CN1420116A - Process and apparatus for synthesis of thiophene - Google Patents
Process and apparatus for synthesis of thiophene Download PDFInfo
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- CN1420116A CN1420116A CN 01135132 CN01135132A CN1420116A CN 1420116 A CN1420116 A CN 1420116A CN 01135132 CN01135132 CN 01135132 CN 01135132 A CN01135132 A CN 01135132A CN 1420116 A CN1420116 A CN 1420116A
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- thiophene
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- sulfur
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 229930192474 thiophene Natural products 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000003786 synthesis reaction Methods 0.000 title claims description 9
- 230000015572 biosynthetic process Effects 0.000 title claims description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 28
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000011593 sulfur Substances 0.000 claims abstract description 21
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 21
- 239000000047 product Substances 0.000 claims abstract description 19
- 239000011265 semifinished product Substances 0.000 claims abstract description 13
- 239000007789 gas Substances 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 8
- 239000012495 reaction gas Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000003860 storage Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 239000010865 sewage Substances 0.000 claims description 5
- 239000000295 fuel oil Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000005864 Sulphur Substances 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002994 raw material Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000011269 tar Substances 0.000 description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
- 239000006200 vaporizer Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000006477 desulfuration reaction Methods 0.000 description 3
- 230000023556 desulfurization Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000011280 coal tar Substances 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 239000003079 shale oil Substances 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- -1 optical brighteners Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A process for synthesizing thiophene includes the reaction for gas-phase sulfur and 1,3-butadiene, and extracting thiophene from resultant gas. Its apparatus is composed of tubular reactor, reactive settling tank, vertical settling tube, vertical condensing cooler, three-phase separator, tank of semifinished product and rectifying tower. Its advantages are low cost and high purity (more than 99.5%) and quality of product.
Description
Technical Field
The invention relates to a method and a device for producing thiophene.
Background
Thiophene, also known as thiacyldiene, is a colorless, transparent liquid that has an aromatic odor similar to benzene and is flammable. Melting point-383 deg.C, boiling point 84.12 deg.C, relative density 1.0644(20 deg.C), flash point-1.1 deg.C, refractive index 1.5289(20 deg.C), water-insoluble, easily soluble in ethanol, diethyl ether and other organic solvents, and no decomposition when heated to 850 deg.C.
The main uses ofthiophene are: synthetic drugs such as semisynthetic penicillins, cephalosporins, anthelmintics, antihistamines, etc.; synthetic dyes, pesticides, optical brighteners, flavoring agents, and the like; synthesis of several complex reagents; the method is used for extraction and separation of uranium metal and the like. According to recent reports, thiophenes are used in the manufacture of computer chips.
The traditional thiophene production method is to extract naturally occurring substances, and thiophene mainly exists in coal tar and shale oil. The extraction method is roughly as follows: rectifying the mixed fraction of benzene to remove toluene, and then washing with 85% sulfuric acid with 5% of raw material amount to remove unsaturated compounds; then, the mixture was washed with 98% sulfuric acid in an amount of 7% based on the starting material to separate the acid solution from benzene. The method comprises the steps of hydrolyzing waste acid liquor serving as a raw material at 110-150 ℃, enabling gas generated during hydrolysis to enter a tower top condenser through a hydrolysis rectifying tower, and condensing to obtain a product containing 15-25% of thiophene, 50-60% of xylene, benzene, toluene, methylthiophene and some unknown substances. About 10 kg of rectification products can be extracted from each ton of waste acid liquor. And (3) dehydrating the rectification product by using solid sodium hydroxide, and repeatedly rectifying and refining (finally carrying out azeotropic rectification with ethanol) to obtain a thiophene product with the content of 90-95%.
The quality index is as follows: first and second stages
% by weight chromatography 95% 90%
Relative density (20 ℃ C.) 1.0551.044
Refractive index 1.52651.5260
From the above, it is obvious that the method for producing thiophene from naturally occurring substances is very complicated, the cost is high, the product quality is poor, the boiling points of benzene, toluene and thiophene are relatively close, the separation is difficult, and the method is particularly limited by the process for refining coal tar and shale oil (the process is backward, seriously polluted and rarely used).
The organic thiophene synthesis has been reported abroad, and the adopted raw materials mainly comprise carbon disulfide and n-butane or n-butanol.
Disclosure of Invention
The invention aims to solve the technical problem of providing a thiophene synthesis production process and a production device, and industrially producing a high-purity thiophene product at low cost.
