CN116023667A - Demulsifier and preparation method and application thereof - Google Patents
Demulsifier and preparation method and application thereof Download PDFInfo
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- CN116023667A CN116023667A CN202211690885.3A CN202211690885A CN116023667A CN 116023667 A CN116023667 A CN 116023667A CN 202211690885 A CN202211690885 A CN 202211690885A CN 116023667 A CN116023667 A CN 116023667A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000006260 foam Substances 0.000 claims abstract description 18
- -1 phenolic amine Chemical class 0.000 claims description 59
- 229920005989 resin Polymers 0.000 claims description 58
- 239000011347 resin Substances 0.000 claims description 58
- 238000006243 chemical reaction Methods 0.000 claims description 39
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 36
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 36
- 229920000570 polyether Polymers 0.000 claims description 36
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 32
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 21
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 14
- 238000005917 acylation reaction Methods 0.000 claims description 14
- 229920000768 polyamine Polymers 0.000 claims description 14
- 238000005886 esterification reaction Methods 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 13
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- 239000003999 initiator Substances 0.000 claims description 12
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000007334 copolymerization reaction Methods 0.000 claims description 9
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- 238000006068 polycondensation reaction Methods 0.000 claims description 8
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 4
- MTLWTRLYHAQCAM-UHFFFAOYSA-N 2-[(1-cyano-2-methylpropyl)diazenyl]-3-methylbutanenitrile Chemical compound CC(C)C(C#N)N=NC(C#N)C(C)C MTLWTRLYHAQCAM-UHFFFAOYSA-N 0.000 claims description 3
- 238000007046 ethoxylation reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000012530 fluid Substances 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 abstract description 22
- 230000018044 dehydration Effects 0.000 abstract description 20
- 239000007788 liquid Substances 0.000 abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 5
- 125000001302 tertiary amino group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 238000007254 oxidation reaction Methods 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000010779 crude oil Substances 0.000 description 6
- 230000002194 synthesizing effect Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000007599 discharging Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000004088 foaming agent Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000011056 performance test Methods 0.000 description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
- 229960001124 trientine Drugs 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011549 displacement method Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- RCHKEJKUUXXBSM-UHFFFAOYSA-N n-benzyl-2-(3-formylindol-1-yl)acetamide Chemical compound C12=CC=CC=C2C(C=O)=CN1CC(=O)NCC1=CC=CC=C1 RCHKEJKUUXXBSM-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of petrochemical industry, and provides a demulsifier, a preparation method and application thereof. The demulsifier structure provided by the invention contains a large amount of tertiary amine groups, so that the strength of the oil-water interfacial film can be effectively reduced, and the demulsifier structure has a good dehydration effect at low temperature for foam flooding produced liquid and is high in dehydration speed. The preparation method of the demulsifier provided by the invention has simple steps and is easy to operate.
Description
Technical Field
The invention relates to the technical field of petrochemical industry, in particular to a demulsifier and a preparation method and application thereof.
Background
The foam flooding is an oil displacement method using foam as oil displacement agent, and the foam is composed of water, gas and foaming agent, and is a technology for improving recovery ratio widely used in the current oil field. The foaming agent in the foam flooding system is a strong surfactant, and can interact with active components of crude oil under the oil reservoir condition, so that the oil-water interfacial tension can be reduced, and the foam flooding system has strong oil washing capability. However, the existence of the foaming agent can also enhance the interfacial film strength of the produced liquid, so that the degree of oil-water emulsification is enhanced, and the treatment difficulty of the foam flooding produced liquid is increased.
At present, conventional demulsifiers such as TA1031 (phenol-amine aldehyde resin block polyether), BPE2040 (block polyether with alcohols as an initiator) and the like are used for treating foam flooding produced liquid, and the conventional demulsifiers have a good demulsification effect on interfacial films formed by active substances such as acidic active components of crude oil and asphaltenes as main film forming substances; however, the foam flooding produced emulsion interfacial film formed by the interaction of the foaming agent and the crude oil active components has stable structure, and the conventional demulsifier has poor adaptability, and is characterized by high demulsification temperature (above 60 ℃), low dehydration speed and even ineffective demulsification.
