CN115228484A - Application of potassium sulfide in catalyzing high-sulfur synthesis gas to synthesize methyl mercaptan - Google Patents
Application of potassium sulfide in catalyzing high-sulfur synthesis gas to synthesize methyl mercaptan Download PDFInfo
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- CN115228484A CN115228484A CN202210113657.3A CN202210113657A CN115228484A CN 115228484 A CN115228484 A CN 115228484A CN 202210113657 A CN202210113657 A CN 202210113657A CN 115228484 A CN115228484 A CN 115228484A
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- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 37
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 32
- 229910052717 sulfur Inorganic materials 0.000 title claims abstract description 26
- 239000011593 sulfur Substances 0.000 title claims abstract description 26
- DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 29
- 239000003054 catalyst Substances 0.000 abstract description 28
- 238000000034 method Methods 0.000 abstract description 15
- 238000002360 preparation method Methods 0.000 abstract description 10
- 230000008569 process Effects 0.000 abstract description 5
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 239000003426 co-catalyst Substances 0.000 abstract 1
- 230000001276 controlling effect Effects 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 64
- 239000000203 mixture Substances 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000006004 Quartz sand Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 241000282326 Felis catus Species 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000007036 catalytic synthesis reaction Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 230000018199 S phase Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000013461 intermediate chemical Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
- B01J27/04—Sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention discloses a new application of potassium sulfide, namely the application of potassium sulfide in catalyzing high-sulfur synthesis gas to synthesize methyl mercaptan 3 In the SH reaction; the invention clearly discloses the preparation of CH by high-sulfur synthesis gas by simply regulating and controlling the components contained in the catalyst 3 The active phase in the SH process is K 2 S, contrary to the view of the use of alkali sulfide as a co-catalyst in most catalytic fields, the present invention is directed to the efficient synthesis of CH 3 SH provides a new way, and the method of the invention is simple, easy to operate and suitable for industrial production and market popularization and application.
Description
Technical Field
The invention relates to the use of potassium sulfide in catalyzing high sulfur synthesis gas (CO/H) 2 S/H 2 ) Synthesis of methyl mercaptan (CH) 3 SH), belonging to the technical field of methyl mercaptan preparation.
Background
Methyl mercaptan (CH) 3 SH) is an important chemical intermediate and industrial chemical, and can be used to produce high-value organic sulfur compounds, such as methionine, dimethyl disulfide, methanesulfonic acid, and the like. CH (CH) 3 SH is currently produced industrially predominantly via methanol (CH) 3 OH) and hydrogen sulfide (H) 2 S) reaction, but the process requires the preparation of CH through a cumbersome procedure 3 OH, then through CH 3 OH and H 2 Preparation of CH by S reaction 3 And (5) SH. The production process not only can cause the waste of resources and the improvement of production cost, but also can cause certain pollution to the environment. Recently, CO/H has been used as a catalyst 2 S/H 2 Preparation of CH from a high-sulfur synthesis gas 3 The method of SH has attracted some scholars' interest. The method produces CH 3 SH can not only remove malodorous gas H 2 S is recycled, and CH with high added value can be obtained 3 SH has very wide application prospect.
Conventionally with CH 3 OH and H 2 Preparation of CH by using S as raw material 3 In the SH method, the catalyst is mainly Co/Ni promoted Mo/W-based catalyst, and high-sulfur synthesis gas is used for preparing CH 3 SH starts later and its catalyst is also mainly a K promoted Mo/W based catalyst. Although there are a number of scholars on the preparation of CH from high sulfur synthesis gas catalyzed by K-Mo based catalyst 3 SH is studied, however, as the reaction is a multi-component complex system, the catalyst has a multi-phase structure, and the attribution of an active phase in the reaction process is always greatly controversial. Furthermore, K 2 S preparation of CH from high-sulfur synthesis gas 3 SH processes are generally regarded as cocatalysts; at present, there is no direct use of K 2 S catalytic synthesis of methyl mercaptan.
Disclosure of Invention
The invention aims to provide a new application of potassium sulfide, namely the application of potassium sulfide in catalyzing high-sulfur synthesis gas to synthesize methyl mercaptan.
