CN115028826A - Diamino polyether surfactant and preparation method thereof - Google Patents
Diamino polyether surfactant and preparation method thereof Download PDFInfo
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- CN115028826A CN115028826A CN202111051895.8A CN202111051895A CN115028826A CN 115028826 A CN115028826 A CN 115028826A CN 202111051895 A CN202111051895 A CN 202111051895A CN 115028826 A CN115028826 A CN 115028826A
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 59
- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 53
- 229920000570 polyether Polymers 0.000 title claims abstract description 53
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000013067 intermediate product Substances 0.000 claims abstract description 27
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 24
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 23
- 150000001412 amines Chemical class 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 239000003513 alkali Substances 0.000 claims abstract description 13
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 12
- 238000003756 stirring Methods 0.000 claims abstract description 12
- 238000010992 reflux Methods 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 238000009833 condensation Methods 0.000 claims abstract description 3
- 230000005494 condensation Effects 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 4
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 claims description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 claims description 3
- OVISMSJCKCDOPU-UHFFFAOYSA-N 1,6-dichlorohexane Chemical compound ClCCCCCCCl OVISMSJCKCDOPU-UHFFFAOYSA-N 0.000 claims description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 3
- 239000000920 calcium hydroxide Substances 0.000 claims description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 3
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims description 2
- GBBZLMLLFVFKJM-UHFFFAOYSA-N 1,2-diiodoethane Chemical compound ICCI GBBZLMLLFVFKJM-UHFFFAOYSA-N 0.000 claims description 2
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 claims description 2
- AAAXMNYUNVCMCJ-UHFFFAOYSA-N 1,3-diiodopropane Chemical compound ICCCI AAAXMNYUNVCMCJ-UHFFFAOYSA-N 0.000 claims description 2
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 claims description 2
- ROUYUBHVBIKMQO-UHFFFAOYSA-N 1,4-diiodobutane Chemical compound ICCCCI ROUYUBHVBIKMQO-UHFFFAOYSA-N 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 239000002585 base Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 abstract description 8
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 8
- 239000000243 solution Substances 0.000 description 13
- 230000000694 effects Effects 0.000 description 8
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 2
- 239000003129 oil well Substances 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000015784 hyperosmotic salinity response Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
- C08G65/2621—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups
- C08G65/2624—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups containing aliphatic amine groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
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- 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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- 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
- C09K8/602—Compositions for stimulating production by acting on the underground formation containing surfactants
- C09K8/604—Polymeric surfactants
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Abstract
The invention relates to a diamino polyether surfactant, which has the following structural formula:
a preparation method of a diamino polyether surfactant comprises the following steps: (1) adding a certain amount of fatty amine into an autoclave, adding a proper amount of alkali, vacuumizing, removing air, heating to 80-150 ℃, stirring, slowly adding a certain amount of ethylene oxide for reacting for 5-10 hours, and then adding a certain amount of propylene oxide for reacting for 5-10 hours to obtain an intermediate product; (2) adding a proper amount of alcohol solvent into the autoclave, then dropwise adding a certain amount of dihalogenated hydrocarbon, and adjusting the temperature to 60-12 DEG CAfter the temperature is 0 ℃, a reflux pipe is used for condensation reflux reaction or stirring reaction for 8-20h, and the diamino polyether surfactant is obtained after the reaction is finished.
Description
Technical Field
The invention belongs to the field of chemical engineering, and particularly relates to a diamino polyether surfactant and a preparation method thereof.
Background
The low-permeability oil reservoir has the characteristics of low porosity and low permeability, and has the problem that the water injection pressure is high, so that the water injection effect of the oil well is difficult to see, and the problem is still serious although the oil well is fractured.
Indoor tests show that: the surfactant can reduce the injection pressure and improve the recovery ratio to a certain extent. Therefore, chemical flooding is an effective method for solving the development effect of ultra-low permeability reservoirs.
At present, the displacement experiment is generally carried out mainly by adopting an anionic surfactant, an anionic-nonionic amphoteric surfactant, a compound system of the anionic surfactant and alcohol in the indoor research and the mine field experiment, so that the obvious effects of reducing the pressure and increasing the injection are achieved, and the method is a promising method for solving the problem of high injection pressure at present.
