CN101941928A - Synthesis method of sulfhydryl alkyl alcohol - Google Patents
Synthesis method of sulfhydryl alkyl alcohol Download PDFInfo
- Publication number
- CN101941928A CN101941928A CN2010102517550A CN201010251755A CN101941928A CN 101941928 A CN101941928 A CN 101941928A CN 2010102517550 A CN2010102517550 A CN 2010102517550A CN 201010251755 A CN201010251755 A CN 201010251755A CN 101941928 A CN101941928 A CN 101941928A
- Authority
- CN
- China
- Prior art keywords
- hydrogen sulfide
- acid gas
- catalyzer
- solvent
- mercaptoalkyl alcohol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a synthesis method of sulfhydryl alkyl alcohol, belonging to the field of synthesis of compounds. The invention solves the problems of high equipment investment, high energy consumption and low added value of sulfur in the prior Kraus process for processing hydrogen sulfide. The method comprises the following steps: 1. dehydrating byproduct acid gas containing the hydrogen sulfide, and dissolving the hydrogen sulfide in the acid gas into a catalyst solution to obtain a catalyst solvent containing the hydrogen sulfide; and 2. introducing epoxy compounds and catalyst solvent containing the hydrogen sulfide into a reactor to carry out synthesis, rectifying, separating, and distilling under reduced pressure to obtain the sulfhydryl alkyl alcohol. In the invention, after the hydrogen sulfide waste gas is purified, the catalyst solution is used for directly absorbing the hydrogen sulfide and then participates in the synthetic reaction, thereby saving the energy consumption needed in the deabsorption process; and meanwhile, by using the hydrogen sulfide as one of raw materials, the method lowers the production cost for subsequent products and increases the added value of sulfhydryl alkyl alcohol. The method has the advantages of low investment, low raw material consumption and the like, and obviously lowers the production cost.
Description
Technical field
The invention belongs to the synthetic field of compound, and a kind of environmental protection utilization of resources field that utilizes waste gas to produce fine chemical product, be specifically related to a kind of mercaptoalkyl alcohol synthetic method.
Background technology
Hydrogen sulfide results from the right gas of Tian Jingization ﹑ refining of petroleum, and production process such as Zhi Mei Qi ﹑ Zhi Ge ﹑ Zhi Yao ﹑ Zao Zhi ﹑ synthetic chemistry fiber.Hydrogen sulfide is colourless gas, and the pungency stench is arranged, and is volatile, is blue flame during burning.
Hydrogen sulfide is one of atmospheric principal pollutant, not only is detrimental to health, also can severe corrosion equipment etc.Handling the sophisticated method of hydrogen sulfide is that Ke Louth Fa ﹕ is oxidized to sulfurous gas to 1/3 hydrogen sulfide earlier, and it is reacted with residue hydrogen sulfide in converter, can directly produce molten sulfur from gas phase.This method is desirable from the environmental protection aspect, but from being non-remunerative economically.Because Kraus process needs bigger equipment input, consume a large amount of energy simultaneously, obtain the very low sulphur of added value.
The shortcoming that the Kraus process of handling at present hydrogen sulfide exists equipment has high input, product sulphur added value is low problem and hydrogen sulfide desorption process need consume big energy.
Summary of the invention
Purpose of the present invention has high input for there is equipment in the Kraus process that solves present processing hydrogen sulfide, the energy consumption height, the problem that product sulphur added value is low; And provide a kind of mercaptoalkyl pure synthetic method.
