CN104557457A - Reactive distillation method and reactive distillation device for producing butanol by hydrogenating butyraldehyde - Google Patents
Reactive distillation method and reactive distillation device for producing butanol by hydrogenating butyraldehyde Download PDFInfo
- Publication number
- CN104557457A CN104557457A CN201410713043.4A CN201410713043A CN104557457A CN 104557457 A CN104557457 A CN 104557457A CN 201410713043 A CN201410713043 A CN 201410713043A CN 104557457 A CN104557457 A CN 104557457A
- Authority
- CN
- China
- Prior art keywords
- reactive distillation
- tower
- butanols
- distillation column
- butanol
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a reactive distillation method and a reactive distillation device for producing butanol by hydrogenating butyraldehyde. The device comprises an evaporator, a reactive distillation tower, a butanol distillation tower, an n-butanol and iso-butanol separation tower, a condenser, a reboiler, a compressor, a pump, relevant feeding pipelines and pipelines used for connecting the devices. The method and the device have the characteristics that the reactive distillation technology and devices are adopted, light components are separated at a tower top during a process of carrying out hydrogenation reaction of butyraldehyde in the reactive distillation tower; n-butanol and iso-butanol can be prepared by subsequent separation; a unit for producing butanol by using butyraldehyde and a unit for purifying, distilling and separating are operated and coupled in one device for simultaneously operating; reaction products are purified after the reaction is completed; the device investment is saved; the subsequent operation fee is also reduced; the quality purity of n-butanol prepared by separating through the subsequent butanol distillation tower and the n-butanol and iso-butanol separation tower can reach 99.5%; the quality purity of iso-butanol can reach 99%.
Description
Technical field
The present invention relates to production of butanol technical field, particularly relate to reactive distillation method and device that a kind of butyraldehyde hydrogenation produces butanols.
Background technology
Butanols is important basic organic chemical industry raw material, main application is the raw material as resin, paint, sizing agent and softening agent, also can be used as the extraction agent of grease, spices and medicine and the additive of phthalic resin coating, can be used as the raw material of ore dressing defoamer, washing composition, dewatering agent and synthetic perfume in addition.
The mode of production of butanols can be divided into fermentation method, Acetaldehyde and oxo synthesis.Due to fermentation method and Acetaldehyde technical process long, equipment corrosion is serious, and extremely uneconomical, existing apparatus is substantially superseded.The main method of current production of butanol take propylene as feedstock carbonyl synthesis method synthesis butyraldehyde, then produce butanols by butyraldehyde hydrogenation.CN1221723A discloses a kind of method that aldehyde gas phase hydrogenation prepares alcohol, treats in the aldehyde of hydrogenation by being joined by nitrogenous alkali, thus suppresses the generation of by product, obtains the alcohol of highly selective and high yield.CN1278237A discloses a kind of method of producing propyl carbinol, under the moisture being less than or equal to about 6 % by weight exists, butyraldehyde-n obtains propyl carbinol reaction product by hydrogenation, and under there is about 0.01-6 % by weight water condition in separation column, purify to product, object is that by product di-n-butyl ether is separated with propyl carbinol with the form of the low azeotropic of ternary.CN102408304A discloses a kind of method that aldehyde selec-tive hydrogenation prepares alcohol, the hydrogenation catalyst containing carrier, metal active constituent and silane group is used in patent, on this catalyzer, the amount of by product can significantly reduce, and has catalyzer long service life, the advantage that carbon distribution is few.
Butyraldehyde hydrogenation reaction is except generating propyl carbinol and isopropylcarbinol, and also a small amount of by product can occur, by product has amylalcohol, octanol, ester and ether etc.At present, to the separation of hydrogenation reaction product, the main lightness-removing column and weight-removing column and positive isobutanol separation column of adopting obtains propyl carbinol product and isobutanol product.Reaction rectification technique applies day by day a kind of process intensification technology simultaneously carried out in same equipment by simultaneous reaction and separation widely in chemical industry, and in facility investment, this technology is also than reacting and being separated the flow process of separate operation more economically.Also reaction rectification technique is not applied in Patents and the report of butyraldehyde Hydrogenation butanols process at present.
Summary of the invention
The object of this invention is to provide a kind of butyraldehyde hydrogenation and produce the reactive distillation method of butanols and device, use catalytic reaction rectification method provided by the invention, the advantage such as have that technical process is simple, facility investment is lower, easy to operate and energy consumption is lower.