The process for synthesizing thiophene of the present invention is characterized in that gas-phase sulfur and 1, 3-butadiene are reacted, and thiophene is extracted from the generated reaction gas product.
The method adopts an organic synthesis process, selects proper raw materials, and obtains products with high concentration of … thiophene which is a target product after the raw materials react, so that the extraction is easy. The gaseous sulfur is obtained from solid sulfur according to known technical methods.
The reaction equation is:
the reaction of the gas-phase sulfur and the 1, 3-butadiene can be carried out in the presence of a catalyst or in the absence of the catalyst, and the reaction conditions without the catalyst provided by the reaction are as follows: the reaction temperature is 250-550 ℃, preferably 380-480 ℃, and the pressure (gauge pressure) is 0.05-0.25 Mpa. In order to achieve sufficient reaction, the linear reaction speed is preferably 1.5 to 3.0m/s, and the reaction time is preferably 1 to 3 seconds. The weight ratio of the gas-phase sulfur to the 1, 3-butadiene is preferably 1.04-1.33: 1.
Meanwhile, in order to control the temperature in the reaction process to be uniform, the reaction depth can be controlled by adopting a mode of external heating and temperature reduction by adding a small amount of water vapor inside (the reaction temperature in the reactor is kept to be uniform). The amount of the steam has no direct influence on the reaction as long as the reaction temperature can be ensured. The addition of steam also reduces the formation of coke by the reaction.
The reaction gas product obtained after the reaction comprises tail gas (rich in hydrogen sulfide), semi-finished product liquid and a small amount of heavy oil, and thiophene is contained in the semi-finished product liquid. Therefore, the reaction gas product is firstly cooled to 250-350 ℃, heavy oil in the reaction by-products is removed, then the reaction gas product is cooled to 40-50 ℃ through condensation, tail gas, sulfur-containing sewage and semi-finished product liquid three-phase substances in the reaction product are separated, semi-finished product liquid substances are rectified, and 83.5-84.5 ℃ fractions are collected, namely thiophene. The tail gas is treated by two-stage alkali washing and desulfurization by a desulfurization catalyst bed layer according to a common method, so that the hydrogen sulfide content in the tail gas finally discharged at high altitude is not more than 2 ppm.
The production device for completing the process comprises a tubular reactor, a reaction settling tank connected with the tubular reactor, a vertical settling tube connected with the reaction settling tank, a vertical condensation cooler connected with the vertical settling tube, wherein the outlet of the condensation cooleris connected with a three-phase separator, the lower part of the three-phase separator is connected with a semi-finished product storage tank, and the storage tank is connected with an intermittent rectifying tower.
The invention has the following effects: by adopting an organic synthesis process, the production cost is greatly reduced, the concentration of a target product after the synthesis reaction is high, the extraction is convenient, the product quality is improved, the purity is more than or equal to 99.5 percent, and the product can reach the enterprise standard of British synthetic chemical company:
thiophene,% by weight 99.5
Density (20 ℃ C.) 1.065
Carbon disulfide,% by weight, 0.1
Colorless liquid in appearance
Aromatic odor with characteristic odor
Water content,% (by weight) 0.03
Drawings
FIG. 1 is a schematic flow chart of a production apparatus of the present invention.
Detailed Description
FIG. 1 does not include preheating of the gas phase 1, 3-butadiene and the conversion of solid sulfur to gas phase sulfur.
The liquid 1, 3-butadiene is pumped into the preheating vaporizer through a metering pump, an electric heater is adopted for heating, and the temperature is controlled to be 180-240 ℃. Steam is injected into the preheating vaporizer according to the mol ratio of 1-3: 1(1, 3-butadiene: steam) to prevent the 1, 3-butadiene from polymerizing at high temperature.
And putting the solid flaky sulfur into a melting tank in batches, heating, controlling the temperature in the melting tank to be 120-150 ℃, and feeding the solid flaky sulfur into a sulfur metering pump. The liquid sulfur is pumped into the vaporizer by a metering pump, an electric heater is adopted for heating, and the temperature of the vaporizer is controlled to be 440-470 ℃.
Mixing gas-phase sulfur and 1, 3-butadiene gas according to the weight ratio of 1.04-1.33: 1, and feeding the mixture into a tubular reactor. The temperature of the reactor is controlled to be 250-550 ℃, preferably 380-480 ℃, the pressure is 0.05-0.25 Mpa (gauge pressure), the reaction linear speed is 1.5-3.0 m/s (meter/second), and the reaction time is 1-3 seconds.
