CN102992984A - Methyl ethyl ketone preparation method - Google Patents
Methyl ethyl ketone preparation method Download PDFInfo
- Publication number
- CN102992984A CN102992984A CN201110268980XA CN201110268980A CN102992984A CN 102992984 A CN102992984 A CN 102992984A CN 201110268980X A CN201110268980X A CN 201110268980XA CN 201110268980 A CN201110268980 A CN 201110268980A CN 102992984 A CN102992984 A CN 102992984A
- Authority
- CN
- China
- Prior art keywords
- sec
- alcohol
- butyl
- carbon alcohol
- low
- 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
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a methyl ethyl ketone preparation method. The method comprises the following steps: 1, carrying out an ester exchange reaction of sec-butyl acetate and low carbon alcohol in a catalytic rectifying tower in the presence of an ester exchange catalyst, wherein the low carbon alcohol is C1-C3 alcohol; and 2, carrying out a dehydrogenation reaction of the tower bottoms obtained in step 1 or sec-butyl alcohol separated from the tower bottoms obtained in the step 1 in the presence of a dehydrogenation catalyst. The method which allows sec-butyl alcohol to be prepared through using the sec-butyl acetate and the low carbon alcohol has the advantages of high raw material conversion rate and high sec-butyl alcohol selectivity.
Description
Technical field
The present invention relates to a kind of preparation method of methylethylketone.
Background technology
Methylethylketone claims again 2-butanone, it is a kind of important low boiling point solvent, can form azeotrope with numerous solvents, synthetic rubber, fiber derivative, grease etc. are had very strong dissolving power, be widely used in the fields such as coating, tackiness agent, lubricating oil, dyestuff and printing-ink.Simultaneously, but the intermediate of preparation spices, antioxidant and some catalyzer such as its also production methyl ethyl ketone peroxide, methyl ethyl ketoxime.
The production method of methylethylketone has n-butene method, butane liquid phase oxidation, Isobuytel Benzene method, isobutylene oxidation method, divinyl catalytic hydrolysis method, mixed C4 hydrocarbon oxidation style, fermentation method etc. more than ten to plant.Industrial process is mainly n-butene method, butane liquid phase oxidation and Isobuytel Benzene method, and is wherein general with the production of n-butene method applicable industry again.Yet above-mentioned three kinds of industrial processes all adopt fossil resource as raw materials for production, and it is complicated to exist product to reclaim separation system, invests the problems such as high, that energy consumption is large, and operational condition is strict.Concrete, the shortcoming such as the n-butene one-step oxidation process needs expensive titanium material installation because its reaction process is used the chloride catalyzer of homogeneous phase, and corrodibility is strong, and the by product muriate is many, the sepn process complexity and gradually being eliminated.N-butene two-step oxidation method comprises n-butylene hydration sec-butyl alcohol processed and two reactions steps of sec-butyl alcohol dehydrogenizing preparing ethyl methyl ketone.The method of n-butylene hydration sec-butyl alcohol processed mainly is divided into the indirect hydration method take sulfuric acid as catalyzer, and two kinds of techniques of direct hydration method take ion exchange resin or heteropolyacid as catalyzer, yet these the two kinds methods that prepare sec-butyl alcohol all exist feed stock conversion low, the shortcomings such as energy consumption height.
Summary of the invention
The objective of the invention is the defects that exists in order to overcome the existing method for preparing methylethylketone, a kind of preparation method of new methylethylketone is provided.
The invention provides a kind of preparation method of methylethylketone, the method may further comprise the steps:
(1) in the presence of transesterification catalyst, sec-butyl acetate and low-carbon alcohol be added to carry out transesterification reaction in the catalytic rectifying tower, wherein, described low-carbon alcohol is the alcohol of C1-C3;
(2) in the presence of dehydrogenation catalyst, isolated sec-butyl alcohol in the tower bottoms that obtains in the step (1) or the tower bottoms that obtains is carried out dehydrogenation reaction from step (1).
In the preparation method of described methylethylketone of the present invention, the step that is prepared sec-butyl alcohol by sec-butyl acetate and low-carbon alcohol can obtain higher feed stock conversion and sec-butyl alcohol selectivity.
Method according to the present invention, in the step of preparation sec-butyl alcohol, technique is simple, and lower to the production unit requirement, raw material is easy to get, and energy consumption is low, thereby greatly reduces production cost; And, need not to use acetic acid to make raw material, reduced equipment corrosion and environmental pollution.