Disclosure of Invention
In view of the above, the invention provides a demulsifier and a preparation method and application thereof. The demulsifier provided by the invention can effectively reduce the strength of the oil-water interfacial film, has good dehydration effect on foam flooding produced liquid at low temperature, and has high dehydration speed.
In order to achieve the above object, the present invention provides the following technical solutions:
a demulsifier having a structure according to formula I:
in formula I: n=0 to 7,s =1 to 10, p=1 to 6;
the structure of M in the formula I is shown as the formula II:
in formula II: x=5 to 20, y=5 to 30.
The invention also provides a preparation method of the demulsifier, which comprises the following steps:
mixing N, N-dimethyl-1, 3-propylene diamine, maleic anhydride and an organic solvent for acylation reaction to obtain a first intermediate; the structure of the first intermediate is shown in a formula III;
mixing the first intermediate, acrylic acid and a free radical initiator to carry out copolymerization reaction to reach a second intermediate; the structural formula of the second intermediate is shown as a formula IV;
mixing the second intermediate with phenolic amine resin polyether for esterification reaction to obtain a demulsifier with a structure shown in a formula I; the structure of the phenolic amine resin polyether is shown as a formula V;
preferably, the molar ratio of the N, N-dimethyl-1, 3-propylene diamine to the maleic anhydride is 1:1-4; the temperature of the acylation reaction is 50-100 ℃ and the reaction time is 1-10 h.
Preferably, the free radical initiator comprises one or more of benzoyl peroxide, azobisisobutyronitrile, azobisisoheptonitrile and azobisisovaleronitrile; the weight of the free radical initiator is 1-20 per mill of the total weight of the first intermediate and the acrylic acid.
Preferably, the molar ratio of the first intermediate to the acrylic acid is 1:1-10; the temperature of the copolymerization reaction is 70-160 ℃ and the time is 1-12 h.
Preferably, the molar ratio of the second intermediate to the phenolic amine resin polyether is 1-14:1; the temperature of the esterification reaction is 90-160 ℃ and the time is 1-12 h.
Preferably, the preparation method of the phenolic amine resin polyether comprises the following steps:
mixing polyamine, bisphenol A and formaldehyde for polycondensation reaction to obtain phenolic amine resin; the structure of the polyamine is shown in a formula VI;
and (3) performing a propoxylation reaction on the phenolic amine resin and propylene oxide under an alkaline catalyst, and performing an ethoxylation reaction on the obtained reactant and ethylene oxide to obtain phenolic amine resin polyether.
Preferably, the mol ratio of bisphenol A, polyamine and formaldehyde is 1:1-4:1-4; the mol ratio of bisphenol A to propylene oxide is 1:10-60; the mol ratio of bisphenol A to ethylene oxide is 1:10-40.
Preferably, the alkaline catalyst is one of sodium methoxide, sodium hydroxide and potassium hydroxide; the weight of the alkaline catalyst is 1-20 per mill of the weight of the phenolic amine resin.
The invention also provides an application of the demulsifier prepared by the scheme or the preparation method of the scheme in foam flooding produced liquid.
The invention provides a demulsifier, the structural formula of which is shown as formula I. The demulsifier structure provided by the invention contains a large amount of tertiary amine groups, so that the strength of the oil-water interfacial film can be effectively reduced, and the demulsifier structure has a good dehydration effect at low temperature for foam flooding produced liquid and is high in dehydration speed.
The invention also provides a preparation method of the demulsifier, which is simple in steps and easy to operate.
Detailed Description
The invention provides a demulsifier, which has a structure shown in a formula I:
in formula I: n=0 to 7,s =1 to 10, p=1 to 6;
the structure of M in the formula I is shown as the formula II:
in formula II: x=5 to 20, y=5 to 30, and the wavy line in formula II indicates a broken bond, which is a bond with formula I.
