CN108117639B - Unsaturated fatty alcohol polyoxypropylene polyoxyethylene block copolymer, and preparation method and application thereof - Google Patents
Unsaturated fatty alcohol polyoxypropylene polyoxyethylene block copolymer, and preparation method and application thereof Download PDFInfo
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- CN108117639B CN108117639B CN201611090317.4A CN201611090317A CN108117639B CN 108117639 B CN108117639 B CN 108117639B CN 201611090317 A CN201611090317 A CN 201611090317A CN 108117639 B CN108117639 B CN 108117639B
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- enol
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- fatty alcohol
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- -1 polyoxypropylene Polymers 0.000 title claims abstract description 225
- 229920001451 polypropylene glycol Polymers 0.000 title claims abstract description 87
- 229920001400 block copolymer Polymers 0.000 title claims abstract description 68
- 229920003171 Poly (ethylene oxide) Polymers 0.000 title claims abstract description 56
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 150000002191 fatty alcohols Chemical class 0.000 title abstract description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000003921 oil Substances 0.000 claims abstract description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000010779 crude oil Substances 0.000 claims abstract description 20
- WFZQLUSOXHIVKL-QXMHVHEDSA-N ethyl (13Z)-docosenoate Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OCC WFZQLUSOXHIVKL-QXMHVHEDSA-N 0.000 claims abstract description 15
- 238000011084 recovery Methods 0.000 claims abstract description 13
- 238000007046 ethoxylation reaction Methods 0.000 claims abstract description 12
- 230000009467 reduction Effects 0.000 claims abstract description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 10
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000004945 emulsification Methods 0.000 claims abstract description 10
- 238000007142 ring opening reaction Methods 0.000 claims abstract description 10
- 150000002085 enols Chemical class 0.000 claims abstract description 9
- 229910052751 metal Inorganic materials 0.000 claims abstract description 8
- 239000002184 metal Substances 0.000 claims abstract description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 6
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 6
- 239000011734 sodium Substances 0.000 claims abstract description 6
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- 238000011161 development Methods 0.000 abstract description 5
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- 238000006243 chemical reaction Methods 0.000 description 16
- DTPCFIHYWYONMD-UHFFFAOYSA-N decaethylene glycol Polymers OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO DTPCFIHYWYONMD-UHFFFAOYSA-N 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 11
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000002131 composite material Substances 0.000 description 8
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 7
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- 238000010438 heat treatment Methods 0.000 description 5
- 229920002401 polyacrylamide Polymers 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
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- 238000001819 mass spectrum Methods 0.000 description 4
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- 238000003786 synthesis reaction Methods 0.000 description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000011964 heteropoly acid Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
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- 238000005516 engineering process Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
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- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000019737 Animal fat Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- 229920002675 Polyoxyl Polymers 0.000 description 1
- 244000018633 Prunus armeniaca Species 0.000 description 1
- 235000009827 Prunus armeniaca Nutrition 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000001076 estrogenic effect Effects 0.000 description 1
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- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
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- 239000010865 sewage Substances 0.000 description 1
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- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003930 superacid Substances 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
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- 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
- C08G65/2603—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 oxygen
- C08G65/2606—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 oxygen containing hydroxyl groups
- C08G65/2609—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 oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
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- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/02—Well-drilling compositions
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- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/588—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 polymers
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Abstract
The invention provides an unsaturated fatty alcohol polyoxypropylene polyoxyethylene block copolymer, and a preparation method and application thereof. The polymer is a C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer containing unsaturated double bonds, and has a structure shown in a general formula I, and the preparation method comprises the following steps: reacting ethyl erucate with anhydrous acetic acid and a metal sodium tablet, and performing reduced pressure fractionation to obtain C22 enol; c22 enol and epoxypropane carry out ring-opening reaction to obtain C22 enol polyoxypropylene ether; c22 enol polyoxypropylene ether and epoxy ethane are subject to ethoxylation reaction to obtain C22 enol polyoxypropylene polyoxyethylene block copolymer. The C22 enol polyoxypropylene polyoxyethylene block copolymer has excellent thickening performance of emulsified high-viscosity crude oil and aqueous solution, and has wide application potential in the fields of thick oil emulsification viscosity reduction, high wax content crude oil pour point reduction and low-permeability oilfield tertiary oil recovery development.
