CN115974643A - Enrichment and separation method of mercaptan sulfur-containing compounds in coking benzene hydrogenation xylene product - Google Patents
Enrichment and separation method of mercaptan sulfur-containing compounds in coking benzene hydrogenation xylene product Download PDFInfo
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Abstract
The invention belongs to the technical field of chemical industry, and particularly relates to an enrichment and separation method of mercaptan sulfur-containing compounds in a coking benzene hydrogenation dimethylbenzene product, which comprises the following steps: oxidizing the xylene product by using iodine or oxygen as an oxidant, oxidizing and converting thiol compounds in the xylene product into disulfide compounds, and separating most of xylene by distillation by utilizing the characteristic of large difference between the boiling points of the disulfide compounds and the xylene to finish enrichment and separation of the thiol compounds. The enrichment and separation of the thiol sulfur-containing compounds of the invention has simple method and low cost, and is very suitable for industrial production.
Description
Technical Field
The invention belongs to the technical field of chemical industry, and particularly relates to an enrichment and separation method of mercaptan sulfur-containing compounds in a coking benzene hydrogenation dimethylbenzene product.
Background
Hydrodesulfurization (HDS) is an important technical means for hydrofining treatment of petrochemical heavy oil fractions, the hydrogenation conditions are mild, secondary macromolecular mercaptan (heavy mercaptan) sulfur-containing compounds can be generated in the hydrogenation process while the total sulfur content is reduced, the mercaptan sulfur-containing compounds are low in the hydrogenated heavy fraction, but the stability is high and difficult to remove, and the oil product can generate peculiar smell due to the existence of the mercaptan sulfur-containing compounds. The catalyst, the hydrogenation device, the hydrogenation reaction process parameters and other aspects used in the coking benzene hydrogenation process are very close to those of a petrochemical oil product Hydrodesulfurization (HDS) process, in the actual production process, the benzene hydrogenation xylene product can generate peculiar smell due to the existence of thiol sulfur-containing compounds, the product quality is reduced, adverse effects are generated on the subsequent processing and use of the xylene product, but the sulfur content of the benzene hydrogenation xylene product is very low (< 1.0 ppm), the accurate analysis and determination of the thiol sulfur-containing compounds in the benzene hydrogenation xylene product are difficult, and the enrichment and separation treatment of the thiol sulfur-containing compounds is required on the xylene product.
The mercaptan sulfur-containing compounds in petrochemical hydrogenated oil products are usually enriched and separated in a solvent extraction mode, a specific extractant is often needed (analysis of the structure composition of the hydrogenated refined gasoline mercaptan and deodorization research [ D ], china Petroleum university, 2011), the operation steps are complicated, and due to the fact that the composition of the coking benzene hydrogenated xylene products is greatly different from that of the petrochemical hydrogenated oil products, the enrichment and separation treatment method in the petrochemical hydrogenated oil products is not completely suitable for the coal coking benzene hydrogenated xylene products, and the enrichment and separation treatment mode for the mercaptan sulfur-containing compounds in the xylene products is not reported in related documents.
Therefore, the determination of the enrichment and separation method of the mercaptan sulfur-containing compounds in the xylene products can realize the accurate analysis and determination of the mercaptan sulfur-containing compounds, and has important significance for the improvement of product quality and the subsequent processing and utilization.
Disclosure of Invention
The invention aims to overcome the problems in the prior art and provide a method for enriching and separating mercaptan sulfur-containing compounds in a coking benzene hydrogenation xylene product.
In order to achieve the technical purpose and achieve the technical effect, the invention is realized by the following technical scheme:
a process for enriching and separating the sulfur-containing thiol compounds from the hydrogenated xylene product of coking benzene includes such steps as oxidizing the thiol compounds by weak oxidant to become disulfide compounds, and distilling to separate out most of xylene.
Further, the method for enriching and separating the mercaptan sulfur-containing compounds in the coking benzene hydrogenation xylene product comprises the following steps:
1) Taking a proper amount of xylene product, and carrying out oxidation treatment by taking iodine or oxygen as an oxidant to obtain oxidation pretreated xylene;
2) Placing a proper amount of the oxidation pretreated dimethylbenzene obtained in the step 1) in a reduced pressure distillation device, carrying out distillation separation under the conditions of 1.3-2.0 kPa and 50-70 ℃, ending distillation until a certain amount of materials are left at the bottom of a kettle, collecting at room temperature, and accurately measuring the volume of a collected distillation substrate, wherein the collected distillation substrate is an enriched and separated thiol sulfur-containing compound sample.
