CN108864418B - Aging crude oil demulsifier and preparation method thereof - Google Patents
Aging crude oil demulsifier and preparation method thereof Download PDFInfo
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- CN108864418B CN108864418B CN201810744027.XA CN201810744027A CN108864418B CN 108864418 B CN108864418 B CN 108864418B CN 201810744027 A CN201810744027 A CN 201810744027A CN 108864418 B CN108864418 B CN 108864418B
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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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
- C08G65/2621—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups
- C08G65/2624—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups containing aliphatic amine groups
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G33/00—Dewatering or demulsification of hydrocarbon oils
- C10G33/04—Dewatering or demulsification of hydrocarbon oils with chemical means
Abstract
The invention discloses an aged crude oil demulsifier and a preparation method thereof. The method for preparing the crude oil demulsifier comprises the following steps: 1) reacting the single-acid type phenolic amine resin, a catalyst and propylene oxide to obtain a demulsifier lipophilic head compound; 2) and (2) reacting the demulsifier oleophylic head compound obtained in the step 1), a catalyst and ethylene oxide to obtain the demulsifier oleophylic head compound. The demulsifier can be used for demulsifying aged crude oil, particularly for demulsifying the aged crude oil on an offshore platform quickly and efficiently. The invention has a particularly outstanding demulsification effect on aging oil, particularly Bohai oil fields, is beneficial to energy conservation and emission reduction, and reduces the production cost of enterprises.
Description
Technical Field
The invention relates to an aged crude oil demulsifier and a preparation method thereof, belonging to the technical field of petroleum processing.
Background
Aged crude oil, also called aged oil, refers to crude oil emulsion which is formed under the action of agents, mechanical impurities, colloid, asphaltene, bacteria, air, circulating shear and other factors in the production and treatment processes of crude oil, has increasingly stable emulsified state, cannot be treated by conventional agents and treatment methods, and has great influence on a crude oil dehydration system.
With the wide application of polymer flooding technology, the oil content of the produced crude oil is even more than 1 ten thousand ppm after demulsification, and oil-containing suspended matters are generated after adding a water clarifier, which is called as aging oil. The aged oil contains more than 30% of water, and no effective treatment agent is available at present. The method has important significance for reducing the water content in the aging oil and reducing the energy loss of the submarine oil pipeline. Research and development of a demulsifier suitable for aging oil are very urgent problems.
Disclosure of Invention
The invention aims to provide an aged crude oil demulsifier and a preparation method thereof.
The method for preparing the crude oil demulsifier provided by the invention comprises the following steps:
1) reacting the tannic acid type phenolic amine resin, a catalyst and propylene oxide to obtain a demulsifier lipophilic head compound;
2) and (2) reacting the lipophilic head compound of the demulsifier obtained in the step 1), a catalyst and ethylene oxide to obtain the crude oil demulsifier.
In step 1) and step 2) of the above method, the catalyst is alkali; specifically at least one selected from potassium hydroxide, sodium hydride, sodium methoxide, potassium methoxide and sodium ethoxide;
the amount of the catalyst is 0.1-1% of the total mass of the tannic acid type phenolic amine resin and the propylene oxide; in particular to 0.3 percent;
the mass ratio of the ethylene oxide to the propylene oxide is (0.01-2): 1; specifically 0.01:1, 0.015:1, 0.029:1 or 0.043: 1.
In the step 1) of reacting, the mass ratio of the tannic acid type phenolic amine resin to the propylene oxide is 1: 50-200; specifically, 1: 69-199;
the reaction temperature is 100-140 ℃; the reaction pressure is 0.2-0.4 MPa; the reaction time is 5-25 h; in particular 10 h.
In the reaction step of the step 2), the reaction temperature is 100-120 ℃; the reaction pressure is 0.15-0.35 MPa; the reaction time is 5-10 h.
