viscous brown solid;
(3) And (3) recrystallizing with cyclohexane to obtain a light yellow solid, namely the thick oil viscosity reducer.
In the present invention, preferably, the 2-aminoethanesulfonic acid, formic acid, sodium chloroethanesulfonate are used in an amount of 0.8 to 1.2 molar parts, 1 to 3 molar parts, 0.8 to 1.2 molar parts, respectively, based on 1 molar part of 2, 6-bis (dodecyloxy) benzaldehyde; more preferably, the 2-aminoethanesulfonic acid, formic acid, and sodium chloroethanesulfonate are used in an amount of 0.9 to 1.1 mole parts, 2 to 3 mole parts, and 0.9 to 1.1 mole parts, respectively, based on 1 mole part of 2, 6-bis (dodecyloxy) benzaldehyde.
Preferably, in the step (1), the mass ratio of the deionized water to the 2, 6-bis (dodecyloxy) benzaldehyde is 4-6:1.
Preferably, in step (1), the reflux time is 1-3 hours.
Preferably, in the step (1), the mass ratio of the ethanol to the 2, 6-bis (dodecyloxy) benzaldehyde is 10-20:1.
Preferably, in the step (2), the reflux time is 6-12h.
The reaction equation for synthesizing the thick oil viscosity reducer is as follows:
the thick oil viscosity reducer integrally belongs to a low-molecular anionic surfactant, the hydrophilic functional group is 2 sulfonic groups, tertiary amine in the molecule presents certain cationic property, but is weaker, the viscosity reducer also belongs to hydrophilic groups, and the lipophilic group comprises benzene rings and 2 long-chain dodecyl groups; compared with the conventional surfactant with single hydrophilic and lipophilic groups, the surfactant has higher surface activity and lower critical micelle concentration, so that the dosage is lower during use; the benzene ring and 2 long-chain dodecyl groups are present, so that the invention is easy to combine with colloid asphaltene in thick oil, and then the whole molecule is penetrated into colloid and asphaltene sheets, so that the interaction force between aromatic rings in thick oil is weakened; the existence of 2 sulfonic groups and tertiary amino groups enables the thickened oil to be easy to interact with the aqueous solution of the invention to form O/W emulsion, and the external phase forms a continuous water film, so that the flow resistance can be reduced, and the viscosity of crude oil can be greatly reduced.
Compared with the prior art, the invention has the beneficial effects and advantages that:
(1) The thick oil viscosity reducer has the characteristics of wide raw material sources, simple synthesis process, clean and pollution-free process;
(2) The thick oil viscosity reducer has the characteristics of high activity and low concentration, and can enable the viscosity reduction rate of the thick oil to reach more than 99.6% under the condition of using the concentration of 1000 mg/L.
Detailed Description
The endpoints and any values of the ranges disclosed herein are not limited to the precise range or value, and are understood to encompass values approaching those ranges or values. For numerical ranges, one or more new numerical ranges may be found between the endpoints of each range, between the endpoint of each range and the individual point value, and between the individual point value, in combination with each other, and are to be considered as specifically disclosed herein.
Example 1
(1) Into a four-necked flask equipped with a condenser, 0.05mol of 2, 6-bis (dodecyloxy) benzaldehyde, 0.04mol of 2-aminoethanesulfonic acid, 0.05mol of 30wt% aqueous formic acid, 142.2g of deionized water were successively added, and the mixture was heated and refluxed for 3 hours. Cooling to below 40 ℃, transferring the reaction liquid into a rotary evaporator, and distilling under reduced pressure to obtain brown yellow oily matter;
(2) Transferring the oily matter in the step (1) into a four-necked flask by using 237g of 95wt% ethanol, regulating the pH value to 9-10 by using 2mol/L sodium hydroxide solution, adding 0.04mol of sodium chloroethanesulfonate, heating and refluxing for 6 hours, maintaining the pH value to 9-10 by using 2mol/L sodium hydroxide during the reaction, and distilling under reduced pressure to obtain a viscous brown solid;
(3) Recrystallization from cyclohexane gave a pale yellow solid, product J 1.
