CN101619209B - New application and composition of amide sodium sulfonate as oil field additive - Google Patents
New application and composition of amide sodium sulfonate as oil field additive Download PDFInfo
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Abstract
The invention discloses application of amide sulphonic acid presented in a general expression I or salt thereof to the reduction of crude oil viscosity, a composition containing the amide sulphonic acid or the salt thereof and a chemical reagent selected from triethylamine, lignosulphonates or polyoxyethylene polyoxypropylene alkyl phenol ether presented in a general expression II, application of the composition to the reduction of the crude oil viscosity, and a method of reducing the crude oil viscosity by using the amide sulphonic acid presented in the general expression I or the salt thereof. R1-R3 and M in the general expression I and R and a/b in the general expression II are defined in the text.
Description
Technical field
The present invention relates to amide group sulfonic acid or its salt and the composition and their purposes in crude oil production, wellbore lift and conveying that contain amide group sulfonic acid or its salt, particularly their purposes in the preparation oil field additive.
Background technology
The quantity of the resin and asphalt that contains in the underground crude oil of containing directly affects the viscosity of crude oil.Crude oil in the crude oil of China more than 60% belongs to the viscous crude that contains resin and asphalt.The viscous crude field that has been found that at present mainly is distributed in the oil fields such as the Liaohe River, Xinjiang, triumph, Henan, huge port, Jilin.
In crude oil production, wellbore lift and course of conveying, because viscosity of crude is large, particularly when crude oil contained certain water, along with crude oil flow, it is more and more thicker that crude oil can become.Because viscosity of crude is large, in exploitation, wellbore lift and course of conveying, it adsorbs consumingly to bottom and wall, and this not only makes the resistance of crude oil production and conveying increase, and has had a strong impact on recovery ratio and the transport efficiency of crude oil.
Along with increasing rapidly of Chinese national economy, the demand of oil is also being increased day by day.To reducing viscosity of crude and crude oil production and transporting resistance, improve oil recovery factor and transport efficiency and have higher requirement.
Although developed the method for polytype reduction viscosity of crude to be used for exploitation, wellbore lift and conveying crude oil, for example, mix thin oil method, heating method and chemical viscosity reduction method, but still need the viscosity that new viscosity reducing process and new viscosity-depression agent reduce crude oil badly, change the mobility of crude oil, to be easy to exploitation, wellbore lift and conveying crude oil.
Summary of the invention
One aspect of the present invention relates to the amide group sulfonic acid shown in general formula I or its salt reducing viscosity of crude, particularly reduces the purposes in viscosity of thickened oil,
General formula I
R
1For containing straight chain or C side chain of at least one two key
12-C
25Thiazolinyl;
R
2C for straight or branched
1-C
8Alkyl;
R
3C for straight or branched
1-C
8Alkylidene group;
M is selected from hydrogen, ammonium ion and metallic cation, and described metallic cation is selected from sodium, potassium, lithium, calcium, magnesium, aluminium, iron, zinc, copper and manganese.
In one embodiment, R
1C for the straight or branched that contains two keys
12-C
25Thiazolinyl; R
2C for straight or branched
1-C
8Alkyl; R
3C for straight or branched
1-C
8Alkylidene group; M is selected from hydrogen, ammonium ion and metallic cation, and described metallic cation is selected from sodium, potassium, lithium, calcium and magnesium.
In another embodiment, R
1C for the straight or branched that contains two keys
15-C
23Thiazolinyl; R
2C for straight or branched
1-C
6Alkyl; R
3C for straight or branched
1-C
6Alkylidene group; M is selected from hydrogen, ammonium ion and metallic cation, and described metallic cation is selected from sodium and potassium.
The present invention relates to composition on the other hand, the chemical reagent that it comprises the amide group sulfonic acid shown in as hereinbefore defined general formula I or its salt and is selected from the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in triethylamine, Sulfite lignin or general formula I I,
General formula I I
R：H
3C-(CH
2)n- n＝7-17
a/b＝50％～100％。
In one embodiment, described composition comprises above the amide group sulfonic acid shown in defined general formula I or its salt and triethylamine, and based on the gross weight of described composition, the content of described amide group sulfonic acid or its salt is the about about 99w/w% of 70w/w%-, preferred approximately 77w/w%-is 96w/w% approximately, more preferably from about the about 92w/w% of 82w/w%-.
In another embodiment, described composition comprises above the amide group sulfonic acid shown in defined general formula I or its salt and Sulfite lignin, and based on the gross weight of described composition, the content of described amide group sulfonic acid or its salt is the about about 95w/w% of 5w/w%-, preferred approximately 35w/w%-is 70w/w% approximately, more preferably from about the about 60w/w% of 40w/w%-.
In another embodiment, described composition comprises the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in the amide group sulfonic acid shown in defined general formula I above or its salt and general formula I I, and based on the gross weight of described composition, the content of described amide group sulfonic acid or its salt is the about about 95w/w% of 5w/w%-, preferred approximately 30w/w%-is 75w/w% approximately, more preferably from about the about 60w/w% of 40w/w%-.
In another embodiment, in the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in described general formula I I, n=7-11 and a/b=50%～95%.
The present invention relates to above-mentioned composition on the other hand reducing viscosity of crude, particularly reduces the purposes in viscosity of thickened oil.
Another aspect of the present invention also relates to the method that reduces viscosity of crude, and described method comprises the steps:
(1) the amide group sulfonic acid shown in general formula I defined above or its salt are mixed with water, form the aqueous solution;
(2) aqueous solution that obtains in step (1) is mixed to reduce viscosity of crude with crude oil.
In one embodiment, also comprise the step of adding the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in triethylamine, Sulfite lignin or general formula I I defined above in described step (1).
In one embodiment, the total concn of the aqueous solution that obtains in step (1) is about about 5.0% (w/w) of 0.01%-, and preferred approximately 0.02%-approximately 3.0%, and more preferably from about 0.04%-approximately 2.0%, and most preferably from about 0.04%-approximately 1.5%.
In another embodiment, the aqueous solution that obtains in crude oil and step (1), is more preferably less than the mass ratio that equals approximately 65: 35 and mixes preferably less than or equal to approximately 75: 25 with less than or equal to approximately 90: 10.