Description
Technical Field
The invention relates to an unsaturated fatty alcohol polyoxypropylene polyoxyethylene block copolymer, a preparation method and application thereof, in particular to a C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer containing unsaturated double bonds for tertiary oil recovery, a preparation method thereof and application thereof in the field of tertiary oil recovery, and belongs to the technical field of surfactants for tertiary oil recovery.
Background
The fatty alcohol polyoxypropylene polyoxyethylene block copolymer is a novel nonionic surfactant, and the lipophilicity of the surfactant molecule is improved due to the hydrophobic property of the polyoxypropylene block; meanwhile, due to the existence of hydrogen bonds among the polyoxypropylene block molecules, when the molecular weight is increased and exceeds a certain concentration, the intermolecular interaction is increased, a space network structure is formed, and the viscosity of the solution is increased; the polyoxyethylene block can increase the viscosity of the polymer solution due to the strong interaction with the water-soluble polymer. Due to the characteristics of the fatty alcohol polyoxypropylene polyoxyethylene block copolymer, the fatty alcohol polyoxypropylene polyoxyethylene block copolymer has good application prospect in the field of tertiary oil recovery.
In the prior art, the fatty alcohol used for preparing the fatty alcohol polyoxypropylene polyoxyethylene block copolymer mainly comes from animal and vegetable fat and is mainly C12-C18 fatty alcohol.
On the other hand, the chemical flooding technology is mainly applied to Daqing oil fields in China. Crude oil components of Daqing oil field are mainly divided into alkanes, aromatics, colloids and asphaltenes, as shown in Table 1.
Table 1 main components of crude oil in daqing oil field
| Oil field | Total hydrocarbons% | Saturated hydrocarbon% | Aromatic hydrocarbons% | Colloid% | Asphalt% |
| Chan loudspeaker | 81.9 | 57.1 | 24.8 | 17.3 | 0.5 |
| Saer diagram | 78.8 | 62.6 | 16.2 | 20 | 1.2 |
| Apricot tree post | 84.8 | 66.3 | 18.5 | 14.3 | 0.9 |
| High table | 87.1 | 71.6 | 15.5 | 11.7 | 1.2 |
| Grape flower | 89.0 | 70.1 | 18.9 | 10.5 | 0.5 |
However, practical application experiments show that the current fatty alcohol polyoxypropylene polyoxyethylene block copolymer is not ideal in effect when applied to the chemical flooding technology of Daqing oil fields.
Disclosure of Invention
One object of the present invention is to provide a novel fatty alcohol polyoxypropylene polyoxyethylene block copolymer, which is applied to the field of tertiary oil recovery.
Another object of the present invention is to provide a method for preparing the novel fatty alcohol polyoxypropylene polyoxyethylene block copolymer.
Another object of the present invention is to provide the use of the novel fatty alcohol polyoxypropylene polyoxyethylene block copolymers.
In one aspect, the present invention provides a novel fatty alcohol polyoxypropylene polyoxyethylene block copolymer, which is a C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer containing unsaturated double bonds.
The C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer containing unsaturated double bonds provided by the invention has a structure shown in a general formula I:
wherein p and q are each independently a positive integer selected from 1 to 5000, such as 1, 2, 3 … … … 4998, 4999 or 5000.
According to a preferred embodiment of the present invention, in the unsaturated double bond-containing C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer, p is a positive integer selected from 5 to 1000, such as 5, 6 … … … 998, 999 or 1000. More preferably, p is a positive integer selected from 5 to 50, such as 5, 6 … … … 49 or 50.
According to a preferred embodiment of the present invention, in the unsaturated double bond-containing C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer, q is a positive integer selected from 5 to 1000, such as 5, 6 … … … 998, 999 or 1000. More preferably, q is a positive integer selected from 5 to 50, such as 5, 6 … … … 49 or 50.
In a specific embodiment of the present invention, the C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer containing an unsaturated double bond provided by the invention, wherein p is 5 and q is 20.
