CN114686188B - Nucleoside phospholipid drilling fluid lubricant and preparation method thereof - Google Patents
Nucleoside phospholipid drilling fluid lubricant and preparation method thereof Download PDFInfo
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Abstract
The invention relates to the field of petroleum drilling fluid, in particular to a nucleoside phospholipid drilling fluid lubricant and a preparation method thereof. The drilling fluid lubricant is prepared from the following raw materials in percentage by mass: solvent water ։ nucleoside sodium monophosphate ։ epoxy compound ։ fatty chain primary amine ։ sulfite=15-20 ։ 15 ։, 6-12 ։, 7-10 ։, 3-4. The nucleoside phospholipid drilling fluid lubricant adopts abundant source and biodegradable nucleoside sodium monophosphate as raw materials. Meanwhile, the difficult problem that the nucleoside sodium monophosphate with low fat solubility is difficult to introduce a hydrophobic long fatty chain is overcome. The method comprises the steps of carrying out ring opening reaction, continuous amino substitution and sulfonic acid group modification on an epoxy bond through a phosphate group in nucleoside sodium monophosphate, and introducing a long fatty chain and a sulfonic acid group into the structure of the nucleoside monophosphate in the form of double phospholipids to construct the lubricant. The synthesis method is simple and efficient, low in biotoxicity, good in environmental protection effect, strong in water dispersion capability, excellent in lubricating effect and high-temperature resistant, and has application potential of drilling fluid lubrication.
Description
Technical Field
The invention relates to the field of petroleum drilling fluid, in particular to a nucleoside phospholipid drilling fluid lubricant and a preparation method thereof.
Background
Along with the gradual development of petroleum exploration and development to offshore and deep stratum, shale oil and gas exploration and development is accelerated, the number of horizontal wells is continuously increased, the length of the horizontal section is continuously prolonged, the contact area between a drilling tool and a well wall is continuously increased, the problems of high friction torque, pressure bearing, drilling sticking and the like have great influence on drilling efficiency and drilling cost, and the requirement of drilling fluid on novel efficient drilling fluid is continuously increased. However, at present, a great deal of drilling fluid lubricants are developed by adopting an oil mixing process, and the agents such as an emulsifying agent, an antiwear agent, an extreme pressure agent and the like are compounded with crude oil, diesel oil, white oil and gas to form the drilling fluid lubricants, so that the water dispersion capacity of the lubricants is low, and after a plurality of drilling fluids circulate, base oil is easily separated out from the drilling fluid, thereby reducing the lasting effect of the lubricants. Notably, the use of mineral oil can cause significant environmental pollution, which in turn can place significant stress on subsequent cuttings handling. At present, novel high-efficiency drilling fluid lubricants developed in a synthetic form show excellent advantages in lubricating performance and environmental protection capability, and particularly, drilling fluid lubricants formed by compounding and modifying based on natural product vegetable oil, lecithin and sugar as basic raw materials show excellent advantages in raw material sources, environmental protection performance and lubricating effect.
Chinese patent CN 101157850A discloses a high temperature resistant lubricant for drilling fluid prepared from animal and vegetable oil, which is prepared from waste animal and vegetable oil, ethanolamine, diethylene glycol, sulfur, oil-soluble resin and graphite powder, and has the advantages of no fluorescence, good compatibility with drilling fluid and little environmental pollution. Chinese patent CN 101760186A discloses a compound vegetable oil lubricant for drilling fluid and its preparation method. The lubricant is prepared by compounding vegetable oil scraps, sodium dodecyl sulfate, span 80, sodium carboxymethyl cellulose, polyvinylpyrrolidone, graphite and serpentine serving as raw materials. The lubricant has the functions of inhibiting hydration expansion of shale, strengthening well wall and preventing sticking.
Chinese patent CN 110791365A discloses a method for modifying water-based lubricating fluid with wood flour-soybean lecithin. The lubricant adopts hydrogen peroxide and lactic acid hydroxylation modified lecithin as main components, and is prepared by mixing amino silane composite modified wood powder, rust inhibitor triethanolamine, sodium dodecyl sulfate, ferrous carbonate, polyhydroxy modified graphene and surface modified carbon fiber, and mixing and strongly stirring the mixture. Chinese patent CN 111560238A discloses an environment-friendly drilling fluid lubricant and a preparation method thereof. The method adopts cationic alkyl glycoside and quaternized nano silicon dioxide as raw materials to construct the drilling fluid lubricant. The lubricant has the advantages of excellent lubricating performance and good inhibition performance.