Detailed description of the invention
In the above-mentioned definition and embodiment hereinafter described of the amide group sulfonic acid shown in general formula I or its salt, term used herein has following implication:
Term " thiazolinyl " refers to the aliphatic hydrocarbon group of the straight or branched that contains at least one unsaturated double-bond that is comprised of carbon atom and hydrogen atom, and it is connected with the rest part of molecule by singly-bound.Described thiazolinyl has approximately 12 to about 25 carbon atoms, preferred 15-23 carbon atom, more preferably 15-20 carbon atom.Described thiazolinyl preferably has a unsaturated double-bond.The limiting examples of described thiazolinyl includes but not limited to tridecylene base, tetradecene base, hexadecylene base, icosa alkene base, two tetradecene bases, 24 pentaene bases etc.
Term " alkyl " refers to the aliphatic hydrocarbon group of the saturated straight or branched that is comprised of carbon atom and hydrogen atom, and it is connected with the rest part of molecule by singly-bound.Described alkyl has 1-8 carbon atom, preferred 1-6 carbon atom, more preferably 1-4 carbon atom, most preferably 1-2 carbon atom.The limiting examples of described alkyl includes but not limited to such as methyl, ethyl, propyl group, 2-propyl group, normal-butyl, isobutyl-, tert-butyl, just-amyl group, 2-methyl butyl, neo-pentyl, n-hexyl, 2-methyl hexyl etc.
Term " alkylidene group " only refers to the bivalent hydrocarbon chain of the saturated straight or branched of the rest part of the connection molecule that is comprised of with hydrogen atom carbon atom and residue groups.Described alkylidene group has 1-8 carbon atom, and preferred 1-6 is carbon atom, more preferably 1-4 carbon atom.Described alkylidene group is preferably the alkylidene group of straight chain.The limiting examples of described alkyl includes but not limited to methylene radical, ethylidene, propylidene, butylidene, pentylidene, hexylidene, inferior heptyl and octylene etc.
Term " ammonium ion " refers to formula-NH
4Group.
Term " Sulfite lignin " refers to ammonium salt, an alkali metal salt and the alkaline earth salt of lignosulfonic acid.The limiting examples of Sulfite lignin comprises ammonium lignin sulfonate, sodium lignosulfonate, lignin sulfonic acid potassium, lignosulfonic acid magnesium, calcium lignosulfonate etc.
An aspect of of the present present invention relates to the amide group sulfonic acid shown in general formula I or its salt reducing viscosity of crude, particularly reduces the purposes in viscosity of thickened oil,
Wherein
R
1For containing straight chain or C side chain of at least one two key
12-C
25Thiazolinyl;
R
2C for straight or branched
1-C
8Alkyl;
R
3C for straight or branched
1-C
8Alkylidene group;
M is selected from hydrogen, ammonium ion and metallic cation, and described metallic cation is selected from sodium, potassium, lithium, calcium, magnesium, aluminium, iron, zinc, copper and manganese.
In one embodiment, R
1For containing straight chain or C side chain of at least one two key
15-C
23Thiazolinyl; In another embodiment, R
1For containing straight chain or C side chain of at least one two key
15-C
20Thiazolinyl; In another embodiment, R
1For containing straight chain or C side chain of two keys
12-C
25Thiazolinyl; In another embodiment, R
1For containing straight chain or C side chain of two keys
15-C
23Thiazolinyl; In another embodiment, R
1For containing straight chain or C side chain of two keys
15-C
20Thiazolinyl; In another embodiment, R
1C for the straight chain that contains two keys
12-C
25Thiazolinyl; In another embodiment, R
1C for the straight chain that contains two keys
15-C
23Thiazolinyl; In another embodiment, R
1C for the straight chain that contains two keys
15-C
20Thiazolinyl.
In one embodiment, R
2C for straight or branched
1-C
6Alkyl; In another embodiment, R
2C for straight or branched
1-C
4Alkyl; In another embodiment, R
2C for straight chain
1-C
8Alkyl; In another embodiment, R
2C for straight chain
1-C
6Alkyl; In another embodiment, R
2C for straight chain
1-C
4Alkyl; In another embodiment, R
2Be C
1-C
2Alkyl.
In one embodiment, R
3C for straight or branched
1-C
6Alkylidene group; In another embodiment, R
3C for straight or branched
1-C
4Alkylidene group; In another embodiment, R
3C for straight chain
1-C
8Alkylidene group; In another embodiment, R
3C for straight chain
1-C
6Alkylidene group; In another embodiment, R
3C for straight chain
1-C
4Alkylidene group.In another embodiment, R
3Be C
1-C
2Alkylidene group.
In one embodiment, M is selected from hydrogen, ammonium ion and described metal ion, and described metallic cation is selected from sodium, potassium, lithium, calcium, magnesium and aluminium.In one embodiment, M is selected from hydrogen, ammonium ion and described metal ion, and described metallic cation is selected from sodium, potassium, lithium, calcium and magnesium.In one embodiment, M is selected from hydrogen, ammonium ion and described metal ion, and described metallic cation is selected from sodium and potassium.In one embodiment, M is selected from hydrogen, ammonium ion and described metal ion, and described metallic cation is selected from sodium.
In one embodiment, R
1C for the straight or branched that contains two keys
12-C
25Thiazolinyl; R
2C for straight or branched
1-C
8Alkyl; R
3C for straight or branched
1-C
8Alkylidene group; M is hydrogen, ammonium ion or metallic cation, and described metallic cation is selected from sodium, potassium, lithium, calcium and magnesium.
In another embodiment, R
1C for the straight or branched that contains two keys
15-C
23Thiazolinyl; R
2C for straight or branched
1-C
6Alkyl; R
3C for straight or branched
1-C
6Alkylidene group; M is hydrogen, ammonium ion or metallic cation, and described metallic cation is selected from sodium, potassium, lithium, calcium and magnesium.
In another embodiment, R
1C for the straight or branched that contains two keys
15-C
20Thiazolinyl; R
2C for straight or branched
1-C
4Alkyl; R
3C for straight or branched
1-C
4Alkylidene group; M is hydrogen, ammonium ion or metallic cation, and described metallic cation is selected from sodium and potassium.
In one embodiment, R
1C for the straight chain that contains two keys
12-C
25Thiazolinyl; R
2C for straight chain
1-C
8Alkyl; R
3C for straight chain
1-C
8Alkylidene group; M is hydrogen, ammonium ion or metallic cation, and described metallic cation is selected from sodium, potassium, lithium, calcium and magnesium.
