CN108017588B - Triazine natural gas drag reducer and synthesis method and application thereof - Google Patents
Triazine natural gas drag reducer and synthesis method and application thereof Download PDFInfo
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- CN108017588B CN108017588B CN201610968512.6A CN201610968512A CN108017588B CN 108017588 B CN108017588 B CN 108017588B CN 201610968512 A CN201610968512 A CN 201610968512A CN 108017588 B CN108017588 B CN 108017588B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- C07D251/52—Two nitrogen atoms with an oxygen or sulfur atom attached to the third ring carbon atom
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F17—STORING OR DISTRIBUTING GASES OR LIQUIDS
- F17D—PIPE-LINE SYSTEMS; PIPE-LINES
- F17D1/00—Pipe-line systems
- F17D1/02—Pipe-line systems for gases or vapours
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Abstract
The invention discloses a triazine natural gas drag reducer. The molecular structural formula is as follows:
. The drag reducer is synthesized by the following method: dissolving cyanuric chloride in a solvent, dropwise adding alcohol and inorganic base at-15-0 ℃, reacting for 2-6 h at-15-0 ℃, adding morpholine and inorganic base after the reaction is finished, reacting for 6-12 h at 50-100 ℃, washing with water after the reaction is finished, and drying to obtain the product. The drag reducer provided by the invention has a multi-polar end and a non-polar end, and has good adsorption performance and excellent drag reduction and delivery increase effects. The invention has the advantages of simple synthesis process, mild condition, short time, low requirement on equipment and easy realization of large-scale industrial production.
Description
Technical Field
The invention belongs to the field of organic chemistry, and particularly relates to a triazine natural gas drag reducer as well as a preparation method and application thereof.
Background
As an efficient and clean energy source, natural gas has become the best choice for improving the environment and promoting the sustainable development of economy in all countries of the world, and the demand of natural gas is increasing day by day.
In the process of transporting natural gas by a pipe, the roughness of the inner wall of the pipe can generate frictional resistance, so that gas vortex is generated, and the on-way pressure drop and the energy loss are caused. Therefore, to increase the gas transportation amount, it is necessary to reduce the resistance during the transportation of the natural gas and reduce the energy loss. The main methods for reducing drag and increasing output are an inner coating drag reduction technology and a drag reducer drag reduction technology. In recent years, natural gas pipeline drag reduction conveying becomes a research hotspot at home and abroad, and by reducing pipeline friction and inhibiting radial pulsation, the aims of reducing on-way pressure drop and energy loss, reducing conveying pressure and improving conveying efficiency are achieved, and meanwhile, the safety risk caused by pipeline pressurization can also be reduced. At present, natural gas drag reduction conveying has not been industrially applied, but has shown huge economic value and application potential. Therefore, the research on the natural gas drag reduction conveying process technology has important significance for improving the flowability of natural gas, improving the pipe conveying efficiency and guaranteeing the safe operation of a pipeline, and simultaneously has better actual production requirements and market prospects.
The natural gas drag reducer is a compound similar to a surfactant structure, has a polar end and a non-polar end, after the natural gas drag reducer is filled into a pipeline, the polar end is adsorbed on the inner wall of the pipeline through a coordination bond, and the non-polar end exists between a fluid and the inner surface of the pipeline and is suspended in an airflow in a downstream direction under the action of shear stress to form a layer of film. The film can partially fill the depressions on the wall surface of the tube, and serves to reduce roughness. Meanwhile, in the process of recovering and extending the molecules, part of energy of the fluid molecules impacting the inner wall is absorbed and returned to the fluid, the radial pulsation of the gas and the pulsation generated by the rough bulges are reduced, and the vortex energy is reduced, so that the flow resistance is reduced, and the aim of reducing the resistance is fulfilled. Therefore, the development of natural gas drag reducers with strong polar-end adsorptivity and moderate flexible-end has become one of the active petrochemical additive fields in recent years.
US 5902784A and Chinese patent CN 101575495A respectively disclose a synthetic method of a nitrogen-containing natural gas drag reducer and are used for drag reduction and transportation enhancement of a gas pipeline, CN 102040908A discloses that trimethoxy silane and α -dodecene are used as raw materials, and under the condition of the presence of a platinum catalyst, the dodecyl trimethoxy silane drag reducer is synthesized, and the Mannich base drag reducer synthesized by a two-step method in patent CN 101328442A can be applied to drag reduction and transportation enhancement of a natural gas gathering and transportation pipeline.