Butyraldehyde hydrogenation of the present invention produces reactive distillation method and the device of butanols, and primarily of vaporizer, reactive distillation column, butanols rectifying tower and positive isobutanol separation column composition, main products is propyl carbinol and isopropylcarbinol.The feature of method of the present invention and device is the employing of reaction rectification technique and equipment, light constituent can be isolated by tower top while reactive distillation column carries out butyraldehyde hydrogenation reaction, just can obtained by later separation, isopropylcarbinol, reduce technical process, save facility investment.
Technical scheme of the present invention is as follows:
Butyraldehyde of the present invention produces the reaction and rectification device of butanols, comprises vaporizer, reactive distillation column, butanols rectifying tower, positive isobutanol separation column, condenser, reboiler, compressor, pump and relevant feedstocks pipeline and the pipeline being connected above equipment; Reactive distillation column, butanols rectifying tower, positive isobutanol separation column tower top all arrange condenser, all arrange reboiler at the bottom of reactive distillation column, butanols rectifying tower, positive isobutanol separation column tower; Evaporator overhead gaseous phase outlet is connected to reactive distillation column; Reactive distillation column overhead condenser gaseous phase outlet is connected to compressor, and compressor outlet is connected to reactive distillation column hydrogen feed mouth, and condensator outlet liquid phase, as light component product extraction, is that cymogene alcohol product is connected to butanols rectifying tower opening for feed at the bottom of tower; Butanols rectifying tower ejects material and enters positive isobutanol separation column for mixed butyl alcohol, is heavy constituent by product at the bottom of tower; The discharging of positive isobutanol separation column tower top is isobutanol product, and discharging at the bottom of tower is propyl carbinol product.
The reactive distillation method that butyraldehyde hydrogenation of the present invention produces butanols is: the butyraldehyde gas of raw material butyraldehyde after evaporator vaporization enters the bottom of reactive distillation column conversion zone together with raw hydrogen; Reactive distillation column top gaseous phase enters reactive distillation column overhead condenser, after condensation, gas phase is that the hydrogen of unreacted hydrogen after compressor pressurizes returns reactive distillation column charging, after condensation, liquid phase obtains liquid phase through reactive distillation column reflux-withdrawal pump, control by operating reflux ratio, a part is as phegma, another part is as the extraction of tower top light constituent, and at the bottom of tower, extraction cymogene alcohol is as the charging of butanols rectifying tower; The liquid phase of butanols rectifying tower top gaseous phase after condenser condenses obtains liquid phase through butanols rectifier column reflux extraction pump, control by operating reflux ratio, a part as phegma, another part be mixed butyl alcohol as positive isobutanol separation column charging, extraction heavy constituent by product at the bottom of tower; The liquid phase of positive isobutanol separation column top gaseous phase after condenser condenses obtains liquid phase through positive isobutanol separation column reflux-withdrawal pump, control by operating reflux ratio, a part as phegma, another part as isobutanol product extraction, extraction propyl carbinol product at the bottom of tower.
Butyraldehyde hydrogenation is produced in the reactive distillation method of butanols: evaporator pressure is 0.01-3MPa; Reactive distillation column adopts nickel and/or copper-based catalysts, and conversion zone temperature is 100-250 DEG C, preferred 110-130 DEG C, and pressure is 0.01-2MPa, and reflux ratio is 10-100, and hydrogen aldehyde mol ratio is 10:1-30:1; Butanols rectifying tower pressure is 0.5-1MPa, and reflux ratio is 1-100; Positive isobutanol separation column pressure is 0.1-1MPa, and reflux ratio is 20-100; Pressure all represents by absolute pressure herein.
Butyraldehyde hydrogenation of the present invention produces reactive distillation method and the device of butanols, its advantage is butyraldehyde hydrogenation reaction and butanols purification rectifying separation two unit operations, organically be coupled in an equipment and carry out simultaneously, react and reaction product has been purified simultaneously, both save facility investment, additionally reduce follow-up process cost.The propyl carbinol quality purity obtained after being separated with positive isobutanol separation column by follow-up butanols rectifying tower can reach 99.5%, and the quality purity of isopropylcarbinol can reach 99%.
