CN117844517B - Desulfurizing agent and preparation method thereof - Google Patents
Desulfurizing agent and preparation method thereof Download PDFInfo
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- CN117844517B CN117844517B CN202410257183.9A CN202410257183A CN117844517B CN 117844517 B CN117844517 B CN 117844517B CN 202410257183 A CN202410257183 A CN 202410257183A CN 117844517 B CN117844517 B CN 117844517B
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- desulfurizing agent
- desulfurizing
- triazine
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- 230000003009 desulfurizing effect Effects 0.000 title claims abstract description 64
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 51
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003607 modifier Substances 0.000 claims abstract description 17
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 claims abstract description 13
- 239000004094 surface-active agent Substances 0.000 claims abstract description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 11
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims description 11
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 11
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 9
- 239000002994 raw material Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 4
- 239000012747 synergistic agent Substances 0.000 claims description 4
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 238000006477 desulfuration reaction Methods 0.000 description 15
- 230000023556 desulfurization Effects 0.000 description 15
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 13
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 13
- TXNXVKSSXJDGIR-UHFFFAOYSA-N OC(C)N1CN(CN(C1)O)O Chemical compound OC(C)N1CN(CN(C1)O)O TXNXVKSSXJDGIR-UHFFFAOYSA-N 0.000 description 7
- 239000010779 crude oil Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- -1 strong oxides Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
The invention relates to the technical field of desulfurizing agent preparation, and discloses a desulfurizing agent and a preparation method thereof. The triazine modifier is prepared by the reaction of the dehydroabietylamine which is a natural derivative and formaldehyde, and is further mixed with the surfactant and the synergist to obtain the desulfurizing agent, so that the desulfurizing agent has a good desulfurizing effect at high temperature, and has the advantages of high desulfurizing speed, high efficiency and complete desulfurizing within 60 minutes; meanwhile, the reaction process is simple, and can be applied to industrial production.
Description
Technical Field
The invention relates to the technical field of desulfurizing agent preparation, in particular to a desulfurizing agent and a preparation method thereof.
Background
Currently, crude oil desulfurization technologies can be broadly divided into three categories: physical desulfurization, chemical desulfurization, biological desulfurization. The physical desulfurization technology has stable solvent property, is not suitable for foaming, has low corrosiveness and has certain absorption capacity on organic sulfides, but the high price of the solvent chromium and the high affinity to heavy hydrocarbon limit the popularization and application of the physical solvent absorption method. Chemical desulfurization includes acid-base neutralization, oxidation, oil extraction, etc. During chemical desulfurization, the desulfurization efficiency of the desulfurizing agent is affected by factors such as different temperatures, pressures, water contents, addition amounts and the like, so that various desulfurizing agents are purposefully selected according to the actual production conditions of the oil field so as to achieve the ideal desulfurization effect. Biological desulfurization includes biological filtration, biological adsorption and biological drip filtration. Biological desulfurization technology has the advantages of low investment, mild reaction conditions, mild environment and the like, and has been paid attention to in recent years.
The key to chemical desulfurization technology is the choice of desulfurizing agent. The most common chemical desulfurizing agents mainly comprise amines, strong oxides, hydroxides, triazines and the like. The invention patent with publication number of CN113831524A discloses a preparation method of a liquid desulfurizing agent and the liquid desulfurizing agent, wherein the method comprises the following steps: adding ethanol into a reaction kettle as a solvent; adding diethylenetriamine, epichlorohydrin, 1,3, 5-trihydroxyethyl hexahydro s-triazine and a catalyst into a reaction kettle; stirring and heating, and controlling the reaction to be continued for a specified period of time at a specified reaction temperature to obtain the liquid desulfurizing agent. Although the liquid desulfurizing agent has better desulfurizing effect, petroleum-based compounds are still used as reaction raw materials, and the liquid desulfurizing agent has no environmental protection in the long term. Therefore, an environment-friendly desulfurizing agent is developed, and the desulfurizing agent has higher value.
