CN113717061B - Y-shaped structural demulsifier and preparation method and application thereof - Google Patents
Y-shaped structural demulsifier and preparation method and application thereof Download PDFInfo
- Publication number
- CN113717061B CN113717061B CN202110987552.6A CN202110987552A CN113717061B CN 113717061 B CN113717061 B CN 113717061B CN 202110987552 A CN202110987552 A CN 202110987552A CN 113717061 B CN113717061 B CN 113717061B
- Authority
- CN
- China
- Prior art keywords
- demulsifier
- shaped structural
- organic solvent
- triglycidyl ether
- demulsification
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 19
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 claims abstract description 18
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 239000012044 organic layer Substances 0.000 claims abstract description 8
- 238000000605 extraction Methods 0.000 claims abstract description 6
- 239000012298 atmosphere Substances 0.000 claims abstract description 5
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 238000003756 stirring Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 239000007762 w/o emulsion Substances 0.000 claims description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 5
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims 2
- 239000000839 emulsion Substances 0.000 description 20
- 239000010779 crude oil Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 10
- 238000004062 sedimentation Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000002283 diesel fuel Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000009471 action Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 238000012835 hanging drop method Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- 241001391944 Commicarpus scandens Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- 238000009428 plumbing Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 239000002569 water oil cream Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G33/00—Dewatering or demulsification of hydrocarbon oils
- C10G33/04—Dewatering or demulsification of hydrocarbon oils with chemical means
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1033—Oil well production fluids
Abstract
The invention provides a Y-shaped structural demulsifier, and a preparation method and application thereof, wherein the preparation method of the Y-shaped structural demulsifier comprises the following steps: completely dissolving glycerol triglycidyl ether in an organic solvent, then adding dodecyl amine, and stirring under the condition of oil bath under the protection atmosphere to react to obtain a mixture; cooling the mixture, and distilling off the organic solvent under vacuum to obtain a residual product; dissolving the rest product in an organic solvent, and removing unreacted glycerol triglycidyl ether and dodecylamine through extraction; and separating to obtain an organic layer, and distilling off the organic solvent under a vacuum condition to obtain the Y-shaped structure demulsifier. The Y-shaped structure demulsifier can obtain higher demulsification efficiency under lower usage amount, and the demulsification temperature is lower and the demulsification time is shorter.
Description
Technical Field
The invention belongs to the field of crude oil demulsifiers, and particularly relates to a Y-shaped structure demulsifier and a preparation method and application thereof.
Background
With the increasing difficulty of crude oil extraction, tertiary oil recovery technology using water-polymer flooding has been commonly adopted by various large oil fields in recent years, and the extracted crude oil exists in the form of water-in-oil (W/O) or oil-in-water (O/W). The use of mechanical equipment and the presence of natural actives such as asphaltenes in the process makes crude oil emulsions highly stable, such emulsions not only causing corrosion and damage to plumbing equipment, but also increasing energy consumption during transportation. Therefore, it is important to perform efficient oil-water separation of crude oil emulsions.
The chemical demulsification is to add a certain amount of chemical agent into the emulsion to destabilize the crude oil emulsion, and finally realize the rapid separation of oil and water under the action of gravity and the like. The traditional demulsifier has the problems of low demulsification efficiency, high demulsification temperature, large dosage of the demulsifier, overlong demulsification time, unclear separated water phase and the like. For example, ezzat et al synthesized a series of vinylamine demulsifiers (DNPA-6, DNPA-5 and DNPA-4) in a one-step process by interaction of pentaethylenehexamine, tetraethylenepentamine or triethylenetetramine with glycidyl ester-4-nonylphenyl ether. The demulsification test result shows that: DNPA-6, DNPA-5 and DNPA-4 have demulsification efficiencies of 80%, 76% and 56% in crude oil emulsion respectively when the adding amount is 1000mg/L, the demulsification temperature is 60 ℃ and the sedimentation time is 60 min. Therefore, the development of the demulsifier with high efficiency, low cost and simple synthesis method has very important significance.
Disclosure of Invention
Aiming at the defects of the prior art, the primary purpose of the invention is to provide a Y-shaped structure demulsifier, which can obtain higher demulsification efficiency under lower usage amount, and meanwhile, the demulsification temperature is lower than that of the prior demulsifier, and the demulsification time is shorter than that of the prior demulsifier.
