CN105693640A - Quaternary ammonium salt type surfactant containing symmetric heterocycle and synthesis method of surfactant - Google Patents
Quaternary ammonium salt type surfactant containing symmetric heterocycle and synthesis method of surfactant Download PDFInfo
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- CN105693640A CN105693640A CN201610211856.2A CN201610211856A CN105693640A CN 105693640 A CN105693640 A CN 105693640A CN 201610211856 A CN201610211856 A CN 201610211856A CN 105693640 A CN105693640 A CN 105693640A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/602—Compositions for stimulating production by acting on the underground formation containing surfactants
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/62—Compositions for forming crevices or fractures
- C09K8/72—Eroding chemicals, e.g. acids
- C09K8/74—Eroding chemicals, e.g. acids combined with additives added for specific purposes
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- C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
- C09K2208/30—Viscoelastic surfactants [VES]
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
- C09K2208/32—Anticorrosion additives
Abstract
The invention relates to a quaternary ammonium salt type surfactant containing symmetric heterocycle in the technical field of petroleum production engineering, and a synthesis method of the surfactant. According to the quaternary ammonium salt type surfactant containing symmetric heterocycle, long-chain fatty acid is used to react with 3,5-diamino-1,2,4-triazole to generate a yellow solid which is a fatty acid amido intermediate A containing heterocycle; and then the fatty acid amido intermediate A containing heterocycle is used to react with 1,3-dichloro isopropanol to generate the quaternary ammonium salt type surfactant containing symmetric heterocycle. The surfactant molecular structure contains triazole symmetric heterocycle and has corrosion inhibition; the surfactant molecular structure further contains quaternary ammonium salt dication and four hydrophobic chains to thicken acid liquor; and therefore, one surfactant has two functions at the same time, and the aim of reducing the cost of acid liquor for oil field acidification is finally achieved.
Description
Technical field
The present invention relates to technical field of oil production engineering, particularly to a kind of quaternary ammonium salt cationic surfactant containing symmetrical heterocycle and synthetic method thereof。
Background technology
Since the nineties in last century, abroad successfully viscoelastic surfactant is used for fracturing fluid (being called for short VES fracturing fluid), foreign petroleum company uses VES fracturing fluid system in the frac-packing operations of U.S. Mexico gulf, after in numerous oil fields extensive uses such as Canada, the U.S., Italy, the Gulf of Mexico, the conventional fracturing fluid of its effect of increasing production ratio is effective, and rapidly be popularization, open VES of the fracturing fluid widely studied。Mainly have studied cation, anion, amphoteric ion type surface activity both at home and abroad, these VES fracturing fluid systems have without residue, to the feature such as fracturing fracture, formation damage be little。
The domestic VES fracturing fluid from introduction road Weir company in 1999 exploitation first since Gas field application, just starts VES fracturing fluid application upsurge。Viscoelastic surfactant for self-diverting acid has VES-1, VDA-08, SDVA, SAP-BET, BNS, VDA-SL, VDA etc., the exploitation of the high temperature resistant clean fracturing liquid system of low cost is received to the extensive concern of people。2003, the high temperature resistant clean fracturing fluid SCF that Jiang Bo et al. develops, can heatproof 150 DEG C。The VES-II quaternary ammonium salt cationic surfactant that Cui's meeting in 2005 is outstanding, develop。Jia Zhen good fortune et al. describes the clean fracturing fluid of several Surfactant Used in Viscoelastic Fracturing Fluids and different additive composition afterwards, including cationic quaternary ammonium salt surfactant, betaine type cationic surfactant, nonionic surfactant, anion and nonionic and the clean fracturing fluid such as both sexes complexed surfactant, hydrophobic associated polymer surfactant, wherein, anion and nonionic and amphoteric surfactant composite fracturing fluid can heatproofs 150 DEG C。