Embodiment
The preparation method of methylethylketone according to the present invention may further comprise the steps:
(1) in the presence of transesterification catalyst, sec-butyl acetate and low-carbon alcohol be added to carry out transesterification reaction in the catalytic rectifying tower, wherein, described low-carbon alcohol is the alcohol of C1-C3;
(2) in the presence of dehydrogenation catalyst, isolated sec-butyl alcohol in the tower bottoms that obtains in the step (1) or the tower bottoms that obtains is carried out dehydrogenation reaction from step (1).
Method according to the present invention, in step (1), in order further to improve transformation efficiency and the sec-butyl alcohol selectivity of sec-butyl acetate, the operating process of described transesterification reaction preferably includes: with the sec-butyl acetate in the catalytic rectifying tower, the mixture heating up of low-carbon alcohol and transesterification catalyst is to boiling, and under the condition of total reflux, react the azeotropic point that reaches described low-carbon alcohol and described acetic acid ester of low-carbon alcohol to tower top temperature, then be 2-5 in reflux ratio: the azeotrope with described low-carbon alcohol and acetic acid ester of low-carbon alcohol under 1 the condition steams from cat head, reach the boiling point of described low-carbon alcohol until tower top temperature after, tower bottoms is discharged.
Method according to the present invention, in step (1), the stage number of catalytic rectifying tower or theoretical plate number are preferably the 40-50 piece.
Method according to the present invention, in step (1), the mol ratio of sec-butyl acetate and described low-carbon alcohol can be 1: 2-10 is preferably 1: 3-7.
Method according to the present invention, in step (1), what described low-carbon alcohol can be in methyl alcohol, ethanol, propyl alcohol and the Virahol is at least a.
Method according to the present invention, in step (1), described transesterification catalyst can use with the catalytic amount of routine.Under the preferable case, with respect to the consumption of the sec-butyl acetate of 100 weight parts, the consumption of described transesterification catalyst can be the 0.1-10 weight part, is preferably the 0.2-5 weight part.
Method according to the present invention, in step (1), described transesterification catalyst can be the conventional various transesterification catalysts that use in this area, for example can be in sodium hydroxide, potassium hydroxide, yellow soda ash, salt of wormwood, cesium carbonate, tosic acid, zinc acetate, lead acetate, cadmium acetate, calcium oxide, zinc oxide, plumbous oxide, sodium methylate, tetrabutyl titanate, stannous octoate, sulfuric acid, phosphoric acid, polyphosphoric acid, acidic molecular sieve and the ion exchange resin at least a.Described acidic molecular sieve for example can be ZSM-5 molecular sieve, Y zeolite and H beta-molecular sieve.Described ion exchange resin can be acidic ion exchange resin or deacidite, and described acidic ion exchange resin for example can be styrene type cation exchange resin (such as commercially available D001 type, D201 type and D732 type Zeo-karb) or sulfonic group Zeo-karb (such as commercially available DWN type Zeo-karb); The anionite-exchange resin that described deacidite for example can obtain after the sodium hydroxide solution pre-treatment for quaternary ammonium group anionite-exchange resin, tertiary amine fundamental mode anionite-exchange resin or these anionite-exchange resin is such as 201 * 4 commercially available types, 201 * 4H type, D201 type and D301 type anionite-exchange resin.
Method according to the present invention, in step (2), described dehydrogenation reaction can be implemented according to the dehydrogenation reaction method of routine, and for example, described dehydrogenation reaction can be carried out in fixed-bed reactor.In this case, the condition of described dehydrogenation reaction can comprise: temperature of reaction is 200-400 ℃, is preferably 260-380 ℃; The mass space velocity of isolated sec-butyl alcohol is 0.5-5h in the tower bottoms that obtains in the described step (1) or the tower bottoms that obtains from step (1)
-1, be preferably 1-4h
-1
The present inventor's discovery, the tower bottoms that obtains in the step (1) can be through separating or directly carrying out dehydrogenation reaction without separating.Isolated sec-butyl alcohol carries out in the situation of dehydrogenation reaction in the tower bottoms that will obtain from step (1), the method of isolated sec-butyl alcohol can adopt conventional method to implement in the tower bottoms that obtains from step (1), for example can adopt the method for distillation to separate.
