CN104087336A - Method for removing sulfide from oil product by using choline chloride/oxalic acid type eutectic solvent by virtue of oxidation-extraction integrated process - Google Patents

Method for removing sulfide from oil product by using choline chloride/oxalic acid type eutectic solvent by virtue of oxidation-extraction integrated process Download PDF

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CN104087336A
CN104087336A CN201410337332.9A CN201410337332A CN104087336A CN 104087336 A CN104087336 A CN 104087336A CN 201410337332 A CN201410337332 A CN 201410337332A CN 104087336 A CN104087336 A CN 104087336A
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oxalic acid
choline chloride
eutectic solvent
oil
extraction
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赵荣祥
李秀萍
李佳慧
胡嘉
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Liaoning Shihua University
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Liaoning Shihua University
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Abstract

The invention belongs to the field of oil product sulfide removal, and in particular relates to a method for removing sulfide from an oil product by using a choline chloride/oxalic acid type eutectic solvent by virtue of an oxidation-extraction integrated process. The method is implemented according to the following steps: (1) synthesis of the choline chloride/oxalic acid eutectic solvent: weighing choline chloride and oxalic acid, and stirring until a transparent solution is formed to obtain the choline chloride/oxalic acid eutectic solvent; (2) a desulfurization process: weighing dibenzothiophene, and dissolving into normal octane to prepare simulated oil; weighing the simulated oil and the choline chloride/oxalic acid eutectic solvent; adding hydrogen peroxide, stirring, and cooling to room temperature; performing static lamination in a separating funnel, and absorbing a sample in an upper-layer oil phase; and measuring the sulfur content, and calculating the desulfurization rate. According to the method disclosed by the invention, in the preparation process, an adopted catalyst serves as both the catalyst and an extraction agent, thus the production cost is reduced, and the desulfurization process is simplified.