The tannic acid type phenolic amine resin provided by the invention is prepared by a method comprising the following steps:
a. carrying out hydroxymethylation reaction on tannic acid and formaldehyde water solution to obtain hydroxymethyl tannic acid;
b. and d, dropwise adding the hydroxymethyl tannic acid obtained in the step a into vinylamine for polymerization, evaporating methanol and water after dropwise adding, and washing with a detergent to obtain the tannic acid type phenolic amine resin.
In the step a of the hydroxymethylation reaction of the method, the feeding molar ratio of the tannic acid to the formaldehyde is 1: 20-60 parts of; specifically, 1: 25-40; the mass percentage concentration of the formaldehyde aqueous solution is 35-40%; in particular 38 percent; the tannic acid is also called tannic acid and tannic acid, and the CAS number: 1401-55-4, which are commercially available from a variety of open commercial sources.
The reaction temperature is 40-80 ℃; in particular 70 ℃; the reaction time is 4-6 h; in particular 5 h;
the hydroxymethylation reaction is carried out in a solvent; the solvent is at least one selected from methanol, ethanol, isopropanol, tetrahydrofuran, dichloromethane, chloroform, carbon tetrachloride, tetrahydrofuran and diethyl ether;
the hydroxymethylation reaction is carried out in an inert atmosphere; the inert atmosphere is nitrogen atmosphere;
the tannic acid is mixed with formaldehyde in a dropwise manner; in the dripping step, the dripping speed is 2-20 g/min; in particular 10 g/min.
In the step b, the feeding molar ratio of the vinylamine to the tannic acid is 10-40: 1; specifically 15-30: 1;
in the dripping step, the dripping speed is 2-20 g/min; specifically 10 g/min; in the step of polymerization reaction, the temperature is 60-100 ℃; the reaction time is 4-6 h; in particular 5 h;
the polymerization reaction is carried out in a solvent; the solvent is at least one selected from methanol, ethanol, isopropanol, tetrahydrofuran, dichloromethane, chloroform, carbon tetrachloride, tetrahydrofuran and diethyl ether;
the vinylamine is at least one selected from ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine and hexaethyleneheptamine;
the detergent is at least one selected from dichloromethane, trichloromethane, carbon tetrachloride, tetrahydrofuran and diethyl ether.
In addition, the crude oil demulsifier prepared by the method and the application of the crude oil demulsifier in the demulsification of aged crude oil also belong to the protection scope of the invention. The aged crude oil can be specifically sourced from a Bohai sea oil field.
The invention has the beneficial effects that:
1. compared with bisphenol A, amines, alcohols and phenolic resin initiators, the synthesis process of the tannic acid type phenolic amine resin is improved, side reactions such as Schiff base are avoided, more phenolic hydroxyl ortho-position points on a benzene ring participate in the reaction, and more branched chains are obtained. And sufficient formaldehyde also ensures that the ortho-position of the phenolic hydroxyl group can be completely reacted to form the phenolic amine resin with more branched chains.
2. The demulsifier can be used for demulsifying aged crude oil, particularly for demulsifying the aged crude oil on an offshore platform quickly and efficiently. The invention has a particularly outstanding demulsification effect on aging oil, particularly Bohai oil fields, is beneficial to energy conservation and emission reduction, and reduces the production cost of enterprises. The demulsifier solves the problem that aged crude oil is difficult to effectively demulsify, and meets the requirements of an offshore platform on high dehydration speed and high dehydration rate of the demulsifier.
Detailed Description
The present invention will be further illustrated with reference to the following specific examples, but the present invention is not limited to the following examples. The method is a conventional method unless otherwise specified. The starting materials are commercially available from the open literature unless otherwise specified.
Example 1 Synthesis of demulsifier A
1) 68g of tannic acid was weighed, dissolved in 600ml of methanol, and the solution was poured into a constant pressure dropping funnel. Adding 130g of formaldehyde aqueous solution with the mass percentage concentration of 38% into a 1L three-neck flask, keeping the temperature at 70 ℃ for 30min, introducing nitrogen, slowly dripping the tannin methanol solution into a constant-pressure dropping funnel at the dripping speed of 10g/min, continuously reacting for 5h after dripping is finished, and removing methanol and formaldehyde by rotary evaporation to obtain the hydroxymethyl tannin.