Mercaptoalkyl alcohol synthetic method is undertaken by following step among the present invention: mercaptoalkyl alcohol synthetic method is undertaken by following step: one, the by product acid gas that will contain hydrogen sulfide compresses cooled dehydrated (perhaps compress cooled dehydrated after adsorption dry), be that 0.01% ~ 90% catalyst solution absorbs the hydrogen sulfide in the acid gas with mass concentration then, hydrogen sulfide is 1:1 ~ 10 with catalyzer solvent quality ratio, obtain hydrogen sulfide containing catalyzer solvent, catalyzer is an organic amine in the described catalyst solution, the causticity bases, molecular sieve or strongly basic anion exchange resin, solvent is the low-carbon (LC) alcohols in the catalyst solution, mercaptoalkyl alcohol or sulfo-glycol ether class; Two, be that the ratio of 1:1.01 ~ 1.2 feeds in the tubular reactor with epoxy compounds and hydrogen sulfide containing catalyzer solvent in the mass ratio of epoxy compounds and hydrogen sulfide, under 30 ~ 50 ℃ of conditions, react 30 ~ 50min, rectifying separation goes out solvent, catalyzer and excessive hydrogen sulfide then, obtains mercaptoalkyl alcohol again after the rectification under vacuum.
After the present invention carried out purifying treatment by dehydration (after drying perhaps dewaters) to hydrogen sulfide waste gas, hydrogen sulfide did not need to desorb from the catalyzer solvent, directly participated in the building-up reactions of back as raw material, had saved the desorb process need and had consumed lot of energy; Simultaneously, hydrogen sulfide has reduced the subsequent product production cost as one of raw material, improved the economic benefit that hydrogen sulfide utilizes, go out solvent, catalyzer and excessive hydrogen sulfide through rectifying separation, solvent, catalyzer recycle as the acid gas cleaning treatment medium, and excessive hydrogen sulfide recycles as raw material; The inventive method has less investment, and the raw material consumption quota is low, advantages such as the remarkable reduction of production cost.Mercaptoalkyl such as mercaptoethanol, mercaprol alcohol is important fine chemical product, main as the telogen of macromolecular materials such as polyacrylonitrile, polystyrene, polyacrylic ester and polymerizing catalyst, linking agent and the resin curing agent of Polymer Synthesizing, it is the intermediate of producing dyestuff, spices and agricultural chemicals, the raw material of medicine industry and photochemistry industry, the auxiliary agent of industries such as rubber, weaving, paint also can be done metal inhibitor and passivator.
Description of drawings
Fig. 1 is the color atlas of embodiment nine preparation mercaptoethanols.
Embodiment
Embodiment one: mercaptoalkyl alcohol synthetic method is undertaken by following step in the present embodiment: one, the by product acid gas that will contain hydrogen sulfide compresses cooled dehydrated (perhaps compress cooled dehydrated after adsorption dry), be that 0.01% ~ 90% catalyst solution absorbs the hydrogen sulfide in the acid gas with mass concentration then, hydrogen sulfide is 1:1 ~ 10 with catalyzer solvent quality ratio, obtain hydrogen sulfide containing catalyzer solvent, catalyzer is an organic amine in the described catalyst solution, the causticity bases, molecular sieve or strongly basic anion exchange resin, solvent is the low-carbon (LC) alcohols in the catalyst solution, mercaptoalkyl alcohol or sulfo-glycol ether class; Two, be that the ratio of 1:1.01 ~ 1.2 feeds in the tubular reactor with epoxy compounds and hydrogen sulfide containing catalyzer solvent in the mass ratio of epoxy compounds and hydrogen sulfide, under 30 ~ 50 ℃ of conditions, react 30 ~ 50min, rectifying separation goes out solvent, catalyzer and excessive hydrogen sulfide then, obtains mercaptoalkyl alcohol again after the rectification under vacuum.
Oxyethane transformation efficiency 100% in the present embodiment, the mercaptoethanol selectivity is greater than 90%.
Embodiment two: what present embodiment and embodiment one were different is: the by product acid gas that contains hydrogen sulfide in the step 1 is that selexol process purifies by product acid gas or refining of petroleum desulfurization by-product acid gas.Other step is identical with embodiment one with parameter.