In the present invention, the n is preferably 0, 1, 2, 3, 4, 5, 6 or 7; s is preferably from 2 to 8, more preferably from 3 to 7, in particular 2, 4, 5, 6, 9 or 10, and p is preferably 1, 2, 3, 4, 5 or 6.
The invention also provides a preparation method of the demulsifier, which comprises the following steps:
mixing N, N-dimethyl-1, 3-propylene diamine, maleic anhydride and an organic solvent for acylation reaction to obtain a first intermediate; the structure of the first intermediate is shown in a formula III;
mixing the first intermediate, acrylic acid and a free radical initiator to carry out copolymerization reaction to reach a second intermediate; the structural formula of the second intermediate is shown as a formula IV;
mixing the second intermediate with phenolic amine resin polyether for esterification reaction to obtain a demulsifier with a structure shown in a formula I; the structure of the phenolic amine resin polyether is shown as a formula V;
the value ranges of x and y in the formula IV are consistent with those in the formula II, and the value ranges of n, p and s in the formula V are consistent with those in the formula I.
The invention mixes N, N-dimethyl-1, 3-propylene diamine, maleic anhydride and organic solvent for acylation reaction to obtain a first intermediate. In the present invention, the molar ratio of the N, N-dimethyl-1, 3-propanediamine to the maleic anhydride is preferably 1:1 to 4, more preferably 1:1 to 2; the organic solvent preferably comprises one or more of toluene, xylene, no. 90 solvent oil, and No. 120 solvent oil; the invention has no special requirement on the dosage of the organic solvent, and can lead the acylation reaction to be carried out smoothly.
In the present invention, the temperature of the acylation reaction is preferably 50 to 100 ℃, more preferably 60 to 90 ℃, and the time of the acylation reaction is preferably 1 to 10 hours, more preferably 2 to 6 hours. In the specific embodiment of the invention, the N, N-dimethyl-1, 3-propylene diamine and the organic solvent are preferably added into a reaction kettle, then the temperature is raised to the temperature of the acylation reaction, and then maleic anhydride is added in batches, wherein the maleic anhydride is preferably added in 1h, and the acylation reaction is carried out after the addition is completed; the time of the acylation reaction is counted from the completion of the addition of maleic anhydride.
In the present invention, the acylation reaction has the following reaction formula:
and after the acylation reaction is finished, cooling to below 50 ℃, discharging, and directly carrying out subsequent reaction on the obtained product liquid.
After the first intermediate is obtained, the first intermediate, acrylic acid and a free radical initiator are mixed for copolymerization reaction to reach the second intermediate. In the present invention, the radical initiator preferably includes one or more of benzoyl peroxide, azobisisobutyronitrile, azobisisoheptonitrile and azobisisovaleronitrile; the weight of the free radical initiator is preferably 1 to 20 per mill, more preferably 3 to 15 per mill of the total weight of the first intermediate and the acrylic acid; the molar ratio of the first intermediate to the acrylic acid is preferably 1:1-10, more preferably 1:1-5; the temperature of the copolymerization reaction is preferably 70 to 160 ℃, more preferably 70 to 120 ℃, and the time is preferably 1 to 12 hours, more preferably 3 to 9 hours.
In the specific embodiment of the invention, the first intermediate, the free radical initiator and the acrylic acid are preferably added into a reaction kettle, vacuumized, deoxygenated by nitrogen for 3 times, and then heated to the temperature of copolymerization reaction for reaction; and after the reaction is finished, cooling to below 80 ℃, discharging, and directly carrying out subsequent reaction on the obtained product liquid.
In the present invention, the copolymerization reaction has the following reaction formula:
after the second intermediate is obtained, the demulsifier with the structure shown in the formula I is obtained by mixing the second intermediate with the phenolic amine resin polyether for esterification reaction.
First, a method for producing a phenol-formaldehyde amine resin polyether (referred to as DPA) will be described.
