CN116333712B - Crude oil pour point depressant and preparation method thereof - Google Patents
Crude oil pour point depressant and preparation method thereof Download PDFInfo
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- CN116333712B CN116333712B CN202310620583.7A CN202310620583A CN116333712B CN 116333712 B CN116333712 B CN 116333712B CN 202310620583 A CN202310620583 A CN 202310620583A CN 116333712 B CN116333712 B CN 116333712B
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- 239000010779 crude oil Substances 0.000 title claims abstract description 63
- 230000000994 depressogenic effect Effects 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 229920000642 polymer Polymers 0.000 claims abstract description 108
- 238000004132 cross linking Methods 0.000 claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
- 238000002156 mixing Methods 0.000 claims abstract description 7
- 238000005886 esterification reaction Methods 0.000 claims description 22
- -1 amino compound Chemical class 0.000 claims description 18
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 229920002732 Polyanhydride Polymers 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 8
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 7
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 7
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 7
- 238000007112 amidation reaction Methods 0.000 claims description 7
- 229930016911 cinnamic acid Natural products 0.000 claims description 7
- 235000013985 cinnamic acid Nutrition 0.000 claims description 7
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 6
- JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-UHFFFAOYSA-N 0.000 claims description 6
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 6
- 150000008064 anhydrides Chemical group 0.000 claims description 6
- RZIPTXDCNDIINL-UHFFFAOYSA-N cyclohexane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCCC1(C(O)=O)C(O)=O RZIPTXDCNDIINL-UHFFFAOYSA-N 0.000 claims description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 4
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 claims description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 4
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 14
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 abstract description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 8
- 239000013078 crystal Substances 0.000 abstract description 7
- 230000005496 eutectics Effects 0.000 abstract description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 14
- 239000001993 wax Substances 0.000 description 14
- 230000000694 effects Effects 0.000 description 11
- 239000005038 ethylene vinyl acetate Substances 0.000 description 10
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000005457 optimization Methods 0.000 description 9
- 230000000881 depressing effect Effects 0.000 description 8
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 7
- 238000001308 synthesis method Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000004711 α-olefin Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 150000002688 maleic acid derivatives Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920006029 tetra-polymer Polymers 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 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 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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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
- C09K8/58—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
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/60—Polyamides or polyester-amides
- C08G18/603—Polyamides
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention relates to the technical field of pour point depressant preparation, in particular to a crude oil pour point depressant and a preparation method thereof, wherein the crude oil pour point depressant comprises the following steps: a first step of preparing a first polymer, a second step of preparing a second polymer, and a third step of uniformly mixing the first polymer and the second polymer at 80 to 100 ℃ and using R n (CNO) 2 And (3) performing a crosslinking reaction to obtain the crude oil pour point depressant. According to the invention, after the first polymer and the second polymer are compounded, the polymer pour point depressant with multiple branched chains is obtained through crosslinking, and compared with a simple compound product, the product performance is greatly improved. The obtained crude oil pour point depressant has polar groups and nonpolar groups simultaneously, nonpolar groups such as high-carbon alcohol and the like and wax are subjected to eutectic, and polar groups such as urethane groups, urea groups, biuret groups and the like prevent wax crystals from growing up, so that the solidifying point of crude oil is reduced, and the purpose of improving the fluidity of the crude oil is achieved.
Description
Technical Field
The invention relates to the technical field of pour point depressant preparation, in particular to a crude oil pour point depressant and a preparation method thereof.
Background
Underground mineral reservoirs typically have relatively high temperatures. After the crude oil is produced to the surface, the produced crude oil is cooled more or less depending on the production temperature and the storage or transportation conditions.
Depending on their source, crude oils have varying proportions of waxes, which consist essentially of long chain normal paraffins. Depending on the type of crude oil, the proportion of these paraffins (paramffs) may generally be from 1% to 30% by weight of the crude oil. When the temperature falls below a certain level during cooling, the paraffins may crystallize generally in flake form. Precipitated paraffins significantly impair the flowability of the oil. The flake-form n-paraffin crystals may form a sort of card house structure that encapsulates the crude oil to stop the crude oil from flowing, even though the major portion is still liquid. The lowest temperature at which the oil sample remains just flowable during cooling is called the pour point ("yield point"). For measuring pour points, standardized test methods are used. Precipitated paraffins can clog filters, pumps, piping, and other facilities or deposit in tanks, thus requiring high levels of cleaning.