At present, the conventional anionic surfactant has good interfacial property, is temperature-resistant, does not have cloud point, has small adsorption amount on the surface of sandstone, is low in price and various in types, but has the defect of poor temperature resistance and salt tolerance, and can not meet the requirements of high-temperature and high-salt oil reservoirs. The nonionic surfactant has good oil washing effect but cloud point and poor temperature resistance. Due to the complexity of low-permeability, high-temperature and high-salt oil reservoirs, new requirements are put forward for the conventional oil displacement surfactant system.
Disclosure of Invention
The purpose of the invention is as follows: aiming at the problems of oil displacement of the existing surfactant, the invention provides a diamino polyether surfactant and a preparation method thereof.
The invention is realized by the following technical scheme:
a diamino polyether surfactant has the following structural formula:
r is C8-C16 alkane;
EO is ethylene oxide, m is an integer, and m is more than or equal to 1 and less than or equal to 100;
PO is propylene oxide, n is an integer, and n is more than or equal to 1 and less than or equal to 100;
x is a positive integer, and x is more than or equal to 1 and less than or equal to 6.
A preparation method of a diamino polyether surfactant comprises the following steps:
(1) adding a certain amount of fatty amine into an autoclave, adding a proper amount of alkali, vacuumizing, heating to 80-150 ℃, stirring, slowly adding a certain amount of ethylene oxide to react for 5-10 hours, and then adding a certain amount of propylene oxide to react for 5-10 hours to obtain an intermediate product;
(2) adding a proper amount of alcohol solvent into the autoclave, then dropwise adding a certain amount of dihalohydrocarbon, adjusting the temperature to 60-120 ℃, then carrying out condensation reflux reaction or stirring reaction for 8-20h by a return pipe, and obtaining the diamino polyether surfactant after the reaction is finished.
Further, the fatty amine in the step (1) is fatty primary amine.
Further, the molar ratio of the fatty amine to the ethylene oxide and the propylene oxide in the step (1) is 1: (2-200): (2-200).
Further, the molar ratio of the aliphatic amine to the ethylene oxide and the propylene oxide in the step (1) is 1: (5-20): (5-20).
Further, the molar ratio of the intermediate product obtained in the step (1) to the dihalohydrocarbon is (1.5-5): 1.
Further, the molar ratio of the intermediate product obtained in the step (1) to the dihalogenated hydrocarbon is (3-4): 1.
Further, the dihalo-hydrocarbon is one of 1, 2-dichloroethane, 1, 3-dichloropropane, 1, 4-dichlorobutane, 1, 6-dichlorohexane, 1, 2-dibromoethane, 1, 3-dibromopropane, 1, 4-dibromobutane, 1, 2-diiodoethane, 1, 3-diiodopropane and 1, 4-diiodobutane.
Further, the alcohol solution in the step (2) is one of ethanol, isopropanol, n-propanol, n-butanol, isobutanol and isoamylol, and the dosage of the alcohol solution is 20-50% of the total mass of the intermediate product obtained in the step (1).
Further, in the step (1), the alkali is one of potassium hydroxide, sodium hydroxide and calcium hydroxide, and the using amount of the alkali is 1-3% of the mass of the fatty amine.
Has the advantages that: the invention discloses a diamino polyether surfactant and a preparation method thereof, and the diamino polyether surfactant has the following beneficial effects:
the diamino polyether surfactant disclosed by the invention has high surface (interface) activity similar to that of gemini surfactants, has strong oil washing performance of the polyether surfactant, has good temperature and salt resistance, and meets the use requirements of low-permeability high-temperature high-salt oil reservoirs.
Drawings
FIG. 1 is an infrared spectrum of the bisamino polyether gemini surfactant prepared in example 4.
The specific implementation mode is as follows:
the following describes in detail specific embodiments of the present invention.