It can be seen that the use of natural products as raw materials for constructing lubricants has become a trend in research and development of drilling fluid lubricants nowadays. Nucleoside monophosphates are important constituent substances of living organisms and are precursors of biological macromolecules such as ribonucleic acids (RNA) and deoxyribonucleic acids (DNA). The nucleoside monophosphate structure contains an extreme pressure lubricating group phosphate group, a nitrogen-containing heterocyclic compound with metal surface complexing adsorption capacity and a polar group hydroxyl, so that the nucleoside monophosphate can be adsorbed on the metal surface in the friction process to form a lubricating protective film. Especially, according to the market demand of the umami element, the inosine monophosphate and the guanosine monophosphate are prepared by adopting a microbial fermentation process, so that the two nucleoside monophosphates can be obtained in a large quantity, and the cost is greatly reduced. However, there are still some bottleneck problems that need to be solved in the formation of drilling fluid lubricants from nucleoside monophosphates. Although nucleoside monophosphates contain a plurality of lubricating adsorption groups in the structure, a firm lubricating film can be formed on the surface of friction metal, a single nucleoside monophosphate adsorption film cannot provide an effective lubricating effect, and an outer hydrophobic lubricating film is required to effectively produce the lubricating effect, so that a hydrophobic long-chain group needs to be modified on the nucleoside monophosphate structure. However, nucleoside monophosphates have excellent water solubility, very low lipid solubility, and it is difficult to introduce hydrophobic long chain groups in organic solvents by esterification, amidation and alkylation. Therefore, how to perform fat-soluble modification on nucleoside monophosphates through chemical modification to improve the lubricating effect of the nucleoside monophosphates is a key problem in the application of the nucleoside monophosphates to drilling fluid lubricants.
Disclosure of Invention
Aims at the problems existing in the process of constructing the drilling fluid lubricant by using the nucleoside monophosphate. The invention aims to provide a nucleoside phospholipid drilling fluid lubricant and a preparation method thereof.
The technical scheme is as follows:
a nucleoside phospholipid drilling fluid lubricant, which has the structural formula:
wherein R is one or more of oleic acid acyl, palmitic acid acyl and stearic acid acyl;
r' is one or two of hydrogen and amino;
a is
One of them.
Further, the drilling fluid lubricant is prepared from the following raw materials in percentage by mass: solvent water, sodium nucleoside monophosphate, epoxy compound, primary aliphatic chain amine, sulfite=15-20:15:6-12:7-10:3-4.
Further, the nucleoside sodium monophosphate is one or two of inosine sodium monophosphate and guanosine sodium monophosphate.
Further, the epoxy compound is one of epichlorohydrin, ethylene glycol diglycidyl ether and diethylene glycol diglycidyl ether.
Further, the fatty chain primary amine is one of hexadecylamine, octadecylamine, mono-oleoyl ethylenediamine, mono-stearoyl ethylenediamine and mono-soft acyl ethylenediamine.
Further, the sulfite is one of sodium sulfite, sodium bisulfite, potassium sulfite and potassium hydrogen sulfite.
Further, the preparation method of the nucleoside phospholipid drilling fluid lubricant comprises the following steps:
(1) Mixing nucleoside sodium monophosphate with water, heating and stirring to dissolve the nucleoside sodium monophosphate and form a nucleoside sodium monophosphate aqueous solution;
(2) Adding an epoxy compound into the reaction liquid, heating and stirring for reaction;
(3) Adding the fatty chain primary amine into the reaction liquid in the step (2), and heating and stirring for reaction;
(4) And (3) adding sulfite into the reaction solution in the step (3), heating and stirring for reaction, and distilling solvent water under reduced pressure to obtain the final ribonucleoside phospholipid drilling fluid lubricant.
Further, the heating temperature in the step (1) is 50-80 ℃.
Further, the reaction temperature in the step (2) is 100-130 ℃ and the reaction time is 4-8h.
Further, the reaction temperature in the step (3) is 80-120 ℃ and the reaction time is 2-5h.
Further, the reaction temperature in the step (4) is 80-100 ℃ and the reaction time is 2-4h.