In another specific embodiment of the present invention, the C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer containing unsaturated double bonds provided by the present invention, wherein p is 10 and q is 10.
In another aspect, the invention also provides a method for preparing the C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer containing unsaturated double bonds.
According to a specific embodiment of the present invention, the method for preparing the unsaturated double bond-containing C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer comprises the following steps:
preparation of C22 enol: mixing erucic acid ethyl ester and anhydrous acetic acid, and reacting under the action of metal sodium to obtain C22 enol;
ring opening reaction: c22 enol and epoxypropane are subjected to ethoxylation reaction under the action of a catalyst to obtain C22 enol polyoxypropylene ether;
ethoxylation reaction: c22 enol polyoxypropylene ether and epoxy ethane are subject to ethoxylation reaction under the action of catalyst to obtain C22 enol polyoxypropylene polyoxyethylene block copolymer.
According to a specific embodiment of the present invention, the preparation method of the unsaturated double bond-containing C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer further comprises a process for preparing the ethyl erucate. Specifically, the process for preparing the erucic acid ethyl ester comprises the following steps:
preparing ethyl erucate: erucic acid and ethanol are subjected to condensation reaction under the action of an acid catalyst to obtain erucic acid ethyl ester.
According to a specific embodiment of the present invention, in the preparation method of the C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer containing unsaturated double bonds, the acid catalyst comprises one or more of sulfuric acid, hydrofluoric acid, methanesulfonic acid, trifluoromethanesulfonic acid, metal trifluoromethanesulfonate or supported trifluoromethanesulfonate, heteropolyacid, solid super acid, perfluorosulfonic acid-polytetrafluoroethylene copolymer and acidic zeolite in the preparation of ethyl erucate.
According to a specific embodiment of the present invention, the C22 fatty alcohol polyoxyl containing unsaturated double bond of the present inventionIn the preparation method of the propylene polyoxyethylene block copolymer, the catalyst used in the ring-opening reaction process is an acid catalyst. More specifically, the acidic catalyst comprises BF3、SbCl4、SnCl4One or more of solid acid, heteropoly acid, perfluoro sulfonic acid-polytetrafluoroethylene copolymer and supported molecular sieve catalyst. Or the acid catalyst comprises one or more of potassium hydroxide, sodium methoxide, sodium ethoxide, Mg/Al composite oxide, barium oxide and hydroxide, alkoxy aluminum sulfonate, rare metal alkoxy sulfate, and a composite of alkaline earth metal oxide and phosphoric acid. One of potassium hydroxide, sodium methoxide and Mg/Al composite oxide is preferable.
According to a specific embodiment of the present invention, in the preparation method of the unsaturated double bond-containing C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer, the catalyst used in the ethoxylation reaction is an acid catalyst. More specifically, the acidic catalyst comprises BF3、SbCl4、SnCl4One or more of solid acid, heteropoly acid, perfluoro sulfonic acid-polytetrafluoroethylene copolymer and supported molecular sieve catalyst. Or the acid catalyst comprises one or more of potassium hydroxide, sodium methoxide, sodium ethoxide, Mg/Al composite oxide, barium oxide and hydroxide, alkoxy aluminum sulfonate, rare metal alkoxy sulfate, and a composite of alkaline earth metal oxide and phosphoric acid. One of potassium hydroxide, sodium methoxide and Mg/Al composite oxide is preferable.
According to a specific embodiment of the present invention, the product obtained by the method for preparing the unsaturated double bond-containing C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer comprises the unsaturated double bond-containing C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer of the present invention as described above.
Further, in the above-mentioned technical means, the size of the polyoxypropylene block or the polyoxyethylene block is adjusted depending on the purpose of use, and a suitable polyoxypropylene polyoxyethylene block copolymer can be obtained.
Furthermore, in the above technical solution, the ring opening reaction of the C22 enol and propylene oxide according to the present invention is preferably performed such that the molar ratio of the C22 enol to propylene oxide is 1: 5 to 50.