In addition, there are some reports on the synthesis of nitrogen-containing drag reducers, such as patent CN 102838606 a also discloses the preparation of a porphyrin-based natural gas drag reducer, and patent CN 101575497 a; US 5549848A; CN 101328441A; CN 101329011A; w.g. Xing et al (polymer. degrad. stab. 2011, 92: 74-78); asahi et al (Natural gas industry 2010, 30: 92-96). Patents CN 102443022A and CN 102863473 a report phosphorous drag reducers octadecyl alcohol phosphate ammonium salts and six-membered cycloalkyl siloxane-phosphate esters, respectively.
However, the natural gas drag reducers reported in the above patents and documents have some disadvantages, mainly including single polar end, weak adsorptivity, few non-polar ends (such as octadecyl alcohol phosphate ammonium salt), unobvious drag reduction effect, and poor solubility (such as hexa-membered cyclic alkyl siloxane-phosphate), which cannot be applied to natural gas pipeline drag reduction in large scale, so the application range is greatly limited, and the drag reduction effect needs to be further improved.
Disclosure of Invention
Aiming at the defects of poor adsorptivity, few polar chain ends and poor drag reduction effect of the conventional natural gas drag reducer, the invention provides a triazine natural gas drag reducer and a synthesis method thereof. The drag reducer has the characteristics of strong multi-polar-end adsorption and good drag reduction effect. The synthesis method is simple, the reaction time is short, and the solvent is low in toxicity and pollution-free.
The invention provides a triazine drag reducer, which has a molecular structural formula shown as a formula (I):
in the formula (I), R is any one of aromatic groups.
The invention also provides a synthetic method of the triazine drag reducer, which comprises the following steps:
dissolving cyanuric chloride in a solvent, adding alcohol and inorganic base at the temperature of-15-0 ℃, reacting for 2-6 h at the temperature of-15-0 ℃, and stopping the reaction; adding morpholine and inorganic base under stirring, and continuously reacting for 6-12 h at the temperature of 50-100 ℃; and after the reaction is finished, carrying out suction filtration, and washing and drying the crude product to obtain the triazine drag reducer.
In the method, the molar ratio of cyanuric chloride to alcohol is 1: 1-1: 2, preferably 1: 1-1: 1.5; the molar ratio of alcohol to inorganic base is 1: 1-1: 2, preferably 1: 1-1: 1.5; the molar ratio of cyanuric chloride to morpholine is 1: 2-1: 3, preferably 1: 2-1: 2.5; the molar ratio of morpholine to inorganic base is 1: 1-1: 2, preferably 1: 1-1: 1.5.
in the method of the invention, the solvent is selected from one or more of acetone, toluene and water, and is preferably acetone.
In the method, the alcohol is one of aromatic alcohols.
In the method of the present invention, the inorganic base is selected from the group consisting of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate, and sodium hydroxide is preferred.
In the invention, the washing and drying are conventional operations well known to those skilled in the art, for example, the washing can be washed with water, and the drying temperature is 60-150 ℃.
The synthetic route of the drag reducer of the invention is as follows:
the invention also provides application of the synthesized natural gas drag reducer in natural gas pipeline transportation. The drag reducer synthesized by the invention can improve the gas transmission amount, reduce the gas transmission power and meet the requirement of seasonal peak regulation in the natural gas pipeline transportation, thereby reducing the risk of the full-load operation of the pipeline. In addition, the synthesized drag reducer can also play auxiliary functions of repairing internal coating defects, inhibiting corrosion and the like.
The product of the invention is used as a natural gas drag reducer, and is generally prepared into solutions of ethanol, gasoline, diesel oil or acetone and the like to be applied to drag reduction and transportation increase of natural gas pipelines. The content of the triazine natural gas drag reducer in the prepared solution is generally 5-150 g/L.
Besides, the product of the invention also has a certain corrosion inhibition function on the natural gas pipeline.
The triazine natural gas drag reducer is a compound with a multi-polar end and a non-polar end, is used as a drag reduction additive of a natural gas pipeline, is atomized and injected or coated on the inner wall of the pipeline, the polar end of the compound is firmly adsorbed on the inner surface of the pipeline metal, and a smooth film is formed, the non-polar end exists between the fluid of the pipeline and the inner surface, part of the non-polar end fills the dent of the inner surface of the pipeline, the roughness is reduced, the non-polar end is suspended in the airflow in a downstream direction under the action of shear stress, part of energy of fluid molecules impacting the inner wall is absorbed and returned to the fluid in the process of recovering and extending the molecules, the radial pulsation of the gas and the pulsation generated by rough bulges are reduced, and. The product of the invention is white or light yellow solid, the yield is more than 85 percent, and the product has good adsorption performance and excellent drag reduction and delivery increase effects on the metal surface.