The invention further aims at providing a preparation method and application of the Y-shaped structure demulsifier.
The aim of the invention is achieved by the following technical scheme:
a preparation method of a Y-shaped structural demulsifier comprises the following steps:
s1, completely dissolving glycerol triglycidyl ether in an organic solvent, then adding dodecyl amine, and stirring and reacting for 4-5 hours under the oil bath condition of 120-130 ℃ under the protective atmosphere to obtain a mixture;
s2, cooling the mixture, and distilling off the organic solvent under the vacuum condition to obtain a residual product;
s3: firstly, dissolving the rest products in an organic solvent, and removing unreacted glycerol triglycidyl ether and dodecylamine through extraction; then separating to obtain an organic layer, and distilling off the organic solvent under the vacuum condition to obtain the Y-shaped structure demulsifier.
Preferably, in step S1, the molar amount ratio of glycerol triglycidyl ether to dodecylamine is 0.9-1.1:2.8-3.2; more preferably 1:3.
Preferably, in step S1, the organic solvent is at least one of 1, 4-xylene, 1, 2-xylene and 1, 3-xylene.
Preferably, in the step S1, the adding amount of the glycerol triglycidyl ether in the organic solvent is 0.05-0.08g/mL.
Preferably, in step S1, the protective atmosphere is nitrogen.
Preferably, in step S2, the mixture is cooled to 100 ℃.
Preferably, in step S3, the organic solvent is isopropanol.
Preferably, in step S3, the extraction method is as follows: the unreacted glycerol triglycidyl ether and the dodecyl amine are dissolved by using supersaturated NaCl solution.
Preferably, in step S3, the separation method for obtaining the organic layer is as follows: the organic layer was separated by a separating funnel.
Preferably, in step S3, the temperature of the distillation is 80 ℃.
The Y-shaped structure demulsifier prepared by the preparation method of the Y-shaped structure demulsifier.
The application of the Y-shaped structural demulsifier in the demulsification of water-in-oil emulsion is characterized in that the effective components of the Y-shaped structural demulsifier have the following structures:
the application method of the Y-shaped structural demulsifier in the demulsification of the water-in-oil emulsion comprises the following steps: firstly, adding the Y-shaped structural demulsifier into water-in-oil emulsion, wherein the concentration of the Y-shaped structural demulsifier is 100-500 mg/L, and then demulsifiing the emulsion at 40-80 ℃ for 10-120 min; more preferred are: firstly, adding the Y-shaped structural demulsifier into water-in-oil emulsion, wherein the concentration of the Y-shaped structural demulsifier is 400mg/L, and then demulsifying for 30min at 50 ℃.
The reaction mechanism of the invention is as follows: after the Y-shaped structural demulsifier is added into the W/O emulsion, the Y-shaped structural demulsifier has higher interfacial activity and lower interfacial tension, and is not separated from the structure of the Y-shaped structural demulsifier which has a longer hydrophobic chain segment, so that the Y-shaped structural demulsifier can rapidly move towards an interface. At this time, the Y-shaped structure demulsifier molecules can effectively penetrate through the asphaltene membrane at the oil-water interface, so that the strength of the asphaltene membrane is reduced, and the asphaltene membrane is easy to break. Water droplets of comparable size can merge into one another while small droplets are easily engulfed by larger droplets in their vicinity to form larger droplets. Finally, large water drops or water clusters are further fused and combined and then sink to the bottom of the bottle under the action of gravity, so that oil-water separation is realized.
Compared with the prior art, the invention has the beneficial effects that:
(1) According to the invention, firstly, the glycerol triglycidyl ether and the dodecylamine are reacted in one step to obtain a crude product, and then the crude product is purified by utilizing the dissolving and salting-out processes of an organic solvent, so that the preparation method is simple, and the period of obtaining the product is short.
(2) The Y-shaped structure demulsifier can realize effective separation of oil-water emulsion at a lower temperature (the demulsification efficiency is up to 87.55% at the addition amount of 400mg/L at the temperature of 40-50 ℃).