Method according to the present invention, in step (2), described dehydrogenation catalyst can be the dehydrogenation catalyst of various routines, for example can for ZSM-5 molecular sieve catalyzer, NaY molecular sieve catalyst and molecular sieve solid acid catalyst (such as ZSM-5 load SO
4 2-/ Fe
2O
3Molecular sieve solid acid catalyst) and the platina catalyzer.Yet in order to improve transformation efficiency that sec-butyl alcohol transforms and the selectivity of methylethylketone, described dehydrogenation catalyst most preferably is the platina catalyzer.
In the present invention, described platina catalyzer can prepare according to the method for routine, for example, the preparation method of described platina catalyzer can comprise: the aqueous solution of water-soluble mantoquita and water-soluble zinc salt is mixed with alkaline solution, and be 7-9 in the pH value, temperature is under 40-60 ℃ the condition aging 10-60 minute, the mixture that will obtain after then will wearing out filters, and the solid that filtration obtains carried out drying and roasting, thereby obtain the platina catalyzer.Described water-soluble mantoquita for example can be cupric nitrate.Described water-soluble zinc salt for example can be zinc nitrate.Described alkaline solution is preferably ammoniacal liquor, the consumption of described alkaline solution so that after adding alkaline solution the pH value of mixing solutions in above-mentioned scope.The condition of described roasting can comprise: maturing temperature is 300-400 ℃, and roasting time is 2-8 hour, and the mass ratio of described water-soluble mantoquita and water-soluble zinc salt is 1: 0.2-5.
The invention will be further described by the following examples.
In following examples, the transformation efficiency of the transformation efficiency of sec-butyl acetate, the selectivity of sec-butyl alcohol, sec-butyl alcohol and the selectivity of methylethylketone calculate according to following calculating formula respectively.
The charging capacity of the transformation efficiency of sec-butyl acetate=(residual volume of sec-butyl acetate in the charging capacity-reaction product of sec-butyl acetate)/sec-butyl acetate * 100%
The mole number of the sec-butyl acetate of the mole number of the sec-butyl alcohol of the selectivity of sec-butyl alcohol=generation/be converted * 100%
The charging capacity of the transformation efficiency of sec-butyl alcohol=(residual volume of sec-butyl alcohol in the charging capacity-reaction product of sec-butyl alcohol)/sec-butyl alcohol * 100%
The mole number of the sec-butyl alcohol of the mole number of the methylethylketone of the selectivity of methylethylketone=generation/be converted * 100%
Embodiment 1
The present embodiment is used for illustrating the preparation method of described methylethylketone of the present invention.
(1) preparation of sec-butyl alcohol
Sec-butyl acetate and ethanol are added in the catalytic rectifying tower (stage number is as 50) as 1: 4 take mol ratio, add-on with respect to the sec-butyl acetate of 100 weight parts, to the CaO that wherein adds 2 weight parts as catalyzer, under normal pressure, under heating, make the material in the catalytic rectifying tower carry out total reflux, begin extraction after tower top temperature reaches 72 ℃ (azeotropic points of ethanol and ethyl acetate), the control reflux ratio is 3: 1, steams from cat head with the azeotrope with ethanol and ethyl acetate; After tower top temperature rises to 78 ℃ (boiling points of ethanol), tower bottoms is carried out fractionation by distillation, collect sec-butyl alcohol.
Learn by calculating, the transformation efficiency of sec-butyl acetate is 99.8%, and the selectivity of sec-butyl alcohol is 100%.
(2) preparation of dehydrogenation catalyst
The cupric nitrate of 52.3g and the zinc nitrate of 57.6g are dissolved in the 500ml deionized water, in the solution that obtains, drip ammoniacal liquor (concentration is 30 % by weight), be adjusted to 8 with the pH value with mixing solutions, under 40 ℃, mix afterwards, and under this temperature, wore out 20 minutes.Then, the mixture that obtains after aging is filtered, and the solid that obtains is washed and drying, then 350 ℃ of lower roastings 4 hours, obtain the platina catalyzer.Then, get the described platina catalyzer of 100 weight parts and the Graphite Powder 99 of 1 weight part, they are mixed, and carry out compression molding, then grind to form 10-20 purpose catalyzer.
(3) preparation of methylethylketone
Be that 8 millimeters, length are that amount of fill is 4g in 650 millimeters the fixed-bed reactor with the catalyst filling of preparation in the step (2) at internal diameter.Afterwards, the beds in the reaction unit is warming up to 300 ℃, and with the mixed gas (volume ratio is 1: 1) of hydrogen and nitrogen with 1000h
-1Volume space velocity inject reaction unit, with described beds activation 1 hour.Then, the sec-butyl alcohol of preparation in the step (1) is injected described reaction unit, the temperature in the described reaction unit is controlled to be 300 ℃, and to make the mass space velocity of sec-butyl alcohol be 2h
-1
Learn by calculating, the transformation efficiency of sec-butyl alcohol is 95%, and the selectivity of methylethylketone is 98%.
