CN114410314A - Preparation of amphoteric surfactant - Google Patents
Preparation of amphoteric surfactant Download PDFInfo
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- CN114410314A CN114410314A CN202011069301.1A CN202011069301A CN114410314A CN 114410314 A CN114410314 A CN 114410314A CN 202011069301 A CN202011069301 A CN 202011069301A CN 114410314 A CN114410314 A CN 114410314A
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- amphoteric surfactant
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- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 239000002280 amphoteric surfactant Substances 0.000 title claims abstract description 14
- 239000004094 surface-active agent Substances 0.000 claims abstract description 23
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 claims abstract description 16
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims abstract description 12
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 claims abstract description 12
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 7
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 claims abstract description 7
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims abstract description 7
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims abstract description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000005966 aza-Michael addition reaction Methods 0.000 claims abstract description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 4
- UHUFTBALEZWWIH-UHFFFAOYSA-N tetradecanal Chemical compound CCCCCCCCCCCCCC=O UHUFTBALEZWWIH-UHFFFAOYSA-N 0.000 claims abstract 6
- 238000006467 substitution reaction Methods 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 230000035484 reaction time Effects 0.000 claims description 8
- 239000012467 final product Substances 0.000 claims description 6
- 230000000694 effects Effects 0.000 abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000011084 recovery Methods 0.000 description 6
- 238000006073 displacement reaction Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010010 raising Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of an amphoteric surfactant. The amphoteric surfactant is prepared from ethyl bromoacetate, triethyl phosphite, aldehyde (decanal, dodecanal, tetradecanal) and ethanolamine (N, N-dimethylethanolamine, diethanolamine, triethanolamine) through substitution reaction, wittig-horner reaction, aza-Michael addition reaction and hydrolysis reaction. The method is characterized in that: the oil-displacing surfactant contains hydroxyl and carboxyl as the head group, has good foamability and wettability, is excellent in temperature resistance and salt resistance, and is an amphoteric surfactant with high interfacial activity.
Description
Technical Field
The invention provides a preparation method of an amphoteric surfactant, and particularly relates to a novel multi-polar head-based surfactant for oil displacement, which is synthesized by adopting a mature chemical reaction.
Background
The role of petroleum in economic development is crucial, and the petroleum is one of indispensable 'nonrenewable resources', even affects the national safety, so that each country highly pays attention to the petroleum resources. Although China is vast in territory, the petroleum reserves of everyone are low. Complex underground petroleum storage environments with low permeability, high sand content, high temperature, high salinity and the like add greater problems to petroleum exploitation, the extraction amount of primary oil extraction and secondary oil extraction can not meet the market demand far away, and the development of efficient oil extraction technology becomes urgent under the eye, so that tertiary oil extraction technology comes into play. The tertiary oil recovery technology adopts the physical and chemical dual functions, and achieves the purpose of improving the recovery rate by reducing the interfacial tension. Most of oil fields in China are distributed in sedimentary basins, the oil fields have non-uniformity and are mixed with a large amount of gravel, and how to provide continuous and stable production by utilizing a tertiary oil recovery technology becomes a hot topic of petroleum workers.
According to the field effect of actual oil exploitation, the chemical oil displacement technology in the tertiary oil recovery technology is widely concerned with the advantages of high cost performance and the like. The high-temperature and high-salt oil storage environment improves the requirements of the surfactant for oil displacement, requires low interfacial tension, and also requires good compatibility with oil reservoirs and low price. The surfactant is a hydrophilic and oleophilic substance, can emulsify and reduce the viscosity of crude oil, reduce the tension of oil-water and oil-solid interfaces, reverse the wettability of rocks and change the rheological action. The surfactant includes ionic surfactant, amphoteric surfactant, biological surfactant, etc. At present, sulfonic acid type anionic surfactants are widely applied, but the interface activity is reduced due to the problems of poor degradability, poor antibacterial ability and the like. Cationic surfactants have good corrosion resistance and lubricity, but have a relatively low ability to reduce oil-water interfacial tension. The amphoteric surfactant has the advantages of good degradability, high interfacial activity, high universality and the like, and becomes a research hotspot of new oil displacement materials.
Researches find that the existence of hydroxyl can effectively improve the aggregation capability of the surfactant and has good wettability, foamability and solubility. The amphoteric surfactant has good biodegradability and low toxicity, and can realize the green and economic principle of the surfactant. Based on the advantages, the novel amphoteric surfactant synthesized has certain universality and can obviously reduce the oil-water interfacial tension.