The deposit temperature of an oilfield is typically above room temperature, e.g., 40 ℃ to 100 ℃. Crude oil is extracted from such deposits while still warm and cooled naturally to room temperature more or less rapidly during or after extraction or to lower temperatures under corresponding climatic conditions. Crude oils may have pour points above room temperature such that such crude oils may solidify during or after production.
The Chinese patent publication No. CN108192004A discloses a tetrapolymer for crude oil pour point depressing, which comprises a structural unit obtained by the following compounds: maleic acid derivatives, polar vinyl compounds, higher alpha-olefins and ethylene. The molar ratio of the maleic acid derivative to the polar vinyl compound to the higher alpha-olefin to the ethylene is 1:1 to 5:1 to 2:10 to 30, the maleic acid derivative is obtained by reacting maleic anhydride with an amine compound, and the amine compound is mono-aliphatic amine with 8 to 50 carbon atoms, di-aliphatic amine with 8 to 50 carbon atoms or aliphatic alcohol amine with 8 to 50 carbon atoms. The polar vinyl compound is at least one selected from acrylic acid, acrylamide, styrene sulfonic acid, sodium styrene sulfonate, acrylic sulfonic acid and sodium acrylic sulfonate. The higher alpha-olefins are alpha-olefins having 8 to 50 carbon atoms. The crude oil pour point depressant containing the tetrapolymer has good pour point depressing and viscosity reducing effects on high-wax crude oil and high-viscosity crude oil. However, since pour point depressants have a very high selectivity for pour point depressing of crude oils, which are complex mixtures, this application has a great limitation on the use of pour point depressants.
Therefore, there is a need to develop a crude oil pour point depressant that not only has a synergistic effect, but also makes the wax crystallization inhibiting ability stronger.
Disclosure of Invention
The invention provides a crude oil pour point depressant and a preparation method thereof, which overcome the defects of the prior art, and the prepared crude oil pour point depressant is a macromolecule with a T-shaped structure and has various polar and nonpolar groups, so that complementary advantages are formed, and the pour point depressant performance is greatly enhanced.
One of the technical schemes of the invention is realized by the following measures: the preparation method of the crude oil pour point depressant comprises the following steps: a first step of preparing a first polymer, a second step of preparing a second polymer, a third step ofStep, the first polymer and the second polymer are uniformly mixed at the temperature of 80 ℃ to 100 ℃ and the required amount R is added dropwise 4 (CNO) 2 And (3) performing a crosslinking reaction for 1 to 2 hours to obtain the crude oil pour point depressant.
The following are further optimizations and/or improvements to one of the above-described inventive solutions:
r is as described above 4 (CNO) 2 Is a diisocyanate, including but not limited to toluene diisocyanate, and R 4 (CNO) 2 The added mass of (a) is 1 to 5% of the total dry mass of the first polymer and the second polymer.
The first polymer is prepared according to the following method: first, a desired amount of a polyanhydride compound or a polycarboxylic compound is reacted with R under the action of p-toluenesulfonic acid 2 Carrying out esterification reaction on OH to obtain a first polymer intermediate, wherein the esterification reaction temperature is 100-200 ℃, the esterification reaction time is 4-8 h, and in the esterification reaction, carboxyl groups in the polycarboxylic compound and R 2 The molar ratio of hydroxyl groups in the OH is 1.5 to 2.5:1 or anhydride groups to R in the polyanhydride compound 2 The molar ratio of hydroxyl groups in the OH is 1.5 to 2.5:2; and then, carrying out a crosslinking reaction on the first polymer intermediate and a required amount of amino compound to obtain a first polymer, wherein the crosslinking reaction temperature is 80-140 ℃, the crosslinking reaction time is 1-5 h, and the molar ratio of carboxyl groups in the first polymer intermediate to primary amino groups in the amino compound is 0.5-2:1.