Furthermore, in the technical scheme, the C22 enol polyoxypropylene ether and the ethylene oxide are subjected to ethoxylation reaction, and preferably, the molar ratio of the C22 enol polyoxypropylene ether to the ethylene oxide is 1: 10 to 50 reaction.
The C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer containing unsaturated double bonds has a hydrophobic structure close to that of crude oil, and has stronger solubilizing effect on the crude oil, especially the crude oil with high wax content; meanwhile, the modified polyurethane has unsaturated double bonds, so that the modified polyurethane has better fluidity and hydrophilicity; the molecular weight of the surfactant is greatly increased by the block of the polyoxypropylene and the polyoxyethylene, so that the viscosity of an aqueous solution is remarkably increased, and the viscosity of the aqueous solution is remarkably increased in the field of tertiary oil recovery compared with that of a single polymer when the aqueous solution is compounded with the polymer; in the field of low-permeability development, the C22 enol polyoxypropylene polyoxyethylene block copolymer single aqueous solution system or the C22 enol polyoxypropylene polyoxyethylene block copolymer single aqueous solution system compounded with a low molecular weight polymer can be effectively injected, has higher viscosity and plays a role in controlling fluidity.
On the other hand, the invention also provides application of the C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer containing unsaturated double bonds in thick oil emulsification and viscosity reduction.
On the other hand, the invention also provides the application of the C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer containing unsaturated double bonds in pour point depressing of high wax content crude oil.
On the other hand, the invention also provides the application of the C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer containing unsaturated double bonds in chemical flooding tertiary oil recovery.
The beneficial results of the invention are:
1. the C22 alkane chain structure and the polyoxypropylene block are both oil-soluble, have very strong intermiscibility with crude oil, thick oil and high-solidifying crude oil, can control the hydrophilic-lipophilic balance of the block copolymer by controlling the size of the ethylene oxide block, and can be widely applied to the fields of residual oil emulsification, thick oil viscosity reduction, crude oil emulsification and the like;
2. the C22 enol polyoxypropylene polyoxyethylene block copolymer contains unsaturated double bonds, has good fluidity and water solubility, is suitable for application in tertiary oil recovery chemical flooding, and has the performances of emulsification, solubilization, wetting and the like;
3. the C22 fatty alcohol polyoxypropylene polyoxyethylene segmented copolymer containing unsaturated double bonds has larger molecular weight, and when the molecular weight exceeds a certain concentration, rod-shaped micelles are easily formed in water solution, and a space network structure can be formed along with the further increase of the concentration, so that the thickening effect is good; due to intermolecular hydrogen bonds, the block copolymer and the traditional polyacrylamide macromolecules have good synergistic tackifying performance, and the block copolymer is particularly suitable for being applied under the condition that a high molecular weight polymer of a low-permeability oil field is not suitable for use;
4. the preparation method of the unsaturated double bond-containing C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer has high conversion rate and is suitable for industrial production.
Therefore, the C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer containing unsaturated double bonds has very important application and development prospects.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of C22 enol prepared in example 1.
FIG. 2 is an electrospray mass spectrum of C22 enol polyoxypropylene (10) prepared in example 1.
FIG. 3 is an electrospray mass spectrum of C22 enol polyoxypropylene (10) polyoxyethylene (10) ether prepared in example 1.
Detailed Description
For a more clear understanding of the technical features, objects and advantages of the present invention, reference is now made to the following detailed description of the embodiments of the present invention taken in conjunction with the accompanying drawings, which are included to illustrate and not to limit the scope of the present invention.
Example 1
In this example, an unsaturated double bond-containing C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer was prepared using erucic acid C22 as a starting material. The specific operation is as follows.