Example 2
(1) Into a four-necked flask equipped with a condenser, 0.05mol of 2, 6-bis (dodecyloxy) benzaldehyde, 0.06mol of 2-aminoethanesulfonic acid, 0.08mol of 30wt% aqueous formic acid, 94.8g of deionized water were successively added, and the mixture was heated and refluxed for 1.5 hours. Cooling to below 40 ℃, transferring the reaction liquid into a rotary evaporator, and distilling under reduced pressure to obtain brown yellow oily matter;
(2) Transferring the oily matter in the step (1) into a four-necked flask by using 474g of 95wt% ethanol, regulating the pH to 9-10 by using 2mol/L sodium hydroxide solution, adding 0.06mol of sodium chloroethanesulfonate, heating and refluxing for 7h, maintaining the pH to 9-10 by using 2mol/L sodium hydroxide during the reaction, and distilling under reduced pressure to obtain a viscous brown solid;
(3) Recrystallization from cyclohexane gave a pale yellow solid, product J 2.
Example 3
(1) Into a four-necked flask equipped with a condenser, 0.05mol of 2, 6-bis (dodecyloxy) benzaldehyde, 0.045mol of 2-aminoethanesulfonic acid, 0.1mol of 30wt% aqueous formic acid, 127.4g of deionized water were successively added, and the mixture was heated under reflux for 3 hours. Cooling to below 40 ℃, transferring the reaction liquid into a rotary evaporator, and distilling under reduced pressure to obtain brown yellow oily matter;
(2) Transferring the oily matter in the step (1) into a four-necked flask by using 289g of 95wt% ethanol, regulating the pH to 9-10 by using 2mol/L sodium hydroxide solution, adding 0.046mol of sodium chloroethanesulfonate, heating and refluxing for 8 hours, maintaining the pH to 9-10 by using 2mol/L sodium hydroxide during the reaction, and distilling under reduced pressure to obtain a viscous brown solid;
(3) Recrystallization from cyclohexane gave a pale yellow solid, product J 3.
Example 4
(1) Into a four-necked flask equipped with a condenser, 0.05mol of 2, 6-bis (dodecyloxy) benzaldehyde, 0.055mol of 2-aminoethanesulfonic acid, 0.12mol of 30wt% aqueous formic acid, 100.7g of deionized water were successively added, and the mixture was heated and refluxed for 2 hours. Cooling to below 40 ℃, transferring the reaction liquid into a rotary evaporator, and distilling under reduced pressure to obtain brown yellow oily matter;
(2) Transferring the oily matter in the step (1) into a four-necked flask by using 441g of 95wt% ethanol, regulating the pH to 9-10 by using 2mol/L sodium hydroxide solution, adding 0.055mol of sodium chloroethanesulfonate, heating and refluxing for 10h, maintaining the pH to 9-10 by using 2mol/L sodium hydroxide during the reaction, and distilling under reduced pressure to obtain a viscous brown solid;
(3) Recrystallization from cyclohexane gave a pale yellow solid, product J 4.
Example 5
(1) Into a four-necked flask equipped with a condenser, 0.05mol of 2, 6-bis (dodecyloxy) benzaldehyde, 0.049mol of 2-aminoethanesulfonic acid, 0.14mol of 30wt% aqueous formic acid, 117.5g of deionized water were successively added, and the mixture was heated and refluxed for 2.5 hours. Cooling to below 40 ℃, transferring the reaction liquid into a rotary evaporator, and distilling under reduced pressure to obtain brown yellow oily matter;
(2) Transferring the oily matter in the step (1) into a four-necked flask by 450g of 95wt% ethanol, regulating the pH to 9-10 by using 2mol/L sodium hydroxide solution, adding 0.048mol of sodium chloroethanesulfonate, heating and refluxing for 11h, maintaining the pH to 9-10 by using 2mol/L sodium hydroxide during the reaction, and distilling under reduced pressure to obtain a viscous brown solid;
(3) Recrystallization from cyclohexane gave a pale yellow solid, product J 5.
Example 6
(1) Into a four-necked flask equipped with a condenser, 0.05mol of 2, 6-bis (dodecyloxy) benzaldehyde, 0.05mol of 2-aminoethanesulfonic acid, 0.14mol of 30wt% aqueous formic acid, 104.8g of deionized water were successively added, and the mixture was heated and refluxed for 3 hours. Cooling to below 40 ℃, transferring the reaction liquid into a rotary evaporator, and distilling under reduced pressure to obtain brown yellow oily matter;
(2) Transferring the oily matter in the step (1) into a four-necked flask by using 470g of 95wt% ethanol, regulating the pH to 9-10 by using 2mol/L sodium hydroxide solution, adding 0.052mol of sodium chloroethanesulfonate, heating and refluxing for 9 hours, maintaining the pH to 9-10 by using 2mol/L sodium hydroxide during the reaction, and distilling under reduced pressure to obtain a viscous brown solid;
(3) Recrystallization from cyclohexane gave a pale yellow solid, product J 6.
