CN111363587A - Method for separating thioether compounds in petroleum oil products - Google Patents
Method for separating thioether compounds in petroleum oil products Download PDFInfo
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- CN111363587A CN111363587A CN202010222810.7A CN202010222810A CN111363587A CN 111363587 A CN111363587 A CN 111363587A CN 202010222810 A CN202010222810 A CN 202010222810A CN 111363587 A CN111363587 A CN 111363587A
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- organic solvent
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- thioether
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- 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
- C10G53/00—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes
- C10G53/02—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only
- C10G53/08—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only including at least one sorption step
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- 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
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- 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
- C10G2300/1037—Hydrocarbon fractions
-
- 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
- C10G2300/1037—Hydrocarbon fractions
- C10G2300/1048—Middle distillates
- C10G2300/1055—Diesel having a boiling range of about 230 - 330 °C
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- 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
- C10G2300/1037—Hydrocarbon fractions
- C10G2300/1048—Middle distillates
- C10G2300/1059—Gasoil having a boiling range of about 330 - 427 °C
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- 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
- C10G2300/20—Characteristics of the feedstock or the products
- C10G2300/201—Impurities
- C10G2300/202—Heteroatoms content, i.e. S, N, O, P
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- 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
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/04—Diesel oil
Abstract
The invention provides a method for separating thioether compounds in petroleum oil products, which comprises the following steps: dissolving petroleum oil in a first organic solvent; transferring the dissolved oil sample to an alumina column chromatography wetted by a second organic solvent, eluting by a third organic solvent, and collecting the eluent; concentrating the collected eluent, transferring the concentrated eluent into a silica gel column chromatography wetted by a fourth organic solvent, sequentially eluting by a fifth organic solvent to remove saturated hydrocarbon, eluting by a sixth organic solvent to remove thioether, and removing the solvent from a sixth solvent eluent to obtain the thioether component. The method is suitable for separating the thioether compounds in samples such as crude oil, diesel oil fraction, vacuum gas oil fraction and the like, has mild operation conditions, and can completely, efficiently and accurately separate the thioether compounds in petroleum products, particularly low-maturity crude oil.
Description
Technical Field
The invention relates to a method for separating thioether compounds in petroleum products, belonging to the technical field of separation of different compounds in petroleum.
Background
Thioether compounds are a class of organic sulfur-containing compounds commonly found in petroleum. The chemical property of the thioether compounds is more active than that of thiophenes, and the thioether compounds are easily decomposed to generate corrosive gas H in the petroleum refining process2S, which causes equipment corrosion and catalyst poisoning, also causes environmental pollution, and is an important unstable factor in petroleum. In addition, in the field of geochemistry, thioethers may be an important ring connecting original organic matter and thiophenes, and contain important geochemical information.
In the early stage, the sulfides in crude oil are enriched and analyzed by using column chromatography, and the purity of the organic sulfides obtained by the method is not high, and the interference of different sulfides, especially thiophene sulfides, on thioether compounds cannot be eliminated. At present, a chemical means of methyl derivatization and stepwise reduction is usually adopted to separate thioether compounds from crude oil, the method can separate and analyze the thioether compounds with high purity, but the chemical reaction operation is very complicated, the experimental period is as long as more than one week, and side reactions exist in the reaction process, so that the finally separated thioether compounds have difference from the distribution of the thioether compounds in the petroleum.
The prior art lacks a method for simply, quickly and effectively separating the thioether compounds in petroleum.
Disclosure of Invention
The invention aims to provide a method for separating thioether compounds in petroleum, which is used for simply, quickly and effectively separating the thioether compounds in the petroleum.
In order to achieve the above object, the present invention provides a method for separating a thioether compound in a petroleum oil product, comprising:
the method comprises the following steps: dissolving petroleum oil in a first organic solvent;
step two: transferring the dissolved oil sample to an alumina column chromatography wetted by a second organic solvent, eluting by a third organic solvent, and collecting the eluent;
step three: concentrating the collected eluent, transferring the concentrated eluent into a silica gel column chromatography wetted by a fourth organic solvent, sequentially eluting by a fifth organic solvent to remove saturated hydrocarbon, eluting by a sixth organic solvent to remove thioether, and removing the solvent from the sixth organic solvent eluent to obtain the thioether component.
