CN102060727A - Method for preparing long chain fatty acid polyamide based on catalysis of calcium oxide - Google Patents
Method for preparing long chain fatty acid polyamide based on catalysis of calcium oxide Download PDFInfo
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- CN102060727A CN102060727A CN2010105031614A CN201010503161A CN102060727A CN 102060727 A CN102060727 A CN 102060727A CN 2010105031614 A CN2010105031614 A CN 2010105031614A CN 201010503161 A CN201010503161 A CN 201010503161A CN 102060727 A CN102060727 A CN 102060727A
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Abstract
The invention relates to a method for preparing long chain fatty acid polyamide based on catalysis of calcium oxide, comprising the steps of adding natural oil and organic solvent into a reaction vessel firstly; dropwise adding polyethylene polyamine into the vessel; then adding calcium oxide powder into the vessel while stirring; heating reactant in the vessel; cooling the reactant to room temperature, then filtering the reactant in the container, washing, so as to obtain filtrate; and removing organic solvent in the filtrate by steaming, so as to obtain light yellow waxy solids, namely the long chain fatty acid polyamide. The catalyst in the invention can be easily removed after reaction, thus reducing process difficulty and processing cost and the method has the advantages of being efficient, simple and convenient.
Description
Technical field
The present invention relates to long-chain fat acid amides preparing technical field, be specifically related to a kind of method based on calcium oxide catalytic preparation long-chain fat acyl polyamines.
Background technology
By longer chain fatty acid and polyamines is that raw material synthetic long-chain fat acid amides is a class important chemical material, for example the long-chain fat acyl polyamines of polyethylene polyamine reaction such as longer chain fatty acid and diethylenetriamine, three second tetramines preparation is the intermediate of preparation imidazolines inhibiter, simultaneously, this class long-chain fat acyl polyamines also has surfactivity, it is the tensio-active agent of a class non-ionic type, have dispersion, solubilising, emulsification, thickening and performance such as lubricated, can be used for daily necessities and industrial auxiliary agent field.In addition, the fatty acyl polyamines can also pass through the polytype tensio-active agents of prepared in reaction such as Phosphation, sulphating, ethoxylation, sulfonation and amber acidifying.At present both at home and abroad long-chain fat acyl polyamines synthetic mainly contains three kinds of methods: one, prepared 150～180 ℃ of dehydration reactions by lipid acid and polyethylene polyamine, temperature of reaction is higher, and product color is darker, needs protection of inert gas; Two, adopt benzene,toluene,xylene as the band aqua, reacted under lower temperature by lipid acid and polyethylene polyamine and make, it is more shallow to obtain product colour; Three, by the preparation of the aminolysis reaction of vegetables oil and polyethylene polyamine, this explained hereafter cost is low, but reaction is difficult for fully, and product is the mixture of long-chain fat acyl polyamines and glycerin fatty acid ester normally.
Highly basic can improve the transformation efficiency of method three as catalyzer, catalyzer commonly used has sodium hydroxide, potassium hydroxide and sodium methylate etc., but this class catalyzer can be dissolved in reactant and the product in reaction, be difficult to after the reaction remove, increased technology difficulty and processing cost by simple method.
Summary of the invention
In order to overcome the shortcoming of above-mentioned prior art, the object of the present invention is to provide a kind of method based on calcium oxide catalytic preparation long-chain fat acyl polyamines, catalyzer is removed after reaction easily, has reduced technology difficulty and processing cost, has efficient, easy advantage.
In order to achieve the above object, the technical solution used in the present invention is:
A kind of method based on calcium oxide catalytic preparation long-chain fat acyl polyamines may further comprise the steps:
The first step, the organic solvent of natural fats and oils and 5-10 times of volume is added in the reaction vessel, natural fats and oils is the mixture of Vegetable oil lipoprotein, animal grease or arbitrary proportion, any kind Vegetable oil lipoprotein and animal grease after deacidification, dehydration, organic solvent is sherwood oil, hexanaphthene, normal hexane, benzene, toluene or dimethylbenzene
Second step, in container, drip polyethylene polyamine, the ester group mol ratio is 1-1.5 in polyethylene polyamine institute's amino-contained and the natural fats and oils: 1, and polyethylene polyamine is quadrol, diethylenetriamine, triethylene tetramine, tetraethylene pentamine, five ethene hexamines or six ethene, seven amine
In the 3rd step, stirring the granularity that adds oil quality 1-20% down in container is 10-300 order lime powder,
The 4th the step, with the reactant in the container at 60-130 ℃ of following stirring heating 1-5 hour, cool to room temperature,
The 5th step, the reactant in the container is with 1-6# sand core funnel, qualitative analysis filter paper or quantitative analysis filter paper filtering, colourless to filter residue with the organic solvent washing that is adopted in the first step, obtain filtrate,
The 6th step boiled off the organic solvent in the filtrate, obtained light yellow waxy solid, was long-chain fat acyl polyamines, and product uses the liquid-phase chromatographic analysis conversion of raw material greater than 95%.
