CN106883343A - A kind of preparation method containing ionic liquid pour point depressant - Google Patents
A kind of preparation method containing ionic liquid pour point depressant Download PDFInfo
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- CN106883343A CN106883343A CN201710156252.7A CN201710156252A CN106883343A CN 106883343 A CN106883343 A CN 106883343A CN 201710156252 A CN201710156252 A CN 201710156252A CN 106883343 A CN106883343 A CN 106883343A
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- ionic liquid
- pour point
- point depressant
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/588—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 polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
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Abstract
The invention discloses a kind of preparation method containing ionic liquid pour point depressant, it is specially:Step one, to adding octadecyl acrylate, styrene, maleic anhydride and vinyl ionic liquid in the reactor with magnetic stirrer, reflux condenser and nitrogen ingress pipe；Step 2 and then to N is added in reactor, N dimethylformamides are used as solvent；Step 3, it is warming up to 70 85 DEG C of reaction temperature；Step 4, precipitated；Step 5, it is vacuum dried；Step 6, crushed with pulverizer and filter out the product that granularity is 80 mesh, you can obtain finished product.Beneficial effect：Its nonpolar moiety and wax cocrystallization, and polarity link then makes the brilliant crystal formation of wax produce distortion, unfavorable wax crystalline substance continues to grow up to form network structure, and simultaneous ionic liquid assigns pour point depression agent molecule upper band electric charge, prevents wax crystalline substance to be interconnected to form tridimensional network.
Description
Technical field
The present invention relates to a kind of preparation method of pour point depressant for crude oil, more particularly to a kind of pour point depression of high-wax oil containing ionic liquid
The preparation method of agent.
Background technology
At present, the crude oil of China's main oilfield production is nearly all high-wax oil, and chemical agent pour point depression method is using addition high score
The chemical treatments of sub- polymer, with reach pour point depression, improve crude oil low temperature flow purpose, this be realize normal temperature conveying and
Improve one of effective way that crude oil shutdown is restarted.
Pour-point depressant mainly has surfactant type, polymer-type and Compositional type copolymer type.Polymer electrolyte pour-point depressant is most
Number is oil-soluble, is the branched polymer polymer of the alkyl chain link containing similar paraffin and polarity chain link.When using,
It is proportionally mixed with crude oil at a certain temperature.Say that this kind of pour-point depressant is by change crude oil from broadest scope
Wax crystallization form, make wax connected between being difficult to be formed three-dimensional space network structure at normal temperatures to prevent paraffin molecule gel or
Coalescence is blocking, so as to prevent the deposition of wax, reaches the effect for reducing condensation point of crude oil.
What is be most widely used now is the pour-point depressant of EVA and its modifier, polyethylene and polyacrylate polymers,
EVA and the vinyl acetate esters polymer of polyethylene one, such pour-point depressant have strong specific aim to crude oil, certain when selecting
It is noted that the average carbon number that the carbon number of oleophylic carbochain will be brilliant with wax in crude oil in EVA is substantially close to and carbon number distribution also should be basic
Unanimously, best effects can just be received.Such pour-point depressant does not have enough side chains to carry out eutectic with wax crystalline substance, so depression effeCt is not
It is highly desirable.
The content of the invention
The purpose of the present invention is directed to wax partial crystallization during high-wax oil easily causes oil in exploitation and course of conveying and goes out blocking adopts
A kind of problem of oil pipe and petroleum pipeline, there is provided preparation method containing ionic liquid pour point depressant.
The preparation method containing ionic liquid pour point depressant that the present invention is provided, it is comprised the following steps that:
Step one, in the reactor with magnetic stirrer, reflux condenser and nitrogen ingress pipe add acrylic acid ten
Octaester, styrene, maleic anhydride and vinyl ionic liquid, four kinds of monomer molar proportionings are (1-3):(1-6):(0.5-2)：
(0.01-0.8)；
Step 2 then in reactor add DMF as solvent, then heat to 40-50 DEG C,
Stirring dissolves it under nitrogen atmosphere；
Step 3,70-85 DEG C of reaction temperature is warming up to, reacts and flowed back, initiator azo is then added in three times
Bis-isobutyronitrile, reacts 12h；
After step 4, reaction terminate, room temperature is cooled to, is subsequently adding methyl alcohol, precipitated；
Filtered after the completion of step 5, precipitation, and washed for several times with methyl alcohol, be then vacuum dried；
After the completion of step 6, drying, the product that granularity is 80 mesh is crushed and filtered out with pulverizer, you can obtain finished product.