2) Dissolving hydroxymethyl tannic acid in 500ml of methanol again, slowly dripping 151g of tetraethylenepentamine at 80 ℃ at a dripping speed of 10g/min, reacting for 5 hours after dripping, evaporating the methanol and water under reduced pressure, pouring 500ml of dichloromethane into the mixture while the mixture is hot, washing the mixture for three times by using 500ml of dichloromethane, performing rotary evaporation, and drying for 24 hours to obtain the tannic acid type phenolic amine resin.
3) 10g of the obtained tannic acid type phenol amine resin and 2g of potassium hydroxide were put into an autoclave, and after the autoclave was sealed, stirring was started and the temperature was raised, nitrogen gas was discharged 3 times, and vacuum was applied for 30 minutes. When the temperature is raised to 100-140 ℃, 690g of propylene oxide is slowly added, the pressure is kept at 0.2-0.4 MPa, and the reaction is carried out for 10 hours, thus obtaining the demulsifier lipophilic head compound.
4) 60g of the obtained demulsifier lipophilic head compound and 0.1g of potassium hydroxide are put into an autoclave, after the autoclave is sealed, stirring is started, the temperature is raised, nitrogen is exhausted for 3 times, and vacuum pumping is carried out for 30 minutes. When the temperature is raised to 100-120 ℃, slowly adding 30g of ethylene oxide, keeping the pressure at 0.2-0.4 MPa, and reacting for 5 hours to obtain the polyether demulsifier A
Example 2 Synthesis of demulsifier B
10g of the tannic acid type phenol amine resin obtained in example 1 and 2g of potassium hydroxide were put into an autoclave, and after the autoclave was sealed, stirring was started and the temperature was raised, nitrogen gas was discharged 3 times, and vacuum was applied for 30 minutes. When the temperature is raised to 100-140 ℃, 690g of propylene oxide is slowly added, the pressure is kept at 0.2-0.4 MPa, and the reaction is carried out for 10 hours, thus obtaining the demulsifier lipophilic head compound.
60g of the obtained demulsifier lipophilic head compound and 0.1g of potassium hydroxide are put into an autoclave, after the autoclave is sealed, stirring is started, the temperature is raised, nitrogen is exhausted for 3 times, and the vacuum is pumped for 30 minutes. When the temperature is raised to 100-120 ℃, slowly adding 20g of ethylene oxide, keeping the pressure at 0.2-0.4 MPa, and reacting for 5 hours to obtain the polyether demulsifier B.
Example 3 Synthesis of demulsifier C
10g of the tannic acid type phenol amine resin obtained in example 1 and 6g of potassium hydroxide were put into an autoclave, and after the autoclave was sealed, stirring was started and the temperature was raised, nitrogen gas was discharged 3 times, and vacuum was applied for 30 minutes. When the temperature is raised to 100-140 ℃, 1990 propylene oxide is slowly added, the pressure is kept at 0.2-0.4 MPa, and the reaction is carried out for 10 hours, thus obtaining the demulsifier lipophilic head compound.
60g of the obtained demulsifier lipophilic head compound and 0.1g of potassium hydroxide are put into an autoclave, after the autoclave is sealed, stirring is started, the temperature is raised, nitrogen is exhausted for 3 times, and the vacuum is pumped for 30 minutes. When the temperature is raised to 100-120 ℃, slowly adding 30g of ethylene oxide, keeping the pressure at 0.2-0.4 MPa, and reacting for 5 hours to obtain the polyether demulsifier C.
Example 4 Synthesis of demulsifier D
10g of the tannic acid type phenol amine resin obtained in example 1 and 6g of potassium hydroxide were put into an autoclave, and after the autoclave was sealed, stirring was started and the temperature was raised, nitrogen gas was discharged 3 times, and vacuum was applied for 30 minutes. When the temperature is raised to 100-140 ℃, 1990 propylene oxide is slowly added, the pressure is kept at 0.2-0.4 MPa, and the reaction is carried out for 10 hours, thus obtaining the demulsifier lipophilic head compound.