According to a specific embodiment of the present invention, in the method for separating thioether compounds in petroleum oil products of the present invention, the petroleum oil products comprise one or a combination of several of crude oil, diesel oil fraction and vacuum gas oil fraction. The crude oil may be, for example, a low maturity crude oil.
According to a specific embodiment of the present invention, the method for separating thioether compounds in petroleum oil products of the present invention comprises the step of adding 0.1 wt% to 10.0 wt% of total sulfur, based on the total weight of the petroleum oil products.
According to a specific embodiment of the present invention, in the method for separating a thioether compound in a petroleum oil product according to the present invention, the first organic solvent, the second organic solvent, the third organic solvent, the fourth organic solvent, and the fifth organic solvent each independently comprise a mixture of one or more of n-heptane, n-hexane, n-pentane, and the like. In some embodiments of the invention, two or more of the first organic solvent, the second organic solvent, the third organic solvent, the fourth organic solvent, and the fifth organic solvent are the same or different. Preferably, the second organic solvent is the same as the third organic solvent, and/or the fourth organic solvent is the same as the fifth organic solvent. More preferably, the first organic solvent, the second organic solvent and the third organic solvent are the same, and/or the fourth organic solvent and the fifth organic solvent are the same. In some embodiments of the present invention, the first organic solvent, the second organic solvent, the third organic solvent, the fourth organic solvent, and the fifth organic solvent are the same.
According to the specific embodiment of the invention, in the method for separating the thioether compound in the petroleum oil product, the dosage of the organic solvent A for dissolving the petroleum oil product is 10-100 times of the volume of the petroleum oil product.
According to the specific embodiment of the invention, in the method for separating the thioether compounds in the petroleum oil product, the stationary phase of the alumina column chromatography is neutral alumina, and the dosage of the neutral alumina is 5-50 times of the weight of the petroleum oil product; preferably, the alumina is alumina capable of passing through a 200-300 mesh screen.
According to a specific embodiment of the present invention, in the method for separating a thioether compound in a petroleum oil product according to the present invention, the sixth organic solvent comprises one or a combination of n-hexane, dichloromethane, methanol, and the like. The sixth organic solvent is different from the fifth organic solvent. In some embodiments of the present invention, the sixth organic solvent is used in a volume ratio of 1 to 3: 3-1 parts of a mixed solvent of n-hexane and dichloromethane.
According to the specific embodiment of the invention, in the method for separating the thioether compound in the petroleum oil product, the stationary phase of the silica gel column chromatography is silica gel, and the dosage of the silica gel is 5-50 times of the weight of the petroleum oil product; preferably, the silica gel is silica gel capable of passing through a 200-300 mesh screen.
According to the specific embodiment of the invention, in the method for separating the thioether compound in the petroleum oil product, in the third step, the dosage of the fifth organic solvent is 40-200 times of the volume of the petroleum oil product, and the dosage of the sixth organic solvent is 5-50 times of the volume of the petroleum oil product.
According to the specific embodiment of the invention, in the method for separating the thioether compounds in the petroleum oil product, the quality of the alumina and the silica gel and the dosage of the organic solvent are in a proportional relationship; preferably an equal proportional linear relationship.
According to an embodiment of the present invention, in the method for separating a thioether compound in a petroleum product according to the present invention, in the third step, the method for concentrating the mixed solution eluted from the third organic solvent in the second step may be a concentration method that is conventional in the art, for example, the third organic solvent is removed under reduced pressure using a rotary evaporator. The specific concentration degree is not particularly required in the invention, most of the third organic solvent can be removed generally, and the specific volume can be determined according to the volume of silica gel column chromatography.