In the first polymer preparation described above, the polyanhydride-based compound or the polycarboxylic compound is a compound including, but not limited to, pyromellitic dianhydride, biphenyl tetracarboxylic dianhydride, cyclohexane tetracarboxylic dianhydride, pyromellitic acid, biphenyl tetracarboxylic acid, and cyclohexane tetracarboxylic acid.
In the preparation of the first polymer, R 2 -OH is a compound or composition carrying a hydroxyl group, wherein R 2 Is more than one of C14 to C40 straight-chain alkyl, C14 to C40 isomerism alkyl and C2 to C40 alkyl group with benzene structure.
In the preparation of the first polymer, the amino compound is R 3 (NH 2 ) 2 Wherein R is 3 (NH 2 ) 2 Polyamines including, but not limited to, ethylenediamine, hexamethylenediamine, diethylenetriamine, tetraethylenepentamine, and triethylenediamine.
The second polymer is prepared according to the following method: firstly, mixing a required amount of EVA, cinnamic acid and maleic anhydride, adding an initiator di-tert-butyl peroxide, and performing polymerization reaction to obtain a second polymer intermediate I, wherein the polymerization reaction temperature is 100-200 ℃, and the molar ratio of EVA, cinnamic acid and maleic anhydride is 0.01-1:0.1-3:1-9; then, the second polymer intermediate-is reacted with the desired amount R under the influence of p-toluene sulfonic acid 2 Carrying out esterification reaction on OH to obtain a second polymer intermediate II, wherein the esterification reaction temperature is 100-200 ℃, and the molar ratio of carboxyl to higher alcohol in the esterification reaction is 1:0.25-0.95 or the molar ratio of anhydride to higher alcohol is 1:0.5-1.90; finally, the desired amount R is added to the second polymer intermediate II 5 R 3 NH 2 Amidation reaction is carried out to obtain a second polymer, wherein the amidation reaction temperature is 80 ℃ to 150 ℃.
R is as described above 5 R 3 NH 2 Wherein R is 5 Is a group containing a primary amino group or a hydroxyl group.
R is as described above 5 R 3 NH 2 Are organic amine compounds including, but not limited to, diethylenetriamine, tetraethylenepentamine, triethylenediamine, ethanolamine, and amino acids.
The second technical scheme of the invention is realized by the following measures: a crude oil pour point depressant obtained by a preparation method of the crude oil pour point depressant.
According to the invention, after the first polymer and the second polymer are compounded, the polymer pour point depressant with multiple branched chains is obtained through crosslinking, and compared with a simple compound product, the product performance is greatly improved. The obtained crude oil pour point depressant has polar groups and nonpolar groups simultaneously, nonpolar groups such as high-carbon alcohol and the like and wax are subjected to eutectic, and polar groups such as urethane groups, urea groups, biuret groups and the like prevent wax crystals from growing up, so that the solidifying point of crude oil is reduced, and the purpose of improving the fluidity of the crude oil is achieved.
Drawings
FIG. 1 is a chemical reaction equation for preparing a first polymer according to the present invention.
FIG. 2 is a chemical reaction equation for preparing a second polymer according to the present invention.
FIG. 3 is a chemical reaction equation for the crosslinking reaction of a first polymer and a second polymer according to the present invention.
Detailed Description
The present invention is not limited by the following examples, and specific embodiments can be determined according to the technical scheme and practical situations of the present invention. The various chemical reagents and chemicals mentioned in the present invention are all commonly known in the art unless specifically stated otherwise.
The invention is further described below with reference to examples:
example 1: the preparation method of the crude oil pour point depressant comprises the following steps: a first step of preparing a first polymer, a second step of preparing a second polymer, a third step of uniformly mixing the first polymer and the second polymer at 80 ℃ to 100 ℃ and dropwise adding a required amount R 4 (CNO) 2 And (3) performing a crosslinking reaction for 1 to 2 hours to obtain the crude oil pour point depressant.