2007, Yu Donghe et al., Cui Huijie et al. report clean fracturing fluid application in the reservoir fracturing improvement of Tongxi region respectively, clean fracturing fluid application in paulownia 12, paulownia 47 fault block integral hydraulic fracturing, the anti-swollen property etc. of guanidine gum fracturing fluid residue after breaking gel and clean fracturing fluid has been studied by Yu Donghe et al., and Cui Huijie et al. have studied the viscosity-temperature characteristic of different surfaces surfactant concentration。Although various novel surface activity thickening agents propose in succession, but there are some common problems in them, and as temperature tolerance is poor, it is common between 60-90 DEG C, consumption is big and cost is high, and serviceability is single。
At present, research disclosed in prior art is concentrated mainly on and describes solution rheological behavior, the form of micelle and the elastic mechanism produced, research, also also in the starting stage, develops critical micelle concentration high temperature resistant, low, multi-functional viscoelastic surfactant is this technological development direction。
Summary of the invention
It is an object of the invention to provide and a kind of can realize making acidification of oil field acid solution inhibition, a kind of quaternary ammonium salt cationic surfactant containing symmetrical heterocycle of multiviscosisty function and synthetic method thereof simultaneously。
A kind of quaternary ammonium salt cationic surfactant containing symmetrical heterocycle of the present invention, its structural formula is:
Wherein,For oleamide base or stearic amide base or erucyl amide base。
Containing triazole symmetry heterocycle in the surfactant molecule structure of the present invention, there is corrosion inhibition；Also containing quaternary ammonium salt dication, 4 hydrophobic chains in surfactant molecule structure, it is possible to make acid solution multiviscosisty, it is achieved that a kind of surface activity is provided simultaneously with two kinds of functions, is finally reached the purpose reducing acidification of oil field acid solution cost。
The synthetic method of the above-mentioned quaternary ammonium salt cationic surfactant containing symmetrical heterocycle of the present invention, with long-chain fatty acid and 3,5-diaminostilbenes, it is containing heterocycloaliphatic acid amide groups intermediate A that 2,4-triazole reactions generate yellow solid；With reacting the quaternary ammonium salt cationic surfactant generated containing symmetrical heterocycle containing heterocycloaliphatic acid amide groups intermediate A and 1,3-dichloroisopropanol。
Preferred long-chain fatty acid is oleic acid or stearic acid or erucic acid。
The synthetic method containing symmetrical heterocycloaliphatic acid amide groups intermediate A of the present invention is:
By long-chain fatty acid, 3,5-diaminostilbenes, 2; 4-triazole and ethylene glycol solvent; under argon shield, after heating 80 DEG C of thawings, add potassium hydroxide; wherein; long-chain fatty acid: 3,5-diaminostilbenes, 2; 4-triazole: the mol ratio of potassium hydroxide is 2.1:1:0.05, ethylene glycol is the 50% of above-mentioned reactant gross mass。Being continuously heating to 150 DEG C, after reaction 12h, wash with 1% sodium carbonate hydrothermal solution, to remove unreacted long-chain fatty acid and solvent ethylene glycol, obtain yellow solid for containing heterocycloaliphatic acid amide groups intermediate A after drying, said process is by having reacted as follows:
Said process is by having reacted as follows:
Wherein,For oleamide base or erucyl amide base or stearic amide base。
Being separately added into intermediate A, 1,3-dichloroisopropanol, sodium carbonate, alcohol solvent in another flask, wherein, intermediate A: 1,3-dichloroisopropanol: the mol ratio of sodium carbonate is 2:1:0.05, ethanol is the 50% of above-mentioned reactant gross mass。After temperature rising reflux reaction 24h, decompression is distilled off solvent, namely obtains a kind of quaternary ammonium salt cationic surfactant containing symmetrical heterocycle of the present invention after drying；Said process is by having reacted as follows:
Accompanying drawing explanation