Further, according to the enrichment and separation method for mercaptan sulfur-containing compounds in the coking benzene hydrogenation xylene product, in the step 1), the xylene product is a xylene product obtained by hydrogenation of coal coking benzene.
Further, in the above method for enriching and separating mercaptan sulfur-containing compounds in the hydrogenated xylene product from coking benzene, in step 1), when the oxidant is iodine, the iodine oxidation treatment is specifically operated as follows: adding an iodine dimethylbenzene solution with the iodine mass concentration of 20-40 wt% into a proper amount of dimethylbenzene product, and carrying out oxidation treatment at room temperature for 4-10 hours to obtain iodine oxidation pretreated dimethylbenzene.
Further, according to the method for enriching and separating the mercaptan sulfur-containing compounds in the coking benzene hydrogenation xylene product, the volume ratio of the iodoxylene solution to the xylene product is 2-4.
Further, in the above method for enriching and separating the mercaptan sulfur-containing compounds in the hydrogenated xylene product from coking benzene, when the oxidant is oxygen in step 1), the specific operation of the oxygen oxidation treatment is as follows: taking a proper amount of dimethylbenzene product, treating for 4-10 hours at room temperature-70 ℃ in an oxygen atmosphere, and cooling to room temperature to obtain the oxygen oxidation pretreated dimethylbenzene.
Further, in the above-mentioned method for enriching and separating the mercaptan sulfur-containing compounds in the coking benzene hydrogenation xylene product, in step 2), the distillation separation is vacuum distillation.
Further, in the enrichment and separation method of mercaptan sulfur-containing compounds in the coking benzene hydrogenation xylene product, in the step 2), the volume ratio of the residual material distilled to the bottom of the kettle to the oxidation pretreatment xylene is 5-10: and 100 ends.
The invention has the beneficial effects that:
1. the invention utilizes the characteristic that the mercaptan compounds are easily oxidized by weak oxidants and are converted into disulfide compounds, the xylene products obtained by hydrogenation of coal coking benzene are obtained by distillation separation, the boiling point of the contained mercaptan compounds is close to that of xylene, the disulfide compounds formed by oxidation of the mercaptan compounds have boiling points which are not only higher than that of the mercaptan compounds but also higher than that of the xylene, and most of xylene is separated by distillation by utilizing the characteristic that the difference between the boiling points of the disulfide compounds and the xylene is large, so that enrichment and separation of the mercaptan compounds are completed.
2. The enrichment and separation of the thiol sulfur-containing compounds of the invention has simple method and low cost, and is very suitable for industrial production.
Of course, it is not necessary for any one product that embodies the invention to achieve all of the above advantages simultaneously.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The following embodiments are relevant to the present invention:
example 1
200ml of xylene (benzene hydrogenated xylene product, the specific components of which are shown in table 1, of Anhui horse Steel chemical energy science and technology Co., ltd.) is placed in a 500ml three-neck flask, 4.0ml of iodine xylene solution with the iodine mass concentration of 40wt% is added, and the mixture is oxidized at room temperature for 4 hours to obtain an iodine oxidation pretreated xylene sample. 100ml of iodine oxidation pretreated dimethylbenzene is placed in a reduced pressure distillation device to be distilled and separated at the pressure of 2.0kPa and the temperature of 70 ℃, the distillation is finished when 5ml of materials are left at the bottom of a kettle, a distillation substrate is collected to obtain an enriched and separated mercaptan sulfur-containing compound sample, and the sulfur content is analyzed and tested by a JF-TSN-3000 type sulfur-nitrogen analyzer (Jiangsu Jiangdu electronic analysis instruments, ltd.), wherein the sulfur content test result is shown in Table 2.
Example 2
200ml of xylene (benzene hydrogenated xylene product, the specific components of which are shown in table 1, of Anhui horse Steel chemical energy science and technology Co., ltd.) is put into a 500ml three-neck flask, 6.0ml of iodine xylene solution with the iodine mass concentration of 30wt% is added, and the mixture is oxidized for 8 hours at room temperature to obtain an iodine oxidation pretreated xylene sample. 100ml of iodine oxidation pretreated dimethylbenzene is placed in a reduced pressure distillation device to be distilled and separated at the pressure of 1.6kPa and the temperature of 60 ℃, the distillation is finished when 8ml of materials are left at the bottom of a kettle, a distillation substrate is collected to obtain an enriched and separated mercaptan sulfur-containing compound sample, and the sulfur content is analyzed and tested by a JF-TSN-3000 type sulfur-nitrogen analyzer (Jiangsu Jiangdu electronic analysis instruments, ltd.), wherein the sulfur content test result is shown in Table 2.