Ionic liquid in step one is 1- vinyl -3- octylimidazoles tetrafluoroborate, 1- vinyl -3- butyl imidazoles
One or several in double fluoroforms Huang imide salts or 1- vinyl -3- octylimidazole hexafluorophosphates, in step one also
Surfactant sulfonated castor oil can be added to improve the compatibility of monomer, its consumption accounts for the 0-0.8% of gross mass.
In step 2, the addition of DMF is more than 1.5 times of reactant gross mass, in step 2,
It is preferred that being warming up to 50 DEG C, stirring dissolves it.
In step 3, initiator azobisisobutyronitrile accounts for the 1% of gross mass, in three times plus, every time plus ratio for 30%,
40%th, 30%, in step 3,80 DEG C of reaction temperature is preferably warming up to, react 12h.
In step 4, the addition of methyl alcohol is 3 times of reactant gross mass, and in step 4, vacuum drying temperature is 60
DEG C, the time is 8 hours.
Four kinds of monomers, existing side chain are used to be crystallized with wax crystalline substance in the present invention, but polarized part prevents the brilliant aggregation of wax,
Ionic liquid is added simultaneously, makes pour-point depressant in oil still with electric charge, can further prevent the brilliant formation of wax three-dimensional netted
Structure.Octadecyl acrylate provides side chain, styrene and maleic anhydride can the effectively brilliant aggregation of wax control, ionic liquid assigns and gathering
Compound carries certain electric charge, makes have certain repulsive interaction between wax crystalline substance.
Beneficial effects of the present invention：
Pour-point depressant prepared by the present invention has nonpolar moiety, polar portion and electrically charged part.Its nonpolar moiety
With wax cocrystallization, and polarity link then makes the brilliant crystal formation of wax produce distortion, and unfavorable wax crystalline substance continues to grow up and to form network structure, together
When the ionic liquid that exists assign pour point depression agent molecule upper band and have electric charge, prevent wax crystalline substance to be interconnected to form tridimensional network.
Specific embodiment
The present invention prepare pour-point depressant with traditional pour-point depressant compared with maximum difference with introduce in oil product still
So the ionic liquid with electric charge, makes pour point depression agent molecule avoid the formation of three dimensional network due to mutually exclusive effect on wax crystalline substance surface
Network.
Through practical application, pour point depression amplitude measure is carried out, as a result show that pour-point depressant of the invention has good depression effeCt.
The following examples are described in further detail to of the invention.
Embodiment 1：
The preparation method containing ionic liquid pour point depressant that the present invention is provided, it is comprised the following steps that:
Step one, to magnetic stirrer, acrylic acid ten is added in the reactor of reflux condenser and nitrogen ingress pipe
Octaester 30g, styrene 10g, maleic anhydride 5g and 1- vinyl -3- octylimidazole tetrafluoroborates 1.5g；
Step 2 and then toward adding in reactor DMF as solvent, then heats to 50 DEG C, nitrogen
Stirring dissolves it under atmosphere；
Step 3,80 DEG C of reaction temperature is warming up to, reacts and flowed back, then add initiator azo two different in three times
Ding Jing, reacts 12h；
After step 4, reaction terminate, room temperature is cooled to, is subsequently adding methyl alcohol, precipitated；
Filtered after the completion of step 5, precipitation, and washed for several times with methyl alcohol, be then vacuum dried；
After the completion of step 6, drying, the product that granularity is 80 mesh is crushed and filtered out with pulverizer, you can obtain finished product.
In step 2, the addition of DMF is 110g.
Step 3, in, initiator azobisisobutyronitrile accounts for the 1% of gross mass, adds in three times, adding proportion be 0.33g,
0.44g、0.33g。
Step 4, in, the addition of methyl alcohol is 3 times of reactant gross mass, i.e. 110g is vacuum drying in step 4
Temperature is 80 DEG C, and the time is 8 hours.