Because the present invention has adopted calcium oxide as catalyzer, the cheap super base that belongs to of calcium oxide, its catalytic activity height, compare the solubleness of worker in organic solvent with other basic catalysts little for calcium oxide in addition, remove by filtering separation easily after the reaction, reduce technology difficulty and processing cost, had efficient, easy advantage.
The present invention can be applicable to prepare long-chain fat acyl polyamines class tensio-active agent, lubricant, dispersion agent, oil-displacing agent, emulsifying agent, crude oil by natural fats and oils and polyethylene polyamine and falls glutinous pour point depressant, crude oil wax-proofing agent, inhibiter goods and intermediate thereof.
Embodiment
Below in conjunction with specific embodiment the present invention is further described.
Embodiment 1
A kind of method based on calcium oxide catalytic preparation long-chain fat acyl polyamines may further comprise the steps:
The first step, in the organic solvent adding reaction vessel with natural fats and oils and 3 times of volumes, natural fats and oils is the soybean oil after deacidification, dehydration, organic solvent is a normal hexane,
Second step dripped polyethylene polyamine in container, the ester group mol ratio is 1.1: 1 in polyethylene polyamine institute's amino-contained and the natural fats and oils, and polyethylene polyamine is a quadrol,
In the 3rd step, stirring the granularity that adds oil quality 10% down in container is 80-100 order lime powder,
The 4th step, with the reactant in the container 65 ℃ of following stirring heating 2 hours, cool to room temperature,
The 5th step, the reactant in the container is filtered with the 4# sand core funnel, colourless with the organic solvent washing that is adopted in the first step to filter residue, obtain filtrate,
The 6th step boiled off the organic solvent in the filtrate, obtained light yellow waxy solid, was soybean oil deutero-long-chain fat acyl polyamines, and product uses the transformation efficiency of liquid-phase chromatographic analysis soybean oil greater than 98%.
Embodiment 2
A kind of method based on calcium oxide catalytic preparation long-chain fat acyl polyamines may further comprise the steps:
The first step, in the organic solvent adding reaction vessel with natural fats and oils and 5 times of volumes, natural fats and oils is the rapeseed oil after deacidification, dehydration, organic solvent is a hexanaphthene,
Second step dripped polyethylene polyamine in container, the ester group mol ratio is 1: 1 in polyethylene polyamine institute's amino-contained and the natural fats and oils, and polyethylene polyamine is a diethylenetriamine,
In the 3rd step, stirring the granularity that adds oil quality 10% down in container is 160-200 order lime powder,
The 4th step, with the reactant in the container 80 ℃ of following stirring heating 2 hours, cool to room temperature,
The 5th step, the reactant in the container is filtered with the 1# sand core funnel, colourless with the organic solvent washing that is adopted in the first step to filter residue, obtain filtrate,
The 6th step boiled off the organic solvent in the filtrate, obtained light yellow waxy solid, was rapeseed oil deutero-long-chain fat acyl polyamines, and product uses the transformation efficiency of liquid-phase chromatographic analysis rapeseed oil greater than 97%.
Embodiment 3
A kind of method based on calcium oxide catalytic preparation long-chain fat acyl polyamines may further comprise the steps:
The first step, in the organic solvent adding reaction vessel with natural fats and oils and 4 times of volumes, natural fats and oils is the Oleum Gossypii semen after deacidification, dehydration, organic solvent is a toluene,
Second step dripped polyethylene polyamine in container, the ester group mol ratio is 1: 1 in polyethylene polyamine institute's amino-contained and the natural fats and oils, and polyethylene polyamine is a triethylene tetramine,
In the 3rd step, stirring the granularity that adds oil quality 20% down in container is 40-80 order lime powder,
The 4th step, with the reactant in the container 100 ℃ of following stirring heating 3 hours, cool to room temperature,
The 5th step, the reactant in the container is filtered with the 5# sand core funnel, colourless with the organic solvent washing that is adopted in the first step to filter residue, obtain filtrate,
The 6th step boiled off the organic solvent in the filtrate, obtained light yellow waxy solid, was Oleum Gossypii semen deutero-long-chain fat acyl polyamines, and product uses the transformation efficiency of liquid-phase chromatographic analysis Oleum Gossypii semen greater than 95%.