In another embodiment, R
1C for the straight chain that contains two keys
15-C
23Thiazolinyl; R
2C for straight chain
1-C
6Alkyl; R
3C for straight chain
1-C
6Alkylidene group; M is hydrogen, ammonium ion or metallic cation, and described metallic cation is selected from sodium, potassium, lithium, calcium and magnesium.
In another embodiment, R
1C for the straight chain that contains two keys
15-C
20Thiazolinyl; R
2C for straight chain
1-C
4Alkyl; R
3C for straight chain
1-C
4Alkylidene group; M is hydrogen, ammonium ion or metallic cation, and described metallic cation is selected from sodium and potassium.
Amide group sulfonic acid shown in general formula I or its salt good water solubility have very strong surfactivity, can obviously change oil water interfacial tension.Take N-oleoyl-N methyl taurine sodium as example, use JZHY-180 type surface tension instrument, measure the surface tension of N-oleoyl-N methyl taurine sodium water solution by suspension ring method conventional in this area.In distilled water, the micelle-forming concentration of N-oleoyl-N methyl taurine sodium is about 0.16g/L; At NaCl approximately 15000mg/L, Ca
2+Approximately 800mg/L, Mg
2+Approximately in the simulated formation water of 200mg/L, the micelle-forming concentration of N-oleoyl-N methyl taurine sodium is about 0.024g/L; Under this concentration, surface tension is about 26.7mN/m.
The contriver is surprised to find that to have the amide group sulfonic acid shown in very strong surface-active general formula I or its salt when being used for crude oil production, wellbore lift and conveying, during especially for the exploitation of viscous crude, wellbore lift and conveying, can significantly reduce the viscosity of crude oil, particularly viscous crude.Therefore, available its preparation oil field additive particularly prepares the oil field viscosity-depression agent.
Amide group sulfonic acid shown in general formula I or its salt are when preparing the oil field with viscosity-depression agent and reducing viscosity of crude, it has following advantage: (1) is to crude oil, the wide accommodation of viscous crude particularly, it all has good viscosity reducing effect to common heavy oil, special viscous crude and super viscous crude, is specially adapted to viscosity and is approximately 1000-46 * 10
4The viscous crude of mPa.s; (2) good salt tolerance is applicable to NaCl approximately 20 * 10
4Mg/L, calcium+magnesium approximately 2 * 10
4The high salinity highrank fuel salinity water of mg/L; (3) to crude oil, viscous crude particularly, viscosity reduction efficient is high and consumption is low, concentration is that the aqueous solution of approximately 0.01%-1.0% just can be with crude oil, particularly the reduced viscosity of viscous crude is to approximately below 500mPa.s, preferably be reduced to approximately below 300mPa.s, more preferably be reduced to approximately below 150mPa.s, also more preferably be reduced to below 50mPa.s; (4) the Applicable temperature scope is wide, and the condition of＜150 ℃ is all applicable; (5) good water solubility, its aqueous stability is good, is not subjected to the impact of storage period, even its long-time placement does not affect it to the viscosity reducing effect of crude oil yet; (6) after the reduction viscosity of crude, formed crude oil emulsion stability is good.
Preparing the oil field with the amide group sulfonic acid shown in general formula I or its salt comprises with viscosity-depression agent or the process that reduces viscosity of crude the amide group sulfonic acid shown in general formula I or its salt are mixed the step that forms the aqueous solution with water.
Amide group sulfonic acid shown in general formula I or its salt in the preparation oil field with viscosity-depression agent or when reducing viscosity of crude, those skilled in the art can according to himself technical knowledge and the disclosure can according to usage determine the preparation oil field with viscosity-depression agent the concentration of the aqueous solution of the amide group sulfonic acid shown in general formula I or its salt and suitable crude oil and the ratio of this aqueous solution during with the reduction viscosity of crude.
For example, be about about 5.0% (w/w) of 0.01%-for the preparation of the oil field with viscosity-depression agent or the concentration that reduces the aqueous solution of the amide group sulfonic acid shown in the general formula I of viscosity of crude or its salt, preferred approximately 0.02%-approximately 3.0%, and more preferably from about 0.04%-approximately 2.0%, and most preferably from about 0.04%-approximately 1.5%.
For another example, the mass ratio of crude oil and this aqueous solution is less than or equal to approximately 90: 10, preferably less than or equal to approximately 75: 25, is more preferably less than and equals approximately 65: 35.But those skilled in the art are appreciated that also the concentration of aqueous solution that exceeds above-mentioned scope and the ratio of crude oil and the aqueous solution remain acceptable.
Not restriction of kind for the preparation of the water of the described aqueous solution can be tap water, also can be oilfield sewage, preferred oilfield sewage.
Amide group sulfonic acid shown in general formula I or its salt compound can synthesize through but not limited to following reaction scheme with suitable reaction raw materials.Those skilled in the art can be according to technical knowledge and the disclosure suitable temperature of reaction, reaction times and the reaction solvent that can according to usage determine following reaction scheme of himself.