The high-sulfur synthesis gas contains CO and H 2 S、H 2 In which H is 2 The molar concentration of S is 100000ppm to 700000000ppm, the molar concentration of CO is 100000ppm to 500000ppm, H is 2 The molar concentration is 100000ppm to 500000ppm, the methyl mercaptan is synthesized at 400-550 ℃, and the space velocity of the high-sulfur synthesis gas is 1000 to 10000h -1 。
The method has the advantages and the technical effects that:
(1) The invention proves that K is 2 S preparation of CH from high-sulfur synthesis gas 3 The SH plays the role of an active phase rather than the traditional thought of as a cocatalyst, and can be used for preparing CH for high-sulfur synthesis gas 3 Theoretical research of SH lays a certain foundation, and meanwhile, a new idea can be provided for revealing the action of alkali metal in the catalyst containing the alkali metal in other fields;
(2) Active phase K demonstrated by the invention 2 S phase ratio and MoS 2 The raw materials are easy to obtain, the cost is lower, and the method is suitable for industrial production and market popularization and application;
(3) In the present invention, K 2 S is then available to catalyze CH 3 SH generation, avoiding conventional catalytic CH 3 And the complicated steps such as catalyst preparation and the like in the SH generation process are favorable for market popularization and application.
Drawings
FIG. 1 is a diagram of the catalytic synthesis of CH by the catalyst in example 1 3 A graph of SH generation rate results;
FIG. 2 is the catalytic synthesis of CH by the catalyst in example 2 3 A schematic diagram of the generation rate result of SH;
FIG. 3 shows different catalysts for preparing CH from high-sulfur synthesis gas 3 Graph of CO conversion in SH process;
FIG. 4 shows H for different catalysts 2 -TPR profile.
Detailed Description
The present invention is further illustrated in detail by the following examples, but the scope of the present invention is not limited thereto, wherein the methods are all conventional methods unless otherwise specified, and the reagents are all conventional reagents or reagents formulated by conventional methods unless otherwise specified;
example 1: k 2 S-catalyzed synthesis of methyl mercaptan from high-sulfur synthesis gas
By commercial K 2 S is a catalyst (denoted as K) 2 S), mixing 0.4g of the mixture with quartz sand in equal mass after tabletting treatment, uniformly mixing the mixture, putting the mixture into a tubular furnace reactor, and introducing high-sulfur synthesis gas (H) 2 The molar concentration of S gas in the mixed gas is 500000ppm, the molar concentration of CO gas in the mixed gas is 100000ppm, H gas in the mixed gas is 2 The molar concentration of the gas in the mixed gas is 400000 ppm), and the total space velocity of the gas feeding is 3000 h -1 The pressure of the reaction system is normal pressure, the reaction temperature is 150, 175, 200, … …, 600 and 625 ℃, the highest CO conversion rate can reach 22.2 percent in the reaction process, and CH is catalyzed only at high temperature 3 SH formation, highest CH 3 The SH formation rate is about 586nmol g cat -1 ·s -1 See fig. 1, 3;
simultaneously with MoS 2 、K-MoS 2 -C is catalyst synthesis methyl mercaptan as control;
in the form of commercially available MoS 2 As a catalyst (noted MoS) 2 -C), mixing 0.4g of the mixture with quartz sand in equal mass after tabletting treatment, uniformly mixing the mixture, putting the mixture into a tubular furnace reactor, and introducing high-sulfur synthesis gas (H) 2 The molar concentration of S gas in the mixed gas is 500000ppm, the molar concentration of CO gas in the mixed gas is 100000ppm, H gas in the mixed gas is 2 The molar concentration of the gas in the mixed gas is 400000 ppm), and the total space velocity of the gas feeding is 3000 h -1 The pressure of the reaction system is normal pressure, the reaction temperature is 150, 175, 200, … …, 600 and 625 ℃, respectively, in the reaction process, the CO conversion rate can reach 6 percent at most, but CH is hardly catalyzed 3 SH generation, see fig. 1, 3;