In the present invention, the preparation method of the phenolic amine resin polyether preferably comprises the following steps:
mixing polyamine, bisphenol A and formaldehyde for polycondensation reaction to obtain phenolic amine resin; the structure of the polyamine is shown in a formula VI;
and (3) performing propyl oxidation reaction on the phenolic amine resin and propylene oxide under an alkaline catalyst, and performing ethyl oxidation reaction on the obtained reactant and ethylene oxide to obtain phenolic amine resin polyether.
The invention mixes polyamine, bisphenol A and formaldehyde to carry out polycondensation reaction to obtain phenolic amine resin (DP); the structure of the polyamine is shown in a formula VI. In the present invention, the polyamine is preferably ethylenediamine or polyethylene polyamine, which preferably includes one or more of diethylenetriamine, triethylenetetramine and tetraethylenepentamine; the mol ratio of bisphenol A, polyamine and formaldehyde is preferably 1:1-4:1-4, more preferably 1:2-3:2-3; the temperature of the polycondensation reaction is preferably 30-80 ℃; the formaldehyde is preferably added in a dropwise manner, the dropwise time is preferably 1-12 h, more preferably 1-8 h, and the heat preservation reaction is continued for 1-12 h after the dropwise is finished. In the specific embodiment of the invention, the polyamine and bisphenol A are preferably added into a reaction kettle, then the temperature is raised to the temperature of polycondensation reaction, and formaldehyde is added dropwise.
After the polycondensation reaction is finished, the invention preferably carries out vacuum dehydration on the obtained product feed liquid to obtain phenolic amine resin; the vacuum degree of the vacuum dehydration is preferably 0.085-0.095 MPa, the temperature of the vacuum dehydration is preferably 100-110 ℃, and the dehydration time is preferably 3h.
In the present invention, the polycondensation reaction has the following reaction formula:
after obtaining the phenolic amine resin, the phenolic amine resin and propylene oxide are subjected to propyl oxidation reaction under the condition of an alkaline catalyst, and the obtained reactant and ethylene oxide are subjected to ethyl oxidation reaction, so that the phenolic amine resin polyether (DPA) is obtained. In the present invention, the molar ratio of bisphenol A to propylene oxide is preferably 1:10 to 60, more preferably 1:20 to 50; the alkaline catalyst is preferably one of sodium methoxide, sodium hydroxide and potassium hydroxide; the weight of the alkaline catalyst is preferably 1-20% of the weight of the phenolic amine resin, and more preferably 2-15%.
In the present invention, the temperature of the propyl oxidation reaction is preferably 120 to 150 ℃, more preferably 130 to 140 ℃; in the specific embodiment of the invention, the phenolic amine resin, the catalyst and the alkaline catalyst are preferably mixed firstly, then dehydrated for 30min at 100-110 ℃, then heated to the temperature of propyl oxidation reaction, and then propylene oxide is introduced into the system; in the specific embodiment of the invention, the reaction is preferably continued for 45min after the propylene oxide is completely fed, namely the reaction is considered to be complete, or the pressure in the kettle is considered to be complete before the pressure is reduced to the pressure before the propylene oxide is fed.
After the propylene oxide is completely introduced and reacted, ethylene oxide is preferably continuously introduced into the system to carry out ethyl oxidation reaction, wherein the mol ratio of bisphenol A to ethylene oxide is preferably 1:10-40, more preferably 1:20-30; the temperature of the ethyl oxidation reaction is preferably 120-150 ℃, more preferably 130-140 ℃; the criterion for reaction completion was identical to the above protocol.
And after the ethylene oxide is reacted completely, cooling to below 80 ℃ and discharging.
In the present invention, the reaction formula of the phenolic amine resin, propylene oxide and ethylene oxide is as follows:
after obtaining the phenolic amine resin polyether, the invention mixes the second intermediate and the phenolic amine resin polyether for esterification reaction to obtain the demulsifier with the structure shown in the formula I. In the present invention, the molar ratio of the second intermediate to the phenolic amine resin polyether is preferably 1 to 14:1, more preferably 2 to 10:1; the esterification reaction is preferably carried out in an organic solvent, which preferably comprises one or more of toluene, xylene, no. 90 solvent oil, no. 120 solvent oil.
