CN109880651B - Polysiloxane crude oil demulsifier and preparation method thereof - Google Patents
Polysiloxane crude oil demulsifier and preparation method thereof Download PDFInfo
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Abstract
The invention provides a polysiloxane crude oil demulsifier and a preparation method thereof, wherein the method comprises the following steps: (1) mixing side chain hydrogen-containing silicone oil, propenyl polyglycol ether and methacrylic acid in an organic solvent; (2) heating and stirring under the inert gas atmosphere, adding chloroplatinic acid catalyst, continuously heating, and reacting at 90-110 ℃ until the solution is transparent; (3) and (3) cooling the transparent solution obtained in the step (2) to 60-90 ℃, adding N, N-bis-hexaethyleneoxyalkyl alkylamine, 2-acrylamide-2-methylpropanesulfonic acid and a small amount of azodiisobutyronitrile, reacting for 15-20h at the temperature of 60-90 ℃ in an inert gas atmosphere, and distilling the organic solvent at the temperature of below 90 ℃ under reduced pressure to obtain the polysiloxane crude oil demulsifier. The crude oil demulsifier prepared by the invention has high dehydration rate, can be degraded by microorganisms, and is green and environment-friendly.
Description
Technical Field
The invention relates to the field of petrochemical industry, in particular to a polysiloxane crude oil demulsifier and a preparation method thereof.
Background
The polymer flooding can greatly improve the extraction rate of crude oil, and is widely applied to a plurality of oil fields in the east of China. However, the produced fluid contains a certain amount of polymer and surfactant, so that the viscosity of water is increased, the oil-water components are complex, the emulsification phenomenon is serious, the stability of crude oil emulsion is increased, the oil-water separation is difficult, and the discharge standard of oilfield reinjection water is difficult to achieve. At present, the demulsifiers studied at home and abroad are mainly nonionic polyoxyethylene-polyoxypropylene block polymers from the chemical type.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provides a polysiloxane crude oil demulsifier and a preparation method thereof.
In order to achieve the purpose, the invention adopts the technical scheme that: a method of preparing a polysiloxane crude oil demulsifier, the method comprising the steps of:
(1) mixing side chain hydrogen-containing silicone oil (PHMS), propenyl polyglycol ether and methacrylic acid in an organic solvent;
(2) heating and stirring under the inert gas atmosphere, adding chloroplatinic acid catalyst, continuously heating, and reacting at 90-110 ℃ until the solution is transparent;
(3) and (3) cooling the transparent solution obtained in the step (2) to 60-90 ℃, adding N, N-bis-hexaethyleneoxyalkyl alkylamine, 2-acrylamide-2-methylpropanesulfonic acid and a small amount of azodiisobutyronitrile, reacting for 15-20h at the temperature of 60-90 ℃ in an inert gas atmosphere, and distilling the organic solvent at the temperature of below 90 ℃ under reduced pressure to obtain the polysiloxane crude oil demulsifier.
According to the method, after a polymer taking polyether as a branched chain and polysiloxane as a main chain is synthesized through free addition reaction of silicon and hydrogen, the polymer, a quaternary ammonium compound and organic sulfonic acid are used for preparing the polysiloxane crude oil demulsifier. The method has simple process, mild condition and no strict requirement on reaction condition.
Preferably, the N, N-bis-hexaethyleneoxy alkylamine is selected from N, N-bis-hexaethyleneoxy pentadecylamine, N-bis-hexaethyleneoxy hexadecylamine, N-bis-hexaethyleneoxy heptadecylamine, N-bis-hexaethyleneoxy octadecylamine (N, N-bis-hexaethyleneoxy octadecylamine).
Preferably, the method for preparing the N, N-bis-hexaethyleneoxyalkylamine comprises the steps of: mixing C15-C18 alkylamine, 2' -dichlorodiethyl ether, tetraethylene glycol (tetraethylene glycol) and sodium hydroxide in a xylene solvent, heating and refluxing for 3-6 hours under a nitrogen atmosphere, removing the xylene solvent, adding the obtained solid substance into a hot super-saturated sodium chloride solution, extracting with isopropanol, and removing the isopropanol to obtain the N, N-bis-hexaethyleneoxyalkylalkylamine.
Preferably, the organic solvent in step (1) is xylene or n-butanol.
Preferably, the side chain hydrogen-containing silicone oil, the propenyl polyglycol ether and the methacrylic acid are used in a molar ratio of 1:1-1.2: 1-1.2.