(3) The Y-shaped structural demulsifier can quickly destabilize and demulsify crude oil emulsion (the demulsification efficiency of 87.55% can be achieved only by 30min at the demulsification temperature of 50 ℃ and the addition amount of 400 mg/L).
Drawings
FIG. 1 is a schematic diagram of the synthesis of a Y-configuration demulsifier as described in example 1.
FIG. 2 is a 1H NMR chart of a Y-type structural demulsifier described in example 1.
FIG. 3 is an infrared spectrum of the Y-configuration demulsifier described in example 1.
FIG. 4 is an interfacial tension diagram of the Y-shaped demulsifier prepared in example 1 at different concentrations, wherein the inset corresponds to the blank.
Detailed Description
The present invention will be described in further detail with reference to the drawings and examples, in order to make the objects, technical solutions and advantages of the present invention more apparent. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the invention.
The crude oil emulsions described in the examples and comparative examples were formulated using the following protocol: 110g of dehydrated crude oil and 390 g of distilled water were thoroughly mixed and then stirred at 11000 r.min -1 Stirring at high speed for 20min at a rotating speed to obtain crude oil emulsion (water-in-oil emulsion) containing 22% of oil. Crude oil samples were derived from long-lived oil fields (China Ningxia).
The Demulsification Efficiency (DE) is calculated according to the following formula:
DE(%)=H/(0.78H 0 )×100%
wherein H is the height of the separated water phase, H 0 Is the height of the original emulsion.
Example 1
A preparation method of a Y-shaped structural demulsifier comprises the following steps:
s1, 2.6g (0.01 mol) of glycerol triglycidyl ether is completely dissolved in 50mL of xylene, then transferred into a three-necked flask, 5.56g (0.03 mol) of dodecylamine is added, and the mixture is stirred and reacted for 4 hours in an oil bath at 120 ℃ under the protection of nitrogen gas to obtain a mixture;
s2, naturally cooling the mixture to 100 ℃, and distilling to remove 1, 4-dimethylbenzene under vacuum condition to obtain a residual product;
and S3, dissolving the residual product by using isopropanol, extracting by using a supersaturated NaCl aqueous solution, and removing unreacted glycerol triglycidyl ether and dodecylamine.
And S4, separating an organic layer through a separating funnel, and distilling off isopropanol at 80 ℃ under vacuum to obtain a light yellow viscous product, namely the Y-shaped structural demulsifier.
Example 2
The Y-shaped structural demulsifier prepared in the example 1 is added into crude oil emulsion, the concentration of the Y-shaped structural demulsifier is 100-500 mg/L, the demulsification temperature is 50 ℃, the sedimentation time is 10min, and the obtained demulsification efficiency is shown in Table 1.
TABLE 1 influence of demulsifier concentration on demulsification efficiency (I)
Example 3
The Y-shaped structural demulsifier prepared in the example 1 is added into crude oil emulsion, the concentration of the Y-shaped structural demulsifier is 100-500 mg/L, the demulsification temperature is 50 ℃, the sedimentation time is 120min, and the obtained demulsification efficiency is shown in Table 2. By prolonging the demulsification time, the demulsification efficiency can be properly improved.
TABLE 2 influence of demulsifier concentration on demulsification efficiency (II)
As can be seen by comparing table 1 with table 2: by prolonging the demulsification time, the demulsification efficiency can be properly improved.
Example 4
The Y-shaped structural demulsifier prepared in the example 1 is added into crude oil emulsion, the concentration of the Y-shaped structural demulsifier is 100-500 mg/L, the demulsification temperature is 70 ℃, the sedimentation time is 10min, and the obtained demulsification efficiency is shown in Table 3.
TABLE 3 influence of demulsifier concentration on demulsification efficiency (III)
Example 5
The Y-shaped structural demulsifier prepared in the example 1 is added into crude oil emulsion, the concentration of the Y-shaped structural demulsifier is 400mg/L, the demulsification temperature is 50 ℃, the sedimentation time is 10-120 min, and the obtained demulsification efficiency is shown in Table 4.