Stainless steel pall ring random packing is filled in the tubular reactor, and a jacket type electric heater is adopted to heat the outside of the tubular reactor. In the reaction process, a small amount of water vapor can be injected into the reactor to keep the reaction temperature in the reactor uniform.
And (3) allowing the reaction product to enter a reaction settling tank from the tubular reactor, cooling the temperature to 250-350 ℃, and intermittently discharging a small amount of heavy tar (reaction by-product) from the reaction settling tank.
The reaction product enters a single-tube-pass vertical condensation cooler from a reaction settling tank through a settling tube, the temperature of a gas phase inlet of the condenser is generally 95-150 ℃, and the gas-liquid two-phase reaction product cooled to 40-50 ℃ enters a three-phase separator.
Natural settling separation is carried out in the three-phase separator, non-condensable gas (tail gas rich in hydrogen sulfide) is separated from the top, and the tail gas is subjected to two-stage alkali washing and desulfurization by adesulfurization catalyst bed layer according to a known technology, so that the content of the hydrogen sulfide in the tail gas finally discharged at high altitude is not more than 2 ppm. Repeatedly absorbing the sodium sulfide by 35-42% sodium hydroxide solution to form sodium sulfide (Na) with the concentration of 40% at the bottom of the absorption tower2S, NaHS) solution, which can be sold as a by-product.
In the middle of the three-phase separator, a small amount of sulfur-containing sewage (a small amount of water vapor injected into the reactor) is separated out, enters a closed storage tank and is periodically transported to an oil refinery for sewage treatment and unified treatment.
The semi-finished product liquid is separated from the lower part of the water dividing hopper of the three-phase separator and flows into a semi-finished product storage tank under self pressure (wherein the content of thiophene is 40-50%).
And feeding the semi-finished product liquid into an intermittent high-efficiency rectifying tower. The temperature of a tower kettle is controlled to be 80-20 ℃, the number of theoretical plates of the rectifying column is about 80, the reflux ratio of the tower top is controlled to be 3-10, and distillate before 83 ℃ is cut into an unqualified tank (accounting for about 8-15% of the feeding material of the rectifying column). Analyzing the purity of distillate thiophene by gas chromatography, and cutting the distillate thiophene into a qualified tank after the purity is more than or equal to 99.5%, wherein the temperature of the top of the tower is 83.5-84.5 ℃. When the temperature of the tower top is close to 85 ℃, the distillate components are detected in time, the unqualified tank is cut into, and the rectification operation is stopped.
Pumping the residue in the distillation tower kettle into a light tar tank through a pump, and selling the residue as a byproduct (accounting for about 40-50% of the feed of the distillation tower)
Packaging: filtering the solution in the qualified tank, and loading the solution into a galvanized iron cylinder.
Referring to material balance, taking 15kg/h thiophene as a benchmark:
feeding: 32kg/h of sulfur
27kg/h of 1, 3-butadiene
Steam 35kg/h
Totaling: 94kg/h
Discharging: thiophene 15kg/h
21kg/h of tail gas
Tar (including light tar and heavy tar) 19kg/h
4kg/h of carbon disulfide and the like
35kg/h of sulfur-containing sewage
Totaling: 94kg/h
Claims (9)
1. Thiophene synthesis process, characterized in that gas phase sulphur and 1, 3-butadiene are reacted, and thiophene is extracted from the reaction gas product.
2. The process of claim 1, wherein the sulfur is reacted with 1, 3-butadiene in the absence of a catalyst at a temperature of 250 to 550 ℃ and a gauge pressure of 0.05 to 0.25 MPa.
3. The process according to claim 2, wherein the reaction temperature of the sulfur and 1, 3-butadiene is 380 to 480 ℃.
4. The process according to claim 2, wherein the linear reaction rate is 1.5 to 3.0m/s and the reaction time is 1 to 3 seconds.
5. The process according to claim 2, wherein the weight ratio of the gas-phase sulfur to 1, 3-butadiene is 1.04 to 1.33: 1.
6. The process as claimed in claim 2, wherein the reaction temperature is controlled by adding a small amount of water vapor during the reaction.