Disclosure of Invention
Therefore, the technical problem to be solved by the invention is to overcome the defect that the desulfurizing agent in the prior art uses petroleum-based compounds as raw materials, so as to provide the desulfurizing agent and the preparation method thereof, wherein the triazine modifier is prepared by using natural derivatives as raw materials, and the desulfurizing agent is further obtained, so that the desulfurizing efficiency is improved, and the desulfurizing agent is environment-friendly.
In order to solve the technical problems, the invention provides a desulfurizing agent, which comprises the following raw materials:
10-30 parts of dehydroabietylamine;
1-4 parts of formaldehyde;
1-2 parts of a surfactant;
1-2 parts of synergist.
Preferably, the desulfurizing agent comprises the following raw materials:
20 parts of dehydroabietylamine;
Formaldehyde 2 parts;
1 part of a surfactant;
1 part of synergistic agent.
Preferably, the surfactant is at least one of nonylphenol polyoxyethylene ether NP-5, nonylphenol polyoxyethylene ether NP-7, nonylphenol polyoxyethylene ether NP-10 and nonylphenol polyoxyethylene ether NP-15.
Preferably, the synergistic agent is at least one of piperazine, N-methyldiethanolamine and sulfolane.
The invention also provides a preparation method of the desulfurizing agent, which comprises the following steps:
(1) Adding dehydroabietylamine into a solvent, and adding formaldehyde aqueous solution to react for 2-8 hours under the stirring condition to obtain a triazine modifier;
(2) And stirring and mixing the triazine modifier, the surfactant and the synergist uniformly to obtain the desulfurizing agent.
Preferably, the reaction process of the step (1) is as follows:
。
preferably, the solvent in the step (1) is ethanol, the adding rate of the formaldehyde aqueous solution is 1-5 mL/min, and the reaction temperature is 30-60 ℃.
Preferably, the stirring and mixing temperature in the step (2) is 10-30 ℃, and the stirring and mixing time is 0.5-1h.
The technical scheme of the invention has the following advantages:
1. The desulfurizing agent provided by the invention takes the dehydroabietylamine as a natural derivative as a raw material, avoids using petroleum-based raw materials, and is environment-friendly;
2. According to the preparation method of the desulfurizing agent, the triazine modifier is prepared by reacting the dehydroabietylamine which is a natural derivative with formaldehyde, and is further mixed with the surfactant and the synergist to obtain the desulfurizing agent, so that the desulfurizing agent still has a good desulfurizing effect at a high temperature of 90 ℃, and has the advantages of high desulfurizing speed, high efficiency and complete desulfurizing within 60 minutes; meanwhile, the reaction process is simple, and can be applied to industrial production.
Detailed Description
The following examples are provided for a better understanding of the present invention and are not limited to the preferred embodiments described herein, but are not intended to limit the scope of the invention, any product which is the same or similar to the present invention, whether in light of the present teachings or in combination with other prior art features, falls within the scope of the present invention.
The specific experimental procedures or conditions are not noted in the examples and may be followed by the operations or conditions of conventional experimental procedures described in the literature in this field. The reagents or apparatus used were conventional reagent products commercially available without the manufacturer's knowledge.
Example 1
A preparation method of a desulfurizing agent comprises the following steps:
(1) 200g dehydroabietylamine is added into 500mL of ethanol, stirred at 40 ℃, 54g of 37wt% formaldehyde aqueous solution is added dropwise at the speed of 2mL/min, and the reaction is carried out for 4 hours at 40 ℃ to obtain a triazine modifier, wherein the reaction process is as follows:
；
(2) And uniformly mixing the obtained triazine modifier, 10g of nonylphenol polyoxyethylene ether NP-10 and 10g of piperazine at 20 ℃ for 0.5h, and obtaining the desulfurizing agent.