TABLE 4 influence of sedimentation time on demulsification efficiency
Example 6
The Y-shaped structural demulsifier prepared in the example 1 is added into crude oil emulsion, the concentration of the Y-shaped structural demulsifier is 400mg/L, the demulsification temperature is 40-80 ℃, the sedimentation time is 120min, and the obtained demulsification efficiency is shown in Table 5.
TABLE 5 influence of temperature on demulsification efficiency
Example 7
The Y-shaped structural demulsifier prepared in the example 1 is added into crude oil emulsion, the concentration of the Y-shaped structural demulsifier is 400mg/L, the demulsification temperature is 50 ℃, the sedimentation time is 120min, the salinity (salt is NaCl) is 2000-10000 mg/L, and the demulsification efficiency is shown in Table 6.
TABLE 6 influence of salinity on demulsification efficiency
As can be seen from table 6: the demulsification efficiency of the Y-shaped structure demulsifier is not influenced by the salinity, the demulsification performance is stable, and the Y-shaped structure demulsifier still has higher demulsification efficiency under the emulsion with higher salinity.
Comparative example 1
The Y-type structure demulsifier prepared in example 1 was compared with a conventional commercial demulsifier in terms of performance, the demulsifier concentration in crude oil emulsion was 400mg/L, the demulsification temperature was 50℃and the sedimentation time was 120min, and the names of the commercial demulsifier samples and the corresponding demulsification efficiencies are shown in Table 7.
The names and sources of commercial demulsifiers are specifically as follows:
AE 09, SP 169, AR 321, AR 32 were all purchased from Jingzhou, tianhe scientific and chemical Co., ltd; YF 31 was purchased from Jing Zhoulong of petrochemical company, inc.
TABLE 7 demulsification efficiency for different samples
From table 7, it can be seen that: the demulsification efficiency of the Y-shaped structure demulsifier prepared by the invention can be comparable with that of some excellent commercial demulsifiers, and exceeds that of a part of commercial demulsifiers with poor effects.
FIG. 2 is a Y-shaped demulsifier according to example 1 of the present invention 1 H NMR chart, from which it can be seen: 0.93ppm is-CH 3 Chemical shift of hydrogen (labeled a) on the substrate. The peak at 1.33ppm is-CH 2 Segment(s)Is marked b). to-CH 2 -CH of NH-group 2 The chemical shift of hydrogen occurs at 1.53ppm (marked c). -CH with attached-NH-group 2 The chemical shift of hydrogen occurs at 2.70ppm (marked d). The multiple peaks from 3.5 to 4.0ppm are due to the chemical shift of hydrogen of the glycerol triglycidyl ether molecule as a central core. Unlabeled spikes at 4.65ppm were attributed to solvent (CD 3 OD).
Fig. 3 shows an infrared spectrum of a demulsifier with a Y-shaped structure prepared in example 1 of the present invention, which can be seen from the figure: O-H and-NH-groups of glycerol triglycidyl ether dodecyl amine Y-shaped structural demulsifier are 3351cm -1 A broad peak appears. Dodecylamine segment methylene (-CH) 2 -) expansion and contraction at 2921 and 2850cm -1 Two characteristic peaks appear there. About 1614cm -1 The peak at which is the C-N stretch in-C-NH-. Furthermore, the planar flexural vibration of-OH is 1467cm -1 Where a peak occurs. At 1325 and 1097cm -1 The nearby peaks are C-O-C and C-O stretching vibrations.
Testing the interfacial tension:
blank group: the diesel oil is not added with any component and is used as an oil phase, and the oil-water interfacial tension is measured by a hanging drop method;
experimental group: the Y-type structure demulsifier described in example 1 was added to diesel oil so that the concentration of the demulsifier was 100mg/L, 200mg/L, 300mg/L, 400mg/L and 500mg/L, respectively, and the diesel oil of the demulsifier of the above different concentrations was used as an oil phase, and interfacial tension was measured by a hanging drop method. The test results are shown in FIG. 4.