1. hydroxy sulfonate is synthetic
(reaction conditions can be referring to Kunka, I.; Wirpsza, Z. " Preparation and reactions ofmonosulfomethylmelamine. " Tetrahedron (1984), 40 (10), 1855-6; Igawa, Manabu; Fukushi, Yasuko; Hayashita, Takashi; Hoffmann, Michael R. " Selective transport of aldehydes across an anion-exchange membrane via theformation of bisulfite adducts. " Industrial ﹠amp; Engineering Chemistry Research (1990), 29 (5), 857-61; The people such as Ceng Renquan " study on the synthesis of aminomethanesulfonic acid ", " Sichuan chemical industry ", the 8th the 2nd phase of volume in 2005)
(reaction conditions can be referring to Lauer, Walter M.; Hill, Archie., " Addition of sodiumbisulfite to alkylene oxides. " Journal of the American Chemical Society (1936), 581873-4)
(reaction conditions can be referring to Cao Zhanmei, " the synthetic and anticorrosion-antiscaling property research of ethane diamine double-2-hyolroxy propane sulfonic acid (EDHPS) ", " Treatment of Industrial Water ", (2006), 26 (1), 24-27; The people such as Chen Zhengguo " study on the synthesis of 3-chlorine-2-hydroxyl propanesulfonate ", " colloid and polymkeric substance ", the 21st the 2nd phase of volume in 2003)
2. alkyl amino sulfonate is synthetic
RNH
2+HOCH
2SO
3Na→RNHCH
2SO
3Na+H
2O
RNH
2+HOCH
2CH
2SO
3Na→RNHCH
2CH
2SO
3Na+H
2O
(reaction conditions can be referring to Hellmann, the people such as Heinrich " The mechanism of theaminomethylation reaction.II.The aminomethylating agent. " ChemischeBerichte (1956), 8981-95)
(reaction conditions is translated with Li Zhiming referring to Wang Quan is auspicious, " contemporary methodology of organic synthesis " (ModernMethods of Organic Synthesis (4th), original work: William Carruthers, Iain Coldham), press of East China University of Science, on March 1st, 2006 published, the 443rd page)
(reaction conditions can be referring to Young, Rodney C.; Ganellin, C.Robin; Graham, Michael J.; Mitchell, Robert C.; Roantree, Michael L.; " Zwitterionic analogsof cimetidine as H2 receptor antagonists ", Journal of Medicinal Chemistry (1987), 30 (7), 1150-6)
3. final compound is synthetic
(reaction conditions is translated with Li Zhiming referring to Wang Quan is auspicious, " contemporary methodology of organic synthesis " (ModernMethods of Organic Synthesis (4th), original work: William Carruthers, Iain Coldham), press of East China University of Science, on March 1st, 2006 published, the 443rd page)
The present invention also relates to composition on the other hand, and it comprises above the amide group sulfonic acid shown in defined general formula I or its salt and the chemical reagent that is selected from the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in triethylamine, Sulfite lignin or general formula I I:
General formula I
R
1-R
3With M all as hereinbefore defined;
General formula I I
R：H
3C-(CH
2)n- n＝7-17
a/b＝50％～100％。
In one embodiment, described composition comprises above the amide group sulfonic acid shown in defined general formula I or its salt and the chemical reagent that is selected from triethylamine.Based on the gross weight of said composition, the content of the amide group sulfonic acid shown in general formula I or its salt is about about 99% (w/w) of 70%-, and preferred approximately 77%-approximately 96%, and more preferably from about 82%-approximately 92%.
In one embodiment, described composition comprises above the amide group sulfonic acid shown in defined general formula I or its salt and the chemical reagent that is selected from Sulfite lignin, particularly sodium lignosulfonate and lignin sulfonic acid potassium.Based on the gross weight of said composition, the content of the amide group sulfonic acid shown in general formula I or its salt is about about 95% (w/w) of 5%-, and preferred approximately 35%-approximately 70%, and more preferably from about 40%-approximately 60%.
In one embodiment, described composition comprises above the amide group sulfonic acid shown in defined general formula I or its salt and the chemical reagent that is selected from the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in general formula I I.Based on the gross weight of said composition, the content of the amide group sulfonic acid shown in general formula I or its salt is about about 95% (w/w) of 5%-, and preferred approximately 30%-approximately 75%, and more preferably from about 40%-approximately 60%:
General formula I I
R:H
3C-(CH
2) n-n=7-17, preferred n=7-11,
A/b=50%～100%, preferred a/b=50%～95%.
One aspect of the present invention also relates to above-mentioned composition preparing the oil field with viscosity-depression agent and reducing viscosity of crude, particularly reduces the purposes in viscosity of thickened oil.The preparation oil field comprises with the process that reduces viscosity of crude with viscosity-depression agent mixes above-mentioned composition the step that forms the aqueous solution with water.
Similarly, those skilled in the art can according to usage be identified for preparing oil field viscosity-depression agent and the concentration of the aqueous solution of the present composition that reduces viscosity of crude and the mass ratio of crude oil and this aqueous solution according to technical knowledge and the disclosure of himself.
For example, be about about 5.0% (w/w) of 0.01%-for the preparation of the oil field with viscosity-depression agent and the concentration of aqueous solution that reduces the above-mentioned composition of viscosity of crude, preferred approximately 0.02%-approximately 3.0%, and more preferably from about 0.04%-approximately 2.0%, and most preferably from about 0.04%-approximately 1.5%.
For another example, the mass ratio of crude oil and this aqueous solution is as less than or equal to approximately 90: 10, preferably less than or equal to approximately 75: 25, be more preferably less than and equal approximately 65: 35, but it will be appreciated by those skilled in the art that the concentration of aqueous solution that exceeds above-mentioned scope and the ratio of crude oil and the described aqueous solution remain acceptable.
Not restriction of kind for the preparation of the water of the described aqueous solution can be tap water, also can be oilfield sewage, preferred oilfield sewage.
The present invention also relates to the reduction viscosity of crude on the other hand, particularly reduces the method for viscosity of thickened oil, and described method comprises the steps:
(1) the amide group sulfonic acid shown in general formula I defined above or its salt are mixed with water, form the aqueous solution;
(2) aqueous solution that obtains in step (1) is mixed to reduce viscosity of crude with crude oil.
In another embodiment, also comprise the step of adding the chemical reagent that is selected from the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in triethylamine or Sulfite lignin or general formula I I defined above in described step (1).
Those skilled in the art can understand the step of adding above-mentioned chemical reagent and can implement as follows: above-mentioned chemical reagent with after water mixes, then is mixed with the amide group sulfonic acid shown in general formula I or its salt; Perhaps the amide group sulfonic acid shown in general formula I or its salt and above-mentioned chemical reagent are mixed with water together; Perhaps with the amide group sulfonic acid shown in general formula I or its salt with after water mixes, then mix with above-mentioned chemical reagent.
When adding triethylamine, the mass ratio of the amide group sulfonic acid shown in general formula I or its salt and triethylamine is approximately 70: 30-approximately 99: 1, preferably approximately 77: 23-approximately 96: 4, more preferably from about 82: 18-approximately 92: 8.
When adding Sulfite lignin, when preferred sodium lignosulfonate and lignin sulfonic acid potassium, the mass ratio of the amide group sulfonic acid shown in general formula I or its salt and Sulfite lignin is approximately 5: 95-approximately 95: 5, preferably approximately 35: 65-approximately 70: 30, more preferably from about 40: 60-approximately 60: 40.