In the present invention, the temperature of the esterification reaction is preferably 90 to 160 ℃, more preferably 100 to 140 ℃, and in the specific embodiment of the present invention, the esterification reaction is preferably performed under reflux conditions; the time of the esterification reaction is preferably 1 to 12 hours, more preferably 4 to 10 hours.
In the present invention, the esterification reaction has the following reaction formula:
in the above reaction formula, the connection structure at the wavy line is as follows:
after the esterification reaction is completed, the product feed liquid is the demulsifier, the content of the effective components of the demulsifier is 75-90%, and the demulsifier can be diluted into corresponding solid content by adding a solvent according to the requirements of customers.
The invention also provides an application of the demulsifier prepared by the scheme or the preparation method of the scheme in foam flooding produced liquid; the invention is not particularly limited to the particular method of operation of the application described, as long as it is known to those skilled in the art. In the specific embodiment of the invention, the addition amount of the demulsifier in the foam flooding produced liquid is preferably 60-150 ppm; the temperature at which the demulsifier is applied is preferably from 35 to 55 ℃.
The following description of the embodiments of the present invention will clearly and fully describe the technical solutions of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
First intermediate synthesis: 102.2Kg of N, N-dimethyl-1, 3-propylene diamine and 301Kg of dimethylbenzene are put into a reaction kettle, the temperature is raised to 60-70 ℃, 98.1Kg of maleic anhydride is added in batches, the reaction is continued for 3-4 hours after 1 hour batch addition, 501Kg of a first intermediate is obtained, the temperature is lowered to below 50 ℃, and the materials are discharged for standby;
synthesis of the second intermediate: 500Kg of intermediate A, 1.5Kg of Benzoyl Peroxide (BPO) and 72Kg of acrylic acid are put into a reaction kettle, vacuumized, deoxygenated by nitrogen replacement for three times, heated to 70-80 ℃ and reacted for 6-8 hours to obtain a second intermediate, cooled to below 80 ℃ and discharged for standby;
phenolic amine resin (DP) synthesis: 206.3Kg of diethylenetriamine and 114.2Kg of bisphenol A are put into a reaction kettle, the temperature is raised to 40-50 ℃, 164.6Kg of formaldehyde (36.5%) solution is dripped, the dripping is completed, the temperature is kept for 3 hours, dehydration is carried out for 3 hours under the conditions of vacuum degree of 0.085-0.095 Mpa and 100-110 ℃ to obtain 344.6KG of phenolic amine resin (DP), and the temperature is reduced to 80 ℃ for standby.
Phenolic amine resin polyether (DPA) synthesis: 344Kg of phenolic amine resin (DP) is put into an autoclave, 1.0Kg of potassium hydroxide is added, dehydration is carried out for half an hour at 100-110 ℃, the temperature is raised to 130-150 ℃, 580Kg of propylene oxide is introduced, the reaction is complete, 330Kg of ethylene oxide is introduced, the reaction is complete, 1254Kg of phenolic amine resin polyether (DPA) is obtained, the temperature is reduced to below 80 ℃, and the material is discharged for standby.
And synthesizing a demulsifier, namely adding 627Kg of phenolic amine resin polyether (DPA), 2000Kg of second intermediate and 650Kg of dimethylbenzene into a reaction kettle, heating to 110-120 ℃, and carrying out constant-temperature reflux reaction for 8 hours to obtain the demulsifier.
Example 2
First intermediate synthesis: as in example 1;
and (3) synthesizing a second intermediate: as in example 1;
phenolic amine resin (DP) synthesis: as in example 1;
phenolic amine resin polyether (DPA) synthesis: 344Kg of phenolic amine resin (DP) is put into an autoclave, 1.0Kg of potassium hydroxide is added, dehydration is carried out for half an hour at 100-110 ℃, the temperature is raised to 130-150 ℃, 870Kg of propylene oxide is introduced, the reaction is complete, 440Kg of ethylene oxide is introduced, the reaction is complete, 1654Kg of phenolic amine resin polyether (DPA) is obtained, the temperature is reduced to below 80 ℃, and the material is discharged for standby.