Embodiment 2：
The preparation method containing ionic liquid pour point depressant that the present invention is provided, it is comprised the following steps that:
Step one, to magnetic stirrer, acrylic acid ten is added in the reactor of reflux condenser and nitrogen ingress pipe
The double fluoroform Huang imide salts of octaester, maleic anhydride and 1- vinyl -3- butyl imidazoles, wherein octadecyl acrylate, benzene second
The quality of the monomer of the double fluoroform Huang imide salts of alkene, maleic anhydride and 1- vinyl -3- butyl imidazoles is respectively：10g,
6g, 2g, 1.3g；
Step 2 and then toward adding in reactor DMF as solvent, then heats to 40 DEG C, nitrogen
Stirring dissolves it under atmosphere.
Step 3,70 DEG C of reaction temperature is warming up to, reacts and flowed back, then add initiator azo two different in three times
Ding Jing, reacts 8h；
After step 4, reaction terminate, room temperature is cooled to, is subsequently adding methyl alcohol, precipitated；
Filtered after the completion of step 5, precipitation, and washed for several times with methyl alcohol, be then vacuum dried；
After the completion of step 6, drying, the product of 80 mesh is crushed and filtered out with pulverizer, you can obtain finished product.
In step 2, the addition of DMF is reactant gross mass.
In step 3, account for gross mass the 1% of initiator azobisisobutyronitrile, add in three times, respectively 0.06g,
0.08g and 0.06g.
In step 4, the addition of methyl alcohol is about 5 times of reactant gross mass, i.e. 100g is vacuum drying in step 4
Temperature is 80 DEG C, and the time is 8 hours.
Embodiment 3：
The preparation method containing ionic liquid pour point depressant that the present invention is provided, it is comprised the following steps that:
Step one, to magnetic stirrer, acrylic acid ten is added in the reactor of reflux condenser and nitrogen ingress pipe
Octaester, styrene, maleic anhydride and 1- vinyl -3- octylimidazole tetrafluoroborates, wherein octadecyl acrylate, maleic anhydride
Quality with 1- vinyl -3- octylimidazole hexafluorophosphates is respectively 6.5g, 3.1g, 1.0g and 1.8g；
Step 2 and then toward adding in reactor DMF as solvent, then heats to 50 DEG C, nitrogen
Stirring dissolves it under atmosphere.
Step 3,80 DEG C of reaction temperature is warming up to, reacts and flowed back, then add initiator azo two different in three times
Ding Jing, reacts 12h；
After step 4, reaction terminate, room temperature is cooled to, is subsequently adding methyl alcohol, precipitated；
Filtered after the completion of step 5, precipitation, and washed for several times with methyl alcohol, be then vacuum dried；
After the completion of step 6, drying, the product of 80 mesh is crushed and filtered out with pulverizer, you can obtain finished product.
In step 2, the addition of DMF is 25g.
In step 3, total addition of initiator azobisisobutyronitrile is 1%, is added in three times, respectively 0.36g,
0.48g and 0.36g.
In step 4, the addition of methyl alcohol is 37g, and vacuum drying temperature is 80 DEG C in step 4, and the time is 8 hours.
Specific evaluation method and result：
This wax control is determined according to professional standard《SY/T 5767-2005 recover the oil with clear, pour-point depressant technical conditions》Middle regulation
Perform, result of the test and calculating are also according to the standard operation.Using device for determining crude oil congealing point, add after heating melts crude oil
Enter, then crude oil is solidified by reducing temperature, so as to determine its condensation point.
The pour point depression of crude oil effectiveness results table of table 1.：
Claims (5)
1. a kind of preparation method containing ionic liquid pour point depressant, it is characterised in that：It is comprised the following steps that:
Step one, in the reactor with magnetic stirrer, reflux condenser and nitrogen ingress pipe add octadecyl acrylate,
Styrene, maleic anhydride and vinyl ionic liquid, four kinds of monomer molar proportionings are (1-3):(1-6):(0.5-2)：(0.01-
0.8)；
Step 2 then in reactor add DMF as solvent, then heat to 40-50 DEG C, nitrogen
Stirring dissolves it under atmosphere；
Step 3,70-85 DEG C of reaction temperature is warming up to, reacts and flowed back, then add initiator azo two different in three times
Butyronitrile, reacts 12h；
After step 4, reaction terminate, room temperature is cooled to, is subsequently adding methyl alcohol, precipitated；
Filtered after the completion of step 5, precipitation, and washed for several times with methyl alcohol, be then vacuum dried；
After the completion of step 6, drying, the product that granularity is 80 mesh is crushed and filtered out with pulverizer, you can obtain finished product.