Example 2
A preparation method of a desulfurizing agent comprises the following steps:
(1) 300g dehydroabietylamine is added into 700mL of ethanol, stirred at 60 ℃, 108g of 37wt% formaldehyde aqueous solution is added dropwise at the speed of 5mL/min, and the reaction is carried out for 8 hours at 60 ℃ to obtain a triazine modifier, wherein the reaction process is as follows:
；
(2) And stirring the obtained triazine modifier, 20g of nonylphenol polyoxyethylene ether NP-10 and 20g of N-methyldiethanolamine at 30 ℃ for 1h, and uniformly mixing to obtain the desulfurizing agent.
Example 3
A preparation method of a desulfurizing agent comprises the following steps:
(1) 100g dehydroabietylamine is added into 200mL of ethanol, stirred at 30 ℃, 27g of 37wt% formaldehyde aqueous solution is added dropwise at the speed of 1mL/min, and the reaction is carried out for 2 hours at 30 ℃ to obtain a triazine modifier, wherein the reaction process is as follows:
；
(2) And stirring the obtained triazine modifier, 10g of nonylphenol polyoxyethylene ether NP-10 and 10g of N-methyldiethanolamine at 10 ℃ for 0.5h, and uniformly mixing to obtain the desulfurizing agent.
The desulfurizing agents prepared in examples 1-3 and the conventional 1,3, 5-trihydroxyethyl hexahydros-triazine desulfurizing agent in the prior art are added into a crude oil gathering and transportation system according to the addition amount of 200mg/L, and the concentration of hydrogen sulfide contained in crude oil with different standing time (10 min, 30min and 60 min) is tested as shown in table 1.
TABLE 1 Hydrogen sulfide concentration at various rest times
TABLE 1 Hydrogen sulfide concentration at various rest times
| Test conditions | Example 1 | Example 2 | Example 3 | 1,3, 5-Trihydroxyethyl hexahydro s-triazine desulfurizing agent |
| Concentration of Hydrogen sulfide before treatment (ppm) | 5450 | 5450 | 5450 | 5450 |
| Concentration of Hydrogen sulfide (ppm) after 10min of treatment | 10 | 12 | 15 | 70 |
| Concentration of Hydrogen sulfide (ppm) after 30min of treatment | 2 | 3 | 3 | 25 |
| Concentration of Hydrogen sulfide (ppm) after 60min of treatment | 0 | 0 | 0 | 12 |
As can be seen from Table 1, the desulfurizing agent prepared by the application has the advantages of high desulfurizing speed, good desulfurizing effect and complete desulfurizing within 60 minutes compared with the conventional 1,3, 5-trihydroxyethyl hexahydros-triazine desulfurizing agent in the prior art.
The desulfurizing agents prepared in examples 1-3 and the conventional 1,3, 5-trihydroxyethyl hexahydro s-triazine desulfurizing agent in the prior art are added into a crude oil gathering and transporting system according to the addition amount of 200mg/L, different temperatures are set, and the concentration of hydrogen sulfide contained in crude oil at the different temperatures is tested as shown in table 2.
TABLE 2 Hydrogen sulfide concentration at different temperatures
TABLE 2 Hydrogen sulfide concentration at different temperatures
| Test conditions | Example 1 | Example 2 | Example 3 | 1,3, 5-Trihydroxyethyl hexahydro s-triazine desulfurizing agent |
| Before treatment (ppm) | 5450 | 5450 | 5450 | 5450 |
| Concentration of Hydrogen sulfide (ppm) after 60min of treatment at 30 ℃ | 0 | 0 | 0 | 22 |
| Concentration of Hydrogen sulfide (ppm) after 60min of treatment at 60 ℃ | 0 | 0 | 0 | 35 |
| Concentration of Hydrogen sulfide (ppm) after 60min of treatment at 90 ℃ | 0 | 0 | 0 | 48 |
As can be seen from Table 2, the desulfurizing agent prepared by the application has better high temperature resistance and better desulfurizing effect at the high temperature of 90 ℃ compared with the 1,3, 5-trihydroxyethyl hexahydro s-triazine desulfurizing agent commonly used in the prior art.