Example 3
200ml of xylene (benzene hydrogenated xylene product, the specific components of which are shown in table 1, of Anhui horse Steel chemical energy science and technology Co., ltd.) was taken and placed in a 500ml three-necked flask, 8.0ml of an iodoxylene solution with an iodine mass concentration of 20wt% was added, and oxidation was carried out at room temperature for 10 hours to obtain an iodoxy pretreated xylene sample. 100ml of iodine oxidation pretreated dimethylbenzene is placed in a reduced pressure distillation device to be distilled and separated at the pressure of 1.3kPa and the temperature of 50 ℃, the distillation is finished when 10ml of materials are left at the bottom of a kettle, a distillation substrate is collected to obtain an enriched and separated mercaptan sulfur-containing compound sample, and the sulfur content is analyzed and tested by a JF-TSN-3000 type sulfur-nitrogen analyzer (Jiangsu Jiangdu electronic analysis instruments, ltd.), and the sulfur content test result is shown in Table 2.
Example 4
200ml of xylene (benzene hydrogenated xylene product, the specific components are shown in table 1, of Anhui Ma Steel chemical energy technology Co., ltd.) is placed in a 500ml three-neck flask, and oxygen is introduced to oxidize at 70 ℃ for 4 hours to obtain an oxygen oxidation pretreated xylene sample. 100ml of dimethylbenzene pretreated by oxygen oxidation is placed in a reduced pressure distillation device to be distilled and separated at the pressure of 1.3kPa and the temperature of 50 ℃, the distillation is finished when 10ml of materials are left at the bottom of a kettle, a distillation substrate is collected to obtain an enriched and separated mercaptan sulfur-containing compound sample, and the sulfur content is analyzed and tested by a JF-TSN-3000 type sulfur-nitrogen analyzer (Jiangsu Jiangdu electronic analyzer Co., ltd.), wherein the test result of the sulfur content is shown in Table 2.
Example 5
200ml of xylene (benzene hydrogenated xylene product, the specific components are shown in table 1, of Anhui Ma Steel chemical energy technology Co., ltd.) is placed in a 500ml three-neck flask, and oxygen is introduced to oxidize at 50 ℃ for 8 hours to obtain an oxygen oxidation pretreated xylene sample. 100ml of oxygen is taken to oxidize and pretreat dimethylbenzene, the dimethylbenzene is placed in a reduced pressure distillation device to be distilled and separated at the pressure of 1.6kPa and the temperature of 60 ℃, the distillation is finished when 8ml of materials are remained at the bottom of a kettle, a distillation substrate is collected to obtain an enriched and separated mercaptan sulfur-containing compound sample, and the sulfur content is analyzed and tested by a JF-TSN-3000 type sulfur-nitrogen analyzer (Jiangsu Jiangdi electronic analysis instruments, ltd.), and the test result of the sulfur content is shown in Table 2.
Example 6
200ml of xylene (benzene hydrogenated xylene product, the specific components are shown in table 1, of Anhui Ma Steel chemical energy science and technology Co., ltd.) is placed in a 500ml three-neck flask, and an oxygen introducing chamber is used for warm oxidation for 10 hours to obtain an oxygen oxidation pretreated xylene sample. 100ml of dimethylbenzene pretreated by oxygen oxidation is placed in a reduced pressure distillation device to be distilled and separated at the pressure of 2.0kPa and the temperature of 70 ℃, the distillation is finished when 5ml of materials are left at the bottom of a kettle, a distillation substrate is collected to obtain an enriched and separated mercaptan sulfur-containing compound sample, and the sulfur content is analyzed and tested by a JF-TSN-3000 type sulfur-nitrogen analyzer (Jiangsu Jiangdu electronic analyzer Co., ltd.), wherein the test result of the sulfur content is shown in Table 2.
Comparative examples
100ml of dimethylbenzene (benzene hydrogenated dimethylbenzene product of chemical energy technology limited of Anhui horse, the specific components are shown in Table 1) is placed in a reduced pressure distillation device to be distilled and separated at the pressure of 2.0kPa at 70 ℃, distillation is finished until 5ml of material is left at the bottom of a kettle, a distillation substrate is collected to obtain an enriched and separated mercaptan sulfur-containing compound sample, and the sulfur content is analyzed and tested by a JF-TSN-3000 type sulfur-nitrogen analyzer (Jiangsu Jiangdu electronic analyzer, the company Limited), and the sulfur content test result is shown in Table 2.