When the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in interpolation general formula I I defined above, the mass ratio of the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in the amide group sulfonic acid shown in general formula I or its salt and general formula I I is approximately 5: 95-approximately 95: 5, preferred approximately 30: 70-approximately 75: 25, more preferably from about 40: 60-approximately 60: 40.
In one embodiment, in the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in described general formula I I, n is preferably 7-11, and a/b is preferably 50%～95%.
In one embodiment, the total concn of the aqueous solution that obtains in step (1) is about about 5.0% (w/w) of 0.01%-, and preferred approximately 0.02%-approximately 3.0%, and more preferably from about 0.04%-approximately 2.0%, and most preferably from about 0.04%-approximately 1.5%.
In another embodiment, the aqueous solution that obtains in crude oil and step (1), is more preferably less than the mass ratio that equals approximately 65: 35 and mixes preferably less than or equal to approximately 75: 25 with less than or equal to approximately 90: 10.Embodiment
Can understand better the present invention by following specific embodiment, but given specific embodiment should not be construed as the present invention and only limits to following specific embodiment just for exemplary illustration the present invention.Except as otherwise noted, the per-cent that uses in following examples all is weight percentage.Crude oil sample used all after the KDM-2 type ultrasonic crude-oil dehydrating apparatus dehydration that Heze, Shandong electron temperature-control technical institute produces is degassed, is for experiment.Reagent used or obtain or prepare according to synthetic schemes disclosed herein by being purchased.
The impact of active constituent content on viscosity of crude in embodiment 1 viscosity-depression agent
1.1 in distilled water, the impact of active constituent content on viscosity of crude in viscosity-depression agent
Crude oil sample: the special viscous crude of old 375 wells, recording its viscosity under 60 ℃ with ordinary method is 13900mPas;
Viscosity-depression agent: effective constituent is mixed with the aqueous solution of different concns take N-oleoyl-N methyl taurine sodium as example in distilled water;
The mass ratio of crude oil and viscosity-depression agent: 7: 3;
Treatment temp: 60 ℃;
Then a certain amount of old 375 special viscous crude of wells of weighing are placed in Yongxing, Shandong instrument plant Water Tank with Temp.-controlled at 60 ℃ of lower constant temperature 6h in the 125ml wide-necked bottle.Be mixed with the N-oleoyl of different concns-N methyl taurine sodium water solution (being viscosity-depression agent) with distilled water; and after being placed in the thermostat(t)ed water constant temperature 0.5h of 60 ℃; pour in above-mentioned oil sample by the mass ratio of the crude oil of 7: 3 and viscosity-depression agent, stir with glass stick, form milk sap.Viscosity with BROOKFILD DV-III+ type rheometer measurement milk sap.Viscosity of crude and viscosity break ratio after processing are as shown in table 1:
In table 1 distilled water, the impact of N-oleoyl-N methyl taurine sodium water solution concentration on viscosity of crude
| N-oleoyl-N methyl taurine sodium water | Viscosity of crude/mPas (shearing rate 10sec after processing -1) | Viscosity break ratio/% (shearing rate 10sec -1) | Viscosity of crude/mPas (shearing rate 5sec after processing -1) | Viscosity break ratio/% (shearing rate 5sec -1) |
| Strength of solution (w/w) | ||||
| 0.4％ | 760 | 94.5 | 875 | 93.7 |
| 0.5％ | 210 | 98.5 | 250 | 98.2 |
| 0.7％ | 190 | 98.6 | 210 | 98.5 |
| 1.0％ | 80 | 99.4 | 75 | 99.5 |
By in above-mentioned table 1 as can be known, when N-oleoyl-N methyl taurine sodium water solution concentration increases, when namely in viscosity-depression agent, active constituent content increases, the milk sap reduced viscosity.
1.2 in oilfield sewage, the impact of active constituent content on viscosity of crude in viscosity-depression agent
Except use has the N-oleoyl of the oilfield sewage preparation different concns of following composition-N methyl taurine sodium water solution; adopt with above-described embodiment 1.1 in similar condition; evaluation in oilfield sewage, the impact of active constituent content on viscosity of crude in viscosity-depression agent.
Table 2 oilfield sewage Analysis Results of Water Quality
In table 3 oilfield sewage, the impact of N-oleoyl-N methyl taurine sodium water solution concentration on viscosity of crude
| N-oleoyl-N-N-methyltaurine sodium water solution concentration (w/w) | Viscosity of crude/mPas (shearing rate 10sec after processing -1) | Viscosity break ratio/% (shearing rate 10sec -1) | Viscosity of crude/mPas (shearing rate 5sec after processing -1) | Viscosity break ratio/% (shearing rate 5 sec -1) |
| 0.4％ | 58.7 | 99.6 | 75 | 99.5 |
| 0.5％ | 69 | 99.5 | 74 | 99.5 |
| 0.6％ | 39.5 | 99.7 | 55.2 | 99.6 |
| 0.8％ | 40.5 | 99.7 | 45.2 | 99.7 |
By in above-mentioned table 3 as can be known, when using the identical viscosity-depression agent of active constituent content, be better than the effect of distilled water emulsified crude oil with the effect of oilfield sewage emulsified crude oil.
1.3 in Saline Water, the impact of active constituent content on the viscosity of dissimilar crude oil in viscosity-depression agent
Use contains NaCl 15 * 10
3Mg/L, Ca
2+600mg/L and Mg
2+The N-oleoyl of the Saline Water preparation different concns of 200mg/L-N methyl taurine sodium water solution; adopt with above-described embodiment 1.1 in similar experiment condition; estimate in Saline Water the impact of active constituent content on the viscosity of dissimilar crude oil in viscosity-depression agent at different temperature.
Table 4 in high mineral water, the impact of N-oleoyl-N methyl taurine sodium water solution concentration on the viscosity of dissimilar crude oil
By in above-mentioned table 4 as can be known, in Saline Water, the viscosity-depression agent with different active constituent contents all has good viscosity reducing effect to the dissimilar crude oil with different viscosity.