And (3) synthesizing a demulsifier, namely putting 827Kg of phenolic amine resin polyether (DPA), 2000Kg of second intermediate and 700Kg of dimethylbenzene into a reaction kettle, heating to 110-120 ℃, and carrying out constant-temperature reflux reaction for 8 hours to obtain the demulsifier.
Example 3
First intermediate synthesis: as in example 1;
and (3) synthesizing a second intermediate: as in example 1;
phenolic amine resin (DP) synthesis: 292.5Kg of triethylene tetramine and 114.2Kg of bisphenol A are put into a reaction kettle, the temperature is raised to 40-50 ℃, 164.6Kg of formaldehyde (36.5%) solution is dripped, the dripping is completed, the temperature is kept for 3 hours, dehydration is carried out for 3 hours at the vacuum degree of 0.085-0.095 Mpa and the temperature of 100-110 ℃ to obtain 370.5Kg of phenolic amine resin (DP), and the temperature is reduced to 80 ℃ for standby.
Phenolic amine resin polyether (DPA) synthesis: 370Kg of phenolic amine resin (DP) is put into an autoclave, 1.48Kg of potassium hydroxide is added, dehydration is carried out for half an hour at 100-110 ℃, the temperature is raised to 130-150 ℃, 580Kg of propylene oxide is introduced, the reaction is complete, 330Kg of ethylene oxide is introduced, the reaction is complete, 1280.8Kg of phenolic amine resin polyether (DPA) is obtained, the temperature is reduced to below 80 ℃, and the material is discharged for standby.
And (3) demulsifier synthesis: 640Kg of phenolic amine resin polyether (DPA), 2000Kg of second intermediate and 700Kg of dimethylbenzene are put into a reaction kettle, and are heated to 110-120 ℃ for reflux reaction at constant temperature for about 8 hours, so as to obtain the demulsifier.
Example 4
First intermediate synthesis: as in example 1;
and (3) synthesizing a second intermediate: as in example 1;
phenolic amine resin (DP) synthesis: 388.68Kg of tetraethylenepentamine and 114.2Kg of bisphenol A are put into a reaction kettle, the temperature is raised to 40-50 ℃, 164.6Kg of formaldehyde (36.5%) solution is dripped, the dripping is completed, the temperature is kept for 3 hours, dehydration is carried out for 3 hours at the vacuum degree of 0.085-0.095 Mpa and the temperature of 100-110 ℃ to obtain 526.5Kg of phenolic amine resin (DP), and the temperature is reduced to 80 ℃ for standby.
Phenolic amine resin polyether (DPA) synthesis: putting 526Kg of phenolic amine resin (DP) into an autoclave, adding 1.5Kg of potassium hydroxide, dehydrating for half an hour at 100-110 ℃, heating to 130-150 ℃, introducing 780Kg of propylene oxide, completely reacting, introducing 330Kg of ethylene oxide, completely reacting to obtain 1635.6Kg of phenolic amine resin polyether (DPA), cooling to below 80 ℃, discharging for standby
And (3) synthesizing a demulsifier, namely adding 409Kg of phenolic amine resin polyether (DPA), 1728Kg of second intermediate and 425Kg of dimethylbenzene into a reaction kettle, heating to 110-120 ℃, and carrying out constant-temperature reflux reaction for about 8 hours to obtain the demulsifier.
Test case
And (3) performing demulsification experiments on mixed crude oil of a certain national combined station (containing foam flooding produced liquid) by adopting a chemical dehydration method:
the determination method and the reagent of the chemical dehydration method refer to SY/T5281-2000 crude oil demulsifier service performance detection method (bottle test method) of the oil and gas industry standard of the people's republic of China;
the physical parameters of crude oil are as follows:
oil sample density (density bottle method): 0.9156g/mL (20 ℃ C.)