Example 7
(1) Into a four-necked flask equipped with a condenser, 0.05mol of 2, 6-bis (dodecyloxy) benzaldehyde, 0.051mol of 2-aminoethanesulfonic acid, 0.15mol of 30wt% aqueous formic acid, 124.5g of deionized water were successively added, and the mixture was heated and refluxed for 3 hours. Cooling to below 40 ℃, transferring the reaction liquid into a rotary evaporator, and distilling under reduced pressure to obtain brown yellow oily matter;
(2) Transferring the oily matter in the step (1) into a four-necked flask by 400g of 95wt% ethanol, regulating the pH to 9-10 by using 2mol/L sodium hydroxide solution, adding 0.05mol of sodium chloroethanesulfonate, heating and refluxing for 12h, maintaining the pH to 9-10 by using 2mol/L sodium hydroxide during the reaction, and distilling under reduced pressure to obtain a viscous brown solid;
(3) Recrystallization from cyclohexane gave a pale yellow solid, product J 7.
Test example 1 evaluation of viscosity reducer for heavy oil
The crude oil used in the experiment is a thick oil sample of a certain area of a victory oil field, and the viscosity of the crude oil is 22400 mPa.s at 50 ℃.
The thick oil viscosity reducer J 1、J2、J3、J4、J5、J6、J7 and the sodium dodecyl benzene sulfonate and the petroleum sulfonate are respectively prepared into 300mg/L and 1000mg/L solutions.
The evaluation method refers to Q/SH 10201519-2016 general technical condition for viscosity reducer of heavy oil, and the test results are shown in Table 1.
TABLE 1 viscosity reduction test results
As can be seen from table 1: for crude oil with the viscosity of 22400 mPa.s, the viscosity reduction rate of the thick oil viscosity reducer J 1、J2、J3、J4、J5、J6、J7 is greater than 99.2% when the using concentration is 300mg/L, the highest viscosity reduction rate of J 6 is 99.53%, the sodium dodecyl benzene sulfonate is not emulsified, and the viscosity reduction rate of petroleum sulfonate is 99.07%; when the viscosity reducer J 1、J2、J3、J4、J5、J6、J7 is used at the concentration of 300mg/L, the viscosity reduction rate of the thickened oil is more than 99.26%, the highest viscosity reduction rate is 99.68%, the viscosity reduction rate of sodium dodecyl benzene sulfonate is 99.13%, and the viscosity reduction rate of petroleum sulfonate is 99.31%, which is obviously lower than that of the thickened oil.
Test example 2 evaluation of viscosity reducer for heavy oil
The crude oil used in the experiment is a thick oil sample of a certain area of a victory oil field, and the viscosity of the crude oil is 45000 mPa.s at 50 ℃.
The thick oil viscosity reducer J 1、J2、J3、J4、J5、J6、J7 and the sodium dodecyl benzene sulfonate and the petroleum sulfonate are respectively prepared into 300mg/L and 1000mg/L solutions.
The evaluation method refers to Q/SH 10201519-2016 general technical condition for viscosity reducer of heavy oil, and the test results are shown in Table 2.
TABLE 2 viscosity reduction test results
As can be seen from table 2: for crude oil with the viscosity of 45000 mPa.s, the viscosity reduction rate of the thick oil viscosity reducer J 1、J2、J3、J4、J5、J6、J7 is more than 99.5% when the using concentration is 300mg/L, the highest viscosity reduction rate of J 6 is 99.68%, and sodium dodecyl benzene sulfonate and petroleum sulfonate are not emulsified; when the concentration is 1000mg/L, the viscosity reduction rate of the thick oil viscosity reducer J 1、J2、J3、J4、J5、J6、J7 is more than 99.7%, the highest viscosity reduction rate is 99.82%, the viscosity reduction rate of sodium dodecyl benzene sulfonate is 99.60%, and the viscosity reduction rate of petroleum sulfonate is 99.65%.
The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, a number of simple variants of the technical solution of the invention are possible, including combinations of the individual technical features in any other suitable way, which simple variants and combinations should likewise be regarded as being disclosed by the invention, all falling within the scope of protection of the invention.
Claims (8)
1. The preparation method of the thick oil viscosity reducer is characterized by comprising the following steps of:
(1) Sequentially adding 2, 6-bis (dodecyloxy) benzaldehyde, 2-aminoethanesulfonic acid, 30wt% formic acid aqueous solution and deionized water into a four-neck flask with a condenser tube, heating and refluxing, cooling to below 40 ℃, transferring the reaction solution into a rotary evaporator, and distilling under reduced pressure to obtain a brown yellow oily substance;
(2) Transferring the oily substance into a four-necked flask by using 95wt% ethanol, regulating the pH value to 9-10 by using 2mol/L sodium hydroxide solution, adding sodium chloroethanesulfonate, heating and refluxing, maintaining the pH value to 9-10 by using 2mol/L sodium hydroxide during the reaction period, and distilling under reduced pressure to obtain a viscous brown solid;
(3) And (3) recrystallizing with cyclohexane to obtain a light yellow solid, namely the thick oil viscosity reducer.