Embodiment 4
A kind of method based on calcium oxide catalytic preparation long-chain fat acyl polyamines may further comprise the steps:
The first step, in the organic solvent adding reaction vessel with natural fats and oils and 5 times of volumes, natural fats and oils is the Viscotrol C after deacidification, dehydration, organic solvent is a dimethylbenzene,
Second step dripped polyethylene polyamine in container, the ester group mol ratio is 1.3: 1 in polyethylene polyamine institute's amino-contained and the natural fats and oils, and polyethylene polyamine is a tetraethylene pentamine,
In the 3rd step, stirring the granularity that adds oil quality 10% down in container is 80-100 order lime powder,
The 4th step, with the reactant in the container 110 ℃ of following stirring heating 3 hours, cool to room temperature,
The 5th step, the reactant in the container is filtered with the 3# sand core funnel, colourless with the organic solvent washing that is adopted in the first step to filter residue, obtain filtrate,
The 6th step boiled off the organic solvent in the filtrate, obtained light yellow waxy solid, was Viscotrol C deutero-long-chain fat acyl polyamines, and product uses the transformation efficiency of liquid-phase chromatographic analysis Viscotrol C greater than 95%.
Embodiment 5
A kind of method based on calcium oxide catalytic preparation long-chain fat acyl polyamines may further comprise the steps:
The first step, in the organic solvent adding reaction vessel with natural fats and oils and 3 times of volumes, natural fats and oils is the lard after deacidification, dehydration, organic solvent is a dimethylbenzene,
Second step dripped polyethylene polyamine in container, the ester group mol ratio is 1.2: 1 in polyethylene polyamine institute's amino-contained and the natural fats and oils, and polyethylene polyamine is five ethene hexamines,
In the 3rd step, stirring the granularity that adds oil quality 5% down in container is 160-200 order lime powder,
The 4th step, with the reactant in the container 120 ℃ of following stirring heating 1 hour, cool to room temperature,
The 5th step, the reactant in the container is filtered with the 1# sand core funnel, colourless with the organic solvent washing that is adopted in the first step to filter residue, obtain filtrate,
The 6th step boiled off the organic solvent in the filtrate, obtained light yellow waxy solid, was lard deutero-long-chain fat acyl polyamines, and product uses the transformation efficiency of liquid-phase chromatographic analysis lard greater than 98%.
Embodiment 6
A kind of method based on calcium oxide catalytic preparation long-chain fat acyl polyamines may further comprise the steps:
The first step, in the organic solvent adding reaction vessel with natural fats and oils and 10 times of volumes, natural fats and oils is 5: 1 the soybean oil and the mixture of lard for the mass ratio after deacidification, dehydration, organic solvent is a dimethylbenzene,
Second step dripped polyethylene polyamine in container, the ester group mol ratio is 1.3: 1 in polyethylene polyamine institute's amino-contained and the natural fats and oils, and polyethylene polyamine is six ethene, seven amine,
The 3rd step, stir the granularity 200-300 order lime powder that in container, adds compound lard quality 10% down,
The 4th step, with the reactant in the container 90 ℃ of following stirring heating 3 hours, cool to room temperature,
The 5th step, the qualitative analysis filter paper filtering of the reactant in the container is colourless to filter residue with the organic solvent washing that is adopted in the first step, obtain filtrate,
The 6th step boiled off the organic solvent in the filtrate, obtained light yellow waxy solid, was the mixing oil deutero-long-chain fat acyl polyamines of soybean oil and lard, and product uses the total conversion rate of liquid-phase chromatographic analysis soybean oil and lard mixing oil greater than 95%.