The mass ratio of embodiment 2 crude oil and viscosity-depression agent is on reducing the impact of viscosity of crude
2.1 in different crude oil and the mass ratio of viscosity-depression agent and viscosity-depression agent, different active constituent contents are on reducing the impact of viscosity of crude
Crude oil sample: 21 10-13 well common heavy oils of Bohai Sea, recording its viscosity under 50C with ordinary method is 3769mPas;
Viscosity-depression agent: effective constituent is containing NaCl15000mg/L, Ca take N-oleoyl-N methyl taurine sodium as example
2++ Mg
2+Be mixed with the aqueous solution of different concns in Saline Water for 400mg/L;
The mass ratio of crude oil and viscosity-depression agent: as shown in table 5;
Treatment temp: 50 ℃;
Adopt the similar experiment condition described in embodiment 1.1, measuring different active constituent contents in the mass ratio of different crude oil and viscosity-depression agent and viscosity-depression agent under 50 ℃ affects the viscosity reduction of 21 10-13 well common heavy oils of Bohai Sea.
The impact of different active constituent contents on viscosity of crude in the mass ratio of the different crude oil of table 5 and viscosity-depression agent and viscosity-depression agent
By in above-mentioned table 5 as can be known, in the emulsification of crude oil process, under the condition that active constituent content is identical in viscosity-depression agent, the increase of viscosity-depression agent consumption is conducive to the reduction of crude oil emulsion viscosity.
2.2 in oilfield sewage, the impact on viscosity of crude of different crude oil and the mass ratio of viscosity-depression agent
Crude oil sample: the oblique 139 well common heavy oils of stake, recording its viscosity under 50 ℃ with ordinary method is 6028mPa.s;
Viscosity-depression agent: effective constituent is mixed with 0.4% the aqueous solution take N-oleoyl-N methyl taurine sodium as example in oilfield sewage;
The mass ratio of crude oil and viscosity-depression agent: as shown in table 6 below;
Treatment temp: 50 ℃;
Adopt the similar experiment condition described in embodiment 1.1, measuring quality at different crude oil and viscosity-depression agent under 50 ℃ than under condition, on the viscosity reduction impact of the oblique 139 well common heavy oils of stake.
The impact on viscosity of crude of the crude oil that table 6 is different and the mass ratio of viscosity-depression agent
| The mass ratio of crude oil and viscosity-depression agent | Viscosity of crude after processing (mPa.s) |
| 9∶1 | 6000 |
| 8∶2 | 500 |
| 7∶3 | 28 |
| 65∶35 | 14 |
| 5∶5 | 12 |
| 3∶7 | 12 |
| 2∶8 | 14 |
| 1∶9 | 10 |
By as seen from Table 6, the consumption of viscosity-depression agent increases, and viscosity of crude obviously reduces, and viscosity reducing effect is good, considers from production cost, and the mass ratio of crude oil and viscosity-depression agent is 65/35 o'clock the best.
The stability of embodiment 3 viscosity-depression agents
Crude oil sample: the special viscous crude of old 375 wells, recording its viscosity under 60 ℃ with ordinary method is 13900mPas;
Viscosity-depression agent: effective constituent is mixed with 0.7% the aqueous solution take N-oleoyl-N methyl taurine sodium as example in containing the water of NaCl15000mg/L;
The mass ratio of crude oil and viscosity-depression agent: 7: 3;
Treatment temp: 60 ℃;
After viscosity-depression agent (being N-oleoyl-N methyl taurine sodium water solution) is placed different time as shown in table 7; adopt the similar experiment condition described in embodiment 1.1, the impact of the viscosity-depression agent after measuring the placement different time under 60 ℃ on the special viscosity of thickened oil of old 375 wells.
The impact of the viscosity-depression agent of table 7 different storage periods on viscosity of crude
| The storage period of viscosity-depression agent | Viscosity of crude after processing (mPas) |
| 5h | 61 |
| 1d | 60 |
| 5d | 64 |
| 10d | 60 |
| 1 month | 66 |
| 2 months | 67 |
| 6 months | 71 |
| 1 year | 68 |
| 2 years | 69 |
By can find out in above-mentioned table 7, the prolongation along with storage period of viscosity-depression agent even place 2 years, does not affect the effect that viscosity-depression agent reduces viscosity of crude.This shows, viscosity-depression agent is stable.
The stability of crude oil emulsion after embodiment 4 emulsifications
Crude oil sample: the special viscous crude of old 375 wells, recording its viscosity under 60 ℃ with ordinary method is 13900mPas;
Viscosity-depression agent: effective constituent is mixed with 0.7% the aqueous solution take N-oleoyl-N methyl taurine sodium as example in containing the water of NaCl15000mg/L;
The mass ratio of crude oil and viscosity-depression agent: 7: 3;
Treatment temp: 60 ℃;
Adopt the similar experiment condition described in embodiment 1.1, measure viscosity-depression agent to the impact of the special viscosity of thickened oil of old 375 wells under 60 ℃, find that viscous crude by viscosity-depression agent emulsification, is form of emulsion, this moment, viscosity was 61mPas.After under 60 ℃ standing 14 hours, find viscous oil emulsion by the breakdown of emulsion layering subsequently, the upper strata is oil phase, and lower floor is water, and upper oil phase viscosity is 5362mPas.Then the viscous oil emulsion after standing is stirred again, once more be form of emulsion, viscosity is 64mPas.
The impact of embodiment 5 present compositions on viscosity of crude
5.1 general formula I+triethylamine
Crude oil sample: the special viscous crude of old 375 wells, recording its viscosity under 60 ℃ with ordinary method is 13900mPas;
Viscosity-depression agent 1: contain (1) N-oleoyl-N methyl taurine sodium, containing NaCl15000mg/L, Mg
2+200mg/L and Ca
2+Be mixed with respectively 0.5% and 0.7% the aqueous solution in the water of 600mg/L; And (2) triethylamine, its concentration in above-mentioned Saline Water is as shown in table 7
The mass ratio of crude oil and viscosity-depression agent: 7: 3;
Treatment temp: 60 ℃;
Adopt the similar experiment condition described in embodiment 1.1, measure viscosity-depression agent 1 to the impact of viscosity of crude under 60 ℃.
The impact of table 8 viscosity-depression agent 1 on viscosity of crude
By in table 8 as can be known, N-oleoyl-when N methyl taurine sodium consumption is high, triethylamine is little on the viscosity of crude impact; When N-oleoyl-N methyl taurine sodium consumption hanged down, triethylamine was large on the viscosity of crude impact.