Embodiment three: what present embodiment was different with embodiment one or two is: adopt spray absorption tower or hypergravity absorption reactor thermally that the hydrogen sulfide in the acid gas is dissolved in the catalyst solution in the step 1.Other step is identical with embodiment one or two with parameter.
Embodiment four: what present embodiment was different with one of embodiment one to three is: organic amine is a Monoethanolamine MEA BASF, diethanolamine, trolamine, Trimethylamine 99, triethylamine or tripropyl amine, the causticity bases is a sodium hydroxide, lithium hydroxide, potassium hydroxide or calcium hydroxide, molecular sieve is the 3A molecular sieve, the 4A molecular sieve, the 5A molecular sieve, 13X molecular sieve or 10X molecular sieve, strongly basic anion exchange resin are 7170 strong-basicity styrene series anion exchange resins, 717 strongly basic anion exchange resins, 711 strongly basic anion exchange resins, D201 macroporous strong basic styrene series anionite-exchange resin or strong-basicity styrene anionite-exchange resin amberjet 4400.Other step is identical with one of embodiment one to three with parameter.
The described molecular sieve of present embodiment, strongly basic anion exchange resin sieve are the commercial goods.
Embodiment five: what present embodiment was different with one of embodiment one to four is: the low-carbon (LC) alcohols is methyl alcohol, ethanol, propyl alcohol or Virahol in the step 1, mercaptoalkyl alcohol is mercaptoethanol or mercaprol, and sulfo-glycol ether class is sulfo-glycol ether or sulfo-triglycol.
Embodiment six: what present embodiment was different with one of embodiment one to four is: the structural formula of the described epoxy compounds of step 2 is in the step 1
, R
1Be H, alkyl, alkoxyl group, hydroxyalkyl, chloro alkyl or aryl; R
2Be H, alkyl, alkoxyl group, hydroxyalkyl, chloro alkyl or aryl.Other step is identical with one of embodiment one to five with parameter.
The mercaptoalkyl alcohol structural formula that present embodiment obtains is:
Embodiment seven: what present embodiment and embodiment six were different is: described alkyl is methyl, ethyl or propyl group, alkoxyl group is methoxyl group, oxyethyl group or propoxy-, hydroxyalkyl is methylol, hydroxyethyl or hydroxypropyl, the chloro alkyl is chloro methyl, chloro ethyl or chloro propyl group, and aryl is phenmethyl, styroyl, hydrocinnamyl, tolyl or ethylbenzene base.Other step is identical with embodiment six with parameter.
Embodiment eight: present embodiment is different with one of embodiment one to seven: in the step 2 rectification under vacuum is to carry out under 6.0KPa, 67 ~ 69 ℃ of conditions of temperature at pressure.Other step is identical with one of embodiment one to seven with parameter.
Embodiment nine: purifying the by-product acid gas with selexol process in the present embodiment is the synthetic mercaptoethanol of raw material, and concrete synthetic method is undertaken by following step: (acid gas the typical case form: H one, selexol process to be purified the by-product acid gas
2S 92%; CO
26%; Hydro carbons 2% (butt)) compresses cooled dehydrated, be that 50% catalyst solution absorbs the hydrogen sulfide in the acid gas with mass concentration then, hydrogen sulfide is 1:5 with catalyzer solvent quality ratio, obtain hydrogen sulfide containing catalyzer solvent, catalyzer is a diethanolamine in the described catalyst solution, and solvent is an ethanol in the catalyst solution; Two, be that the ratio of 1:1.2 feeds in the tubular reactor with oxyethane and hydrogen sulfide containing catalyzer solvent in the mass ratio of oxyethane and hydrogen sulfide, under 45 ℃ of conditions, react 40min, rectifying separation goes out solvent, catalyzer and excessive hydrogen sulfide then, is that 6.0KPa, temperature are to obtain mercaptoethanol after the rectification under vacuum under 67 ~ 69 ℃ of conditions at pressure again.