2. a kind of preparation method containing ionic liquid pour point depressant according to claim 1, it is characterised in that：Institute
Ionic liquid in the step of stating is 1- vinyl -3- octylimidazoles tetrafluoroborate, 1- vinyl -3- butyl imidazoles double three
Fluoromethane Huang imide salts or 1- vinyl -3- octylimidazole hexafluorophosphates in one or several, can also in step one
Add surfactant sulfonated castor oil to improve the compatibility of monomer, its consumption accounts for the 0-0.8% of gross mass.
3. a kind of preparation method containing ionic liquid pour point depressant according to claim 1, it is characterised in that：Institute
In the step of stating two, the addition of DMF is more than 1.5 times of reactant gross mass, in step 2, preferably
50 DEG C are warming up to, stirring dissolves it.
4. a kind of preparation method containing ionic liquid pour point depressant according to claim 1, it is characterised in that：Institute
In the step of stating three, initiator azobisisobutyronitrile accounts for the 1% of gross mass, in three times plus, every time plus ratio for 30%,
40%th, 30%, in step 3,80 DEG C of reaction temperature is preferably warming up to, react 12h.
5. a kind of preparation method containing ionic liquid pour point depressant according to claim 1, it is characterised in that：Institute
In the step of stating four, the addition of methyl alcohol is 3 times of reactant gross mass, and in step 4, vacuum drying temperature is 60 DEG C, when
Between be 8 hours.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112779075A (en) * | 2021-01-21 | 2021-05-11 | 敬青梅 | Durable lubricating oil with long service life |
| CN114560964A (en) * | 2022-01-26 | 2022-05-31 | 贵州大学 | Synthetic method and application of carboxyl functional polyion liquid |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012072395A (en) * | 2010-08-30 | 2012-04-12 | Nippon Nyukazai Kk | Treating agent |
| CN103184043A (en) * | 2013-02-28 | 2013-07-03 | 大连大学 | Crude oil pour point depressant and preparation method thereof |
| JP2013256499A (en) * | 2011-11-28 | 2013-12-26 | Nippon Nyukazai Kk | Ion liquid and antistatic agent, antifog agent, dispersant or emulsifier, lubricant, electrolytic solution and cellulose dissolving agent, each containing the same, |
| CN104447324A (en) * | 2014-11-04 | 2015-03-25 | 大连东方创新科技有限公司 | Arylalkyl methacrylate as well as preparation method and application thereof |
| CN104927971A (en) * | 2015-05-13 | 2015-09-23 | 南京欧美加新材料有限公司 | Preparation method for lubricating oil composition containing ionic liquid, modified nanometer copper powder and graphene |
-
2017
- 2017-03-16 CN CN201710156252.7A patent/CN106883343B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012072395A (en) * | 2010-08-30 | 2012-04-12 | Nippon Nyukazai Kk | Treating agent |
| JP2013256499A (en) * | 2011-11-28 | 2013-12-26 | Nippon Nyukazai Kk | Ion liquid and antistatic agent, antifog agent, dispersant or emulsifier, lubricant, electrolytic solution and cellulose dissolving agent, each containing the same, |
| CN103184043A (en) * | 2013-02-28 | 2013-07-03 | 大连大学 | Crude oil pour point depressant and preparation method thereof |
| CN104447324A (en) * | 2014-11-04 | 2015-03-25 | 大连东方创新科技有限公司 | Arylalkyl methacrylate as well as preparation method and application thereof |
| CN104927971A (en) * | 2015-05-13 | 2015-09-23 | 南京欧美加新材料有限公司 | Preparation method for lubricating oil composition containing ionic liquid, modified nanometer copper powder and graphene |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112779075A (en) * | 2021-01-21 | 2021-05-11 | 敬青梅 | Durable lubricating oil with long service life |
| CN112779075B (en) * | 2021-01-21 | 2022-06-21 | 辽宁汽众润滑油生产有限公司 | Durable lubricating oil with long service life |
| CN114560964A (en) * | 2022-01-26 | 2022-05-31 | 贵州大学 | Synthetic method and application of carboxyl functional polyion liquid |
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