1. Esterification reaction
(1) The reaction formula is as follows:
CH3(CH2)7CH＝CH(CH2)11COOH+CH3CH2OH→CH3(CH2)7CH＝CH(CH2)11COOCH2CH3+H2O
(2) raw material specification:
the content of industrial grade high-purity erucic acid C22: 1 is more than 95 percent, and the iodine value (gI)2100g)80-90 percent, the water content is less than 0.5 percent, the ethanol content is more than 99.0 percent, and the water content is less than 0.1 percent
(3) The raw material ratio is as follows:
erucic acid: ethanol ═ 1: 5 (molar ratio)
(4) The synthesis process comprises the following steps:
adding erucic acid and ethanol into a reaction kettle according to a molar ratio of 1: 5 (molar ratio), heating to 90 ℃, starting to react, gradually supplementing ethanol in the reaction process (ethanol is fully excessive, so that the esterification reaction is carried out in a positive direction, the ethanol supplementation amount is 1-3 molar ratio of the erucic acid raw material), finishing the reaction after 2 hours, and removing generated water and excessive ethanol by adopting a rotary evaporation device through reduced pressure distillation at 130 ℃ to obtain erucic acid ethyl ester (CH)3(CH2)7CH＝CH(CH2)11COOCH2CH3)。
2. Preparation of C22 enol
(1) The reaction formula is as follows:
(2) specification:
the acetic acid content is more than 99.0 percent, and the water content is less than 0.1 percent; the ethanol content is more than 99.0 percent, and the water content is less than 0.1 percent.
(3) The synthesis process comprises the following steps:
in a 250ml three-neck flask,erucic acid ethyl ester and anhydrous acetic acid are mixed (20 g of erucic acid ethyl ester is added, the mol ratio of the erucic acid ethyl ester to the anhydrous acetic acid is 1: 3), 0.1g of metal sodium sheet is rapidly added, and the reaction is vigorously carried out. After the reaction is mild, 20ml of absolute ethyl alcohol is added, and the mixture is heated until the metallic sodium completely reacts. Then adding water and refluxing for 1h at 100 ℃ to saponify the unreacted ethyl erucate. After cooling, the organic phase is extracted with 100ml of ether, then 0.1mol/LNaOH is added, the excess acetic acid is neutralized and dried, the ether is evaporated, then the reduced pressure fractionation is carried out, and the 150-3(CH2)7CH＝CH(CH2)11CH2OH)。
The nuclear magnetic spectrum of the C22 enol is shown in figure 1.
As can be seen, δ 5.48(m,2H, CH ═ CH), δ 3.65(s,1H, OH), δ 3.50(m,2H, CH), δ 3.48 (m,2H, CH ═ CH), and the like2)，δ2.18(m,4H,CH2CH＝CHCH2)。
3. C22 enol is subjected to ring opening reaction with propylene oxide.
(1) The reaction formula is as follows:
(2) the synthesis process comprises the following steps:
111.8g of C22 enol and 2.0g of Mg/Al composite oxide (MAO, Mg/Al molar ratio 3:1) were weighed into a 1L reactor, which was sealed and replaced with nitrogen 3 times. Starting stirring, heating to 140 ℃, starting a vacuum pump to vacuumize, heating to 170 ℃, and stopping vacuumizing. Opening a feeding valve, sending 261.36g of propylene oxide in the storage tank into the reaction kettle by using nitrogen, controlling the reaction temperature to be 140-180 ℃, controlling the pressure to be less than 0.15MPa, and reacting for 5 hours. Cooling and discharging to obtain C22 enol polyoxypropylene (10) ether.
(3) Structural characterization:
the electrospray mass spectrum of C22 enol polyoxypropylene (10) ether is shown in FIG. 2. It can be seen from the figure that the molecular weight is normally distributed. The molecular weight distribution index of the product was 90.3%.
4. Ethoxylation reaction
(1) The reaction formula is as follows:
(2) the synthesis process comprises the following steps:
249g of C22 enol polyoxypropylene (10) ether and 1.5g of sodium methoxide were weighed out and put into a 1L reactor, which was sealed and then purged with nitrogen gas 3 times. Starting stirring, heating to 130 ℃, starting a vacuum pump to pump vacuum, heating to 160 ℃, and stopping vacuumizing. The feeding valve is opened, 133g of ethylene oxide in the storage tank is sent into the reaction kettle by nitrogen, the reaction temperature is controlled to be 130-170 ℃, the pressure is controlled to be less than 0.15MPa, and the reaction is carried out for 6 hours. Cooling, discharging, and obtaining the product which mainly comprises C22 enol polyoxypropylene (10) polyoxyethylene (10) block copolymer.