Reactional equation is as follows in the present embodiment:
Main reaction: H
2S+CH
2CH
2O==HSCH
2CH
2OH+Q1
Side reaction: H
2S+2 CH
2CH
2O==S(CH
2CH
2OH)
2+ Q2
HSCH
2CH
2OH?+?CH
2CH
2O?==?S（CH
2CH
2OH）
2?+?Q3
The mercaptoethanol yield is greater than 90% in the present embodiment.
Mercaptoethanol to the present embodiment preparation carries out check and analysis, and the instrument and the condition that detect usefulness are as follows:
Chromatographic instrument: GC-13A
Detector: thermal conductivity cell
Chromatographic column: 2mm * 1 m stainless steel packed column
Stationary phase: GDX-401, the 60-80 order
Column temperature: 170 ℃
Vaporizer temperature: 220 ℃
Detector temperature: 220 ℃
Bridge stream: 150 mA
Carrier gas: High Purity Hydrogen
Carrier gas flux: 50 mL/min
Sample size: 0.5 microlitre
Detected result compares with the mercaptoethanol standard substance as shown in Figure 1, retention time and reaction solution 4#(
β-M) component retention time unanimity, prove that it is the mercaptoethanol (see figure 1) that the present embodiment method makes reaction product.
Embodiment ten: be the synthetic mercaptoethanol of raw material with refining of petroleum desulfurization by-product acid gas in the present embodiment; Refining of petroleum desulfurization acid gas is formed: H
2S 45 ~ 95%; CO
250 ~ 2%%; Hydro carbons 5 ~ 3% (butt); Other is identical with embodiment nine with step and parameter.
The mercaptoethanol yield is greater than 90% in the present embodiment.
Embodiment 11: purifying the by-product acid gas with selexol process in the present embodiment is the synthetic mercaptoethanol of raw material, and concrete synthetic method is undertaken by following step: (acid gas the typical case form: H one, selexol process to be purified the by-product acid gas
2S 92%; CO
26%; Hydro carbons 2% (butt)) compresses cooled dehydrated, be that 60% catalyst solution absorbs the hydrogen sulfide in the acid gas with mass concentration then, hydrogen sulfide is 1:3 with catalyzer solvent quality ratio, obtain hydrogen sulfide containing catalyzer solvent, catalyzer is the 3A molecular sieve in the described catalyst solution, and solvent is the sulfo-glycol ether in the catalyst solution; Two, be that the ratio of 1:1 ~ 1.2 feeds in the tubular reactor with propylene oxide and hydrogen sulfide containing catalyzer solvent in the mass ratio of oxyethane and hydrogen sulfide, under 30 ~ 50 ℃ of conditions, react 30 ~ 50 min, rectifying separation goes out solvent, catalyzer and excessive hydrogen sulfide then, is to obtain mercaptoethanol after the rectification under vacuum under 0.2KPa, 60 ~ 62 ℃ of conditions of temperature at pressure again.
Propylene oxide transformation efficiency 100% in the present embodiment, the mercaprol selectivity is greater than 90%.
Claims (9)
1. mercaptoalkyl alcohol synthetic method, it is characterized in that mercaptoalkyl alcohol synthetic method undertaken by following step: one, the by product acid gas that will contain hydrogen sulfide compresses cooled dehydrated, be that 0.01% ~ 90% catalyst solution absorbs the hydrogen sulfide in the acid gas with mass concentration then, hydrogen sulfide is 1:1 ~ 10 with catalyzer solvent quality ratio, obtain hydrogen sulfide containing catalyzer solvent, catalyzer is an organic amine in the described catalyst solution, the causticity bases, molecular sieve or strongly basic anion exchange resin, solvent is the low-carbon (LC) alcohols in the catalyst solution, mercaptoalkyl alcohol or sulfo-glycol ether class; Two, be that the ratio of 1:1.01 ~ 1.2 feeds in the tubular reactor with epoxy compounds and hydrogen sulfide containing catalyzer solvent in the mass ratio of epoxy compounds and hydrogen sulfide, under 30 ~ 50 ℃ of conditions, react 30 ~ 50min, rectifying separation goes out solvent, catalyzer and excessive hydrogen sulfide then, obtains mercaptoalkyl alcohol again after the rectification under vacuum.