The beneficial effects of the invention are as follows:
the preparation method of the nucleoside phospholipid drilling fluid lubricant provided by the invention is that epoxide and phosphoric acid groups are subjected to epoxy ring-opening reaction in aqueous solution to form phosphoric acid diester, and active modifiable groups such as epoxy groups or alkyl chlorides are introduced, so that the difficult problem that nucleoside monophosphate with low fat solubility is difficult to modify by organic synthesis reaction is solved. The epoxy bond and the alkyl chloride in the nucleoside phospholipid structure of the reaction product are favorable for the subsequent modification of the hydrophobic long fatty chain group and the introduction of the water-soluble group. In the aspect of introducing a fat-soluble group, the invention selects a series of hydrophobic fatty chain compounds containing single primary amine, and utilizes the primary amine with stronger activity in the structure to react with alkyl chloride and epoxy groups to modify the hydrophobic long alkyl chain to the nucleoside monophosphate structure, thereby providing a hydrophobic lubricating film in the lubricating process of the lubricant. In addition, with the introduction of a long hydrophobic fatty chain and the esterification of a phosphate group as a hydrophilic group, the water solubility of nucleoside monophosphates is greatly reduced. The sulfite is used to react with residual alkyl chloride or epoxy groups to form sulfonate groups, thereby enhancing the water solubility of the lubricant.
The invention adopts natural product nucleoside monophosphate as lubricant raw material, and the raw material nucleoside monophosphate is widely distributed in natural organisms. Especially, the flavor nucleoside monophosphate taking guanosine monophosphate and inosine monophosphate as main components is a new generation flavor enhancer after sodium glutamate, and can be obtained in a large amount in a form of microbial fermentation, so that the nucleoside monophosphate has a very rich raw material source and is particularly suitable for developing drilling fluid lubricants. The phosphatide, ribose and base in the lubricant structure formed by the nucleoside monophosphate can be absorbed by microorganisms and naturally degraded, and even if the main structure of the modified nucleoside monophosphate is not destroyed, the formed nucleoside monophosphate has stronger environmental protection performance. The phospholipid, hydroxyl and polyazaheterocyclic compound in the nucleoside monophosphate structure has strong extreme pressure lubricating capability and metal surface adsorption capability, and can effectively promote the lubricant to be adsorbed on the metal surface to form a lubricating film, thereby improving the lubricating effect. The nucleoside monophosphate is modified by adopting firm and stable groups such as phospholipid, alkylamine and the like in the modification process, and simultaneously, the sulfonic acid groups modified around the phospholipid can greatly strengthen the hydrolysis resistance of the lubricant, so that the lubricant has stronger high-temperature stability.
Drawings
FIG. 1 is a modified synthetic route of the present invention.
Detailed Description
The present invention will be described in further detail with reference to examples.
A nucleoside phospholipid drilling fluid lubricant and a preparation method thereof. The preparation method comprises the following steps:
(1) Mixing nucleoside sodium monophosphate with water, heating and stirring to dissolve the nucleoside sodium monophosphate to form a nucleoside sodium monophosphate aqueous solution;
(2) Adding an epoxy compound into the reaction liquid, heating and stirring for reaction;
(3) Adding the fatty chain primary amine into the reaction liquid in the step (2), and heating and stirring for reaction;
(4) And (3) adding sulfite into the reaction solution in the step (3), heating and stirring for reaction, and distilling solvent water under reduced pressure to obtain the final ribonucleoside phospholipid drilling fluid lubricant. The synthetic route for the modification of this lubricant is shown in figure 1.
The mass ratio of the raw materials is as follows: solvent water, sodium nucleoside monophosphate, epoxide, primary fatty chain amine, sulfite=15-20:15:6-12:7-10:3-4.
The nucleoside sodium monophosphate in the step (1) is one or two of inosine sodium monophosphate and guanosine sodium monophosphate.
The heating temperature of the step (1) is 50-80 ℃.
The epoxy compound in the step (2) is one of epichlorohydrin, ethylene glycol diglycidyl ether and diethylene glycol diglycidyl ether.
The reaction temperature of the step (2) is 100-130 ℃ and the reaction time is 4-8h.
The fatty chain primary amine in the step (3) is one of hexadecylamine, octadecylamine, mono-oleoyl ethylenediamine, mono-stearoyl ethylenediamine and mono-soft ethylenediamine.
The reaction temperature of the step (3) is 80-120 ℃ and the reaction time is 2-5h.
The sulfite in the step (4) is one of sodium sulfite, sodium bisulfite, potassium sulfite and potassium hydrogen sulfite.
The reaction temperature of the step (4) is 80-100 ℃ and the reaction time is 2-4h.