5.2 general formula I+Sulfite lignin
Crude oil sample: the special viscous crude of old 375 wells, recording its viscosity under 60 ℃ with ordinary method is 13900mPas;
Viscosity-depression agent 2: contain (1) N-oleoyl-N methyl taurine sodium, it is containing NaCl15000mg/L, Mg
2+200mg/L and Ca
2+Be mixed with 0.4% the aqueous solution in the water of 600mg/L; And (2) Sulfite lignin are take sodium lignosulfonate as example, and the mass ratio of itself and N-oleoyl-N methyl taurine sodium is as shown in table 9
The mass ratio of crude oil and viscosity-depression agent: 7: 3;
Treatment temp: 60 ℃;
Adopt the similar experiment condition described in embodiment 1.1, measure viscosity-depression agent 2 to the impact of viscosity of crude under 60 ℃.
The impact of table 9 viscosity-depression agent 2 on viscosity of crude
| N-oleoyl-N methyl taurine sodium: sodium lignosulfonate (w/w) | Viscosity break ratio (%) |
| 10∶0 | 94 |
| 9∶1 | 94 |
| 8∶2 | 95 |
| 7∶3 | 97 |
| 6∶4 | 99 |
| 5∶5 | 99 |
| 4∶6 | 99 |
| 3∶7 | 96 |
| 2∶8 | 95 |
| 1∶9 | 94 |
By in table 9 as can be known, contain N-and have good viscosity reducing effect by the viscosity-depression agent of acyl group-N methyl taurine sodium and sodium lignosulfonate.When both mass ratio is 6: 4-4: in the time of 6, viscosity reducing effect is best.5.3 general formula I+general formula I I
Crude oil sample: the special viscous crude of old 375 wells, recording its viscosity under 60 ℃ with ordinary method is 13900mPas;
Viscosity-depression agent 3: contain (1) compound of Formula I take N-oleoyl-N methyl taurine sodium as example, it is containing NaCl 15000mg/L, Mg
2+200mg/L and Ca
2+Be mixed with 0.4% the aqueous solution in the water of 600mg/L; And the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in (2) general formula I I, wherein a/b=1: 1, R=CH
3-(CH
2)
8-, the mass ratio of itself and N-oleoyl-N methyl taurine sodium is as shown in table 10;
The mass ratio of crude oil and viscosity-depression agent: 7: 3;
Treatment temp: 60 ℃;
Adopt the similar experiment condition described in embodiment 1.1, measure viscosity-depression agent 3 to the impact of viscosity of crude under 60 ℃.
The impact of table 10 viscosity-depression agent 3 on viscosity of crude
| General formula I: general formula I I (w/w) | Viscosity break ratio (%) |
| 10∶0 | 94 |
| 9∶1 | 95 |
| 8∶2 | 96 |
| 7∶3 | 98 |
| 6∶4 | 99 |
| 5∶5 | 99 |
| 4∶6 | 99 |
| 3∶7 | 97 |
| 2∶8 | 96 |
| 1∶9 | 95 |
By in table 10 as can be known, the viscosity-depression agent that contains the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in N-oleoyl-N methyl taurine sodium and general formula I I has good viscosity reducing effect.When both ratio is 6: 4-4: in the time of 6, viscosity reducing effect is best.
Claims (33)
1. composition, the chemical reagent that it comprises the amide group sulfonic acid shown in general formula I or its salt and is selected from the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in triethylamine, Sulfite lignin or general formula I I,
General formula I
R
1For containing straight chain or C side chain of at least one two key
12-C
25Thiazolinyl;
R
2C for straight or branched
1-C
8Alkyl;
R
3C for straight or branched
1-C
8Alkylidene group;
M is selected from hydrogen, ammonium ion and metallic cation, and described metallic cation is selected from sodium, potassium, lithium, calcium, magnesium, aluminium, iron, zinc, copper and manganese;
General formula I I
R：H
3C-(CH
2)n- n＝7-17
a/b＝50％～100％；
When described chemical reagent was selected from triethylamine, based on the gross weight of described composition, the content of the amide group sulfonic acid shown in described general formula I or its salt was 70w/w%-99w/w%;
When described chemical reagent was selected from Sulfite lignin, based on the gross weight of described composition, the content of the amide group sulfonic acid shown in described general formula I or its salt was 5w/w%-95w/w%; And
When described chemical reagent was selected from polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in general formula I I, based on the gross weight of described composition, the content of the amide group sulfonic acid shown in described general formula I or its salt was 5w/w%-95w/w%.
2. composition as claimed in claim 1, wherein R
1C for the straight or branched that contains two keys
12-C
25Base, described metallic cation is selected from sodium, potassium, lithium, calcium and magnesium.
3. composition as claimed in claim 1, R
1C for the straight or branched that contains two keys
15-C
23Thiazolinyl, R
2C for straight or branched
1-C
6Alkyl, R
3C for straight or branched
1-C
6Alkylidene group, described metallic cation is selected from sodium and potassium.
4. composition as claimed in claim 3, R
1C for the straight or branched that contains two keys
15-C
20Thiazolinyl, R
2C for straight or branched
1-C
4Alkyl, R
3C for straight or branched
1-C
4Alkylidene group, described metallic cation is selected from sodium and potassium.
5. composition as claimed in claim 1, when described chemical reagent was selected from triethylamine, based on the gross weight of described composition, the content of the amide group sulfonic acid shown in general formula I or its salt was 77w/w%-96w/w%.
6. composition as claimed in claim 5, the content of the amide group sulfonic acid shown in general formula I or its salt is 82w/w%-92w/w%.
7. composition as claimed in claim 1, when described chemical reagent was selected from Sulfite lignin, based on the gross weight of described composition, the content of the amide group sulfonic acid shown in general formula I or its salt was 35w/w%-70w/w%.
8. composition as claimed in claim 7, the content of the amide group sulfonic acid shown in general formula I or its salt is 40w/w%-60w/w%.
9. as the described composition of arbitrary claim in claim 1-4, described Sulfite lignin are sodium lignosulfonate and lignin sulfonic acid potassium.
10. composition as claimed in claim 7, described Sulfite lignin are sodium lignosulfonate and lignin sulfonic acid potassium.
11. composition as claimed in claim 8, described Sulfite lignin are sodium lignosulfonate and lignin sulfonic acid potassium.
12. composition as claimed in claim 1, when described chemical reagent is selected from polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in general formula I I, based on the gross weight of described composition, the content of the amide group sulfonic acid shown in general formula I or its salt is 30w/w%-75w/w%.