2. a kind of mercaptoalkyl alcohol synthetic method according to claim 1, the by product acid gas that it is characterized in that containing in the step 1 hydrogen sulfide is that selexol process purifies by product acid gas or refining of petroleum desulfurization by-product acid gas.
3. a kind of mercaptoalkyl alcohol synthetic method according to claim 1 and 2 is characterized in that adopting in the step 1 spray absorption tower or hypergravity absorption reactor thermally that the hydrogen sulfide in the acid gas is dissolved in the catalyst solution.
4. a kind of mercaptoalkyl alcohol synthetic method according to claim 3, it is characterized in that organic amine is a Monoethanolamine MEA BASF in the step 1, diethanolamine, trolamine, Trimethylamine 99, triethylamine or tripropyl amine, the causticity bases is a sodium hydroxide, lithium hydroxide, potassium hydroxide or calcium hydroxide, molecular sieve is the 3A molecular sieve, the 4A molecular sieve, the 5A molecular sieve, 13X molecular sieve or 10X molecular sieve, strongly basic anion exchange resin are 7170 strong-basicity styrene series anion exchange resins, 717 strongly basic anion exchange resins, 711 strongly basic anion exchange resins, D201 macroporous strong basic styrene series anionite-exchange resin or strong-basicity styrene anionite-exchange resin amberjet 4400.
5. according to claim 1,2 or 4 described a kind of mercaptoalkyl alcohol synthetic methods, it is characterized in that the low-carbon (LC) alcohols is methyl alcohol, ethanol, propyl alcohol or Virahol in the step 1, mercaptoalkyl alcohol is mercaptoethanol or mercaprol, and sulfo-glycol ether class is sulfo-glycol ether or sulfo-triglycol.
6. a kind of mercaptoalkyl alcohol synthetic method according to claim 5 is characterized in that the structural formula of the described epoxy compounds of step 2 in the step 1 is
, R
1Be H, alkyl, alkoxyl group, hydroxyalkyl, chloro alkyl or aryl; R
2Be H, alkyl, alkoxyl group, hydroxyalkyl, chloro alkyl or aryl.
7. a kind of mercaptoalkyl alcohol synthetic method according to claim 6, it is characterized in that described alkyl is methyl, ethyl or propyl group, alkoxyl group is methoxyl group, oxyethyl group or propoxy-, hydroxyalkyl is methylol, hydroxyethyl or hydroxypropyl, the chloro alkyl is chloro methyl, chloro ethyl or chloro propyl group, and aryl is phenmethyl, styroyl, hydrocinnamyl, tolyl or ethylbenzene base.
8. according to claim 1,2,4,6 or 7 described a kind of mercaptoalkyl alcohol synthetic methods, it is characterized in that rectification under vacuum is to carry out under 6.0KPa, 67 ~ 69 ℃ of conditions of temperature at pressure in the step 2.