60g of the obtained demulsifier lipophilic head compound and 0.1g of potassium hydroxide are put into an autoclave, after the autoclave is sealed, stirring is started, the temperature is raised, nitrogen is exhausted for 3 times, and the vacuum is pumped for 30 minutes. And when the temperature is raised to 100-120 ℃, slowly adding 20g of ethylene oxide, keeping the pressure at 0.2-0.4 MPa, and reacting for 5 hours to obtain the polyether demulsifier D.
Example 5 crude oil demulsification experiment
The demulsifier synthesized in examples 1-5 was subjected to a demulsification experiment on aged oil at the field temperature of the oil field in the Bohai sea by using the method for detecting the service performance of the crude oil demulsifier (bottle test method) of SY/T5281-2000 in the oil and gas industry, the concentration of the demulsifier was 100mg/L, and the demulsification data is shown in Table 1.
Demulsifying Effect of the demulsifiers synthesized in Table 1 and examples 1 to 5
As can be seen from the table 1, the demulsifier provided by the invention can be used for demulsifying aged crude oil, particularly for demulsifying the aged crude oil on an offshore platform quickly and efficiently, and the dehydration rate can be more than 93% when the demulsification time is not more than 60 min. The demulsifier has a particularly outstanding demulsification effect on the Bohai sea oil field, is beneficial to energy conservation and emission reduction, and reduces the production cost of enterprises. The demulsifier solves the problem that aged crude oil is difficult to effectively demulsify, and meets the requirements of an offshore platform on high dehydration speed and high dehydration rate of the demulsifier.
Claims (13)
1. A method of preparing a crude oil demulsifier, comprising the steps of:
1) reacting the single-acid type phenolic amine resin, a catalyst and propylene oxide to obtain a demulsifier lipophilic head compound;
the tannic acid type phenolic amine resin is prepared by a method comprising the following steps:
a. carrying out hydroxymethylation reaction on tannic acid and formaldehyde water solution to obtain hydroxymethyl tannic acid;
b. b, dropwise adding the hydroxymethyl tannic acid obtained in the step a into vinylamine for polymerization, evaporating methanol and water after dropwise adding, and washing with a detergent to obtain the tannic acid type phenolic amine resin;
2) and (2) reacting the lipophilic head compound of the demulsifier obtained in the step 1), a catalyst and ethylene oxide to obtain the crude oil demulsifier.
2. The method of claim 1, wherein: in the step 1) and the step 2), the catalyst is alkali;
the amount of the catalyst is 0.1-1% of the total mass of the tannic acid type phenolic amine resin and the propylene oxide;
the mass ratio of the ethylene oxide to the propylene oxide is (0.01-2): 1.
3. the method of claim 2, wherein: in the step 1) and the step 2), the catalyst is at least one selected from potassium hydroxide, sodium hydride, sodium methoxide, potassium methoxide and sodium ethoxide;
the dosage of the catalyst is 0.3 percent of the total mass of the tannic acid type phenolic amine resin and the propylene oxide.
4. The method of claim 1, wherein: in the step 1) of reacting, the mass ratio of the tannic acid type phenolic amine resin to the propylene oxide is 1: 50-200;
the reaction temperature is 100-140 ℃; the reaction pressure is 0.2-0.4 MPa; the reaction time is 5-25 h.
5. The method of claim 4, wherein: in the step 1), the reaction time is 10 h.
6. The method of claim 1, wherein: in the reaction step of the step 2), the reaction temperature is 100-120 ℃; the reaction pressure is 0.15-0.35 MPa; the reaction time is 5-10 h.
7. The method of claim 1, wherein: in the step a of hydroxymethylation reaction, the feeding molar ratio of tannic acid to formaldehyde is 1: 20-60 parts of; the mass percentage concentration of the formaldehyde aqueous solution is 35-40%;
the reaction temperature is 40-80 ℃; the reaction time is 4-6 h;
the hydroxymethylation reaction is carried out in a solvent;
the hydroxymethylation reaction is carried out in an inert atmosphere;
the tannic acid is mixed with formaldehyde in a dropwise manner; in the dripping step, the dripping speed is 2-20 g/min.