FIG. 4 shows interfaces Zhang Litu of the Y-shaped demulsifier prepared in example 1 at different concentrations. As can be seen from fig. 4: the interfacial tension is firstly reduced rapidly, which indicates that the Y-shaped structural demulsifier is diffused to the oil-water interface rapidly, and then the interfacial tension tends to be balanced, which indicates that the adsorption reaches a saturated state. In general, the result of interfacial tension shows that the Y-shaped structural demulsifier has higher interfacial activity, can quickly migrate to an oil-water interface to reduce the interfacial tension, and promotes flocculation and coalescence of water drops.
The above-described embodiments of the present invention do not limit the scope of the present invention. Any other corresponding changes and modifications made in accordance with the technical idea of the present invention shall be included in the scope of the claims of the present invention.
Claims (9)
1. The preparation method of the Y-shaped structural demulsifier is characterized by comprising the following steps of:
s1, completely dissolving glycerol triglycidyl ether in an organic solvent, then adding dodecyl amine, and stirring and reacting for 4-5 hours under the oil bath condition of 120-130 ℃ under the protective atmosphere to obtain a mixture;
s2, cooling the mixture, and distilling off the organic solvent under the vacuum condition to obtain a residual product;
s3: firstly, dissolving the rest products in an organic solvent, and removing unreacted glycerol triglycidyl ether and dodecylamine through extraction; then separating to obtain an organic layer, and distilling off the organic solvent under vacuum condition to obtain the Y-shaped structure demulsifier;
the Y-shaped structural demulsifier has the following structure:
。
2. the method for preparing a demulsifier with a Y-shaped structure according to claim 1, wherein in the step S1, the molar ratio of the glycerol triglycidyl ether to the dodecyl amine is 0.9-1.1:2.8-3.2.
3. The method for preparing a demulsifier with a Y-shaped structure according to claim 2, wherein in the step S1, the molar ratio of the glycerol triglycidyl ether to the dodecanol is 1:3.
4. The method for preparing a demulsifier with a Y-shaped structure according to claim 1, wherein in the step S1, the glycerol triglycidyl ether is added into the organic solvent in an amount of 0.05-0.08g/mL.
5. The method for preparing a demulsifier with a Y-type structure according to any one of claims 1 to 4, wherein in the step S1, the organic solvent is at least one of 1, 4-xylene, 1, 2-xylene and 1, 3-xylene;
in the step S1, the protective atmosphere is nitrogen;
in step S2, the mixture is cooled to 100 ℃;
in step S3, the organic solvent is isopropanol.
6. The method for preparing a demulsifier with a Y-shaped structure according to any one of claims 1 to 4, wherein in step S3, the extraction method is as follows: dissolving unreacted glycerol triglycidyl ether and dodecyl amine by using supersaturated NaCl solution;
in the step S3, the temperature of the distillation is 80 ℃;
in step S3, the manner of separating the organic layer is as follows: the organic layer was separated by a separating funnel.
7. The application of the Y-shaped structural demulsifier in the demulsification of the water-in-oil emulsion is characterized in that the effective components of the Y-shaped structural demulsifier have the following structures:
。
8. the application according to claim 7, characterized in that it comprises the steps of: firstly, adding the Y-shaped structural demulsifier into the water-in-oil emulsion, wherein the concentration of the Y-shaped structural demulsifier is 100-500 mg/L, and then demulsifiing at 40-80 ℃ for 10-120 min.