Disclosure of Invention
The invention aims to design and synthesize an amphoteric surfactant. In order to achieve the purpose, the amphoteric surfactant is mainly prepared by taking ethyl bromoacetate, triethyl phosphite, aldehyde (decanal, dodecanal), ethanolamine (N, N-dimethylethanolamine, diethanolamine, triethanolamine) and the like as raw materials through a wittig-horner reaction, an aza-Michael addition reaction and a hydrolysis reaction.
The synthesis method mainly comprises the following steps:
the first step is as follows: preparation of wittig-horner reagent. Adding a certain amount of triethyl phosphite into a 250mL three-neck flask, heating to 120 ℃ by magnetic stirring, dropwise adding a certain amount of ethyl bromoacetate, heating to 130 ℃ after dropwise adding, and reacting for several hours to obtain the wittig-horner reagent.
The second step is that: preparation of alpha, beta-unsaturated carbonyl compounds. Placing a 100ml three-neck flask in an ice-water bath, adding a certain amount of tetrahydrofuran solvent, cooling to 0 ℃, adding a certain amount of wittig-horner reagent, mechanically stirring for 15 minutes, adding a certain amount of NaH, cooling to 0 ℃, dropwise adding a certain amount of aldehyde under nitrogen atmosphere, continuing to react for a plurality of hours, and obtaining the alpha, beta-unsaturated carbonyl compound by column chromatography.
The third step: and (3) preparing a surfactant intermediate. Weighing a certain mass of alpha, beta-unsaturated carbonyl compound and ethanolamine in a 100mL three-necked flask, magnetically stirring, heating, raising the temperature, adding a certain amount of sodium ethoxide, and reacting for several hours. After the reaction is finished, the solvent is removed by reduced pressure rotary evaporation to obtain a surfactant intermediate.
The fourth step: and (4) preparing a final product. Weighing a certain mass of surfactant intermediate in a 100ml three-necked bottle, adding a certain amount of ethanol solvent, heating and stirring, dropwise adding a certain amount of sodium hydroxide solution, reacting for several hours, and distilling under reduced pressure to remove the solvent to obtain the final product.
In the first step of the preparation process, the molar ratio of triethyl phosphite to ethyl bromoacetate is 1: 1-1: 1.2, the reaction time is 10-12 h, and the reaction temperature is 120-140 ℃, so that the Wittig-horner reagent is obtained.
In the invention, the second step of the preparation process is that the molar ratio of the wittig-horner reagent to the aldehyde is 1: 1-1: 1.2, the reaction time is 8-12 h, the reaction temperature is 0-5 ℃, the molar ratio of the catalyst sodium hydride to the aldehyde is 1: 1, and the corresponding alpha, beta-unsaturated carbonyl compound is obtained.
In the third step of the preparation process, the molar ratio of the alpha, beta-unsaturated carbonyl compound to the ethanolamine is 1: 1-1: 1.2, the reaction time is 8-12 h, the reaction temperature is 80-85 ℃, and the molar weight of the catalyst sodium ethoxide is 40%, so that the surfactant intermediate is obtained.
In the fourth step of the preparation process, the molar ratio of the surfactant intermediate to the sodium hydroxide is 1: 1-1: 1.3, the reaction time is 2-4 h, and the reaction temperature is 80-90 ℃ to obtain the final product.
The invention relates to a surfactant for oil displacement, which is applied to tertiary oil recovery and has the following outstanding advantages in synthesis and application:
1. the amphoteric surfactant has good biological activity, is easy to biodegrade, and accords with the green development concept.
2. The prepared surfactant has high interfacial activity, good temperature resistance and salt resistance, and oil-water interfacial tension which can reach an ultralow interfacial tension value, and has a certain application prospect in tertiary oil recovery.
Detailed Description
The invention will be further illustrated by the following examples, which are intended to provide a better understanding of the contents of the invention.
Example 1: preparation of wittig-horner reagent. Adding 16.80g of triethyl phosphite into a 250mL three-necked bottle, magnetically stirring, heating to 120 ℃, adding 16.88g of ethyl bromoacetate by using a dropping funnel, heating to 130 ℃ after the dropwise addition is finished, and continuously reacting for about 12 hours to obtain the wittig-horner reagent.