Example 1
15g of taste nucleoside sodium monophosphate (the mass ratio of the inosine sodium monophosphate to the guanosine sodium monophosphate is 50wt%:50 wt%) is mixed with 20mL of water to form turbid liquid, heated and stirred at 50 ℃ until the nucleoside sodium monophosphate is completely dissolved to form transparent clear solution, 6g of epichlorohydrin is added, mixed and stirred to form emulsion, reacted at 100 ℃ for 8 hours to obtain yellow transparent solution, 10g of mono-oleoyl ethylenediamine is added, heated and stirred at 120 ℃ for 2 hours, sodium sulfite is added for 3.5g, heated and stirred at 80 ℃ for 4 hours, and solvent water is distilled out under reduced pressure to obtain the final ribonucleoside phospholipid drilling fluid lubricant.
Example 2
15g of taste nucleoside sodium monophosphate (the mass ratio of the inosine sodium monophosphate to the guanosine sodium monophosphate is 50wt%:50 wt%) is mixed with 15mL of water to form turbid liquid, heated and stirred at 80 ℃ until the nucleoside sodium monophosphate is completely dissolved to form transparent clear solution, 6g of epoxy chloropropane is added, mixed and stirred to form emulsion, reacted at 100 ℃ for 8 hours to obtain yellow transparent solution, 7g of hexadecylamine is added, heated and stirred at 80 ℃ for 5 hours, 3g of sodium bisulphite is added, heated and stirred at 100 ℃ for 3 hours, and solvent water is distilled out under reduced pressure to obtain the final ribonucleoside phospholipid drilling fluid lubricant.
Example 3
15g of taste nucleoside sodium monophosphate (the mass ratio of the inosine sodium monophosphate to the guanosine sodium monophosphate is 50wt%:50 wt%) is mixed with 15mL of water to form turbid liquid, heated and stirred at 80 ℃ until the nucleoside sodium monophosphate is completely dissolved to form transparent clear solution, 6g of epichlorohydrin is added, mixed and stirred to form emulsion, reacted at 100 ℃ for 8 hours to obtain yellow transparent solution, 8g of octadecylamine is added, heated and stirred at 80 ℃ for 5 hours, 4g of potassium sulfite is added, heated and stirred at 90 ℃ for 2 hours, and solvent water is distilled out under reduced pressure to obtain the final ribonucleoside phospholipid drilling fluid lubricant.
Example 4
15g of taste nucleoside sodium monophosphate (the mass ratio of the inosine sodium monophosphate to the guanosine sodium monophosphate is 50wt%:50 wt%) is mixed with 20mL of water to form turbid liquid, heated and stirred at 50 ℃ until the nucleoside sodium monophosphate is completely dissolved to form transparent clear solution, 6g of epichlorohydrin is added, mixed and stirred to form emulsion, reacted at 100 ℃ for 8 hours to obtain yellow transparent solution, 10g of monostearoyl ethylenediamine is added, heated and stirred at 120 ℃ for 3 hours, added with 3.5g of potassium hydrogen sulfite, heated and stirred at 80 ℃ for 4 hours, and solvent water is distilled out under reduced pressure to obtain the final ribonucleoside phospholipid drilling fluid lubricant.
Example 5
15g of taste nucleoside sodium monophosphate (the mass ratio of the inosine sodium monophosphate to the guanosine sodium monophosphate is 50wt%:50 wt%) is mixed with 20mL of water to form turbid liquid, heated and stirred at 50 ℃ until the nucleoside sodium monophosphate is completely dissolved to form transparent clear solution, 6g of epichlorohydrin is added, mixed and stirred to form emulsion, reacted at 100 ℃ for 8 hours to obtain yellow transparent solution, 10g of monopalmitin ethylenediamine is added, heated and stirred at 120 ℃ for 3 hours, sodium sulfite is added, heated and stirred at 80 ℃ for 4 hours, and solvent water is distilled out under reduced pressure to obtain the final ribonucleoside phospholipid drilling fluid lubricant.
Example 6
15g of taste nucleoside sodium monophosphate (the mass ratio of the inosine sodium monophosphate to the guanosine sodium monophosphate is 50wt%:50 wt%) is mixed with 20mL of water to form turbid liquid, heated and stirred at 50 ℃ until the nucleoside sodium monophosphate is completely dissolved to form transparent clear solution, 10g of ethylene glycol diglycidyl ether is added, mixed and stirred to form emulsion, reacted at 130 ℃ for 4 hours to obtain orange-yellow transparent solution, 10g of monooleoyl ethylenediamine is added, heated and stirred at 120 ℃ for 2 hours, sodium bisulphite is added, heated and stirred at 80 ℃ for 4 hours, and solvent water is distilled out under reduced pressure to obtain the final ribonucleoside phospholipid drilling fluid lubricant.