Embodiment 2
The present embodiment is used for illustrating the preparation method of described methylethylketone of the present invention.
Method according to embodiment 1 prepares methylethylketone, and difference is in step (2), to use ZSM-5 molecular sieve catalyzer (silica alumina ratio is 38) to replace the platina catalyzer as dehydrogenation catalyst.
Learn by calculating, the transformation efficiency of sec-butyl alcohol is 75%, and the selectivity of methylethylketone is 78%.
Embodiment 3
The present embodiment is used for illustrating the preparation method of described methylethylketone of the present invention.
Method according to embodiment 1 prepares methylethylketone, and difference is in step (2), to use ZSM-5 load SO
4 2-/ Fe
2O
3Molecular sieve solid acid catalyst (method according to embodiment among the CN101580462A 1 makes) replaces the platina catalyzer as dehydrogenation catalyst.
Learn by calculating, the transformation efficiency of sec-butyl alcohol is 78%, and the selectivity of methylethylketone is 83%.
Embodiment 4
The present embodiment is used for illustrating the preparation method of described methylethylketone of the present invention.
(1) preparation of sec-butyl alcohol
Sec-butyl acetate and propyl alcohol are added in the catalytic rectifying tower (stage number is as 50) as 1: 3 take mol ratio, with respect to the described sec-butyl acetate of 100 weight parts and the gross weight of propyl alcohol, to the D301 anionite-exchange resin that wherein adds 4 weight parts (available from Langfang prosperous chemical building material of prosperous Sheng company limited) as catalyzer, under normal pressure, under heating, make the material in the catalytic rectifying tower carry out total reflux, after reaching 95 ℃ (azeotropic points of propyl alcohol and propyl acetate), tower top temperature begins extraction, the control reflux ratio is 2: 1, steams from cat head with the azeotrope with propyl alcohol and propyl acetate; After tower top temperature rises to 97 ℃ (boiling points of propyl alcohol), tower bottoms is carried out fractionation by distillation, collect sec-butyl alcohol.
Learn by calculating, the selectivity of sec-butyl alcohol is 100%, and the transformation efficiency of sec-butyl acetate is 99.5%.
(2) preparation of dehydrogenation catalyst
Method according to step (2) among the embodiment 1 prepares dehydrogenation catalyst.
(3) preparation of methylethylketone
Be that 8 millimeters, length are that amount of fill is 4g in 650 millimeters the fixed-bed reactor with the catalyst filling of preparation in the step (2) at internal diameter.Afterwards, the beds in the reaction unit is warming up to 300 ℃, and with the mixed gas (volume ratio is 1: 1) of hydrogen and nitrogen with 1000h
-1Volume space velocity inject reaction unit, with described beds activation 1 hour.Then, the sec-butyl alcohol of preparation in the step (1) is injected described reaction unit, the temperature in the described reaction unit is controlled to be 200 ℃, and to make the mass space velocity of sec-butyl alcohol be 1h
-1
Learn by calculating, the transformation efficiency of sec-butyl alcohol is 90%, and the selectivity of methylethylketone is 95%.
Embodiment 5
The present embodiment is used for illustrating the preparation method of described methylethylketone of the present invention.
(1) preparation of sec-butyl alcohol
Sec-butyl acetate and methyl alcohol are added in the catalytic rectifying tower (stage number is as 40) as 1: 5 take mol ratio, with respect to the described sec-butyl acetate of 100 weight parts and the gross weight of methyl alcohol, to wherein adding 2 weight part sodium methylates as catalyzer, under normal pressure, under heating, make the material in the catalytic rectifying tower carry out total reflux, after reaching 54 ℃ (azeotropic points of methyl alcohol and methyl acetate), tower top temperature begins extraction, the control reflux ratio is 2: 1, steams from cat head with the azeotrope with methyl alcohol and methyl acetate; After tower top temperature rises to 64 ℃ (boiling points of methyl alcohol), tower bottoms is carried out fractionation by distillation, collect sec-butyl alcohol.
Learn by calculating, the selectivity of sec-butyl alcohol is 100%, and the transformation efficiency of sec-butyl acetate is 99.2%.