(3) Structural characterization:
the electrospray mass spectrum of the C22 enol polyoxypropylene (10) polyoxyethylene (10) block copolymer product obtained in this example is shown in FIG. 3. It can be seen from the figure that the molecular weight is normally distributed and the main component is C22 enol polyoxypropylene (10) polyoxyethylene (10) block copolymer.
Application example 1: application of C22 enol polyoxypropylene (10) polyoxyethylene (10) block copolymer in emulsification and viscosity reduction
Wangshi tiger et al examined the effect of alkylphenol polyoxyethylene-polyoxypropylene ether on emulsification and viscosity reduction of thick oil (oil field chemistry, 2003,20:7-10), and particularly for hypersalinity oil reservoirs, found that the carbon number of R is 9, the addition number of EO accounts for 50-95% of the addition number of EO and PO, and the emulsification effect is optimal when the HLB value is more than 13. However, alkylphenol ethoxylates have estrogen-like action and can harm the normal hormone-secreting chemicals of the human body, so that the use of products containing NP and OP has been totally banned. In addition, for high-coagulation crude oil, the main reason for causing crude oil coagulation is that the paraffin wax with high alkane carbon number in the crude oil is high, so from the similar compatibility principle, for the viscosity reduction and the coagulation reduction of the high-coagulation crude oil, an emulsifier containing long-chain alkane is an ideal choice.
TABLE 2 Gilin high pour point and high viscosity crude oil Properties
The emulsification and dispersion of the high-coagulation high-viscosity crude oil are beneficial to improving the fluidity ratio, expanding the micro-wave and the volume and improving the recovery ratio.
The viscosity reducer adopted in the application example 1 is a block copolymer of nonylphenol polyoxyethylene (10) ether (purchased by reagent companies) and C22 enol polyoxypropylene (10) polyoxyethylene (10), and the water diversion rate change conditions and the viscosity of different viscosity reducers and the residual high-viscosity crude oil of Jilin are respectively measured under the conditions that the oil-water ratio is 1:1 and the rotating speed is 10000 revolutions per minute. Experimental results research shows that the viscosity reduction rate of the C22 enol polyoxypropylene (10) polyoxyethylene (10) block copolymer is more than 95%, the viscosity reduction rate of the nonylphenol polyoxyethylene (10) ether is 90%, and the water separation rate of the enol polyoxypropylene (10) block copolymer is lower than that of the nonylphenol polyoxyethylene (10) ether. The synthesized C22 enol polyoxypropylene (10) polyoxyethylene (10) block copolymer has excellent emulsifying capacity and stability.
Application example 2: emulsion oil displacement experiment of C22 enol polyoxypropylene (10) polyoxyethylene (10) block copolymer
1. Specification of materials
The Bailey core oil displacement experiment is carried out according to the oil and gas industry standard SY/T6424-2000 of the people's republic of China. The experimental oil is Jilin raffinate dehydrated crude oil with the viscosity of 64.4 mPa.s; the experimental water is used as the rest simulation injection water.
2. Experimental procedure
The slug is designed as: water flooding +0.5PV emulsifier + post-water flooding.
When the water content is 100 percent, 0.5 times of pore volume of 0.3 percent aqueous solution of C22 enol polyoxypropylene (10) polyoxyethylene (10) block copolymer is injected, and the water flooding is carried out again until the water content is 100 percent.
3. Results of the experiment
TABLE 3 Bailey core parameters
Table 4 results of the oil displacement by emulsion flooding
Through a Berea core experiment, an obvious oil-in-water emulsion is seen at the extraction end, the single system improves the recovery rate by 21.7 percent on the basis of 43.2 percent of water flooding, and the performance is excellent.
Application example 3: low-permeability beret core experiment in polymer flooding system added with C22 enol polyoxypropylene (10) polyoxyethylene (10) block copolymer
1. Specification of materials
The Bailey core oil displacement experiment is carried out according to the oil and gas industry standard SY/T6424-2000 of the people's republic of China. The experimental oil is Daqing simulated oil with the viscosity of 9.0 mPa.s; the experimental water is the sewage produced in Daqing.