Example 1
A preparation method of a diamino polyether surfactant comprises the following steps:
step (1): in a high-pressure reaction kettle, 22g of ethylene oxide and 29g of propylene oxide are dropwise added into 12.8g of octylamine to react for 8 hours, 2g of NaOH solid particles are added, the temperature is adjusted to 80 ℃, and the reaction is carried out for 9 hours to obtain an intermediate product A;
step (2): and (3) dissolving the intermediate product A in an n-propanol solution, continuously dropwise adding 5.05g of 1, 2-dichloroethane into the product solution, adjusting the temperature to 60 ℃, condensing and refluxing through a reflux pipe, and reacting for 20 hours to obtain the diamino polyether surfactant.
Example 2
A preparation method of a diamino polyether surfactant comprises the following steps:
step (1): putting 44g of ethylene oxide and 58g of propylene oxide into a separating funnel, dropwise adding the mixture into 18.4g of dodecylamine solvent to react for 5 hours in a high-pressure reaction kettle, adding 3g of NaOH, adjusting the temperature to 120 ℃, and reacting for 10 hours to obtain an intermediate product A;
step (2): and (3) dissolving the intermediate product A in an isopropanol solution, continuously dropwise adding 5.75g of 1, 3-dichloropropane into the product solution, adjusting the temperature to 100 ℃, condensing and refluxing a reflux pipe, and reacting for 12 hours to obtain the diamino polyether surfactant.
Example 3
A preparation method of a diamino polyether surfactant comprises the following steps:
step (1): putting 66g of ethylene oxide and 87g of propylene oxide into a separating funnel, dropwise adding 24g of hexadecylamine solvent into the separating funnel, reacting for 10 hours, adding 4g of NaOH, adjusting the temperature to 150 ℃, and reacting for 5 hours to obtain an intermediate product A;
step (2): dissolving the intermediate product A in n-butanol solution, continuously dropwise adding 7.85g of 1, 6-dichlorohexane into the product solution, adjusting the temperature to be below 120 ℃, condensing and refluxing through a reflux pipe, and reacting for 8 hours to obtain the diamino polyether surfactant.
The surface tension of the bisamino polyether surfactant was tested by a surface tensiometer. The results are shown in Table 1. The high surface activity of the diamine polyether surfactant prepared by the method can be seen.
| Name of surfactant | Concentration of | Surface tension (mN/m) |
| Bis- |
1％ | <29 |
The surface tension measurement shows that the surface tension of the diamino polyether surfactant disclosed by the invention is obviously lower than that of the diamino polyether surfactant in comparative example 1, so that the diamino polyether surfactant disclosed by the invention has good surface activity and can effectively reduce the surface tension of oil and water.
Surface tension measurement after high-temperature treatment shows that the surface tension value of the diamino polyether surfactant is unchanged or is not obviously changed after the diamino polyether surfactant is subjected to high-temperature treatment at 150 ℃ for 2 days, which shows that the diamino polyether surfactant has good temperature resistance and stable activity at 150 ℃.
Surface tension measurement after high-salt treatment shows that the surface tension value of the diamino polyether surfactant is unchanged or is not obviously changed after the diamino polyether surfactant is treated by brine with the concentration of 40000mg/L, which indicates that the diamino polyether surfactant has good salt resistance.
| Name of surfactant | Concentration of | Interfacial tension |
| Bis- |
1％ | <30 |
Example 4
A diamino polyether surfactant has the following structural formula:
r is C8 alkane (C8 straight-chain n-alkane);
EO is ethylene oxide, m is an integer, and m is 1;
PO is propylene oxide, n is an integer, and n is 10;
x is a positive integer, and x is 1.
A preparation method of a diamino polyether surfactant comprises the following steps:
(1) adding a certain amount of fatty amine into an autoclave, adding a proper amount of alkali, vacuumizing, removing air, heating to 80 ℃, stirring, slowly adding a certain amount of ethylene oxide for reacting for 10 hours, and then adding a certain amount of propylene oxide for reacting for 10 hours to obtain an intermediate product;
(2) adding a proper amount of alcohol solvent into the autoclave, then dropwise adding a certain amount of dihalohydrocarbon, adjusting the temperature to 60 ℃, stirring for reaction for 20 hours, and obtaining the diamino polyether surfactant after the reaction is finished. Infrared spectrum detection is performed on the diamino polyether surfactant obtained in this example, and fig. 1 is an infrared spectrum of the diamino polyether gemini surfactant prepared in example 4.