Description

A kind of method that adopts choline chloride 60/oxalic acid type eutectic solvent oxidation-extraction one method to remove oil product medium sulphide content
Technical field
The invention belongs to oil product sulfide and remove field, relate in particular to a kind of method that adopts choline chloride 60/oxalic acid type eutectic solvent oxidation-extraction one method to remove oil product medium sulphide content.
Background technology
Fast development along with car industry, the sulfide that vehicle fuel burning produces is also on the rise to the pollution of environment, sulphur content standard [the YAZU K of strict gasoline and diesel oil has been formulated in countries in the world and area in succession, YAMAMOTO Y, FURUYA T, MIKI K, UKEGAWA K. Oxidation of Dibenzothiophenes in an Organic Biphasic System and Its Application to Oxidative Desulfurization of Light Oil[J] Energy Fuels, 2001,15:1535-1536.]。Industrial common employing hydrogenating desulfurization (HDS) removes the sulfide in petrol and diesel oil, but for thiophene and derivatives due to Existential Space steric effect, sweetening effectiveness is poor, in order to reach the object of deep desulfuration, must propose higher requirement to reaction conditions and catalyzer, and then cause petrol and diesel oil cost to increase.Oxidation sweetening (ODS) is the new technology of the production super low sulfur fuel that gets up of development in recent years, its reaction conditions is gentle, does not expend hydrogen, and facility investment is less, the benzothiophenes that shortening is difficult to remove has higher desulfuration efficiency, has good application prospect.
Ionic liquid (IL) is green solvent and the functional materials of people's common concern in recent years.Ionic liquid has that steam forces down, non-combustible, easy recovery, the advantage such as can be recycled.In recent years, scholars adopt ionic liquid to obtain good effect as extraction agent and the catalyzer of sulfide.Yet there is the shortcomings such as building-up process complexity, purification difficult, cost are higher in conventional ionic liquid, has limited its heavy industrialization application and development.2003, [ the ABBOTT A P such as Abbott, CAPPER G, DAVIES D L, RASHEED R K, TAMBYRAJAH V. Novel solvent properties of choline chloride/urea mixtures[J] .Chem. Commun., 2003: 70-71 ] found first a kind of solvent-eutectic solvent of the excellent in physical and chemical performance being formed by quaternary ammonium salt and amide compound.The physicochemical property of eutectic solvent are extremely similar to ionic liquid, therefore also there is people that it is classified as to a class novel ion liquid or ionic liquid analogue [Wei Lu, Fan Youjun. eutectic solvent and applied research progress [J] thereof. chemistry circular, 2011,74(4): 333-339 WEI Lu, FAN You-jun. Progress of Deep Eutectic Solvents and Their Applications [J]. CHEMISTRY, 2011,74(4): 333-339].This solvent nontoxicity, biodegradable, and building-up process atom utilization reaches 100%, is a kind of novel green solvent.At present, eutectic solvent has caused countries in the world investigators' extensive attention, and demonstrates good application prospect in fields such as sepn process, chemical reaction, functional materials and electrochemistry.In recent years, eutectic solvent is applied in desulfurizing oil field.[LI F T, LIU Y, SUN Z M, CHEN L, ZHAO D S, LIU R, the KOU C. Deep Extractive Desulfurization of Gasoline with xEt such as Li 3nHCl 3feCl 3ionic Liquids[J]. Energ. Fuels, 2010,24:4285-4289] by Triethylammonium chloride and the synthetic eutectic solvent of iron(ic) chloride and investigated its abstraction desulfurization effect, result shows, its single percentage extraction can reach 87%.[the Li C P such as Lee, Li D, Zou S S, et al. Extraction desulfurization process of fuels with ammonium-based deep eutectic solvents[J]. Green Chem. 2013,15:2793-2799] comparatively systematic study a series of eutectic solvent abstraction desulfurization effects, show that the eutectic solvent single percentage extraction being formed by tetrabutylammonium chloride and polyoxyethylene glycol can reach 82%.Can find out, the sulfide that adopts eutectic solvent to remove in oil product has good application prospect, is necessary it to further investigate.
Summary of the invention
The object of the present invention is to provide a kind of method that adopts choline chloride 60/oxalic acid type eutectic solvent to remove oil product medium sulphide content.In this desulfurization system, choline chloride 60/oxalic acid is catalyzer and extraction agent, has not only reduced production cost but also from source, alleviated the pollution to environment.
For solving the problems of the technologies described above, the present invention realizes like this.
Adopt choline chloride 60/oxalic acid type eutectic solvent oxidation-extraction one method to remove a method for oil product medium sulphide content, can implement as follows.
(1) choline chloride 60/oxalic acid eutectic solvent is synthetic: take choline chloride 60 and oxalic acid, stir until formation clear solution can obtain choline chloride 60/oxalic acid eutectic solvent.
(2) sweetening process: take dibenzothiophene and be dissolved in octane, be made into simulated oil; Take simulated oil and choline chloride 60/oxalic acid eutectic solvent; Add hydrogen peroxide, stir, be cooled to room temperature; Static layering in separating funnel, draws sample in upper oil phase; Measure sulphur content and calculate desulfurization degree.
As a kind of preferred version, in step of the present invention (1), the mol ratio of choline chloride 60 and oxalic acid is 1:1.
Further, in step of the present invention (1), whipping temp is 100 ℃.
Further, in step of the present invention (2), the volume ratio of described simulated oil and choline chloride 60/oxalic acid eutectic solvent is 5:4.
Further, in step of the present invention (2), the add-on of hydrogen peroxide is 0.1~0.5 mL.
Further, in step of the present invention (2), temperature of reaction is 40~60 ℃.
Further, in step of the present invention (2), the reaction times is 1~180 min.
The present invention's choline chloride 60/oxalic acid used synthesis mechanism.
In preparation process of the present invention, all reagent is commerical prod, without loaded down with trivial details preparation.In preparation process of the present invention, the catalyzer adopting is catalyzer and extraction agent, thereby has reduced production cost, has simplified the program of desulfurization.In addition, the present invention has obtained good balance between raising desulfurization degree and enhancing environmental protection efficacy.
Accompanying drawing explanation
Below in conjunction with the drawings and specific embodiments, the invention will be further described.Protection scope of the present invention is not only confined to the statement of following content.
Fig. 1 is the gas-chromatography spectrogram of oil phase in sweetening process of the present invention.
Embodiment