Embodiment
The present invention is achieved through the following technical solutions:
Butyraldehyde hydrogenation produces the reaction and rectification device of butanols, comprises vaporizer, reactive distillation column, butanols rectifying tower, positive isobutanol separation column, condenser, reboiler, compressor, pump and relevant feedstocks pipeline and the pipeline being connected above equipment; Reactive distillation column, butanols rectifying tower, positive isobutanol separation column tower top all arrange condenser, all arrange reboiler at the bottom of reactive distillation column, butanols rectifying tower, positive isobutanol separation column tower; Evaporator overhead gaseous phase outlet is connected to reactive distillation column; Reactive distillation column overhead condenser gaseous phase outlet is connected to compressor, and compressor outlet is connected to reactive distillation column hydrogen feed mouth, and condensator outlet liquid phase, as light component product extraction, is that cymogene alcohol product is connected to butanols rectifying tower opening for feed at the bottom of tower; Butanols rectifying tower ejects material and enters positive isobutanol separation column for mixed butyl alcohol, is heavy constituent by product at the bottom of tower; The discharging of positive isobutanol separation column tower top is isobutanol product, and discharging at the bottom of tower is propyl carbinol product.
The reactive distillation method that butyraldehyde hydrogenation of the present invention produces butanols is: the butyraldehyde gas of raw material butyraldehyde after evaporator vaporization enters the bottom of reactive distillation column conversion zone together with raw hydrogen; Reactive distillation column top gaseous phase enters reactive distillation column overhead condenser, after condensation, gas phase is that the hydrogen of unreacted hydrogen after compressor pressurizes returns reactive distillation column charging, after condensation, liquid phase obtains liquid phase through reactive distillation column reflux-withdrawal pump, control by operating reflux ratio, a part is as phegma, another part is as the extraction of tower top light constituent, and at the bottom of tower, extraction cymogene alcohol is as the charging of butanols rectifying tower; The liquid phase of butanols rectifying tower top gaseous phase after condenser condenses obtains liquid phase through butanols rectifier column reflux extraction pump, control by operating reflux ratio, a part as phegma, another part be mixed butyl alcohol as positive isobutanol separation column charging, extraction heavy constituent by product at the bottom of tower; The liquid phase of positive isobutanol separation column top gaseous phase after condenser condenses obtains liquid phase through positive isobutanol separation column reflux-withdrawal pump, control by operating reflux ratio, a part as phegma, another part as isobutanol product extraction, extraction propyl carbinol product at the bottom of tower.
Butyraldehyde hydrogenation is produced in the reactive distillation method of butanols: evaporator pressure is 0.01-3MPa; Reactive distillation column adopts nickel and/or copper-based catalysts, and conversion zone temperature is 100-250 DEG C, preferred 110-130 DEG C, and pressure is 0.01-2MPa, and reflux ratio is 10-100, and hydrogen aldehyde mol ratio is 10:1-30:1; Butanols rectifying tower pressure is 0.5-1MPa, and reflux ratio is 1-100; Positive isobutanol separation column pressure is 0.1-1MPa, and reflux ratio is 20-100.
Embodiment 1
In this example, evaporator pressure is 0.01MPa; Reactive distillation column adopts copper-based catalysts, and conversion zone temperature is 250 DEG C, and pressure is 0.01MPa, and reflux ratio is 100, and hydrogen aldehyde mol ratio is 30:1; Butanols rectifying tower pressure is 0.5MPa, and reflux ratio is 100; Positive isobutanol separation column pressure is 0.1MPa, and reflux ratio is 100.Finally obtaining isopropylcarbinol quality purity is 99.9%, and propyl carbinol quality purity is 99.9%.
Embodiment 2
In this example, evaporator pressure is 3MPa; Reactive distillation column adopts nickel-base catalyst, and conversion zone temperature is 100 DEG C, and pressure is 2MPa, and reflux ratio is 10, and hydrogen aldehyde mol ratio is 10:1; Butanols rectifying tower pressure is 0.7MPa (a), and reflux ratio is 1; Positive isobutanol separation column pressure is 1MPa, and reflux ratio is 20.Finally obtaining isopropylcarbinol quality purity is 99%, and propyl carbinol quality purity is 99.5%.
Embodiment 3
In this example, evaporator pressure is 1MPa (a); Reactive distillation column adopts copper-based catalysts, and conversion zone temperature is 120 DEG C, and pressure is 0.6MPa, and reflux ratio is 30, and hydrogen aldehyde mol ratio is 20:1; Butanols rectifying tower pressure is 1MPa, and reflux ratio is 30; Positive isobutanol separation column pressure is 0.5MPa, and reflux ratio is 50.Finally obtaining isopropylcarbinol quality purity is 99.8%, and propyl carbinol quality purity is 99.9%.