Preferably, the N, N-bis-hexaethyleneoxyalkylamine, 2-acrylamido-2-methylpropanesulfonic acid are used in amounts of: the molar ratio of N, N-bis-hexaethyleneoxyalkylamine, 2-acrylamido-2-methylpropanesulfonic acid to methacrylic acid is from 0.8 to 1.2: 1.
Preferably, the N, N-bis-hexaethyleneoxyalkylamine, 2-acrylamido-2-methylpropanesulfonic acid are used in amounts of: the molar ratio of N, N-bis-hexaethyleneoxyalkylamine, 2-acrylamido-2-methylpropanesulfonic acid to methacrylic acid is 0.8:0.8:1, or 0.8:1:1, or 0.8:1.2:1, or 1.2:0.8:1, or 1:1:1, or 1:0.8: 1.
Preferably, the temperature of the reaction in step (2) is 90 ℃, 95 ℃, 100 ℃, 105 ℃ or 110 ℃.
Preferably, the temperature of the reaction in step (3) is 60 ℃, 70 ℃, 75 ℃, 80 ℃ or 90 ℃.
Preferably, the inert gas atmosphere in the step (2) and the step (3) is a nitrogen atmosphere.
The invention also provides a polysiloxane crude oil demulsifier prepared by any one of the preparation methods.
The invention also provides a crude oil demulsifier composition, which comprises 30-50 parts by weight of the polysiloxane crude oil demulsifier, 50-70 parts by weight of phenolic amine aldehyde resin, 60-80 parts by weight of polyaluminium chloride and 2-5 parts by weight of cationic polyacrylamide.
Preferably, the weight ratio of the polysiloxane crude oil demulsifier to the phenolic amine resin in the crude oil demulsifier composition is 1:1, 1:1.2, 1:1.5, 1:1.8 or 1: 2.
The invention has the beneficial effects that: the invention provides a polysiloxane crude oil demulsifier and a preparation method thereof, the method has the advantages of simple preparation process, mild condition, no harsh requirement on reaction conditions and low cost, and the prepared polysiloxane crude oil demulsifier has higher dehydration rate, can be degraded by microorganisms in activated sludge, and is green and environment-friendly.
Drawings
FIG. 1 is a graph showing the results of the degradation of demulsifiers according to examples of the present invention in activated sludge microorganisms.
Detailed Description
To better illustrate the objects, aspects and advantages of the present invention, the present invention will be further described with reference to specific examples.
Example 1
The preparation method of the polysiloxane crude oil demulsifier provided by the embodiment of the invention comprises the following steps:
(1) mixing side chain hydrogen-containing silicone oil (PHMS), propenyl polyglycol ether and methacrylic acid in an organic solvent;
(2) heating and stirring the mixture in a nitrogen atmosphere, adding a chloroplatinic acid catalyst, continuously heating the mixture, and reacting the mixture at 100 ℃ until the solution is transparent;
(3) cooling the transparent solution obtained in the step (2) to 75 ℃, adding N, N-bis-hexaethyleneoxy hexadecylamine, 2-acrylamide-2-methylpropanesulfonic acid and a small amount of azodiisobutyronitrile, reacting for 16 hours at 75 ℃ in a nitrogen atmosphere, and distilling an organic solvent at a reduced pressure below 90 ℃ to obtain a polysiloxane crude oil demulsifier;
the preparation method of the N, N-bis-hexaethyleneoxycetazolyl amine comprises the following steps: hexadecylamine, 2' -dichlorodiethyl ether, tetraethylene glycol (tetraethylene glycol) and sodium hydroxide are mixed in a xylene solvent, then heated and refluxed for 5 hours under the nitrogen atmosphere, the xylene solvent is removed, the obtained solid matter is added into a hot super-saturated sodium chloride solution, and after extraction with isopropanol, the isopropanol is removed to obtain the N, N-bis-hexaethyleneoxycetalkylamine.
The dosage of the N, N-bis-hexaethyleneoxy hexadecylamine and the 2-acrylamide-2-methylpropane sulfonic acid is as follows: the molar ratio of N, N-bis-hexaethyleneoxycetalkylamine, 2-acrylamido-2-methylpropanesulfonic acid to methacrylic acid was 1:1: 1.
Example 2
The only difference between this example and example 1 is that, in the preparation method of the polysiloxane crude oil demulsifier according to the embodiment of the present invention: adding N, N-bis-hexaethyleneoxypentadecylamine in the step (3).
Example 3
The only difference between this example and example 1 is that, in the preparation method of the polysiloxane crude oil demulsifier according to the embodiment of the present invention: adding N, N-bis-hexaethyleneoxy heptadecylamine in the step (3).