9. The application according to claim 8, characterized in that it comprises the steps of: firstly, adding the Y-shaped structural demulsifier into water-in-oil emulsion, wherein the concentration of the Y-shaped structural demulsifier is 400mg/L, and then demulsifying for 30min at 50 ℃.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110987552.6A CN113717061B (en) | 2021-08-26 | 2021-08-26 | Y-shaped structural demulsifier and preparation method and application thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110987552.6A CN113717061B (en) | 2021-08-26 | 2021-08-26 | Y-shaped structural demulsifier and preparation method and application thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN113717061A CN113717061A (en) | 2021-11-30 |
CN113717061B true CN113717061B (en) | 2024-01-30 |
Family
ID=78678120
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202110987552.6A Active CN113717061B (en) | 2021-08-26 | 2021-08-26 | Y-shaped structural demulsifier and preparation method and application thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN113717061B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114773589B (en) * | 2022-05-06 | 2024-02-23 | 麦加芯彩新材料科技(上海)股份有限公司 | Low-temperature demulsifier and preparation method and application thereof |
CN114890921A (en) * | 2022-06-23 | 2022-08-12 | 麦加芯彩新材料科技(上海)股份有限公司 | Multi-branch sulfonated betaine ionic liquid and preparation method and application thereof |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7504438B1 (en) * | 2001-12-20 | 2009-03-17 | Nalco Company | Demulsifiers, their preparation and use in oil bearing formations |
CN101443048A (en) * | 2004-04-20 | 2009-05-27 | 德瑞迪克纳米科技公司 | Dendritic polymers with enhanced amplification and interior functionality |
CN104447424A (en) * | 2014-11-13 | 2015-03-25 | 武汉钢铁(集团)公司 | Ammonium sulfamate demulsifier, synthesis method thereof and application of ammonium sulfamate in cold rolling of waste emulsion |
CN106832254A (en) * | 2017-02-22 | 2017-06-13 | 济南惠信实业有限公司 | The preparation method of desalination type demulsifier |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9816050B2 (en) * | 2014-10-27 | 2017-11-14 | Dean Blankenburg | Oil extraction method and composition for use in the method |
-
2021
- 2021-08-26 CN CN202110987552.6A patent/CN113717061B/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7504438B1 (en) * | 2001-12-20 | 2009-03-17 | Nalco Company | Demulsifiers, their preparation and use in oil bearing formations |
CN101443048A (en) * | 2004-04-20 | 2009-05-27 | 德瑞迪克纳米科技公司 | Dendritic polymers with enhanced amplification and interior functionality |
CN104447424A (en) * | 2014-11-13 | 2015-03-25 | 武汉钢铁(集团)公司 | Ammonium sulfamate demulsifier, synthesis method thereof and application of ammonium sulfamate in cold rolling of waste emulsion |
CN106832254A (en) * | 2017-02-22 | 2017-06-13 | 济南惠信实业有限公司 | The preparation method of desalination type demulsifier |
Also Published As
Publication number | Publication date |
---|---|
CN113717061A (en) | 2021-11-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN113717061B (en) | Y-shaped structural demulsifier and preparation method and application thereof | |
CN1295608A (en) | Removal of naphthenic acids in crude oils and distillates | |
CN1295607A (en) | Removal of naphthenic acids in crude oils and distillates | |
CN103987816B (en) | Ionic liquid is used to extract poly-ring aromatic compounds from petroleum | |
US8227383B2 (en) | Low interfacial tension surfactants for petroleum applications | |
Ji et al. | Separation of phenolic compounds from oil mixtures using environmentally benign biological reagents based on Brønsted acid-Lewis base interaction | |
CN111203005A (en) | Oil-containing wastewater demulsifier and preparation method and application thereof | |
CN110628012A (en) | Novel demulsifier | |
US20040147407A1 (en) | Polyether polyesters having anionic functionality | |
US10131606B2 (en) | Tetrarylmethane ethers | |
CN112048335B (en) | Synchronous demulsification water purifier for petroleum produced liquid | |
US4372383A (en) | In situ separation of bitumen from bitumen-bearing deposits | |
US9926506B2 (en) | Tetrarylmethane ethers as fuel markers | |
CN110078163B (en) | Application of polylysine derivative as demulsifier | |
CN110819380B (en) | Crude oil demulsification method | |
CN116814294A (en) | Polyether demulsifier for high-salt low-water crude oil and application thereof | |
US2279780A (en) | Process for the production of highindene-content hydrocarbon oils | |
CN111171327B (en) | Hyperbranched polymer and preparation method and application thereof | |
CN114773589B (en) | Low-temperature demulsifier and preparation method and application thereof | |
CN106495978B (en) | A kind of method and system preparing alkene with discarded oil base drilling fluid | |
CN104140846A (en) | Crude oil demulsifier and preparation method thereof | |
CN114957079B (en) | Demulsifier and preparation method and application thereof | |
CN109593547B (en) | Rapid demulsifier for heavy oil field produced liquid and preparation method thereof | |
US20230365759A1 (en) | Fluorinated dendrimer, preparation method and application thereof | |
RU2103305C1 (en) | Composition for removing asphalt-resin-paraffin deposits |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |