CN101358145A - Extractive agent for depriving sulphide in C9 fuel oil and depriving method - Google Patents
Extractive agent for depriving sulphide in C9 fuel oil and depriving method Download PDFInfo
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Abstract
The present invention relates to extractant used to remove sulfide in C9 fuel oil and a removing method. The extractant comprises N, N-dimethylformamide, dimethyl sulfoxide, N-methyl pyrrolidine, triethylene glycol, diethylene glycol, acetonitrile, methanol, ethanol or aqueous single-component solvent or double-component mixed solvent or three-component mixed solvent: the mass percentage composition of each component of the extractant is as follows: a first component: 70 percent to 100 percent; a second component: 0 percent to 30 percent; and a third component: 0 percent to 20 percent. According to a mass portion ratio which is 2 : 1 to 1 : 2, the C9 fuel oil and the extractant are blended, the extraction temperature is between 20 DEG C and 70 DEG C, the extraction time lasts 10 minutes to 60 minutes, the constant-temperature quiescence time lasts 20 minutes to 40 minutes, and after extraction, the C9 fuel oil phase is washed by water in order to wash out the solvent, so that desulfurized fuel oil is produced. The used extractant can take account of both the yield and desulfurization rate of the C9 fuel oil, the desulfurization rate can reach 58 percent, and the yield can reduce the pressure of the subsequent recovery of the solvent.
Description
Technical field
The present invention relates to abstraction desulfurization technology, particularly relate to the extraction agent and the removal methods that are used for removing C 9 fuel oil sulfide.
Background technology
Unsaturated hydrocarbons and alkyl benzenes such as the vinylbenzene in the C 9 fraction, dicyclopentadiene, Vinyl toluene, indenes, be fit to produce the aromatic hydrocarbons petroleum resin, while by-product aromatic solvent naphtha, the aromatic hydrocarbons petroleum resin can be widely used in rubber batching, seal gum, solvent-based adhesive, coating, paint, printing-ink, anti-water pref and concrete curing composition etc., extensive market.At present, the by-product cracking heavy aromatics C 9 fraction of China's ethylene unit is most of to be used for the production of petroleum resin on a small quantity as fuel, and economic benefit is not high.Its major cause is that the C 9 fuel oil sulphur content is too high and cause its product stink heavier, influences its quality and application.The method of oil fuel being carried out desulfurization mainly contains: catalytic desulfurhydrogenation, catalytic cracking and desulfurizing, oxidation-extraction desulfurization, solvent extraction desulfurization, biocatalytic desulfurization, adsorption desulfurize, film desulfurization and photochemical catalysis desulfurization etc.The domestic method of hydrotreating that generally adopts carries out the desulfurization processing to oil fuel, hydrodesulfurization has the yield of gasoline height, low-sulfur content advantage, but this method facility investment is big, the operational condition harshness, the hydrogen consumption is big, and process cost is higher, in addition hydrogenating desulfurization the time the most of alkene in the oil product also by saturated.The exploitation of non-in recent years hydrogenating desulfurization technology more and more comes into one's own, and has obtained some achievements at present, mainly comprises absorption method desulfurization, oxidation desulfurization, biological desulphurization and abstraction desulfurization etc.In these methods, extraction and distillation technology has himself advantage.Select the S-contained substance in the suitable extraction solvent dissolved fuel oil for use, raw material or intermediate product that the sulfide that is extracted out can be used as Chemicals use, and fundamentally control sulphur pollution and stink and pollute.The most attracting feature of abstraction desulfurization is to operate under low temperature, low pressure, and equipment is not had particular requirement yet, thereby is easy to use in Petrochemical Enterprises.And at effective desulfurization de-odorised simultaneously, avoided the reduction of the saturated and gasoline octane rating of alkene.Compare with other technology, have greater advantage economically, be fit to China's national situation, have the applications well prospect.
Adopt nitrogenous organic solvent N-methyl-2-pyrrolidone in the U.S. Pat 5494572 respectively, 1,3-dimethyl-2-miaow quinoline ketone, N, dinethylformamide, dimethyl sulfoxide (DMSO) is that extraction agent removes the organic sulfide thiophene in the oil fuel and the derivative of thionaphthene.