7. The process as claimed in claim 1, wherein the temperature of the reaction gas product is reduced to 250-350 ℃, heavy oil in the reaction by-products is removed, then the reaction gas product is condensed and cooled to 40-50 ℃, tail gas, sulfur-containing sewage and semi-finished product liquid three-phase substances in the reaction product are separated, semi-finished product liquid substances are rectified, and 83.5-84.5 ℃ fractions are collected, namely thiophene.
8. The process as claimed in claim 7, wherein the semi-finished product liquid is carried out in a rectification column, and the temperature of the column bottom is controlled to be 80-120 ℃.
9. The apparatus for producing thiophene according to claim 1, comprising a tubular reactor, a reaction settling tank connected to the tubular reactor, a vertical settling tube connected to the reaction settling tank, and a vertical condensing cooler connected to the vertical settling tube, wherein an outlet of the condensing cooler is connected to a three-phase separator, a semi-finished product storage tank is connected to a lower portion of the three-phase separator, and the storage tank is connected to a batch fractionating tower.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01135132 CN1420116A (en) | 2001-11-20 | 2001-11-20 | Process and apparatus for synthesis of thiophene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01135132 CN1420116A (en) | 2001-11-20 | 2001-11-20 | Process and apparatus for synthesis of thiophene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1420116A true CN1420116A (en) | 2003-05-28 |
Family
ID=4672976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 01135132 Pending CN1420116A (en) | 2001-11-20 | 2001-11-20 | Process and apparatus for synthesis of thiophene |
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| CN (1) | CN1420116A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101654449A (en) * | 2009-09-11 | 2010-02-24 | 连云港宏业化工有限公司 | Method and device for producing thiophene and derivant thereof |
| CN101654450B (en) * | 2009-09-11 | 2012-11-21 | 连云港宏业化工有限公司 | Method and device for producing thiophene and derivative thereof in direct-cooled mode |
| CN106946845A (en) * | 2017-03-06 | 2017-07-14 | 山西恒强化工有限公司 | A kind of synthesizer of 2 bromothiophene |
| CN111939849A (en) * | 2020-09-08 | 2020-11-17 | 泰安科赛尔化学科技有限公司 | Thiophene production cyclic recycling system |
| CN111957260A (en) * | 2020-09-08 | 2020-11-20 | 泰安科赛尔化学科技有限公司 | Thiophene production mixer and production mixer assembly thereof |
| CN113801093A (en) * | 2021-10-08 | 2021-12-17 | 湖北特腾新材料技术有限公司 | A kind of production method and equipment of 3-methylthiophene |
| CN114773311A (en) * | 2022-05-12 | 2022-07-22 | 山东省科学院菏泽分院 | Preparation method of thiophene |
| WO2024250191A1 (en) * | 2023-06-07 | 2024-12-12 | 淄博琛博化工有限公司 | Improved process for synthesizing thiophene from butadiene and sulfur |
-
2001
- 2001-11-20 CN CN 01135132 patent/CN1420116A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101654449A (en) * | 2009-09-11 | 2010-02-24 | 连云港宏业化工有限公司 | Method and device for producing thiophene and derivant thereof |
| CN101654450B (en) * | 2009-09-11 | 2012-11-21 | 连云港宏业化工有限公司 | Method and device for producing thiophene and derivative thereof in direct-cooled mode |
| CN101654449B (en) * | 2009-09-11 | 2013-03-13 | 连云港宏业化工有限公司 | Method and device for producing thiophene and derivant thereof |
| CN106946845A (en) * | 2017-03-06 | 2017-07-14 | 山西恒强化工有限公司 | A kind of synthesizer of 2 bromothiophene |
| CN111939849A (en) * | 2020-09-08 | 2020-11-17 | 泰安科赛尔化学科技有限公司 | Thiophene production cyclic recycling system |
| CN111957260A (en) * | 2020-09-08 | 2020-11-20 | 泰安科赛尔化学科技有限公司 | Thiophene production mixer and production mixer assembly thereof |
| CN113801093A (en) * | 2021-10-08 | 2021-12-17 | 湖北特腾新材料技术有限公司 | A kind of production method and equipment of 3-methylthiophene |
| CN114773311A (en) * | 2022-05-12 | 2022-07-22 | 山东省科学院菏泽分院 | Preparation method of thiophene |
| CN114773311B (en) * | 2022-05-12 | 2022-12-23 | 山东省科学院菏泽分院 | Preparation method of thiophene |
| WO2024250191A1 (en) * | 2023-06-07 | 2024-12-12 | 淄博琛博化工有限公司 | Improved process for synthesizing thiophene from butadiene and sulfur |
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