Embodiment 7
A kind of method based on calcium oxide catalytic preparation long-chain fat acyl polyamines may further comprise the steps:
The first step, in the organic solvent adding reaction vessel with natural fats and oils and 2 times of volumes, natural fats and oils is 1: 1 the soybean oil and the mixture of Oleum Gossypii semen for the mass ratio after deacidification, dehydration, organic solvent is a toluene,
Second step dripped polyethylene polyamine in container, the ester group mol ratio is 1.3: 1 in polyethylene polyamine institute's amino-contained and the natural fats and oils, and polyethylene polyamine is six ethene, seven amine,
The 3rd step, stir the granularity 200-300 order lime powder that in container, adds compound lard quality 5% down,
The 4th step, with the reactant in the container 100 ℃ of following stirring heating 1 hour, cool to room temperature,
The 5th step, the quantitative analysis filter paper filtering of the reactant in the container is colourless to filter residue with the organic solvent washing that is adopted in the first step, obtain filtrate,
The 6th step boiled off the organic solvent in the filtrate, obtained light yellow waxy solid, was the mixing oil deutero-long-chain fat acyl polyamines of soybean oil and Oleum Gossypii semen, and product uses the transformation efficiency of liquid-phase chromatographic analysis soybean oil and Oleum Gossypii semen mixing oil greater than 95%.
Claims (8)
1. method based on calcium oxide catalytic preparation long-chain fat acyl polyamines is characterized in that: may further comprise the steps:
The first step, the organic solvent of natural fats and oils and 1-10 times of volume is added in the reaction vessel, natural fats and oils is the mixture of Vegetable oil lipoprotein, animal grease or arbitrary proportion, any kind Vegetable oil lipoprotein and animal grease after deacidification, dehydration, organic solvent is sherwood oil, hexanaphthene, normal hexane, benzene, toluene or dimethylbenzene
Second step, in container, drip polyethylene polyamine, the ester group mol ratio is 1-1.5 in polyethylene polyamine institute's amino-contained and the natural fats and oils: 1, and polyethylene polyamine is quadrol, diethylenetriamine, triethylene tetramine, tetraethylene pentamine, five ethene hexamines or six ethene, seven amine
In the 3rd step, stirring the granularity that adds oil quality 1-20% down in container is 10-300 order lime powder,
The 4th the step, with the reactant in the container at 60-130 ℃ of following stirring heating 1-5 hour, cool to room temperature,
The 5th step, the reactant in the container is with 1-6# sand core funnel, qualitative analysis filter paper or quantitative analysis filter paper filtering, colourless to filter residue with the organic solvent washing that is adopted in the first step, obtain filtrate,
The 6th step boiled off the organic solvent in the filtrate, obtained light yellow waxy solid, was long-chain fat acyl polyamines.
2. a kind of method based on calcium oxide catalytic preparation long-chain fat acyl polyamines according to claim 1 is characterized in that: may further comprise the steps:
The first step, in the organic solvent adding reaction vessel with natural fats and oils and 3 times of volumes, natural fats and oils is the soybean oil after deacidification, dehydration, organic solvent is a normal hexane,
Second step dripped polyethylene polyamine in container, the ester group mol ratio is 1.1: 1 in polyethylene polyamine institute's amino-contained and the natural fats and oils, and polyethylene polyamine is a quadrol,
In the 3rd step, stirring the granularity that adds oil quality 10% down in container is 80-100 order lime powder,
The 4th step, with the reactant in the container 65 ℃ of following stirring heating 2 hours, cool to room temperature,
The 5th step, the reactant in the container is filtered with the 4# sand core funnel, colourless with the organic solvent washing that is adopted in the first step to filter residue, obtain filtrate,
The 6th step boiled off the organic solvent in the filtrate, obtained light yellow waxy solid, was soybean oil deutero-long-chain fat acyl polyamines.
3. a kind of method based on calcium oxide catalytic preparation long-chain fat acyl polyamines according to claim 1 is characterized in that: may further comprise the steps:
The first step, in the organic solvent adding reaction vessel with natural fats and oils and 5 times of volumes, natural fats and oils is the rapeseed oil after deacidification, dehydration, organic solvent is a hexanaphthene,
Second step dripped polyethylene polyamine in container, the ester group mol ratio is 1: 1 in polyethylene polyamine institute's amino-contained and the natural fats and oils, and polyethylene polyamine is a diethylenetriamine,
In the 3rd step, stirring the granularity that adds oil quality 10% down in container is 160-200 order lime powder,
The 4th step, with the reactant in the container 80 ℃ of following stirring heating 2 hours, cool to room temperature,
The 5th step, the reactant in the container is filtered with the 1# sand core funnel, colourless with the organic solvent washing that is adopted in the first step to filter residue, obtain filtrate,
The 6th step boiled off the organic solvent in the filtrate, obtained light yellow waxy solid, was rapeseed oil deutero-long-chain fat acyl polyamines.