Use molecular weight less than 400 polyalkylene glycol in the U.S. Pat 5582714, as glycol ether, the Tetraglycol 99 extraction removes the sulfide in the FCC gasoline.FCC gasoline contacts in extraction tower with extraction agent, and sweet gasoline is discharged by cat head, obtains product gasoline through washing; The solvent phase of the sulfur compound that obtains at the bottom of the tower flashes off lightweight oil earlier, and the stripping that reduces pressure again separates the extraction oil that obtains solvent and enrichment sulfide.
Be extraction agent with the poly(oxyethylene glycol) 400 in the Chinese patent 01136251.0, adopt multi-stage counter current extraction to remove sulfide in the catalytically cracked gasoline.
United States Patent (USP) 6623627 is divided into three parts with gasoline fraction (32～425 ℉), and low boiler cut mainly contains thio-alcohol sulfide in (100～180), uses alkaline aqueous solution to remove, and catalyzer is a metal phthalocyanine compound; Mainly contain thiophene-type sulfide in the middle runnings (100～300 ℉), adopt solvent extraction to remove, extraction agent is a tetramethylene sulfone, furfural, N-formyloxy morpholine, N, N-dimethyl sulfoxide (DMSO), N-methyl-2-pyrrolidone; High boiling fraction (150～425 ℉) adopts catalytic desulfurhydrogenation.
The report of still unmatchful C 9 fuel oil desulfurization at present.Institute's sulfur compound is mainly high carbon number mercaptan in the C 9 fuel oil, thioether and thiophene-based polarity sulfide, therefore can utilize the similar compatibility principle to select polar solvent to extract polarity sulfide, but the composition of C 9 fuel oil and gasoline, the diesel oil difference, be used for gasoline, the extraction agent of diesel oil abstraction desulfurization also is not suitable for the C 9 fuel oil desulfurization, aromaticity content is higher in the C 9 fuel oil, some extraction agents are because excessive and can't use with the mutual solubility of C 9 fuel oil, so key issue also is the difficult point problem is that solvent for use is as far as possible little with the mutual solubility of oil, make in the extraction phase oil-contg less relatively, thereby can improve the yield of C 9 fuel oil, also can reduce simultaneously the expense of follow-up solvent recuperation, the raising of desulfurization degree can realize by multi-stage solvent extraction.Therefore, we are common as the research index with the yield and the desulfurization degree of C 9 fuel oil.
Summary of the invention
The objective of the invention is to propose the method that sulfide in the C 9 fuel oil is removed in a kind of solvent extraction, this method can be taken into account the yield and the desulfurization degree of C 9 fuel oil.
Technical scheme of the present invention is as follows:
The extraction agent that is used for removing C 9 fuel oil sulfide of the present invention, comprise N, the one-part solvent of dinethylformamide, dimethyl sulfoxide (DMSO), N-Methyl pyrrolidone, triethylene glycol, Diethylene Glycol, acetonitrile, methyl alcohol, ethanol or water or two component mixed solvents or three component mixed solvents: the quality percentage composition of its each component is as follows:
First group: 70～100%,
Second group: 0～30%,
The 3rd group: 0～20%.
The extraction agent that is used for removing C 9 fuel oil sulfide of the present invention, preferred ingredient and quality percentage composition are as follows:
First group 75～85%,
Second group 6～20%,
The 3rd group 5～10%.
Extraction agent of the present invention is used for removing the method for C 9 fuel oil sulfide, be to be configuration in 2: 1～1: 2 by the massfraction ratio with C 9 fuel oil and extraction agent, extraction temperature is 20～70 ℃, 10～60 minutes extraction time, constant temperature time of repose 20～40 minutes, extraction back C 9 fuel oil washes with water mutually solvent is washed out, and has both got desulfurized fuel oil.
Described C 9 fuel oil is from cracking of ethylene.
The C 9 fuel oil boiling range is mainly dicyclopentadiene, alkylbenzene, polynuclear hydrocarbon and indane at 90～220 ℃, and wherein alkylbenzene content is 35～45%, and sulphur content is 120～180ppm.
Effect of the present invention is: the present invention proposes to remove the extraction agent and the removal methods of sulfide in the C 9 fuel oil, and used extraction agent can be taken into account the yield and the desulfurization degree of C 9 fuel oil, and desulfurization degree can reach 58%, and yield improves the pressure that can alleviate follow-up solvent recuperation.
Embodiment
Embodiment 1:
20g C 9 fuel oil (composition sees Table 1) is mixed in the 250ml Erlenmeyer flask with 20g solvent Diethylene Glycol, 25 ℃ of constant temperature stir 30min, change over to then and leave standstill 30min in the separating funnel, clear layering, the upper strata is an oil phase, after washing, weigh, calculated yield is 91.8%, and the microcoulomb method is analyzed the oil phase total sulfur content, and sulphur content is 147ppm before the desulfurization, sulphur content is 135ppm after the desulfurization, and desulfurization degree is 8.2%.