Further, the fatty amine in the step (1) is fatty primary amine.
Further, the mole ratio of the aliphatic amine to the ethylene oxide and the propylene oxide in the step (1) is 1: 2: 2.
in another embodiment: the molar ratio of the fatty amine to the ethylene oxide to the propylene oxide in the step (1) is 1: 5: 5.
further, the molar ratio of the intermediate product obtained in the step (1) to the dihalogenated hydrocarbon is 1.5: 1.
In another embodiment, the molar ratio of the intermediate product obtained in step (1) to the dihalogenated hydrocarbon is 3: 1.
Further, the dihalohydrocarbon is 1, 2-dichloroethane.
Further, in the step (2), the alcohol solution is ethanol, and the dosage of the alcohol solution is 20% of the total mass of the intermediate product obtained in the step (1).
Further, in the step (1), the alkali is potassium hydroxide, and the dosage of the potassium hydroxide is 1 percent of the mass of the fatty amine.
Example 5
A diamino polyether surfactant has the following structural formula:
r is C16 alkane (C16 straight-chain n-alkane);
EO is ethylene oxide, m is an integer, and m is 100;
PO is propylene oxide, n is an integer, and n is 100;
x is a positive integer, and x is 6.
A preparation method of a diamino polyether surfactant comprises the following steps:
(1) adding a certain amount of fatty amine into an autoclave, adding a proper amount of alkali, vacuumizing, exhausting air, heating to 150 ℃, stirring, slowly adding a certain amount of ethylene oxide for reacting for 10 hours, and then adding a certain amount of propylene oxide for reacting for 10 hours to obtain an intermediate product;
(2) adding a proper amount of alcohol solvent into the autoclave, then dropwise adding a certain amount of dihalohydrocarbon, adjusting the temperature to 120 ℃, stirring and reacting for 8 hours, and obtaining the diamino polyether surfactant after the reaction is finished.
Further, the fatty amine in the step (1) is fatty primary amine.
Further, the molar ratio of the fatty amine to the ethylene oxide and the propylene oxide in the step (1) is 1: 200: 200.
in another embodiment: the molar ratio of the fatty amine to the ethylene oxide to the propylene oxide in the step (1) is 1: 20: 20.
further, the molar ratio of the intermediate product obtained in the step (1) to the dihalogenated hydrocarbon is 5: 1.
In another embodiment: the molar ratio of the intermediate product obtained in step (1) to the dihalogenated hydrocarbon is 4: 1.
Further, the dihalohydrocarbon is 1, 3-dichloropropane.
Further, the alcohol solution in the step (2) is isopropanol, and the dosage of the isopropanol is 50% of the total mass of the intermediate product obtained in the step (1).
Further, in the step (1), the alkali is sodium hydroxide, and the dosage of the alkali is 2% of the mass of the fatty amine.
Example 6
A diamino polyether surfactant has the following structural formula:
r is C10 alkane (C10 straight-chain n-alkane);
EO is ethylene oxide, m is an integer, and m is 50;
PO is propylene oxide, n is an integer, and n is 40;
x is a positive integer, and x is 4.
A preparation method of a diamino polyether surfactant comprises the following steps:
(1) adding a certain amount of fatty amine into an autoclave, adding a proper amount of alkali, vacuumizing, removing air, heating to 100 ℃, stirring, slowly adding a certain amount of ethylene oxide for reacting for 6 hours, and then adding a certain amount of propylene oxide for reacting for 8 hours to obtain an intermediate product;
(2) adding a proper amount of alcohol solvent into the autoclave, then dropwise adding a certain amount of dihalohydrocarbon, adjusting the temperature to 80 ℃, stirring for reaction for 16 hours, and obtaining the diamino polyether surfactant after the reaction is completed.
Further, the fatty amine in the step (1) is fatty primary amine.