Example 4
The only difference between this example and example 1 is that, in the preparation method of the polysiloxane crude oil demulsifier according to the embodiment of the present invention: adding N, N-bis-hexaethyleneoxy octadecylamine into the step (3).
Example 5
The only difference between this example and example 1 is that, in the preparation method of the polysiloxane crude oil demulsifier according to the embodiment of the present invention: the dosage of the N, N-bis-hexaethyleneoxy hexadecylamine and the 2-acrylamide-2-methylpropane sulfonic acid is as follows: the molar ratio of N, N-bis-hexaethyleneoxycetalkylamine, 2-acrylamido-2-methylpropanesulfonic acid to methacrylic acid was 0.8:0.8: 1.
Example 6
The only difference between this example and example 1 is that, in the preparation method of the polysiloxane crude oil demulsifier according to the embodiment of the present invention: the dosage of the N, N-bis-hexaethyleneoxy hexadecylamine and the 2-acrylamide-2-methylpropane sulfonic acid is as follows: the molar ratio of N, N-bis-hexaethyleneoxycetalkylamine, 2-acrylamido-2-methylpropanesulfonic acid to methacrylic acid was 0.8:1: 1.
Example 7
The only difference between this example and example 1 is that, in the preparation method of the polysiloxane crude oil demulsifier according to the embodiment of the present invention: the dosage of the N, N-bis-hexaethyleneoxy hexadecylamine and the 2-acrylamide-2-methylpropane sulfonic acid is as follows: the molar ratio of N, N-bis-hexaethyleneoxycetalkylamine, 2-acrylamido-2-methylpropanesulfonic acid to methacrylic acid was 0.8:1.2: 1.
Example 8
The only difference between this example and example 1 is that, in the preparation method of the polysiloxane crude oil demulsifier according to the embodiment of the present invention: the dosage of the N, N-bis-hexaethyleneoxy hexadecylamine and the 2-acrylamide-2-methylpropane sulfonic acid is as follows: the molar ratio of N, N-bis-hexaethyleneoxycetalkylamine, 2-acrylamido-2-methylpropanesulfonic acid to methacrylic acid was 1:0.8: 1.
Example 9
The only difference between this example and example 1 is that, in the preparation method of the polysiloxane crude oil demulsifier according to the embodiment of the present invention: the dosage of the N, N-bis-hexaethyleneoxy hexadecylamine and the 2-acrylamide-2-methylpropane sulfonic acid is as follows: the molar ratio of N, N-bis-hexaethyleneoxycetalkylamine, 2-acrylamido-2-methylpropanesulfonic acid to methacrylic acid was 1.2:0.8: 1.
Example 10
The only difference between this example and example 1 is that, in the preparation method of the polysiloxane crude oil demulsifier according to the embodiment of the present invention: the temperature of the reaction in step (3) was 60 ℃.
Example 11
The only difference between this example and example 1 is that, in the preparation method of the polysiloxane crude oil demulsifier according to the embodiment of the present invention: the temperature of the reaction in step (3) was 70 ℃.
Example 12
The only difference between this example and example 1 is that, in the preparation method of the polysiloxane crude oil demulsifier according to the embodiment of the present invention: the temperature of the reaction in step (3) was 80 ℃.
Example 13
The only difference between this example and example 1 is that, in the preparation method of the polysiloxane crude oil demulsifier according to the embodiment of the present invention: the temperature of the reaction in step (3) was 90 ℃.
Example 14
The crude oil demulsifier composition of the embodiment of the present invention comprises 50 parts by weight of the polysiloxane crude oil demulsifier prepared by the preparation method of embodiment 1, 50 parts by weight of phenolic amine resin, 70 parts by weight of polyaluminium chloride, and 4 parts by weight of cationic polyacrylamide.
Example 15
The crude oil demulsifier composition of the embodiment of the invention comprises 50 parts by weight of the polysiloxane crude oil demulsifier prepared by the preparation method of the embodiment 1, 60 parts by weight of phenolic amine resin, 70 parts by weight of polyaluminium chloride and 4 parts by weight of cationic polyacrylamide.
Example 16
The crude oil demulsifier composition of the embodiment of the invention comprises 40 parts by weight of the polysiloxane crude oil demulsifier prepared by the preparation method of the embodiment 1, 60 parts by weight of phenolic amine resin, 70 parts by weight of polyaluminium chloride and 4 parts by weight of cationic polyacrylamide.