Table 1 C 9 fuel oil is formed
| Component | Content wt% | Component | Content wt% | Component | Content wt% |
| Cyclopentenes | 0.548 | Isopropyl benzene | 0.777 | C 10H 16Polynaphthene | 3.454 |
| Pentamethylene | 0.853 | Propylbenzene | 3.819 | Indane | 8.454 |
| The 4-methyl cyclopentene | 0.815 | M-methyl ethylbenzene | 10.606 | Indenes | 0.877 |
| The propyl group cyclopentenes | 0.072 | P-methyl-ethylbenzene | 4.093 | The dihydro dicyclopentadiene | 10.247 |
| Ethylbenzene | 5.597 | 1,3, the 5-trimethylbenzene | 2.169 | The dicyclo pentane | 3.157 |
| Between p-Xylol | 0.349 | O-methylethylbenzene | 4.827 | C 11H 16Polynaphthene | 6.979 |
| O-Xylol | 2.650 | 1,2, the 4-trimethylbenzene | 6.534 | Other unknown component | 23.12 |
Embodiment 2:
The 20g C 9 fuel oil is mixed in the 250ml Erlenmeyer flask with solvent, moisture 10wt% in the solvent, all the other are N, dinethylformamide, oil was respectively 1: 12: 1 with the mass ratio of solvent, 1: 2, stir 30min in 25 ℃ of constant temperature, change over to then and leave standstill 30min in the separating funnel, clear layering, the upper strata is an oil phase, weighs calculated yield after washing, the microcoulomb method is analyzed the oil phase total sulfur content, calculates desulfurization degree.The results are shown in Table 2, and it can be seen from the table, finish mass ratio 2: 1～1: 2 can reach the desulfurization degree more than 30%.
The different finish quality of table 2 are than C 9 fuel oil abstraction desulfurization experimental result
| Finish mass ratio g/g | Sulphur content ppm before the desulfurization | Sulphur content ppm after the desulfurization | Desulfurization degree % | Rate of recovery % |
| 2∶1 | 144 | 98 | 31.9 | 116 |
| 1∶1 | 144 | 83 | 42.4 | 101 |
| 1∶2 | 144 | 91 | 36.1 | 51.3 |
Embodiment 3:
The 20g C 9 fuel oil is mixed in the 250ml Erlenmeyer flask with solvent, moisture 10wt% in the solvent, all the other are N, dinethylformamide, oil was respectively 1: 1 with the mass ratio of solvent, respectively at 20 ℃, 30 ℃, 40 ℃, 50 ℃, 60 ℃, 70 ℃ of constant temperature stir 30min, change over to then and leave standstill 30min in the separating funnel, clear layering, upper strata are oil phase, weigh after washing, calculated yield, the microcoulomb method is analyzed the oil phase total sulfur content, calculates desulfurization degree.The results are shown in Table 3, and it can be seen from the table, extraction temperature is 20 ℃, and 30 ℃, 40 ℃, 50 ℃, 60 ℃, in the time of 70 ℃, the desulfurization degree and the rate of recovery are all relatively good.
C 9 fuel oil abstraction desulfurization experimental result under table 3 differing temps
| Extraction temperature ℃ | Sulphur content ppm before the desulfurization | Sulphur content ppm after the desulfurization | Desulfurization degree % | Rate of recovery % |
| 20 | 152 | 99 | 34.9 | 103 |
| 30 | 152 | 98 | 35.5 | 96.7 |
| 40 | 152 | 94 | 38.2 | 100 |
| 50 | 152 | 90 | 40.8 | 99.8 |
| 60 | 147 | 83 | 43.5 | 98.1 |
| 70 | 147 | 90 | 38.8 | 102 |
Embodiment 4:
The 20g C 9 fuel oil is mixed in the 250ml Erlenmeyer flask with solvent, water content is listed in the table 4 in the solvent, and all the other are acetonitrile, and the finish mass ratio is 1: 1,30 ℃ of constant temperature stir extraction 30min, change over to then and leave standstill 30min in the separating funnel, clear layering, lower floor is an oil phase, after washing, weigh, calculated yield, the microcoulomb method is analyzed the oil phase total sulfur content, calculates desulfurization degree.The results are shown in Table 4, and it can be seen from the table, water content improves can improve the extraction yield.