Adopt choline chloride 60/oxalic acid type eutectic solvent oxidation-extraction one method to remove the method for oil product medium sulphide content, implement as follows.
(1) choline chloride 60/oxalic acid eutectic solvent is synthetic: take choline chloride 60 (C 5h 14clNO) and oxalic acid (C 2h 2o 42H 2o), stir until formation clear solution can obtain choline chloride 60/oxalic acid eutectic solvent (C 5h 14clNOH 2c 2o 4).
(2) sweetening process: take dibenzothiophene (DBT) and be dissolved in octane, be made into simulated oil; Take simulated oil and choline chloride 60/oxalic acid eutectic solvent; Add hydrogen peroxide, stir, be cooled to room temperature; Static layering in separating funnel, draws sample in upper oil phase; Measure sulphur content and calculate desulfurization degree.
In step of the present invention (1), the mol ratio of choline chloride 60 and oxalic acid is 1:1; Whipping temp is 100 ℃.
In step of the present invention (2), the volume ratio of described simulated oil and choline chloride 60/oxalic acid eutectic solvent is 5:4; The add-on of hydrogen peroxide is 0.1~0.5 mL; Temperature of reaction is 40~60 ℃; Reaction times is 1~180 min.
embodiment 1.
Take a certain amount of dibenzothiophene (DBT) and be dissolved in octane, be made into the simulated oil that sulphur content is 500ppm.Take 10 mL simulated oil, 8 mL choline chloride 60/oxalic acid eutectic solvents, in 50mL Erlenmeyer flask, add the H of 0.1 mL 2o 2.At 40 ℃, stir after 180 min, mixture is cooled to room temperature, static layering in separating funnel, draws sample in upper oil phase, and with WK-2D type Microcoulomb comprehensive analysis instrument, measuring sulphur content and calculate desulfurization degree is 84%.
embodiment 2.
Take a certain amount of dibenzothiophene (DBT) and be dissolved in octane, be made into the simulated oil that sulphur content is 500ppm.Take 10 mL simulated oil, 8 mL choline chloride 60/oxalic acid eutectic solvents, in 50mL Erlenmeyer flask, add the H of 0.2 mL 2o 2.At 40 ℃, stir after 180 min, mixture is cooled to room temperature, static layering in separating funnel, draws sample in upper oil phase, and with WK-2D type Microcoulomb comprehensive analysis instrument, measuring sulphur content and calculate desulfurization degree is 92%.
embodiment 3.
Take a certain amount of dibenzothiophene (DBT) and be dissolved in octane, be made into the simulated oil that sulphur content is 500ppm.Take 10 mL simulated oil, 8 mL choline chloride 60/oxalic acid eutectic solvents, in 50mL Erlenmeyer flask, add the H of 0.3 mL 2o 2.At 40 ℃, stir after 180 min, mixture is cooled to room temperature, static layering in separating funnel, draws sample in upper oil phase, and with WK-2D type Microcoulomb comprehensive analysis instrument, measuring sulphur content and calculate desulfurization degree is 93%.
embodiment 4.
Take a certain amount of dibenzothiophene (DBT) and be dissolved in octane, be made into the simulated oil that sulphur content is 500ppm.Take 10 mL simulated oil, 8 mL choline chloride 60/oxalic acid eutectic solvents, in 50mL Erlenmeyer flask, add the H of 0.4 mL 2o 2.At 40 ℃, stir after 180 min, mixture is cooled to room temperature, static layering in separating funnel, draws sample in upper oil phase, and with WK-2D type Microcoulomb comprehensive analysis instrument, measuring sulphur content and calculate desulfurization degree is 80%.
embodiment 5.
Take a certain amount of dibenzothiophene (DBT) and be dissolved in octane, be made into the simulated oil that sulphur content is 500ppm.Take 10 mL simulated oil, 8 mL choline chloride 60/oxalic acid eutectic solvents, in 50mL Erlenmeyer flask, add the H of 0.3 mL 2o 2.At 50 ℃, stir after 180 min, mixture is cooled to room temperature, static layering in separating funnel, draws sample in upper oil phase, and with WK-2D type Microcoulomb comprehensive analysis instrument, measuring sulphur content and calculate desulfurization degree is 83%.
embodiment 6.
Take a certain amount of dibenzothiophene (DBT) and be dissolved in octane, be made into the simulated oil that sulphur content is 500ppm.Take 10 mL simulated oil, 8 mL choline chloride 60/oxalic acid eutectic solvents, in 50mL Erlenmeyer flask, add the H of 0.3 mL 2o 2.At 50 ℃, stir after 180 min, mixture is cooled to room temperature, static layering in separating funnel, draws sample in upper oil phase, and with WK-2D type Microcoulomb comprehensive analysis instrument, measuring sulphur content and calculate desulfurization degree is 81%.
embodiment 7.
Take a certain amount of dibenzothiophene (DBT) and be dissolved in octane, be made into the simulated oil that sulphur content is 500ppm.Take 10 mL simulated oil, 8 mL choline chloride 60/oxalic acid eutectic solvents, in 50mL Erlenmeyer flask, add the H of 0.3 mL 2o 2.At 40 ℃, stir after 40 min, mixture is cooled to room temperature, static layering in separating funnel, draws sample in upper oil phase, and with WK-2D type Microcoulomb comprehensive analysis instrument, measuring sulphur content and calculate desulfurization degree is 59%.
embodiment 8.
Take a certain amount of dibenzothiophene (DBT) and be dissolved in octane, be made into the simulated oil that sulphur content is 500ppm.Take 10 mL simulated oil, 8 mL choline chloride 60/oxalic acid eutectic solvents, in 50mL Erlenmeyer flask, add the H of 0.3 mL 2o 2.At 40 ℃, stir after 80 min, mixture is cooled to room temperature, static layering in separating funnel, draws sample in upper oil phase, and with WK-2D type Microcoulomb comprehensive analysis instrument, measuring sulphur content and calculate desulfurization degree is 81%.
embodiment 9.
Take a certain amount of dibenzothiophene (DBT) and be dissolved in octane, be made into the simulated oil that sulphur content is 500ppm.Take 10 mL simulated oil, 8 mL choline chloride 60/oxalic acid eutectic solvents, in 50mL Erlenmeyer flask, add the H of 0.3 mL 2o 2.At 40 ℃, stir after 120 min, mixture is cooled to room temperature, static layering in separating funnel, draws sample in upper oil phase, and with WK-2D type Microcoulomb comprehensive analysis instrument, measuring sulphur content and calculate desulfurization degree is 92%.
embodiment 10.
Take a certain amount of dibenzothiophene (DBT) and be dissolved in octane, be made into the simulated oil that sulphur content is 500ppm.Take 10 mL simulated oil, 8 mL choline chloride 60/oxalic acid eutectic solvents, in 50mL Erlenmeyer flask, add the H of 0.3 mL 2o 2.At 40 ℃, stir after 160 min, mixture is cooled to room temperature, static layering in separating funnel, draws sample in upper oil phase, and with WK-2D type Microcoulomb comprehensive analysis instrument, measuring sulphur content and calculate desulfurization degree is 93%.
Be understandably, above about specific descriptions of the present invention, only for being described, the present invention is not limited to the described technical scheme of the embodiment of the present invention, those of ordinary skill in the art is to be understood that, still can modify or be equal to replacement the present invention, to reach identical technique effect; As long as meet, use needs, all within protection scope of the present invention.