13. composition as claimed in claim 12, the content of the amide group sulfonic acid shown in general formula I or its salt is 40w/w%-60w/w%.
14. as the described composition of arbitrary claim in claim 1-4, in the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in general formula I I, n=7-11, a/b=50%～95%.
15. composition as claimed in claim 12, in the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in general formula I I, n=7-11, a/b=50%～95%.
16. composition as claimed in claim 13, in the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in general formula I I, n=7-11, a/b=50%～95%.
17. the purposes of the described composition of arbitrary claim in reducing viscosity of crude in claim 1-16.
18. reduce the method for viscosity of crude, described method comprises the steps:
(1) the amide group sulfonic acid shown in the defined general formula I of arbitrary claim or its salt in claim 1-4 are mixed with water, and then add the chemical reagent that is selected from the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in triethylamine, Sulfite lignin or general formula I I, form the aqueous solution:
General formula I I
R：H
3C-(CH
2)n- n＝7-17，
a/b＝50％～100％；
Perhaps,
The defined composition of arbitrary claim in claim 1-4 is mixed with water, form the aqueous solution; And
(2) aqueous solution that obtains in step (1) is mixed to reduce viscosity of crude with crude oil.
19. the method for reduction viscosity of crude as claimed in claim 18, when adding triethylamine, the mass ratio of the amide group sulfonic acid shown in general formula I or its salt and triethylamine is 70: 30-99: 1.
20. the method for reduction viscosity of crude as claimed in claim 18, when adding Sulfite lignin, the mass ratio of the amide group sulfonic acid shown in general formula I or its salt and Sulfite lignin is 5: 95-95: 5.
21. the method for reduction viscosity of crude as claimed in claim 20, described Sulfite lignin are sodium lignosulfonate and lignin sulfonic acid potassium.
22. the method for reduction viscosity of crude as claimed in claim 18, when the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in interpolation general formula I I, the mass ratio of the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in the amide group sulfonic acid shown in general formula I or its salt and general formula I I is 5: 95-95: 5.
23. the method for reduction viscosity of crude as claimed in claim 22, in the polyoxyethylene polyoxypropylene alkylbenzene phenolic ether shown in general formula I I, n is 7-11, and a/b is 50%～95%.
24. as the method for the described reduction viscosity of crude of arbitrary claim in claim 18-23, the total concn of the described aqueous solution that obtains in described step (1) is 0.01w/w%-5.0w/w%.
25. the total concn of the described aqueous solution that obtains in the method for reduction viscosity of crude as claimed in claim 24, described step (1) is 0.02w/w%-3.0w/w%.
26. the total concn of the described aqueous solution that obtains in the method for reduction viscosity of crude as claimed in claim 25, described step (1) is 0.04w/w%-2.0w/w%.
27. the total concn of the described aqueous solution that obtains in the method for reduction viscosity of crude as claimed in claim 26, described step (1) is 0.04w/%-1.5w/w%.
28. as the method for the described reduction viscosity of crude of arbitrary claim in claim 18-23, described crude oil mixes with the mass ratio less than or equal to 90: 10 with the middle described aqueous solution that obtains of described step (1).
29. the method for reduction viscosity of crude as claimed in claim 24, described crude oil mixes with the mass ratio less than or equal to 90: 10 with the middle described aqueous solution that obtains of described step (1).
30. the method for reduction viscosity of crude as claimed in claim 28, described crude oil mixes with the mass ratio less than or equal to 75: 25 with the middle described aqueous solution that obtains of described step (1).
31. the method for reduction viscosity of crude as claimed in claim 29, described crude oil mixes with the mass ratio less than or equal to 75: 25 with the middle described aqueous solution that obtains of described step (1).
32. the method for reduction viscosity of crude as claimed in claim 30, described crude oil mixes with the mass ratio less than or equal to 65: 35 with the middle described aqueous solution that obtains of described step (1).
33. the method for reduction viscosity of crude as claimed in claim 31, described crude oil mixes with the mass ratio less than or equal to 65: 35 with the middle described aqueous solution that obtains of described step (1).
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| CN102604618B (en) * | 2012-02-07 | 2013-09-04 | 中国石油天然气股份有限公司 | Viscosity reducer for crude oil in cold production stratum of thick oil |
| CN103573231B (en) * | 2012-07-23 | 2017-09-08 | 中国石油化工股份有限公司 | The method for improving recovery ratio of sensitive heavy oil reservoir |
| CN102936491B (en) * | 2012-11-20 | 2015-05-06 | 孙安顺 | Weak-base surface active mixed preparation and preparation method of surface active agent thereof |
| CN104559993A (en) * | 2013-10-28 | 2015-04-29 | 中国石油化工股份有限公司 | Tertiary poly-surfactant composition and application thereof |
| CN106032466B (en) * | 2015-03-20 | 2018-08-28 | 中国石油化工股份有限公司 | A kind of emulsifying and viscosity-reducing agent for condensed oil |
| CN107236530B (en) * | 2017-07-10 | 2019-01-04 | 山东大学 | A kind of water-base viscosity-reducing agent of emulsified superthick oil and preparation method thereof |
| CN107840965B (en) * | 2017-11-24 | 2020-11-17 | 中国海洋石油集团有限公司 | Preparation method of amphiphilic polymer with long-chain branch structure |
| CN111378514A (en) * | 2020-02-24 | 2020-07-07 | 中国石油大学(华东) | Fuel additive, preparation method, composition and application thereof, and alcohol hydrocarbon composite fuel |
| CN115725277B (en) * | 2021-08-30 | 2023-12-08 | 中国石油天然气集团有限公司 | Viscosity reducer for oil-based drilling fluid and preparation method thereof |
| CN114350340B (en) * | 2022-01-13 | 2023-01-17 | 陕西科技大学 | Permeation enhancer for fracturing and preparation method and application thereof |
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| CN1251589C (en) * | 1998-12-25 | 2006-04-19 | 三共阿格罗株式会社 | Agricultural chemical composition for water surface |
| CN101250397A (en) * | 2008-04-03 | 2008-08-27 | 中国地质大学（武汉） | Method for preparing amphoteric ion polymer fluid loss additive |
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| CN1152129C (en) * | 2002-08-26 | 2004-06-02 | 宋光泉 | Vegetable and fruit detoxicating agent and its prepn |
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