Claims (7)
1. butyraldehyde produces a reaction and rectification device for butanols, comprises vaporizer, reactive distillation column, butanols rectifying tower, positive isobutanol separation column, condenser, reboiler, compressor, pump and relevant feedstocks pipeline and the pipeline being connected above equipment; It is characterized in that reactive distillation column, butanols rectifying tower and positive isobutanol separation column tower top all arrange condenser, the end all arranges reboiler; Evaporator overhead gaseous phase outlet is connected to reactive distillation column; Reactive distillation column overhead condenser gaseous phase outlet is connected to compressor, and compressor outlet is connected to reactive distillation column hydrogen feed mouth, and condensator outlet liquid phase, as light component product extraction, is that cymogene alcohol product is connected to butanols rectifying tower opening for feed at the bottom of tower; Butanols rectifying tower ejects material and enters positive isobutanol separation column for mixed butyl alcohol, is heavy constituent by product at the bottom of tower; The discharging of positive isobutanol separation column tower top is isobutanol product, and discharging at the bottom of tower is propyl carbinol product.
2. adopt device according to claim 1 to produce the method for butyraldehyde hydrogenation butanols: it is characterized in that: (the butyraldehyde gas after evaporator vaporization enters the bottom of reactive distillation column conversion zone to raw material butyraldehyde together with raw hydrogen; Reactive distillation column top gaseous phase enters reactive distillation column overhead condenser, after condensation, gas phase is that the hydrogen of unreacted hydrogen after compressor pressurizes returns reactive distillation column charging, after condensation, liquid phase obtains liquid phase through reactive distillation column reflux-withdrawal pump, control by operating reflux ratio, a part is as phegma, another part is as the extraction of tower top light constituent, and at the bottom of tower, extraction cymogene alcohol is as the charging of butanols rectifying tower; The liquid phase of butanols rectifying tower top gaseous phase after condenser condenses obtains liquid phase through butanols rectifier column reflux extraction pump, control by operating reflux ratio, a part as phegma, another part be mixed butyl alcohol as positive isobutanol separation column charging, extraction heavy constituent by product at the bottom of tower; The liquid phase of positive isobutanol separation column top gaseous phase after condenser condenses obtains liquid phase through positive isobutanol separation column reflux-withdrawal pump, control by operating reflux ratio, a part as phegma, another part as isobutanol product extraction, extraction propyl carbinol product at the bottom of tower.
3. method as claimed in claim 2, is characterized in that described evaporator pressure is 0.01-3MPa.
4. method as claimed in claim 2, it is characterized in that described reactive distillation column adopts nickel and/or copper-based catalysts, conversion zone temperature is 100-250 DEG C, and pressure is 0.01-2MPa, and reflux ratio is 10-100, and hydrogen aldehyde mol ratio is 10:1-30:1.
5. method as claimed in claim 4, is characterized in that described conversion zone temperature is 110-130 DEG C.
6. method as claimed in claim 2, it is characterized in that described butanols rectifying tower pressure is 0.5-1MPa, reflux ratio is 1-100.
7. method as claimed in claim 2, it is characterized in that described positive isobutanol separation column pressure is 0.1-1MPa, reflux ratio is 20-100.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410713043.4A CN104557457A (en) | 2014-11-28 | 2014-11-28 | Reactive distillation method and reactive distillation device for producing butanol by hydrogenating butyraldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410713043.4A CN104557457A (en) | 2014-11-28 | 2014-11-28 | Reactive distillation method and reactive distillation device for producing butanol by hydrogenating butyraldehyde |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104557457A true CN104557457A (en) | 2015-04-29 |
Family
ID=53074642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410713043.4A Pending CN104557457A (en) | 2014-11-28 | 2014-11-28 | Reactive distillation method and reactive distillation device for producing butanol by hydrogenating butyraldehyde |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104557457A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104844405A (en) * | 2015-05-14 | 2015-08-19 | 天津大学 | Device and method for separating pseudocumene from pseudocumene-rich material of methanol synthetic oil |
| CN107324972A (en) * | 2017-08-29 | 2017-11-07 | 湖北工程学院 | A kind of chromatographically pure tert-butyl alcohol and preparation method thereof, production system |