According to the invention, the crude oil pour point depressant with the molecular weight of 7000 to 20000 is obtained by preparing a first polymer (exemplified by a derivative of tetracarboxylic dianhydride, the chemical reaction equation in the preparation process is shown in figure 1), preparing a second polymer (the chemical reaction equation in the preparation process is shown in figure 2) and then crosslinking with diisocyanate (the chemical reaction equation in the crosslinking reaction process is shown in figure 3). The molecular weight of the crude oil pour point depressant can be regulated and controlled, and the crude oil pour point depressant can be prepared into a macromolecule with a T-shaped structure, has various polar and nonpolar groups, forms complementary advantages, and greatly enhances the pour point depressant performance. In the chemical reaction formulas of fig. 1 to 3, n is 2 to 12, x is 2 to 10, y is 2 to 10, z is 2 to 15, and t is 2 to 8.
Example 2: as an optimization of the above embodiment, R 4 (CNO) 2 Is a diisocyanate, including but not limited to toluene diisocyanate, and R 4 (CNO) 2 Wherein R is 1 to 5% by mass of the total dry mass of the first polymer and the second polymer 4 Any group is possible.
Example 3: as an optimization of the above examples, the first polymer was prepared as follows: first, a desired amount of a polyanhydride compound or a polycarboxylic compound is reacted with R under the action of p-toluenesulfonic acid 2 Carrying out esterification reaction on OH to obtain a first polymer intermediate, wherein the esterification reaction temperature is 100-200 ℃, the esterification reaction time is 4-8 h, and in the esterification reaction, carboxyl groups in the polycarboxylic compound and R 2 The molar ratio of hydroxyl groups in the OH is 1.5 to 2.5:1 or anhydride groups to R in the polyanhydride compound 2 The molar ratio of hydroxyl groups in the OH is 1.5 to 2.5:2; and then, carrying out a crosslinking reaction on the first polymer intermediate and a required amount of amino compound to obtain a first polymer, wherein the crosslinking reaction temperature is 80-140 ℃, the crosslinking reaction time is 1-5 h, and the molar ratio of carboxyl groups in the first polymer intermediate to primary amino groups in the amino compound is 0.5-2:1.
Example 4: as an optimization of the above examples, in the first polymer preparation, the polyanhydride-based compound or the polycarboxy compound is a polymer comprising, but not limited to, pyromellitic dianhydride, biphenyl tetracarboxylic dianhydride, cyclohexane tetracarboxylic dianhydride, pyromellitic acid, biphenyl tetracarboxylic acid, and cyclohexane tetracarboxylic acid.
Example 5: as an optimization of the above examples, in the first polymer preparation, R 2 -OH is a compound or composition carrying a hydroxyl group, wherein R 2 Is more than one of C14 to C40 straight-chain alkyl, C14 to C40 isomerism alkyl and C2 to C40 alkyl group with benzene structure.
Example 6: as an optimization of the above examples, in the first polymer preparation, the amine-based compound may be R 3 (NH 2 ) 2 Wherein R is 3 (NH 2 ) 2 Polyamines including but not limited to ethylenediamine, hexamethylenediamine, diethylenetriamine, tetraethylenepentamine and triethylenediamine, R 3 Any group is possible.
Implementation of the embodimentsExample 7: as an optimization of the above examples, the second polymer was prepared as follows: firstly, mixing a required amount of EVA, cinnamic acid and maleic anhydride, adding an initiator di-tert-butyl peroxide, and performing polymerization reaction to obtain a second polymer intermediate I, wherein the polymerization reaction temperature is 100-200 ℃, and the molar ratio of EVA, cinnamic acid and maleic anhydride is 0.01-1:0.1-3:1-9; then, the second polymer intermediate-is reacted with the desired amount R under the influence of p-toluene sulfonic acid 2 Carrying out esterification reaction on OH to obtain a second polymer intermediate II, wherein the esterification reaction temperature is 100-200 ℃, and the molar ratio of carboxyl to higher alcohol in the esterification reaction is 1:0.25-0.95 or the molar ratio of anhydride to higher alcohol is 1:0.5-1.90; finally, the desired amount R is added to the second polymer intermediate II 5 R 3 NH 2 Amidation reaction is carried out to obtain a second polymer, wherein the amidation reaction temperature is 80 ℃ to 150 ℃.