Example 17
The crude oil demulsifier composition of the embodiment of the invention comprises 30 parts by weight of the polysiloxane crude oil demulsifier prepared by the preparation method of the embodiment 1, 54 parts by weight of phenolic amine resin, 70 parts by weight of polyaluminium chloride and 4 parts by weight of cationic polyacrylamide.
Example 18
The crude oil demulsifier composition of the embodiment of the invention comprises 30 parts by weight of the polysiloxane crude oil demulsifier prepared by the preparation method of the embodiment 1, 60 parts by weight of phenolic amine resin, 70 parts by weight of polyaluminium chloride and 4 parts by weight of cationic polyacrylamide.
Comparative example 1
A method for preparing a polysiloxane crude oil demulsifier as a comparative example of the present invention, the method comprising the steps of:
(1) mixing side chain hydrogen-containing silicone oil (PHMS), propenyl polyglycol ether and methacrylic acid in an organic solvent;
(2) heating and stirring the mixture in the nitrogen atmosphere, adding a chloroplatinic acid catalyst, continuously heating the mixture, and reacting the mixture at the temperature of 100 ℃ until the solution is transparent.
Experimental example 1
1. The demulsification performance of the demulsifiers prepared in examples 1-18 and comparative example 1 was tested.
Preparation of water-in-oil type simulated crude oil emulsion: the method comprises the following steps of preheating dehydrated crude oil and water provided by a certain petrochemical company Limited for 30min at 50 ℃ respectively to obtain crude oil with good fluidity, and mixing the water and the crude oil according to a volume ratio of 1:1 emulsifying with homogenizer (model: XHF-D, manufacturer: Ningbo Xinzhi Biotech Co., Ltd.). Setting the rotation speed of the homogenizer at 10000r/min, continuously stirring for 5 minutes, and then changing the whole system into yellow-brown uniform mixed liquid to obtain the water-in-oil type emulsion with the water content of 50 percent. And (3) heating the prepared crude oil emulsion in a water bath at 50 ℃ for one hour, wherein no water drop appears at the bottom of a beaker, and the whole system is not dehydrated and layered, which indicates that the stable water-in-oil type simulated crude oil emulsion is prepared.
Dehydration experiment: adding the crude oil demulsifier prepared in the embodiment 1 into the crude oil emulsion, placing the crude oil demulsifier into a water bath at 50 ℃ for preheating for half an hour, pouring the mixture into a colorimetric tube, metering the volume to 25mL, manually oscillating the mixture horizontally for 5 minutes to ensure that the mixed solution is fully shaken up, then placing the mixture into a constant-temperature water bath at 60 ℃ for heating and standing, and observing and recording the dehydration time and the dehydration amount. Setting a blank control group, adding 25mL of the crude oil emulsion into a 25mL colorimetric tube, heating and standing the crude oil emulsion and the colorimetric tube together in a constant-temperature water bath at 60 ℃ without adding other substances, and observing blank dehydration.
Wherein, the dosage of the crude oil demulsifier of the example 1 is 150mg/L respectively.
The volume of dehydration was measured.
And (4) calculating a result:
1. dehydration rate: w1＝V1/V×100％-W0
V1: the total dehydration amount of the system is mL; v: total water content of the system, mL; w0: blank dehydration rate,%.
2. The biodegradability of the demulsifier prepared in example 1 was tested.
Preparing oxygen-consuming sludge water with the mass concentration of suspended solids in mixed liquid activated sludge of 3000mg/LTaking 100mL of water sample, measuring the blank COD value and calculating as CODBlank space. Then 80mL of the demulsifier acetic acid solution of the example 1 with the mass concentration of 150mg/L is added into the solution, and the initial COD value is detected, namely the COD value0。
Sampling and detecting the COD value over time, and calculating the value as COD1。
Biodegradation rate of demulsifier (COD)1-CODBlank space)/COD0×100％。
3. Results of the experiment
The results of the dehydration rates of the demulsifiers of examples 1-18 and comparative example 1 are shown in table 1.
Table 1 dehydration rates of the demulsifiers of examples 1-18, comparative example 1.
| Sample (I) | Percentage of dehydration% | Sample (I) | Percentage of dehydration% |
| Example 1 | 82.9 | Example 10 | 76.4 |
| Example 2 | 72.2 | Example 11 | 80.3 |
| Example 3 | 79.3 | Example 12 | 79.6 |
| Example 4 | 75.6 | Example 13 | 75.4 |
| Example 5 | 69.4 | Example 14 | 88.5 |
| Example 6 | 72.3 | Example 15 | 91.2 |
| Example 7 | 74.5 | Example 16 | 93.2 |
| Example 8 | 78.9 | Example 17 | 89.6 |
| Example 9 | 77.5 | Example 18 | 85.4 |
| Comparative example 1 | 53.2 |
The degradation result of the demulsifier of example 1 in activated sludge is shown in fig. 1, and it can be seen from fig. 1 that the demulsifier of example 1 can be degraded by microorganisms existing in activated sludge, so that the demulsifier of the present invention has high dehydration rate and is environment-friendly.