8. The method of claim 7, wherein: in the step a of hydroxymethylation reaction, the feeding molar ratio of tannic acid to formaldehyde is 1: 25-40; the mass percentage concentration of the formaldehyde aqueous solution is 38%;
the reaction temperature is 70 ℃; the reaction time is 5 h;
the solvent is at least one selected from methanol, ethanol, isopropanol, dichloromethane, chloroform, carbon tetrachloride, tetrahydrofuran and diethyl ether;
the inert atmosphere is a nitrogen atmosphere.
9. The method according to any one of claims 1 to 8, wherein: in the step b, the feeding molar ratio of the vinylamine to the tannic acid is 10-40: 1;
in the dripping step, the dripping speed is 2-20 g/min; in the step of polymerization reaction, the temperature is 60-100 ℃; the reaction time is 4-6 h;
the polymerization reaction is carried out in a solvent;
the vinylamine is at least one selected from ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine and hexaethyleneheptamine;
the detergent is at least one selected from dichloromethane, trichloromethane, carbon tetrachloride, tetrahydrofuran and diethyl ether.
10. The method of claim 9, wherein: in the step b, the feeding molar ratio of the vinylamine to the tannic acid is 15-30: 1;
in the step of polymerization reaction, the reaction time is 5 h;
the solvent is at least one selected from methanol, ethanol, isopropanol, tetrahydrofuran, dichloromethane, chloroform, carbon tetrachloride, tetrahydrofuran and diethyl ether.
11. A crude oil demulsifier prepared by the method of any one of claims 1-10.
12. Use of the crude oil demulsifier of claim 11 in demulsification of aged crude oil.
13. Use according to claim 12, characterized in that: the aged crude oil is sourced from a Bohai sea oil field.
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| CN109705832B (en) * | 2019-01-29 | 2021-09-10 | 中国海洋石油集团有限公司 | High-temperature anti-emulsion synergist and preparation and application thereof |
| CN111171860B (en) * | 2020-01-21 | 2021-08-20 | 中海油天津化工研究设计院有限公司 | Demulsifier for aged crude oil water-in-oil emulsion and preparation method thereof |
| CN114621105A (en) * | 2020-12-10 | 2022-06-14 | 中国石油化工股份有限公司 | Polymer-containing crude oil demulsifier and preparation method thereof |
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| GB611406A (en) * | 1943-11-01 | 1948-10-29 | Lockheed Aircraft Corp | Improvements in or relating to emulsifiers for rendering water-thinnable the concentrates of coating compositions, the improved water-thinnable coating compositions, and methods of thinning the same |
| CN101649361A (en) * | 2009-08-27 | 2010-02-17 | 陕西科技大学 | Method for preparing tannin modified vinyl class polymer tanning agent |
| CN106633027A (en) * | 2016-10-10 | 2017-05-10 | 太原理工大学 | Method for preparing aniline molecularly imprinted polymers |
| CN107744801A (en) * | 2017-11-23 | 2018-03-02 | 齐鲁工业大学 | A kind of poly- phenol amine sorbing material of new lignin-base and preparation method |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB611406A (en) * | 1943-11-01 | 1948-10-29 | Lockheed Aircraft Corp | Improvements in or relating to emulsifiers for rendering water-thinnable the concentrates of coating compositions, the improved water-thinnable coating compositions, and methods of thinning the same |
| CN101649361A (en) * | 2009-08-27 | 2010-02-17 | 陕西科技大学 | Method for preparing tannin modified vinyl class polymer tanning agent |
| CN106633027A (en) * | 2016-10-10 | 2017-05-10 | 太原理工大学 | Method for preparing aniline molecularly imprinted polymers |
| CN107744801A (en) * | 2017-11-23 | 2018-03-02 | 齐鲁工业大学 | A kind of poly- phenol amine sorbing material of new lignin-base and preparation method |
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