Example 8: as an optimization of the above embodiment, R 5 R 3 NH 2 Wherein R is 5 Is a group containing a primary amino group or a hydroxyl group, R 3 Any group is possible.
The above examples demonstrate the beneficial effects of the present invention: the product structure of the invention not only comprises EVA structure, but also comprises a large amount of high-carbon alcohol and benzene structures, and simultaneously has polar groups such as urethane groups, urea groups, biuret groups and the like. The high-carbon alcohol, benzene structural groups and wax are subjected to eutectic, and polar groups such as urethane groups, urea groups and biuret groups prevent wax crystals from growing up, so that the solidifying point of crude oil is reduced, and the purpose of improving the fluidity of the crude oil is achieved.
Example 9: as an optimization of the above embodiment, R 5 R 3 NH 2 Are organic amine compounds including, but not limited to, diethylenetriamine, tetraethylenepentamine, triethylenediamine, ethanolamine, and amino acids.
Example 10: the crude oil pour point depressant is obtained by the preparation method of the crude oil pour point depressant.
Example 11: the crude oil pour point depressant is obtained according to the following method (the required amount of common solvents known in the art, such as dimethyl sulfoxide, dimethylbenzene and the like, are added according to the actual situation in the preparation process):
(1) Process for the preparation of a first polymer
218kg of pyromellitic anhydride is put into a dry and clean reaction kettle, 100kg of dimethyl sulfoxide is added, and the temperature is raised to 100 ℃ for stirring and dissolution;
135kg of stearyl alcohol, 242kg of cetyl alcohol, 135kg of isomeric stearyl alcohol, 7kg of p-toluenesulfonic acid and 50kg of dimethylbenzene are added;
esterification reaction is carried out for 6 hours at the temperature of 120 ℃ to 150 ℃ and the solvent is removed in vacuum, thus obtaining the first polymer intermediate.
Then adding 65kg of ethylenediamine, and controlling the temperature to be 80-110 ℃ for crosslinking reaction for 3 hours to obtain the first polymer.
(2) Process for preparing a second polymer
25kg of EVA (ethylene-vinyl acetate copolymer) is added, 148kg of cinnamic acid, 98kg of maleic anhydride and 250kg of dimethylbenzene are added, the temperature is raised and stirred, the temperature is controlled to 135 ℃, the di-tert-butyl peroxide is added twice, 3kg of EVA is added each time, and the temperature is controlled to be between 135 ℃ and 140 ℃ for 3 hours, so that a second polymer intermediate I is prepared.
Adding 135kg of stearyl alcohol, 242kg of cetyl alcohol and 135kg of isomeric stearyl alcohol, and carrying out esterification reaction for 6 hours at the temperature of 120-150 ℃ to obtain a second polymer intermediate II.
Adding 65kg of ethylenediamine, carrying out amidation reaction for 3h at the temperature of 80-110 ℃, and removing the solvent in vacuum to obtain a second polymer.
(3) Crosslinking reaction
The first polymer and the second polymer were all put into a kettle, 1000kg of xylene was added, and stirred uniformly, and the temperature was controlled at 80 ℃. Then toluene diisocyanate (1% of the total dry mass of the first polymer and the second polymer) is added dropwise, and the mixture is reacted for 2 hours at 80 ℃ to obtain the crude oil pour point depressant.
Example 12: the synthesis method and feeding of the first polymer and the synthesis method and feeding and crosslinking method of the second polymer were carried out as in example 11, and only the amount of the crosslinking agent was changed to obtain products with different crosslinking degrees, and the specific feeding is shown in table 1.
Example 13: the synthesis method and feeding and crosslinking methods of the first polymer were carried out in the same manner as in example 11, and only the addition ratio of the first polymer to the second polymer was changed to synthesize products with different crosslinking degrees, and the specific feeding is shown in Table 2.