Example 2: preparation of alpha, beta-unsaturated carbonyl compounds. Weighing 2.80g of wittig-horner reagent, adding the wittig-horner reagent into a 100mL three-neck flask, adding 10mL of tetrahydrofuran solvent, cooling to 0 ℃ in an ice water bath, and adding 0.36g of sodium hydride. After mechanically stirring for 15 minutes, 1.83g of dodecanal is added dropwise, and stirring is continued for 8 hours under the protection of nitrogen, so that the alpha, beta-unsaturated carbonyl compound is obtained.
Example 3: and (3) preparing a surfactant intermediate. Weighing 1.24g of alpha, beta-unsaturated carbonyl compound prepared from dodecanal, adding the alpha, beta-unsaturated carbonyl compound into a 100ml three-neck flask, adding 10ml of ethanol, magnetically stirring, heating to 60 ℃, adding 0.27g of sodium ethoxide, continuing to react for half an hour, dropwise adding 0.54g N, N-dimethylethanolamine, heating to 80 ℃, reacting for 8 hours, and removing the solvent by vacuum rotary evaporation to obtain a surfactant intermediate.
Example 4: and (4) preparing a final product. Weighing 1.15g of surfactant intermediate prepared from N, N-dimethylethanolamine and 4g of ethanol, adding the surfactant intermediate and the ethanol into a 100ml three-neck flask at the temperature of 60 ℃, 8, dropwise adding 0.25ml of 50 mass percent sodium hydroxide solution by using a dropping funnel, refluxing for 4 hours at the temperature of 90 ℃, and removing the solvent after the reaction is finished to obtain the final product.
Example 5:
measuring the oil-water interfacial tension: preparing 0.3% surfactant aqueous solution, adding 3% sodium chloride by mass, stirring to dissolve completely, injecting the victory crude oil into a quartz tube, injecting the mixed solution into the tube, measuring the oil-water interfacial tension at 5000 r and 80 deg.C, and measuring the oil-water interfacial tension to 10-3mN/m。
Claims (5)
1. A preparation method of an amphoteric surfactant is realized by adopting a substitution reaction, a wittig-horner reaction, an aza-Michael addition reaction and a hydrolysis reaction, and is characterized by comprising the following steps:
the first step is as follows: and (3) carrying out substitution reaction on ethyl bromoacetate and triethyl phosphite to obtain the wittig-horner reagent.
The second step is that: wittig-horner reaction of wittig-horner reagent with aldehyde (decanal, dodecanal, tetradecanal) to obtain alpha, beta-unsaturated carbonyl compound.
The third step: and carrying out aza-Michael addition reaction on the alpha, beta-unsaturated carbonyl compound and ethanolamine (N, N-dimethylethanolamine, diethanolamine, triethanolamine) to obtain a surfactant intermediate.
The fourth step: and (3) carrying out hydrolysis reaction on the surfactant intermediate and sodium hydroxide to obtain a final product.
2. The preparation method of the first step according to claim 1, wherein the molar ratio of ethyl bromoacetate to triethyl phosphite is 1: 1-1: 1.2, the reaction time is 10-12 h, and the reaction temperature is 120-140 ℃.
3. The method according to claim 1, wherein the molar ratio of the wittig-horner reagent to the aldehyde (decanal, dodecanal, tetradecanal) is 1: 1 to 1: 1.2, the reaction time is 8 to 12 hours, and the reaction temperature is 0 to 5 ℃.
4. The preparation method of the third step of claim 1, wherein the molar ratio of the α, β -unsaturated carbonyl compound to the ethanolamine (N, N-dimethylethanolamine, diethanolamine, triethanolamine) is 1: 1 to 1: 1.2, the reaction time is 8 to 12 hours, and the reaction temperature is 80 to 85 ℃.
5. The preparation method of the fourth step of claim 1, wherein the molar ratio of the surfactant intermediate to the sodium hydroxide is 1: 1-1: 1.3, the reaction time is 2-4 h, and the reaction temperature is 80-100 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011069301.1A CN114410314A (en) | 2020-10-09 | 2020-10-09 | Preparation of amphoteric surfactant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011069301.1A CN114410314A (en) | 2020-10-09 | 2020-10-09 | Preparation of amphoteric surfactant |
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| Publication Number | Publication Date |
|---|---|
| CN114410314A true CN114410314A (en) | 2022-04-29 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011069301.1A Pending CN114410314A (en) | 2020-10-09 | 2020-10-09 | Preparation of amphoteric surfactant |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114410314A (en) |
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2020
- 2020-10-09 CN CN202011069301.1A patent/CN114410314A/en active Pending
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Application publication date: 20220429 |
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