The triazine modifier is prepared by reacting dehydroabietylamine with formaldehyde, and is further mixed with a surfactant and a synergist to obtain the desulfurizer, and the obtained desulfurizer can be applied to high-temperature desulfurization, because the triazine modifier has a ternary phenanthrene structure, on one hand, has excellent solubility in crude oil, and on the other hand, the ternary phenanthrene structure enables the triazine modifier to have high-temperature resistance, so that the triazine modifier is mixed with the surfactant and the synergist to obtain the composite desulfurizer, has good desulfurization effect at a high temperature of 90 ℃, and has high desulfurization speed and efficiency, and can completely desulfurize within 60 minutes.
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. While still being apparent from variations or modifications that may be made by those skilled in the art are within the scope of the invention.
Claims (3)
1. The desulfurizing agent is characterized by comprising the following raw materials:
10-30 parts of dehydroabietylamine;
1-4 parts of formaldehyde;
1-2 parts of a surfactant;
1-2 parts of synergist;
the surfactant is at least one of nonylphenol polyoxyethylene ether NP-5, nonylphenol polyoxyethylene ether NP-7, nonylphenol polyoxyethylene ether NP-10 and nonylphenol polyoxyethylene ether NP-15;
The synergistic agent is at least one of piperazine, N-methyldiethanolamine and sulfolane;
the preparation method of the desulfurizing agent comprises the following steps:
(1) Adding dehydroabietylamine into a solvent, and adding formaldehyde aqueous solution to react for 2-8 hours under the stirring condition to obtain a triazine modifier;
(2) Stirring and mixing the triazine modifier, the surfactant and the synergist uniformly to obtain a desulfurizing agent;
The reaction process of the step (1) is as follows:
；
the solvent in the step (1) is ethanol, the adding rate of the formaldehyde aqueous solution is 1-5 mL/min, and the reaction temperature is 30-60 ℃.
2. The desulfurizing agent according to claim 1, which comprises the following raw materials:
20 parts of dehydroabietylamine;
Formaldehyde 2 parts;
1 part of a surfactant;
1 part of synergistic agent.
3. The desulfurizing agent according to claim 1, wherein the stirring and mixing temperature in the step (2) is 10 to 30 ℃ and the stirring and mixing time is 0.5 to 1h.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2593508A1 (en) * | 2006-07-05 | 2008-01-05 | Georgia-Pacific Resins, Inc. | Amine-aldehyde resins and uses thereof in separation processes |
| CN101333454A (en) * | 2008-07-30 | 2008-12-31 | 浙江工业大学 | Desulphurization process of gasoline by catalytic oxidation and adsorption |
| CN102093907A (en) * | 2009-12-11 | 2011-06-15 | 中国石油天然气股份有限公司 | Method for desulphurizing gasoline |
| CN102580470A (en) * | 2012-02-20 | 2012-07-18 | 西南石油大学 | Desulfurizing agent for purifying natural gas and petrochemical gas |
| JP2017148710A (en) * | 2016-02-23 | 2017-08-31 | 新日鐵住金株式会社 | Wet type desulfurization method from hydrogen sulfide containing gas |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6683020B2 (en) * | 2000-07-21 | 2004-01-27 | Exxonmobil Research And Engineering Company | Naphthene ring opening over an iridium ring opening catalyst |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2593508A1 (en) * | 2006-07-05 | 2008-01-05 | Georgia-Pacific Resins, Inc. | Amine-aldehyde resins and uses thereof in separation processes |
| CN101333454A (en) * | 2008-07-30 | 2008-12-31 | 浙江工业大学 | Desulphurization process of gasoline by catalytic oxidation and adsorption |
| CN102093907A (en) * | 2009-12-11 | 2011-06-15 | 中国石油天然气股份有限公司 | Method for desulphurizing gasoline |
| CN102580470A (en) * | 2012-02-20 | 2012-07-18 | 西南石油大学 | Desulfurizing agent for purifying natural gas and petrochemical gas |
| JP2017148710A (en) * | 2016-02-23 | 2017-08-31 | 新日鐵住金株式会社 | Wet type desulfurization method from hydrogen sulfide containing gas |
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