The invention has simple synthesis process, mild reaction condition, short reaction time and low requirement on equipment, is easy to realize large-scale industrial production, and overcomes the defects of poor adsorptivity and short duration of drag reduction effect of the existing natural gas drag reducer.
Drawings
FIG. 1 is a graph showing electrochemical impedance spectra of a white iron electrode and the iron electrode after film formation using the drag reducer obtained in example 1.
Detailed Description
The triazine based natural gas drag reducing agent and the method for preparing the same of the present invention are further illustrated by the following examples, which are provided only for illustrating the present invention and are not intended to limit the present invention.
In the examples, electrochemical tests and data analysis were carried out on the samples tested using an electrochemical workstation, IM6, ZAHZER, germany; the used indoor loop test evaluation device is a self-made test device.
Example 1
In a 3000mL four-necked flask equipped with a reflux condenser, a thermometer, a stirrer and a constant pressure dropping funnel were placed 110.4g of cyanuric chloride and 600mL of acetone, the four-necked flask was cooled to-15 ℃ and, while stirring, 56.5g of phenol and 360.0g of a 10wt% sodium hydroxide solution were slowly added while controlling the temperature of the system to not more than 0 ℃. After the dripping is finished, the reaction is carried out for 6h at the temperature of-15 to 0 ℃. The reaction was stopped, 104.4g of morpholine and 480.0g of 10wt% sodium hydroxide solution were added to the system, and the reaction was carried out at 100 ℃ for 8 hours. After the reaction is finished, suction filtration is carried out, the crude product is washed by distilled water and dried at 100 ℃ to obtain 175.5g of white product, and the yield is 85.3%.
The structural formula of the product obtained in this embodiment is as follows:
and (4) performing electrochemical test. The iron electrode (Q235) was encapsulated with epoxy, exposing only the tip to contact the solution. Before each experiment, the surface of the iron electrode is polished to a mirror surface by using No. 2000 abrasive paper, washed by water and ethanol, naturally dried, sprayed with 20g/L of prepared drag reducer ethanol solution, and naturally dried. A three-chamber electrolytic cell is adopted, a working electrode is an iron electrode, a reference electrode is a saturated calomel electrode, a platinum electrode is an auxiliary electrode, a sine perturbation signal with the amplitude of 5mV is selected, the sine perturbation signal is scanned from high frequency to low frequency within the frequency range of 0.02Hz-60kHz, and electrochemical impedance spectroscopy test is carried out in 3.5% NaCl solution. The film forming property of the drag reducer on the surface of the steel is tested by electrochemical impedance spectroscopy.
FIG. 1 is the electrochemical impedance spectrum of a blank iron electrode and the iron electrode after film formation. The literature reports that the charge transfer resistance of the film is increased, and the capacitive arc is also increased, so that the higher the low-frequency arc is, the better the barrier effect of the film on the surface electrode process and the film forming effect on the iron electrode are. Because the iron electrode is in a semicircular capacitive arc resistance in a low-frequency area, the electrochemical reaction process of the surface of the iron electrode is mainly controlled by a charge transfer process. As can be seen from fig. 1, the blank sample has a smaller capacitive arc resistance, indicating that the blocking effect of the iron electrode without film formation is smaller. After the film of the drag reducer is formed on the surface of the iron electrode, two continuous capacitive arcs are formed from a high frequency area to a low frequency area. The smaller capacitive arc is formed in a high-frequency area and is the capacitive arc of film formation of the drag reducer, which shows that the drag reducer forms a barrier film on the surface of an iron electrode, and then forms a larger capacitive arc in a low-frequency area, and is the capacitive arc of the iron electrode after film formation, and the diameter of the capacitive arc is larger than that of a blank iron electrode.
Indoor loop test analysis shows that the product is prepared into ethanol solution, atomized and injected into a loop, the test pressure is 0.5-0.6MPa, when the concentration of the drag reducer is 20g/L, the average drag reduction rate can reach 7.1%, and the effective period is more than 30 days.