Table 4 C 9 fuel oil different moisture content acetonitrile solution abstraction desulfurization experimental result
| Water content wt% | Sulphur content ppm before the desulfurization | Sulphur content ppm after the desulfurization | Desulfurization degree % | Rate of recovery % |
| 6.2 | 166 | 131 | 21.0 | 45.8 |
| 10.6 | 166 | 134 | 19.3 | 64.6 |
| 12.3 | 166 | 136 | 18.1 | 67.3 |
| 14.1 | 166 | 139 | 16.3 | 70.2 |
| 16.3 | 166 | 137 | 17.5 | 72.0 |
| 21.0 | 166 | 146 | 12.0 | 78.6 |
| 24.0 | 166 | 147 | 11.4 | 82.1 |
| 30.0 | 166 | 149 | 10.2 | 92.2 |
Embodiment 5:
The 20g C 9 fuel oil is mixed in the 250ml Erlenmeyer flask with solvent, contain acetonitrile, water, Diethylene Glycol in the solvent, wherein water, the Diethylene Glycol massfraction in solvent is listed in the table 5, all the other are acetonitrile, the finish mass ratio is 1: 1, and 30 ℃ of constant temperature stir 30min, change over to then and leave standstill 30min in the separating funnel, clear layering, lower floor is an oil phase, weighs calculated yield after washing, analyze the sulphur content of oil phase, calculate desulfurization degree.The results are shown in Table 5, it can be seen from the table, can further improve sweetening effectiveness with other solvent complexes such as Diethylene Glycol, and behind the composite Diethylene Glycol of the acetonitrile solution of water content 10wt%, desulfurization degree can bring up to 51.6% by 19.3%, and yield also has raising simultaneously.
The composite extraction agent desulfurization of table 5 result
| 15 | 151 | 82 | 45.7 | 87.8 |
| 20 | 151 | 91 | 39.7 | 90.4 |
The present invention open and the extraction agent and the removal methods that are used for removing C 9 fuel oil sulfide that propose, those skilled in the art can be by using for reference this paper content, and links such as appropriate change raw material, processing parameter realize.Solvent of the present invention and method are described by preferred embodiment, person skilled obviously can be in not breaking away from content of the present invention, spirit and scope to method as herein described with product is changed or suitably change and combination, realize the technology of the present invention.Special needs to be pointed out is, the replacement that all are similar and change apparent to those skilled in the artly, they are regarded as being included in spirit of the present invention, scope and the content.
Claims (5)
1. extraction agent that is used for removing C 9 fuel oil sulfide, it is characterized in that comprising N, the one-part solvent of dinethylformamide, dimethyl sulfoxide (DMSO), N-Methyl pyrrolidone, triethylene glycol, Diethylene Glycol, acetonitrile, methyl alcohol, ethanol or water or two component mixed solvents or three component mixed solvents: the quality percentage composition of its each component is as follows:
First group: 70～100%,
Second group: 0～30%,
The 3rd group: 0～20%.
2. the extraction agent that is used for removing C 9 fuel oil sulfide as claimed in claim 1 is characterized in that described
First group 75～85%,
Second group 6～20%,
The 3rd group 5～10%.
3. claim 1 or 2 extraction agent are used for removing the method for C 9 fuel oil sulfide, it is characterized in that be 2: 1～1: 2 configuration with extraction agent by the massfraction ratio with C 9 fuel oil, extraction temperature is 20～70 ℃, 10～60 minutes extraction time, constant temperature time of repose 20～40 minutes, extraction back C 9 fuel oil phase water washes out solvent, has both got desulfurized fuel oil.
4. method as claimed in claim 3 is characterized in that described C 9 fuel oil is from cracking of ethylene.
5. method as claimed in claim 3 is characterized in that described C 9 fuel oil boiling range at 90～220 ℃, is mainly dicyclopentadiene, alkylbenzene, polynuclear hydrocarbon and indane, and wherein alkylbenzene content is 35～45%, and sulphur content is 120～180ppm.
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| CN105296000A (en) * | 2015-09-30 | 2016-02-03 | 中国石油大学(北京) | Coupling method of catalytic cracking gasoline desulfurization |
| CN105296000B (en) * | 2015-09-30 | 2017-07-11 | 中国石油大学(北京) | A kind of coupling process of catalytically cracked gasoline desulfurization |
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