4. a kind of method based on calcium oxide catalytic preparation long-chain fat acyl polyamines according to claim 1 is characterized in that: may further comprise the steps:
The first step, in the organic solvent adding reaction vessel with natural fats and oils and 4 times of volumes, natural fats and oils is the Oleum Gossypii semen after deacidification, dehydration, organic solvent is a toluene,
Second step dripped polyethylene polyamine in container, the ester group mol ratio is 1: 1 in polyethylene polyamine institute's amino-contained and the natural fats and oils, and polyethylene polyamine is a triethylene tetramine,
In the 3rd step, stirring the granularity that adds oil quality 20% down in container is 40-80 order lime powder,
The 4th step, with the reactant in the container 100 ℃ of following stirring heating 3 hours, cool to room temperature,
The 5th step, the reactant in the container is filtered with the 5# sand core funnel, colourless with the organic solvent washing that is adopted in the first step to filter residue, obtain filtrate,
The 6th step boiled off the organic solvent in the filtrate, obtained light yellow waxy solid, was Oleum Gossypii semen deutero-long-chain fat acyl polyamines.
5. a kind of method based on calcium oxide catalytic preparation long-chain fat acyl polyamines according to claim 1 is characterized in that: may further comprise the steps:
The first step, in the organic solvent adding reaction vessel with natural fats and oils and 5 times of volumes, natural fats and oils is the Viscotrol C after deacidification, dehydration, organic solvent is a dimethylbenzene,
Second step dripped polyethylene polyamine in container, the ester group mol ratio is 1.3: 1 in polyethylene polyamine institute's amino-contained and the natural fats and oils, and polyethylene polyamine is a tetraethylene pentamine,
In the 3rd step, stirring the granularity that adds oil quality 10% down in container is 80-100 order lime powder,
The 4th step, with the reactant in the container 110 ℃ of following stirring heating 3 hours, cool to room temperature,
The 5th step, the reactant in the container is filtered with the 3# sand core funnel, colourless with the organic solvent washing that is adopted in the first step to filter residue, obtain filtrate,
The 6th step boiled off the organic solvent in the filtrate, obtained light yellow waxy solid, was Viscotrol C deutero-long-chain fat acyl polyamines.
6. a kind of method based on calcium oxide catalytic preparation long-chain fat acyl polyamines according to claim 1 is characterized in that: may further comprise the steps:
The first step, in the organic solvent adding reaction vessel with natural fats and oils and 3 times of volumes, natural fats and oils is the lard after deacidification, dehydration, organic solvent is a dimethylbenzene,
Second step dripped polyethylene polyamine in container, the ester group mol ratio is 1.2: 1 in polyethylene polyamine institute's amino-contained and the natural fats and oils, and polyethylene polyamine is five ethene hexamines,
In the 3rd step, stirring the granularity that adds oil quality 5% down in container is 160-200 order lime powder,
The 4th step, with the reactant in the container 120 ℃ of following stirring heating 1 hour, cool to room temperature,
The 5th step, the reactant in the container is filtered with the 1# sand core funnel, colourless with the organic solvent washing that is adopted in the first step to filter residue, obtain filtrate,
The 6th step boiled off the organic solvent in the filtrate, obtained light yellow waxy solid, was lard deutero-long-chain fat acyl polyamines.
7. a kind of method based on calcium oxide catalytic preparation long-chain fat acyl polyamines according to claim 1 is characterized in that: may further comprise the steps:
The first step, in the organic solvent adding reaction vessel with natural fats and oils and 10 times of volumes, natural fats and oils is 5: 1 the soybean oil and the mixture of lard for the mass ratio after deacidification, dehydration, organic solvent is a dimethylbenzene,
Second step dripped polyethylene polyamine in container, the ester group mol ratio is 1.3: 1 in polyethylene polyamine institute's amino-contained and the natural fats and oils, and polyethylene polyamine is six ethene, seven amine,
The 3rd step, stir the granularity 200-300 order lime powder that in container, adds compound lard quality 10% down,
The 4th step, with the reactant in the container 90 ℃ of following stirring heating 3 hours, cool to room temperature,
The 5th step, the qualitative analysis filter paper filtering of the reactant in the container is colourless to filter residue with the organic solvent washing that is adopted in the first step, obtain filtrate,
The 6th step boiled off the organic solvent in the filtrate, obtained light yellow waxy solid, was the mixing oil deutero-long-chain fat acyl polyamines of soybean oil and lard.