Example 7
15g of taste nucleoside sodium monophosphate (the mass ratio of the inosine sodium monophosphate to the guanosine sodium monophosphate is 50wt%:50 wt%) is mixed with 20mL of water to form turbid liquid, the turbid liquid is heated and stirred at 50 ℃ until the nucleoside sodium monophosphate is completely dissolved to form transparent clear solution, 12g of diethylene glycol diglycidyl ether is added, the mixture is mixed and stirred to form emulsion, the reaction is carried out at 130 ℃ for 6 hours to obtain orange-yellow transparent solution, 10g of monooleoyl ethylenediamine is added, the heating and stirring reaction is carried out at 120 ℃ for 2 hours, 3g of sodium sulfite is added, the heating and stirring reaction is carried out at 80 ℃ for 4 hours, and solvent water is distilled out under reduced pressure to obtain the final ribonucleoside phospholipid drilling fluid lubricant.
Example 8
Mixing 15g of inosine monophosphate with 20mL of water to form turbid liquid, heating and stirring at 50 ℃ until the inosine monophosphate is completely dissolved to form transparent clear solution, adding 6g of epichlorohydrin, mixing and stirring to form emulsion, reacting at 100 ℃ for 8 hours to obtain yellow transparent solution, adding 10g of monooleoyl ethylenediamine, heating and stirring at 120 ℃ for 2 hours, adding 3.5g of sodium sulfite, heating and stirring at 80 ℃ for 4 hours, and distilling solvent water under reduced pressure to obtain the final ribonucleoside phospholipid drilling fluid lubricant.
Example 9
15g of guanosine monophosphate and 20mL of water are mixed to form turbid liquid, heating and stirring are carried out at 50 ℃ until the guanosine monophosphate is completely dissolved to form transparent clear solution, 6g of epichlorohydrin is added, mixing and stirring are carried out to form emulsion, reaction is carried out at 100 ℃ for 8 hours to obtain yellow transparent solution, 10g of monooleoyl ethylenediamine is added, heating and stirring are carried out at 120 ℃ for 2 hours, sodium sulfite is added, heating and stirring are carried out at 80 ℃ for 4 hours, and solvent water is distilled out under reduced pressure, thus obtaining the final ribonucleoside phospholipid drilling fluid lubricant.
Comparative example 1
15g of taste nucleoside sodium monophosphate (the mass ratio of inosine sodium monophosphate to guanosine sodium monophosphate is 50wt%:50 wt%) is mixed with 20mL of water to form turbid liquid, the turbid liquid is heated and stirred at 50 ℃ until the nucleoside sodium monophosphate is completely dissolved to form transparent clear solution, 6g of epichlorohydrin is added, the mixture is mixed and stirred to form emulsion, the yellow clear solution is obtained after reaction for 8 hours at 100 ℃, and solvent water is distilled out under reduced pressure to obtain the nucleoside phospholipid without fatty chain modification.
Comparative example 2
15g of taste nucleoside sodium monophosphate (the mass ratio of inosine sodium monophosphate to guanosine sodium monophosphate is 50wt%:50 wt%) is mixed with 20mL of water to form turbid liquid, heated and stirred at 50 ℃ until the nucleoside sodium monophosphate is completely dissolved to form transparent clear solution, 6g of epichlorohydrin is added, mixed and stirred to form emulsion, reacted at 100 ℃ for 8 hours to obtain yellow transparent solution, 10g of mono-oleoyl ethylenediamine is added, heated and stirred at 120 ℃ to react for 2 hours, and the solvent water is distilled out under reduced pressure to obtain the nucleoside phospholipid without sulfonic group modification on the single fatty chain.
Comparative example 3
15g of taste nucleoside sodium monophosphate (the mass ratio of inosine sodium monophosphate to guanosine sodium monophosphate is 50wt%:50 wt%) is mixed with 20mL of water to form turbid liquid, heated and stirred at 50 ℃ until the nucleoside sodium monophosphate is completely dissolved to form transparent clear solution, 6g of epichlorohydrin is added, mixed and stirred to form emulsion, reacted at 100 ℃ for 8 hours to obtain yellow transparent solution, 20g of mono-oleoyl ethylenediamine is added, heated and stirred at 120 ℃ to react for 5 hours, and the solvent water is distilled out under reduced pressure to obtain the double-fatty-chain non-sulfonic-group modified nucleoside phospholipid.