9. mercaptoalkyl alcohol synthetic method, it is characterized in that mercaptoalkyl alcohol synthetic method undertaken by following step: one, the by product acid gas that will contain hydrogen sulfide compresses adsorption dry after the cooled dehydrated, with mass concentration is that 0.01% ~ 90% catalyst solution absorbs the hydrogen sulfide in the acid gas, hydrogen sulfide is 1:1 ~ 10 with catalyzer solvent quality ratio, obtain hydrogen sulfide containing catalyzer solvent, catalyzer is an organic amine in the described catalyst solution, the causticity bases, molecular sieve or strongly basic anion exchange resin, solvent is the low-carbon (LC) alcohols in the catalyst solution, mercaptoalkyl alcohol or sulfo-glycol ether class; Two, be that the ratio of 1:1.01 ~ 1.2 feeds in the tubular reactor with epoxy compounds and hydrogen sulfide containing catalyzer solvent in the mass ratio of epoxy compounds and hydrogen sulfide, under 30 ~ 50 ℃ of conditions, react 30 ~ 50min, rectifying separation goes out solvent, catalyzer and excessive hydrogen sulfide then, obtains mercaptoalkyl alcohol again after the rectification under vacuum.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102517550A CN101941928B (en) | 2010-08-12 | 2010-08-12 | Synthesis method of sulfhydryl alkyl alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102517550A CN101941928B (en) | 2010-08-12 | 2010-08-12 | Synthesis method of sulfhydryl alkyl alcohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101941928A true CN101941928A (en) | 2011-01-12 |
| CN101941928B CN101941928B (en) | 2012-11-21 |
Family
ID=43434165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010102517550A Expired - Fee Related CN101941928B (en) | 2010-08-12 | 2010-08-12 | Synthesis method of sulfhydryl alkyl alcohol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101941928B (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103331075A (en) * | 2013-07-12 | 2013-10-02 | 湖北兴发化工集团股份有限公司 | Tail gas absorption method and tail gas absorption device of dimethyl sulfide |
| CN104910054A (en) * | 2015-04-20 | 2015-09-16 | 济南大学 | High-selectivity colorimetric ratio method for determining Hg<2+> in pure water system |
| CN105399651A (en) * | 2015-12-03 | 2016-03-16 | 黄河三角洲京博化工研究院有限公司 | Method for continuously synthesizing thiodiglycol |
| US9718767B2 (en) | 2015-12-04 | 2017-08-01 | Chevron Phillips Chemical Company Lp | Beta-mercaptoethanol synthesis |
| US10689333B1 (en) | 2019-02-22 | 2020-06-23 | Chevron Phillips Chemical Company Lp | 2-mercaptoethanol synthesis |
| CN113634087A (en) * | 2021-10-18 | 2021-11-12 | 山东德仕石油装备有限公司 | Method and device for obtaining CO2 from outlet of oil production well in carbon dioxide oil production method |
| CN115521231A (en) * | 2022-09-23 | 2022-12-27 | 天宝动物营养科技股份有限公司 | Environment-friendly clean preparation method of taurine |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1290696A (en) * | 1999-10-03 | 2001-04-11 | 赵珉 | Process for producing mercaptoethanol from waste natural gas |
| JP2008013453A (en) * | 2006-07-04 | 2008-01-24 | Sumitomo Chemical Co Ltd | Method for producing 2-mercaptoethanol |
| EP1923384A1 (en) * | 2006-11-09 | 2008-05-21 | Basf Se | Method for manufacturing 2-mercapto ethanol |
-
2010
- 2010-08-12 CN CN2010102517550A patent/CN101941928B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1290696A (en) * | 1999-10-03 | 2001-04-11 | 赵珉 | Process for producing mercaptoethanol from waste natural gas |
| JP2008013453A (en) * | 2006-07-04 | 2008-01-24 | Sumitomo Chemical Co Ltd | Method for producing 2-mercaptoethanol |
| EP1923384A1 (en) * | 2006-11-09 | 2008-05-21 | Basf Se | Method for manufacturing 2-mercapto ethanol |
Non-Patent Citations (1)
| Title |
|---|
| 吕楠: "2-巯基乙醇的合成技术进展与市场需求", 《化工中间体》 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103331075A (en) * | 2013-07-12 | 2013-10-02 | 湖北兴发化工集团股份有限公司 | Tail gas absorption method and tail gas absorption device of dimethyl sulfide |