in the form of commercially available MoS 2 And K 2 S is a precursor, and the K-Mo catalyst (marked as K-MoS) is prepared by an impregnation method 2 -C), in particular 0.6888g K 2 S is dissolved in0.95mL of water, then 1g of MoS 2 Fully stirring and carrying out ultrasonic treatment for 10min, standing for 3h, and then drying in a vacuum drying oven at 60 ℃ for 8h to obtain a K-Mo-based catalyst;
the K-Mo based catalyst is tableted, 0.4g of the K-Mo based catalyst is mixed with quartz sand in equal mass, the mixture is uniformly mixed and then is put into a tubular furnace reactor, and high-sulfur synthesis gas (H) is introduced 2 The molar concentration of S gas in the mixed gas is 500000ppm, the molar concentration of CO gas in the mixed gas is 100000ppm, H gas in the mixed gas is 2 The molar concentration of the gas in the mixed gas is 400000 ppm), and the total space velocity of the feed is 3000 h -1 The pressure of the reaction system is normal pressure, the reaction temperature is 150, 175, 200, … …, 600 and 625 ℃, the CO conversion rate can reach 28.4 percent at most in the reaction process, and CH is catalyzed only at high temperature 3 SH formation, highest CH 3 The SH production rate is about 487.3 nmol g cat -1 ·s -1 See fig. 1 and 3.
Example 2
1.728g of molybdenum trioxide, 3.498g of potassium thiocyanate and 1.008g of sodium fluoride are used as raw materials, 60mL of mixed solution (volume ratio is 2/1) of water and glycerol is used as a hydrothermal synthesis agent, the mixture reacts for 24h at 220 ℃, and a black solid product is washed, filtered and dried in vacuum at 60 ℃ to obtain the hollow MoS 2 Material (written as MoS) 2 -H; in addition, to obtain sufficient MoS 2 4 parts of this material are prepared in the same way and mixed until use).
0.4g of MoS was taken 2 H, tabletting, mixing with quartz sand, placing into a tubular furnace reactor, introducing high-sulfur synthesis gas (H) 2 The molar concentration of S gas in the mixed gas is 500000ppm, the molar concentration of CO gas in the mixed gas is 100000ppm, H gas in the mixed gas is 2 The molar concentration of the gas in the mixed gas is 400000 ppm), and the total space velocity of the feeding is 3000 h -1 The reaction system pressure is normal pressure, the reaction temperature is 150, 175, 200, … …, 600 and 625 ℃, respectively, in the reaction process, the CO conversion rate can reach 16.4 percent at most, and CH is hardly catalyzed 3 SH generation, see fig. 2, 3;
in MoS 2 -H and commercially available K 2 S is a precursor, and the K-Mo catalyst (marked as K-MoS) is prepared by an impregnation method 2 -C), in particular 0.6888g K 2 S was dissolved in 0.95mL of water, then 1g of MoS was added 2 And (4) fully stirring and carrying out ultrasonic treatment on the mixture for 10min, standing for 3H, and drying in a vacuum drying oven at the temperature of 60 ℃ for 8H to obtain the K-Mo-based catalyst.
The K-Mo based catalyst is tabletted, 0.4g of the K-Mo based catalyst is mixed with quartz sand in equal mass, the mixture is evenly mixed and then is put into a tubular furnace reactor, high-sulfur synthesis gas is introduced (the same as above), and the total space velocity of feeding is 3000 h -1 The pressure of the reaction system is normal pressure, the reaction temperatures are 150, 175, 200, … …, 600 and 625 ℃, the highest CO conversion rate can reach 36.6 percent in the reaction process, and the CH can be catalyzed at both low temperature and high temperature 3 SH formation, highest CH at Low temperatures 3 The SH production rate is about 608.9 nmol g cat -1 ·s -1 Highest CH at high temperature 3 The SH production rate is about 436.3 nmol g cat -1 ·s -1 See fig. 2 and 3.
The above results show that K 2 S is the active phase in the real methyl mercaptan synthesis, moS 2 Has promoting effect.