TABLE 1 xylene product major Components
The results in Table 2 show that the enrichment and separation method of the thiol sulfur-containing compounds of the present invention has a good enrichment and separation effect, in the comparative example, the total sulfur content of the distillation raw material and the sample after enrichment and separation is 0.8ppm and 0.9ppm, respectively, and the sulfur content is basically unchanged, which indicates that the thiol sulfur-containing compounds cannot be effectively enriched and separated without oxidation treatment; the enrichment and separation of thiol sulfur-containing compounds can be realized by both iodine oxidation and oxygen oxidation, the total sulfur content of 5ml of samples obtained by the enrichment and separation reaches 21.4ppm after the iodine oxidation treatment in example 1, and the total sulfur content of 10ml of samples obtained by the enrichment and separation reaches 10.8ppm after the oxygen oxidation treatment in example 4, which are both greatly improved compared with 0.9ppm of the enrichment and separation samples in the comparative example. The enrichment and separation of the thiol sulfur-containing compounds of the invention has simple method and low cost, and is very suitable for industrial production.
TABLE 2 Sulfur content of enriched separation samples of the different examples
The preferred embodiments of the invention disclosed above are intended to be illustrative only. The preferred embodiments are not intended to be exhaustive or to limit the invention to the precise embodiments disclosed. Obviously, many modifications and variations are possible in light of the above teaching. The embodiments were chosen and described in order to best explain the principles of the invention and the practical application, to thereby enable others skilled in the art to best utilize the invention. The invention is limited only by the claims and their full scope and equivalents.
Claims (8)
1. The method is characterized in that mercaptan compounds are oxidized by a weak oxidant and converted into disulfide compounds, and then most of xylene is separated by distillation by utilizing the characteristic of large difference between the boiling points of the disulfide compounds and the xylene, so that enrichment and separation of the mercaptan compounds are completed.
2. The method for enriching and separating the mercaptan sulfur-containing compounds in the coking benzene hydrogenation xylene product according to claim 1, is characterized by comprising the following steps:
1) Taking a proper amount of xylene product, and carrying out oxidation treatment by taking iodine or oxygen as an oxidant to obtain oxidation pretreated xylene;
2) Placing a proper amount of the oxidation pretreated dimethylbenzene obtained in the step 1) in a reduced pressure distillation device, carrying out distillation separation under the conditions of 1.3-2.0 kPa and 50-70 ℃, ending distillation until a certain amount of materials are left at the bottom of a kettle, collecting at room temperature, and accurately measuring the volume of a collected distillation substrate, wherein the collected distillation substrate is an enriched and separated thiol sulfur-containing compound sample.
3. The method for enriching and separating the mercaptan sulfur-containing compounds in the coking benzene hydrogenation xylene product according to claim 2, wherein in the step 1), the xylene product is a xylene product obtained by hydrogenation of coal coking benzene.
4. The method for enriching and separating mercaptan sulfur-containing compounds in a coking benzene hydrogenation xylene product according to claim 2, wherein in the step 1), when the oxidant is iodine, the iodine oxidation treatment is specifically operated as follows: adding an iodine dimethylbenzene solution with the iodine mass concentration of 20-40 wt% into a proper amount of dimethylbenzene product, and carrying out oxidation treatment at room temperature for 4-10 hours to obtain iodine oxidation pretreated dimethylbenzene.
5. The method for enriching and separating the mercaptan sulfur-containing compounds in the coking benzene hydrogenation xylene product according to claim 4, characterized in that the volume ratio of the iodoxylene solution to the xylene product is 2-4.
6. The method for enriching and separating the mercaptan sulfur-containing compounds in the coking benzene hydrogenation xylene product according to claim 2, wherein in the step 1), when the oxidant is oxygen, the oxygen oxidation treatment is specifically operated as follows: taking a proper amount of dimethylbenzene product, treating for 4-10 hours at room temperature-70 ℃ in an oxygen atmosphere, and cooling to room temperature to obtain the oxygen oxidation pretreated dimethylbenzene.
7. The method for enriching and separating the mercaptan sulfur-containing compounds in the coking benzene hydrogenation xylene product according to claim 2, wherein in the step 2), the distillation separation is vacuum distillation.
8. The method for enriching and separating the mercaptan sulfur-containing compounds in the coking benzene hydrogenation xylene product according to claim 2, characterized in that in the step 2), the volume ratio of the residual materials distilled to the bottom of the kettle to the oxidation pretreatment xylene is 5-10: and 100 ends.
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