| CN104910054A (en) * | 2015-04-20 | 2015-09-16 | 济南大学 | High-selectivity colorimetric ratio method for determining Hg<2+> in pure water system |
| CN105399651A (en) * | 2015-12-03 | 2016-03-16 | 黄河三角洲京博化工研究院有限公司 | Method for continuously synthesizing thiodiglycol |
| US9718767B2 (en) | 2015-12-04 | 2017-08-01 | Chevron Phillips Chemical Company Lp | Beta-mercaptoethanol synthesis |
| US10544094B2 (en) | 2015-12-04 | 2020-01-28 | Chevron Philips Chemical Company, Lp | Beta-mercaptoethanol synthesis |
| US10689333B1 (en) | 2019-02-22 | 2020-06-23 | Chevron Phillips Chemical Company Lp | 2-mercaptoethanol synthesis |
| CN113634087A (en) * | 2021-10-18 | 2021-11-12 | 山东德仕石油装备有限公司 | Method and device for obtaining CO2 from outlet of oil production well in carbon dioxide oil production method |
| CN115521231A (en) * | 2022-09-23 | 2022-12-27 | 天宝动物营养科技股份有限公司 | Environment-friendly clean preparation method of taurine |
| CN115521231B (en) * | 2022-09-23 | 2024-02-09 | 天宝动物营养科技股份有限公司 | Environment-friendly clean preparation method of taurine |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101941928B (en) | 2012-11-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101941928B (en) | Synthesis method of sulfhydryl alkyl alcohol | |
| Xiong et al. | The efficient conversion of H 2 S into mercaptan alcohols mediated in protic ionic liquids under mild conditions | |
| CN102728331B (en) | Preparation method of metal-organic framework material for adsorbing separation of carbon dioxide/ methane | |
| CN113214038B (en) | Method for separating benzene-n-propanol-water mixture by heat pump extractive distillation | |
| CN104610087A (en) | Device and method for purifying yellow phosphorus tail gas and continuously synthesizing oxamide | |
| CN1699359A (en) | Process for preparing cyclic alkyl carbonate | |
| CN111185205B (en) | Supported catalyst and application thereof in preparation of hydroxyalkyl acrylate | |
| CN113019107A (en) | Method for oxidizing hydrogen sulfide and removing carbon dioxide by iron-based ionic liquid wet method | |
| CN108033943A (en) | A kind of preparation method of fluorinated ethylene carbonate | |
| CN101829475A (en) | Polyamine flue gas desulfurizer and preparation method thereof | |
| CN100513403C (en) | Method for preparing cyclic carbonate by using catalysis of periodic usable functional polyglycol | |
| CN105645514A (en) | Method for separating and purifying ammonium sulfate and sodium sulfate mixed solution during flue gas desulfurizer regeneration | |
| CN102515104A (en) | Method for preparing hydrogen chloride and silicon dioxide by hydrolyzing silicon tetrachloride in organic solvent | |
| CN108439350B (en) | Regeneration method of waste thionyl chloride | |
| CN101709055A (en) | Method for synthesizing ionic liquid | |
| CN106831527A (en) | Pyrroles and preparation method thereof | |
| CN114345084A (en) | Device and method for absorbing methyl chloride in waste gas by ionic liquid at low temperature and variable pressure | |
| CN101747239B (en) | Method for separating and refining trifluoro-methanesulfonyl fluoride CF3SO2 | |
| CN107573252B (en) | Method for recycling wastewater generated in process of producing glycine by chloroacetic acid method | |
| CN111410182A (en) | Method for recycling phosphorus pentafluoride in lithium hexafluorophosphate synthesis tail gas | |
| CN110180327A (en) | A kind of method and system of the tail gas resource utilization containing organic amine | |
| CN210544208U (en) | Tail gas treatment device | |
| CN220968646U (en) | Device for purifying hydrogen sulfide and recycling excessive hydrogen | |
| CN218145875U (en) | Production device for preparing chlorine by byproduct hydrogen chloride | |
| CN117339356B (en) | Copper phthalocyanine synthesis tail gas treatment method and system |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20121121 Termination date: 20140812 |
|
| EXPY | Termination of patent right or utility model |