H from FIG. 4 2 The high temperature region can be seen in the TPR representation, all with the addition of K 2 The catalysts of S all have strong reduction peaks, and the combination of activity results can prove that CH is in a high-temperature region 3 SH is generated from K 2 S-induced; for K-MoS 2 -C and K-MoS 2 -H, hollow structural K-MoS 2 The low-temperature reduction peak of-H is obviously shifted towards the high-temperature direction, while K-MoS 2 Little low temperature reduction peak for-C (both catalysts contain MoS) 2 And K 2 S, their difference lies in MoS 2 Difference in morphology); binding to MoS 2 -C、MoS 2 -H、K-MoS 2 -C and K-MoS 2 -H catalyzes CH at low temperature 3 The difference in SH-forming properties was confirmed by the low temperature region CH 3 The difference in SH production is MoS of different morphologies 2 To K 2 S results of regulation, i.e. MoS 2 Acts as a cocatalyst, and K 2 S is CH 3 Active phase during SH synthesis.
Example 3: k 2 S-catalyzed synthesis of methyl mercaptan from high-sulfur synthesis gas
By commercial K 2 S is a catalyst (denoted as K) 2 S), mixing 0.2g of the mixture with quartz sand in equal mass after tabletting treatment, uniformly mixing, putting the mixture into a tubular furnace reactor, and introducing high-sulfur synthesis gas (H) 2 The molar concentration of S gas in the mixed gas is 500000ppm, the molar concentration of CO gas in the mixed gas is 100000ppm, H gas in the mixed gas is 2 The molar concentration of the gas in the mixed gas is 400000 ppm), and the total space velocity of the gas feeding is 6000 h -1 The reaction system pressure is normal pressure, methyl mercaptan is synthesized at 450 ℃, the CO conversion rate can reach 10 percent at most in the reaction process, and CH is catalyzed only at high temperature 3 SH formation, highest CH 3 The SH production rate is about 382.3nmol g cat -1 ·s -1 。
Claims (2)
1. The application of potassium sulfide in catalyzing high-sulfur synthesis gas to synthesize methyl mercaptan.
2. Use according to claim 1, characterized in that: the high-sulfur synthesis gas contains CO and H 2 S、H 2 In which H is 2 The molar concentration of S is 100000ppm to 700000000ppm, the molar concentration of CO is 100000ppm to 500000ppm, H is 2 The molar concentration of the synthetic gas is 100000ppm to 500000ppm, the methyl mercaptan is synthesized at the normal pressure and the temperature of 400-550 ℃, and the space velocity of the high-sulfur synthetic gas is 1000 to 10000h -1 。
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4410731A (en) * | 1978-03-06 | 1983-10-18 | Pennwalt Corporation | Process for the manufacture of methyl mercaptan from carbon oxides |
| CN102658208A (en) * | 2012-04-28 | 2012-09-12 | 重庆紫光天化蛋氨酸有限责任公司 | Methyl mercaptan catalyst, and preparation method and application thereof |
| CN112316959A (en) * | 2020-11-18 | 2021-02-05 | 昆明理工大学 | K insertion type 1T-MoS2Catalyst, preparation method and application thereof |
-
2022
- 2022-01-30 CN CN202210113657.3A patent/CN115228484A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4410731A (en) * | 1978-03-06 | 1983-10-18 | Pennwalt Corporation | Process for the manufacture of methyl mercaptan from carbon oxides |
| CN102658208A (en) * | 2012-04-28 | 2012-09-12 | 重庆紫光天化蛋氨酸有限责任公司 | Methyl mercaptan catalyst, and preparation method and application thereof |
| CN112316959A (en) * | 2020-11-18 | 2021-02-05 | 昆明理工大学 | K insertion type 1T-MoS2Catalyst, preparation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| MIAO YU, ET AL: "Alkali catalyzes methanethiol synthesis from CO and H2S", JOURNAL OF CATALYSIS, vol. 405, pages 117 * |
| MIAO YU: "Catalytic synthesis of methanethiol and its conversion to light olefins", TECHNISCHE UNIVERSITEIT EINDHOVEN: CHEMICAL ENGINEERING AND CHEMISTRY [PHD], pages 75 * |
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