| CN107382669A (en) * | 2017-08-29 | 2017-11-24 | 湖北工程学院 | Chromatographically pure n-butanol and preparation method thereof, production system |
| CN111018668A (en) * | 2019-12-25 | 2020-04-17 | 淄博诺奥化工股份有限公司 | Green method for preparing mixed butanol by catalytic distillation |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1250599A (en) * | 1981-08-20 | 1989-02-28 | Norman Harris | Catalytic hydrogenation of aldehydes |
| CN102000534A (en) * | 2010-10-02 | 2011-04-06 | 中国石油大学(华东) | Synthesis device of methyl acetate and technological method thereof |
| CN102267880A (en) * | 2010-06-01 | 2011-12-07 | 中国石油化工集团公司 | Apparatus for switchable production of by products of isobutanol and isobutyraldehyde |
| CN102408304A (en) * | 2010-09-21 | 2012-04-11 | 中国石油化工股份有限公司 | Method for preparing alcohols by selectively hydrogenating aldehydes |
| CN102795961A (en) * | 2012-08-07 | 2012-11-28 | 临海市联盛化学有限公司 | Device and method for synthesizing sec-butyl alcohol by continuous reaction-rectification |
-
2014
- 2014-11-28 CN CN201410713043.4A patent/CN104557457A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1250599A (en) * | 1981-08-20 | 1989-02-28 | Norman Harris | Catalytic hydrogenation of aldehydes |
| CN102267880A (en) * | 2010-06-01 | 2011-12-07 | 中国石油化工集团公司 | Apparatus for switchable production of by products of isobutanol and isobutyraldehyde |
| CN102408304A (en) * | 2010-09-21 | 2012-04-11 | 中国石油化工股份有限公司 | Method for preparing alcohols by selectively hydrogenating aldehydes |
| CN102000534A (en) * | 2010-10-02 | 2011-04-06 | 中国石油大学(华东) | Synthesis device of methyl acetate and technological method thereof |
| CN102795961A (en) * | 2012-08-07 | 2012-11-28 | 临海市联盛化学有限公司 | Device and method for synthesizing sec-butyl alcohol by continuous reaction-rectification |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104844405A (en) * | 2015-05-14 | 2015-08-19 | 天津大学 | Device and method for separating pseudocumene from pseudocumene-rich material of methanol synthetic oil |
| CN107324972A (en) * | 2017-08-29 | 2017-11-07 | 湖北工程学院 | A kind of chromatographically pure tert-butyl alcohol and preparation method thereof, production system |
| CN107382669A (en) * | 2017-08-29 | 2017-11-24 | 湖北工程学院 | Chromatographically pure n-butanol and preparation method thereof, production system |
| CN111018668A (en) * | 2019-12-25 | 2020-04-17 | 淄博诺奥化工股份有限公司 | Green method for preparing mixed butanol by catalytic distillation |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104447243B (en) | The reactive distillation method of low pressure oxo process butyraldehyde and device | |
| CN102093178B (en) | Method for continuously producing unsaturated aldehyde compound by using reaction and rectification | |
| CN105622337B (en) | Novel reactive distillation coupling process and device for separating liquid-phase product of ethylene glycol prepared from coal | |
| CN102690172A (en) | Method for producing isopropanol by acetone hydrogenation | |
| CN104557457A (en) | Reactive distillation method and reactive distillation device for producing butanol by hydrogenating butyraldehyde | |
| CN106349019B (en) | A method of producing cyclohexanol | |
| CN110668917A (en) | Synthesis device and synthesis method of 1, 3-butanediol | |
| CN104355975A (en) | Method for synthesizing methyl isobutyl ketone from acetone by two-step process | |
| CN104387236A (en) | Trigeneration continuous production method for propiolic alcohol, 1,4-butinodiol and urotropine | |
| CN105980338A (en) | Process for producing 1,3-butadiene from a feedstock comprising ethanol | |
| CN103936574B (en) | A kind of method being prepared high-purity methyl iso-butyl ketone (MIBK) by industrial by-product waste liquid acetone | |
| US9850190B2 (en) | Process for preparing dichloropropanol | |
| CN103951558A (en) | Device for producing methyl formate by gas phase methanol carbonylation, process and catalyst on-line evaluation method | |
| CN204342701U (en) | Butyraldehyde hydrogenation produces the reaction and rectification device of butanols | |
| CN103214347A (en) | Method for producing cyclohexanol through benzene | |
| CN109721469A (en) | A kind of preparation method of cyclopentanone | |
| CN103864587A (en) | Method for synthesizing 2-ethyl-2-hexenal | |
| CN204342703U (en) | The reaction and rectification device of low pressure oxo process butyraldehyde | |
| EP2495241A1 (en) | Endo-methylene hexahydrophthalic anhydride and production method thereof | |
| CN101560152B (en) | Method for synthesizing propionate | |
| CN113582967A (en) | Device and method for preparing trioxymethylene | |
| CN105330504B (en) | Reclaim the device of refined propylene | |
| CN109503347B (en) | Method for rectifying and purifying methoxy acetone | |
| CN114230453A (en) | Production method for synthesizing propionic acid by one-step hydrogenation | |
| CN105585468B (en) | A method of cyclopentanone is prepared by raw material of cyclopentene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20150429 |