Claims (7)

1. adopt choline chloride 60/oxalic acid type eutectic solvent oxidation-extraction one method to remove a method for oil product medium sulphide content, it is characterized in that, implement as follows:
(1) choline chloride 60/oxalic acid eutectic solvent is synthetic: take choline chloride 60 and oxalic acid, stir until formation clear solution can obtain choline chloride 60/oxalic acid eutectic solvent;
(2) sweetening process: take dibenzothiophene and be dissolved in octane, be made into simulated oil; Take simulated oil and choline chloride 60/oxalic acid eutectic solvent; Add hydrogen peroxide, stir, be cooled to room temperature; Static layering in separating funnel, draws sample in upper oil phase; Measure sulphur content and calculate desulfurization degree.
2. employing choline chloride 60/oxalic acid type eutectic solvent oxidation-extraction one method according to claim 1 removes the method for oil product medium sulphide content, it is characterized in that: in described step (1), the mol ratio of choline chloride 60 and oxalic acid is 1:1.
3. employing choline chloride 60/oxalic acid type eutectic solvent oxidation-extraction one method according to claim 2 removes the method for oil product medium sulphide content, it is characterized in that: in described step (1), whipping temp is 100 ℃.
4. employing choline chloride 60/oxalic acid type eutectic solvent oxidation-extraction one method according to claim 3 removes the method for oil product medium sulphide content, it is characterized in that: in described step (2), the volume ratio of described simulated oil and choline chloride 60/oxalic acid eutectic solvent is 5:4.
5. employing choline chloride 60/oxalic acid type eutectic solvent oxidation-extraction one method according to claim 4 removes the method for oil product medium sulphide content, it is characterized in that: in described step (2), the add-on of hydrogen peroxide is 0.1~0.5 mL.
6. employing choline chloride 60/oxalic acid type eutectic solvent oxidation-extraction one method according to claim 5 removes the method for oil product medium sulphide content, it is characterized in that: in described step (2), temperature of reaction is 40~60 ℃.
7. employing choline chloride 60/oxalic acid type eutectic solvent oxidation-extraction one method according to claim 6 removes the method for oil product medium sulphide content, it is characterized in that: in described step (2), the reaction times is 1~180 min.
CN201410337332.9A 2014-07-16 2014-07-16 Method for removing sulfide from oil product by using choline chloride/oxalic acid type eutectic solvent by virtue of oxidation-extraction integrated process Pending CN104087336A (en)