Blank example 1
Taste nucleoside sodium monophosphate (the mass ratio of inosine sodium monophosphate to guanosine sodium monophosphate is 50wt%:50 wt%)
The evaluation method comprises the following steps:
the extreme pressure lubrication coefficient test method in the invention comprises the following steps:
(1) The base slurry is prepared according to the proportion of distilled water, bentonite, anhydrous sodium carbonate=400 mL, 20g and 0.7g, the base slurry is stirred for 20 min at the speed of 11000r/min by a high-speed stirrer, the wall of the container and the adhesion on the stirrer are scraped every 5min during the stirring, and the sealing maintenance is carried out for 24h at room temperature to obtain the base slurry.
(2) Extreme pressure lubrication coefficient test: to the above base stock, 2g (0.5% of the amount of lubricant added) of lubricant was added, and the mixture was stirred with a high-speed stirrer at 11000r/min for 5min, and the extreme pressure lubrication coefficient of the mixed base stock was tested, and the lubrication coefficient reduction rate was calculated according to the following formula, and the base stock lubrication coefficient was 0.738.
The calculation formula is as follows:
wherein:
r- -the reduction rate of the lubrication coefficient,%;
K 0 -the lubrication coefficient of the base stock;
K 1 -coefficient of lubrication of the base stock after addition to the sample.
TABLE 1 comparison of the lubricating effects of nucleoside phospholipids modified with different substituents
In accordance with the present invention, table 1 compares the lubrication effect of nucleoside phospholipids modified with various substituents to determine the effect of the substituents on the nucleoside phospholipid lubricant. From blank examples, the raw material taste nucleoside sodium monophosphate has a certain lubricating effect, and the reduction rate of the lubricating coefficient can reach 51.1%, which shows that phospholipid, hydroxyl and polyazacyclo in the taste nucleotide structure can be effectively adsorbed on the surface of a metal sliding block to form a layer of protective film, thereby providing the lubricating effect. However, the lubricating effect of the unmodified nucleoside sodium monophosphate does not meet the lubricating requirement of drilling fluid, which indicates that the strength of a single-layer adsorption film provided by the nucleoside sodium monophosphate is still limited, and an outer-layer hydrophobic lubricating film is required to provide an effective lubricating effect. Similarly, the first comparative example is two nucleoside phospholipids modified by short fatty chains, and the lubricating effect is not obviously improved, which indicates that the short fatty chains are difficult to form an outer hydrophobic lubricating film. The third and fourth comparative examples are the single long fatty chain and the two long fatty chain modified nucleoside phospholipids, respectively, and it can be seen that the lubrication effect of the single long fatty chain modified nucleoside phospholipids is improved to a certain extent, but the water dispersion capability of the nucleoside phospholipids is reduced due to the hydrophobic effect of the long fatty chains, so that the lubrication effect of the lubricant is not effectively exhibited. In particular, the double long fatty chain modified nucleoside phospholipids are waxy solids and have no water dispersibility at all, and therefore, have no lubricating effect at all. The comparison results show that modifying both long fatty chains and strong hydrophilic group sulfonic acid groups on the structure of nucleoside phospholipids can provide lubricants with excellent water-dispersing ability while maintaining the lubricating properties of nucleoside phospholipids.
TABLE 2 comparison of the lubricating effect of nucleoside phospholipids of different structures
Table 2 compares the lubricating effects of nucleoside phospholipid lubricants of different structures, and it can be seen that nucleoside phospholipid lubricants modified with long fatty chains and sulfonic acid groups all exhibit excellent lubricating effects. The structure and lubrication effect of the nucleoside phospholipid lubricants of the first, second and third examples are compared, and it can be seen that the lubrication effect is enhanced with the increase of the chain length of the fat. The lubricant formed by different ether bond connecting groups in the sixth embodiment and the seventh embodiment can be seen that the lubrication effect is gradually enhanced along with the increase of ether bonds, and the lubricant is easier to effectively disperse in the drilling fluid after the hydrophilicity is enhanced, so that the utilization rate of the lubricant is improved, and the lubrication effect is enhanced. Examples eight and nine are respectively the lubricant formed by inosine sodium monophosphate and guanosine sodium monophosphate, and as guanosine sodium monophosphate has one more amino group than inosine sodium monophosphate, the electron supply capacity of the whole polyazacyclo is increased, thereby enhancing the adsorption capacity of the lubricant on the metal surface and enhancing the lubricating effect.