2. The method for preparing a thick oil viscosity reducer according to claim 1, wherein the amounts of the 2-aminoethanesulfonic acid, the formic acid and the sodium chloroethanesulfonate are respectively 0.8-1.2 mol parts, 1-3 mol parts and 0.8-1.2 mol parts based on 1 mol part of the 2, 6-bis (dodecyloxy) benzaldehyde.
3. The method for preparing a thick oil viscosity reducer according to claim 1, wherein the amounts of the 2-aminoethanesulfonic acid, the formic acid and the sodium chloroethanesulfonate are respectively 0.9-1.1 mole parts, 2-3 mole parts and 0.9-1.1 mole parts based on 1 mole part of the 2, 6-bis (dodecyloxy) benzaldehyde.
4. The preparation method of the thick oil viscosity reducer according to claim 1, wherein in the step (1), the mass ratio of deionized water to 2, 6-bis (dodecyloxy) benzaldehyde is 4-6:1.
5. The method for preparing a thickened oil viscosity reducer according to claim 1, wherein in the step (1), the reflux time is 1-3h.
6. The preparation method of the thick oil viscosity reducer according to claim 1, wherein in the step (2), the mass ratio of the ethanol to the 2, 6-bis (dodecyloxy) benzaldehyde is 10-20:1.
7. The method for preparing a thickened oil viscosity reducer according to claim 1, wherein in the step (2), the reflux time is 6-12h.
8. The thick oil viscosity reducer is characterized by comprising the following molecular structural formula:
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202310260090.7A CN116283670B (en) | 2023-03-17 | 2023-03-17 | Thickened oil viscosity reducer and preparation method thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202310260090.7A CN116283670B (en) | 2023-03-17 | 2023-03-17 | Thickened oil viscosity reducer and preparation method thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN116283670A CN116283670A (en) | 2023-06-23 |
CN116283670B true CN116283670B (en) | 2024-06-11 |
Family
ID=86800944
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202310260090.7A Active CN116283670B (en) | 2023-03-17 | 2023-03-17 | Thickened oil viscosity reducer and preparation method thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN116283670B (en) |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05113631A (en) * | 1991-06-21 | 1993-05-07 | Fuji Photo Film Co Ltd | Photographic processing composition and processing method |
CN1115778A (en) * | 1994-07-28 | 1996-01-31 | 新疆石油管理局油田工艺研究所 | Viscosity reducer and its prepn |
CN1221650A (en) * | 1998-12-11 | 1999-07-07 | 李大石 | Surface active agent |
CN106032466A (en) * | 2015-03-20 | 2016-10-19 | 中国石油化工股份有限公司 | Viscosity reducer by emulsification for heavy oil |
JP2016221482A (en) * | 2015-06-02 | 2016-12-28 | 国立大学法人 東京大学 | Composite semipermeable membrane |
CN110252395A (en) * | 2019-07-01 | 2019-09-20 | 湖北远大生命科学与技术有限责任公司 | A kind of catalyst being used to prepare high-purity taurine and its application |
CN113226990A (en) * | 2018-12-27 | 2021-08-06 | 安斯泰来制药株式会社 | Method for producing nanoparticles comprising iron oxide-containing metal particles to which one or more hydrophilic ligands are coordinately bound |
CN114933560A (en) * | 2022-06-16 | 2022-08-23 | 山东科兴化工有限责任公司 | Surfactant for improving crude oil recovery ratio and preparation method and application thereof |
CN115651185A (en) * | 2022-12-27 | 2023-01-31 | 山东科兴化工有限责任公司 | Viscosity regulator for oil field and preparation method and application thereof |
-
2023
- 2023-03-17 CN CN202310260090.7A patent/CN116283670B/en active Active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05113631A (en) * | 1991-06-21 | 1993-05-07 | Fuji Photo Film Co Ltd | Photographic processing composition and processing method |
CN1115778A (en) * | 1994-07-28 | 1996-01-31 | 新疆石油管理局油田工艺研究所 | Viscosity reducer and its prepn |
CN1221650A (en) * | 1998-12-11 | 1999-07-07 | 李大石 | Surface active agent |
CN106032466A (en) * | 2015-03-20 | 2016-10-19 | 中国石油化工股份有限公司 | Viscosity reducer by emulsification for heavy oil |
JP2016221482A (en) * | 2015-06-02 | 2016-12-28 | 国立大学法人 東京大学 | Composite semipermeable membrane |
CN113226990A (en) * | 2018-12-27 | 2021-08-06 | 安斯泰来制药株式会社 | Method for producing nanoparticles comprising iron oxide-containing metal particles to which one or more hydrophilic ligands are coordinately bound |