Oil sample water content (distillation): 35.0%
The demulsifier performance test data are shown in tables 1-2.
Table demulsification Performance test data at 150℃
In table 1: the site sample was TA1031 (phenol-amine-aldehyde resin block polyether) modified product, code 2219.
Table 240 ℃ demulsification Performance test data
In table 2: the site sample was TA1031 (phenol-amine-aldehyde resin block polyether) modified product, code 2219.
According to the data in tables 1-2, the demulsifier prepared in examples 1-4 is adopted to demulsifi the foam flooding produced liquid at 40 ℃ or 50 ℃, and compared with a field sample, the demulsifier has larger dehydration amount and water yield, so that the demulsifier can effectively reduce the strength of an oil-water interfacial film, has good dehydration effect on the foam flooding produced liquid at low temperature, and has high dehydration speed.
The foregoing is merely a preferred embodiment of the present invention and it should be noted that modifications and adaptations to those skilled in the art may be made without departing from the principles of the present invention, which are intended to be comprehended within the scope of the present invention.
Claims (10)
1. A demulsifier, characterized by having a structure according to formula I:
in formula I: n=0 to 7,s =1 to 10, p=1 to 6;
the structure of M in the formula I is shown as the formula II:
in formula II: x=5 to 20, y=5 to 30.
2. The method for preparing the demulsifier of claim 1, comprising the steps of:
mixing N, N-dimethyl-1, 3-propylene diamine, maleic anhydride and an organic solvent for acylation reaction to obtain a first intermediate; the structure of the first intermediate is shown in a formula III;
mixing the first intermediate, acrylic acid and a free radical initiator to carry out copolymerization reaction to reach a second intermediate; the structural formula of the second intermediate is shown as a formula IV;
mixing the second intermediate with phenolic amine resin polyether for esterification reaction to obtain a demulsifier with a structure shown in a formula I; the structure of the phenolic amine resin polyether is shown as a formula V;
3. the method according to claim 2, wherein the molar ratio of N, N-dimethyl-1, 3-propanediamine to maleic anhydride is 1:1-4; the temperature of the acylation reaction is 50-100 ℃ and the reaction time is 1-10 h.
4. The method of preparation of claim 2, wherein the free radical initiator comprises one or more of benzoyl peroxide, azobisisobutyronitrile, azobisisoheptonitrile, and azobisisovaleronitrile; the weight of the free radical initiator is 1-20 per mill of the total weight of the first intermediate and the acrylic acid.
5. The method of claim 2, wherein the molar ratio of the first intermediate to acrylic acid is 1:1 to 10; the temperature of the copolymerization reaction is 70-160 ℃ and the time is 1-12 h.
6. The method of claim 2, wherein the molar ratio of the second intermediate to the phenolic amine resin polyether is 1-14:1; the temperature of the esterification reaction is 90-160 ℃ and the time is 1-12 h.
7. The method of preparing as claimed in claim 2 or 6, wherein the method of preparing the phenolic amine resin polyether comprises the steps of:
mixing polyamine, bisphenol A and formaldehyde for polycondensation reaction to obtain phenolic amine resin; the structure of the polyamine is shown in a formula VI;
and (3) performing a propoxylation reaction on the phenolic amine resin and propylene oxide under an alkaline catalyst, and performing an ethoxylation reaction on the obtained reactant and ethylene oxide to obtain phenolic amine resin polyether.
8. The method according to claim 7, wherein the molar ratio of bisphenol a, polyamine and formaldehyde is 1:1 to 4:1 to 4; the mol ratio of bisphenol A to propylene oxide is 1:10-60; the mol ratio of bisphenol A to ethylene oxide is 1:10-40.
9. The method according to claim 7, wherein the basic catalyst is one of sodium methoxide, sodium hydroxide and potassium hydroxide; the weight of the alkaline catalyst is 1-20 per mill of the weight of the phenolic amine resin.
10. Use of the demulsifier of claim 1 or the demulsifier prepared by the method of any one of claims 2 to 9 in foam flooding production fluids.
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