TABLE 3 comparison of lubricating effects of the lubricants of example one after various aging conditions
Table 3 shows that the lubrication effect of the lubricant of the first embodiment is compared under different aging conditions, and it can be seen that the lubrication coefficient reduction rate of the lubricant is increased to a certain extent along with the increase of the aging temperature, but the lubrication coefficient reduction rate can still be maintained to be more than 75%, which means that the developed lubricant has a relatively stable structure, can effectively exert the lubrication effect under the high temperature condition, and has relatively strong high temperature resistance.
TABLE 4 comparison of biotoxicity of aqueous lubricant solutions (0.5 wt%) in different examples
Table 4 shows the various embodimentsIs compared with the lubricant biotoxicity. As can be seen from the table, EC's of the nucleoside phospholipid lubricants developed 50 The values are all over 20000mg/L required by the petroleum and natural gas industry standard and are higher than 100000mg/L. Therefore, the lubricant adopting nucleoside phospholipids as a main structure has stronger biocompatibility and lower negative influence on the environment.
Therefore, the nucleoside phospholipid drilling fluid lubricant developed by the subject adopts nucleoside sodium monophosphate as a raw material, and is constructed by a method of ring opening reaction of phosphoric acid on an epoxy bond, amino substitution and sulfonic acid group modification. The lubricant raw material nucleoside sodium monophosphate has the advantages of rich and environment-friendly sources, simple and efficient synthesis method, low biotoxicity, good environment-friendly effect, strong water dispersion capability, excellent lubricating effect and high temperature resistance, and has the application potential of drilling fluid lubrication.
The foregoing description is only illustrative of the preferred embodiments of the present invention and is not intended to limit the scope of the invention. It is intended that all such equivalent variations and modifications as fall within the scope of the claims are covered by the appended claims.
Claims (11)
1. The nucleoside phospholipid drilling fluid lubricant is characterized by having a structural formula as follows:
r' is one or two of hydrogen and amino;
2. A method of preparing the nucleoside phospholipid drilling fluid lubricant of claim 1, comprising the steps of: (1) Mixing nucleoside sodium monophosphate with water, heating and stirring to dissolve the nucleoside sodium monophosphate to form a nucleoside sodium monophosphate aqueous solution; (2) Adding an epoxy compound into the reaction liquid, heating and stirring for reaction; (3) Adding the fatty chain primary amine into the reaction liquid in the step (2), and heating and stirring for reaction; (4) And (3) adding sulfite into the reaction solution in the step (3), heating and stirring for reaction, and distilling solvent water under reduced pressure to obtain the final ribonucleoside phospholipid drilling fluid lubricant.
3. The preparation method of the nucleoside phospholipid drilling fluid lubricant according to claim 2, which is characterized by comprising the following raw materials in percentage by mass: solvent water ։ nucleoside sodium monophosphate ։ epoxy compound ։ fatty chain primary amine ։ sulfite=15-20 ։ 15 ։, 6-12 ։, 7-10 ։, 3-4.
4. The method for preparing the nucleoside phospholipid drilling fluid lubricant according to claim 2, wherein the nucleoside sodium monophosphate is one or two of inosine sodium monophosphate and guanosine sodium monophosphate.
5. The method for preparing a nucleoside phospholipid drilling fluid lubricant according to claim 2, wherein the epoxy compound is one of epichlorohydrin, ethylene glycol diglycidyl ether and diethylene glycol diglycidyl ether.
6. The method for preparing the nucleoside phospholipid drilling fluid lubricant according to claim 2, wherein the fatty chain primary amine is one of mono-oleoylethylene diamine, mono-stearylethylene diamine and mono-soft ethylenediamine.
7. The method for preparing the nucleoside phospholipid drilling fluid lubricant according to claim 2, wherein the sulfite is one of sodium sulfite, sodium bisulfite, potassium sulfite and potassium bisulfite.
8. The method for preparing the nucleoside phospholipid drilling fluid lubricant according to any one of claims 2 to 7, wherein the heating temperature in the step (1) is 50 to 80 ℃.
9. The preparation method according to any one of claims 2 to 7, wherein the reaction temperature in the step (2) is 100 to 130 ℃ and the reaction time is 4 to 8 hours.
10. The preparation method according to any one of claims 2 to 7, wherein the reaction temperature in the step (3) is 80 to 120 ℃ and the reaction time is 2 to 5 hours.
11. The preparation method according to any one of claims 2 to 7, wherein the reaction temperature in the step (4) is 80 to 100 ℃ and the reaction time is 2 to 4 hours.