8. a kind of method based on calcium oxide catalytic preparation long-chain fat acyl polyamines according to claim 1 is characterized in that: may further comprise the steps:
The first step, in the organic solvent adding reaction vessel with natural fats and oils and 2 times of volumes, natural fats and oils is 1: 1 the soybean oil and the mixture of Oleum Gossypii semen for the mass ratio after deacidification, dehydration, organic solvent is a toluene,
Second step dripped polyethylene polyamine in container, the ester group mol ratio is 1.3: 1 in polyethylene polyamine institute's amino-contained and the natural fats and oils, and polyethylene polyamine is six ethene, seven amine,
The 3rd step, stir the granularity 200-300 order lime powder that in container, adds compound lard quality 5% down,
The 4th step, with the reactant in the container 100 ℃ of following stirring heating 1 hour, cool to room temperature,
The 5th step, the quantitative analysis filter paper filtering of the reactant in the container is colourless to filter residue with the organic solvent washing that is adopted in the first step, obtain filtrate,
The 6th step boiled off the organic solvent in the filtrate, obtained light yellow waxy solid, was the mixing oil deutero-long-chain fat acyl polyamines of soybean oil and Oleum Gossypii semen.
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Cited By (6)
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| CN102443124A (en) * | 2011-09-21 | 2012-05-09 | 西安石油大学 | Preparation method and application of multifunctional polyamine amide for oil field |
| CN102698649A (en) * | 2012-05-17 | 2012-10-03 | 郑州轻工业学院 | Acyl-containing complexing surface active agent and synthesis method thereof |
| CN103433014A (en) * | 2013-09-04 | 2013-12-11 | 西安石油大学 | Preparation method of alkoxy surface modified calcium oxide solid superbase |
| CN104805444A (en) * | 2014-01-29 | 2015-07-29 | 中石化洛阳工程有限公司 | Low-temperature corrosion inhibitor and preparation method thereof |
| CN110746953A (en) * | 2019-11-07 | 2020-02-04 | 西安石油大学 | Viscosity-reducing and asphalt-stabilizing agent for thickened oil and preparation method thereof |
| CN110819330A (en) * | 2019-11-18 | 2020-02-21 | 西安石油大学 | Phosphonate type oil-gas field surfactant derived from natural oil |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102443124A (en) * | 2011-09-21 | 2012-05-09 | 西安石油大学 | Preparation method and application of multifunctional polyamine amide for oil field |
| CN102698649A (en) * | 2012-05-17 | 2012-10-03 | 郑州轻工业学院 | Acyl-containing complexing surface active agent and synthesis method thereof |
| CN103433014A (en) * | 2013-09-04 | 2013-12-11 | 西安石油大学 | Preparation method of alkoxy surface modified calcium oxide solid superbase |
| CN103433014B (en) * | 2013-09-04 | 2015-09-02 | 西安石油大学 | The preparation method of alkoxyl surface modification calcium oxide solid super base |
| CN104805444A (en) * | 2014-01-29 | 2015-07-29 | 中石化洛阳工程有限公司 | Low-temperature corrosion inhibitor and preparation method thereof |
| CN110746953A (en) * | 2019-11-07 | 2020-02-04 | 西安石油大学 | Viscosity-reducing and asphalt-stabilizing agent for thickened oil and preparation method thereof |
| CN110746953B (en) * | 2019-11-07 | 2022-05-10 | 西安石油大学 | Viscosity-reducing and asphalt-stabilizing agent for thickened oil and preparation method thereof |
| CN110819330A (en) * | 2019-11-18 | 2020-02-21 | 西安石油大学 | Phosphonate type oil-gas field surfactant derived from natural oil |
| CN110819330B (en) * | 2019-11-18 | 2022-05-10 | 西安石油大学 | Phosphonate type oil-gas field surfactant derived from natural oil |
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Application publication date: 20110518 |