According to an embodiment of the present invention, in the method for separating a thioether compound in a petroleum product according to the present invention, the method for concentrating the mixed solution eluted from the sixth organic solvent may also be a concentration method conventional in the art, for example, a rotary evaporator is used to remove the sixth organic solvent under a reduced pressure condition to obtain the thioether compound. According to the specific embodiment of the present invention, in the method for separating a thioether compound in a petroleum product of the present invention, the fifth organic solvent and the sixth organic solvent are sequentially used for twice elution in the third step, and the obtained solution to be detected can be routinely detected by those skilled in the art, for example, the solution to be detected with a concentration of 10mg/mL (calculated by using the concentrated mixed solution as a solute) can be prepared for gas chromatography tandem mass spectrometry (GC-MS) analysis. And detecting that the thioether compounds are only detected in the sixth organic solvent elution component.
The method for separating the thioether compounds in the petroleum can separate the thioether compounds in the petroleum with high purity, is suitable for separating the thioether compounds in samples such as low-maturity crude oil, diesel oil fraction, vacuum gas oil fraction and the like, has mild operation conditions, and can completely, efficiently and accurately separate the thioether compounds in the petroleum products, particularly the low-maturity crude oil.
Drawings
FIG. 1 is a total ion flow diagram and a selected ion spectrum of the thioether compound obtained from the straight-run diesel oil in example 1 through GC-MS analysis.
FIG. 2 is a total ion flow diagram and a selective ion spectrum of the thioether compound obtained from the crude oil separation in example 2, which are analyzed by GC-MS.
FIG. 3 is a total ion flow diagram of the separated product in comparative example 1 and a characteristic ion mass chromatogram of the thioether compound.
Detailed Description
The technical solutions of the present invention will be described in detail below in order to clearly understand the technical features, objects, and advantages of the present invention, but the present invention is not limited to the practical scope of the present invention.
Example 1
The embodiment provides a method for separating thioether compounds in straight-run diesel, which comprises the following specific steps:
first, 50 mg of straight-run diesel oil having a total sulfur content of 1.47 wt% and 1 ml of n-hexane were added to a 2 ml sample bottle, and the sample bottle was shaken to completely dissolve the sample. Alumina (2.5 g, available through a 200-mesh 300-mesh screen) was then column chromatographed, eluting with 20 mL of n-hexane. The n-hexane eluate was concentrated, the n-hexane solvent was completely removed by a rotary evaporator under reduced pressure, and the concentrated sample was dissolved in 1 ml of n-hexane and subjected to silica gel (2.5 g, 200 mesh) column chromatography. In the process of silica gel column chromatography, 45 ml of n-hexane is used for washing, the component is discarded, then 20 ml of dichloromethane/n-hexane mixed solvent (2:1, v/v) is used for secondary elution, and the component is collected to be a thioether compound enriched component.
The GC-MS total ion flow diagram of the thioether compounds obtained by separation in this example and the selective ion spectrogram of the thioether compounds are shown in fig. 1. The results show that the thioether compounds in the straight-run diesel oil mainly exist in monocyclic cyclic thioether, and the thioether compounds present complete series distribution. The whole separation process takes short time and can be completed within 2 hours. In addition, by comparing the total ion flow diagram with the selective ion spectrogram of the thioether compound, the method is high in separation purity of the thioether compound and low in interference of non-thioether compounds.
Example 2
The embodiment provides a method for separating thioether compounds in low-maturity crude oil, which comprises the following specific steps:
first, 60 mg of a crude oil having a total sulfur content of 4.75 wt% and 1 ml of n-hexane were added to a 2 ml sample bottle, and the sample bottle was shaken to promote complete dissolution of the sample (some crude oils contained more asphaltenes, which resulted in incomplete dissolution and did not affect subsequent operations). First, column chromatography on alumina (3 g, available through 200-mesh 300-mesh) was carried out, eluting with 30 ml of n-hexane. The n-hexane eluate was concentrated by removing the n-hexane solvent completely under reduced pressure using a rotary evaporator, and the concentrated sample was dissolved in 1 ml of n-hexane and subjected to silica gel (3 g, which can pass through a 200-mesh 300-mesh sieve) column chromatography. During the separation by silica gel column chromatography, a first elution is carried out with 50 ml of n-hexane, followed by 20 ml of dichloromethane: the second elution was performed with n-hexane 2: 1. And detecting, wherein the thioether compounds are only detected in the second eluent. The GC-MS total ion flow diagram of the thioether compounds obtained by separation in this example and the selective ion spectrum of the thioether compounds are shown in fig. 2. The results show that the thioether compounds in the crude oil with low maturity have abundant sterane thioether besides monocyclic cyclic thioether series. The whole separation process takes short time and can be completed within 2 hours. In addition, by comparing the total ion flow diagram with the selective ion spectrogram of the thioether compound, the method is high in separation purity of the thioether compound and low in interference of non-thioether compounds.