Example 2
110.4g of cyanuric chloride and 600mL of acetone were placed in a 3000mL four-necked flask equipped with a reflux condenser, a thermometer, a stirrer and a constant pressure dropping funnel, the four-necked flask was cooled to-15 ℃ and, while stirring, 64.9g of benzyl alcohol and 360.0g of a 10wt% sodium hydroxide solution were slowly added while controlling the temperature of the system to not more than 0 ℃. After the dripping is finished, the reaction is carried out for 5 hours at the temperature of between 15 ℃ below zero and 0 ℃. The reaction was stopped, 104.4g of morpholine and 480.0g of 10wt% sodium hydroxide solution were added to the system, and the reaction was carried out at 100 ℃ for 8 hours. After the reaction, the reaction solution was filtered, and the crude product was washed with distilled water and dried at 100 ℃ to obtain 186.1g of a white product with a yield of 86.9%.
The structural formula of the product obtained in this embodiment is as follows:
indoor loop test analysis shows that the product is prepared into ethanol solution, atomized and injected into a loop, the test pressure is 0.5-0.6MPa, when the concentration of the drag reducer is 20g/L, the average drag reduction rate can reach 7.5%, and the effective period is more than 30 days.
Example 3
In a 3000mL four-necked flask equipped with a reflux condenser, a thermometer, a stirrer and a constant pressure dropping funnel were placed 110.4g of cyanuric chloride and 600mL of acetone, the four-necked flask was cooled to-15 ℃ and, while stirring, 73.3g of 2-ethylphenol and 360.0g of a 10wt% sodium hydroxide solution were slowly added while controlling the temperature of the system to not more than 0 ℃. After the dripping is finished, the reaction is carried out for 6h at the temperature of-15 to 0 ℃. The reaction was stopped, 104.4g of morpholine and 480.0g of 10wt% sodium hydroxide solution were added to the system, and the reaction was carried out at 100 ℃ for 10 hours. After the reaction, the reaction solution was filtered, and the crude product was washed with distilled water and dried at 100 ℃ to obtain 189.2g of a white product with a yield of 85.0%.
The structural formula of the product obtained in this embodiment is as follows:
indoor loop test analysis shows that the product is prepared into ethanol solution, atomized and injected into a loop, the test pressure is 0.5-0.6MPa, when the concentration of the drag reducer is 20g/L, the average drag reduction rate can reach 7.0%, and the effective period is more than 30 days.
Example 4
The solvent used in step one of this embodiment is 500mL of toluene, and the rest is the same as in example 1. 176.1g of white product was obtained in 85.6% yield.
Example 5
This example uses 100.8g of inorganic base and 50.4g of sodium bicarbonate in step one, the rest being the same as example 1. 175.1g of white product was obtained in 85.1% yield.
Claims (3)
1. The application of the triazine compound in natural gas pipeline transportation is disclosed, wherein the triazine compound is used as a natural gas drag reducer, and the molecular structural formula of the triazine compound is shown as the formula (I):
in the formula (I), R is phenyl, 2-ethyl phenyl or benzyl.
2. Use according to claim 1, wherein the triazine compound is used by formulating it into an ethanol, gasoline, diesel or acetone solution.
3. The use according to claim 2, wherein the triazine compound is contained in the solution to be prepared in an amount of 5 to 150 g/L.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3897430A (en) * | 1973-09-24 | 1975-07-29 | American Cyanamid Co | Substituted s-triazines and method of use |
| CN105175402A (en) * | 2015-09-02 | 2015-12-23 | 陕西师范大学 | Synthetic method of 2-subsituted-4,6-dithienyl-1,3,5-s-triazine compounds |
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| EP2219646A4 (en) * | 2007-12-21 | 2010-12-22 | Univ Rochester | Method for altering the lifespan of eukaryotic organisms |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3897430A (en) * | 1973-09-24 | 1975-07-29 | American Cyanamid Co | Substituted s-triazines and method of use |
| CN105175402A (en) * | 2015-09-02 | 2015-12-23 | 陕西师范大学 | Synthetic method of 2-subsituted-4,6-dithienyl-1,3,5-s-triazine compounds |
Non-Patent Citations (2)
| Title |
|---|
| "2,4-Bis(morpholin-4-yl)-6-phenoxy-1,3,5-triazine";Jasmine P. Vennila，等;《Acta Crystallographica, Section E: Structure Reports Online》;20111231;第67卷(第9期);第o2451页及其supporting information * |
| "sym-Triazines for Directed Multitarget Modulation of Cholinesterases and Amyloid-β in Alzheimer’s Disease";Anthony J. Veloso，等;《ACS Chem. Neurosci.》;20121030;第4卷;第339-349页 * |
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