Fig. 1 is the viscosity test results figure of the oleamide base the adopting embodiment 1 quaternary ammonium salt cationic surfactant preparation viscous acid acid solution containing symmetrical heterocycle。
Wherein, 1
Detailed description of the invention
Embodiment 1
126mmol oleic acid, 60mmol3,5-diaminostilbene is added in three-neck flask, 2; 4-triazole and 20.9g ethylene glycol solvent; under argon shield, after heating 80 DEG C of thawings, add 3mmol potassium hydroxide; wherein; oleic acid: 3,5-diaminostilbenes, 2; 4-triazole: the mol ratio of potassium hydroxide is 2.1:1:0.05, ethylene glycol is the 50% of above-mentioned reactant gross mass。It is continuously heating to 150 DEG C, after reaction 12h, washs with 1% sodium carbonate hydrothermal solution, to remove unreacted oleic acid and solvent ethylene glycol, obtain yellow solid after drying for containing heterocycloaliphatic acid amide groups intermediate A。
40mmol intermediate A, 20mmol1,3-dichloroisopropanol, 1mmol sodium carbonate, 13.9g alcohol solvent it is separately added in another flask, wherein, intermediate A: 1,3-dichloroisopropanol: the mol ratio of sodium carbonate is 2:1:0.05, ethanol is the 50% of above-mentioned reactant gross mass。After temperature rising reflux reaction 24h, decompression is distilled off solvent, namely obtains the oleamide base quaternary ammonium salt cationic surfactant containing symmetrical heterocycle of the present invention after drying；Said process is by having reacted as follows:
The nuclear magnetic data of the quaternary ammonium salt cationic surfactant containing symmetrical heterocycle of the present embodiment synthesis:1HNMR (400MHz, DMSO-d) δ 9.15 (s, 4H), 5.42-5.36 (m, 8H), 5.01-4.96 (s, 2H), 4.87-4.84 (d, J=4.0HZ, 4H), 3.58 (s, 1H), 3.45-3.39 (m, 6H), 3.21 (s, 3H), 3.17-3.13 (m, 2H), 2.89-2.85 (m, 2H), 2.34 (m, 8H), 2.20-2.16 (m, 16H), 1.61-1.57 (m, 8H), 1.53 (m, 2H), 1.32-1.26 (m, 66H), 0.89-0.85 (m, 12H)；13CNMR (100MHz, DMSO-d) δ 174.5,173.8,145.2,130.7,68.9,59.5,37.4,31.6,29.3,29.1,29 .0,28.9,28.7,28.3,25.1,22.9,14.0.；Mass spectrometric data is: MSESI (m/z): [M]2+calcdforC79H144Cl2N10O5, 1383.1；Found, 1383.2。
The above-mentioned oleamide base quaternary ammonium salt cationic surfactant containing symmetrical heterocycle is configured to viscous acid acid solution by following mass ratio: 2% quaternary ammonium salt cationic surfactant containing symmetrical heterocycle, the concentrated hydrochloric acid (referring to that HCl content in viscous acid acid solution is 20%) of 20%, all the other are water。
Take the viscous acid acid solution of a certain amount of said method preparation with reference to industry standard SY/T5107-2005 " aqueous fracturing fluid method of evaluating performance ", carry out viscosity test, use Haake torque rheometer, at shear rate 170s-1, 100 degree of condition down cuts of temperature 1 hour, test result, as it is shown in figure 1, acid liquid viscosity 73mPa.s, test result indicate that: has stronger acids liquid thickening capabilities containing symmetrical heterocycle viscoelastic surfactant。
The viscous acid acid solution separately taking the preparation of a certain amount of said method carries out corrosion inhibiting ability test, static inhibition speed 0.9881 (g/ (m under 100 degree of conditions of temperature2.h), dynamic inhibition speed 1.8118/ (g/ (m2.h), test result meets industry standard SY/T540511996 " acidifying corrosion inhibiter performance test method and evaluation index "。
Embodiment 2
126mmol stearic acid, 60mmol3,5-diaminostilbene is added in three-neck flask, 2; 4-triazole and 21g ethylene glycol solvent; under argon shield, after heating 80 DEG C of thawings, add 3mmol potassium hydroxide; wherein; stearic acid: 3,5-diaminostilbenes, 2; 4-triazole: the mol ratio of potassium hydroxide is 2.1:1:0.05, ethylene glycol is the 50% of above-mentioned reactant gross mass。It is continuously heating to 150 DEG C, after reaction 12h, washs with 1% sodium carbonate hydrothermal solution, to remove unreacted stearic acid and solvent ethylene glycol, obtain yellow solid after drying for containing heterocycle stearic amide base intermediate A。
40mmol intermediate A, 20mmol1,3-dichloroisopropanol, 1mmol sodium carbonate, 14g alcohol solvent it is separately added in another flask, wherein, intermediate A: 1,3-dichloroisopropanol: the mol ratio of sodium carbonate is 2:1:0.05, ethanol is the 50% of above-mentioned reactant gross mass。After temperature rising reflux reaction 24h, decompression is distilled off solvent, namely obtains the stearic amide base quaternary ammonium salt cationic surfactant containing symmetrical heterocycle of the present invention after drying；Said process is by having reacted as follows:
The stearic amide base of the present embodiment is containing the nuclear magnetic data of the quaternary ammonium salt cationic surfactant of symmetrical heterocycle:1HNMR (400MHz, DMSO-d) δ 9.16 (s, 4H), 4.99-4.96 (s, 2H), 4.87-4.84 (d, J=4.0HZ, 4H), 3.58 (s, 1H), 3.45-3.39 (m, 6H), 3.21 (s, 3H), 3.17-3.13 (m, 6H), 2.89-2.85 (m, 2H), 2.34 (m, 8H), 2.20-2.16 (m, 16H), 1.61-1.57 (m, 8H), 1.53 (m, 2H), 1.32-1.26 (m, 78H), 0.89-0.85 (m, 12H)；13CNMR (100MHz, DMSO-d) δ 174.2,173.0,156.1,147.1,58.1,38.3,31.9,29.6,29.3,28.9,28 .6,25.6,22.7,14.1；Mass spectrometric data is: MSESI (m/z): [M]2+calcdforC79H152Cl2N10O5, 1391.1；Found, 1391.3。
Claims (5)
1., containing a quaternary ammonium salt cationic surfactant for symmetrical heterocycle, its structural formula is:
Wherein,For oleamide base or stearic amide base or erucyl amide base。
2. the synthetic method of surfactant described in a claim 1, it is characterised in that with long-chain fatty acid and 3,5-diaminostilbenes, it is containing heterocycloaliphatic acid amide groups intermediate A that 2,4-triazole reactions generate yellow solid；Again with the described quaternary ammonium salt cationic surfactant reacting containing heterocycloaliphatic acid amide groups intermediate A and 1,3-dichloroisopropanol and generating containing symmetrical heterocycle。
3. the synthetic method of surfactant according to claim 2, it is characterised in that described long-chain fatty acid is oleic acid or stearic acid or erucic acid。
4. the synthetic method of surfactant according to claim 2, it is characterised in that the described synthetic method containing symmetrical heterocycloaliphatic acid amide groups intermediate A is: by long-chain fatty acid, 3; 5-diaminostilbene, 2,4-triazoles and ethylene glycol solvent; under argon shield, heat after melting to 80 DEG C, add potassium hydroxide; wherein; long-chain fatty acid: 3,5-diaminostilbenes, 2; 4-triazole: the mol ratio of potassium hydroxide is 2.1:1:0.05, ethylene glycol is the 50% of above-mentioned reactant gross mass。It is continuously heating to 150 DEG C, after reaction 12h, wash several times with 1% sodium carbonate hydrothermal solution, to remove unreacted long-chain fatty acid and solvent ethylene glycol, obtaining yellow solid after drying for containing heterocycloaliphatic acid amide groups intermediate A, said process is by having reacted as follows:
Said process is by having reacted as follows:
Wherein,For oleamide base or stearic amide base or erucyl amide base。
5. the synthetic method of surfactant according to claim 2, it is characterized in that, by described containing symmetrical heterocycloaliphatic acid amide groups intermediate A, 1,3-dichloroisopropanol, sodium carbonate, alcohol solvent mix, wherein, intermediate A: 1,3-dichloroisopropanol: the mol ratio of sodium carbonate is 2:1:0.05, ethanol is the 50% of above-mentioned reactant gross mass；After temperature rising reflux reaction 24h, decompression is distilled off solvent, namely obtains a kind of quaternary ammonium salt cationic surfactant containing symmetrical heterocycle of the present invention after drying；Said process is by having reacted as follows:
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106947455A (en) * | 2017-03-21 | 2017-07-14 | 四川格鑫拓科技有限公司 | New how sub- viscoelastic surfactant and its preparation method and application |
| CN114805115A (en) * | 2022-04-26 | 2022-07-29 | 四川零碳智慧科技有限公司 | Temperature-resistant type dihydroxyl cationic viscoelastic surfactant, preparation method thereof, fracturing fluid and application thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106947455A (en) * | 2017-03-21 | 2017-07-14 | 四川格鑫拓科技有限公司 | New how sub- viscoelastic surfactant and its preparation method and application |
| CN106947455B (en) * | 2017-03-21 | 2019-11-05 | 四川格鑫拓科技有限公司 | Novel how sub- viscoelastic surfactant and its preparation method and application |
| CN114805115A (en) * | 2022-04-26 | 2022-07-29 | 四川零碳智慧科技有限公司 | Temperature-resistant type dihydroxyl cationic viscoelastic surfactant, preparation method thereof, fracturing fluid and application thereof |
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