Finally, it should be noted that the above embodiments are only used for illustrating the technical solutions of the present invention and not for limiting the protection scope of the present invention, and although the present invention is described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions can be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention.
Claims (10)
1. A preparation method of a polysiloxane crude oil demulsifier is characterized by comprising the following steps:
(1) mixing side chain hydrogen-containing silicone oil, propenyl polyglycol ether and methacrylic acid in an organic solvent;
(2) heating and stirring under the inert gas atmosphere, adding chloroplatinic acid catalyst, continuously heating, and reacting at 90-110 ℃ until the solution is transparent;
(3) cooling the transparent solution obtained in the step (2) to 60-90 ℃, adding N, N-bis-hexaethyleneoxyalkyl alkylamine, 2-acrylamide-2-methylpropanesulfonic acid and a small amount of azodiisobutyronitrile, reacting for 15-20h at 60-90 ℃ under the atmosphere of inert gas, and distilling the organic solvent at the temperature below 90 ℃ under reduced pressure to obtain a polysiloxane crude oil demulsifier;
the dosage molar ratio of the side chain hydrogen-containing silicone oil to the propenyl polyglycol ether to the methacrylic acid is 1:1-1.2: 1-1.2;
the dosage of the N, N-bis-hexaethyleneoxyalkylamine and the 2-acrylamide-2-methylpropanesulfonic acid is as follows: the molar ratio of N, N-bis-hexaethyleneoxyalkylamine, 2-acrylamido-2-methylpropanesulfonic acid to methacrylic acid is from 0.5 to 1.5: 1.
2. The method of claim 1, wherein the N, N-bis-hexaethyleneoxyalkylamine is selected from the group consisting of N, N-bis-hexaethyleneoxypentadecylamine, N-bis-hexaethyleneoxycetadecylamine, N-bis-hexaethyleneoxycetadecylamine, and N, N-bis-hexaethyleneoxyoctadecylamine.
3. The method of claim 1, wherein the method of producing N, N-bis-hexaethyleneoxyalkylamine comprises the steps of: mixing C15-C18 alkylamine, 2' -dichlorodiethyl ether, tetraethylene glycol and sodium hydroxide in a xylene solvent, heating and refluxing for 3-6 hours under nitrogen atmosphere, removing the xylene solvent, adding the obtained solid into a hot super-saturated sodium chloride solution, extracting with isopropanol, and removing the isopropanol to obtain the N, N-bis-hexaethyleneoxyalkylalkylamine.
4. The method according to claim 1, wherein the organic solvent in the step (1) is xylene or n-butanol.
5. The method according to claim 1, wherein the N, N-bis-hexaethyleneoxyalkylamine, 2-acrylamido-2-methylpropanesulfonic acid are used in amounts of: the molar ratio of N, N-bis-hexaethyleneoxyalkylamine, 2-acrylamido-2-methylpropanesulfonic acid to methacrylic acid is 0.8:0.8:1, or 0.8:1:1, or 0.8:1.2:1, or 1.2:0.8:1, or 1:1:1, or 1:0.8: 1.
6. The method according to claim 1, wherein the temperature of the reaction in the step (1) is 90 ℃, 95 ℃, 100 ℃, 105 ℃ or 110 ℃.
7. The method according to claim 1, wherein the temperature of the reaction in the step (3) is 60 ℃, 70 ℃, 75 ℃, 80 ℃ or 90 ℃.
8. A polysiloxane crude oil demulsifier prepared by the preparation method according to any one of claims 1 to 7.
9. A crude oil demulsifier composition comprising the polysiloxane crude oil demulsifier of claim 8, 30 to 50 parts by weight, 50 to 70 parts by weight of phenolic amine resin, 60 to 80 parts by weight of polyaluminum chloride, and 2 to 5 parts by weight of cationic polyacrylamide.
10. The crude oil demulsifier composition of claim 9, wherein the polysiloxane crude oil demulsifier of claim 8 and the phenolic amine-aldehyde resin are present in the crude oil demulsifier composition in a weight ratio of 1:1, 1:1.2, 1:1.5, 1:1.8, or 1: 2.
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