Further, the molar ratio of the fatty amine to the ethylene oxide and the propylene oxide in the step (1) is 1: 50: 60.
in another embodiment: the molar ratio of the fatty amine to the ethylene oxide to the propylene oxide in the step (1) is 1: 10: 15.
further, the molar ratio of the intermediate product obtained in the step (1) to the dihalogenated hydrocarbon is 3: 1.
In another embodiment: the molar ratio of the intermediate product obtained in step (1) to the dihalogenated hydrocarbon was 3.5: 1.
Further, the dihalohydrocarbon is 1, 4-dichlorobutane.
Further, the alcohol solution in the step (2) is n-propanol, and the amount thereof is 34% of the total mass of the intermediate product obtained in the step (1).
Further, in the step (1), the alkali is calcium hydroxide, and the dosage of the alkali is 3% of the mass of the fatty amine.
Examples 7 to 15
The difference is essentially the same as in example 4, except that the dihalo-hydrocarbon, alcohol solution is different:
the embodiments of the present invention have been described in detail. However, the present invention is not limited to the above-described embodiments, and various changes can be made within the knowledge of those skilled in the art without departing from the spirit of the present invention.
Claims (10)
1. The diamine polyether surfactant is characterized by having a structural formula as follows:
r is C8-C16 alkane;
EO is ethylene oxide, m is an integer and is not less than 1 and not more than 100;
PO is propylene oxide, n is an integer, and n is more than or equal to 1 and less than or equal to 100;
x is a positive integer, and x is more than or equal to 1 and less than or equal to 6.
2. The preparation method of the diamino polyether surfactant is characterized by comprising the following steps:
(1) adding a certain amount of fatty amine into an autoclave, adding a proper amount of alkali, vacuumizing, heating to 80-150 ℃, stirring, slowly adding a certain amount of ethylene oxide for reacting for 5-10 hours, and then adding a certain amount of propylene oxide for reacting for 5-10 hours to obtain an intermediate product;
(2) adding a proper amount of alcohol solvent into the autoclave, then dropwise adding a certain amount of dihalohydrocarbon, adjusting the temperature to 60-120 ℃, then carrying out condensation reflux reaction or stirring reaction for 8-20h by a return pipe, and obtaining the diamino polyether surfactant after the reaction is finished.
3. The method for preparing a diamino polyether surfactant as claimed in claim 2 wherein said fatty amine in step (1) is a primary fatty amine.
4. The method of claim 2, wherein the molar ratio of the aliphatic amine to the ethylene oxide to the propylene oxide in step (1) is 1: (2-200): (2-200).
5. The method of claim 4, wherein the molar ratio of the aliphatic amine to the ethylene oxide to the propylene oxide in step (1) is 1: (5-20): (5-20).
6. The method for preparing the diamino polyether surfactant as claimed in claim 2, wherein the molar ratio of the intermediate product obtained in the step (1) to the dihalo-hydrocarbon is (1.5-5): 1.
7. The method for preparing a diamino polyether surfactant as claimed in claim 6, wherein the molar ratio of the intermediate product obtained in step (1) to the dihalo-hydrocarbon is (3-4): 1.
8. The method of claim 2, wherein the dihalohydrocarbon is one of 1, 2-dichloroethane, 1, 3-dichloropropane, 1, 4-dichlorobutane, 1, 6-dichlorohexane, 1, 2-dibromoethane, 1, 3-dibromopropane, 1, 4-dibromobutane, 1, 2-diiodoethane, 1, 3-diiodopropane, and 1, 4-diiodobutane.
9. The method for preparing a diamino polyether surfactant as claimed in claim 2, wherein said alcohol solution in step (2) is one of ethanol, isopropanol, n-propanol, n-butanol, isobutanol, isoamyl alcohol in an amount of 20% to 50% of the total mass of the intermediate product obtained in step (1).
10. The method for preparing a diamino polyether surfactant as claimed in claim 2, wherein said base in step (1) is one of potassium hydroxide, sodium hydroxide and calcium hydroxide, and its amount is 1-3% of the mass of fatty amine.
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