CN110252395A (en) * | 2019-07-01 | 2019-09-20 | 湖北远大生命科学与技术有限责任公司 | A kind of catalyst being used to prepare high-purity taurine and its application |
CN114933560A (en) * | 2022-06-16 | 2022-08-23 | 山东科兴化工有限责任公司 | Surfactant for improving crude oil recovery ratio and preparation method and application thereof |
CN115651185A (en) * | 2022-12-27 | 2023-01-31 | 山东科兴化工有限责任公司 | Viscosity regulator for oil field and preparation method and application thereof |
Non-Patent Citations (1)
Title |
---|
稠油乳化降粘剂QX的合成与特性;王秋霞等;《精细石油化工进展》;第5卷(第7期);14-16 * |
Also Published As
Publication number | Publication date |
---|---|
CN116283670A (en) | 2023-06-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN111961457A (en) | Oil displacement complexing agent for heavy oil reservoir and preparation method and application thereof | |
CN107501135B (en) | Preparation and application of sulfonate anionic surfactant containing double long-chain alkyl | |
CN116283670B (en) | Thickened oil viscosity reducer and preparation method thereof | |
CN110951475A (en) | Ultra-high temperature resistant low-viscosity low-corrosion emulsifier, emulsified acid system and preparation method thereof | |
CN115960021B (en) | Thickened oil viscosity reducer for improving crude oil recovery ratio and synthesis method thereof | |
CN108485625B (en) | Anionic nonionic surfactant thickened oil viscosity-reducing oil displacement agent and preparation method and application thereof | |
CN112280547A (en) | Viscosity-reducing oil displacement agent for super-thick crude oil and preparation method and application thereof | |
CN115651185B (en) | Viscosity regulator for oil field and preparation method and application thereof | |
CN116804082B (en) | Viscosity-reducing drag reducer for thickened oil for displacement of reservoir oil and preparation method thereof | |
CN117756682A (en) | Surfactant for oil and gas field and preparation method thereof | |
CN105820805A (en) | Clean fracturing fluid for oil fields and preparation method thereof | |
CN111592910B (en) | Method for preparing compound polyether demulsifier | |
CN114479814A (en) | Temperature-resistant salt-tolerant viscosity reducer for thick oil and preparation method thereof | |
CN114591468A (en) | Oil-water interface activation drag reducer for cold production of thickened oil and preparation method thereof | |
CN115873576B (en) | Thickened oil viscosity reducer and preparation method thereof | |
CN106543998A (en) | A kind of reducing viscosity in hydrothermal cracking and catalyzing agent and preparation method thereof | |
CN113621358B (en) | Viscosity-reducing oil displacement agent for extra-thick crude oil and preparation method and application thereof | |
CN102604621B (en) | Novel high-efficiency composite viscosity reducer for super heavy oil | |
CN110372537A (en) | A kind of Gemini surface active and preparation method thereof containing schiff base structure | |
CN115124989B (en) | Thickened oil viscosity-reducing cold recovery method and application thereof | |
CN117903080A (en) | Thickened oil viscosity reducer and preparation method thereof | |
CN104946226A (en) | Thick oil sulfonate preparing method | |
CN115584256A (en) | High-temperature-resistant high-salt cleanup additive for acidizing and fracturing and preparation method thereof | |
CN112480898B (en) | Composite clean fracturing fluid system and preparation method thereof | |
CN112500844B (en) | Preparation method of thickened oil viscosity reduction and recovery increasing agent, thickened oil viscosity reduction and recovery increasing agent and application |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20240516 Address after: 257000 No. 45, Liaohe Road, Dongying District, Dongying City, Shandong Province Applicant after: Dongying Dashun Chemical Co.,Ltd. Country or region after: China Address before: 257000 No. 377, Xisi Road, Dongying City, Shandong Province Applicant before: Shengli Oilfield Kaidu Petroleum Technology Development Co.,Ltd. Country or region before: China |
|
TA01 | Transfer of patent application right | ||
GR01 | Patent grant | ||
GR01 | Patent grant |