Example 14: the synthesis method of the first polymer, the synthesis method of the second polymer and the crosslinking method are unchanged according to the operation in the example 11, only the type and the carbon chain length of the high-carbon alcohol in the reaction equation are changed, the molar ratio of the high-carbon alcohol to the carboxyl is unchanged, and products with different crosslinking degrees are obtained, and specific feeding is shown in the table 3.
The crude oil pour point depressants obtained in examples 12 to 14 above were tested using high wax crude oil as the test oil. The experimental oil has a congealing point of 21 ℃, a wax content of 21%, a colloid asphaltene content of 8-12%, a viscosity of 700-900 mPa.s, and a congealing point of the crude oil pour point depressant, which is tested according to SY/T5767-2016, and the results are shown in Table 4.
It can be seen from table 4 that both the first polymer and the second polymer have a certain pour point depressing effect, but the highest pour point depressing range for the target crude oil is only 5 ℃, and the first polymer and the second polymer have a certain synergistic effect after being compounded, but the synergistic effect capability is limited, and the rising of the temperature is only 2 ℃.
From the experimental results of the products numbered A1 to A6 in Table 4, it can be seen that the pour point depressing effect can be obviously improved after crosslinking, and the coordination effect can be further promoted. However, the degree of crosslinking must be controlled effectively, and excessive crosslinking weakens the coordinating effect, and the pour point depressing effect gradually becomes worse as the degree of crosslinking increases.
From the results of the product experiments of numbers B1 to B5 in table 4, it can be seen that adjusting the ratio of the polymer first monomer to the polymer second monomer within 25% of the addition mass of the second polymer has substantially no effect on the pour point depressing effect. However, if the second polymer addition mass adjustment range is adjusted to 50% or more of the addition mass, the effect is affected to some extent, and the larger the adjustment range is, the greater the degree of the effect is.
As can be seen from the experimental results of the products numbered C1 to C8 in Table 4, the combination of higher alcohols has a great influence on the performance of the formulation, and the introduction of behenyl alcohol has a great adverse effect on the performance of the formulation for the present crude oil, with the optimal formulation being the product numbered C4. However, compared with the product of the number A2, the product of the number C4 has obviously reduced solidifying point due to the introduction of the isostearyl alcohol, and the performance can be kept consistent with that of the product of the number C4. It is shown that the addition of the second polymer in the range of 25% replaces stearyl alcohol with isomeric stearyl alcohol, which does not affect the properties, but the addition of the second polymer in the range of more than 25% affects the properties, and the increase of the proportion of isomeric stearyl alcohol has a significant effect on the properties.
Therefore, the invention has the following beneficial effects:
1. the crude oil pour point depressant is a crosslinked product, and in the product structure, the pour point depressant not only comprises an EVA structure, but also comprises a large number of high-carbon alcohol and benzene structures, and simultaneously has polar groups such as urethane groups, urea groups, biuret groups and the like. The high-carbon alcohol, benzene structural groups and wax are subjected to eutectic, and polar groups such as urethane groups, urea groups and biuret groups prevent wax crystals from growing up, so that the solidifying point of crude oil is reduced, and the purpose of improving the fluidity of the crude oil is achieved;
2. the first polymer and the second polymer are crosslinked by the crude oil pour point depressant, so that the pour point depressant has more outstanding pour point depressant effect;
3. the urethane groups, the urea groups, the biuret groups, the high-carbon alcohol and the benzene structural groups in the crude oil pour point depressant are subjected to crosslinking reaction with the EVA structure, so that the coordination effect of the functional groups can be greatly improved, and the pour point depressant effect is better improved;
4. the crude oil pour point depressant solves the problem of limitation caused by pour point depressants with single composition by blending the carbon number distribution, the molecular weight and the polarity of the pour point depressant, so that the application range of the pour point depressant is wider;
5. the carbon chain length and the mixed design in the crude oil pour point depressant depend on the carbon chain distribution of wax in a target area, and are explained according to similar compatibility, crystal nucleus and eutectic theory, so that the product has stronger adaptability and the product performance is improved.