The polymer was 2000 ten thousand molecular weight polyacrylamide.
2. Experimental procedure
The slug is designed as: water flooding +0.5PV polymer slug + post-water flooding.
(1) When the water content is 100 percent, 2000 ten thousand molecular weight polymer aqueous solution with the concentration of 1850ppm and 0.5 times of pore volume is injected, and the water content is driven to 100 percent after that.
(2) When the water content is 100%, 2000 ten thousand molecular weight polymer with a concentration of 1850ppm in 0.5 times the pore volume and 900ppm of C22 enol polyoxypropylene (10) polyoxyethylene (10) block copolymer aqueous solution are injected, and the water content is 100% after water flooding.
3. Results of the experiment
TABLE 5 Polymer flooding Experimental results
The Berea core experiment shows that under the same concentration condition, the apparent viscosity of a C22 enol polyoxypropylene (10) polyoxyethylene (10) block copolymer and a polyacrylamide composite system with the molecular weight of 2000 ten thousand is higher than that of single polyacrylamide, and the main reason is that the synthesized copolymer and polyacrylamide have interaction between molecules, so that the rigidity of a molecular chain is increased. Within certain limits, the increased viscosity of the displacement system increases the magnitude of the enhanced oil recovery. Therefore, the development of the copolymer has important significance for the development of low-permeability oil fields.
Finally, the description is as follows: although the present invention has been described in detail with reference to the above embodiments, it should be understood by those skilled in the art that: modifications and equivalents may be made thereto without departing from the spirit and scope of the invention and it is intended to cover any modifications or equivalents as may fall within the scope of the invention.
Claims (8)
1. An unsaturated double bond-containing C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer, which has a structure shown in a general formula I:
wherein p is a positive integer selected from 5 to 50;
q is a positive integer selected from 5 to 50;
and the C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer containing unsaturated double bonds is prepared by the method comprising the following steps:
preparation of C22 enol: mixing erucic acid ethyl ester and anhydrous acetic acid, and reacting under the action of metal sodium to obtain C22 enol;
ring opening reaction: c22 enol and epoxypropane carry out ring-opening reaction under the action of a catalyst to obtain C22 enol polyoxypropylene ether;
ethoxylation reaction: c22 enol polyoxypropylene ether and epoxy ethane are subject to ethoxylation reaction under the action of catalyst to obtain C22 enol polyoxypropylene polyoxyethylene block copolymer.
2. The unsaturated double bond-containing C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer according to claim 1, wherein p is 10 and q is 10.
3. A method for preparing the unsaturated double bond-containing C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer of claim 1 or 2, comprising the steps of:
preparation of C22 enol: mixing erucic acid ethyl ester and anhydrous acetic acid, and reacting under the action of metal sodium to obtain C22 enol;
ring opening reaction: c22 enol and epoxypropane carry out ring-opening reaction under the action of a catalyst to obtain C22 enol polyoxypropylene ether;
ethoxylation reaction: c22 enol polyoxypropylene ether and epoxy ethane are subject to ethoxylation reaction under the action of catalyst to obtain C22 enol polyoxypropylene polyoxyethylene block copolymer.
4. The process of claim 3, wherein in the ring opening reaction of a C22 enol with propylene oxide, the molar ratio of C22 enol to propylene oxide is 1: 5 to 50.
5. The method of claim 3, wherein in the ethoxylation of C22 enol polyoxypropylene ether with ethylene oxide, the molar ratio of C22 enol polyoxypropylene ether to ethylene oxide is 1: 10 to 50.
6. Use of the unsaturated double bond-containing C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer as claimed in claim 1 or 2 in the emulsification and viscosity reduction of thick oil.
7. Use of the unsaturated double bond-containing C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer as claimed in claim 1 or 2 for pour point depressing of highly waxy crude oil.
8. Use of the unsaturated double bond-containing C22 fatty alcohol polyoxypropylene polyoxyethylene block copolymer as claimed in claim 1 or 2 in chemical flooding for tertiary oil recovery.
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