Comparative example 1
This comparative example is directed to example 1, wherein the same alumina column separation conditions are used, but the silica column separation conditions are different, and the specific operation is as follows: the method is characterized in that n-hexane is not used for washing, 50 ml of dichloromethane/n-hexane mixed solvent (2:1, v/v) is directly used for elution, collected components are analyzed by GC-MS, a total ion flow diagram and a characteristic ion mass chromatogram of a thioether compound are shown in figure 3, and a spectrogram does not have a characteristic peak of the thioether compound, so that the success or failure of separation is determined by solvent washing conditions selected by silica gel column separation.
Claims (10)
1. A method for separating thioether compounds in petroleum products, comprising:
the method comprises the following steps: dissolving petroleum oil in a first organic solvent;
step two: transferring the dissolved oil sample to an alumina column chromatography wetted by a second organic solvent, eluting by a third organic solvent, and collecting the eluent;
step three: concentrating the collected eluent, transferring the concentrated eluent into a silica gel column chromatography wetted by a fourth organic solvent, sequentially eluting by a fifth organic solvent to remove saturated hydrocarbon, eluting by a sixth organic solvent to remove thioether, and removing the solvent from the sixth organic solvent eluent to obtain the thioether component.
2. The method of claim 1, wherein the petroleum oil comprises one or a combination of several of crude oils such as low maturity crude oils, diesel fractions, and vacuum gas oil fractions.
3. A process according to claim 1 or 2, wherein the total sulphur content is from 0.1 wt% to 10.0 wt%, based on the total weight of the petroleum oil.
4. The method of claim 1, wherein the first, second, third, fourth, and fifth organic solvents each independently comprise a mixture of one or more of n-heptane, n-hexane, and n-pentane;
two or more of the first organic solvent, the second organic solvent, the third organic solvent, the fourth organic solvent and the fifth organic solvent are the same or different from each other;
preferably, the second organic solvent is the same as the third organic solvent, and/or the fourth organic solvent is the same as the fifth organic solvent;
more preferably, the first organic solvent, the second organic solvent and the third organic solvent are the same, and/or the fourth organic solvent and the fifth organic solvent are the same.
5. The method according to claim 1 or 4, wherein the first organic solvent used for dissolving the petroleum oil is used in an amount of 10 to 100 times the volume of the petroleum oil.
6. The process according to claim 1, wherein the stationary phase of the alumina column chromatography is neutral alumina in an amount of 5-50 times the weight of the petroleum oil; preferably, the alumina is alumina capable of passing through a 200-300 mesh screen.
7. The method of claim 1, wherein the sixth organic solvent comprises a mixture of one or more of n-hexane, dichloromethane, and methanol; the sixth organic solvent is different from the fifth organic solvent; preferably, the sixth organic solvent is dichloromethane and n-hexane according to a volume ratio of 1-3: 3 to 1.
8. The method as claimed in claim 1, wherein the stationary phase of the silica gel column chromatography is silica gel, and the amount of the silica gel is 5-50 times of the weight of the petroleum oil product; preferably, the silica gel is silica gel capable of passing through a 200-300 mesh screen.
9. The method of claim 1, wherein the fifth organic solvent is used in an amount of 40 to 200 times the volume of the petroleum product and the sixth organic solvent is used in an amount of 5 to 50 times the volume of the petroleum product.
10. The method according to any one of claims 1 to 9, wherein the quality of the petroleum oil, the quality of the alumina and silica gel, and the amount of the organic solvent are in a proportional relationship; preferably an equal proportional linear relationship.
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