In summary, the first polymer and the second polymer are compounded and then crosslinked to obtain the multi-branched polymer pour point depressant, and compared with a simple compound product, the product performance is greatly improved. The obtained crude oil pour point depressant has polar groups and nonpolar groups simultaneously, nonpolar groups such as high-carbon alcohol and the like and wax are subjected to eutectic, and polar groups such as urethane groups, urea groups, biuret groups and the like prevent wax crystals from growing up, so that the solidifying point of crude oil is reduced, and the purpose of improving the fluidity of the crude oil is achieved.
The technical characteristics form the embodiment of the invention, have stronger adaptability and implementation effect, and can increase or decrease unnecessary technical characteristics according to actual needs so as to meet the requirements of different situations.
Claims (2)
1. The preparation method of the crude oil pour point depressant is characterized by comprising the following steps of: a first step of preparing a first polymer, a second step of preparing a second polymer, a third step of uniformly mixing the first polymer and the second polymer at 80 ℃ to 100 ℃ and dropwise adding a required amount R 4 (CNO) 2 Crosslinking reaction is carried out for 1 to 2 hours to obtain crude oil pour point depressant R 4 (CNO) 2 Toluene diisocyanate, and R 4 (CNO) 2 Is 1 to 5% by mass of the total dry mass of the first polymer and the second polymer;
the first polymer is prepared according to the following method: first, a desired amount of a polyanhydride compound or a polycarboxylic compound is reacted with R under the action of p-toluenesulfonic acid 2 Carrying out esterification reaction on OH to obtain a first polymer intermediate, wherein the esterification reaction temperature is 100-200 ℃, the esterification reaction time is 4-8 h, and in the esterification reaction, carboxyl groups in the polycarboxylic compound and R 2 The molar ratio of hydroxyl groups in the OH is 1.5 to 2.5:1 or anhydride groups to R in the polyanhydride compound 2 The molar ratio of hydroxyl groups in the OH is 1.5 to 2.5:2; then, the first polymer intermediate is subjected to a crosslinking reaction with a required amount of amino compound to obtain a first polymer, wherein the crosslinking reaction temperature is 80-140 ℃, the crosslinking reaction time is 1-5 h, the molar ratio of carboxyl groups in the first polymer intermediate to primary amino groups in the amino compound is 0.5-2:1, and in the preparation of the first polymer, the polyanhydride group compound or the polycarboxylic compound is pyromellitic dianhydride, biphenyl tetracarboxylic dianhydride, cyclohexane tetracarboxylic dianhydride, pyromellitic acid, biphenyl tetracarboxylic acid, cyclohexane tetracarboxylic acid, R 2 -OH is a compound or composition carrying a hydroxyl group, wherein R 2 Straight chain alkyl of C14 to C40, C14 to C40 isomerism alkyl, amino compound is ethylenediamine, hexamethylenediamine, diethylenetriamine, tetraethylenepentamine;
the second polymer is prepared according to the following method: firstly, mixing a required amount of EVA, cinnamic acid and maleic anhydride, adding an initiator di-tert-butyl peroxide, and performing polymerization reaction to obtain a second polymer intermediate I, wherein the polymerization reaction temperature is 100-200 ℃, and the molar ratio of EVA, cinnamic acid and maleic anhydride is 0.01-1:0.1-3:1-9; then, the second polymer intermediate-is reacted with the desired amount R under the influence of p-toluene sulfonic acid 2 -OH to obtain a second polymer intermediate II, wherein the esterification temperature is 100-200 ℃, and in the esterification, carboxyl and R are reacted 2 The molar ratio of-OH is from 1:0.25 to 0.95 or anhydride groups to R 2 -OH in a molar ratio of 1:0.5 to 1.90; finally, the desired amount R is added to the second polymer intermediate II 5 R 3 NH 2 Carrying out amidation reaction to obtain a second polymer, wherein the amidation reaction temperature is 80-150 ℃, R 5 R 3 NH 2 Is ethylenediamine, diethylenetriamine, tetraethylenepentamine, and ethanolamine.
2. A crude oil pour point depressant obtained according to the process of claim 1.
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