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002363278A (en) * | 2001-03-02 | 2002-12-18 | Nof Corp | Polyalkylene oxide-modified phospholipid and method for producing the same |
| CN1566130A (en) * | 2003-07-03 | 2005-01-19 | 中国人民解放军军事医学科学院放射医学研究所 | Nucleoside analogue lipid derivative and salt thereof |
| CN101089010A (en) * | 1998-02-25 | 2007-12-19 | 埃莫里大学 | 2'-fluoroncucleosides |
| CN103232510A (en) * | 2012-11-23 | 2013-08-07 | 北京大学 | 5'-amino-2',5'-dideoxynucleotide phospholipid molecules, and preparation method and application thereof |
| CN108472121A (en) * | 2015-11-20 | 2018-08-31 | 加利福尼亚太平洋生物科学股份有限公司 | The reagent of shielded dye marker |
| CN110564378A (en) * | 2019-09-20 | 2019-12-13 | 中海油田服务股份有限公司 | Environment-friendly lubricant for drilling fluid and preparation method and application thereof |
| CN111704897A (en) * | 2020-04-30 | 2020-09-25 | 中石化石油工程技术服务有限公司 | Temperature-resistant and salt-resistant lubricating drag reducer for drilling fluid and preparation method thereof |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9702957D0 (en) * | 1997-08-15 | 1997-08-15 | Medivir Ab | antivirals |
| JP3844654B2 (en) * | 1997-08-15 | 2006-11-15 | メディヴィル・アクチボラグ | Nucleoside analogs such as retroviral reverse transcriptase and antiviral agents including inhibitors of hepatitis B virus (HBV) DNA polymerase |
| EP1680477B1 (en) * | 2003-09-10 | 2010-07-14 | M-I L.L.C. | Phospholipid lubricating agents in aqueous based drilling fluids |
| CA2685748A1 (en) * | 2007-05-14 | 2008-11-14 | Rfs Pharma, Llc. | Azido purine nucleosides for treatment of viral infections |
| WO2010075554A1 (en) * | 2008-12-23 | 2010-07-01 | Pharmasset, Inc. | Synthesis of purine nucleosides |
| CN102659843B (en) * | 2012-04-24 | 2015-06-24 | 北京大学 | D, L-guanosine nucleoside analog monophosphate, and preparation method and application thereof |
| CN109370547A (en) * | 2018-11-15 | 2019-02-22 | 长江大学 | A kind of wear-resistant lubricant for drilling fluid and its preparation method and application |
| US11365365B2 (en) * | 2019-07-29 | 2022-06-21 | Saudi Arabian Oil Company | Lubricants that include alkyl esters and fatty acids |
| CN112279877B (en) * | 2020-12-15 | 2021-08-06 | 南京颐媛生物医学研究院有限公司 | Nucleoside phosphate and synthesis method thereof |
| CN113583069B (en) * | 2021-09-09 | 2023-06-06 | 北京大学 | Nucleoside phospholipid compounds, chemical synthesis method thereof and application thereof in nucleic acid delivery |
-
2020
- 2020-12-31 CN CN202011630704.9A patent/CN114686188B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101089010A (en) * | 1998-02-25 | 2007-12-19 | 埃莫里大学 | 2'-fluoroncucleosides |
| JP2002363278A (en) * | 2001-03-02 | 2002-12-18 | Nof Corp | Polyalkylene oxide-modified phospholipid and method for producing the same |
| CN1566130A (en) * | 2003-07-03 | 2005-01-19 | 中国人民解放军军事医学科学院放射医学研究所 | Nucleoside analogue lipid derivative and salt thereof |
| CN103232510A (en) * | 2012-11-23 | 2013-08-07 | 北京大学 | 5'-amino-2',5'-dideoxynucleotide phospholipid molecules, and preparation method and application thereof |
| CN108472121A (en) * | 2015-11-20 | 2018-08-31 | 加利福尼亚太平洋生物科学股份有限公司 | The reagent of shielded dye marker |
| CN110564378A (en) * | 2019-09-20 | 2019-12-13 | 中海油田服务股份有限公司 | Environment-friendly lubricant for drilling fluid and preparation method and application thereof |
| CN111704897A (en) * | 2020-04-30 | 2020-09-25 | 中石化石油工程技术服务有限公司 | Temperature-resistant and salt-resistant lubricating drag reducer for drilling fluid and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| 司西强，王中华，魏军，甄剑武，邱正松.阳离子烷基糖苷的绿色合成及性能评价.应用化工.2012,第41卷(第9期),第1526-1530页. * |
| 李公让，王承俊.极性吸附钻井液润滑剂的研究进展与发展趋势.钻井液与完井液.2020,第37卷(第5期),第542-549页. * |
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