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CN104593056A (en) * 2014-12-01 2015-05-06 烟台大学 Oxidation desulphurization method for diesel oil by using deep eutectic ionic liquid for extraction coupling
CN104774643A (en) * 2015-03-30 2015-07-15 浙江大学 Method for extracting and removing basic nitrides from oil product through nitrogen-free eutectic solvent
CN104887723A (en) * 2015-06-18 2015-09-09 天津理工大学 Method for extracting flavonoids from ginkgo biloba leaves with deep eutectic solvent
CN107541241A (en) * 2017-08-23 2018-01-05 东莞理工学院 A kind of catalysis/extractant for benzothiophene removing and its preparation method and application
CN108179021A (en) * 2017-12-11 2018-06-19 江苏大学 A kind of method of sulfonic group heteropolyacid salt coupling eutectic solvent catalysis fuel desulfuration
CN109593539A (en) * 2018-12-26 2019-04-09 陕西煤业化工集团神木天元化工有限公司 The separation method of phenolic compound in coal tar
CN109794287A (en) * 2019-01-30 2019-05-24 江苏大学 Class graphite ene-type hexagonal boron nitride loads the preparation process and application of the catalyst of eutectic solvent
CN109967126A (en) * 2018-05-30 2019-07-05 吉林省欧发新能源集团有限公司 A kind of temperature control type polyoxometallate oxidation-desulfurizing catalyst and its synthetic method
CN110194965A (en) * 2019-05-22 2019-09-03 江苏大学 A kind of method of three components eutectic solvent catalysis oxidation fuel desulfuration
CN110668506A (en) * 2019-09-29 2020-01-10 昆明理工大学 Method for recycling and regenerating lithium cobaltate from waste lithium ion battery
CN112076784A (en) * 2020-09-25 2020-12-15 辽宁石油化工大学 Preparation method of amphiphilic eutectic solvent supported acid catalyst
CN117587002A (en) * 2023-11-20 2024-02-23 广东海洋大学 Natural chitin carrier immobilized lipase and preparation method and application thereof

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CN104593056A (en) * 2014-12-01 2015-05-06 烟台大学 Oxidation desulphurization method for diesel oil by using deep eutectic ionic liquid for extraction coupling
CN104774643A (en) * 2015-03-30 2015-07-15 浙江大学 Method for extracting and removing basic nitrides from oil product through nitrogen-free eutectic solvent
CN104887723A (en) * 2015-06-18 2015-09-09 天津理工大学 Method for extracting flavonoids from ginkgo biloba leaves with deep eutectic solvent
CN107541241A (en) * 2017-08-23 2018-01-05 东莞理工学院 A kind of catalysis/extractant for benzothiophene removing and its preparation method and application
CN108179021A (en) * 2017-12-11 2018-06-19 江苏大学 A kind of method of sulfonic group heteropolyacid salt coupling eutectic solvent catalysis fuel desulfuration
CN109967126A (en) * 2018-05-30 2019-07-05 吉林省欧发新能源集团有限公司 A kind of temperature control type polyoxometallate oxidation-desulfurizing catalyst and its synthetic method
CN109593539A (en) * 2018-12-26 2019-04-09 陕西煤业化工集团神木天元化工有限公司 The separation method of phenolic compound in coal tar
CN109794287A (en) * 2019-01-30 2019-05-24 江苏大学 Class graphite ene-type hexagonal boron nitride loads the preparation process and application of the catalyst of eutectic solvent
CN109794287B (en) * 2019-01-30 2022-01-11 江苏大学 Preparation process and application of catalyst of graphene-like hexagonal boron nitride loaded eutectic solvent
CN110194965A (en) * 2019-05-22 2019-09-03 江苏大学 A kind of method of three components eutectic solvent catalysis oxidation fuel desulfuration
CN110668506A (en) * 2019-09-29 2020-01-10 昆明理工大学 Method for recycling and regenerating lithium cobaltate from waste lithium ion battery
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Application publication date: 20141008