(2) preparation of dehydrogenation catalyst
Method according to step (2) among the embodiment 1 prepares dehydrogenation catalyst.
(3) preparation of methylethylketone
Be that 8 millimeters, length are that amount of fill is 4g in 650 millimeters the fixed-bed reactor with the catalyst filling of preparation in the step (2) at internal diameter.Afterwards, the beds in the reaction unit is warming up to 300 ℃, and with the mixed gas (volume ratio is 1: 1) of hydrogen and nitrogen with 1000h
-1Volume space velocity inject reaction unit, with described beds activation 1 hour.Then, the sec-butyl alcohol of preparation in the step (1) is injected described reaction unit, the temperature in the described reaction unit is controlled to be 400 ℃, and to make the mass space velocity of sec-butyl alcohol be 4h
-1
Learn by calculating, the transformation efficiency of sec-butyl alcohol is 93%, and the selectivity of methylethylketone is 96%.
Embodiment 6
The present embodiment is used for illustrating the preparation method of described methylethylketone of the present invention.
(1) preparation of sec-butyl alcohol
Sec-butyl acetate and Virahol are added in the catalytic rectifying tower (stage number is as 40) as 1: 7 take mol ratio, with respect to the described sec-butyl acetate of 100 weight parts and the gross weight of Virahol, to wherein adding 2 weight part ZSM-5 molecular sieves (available from Nanjing Ji Cang nanosecond science and technology company limited) as catalyzer, under normal pressure, under heating, make the material in the catalytic rectifying tower carry out total reflux, after reaching 80 ℃ (azeotropic points of Virahol and isopropyl acetate), tower top temperature begins extraction, the control reflux ratio is 3: 1, steams from cat head with the azeotrope with Virahol and isopropyl acetate; After tower top temperature rises to 82.5 ℃ (boiling points of Virahol), tower bottoms is carried out fractionation by distillation, collect sec-butyl alcohol.
Learn by calculating, the selectivity of sec-butyl alcohol is 100%, and the transformation efficiency of sec-butyl acetate is 99.3%.
(2) preparation of dehydrogenation catalyst
Method according to step (2) among the embodiment 1 prepares dehydrogenation catalyst.
(3) preparation of methylethylketone
Be that 8 millimeters, length are that amount of fill is 4g in 650 millimeters the fixed-bed reactor with the catalyst filling of preparation in the step (2) at internal diameter.Afterwards, the beds in the reaction unit is warming up to 300 ℃, and with the mixed gas (volume ratio is 1: 1) of hydrogen and nitrogen with 1000h
-1Volume space velocity inject reaction unit, with described beds activation 1 hour.Then, the sec-butyl alcohol of preparation in the step (1) is injected described reaction unit, the temperature in the described reaction unit is controlled to be 350 ℃, and to make the mass space velocity of sec-butyl alcohol be 3h
-1
Learn by calculating, the transformation efficiency of sec-butyl alcohol is 94%, and the selectivity of methylethylketone is 97%.
Can find out that by the result with above-described embodiment method according to the present invention can obtain higher sec-butyl acetate transformation efficiency and sec-butyl alcohol selectivity in the process of preparation sec-butyl alcohol; In the process of preparation methylethylketone, can obtain higher sec-butyl alcohol transformation efficiency and methylethylketone selectivity.
Claims (10)
1. the preparation method of a methylethylketone, the method may further comprise the steps:
(1) in the presence of transesterification catalyst, sec-butyl acetate and low-carbon alcohol be added to carry out transesterification reaction in the catalytic rectifying tower, wherein, described low-carbon alcohol is the alcohol of C1-C3;
(2) in the presence of dehydrogenation catalyst, isolated sec-butyl alcohol in the tower bottoms that obtains in the step (1) or the tower bottoms that obtains is carried out dehydrogenation reaction from step (1).
2. method according to claim 1, wherein, in step (1), the operating process of described transesterification reaction comprises: with the extremely boiling of mixture heating up of the sec-butyl acetate in the catalytic rectifying tower, low-carbon alcohol and transesterification catalyst, and under the condition of total reflux, react the azeotropic point that reaches described low-carbon alcohol and described acetic acid ester of low-carbon alcohol to tower top temperature, then be 2-5 in reflux ratio: the azeotrope with described low-carbon alcohol and acetic acid ester of low-carbon alcohol under 1 the condition steams from cat head, reach the boiling point of described low-carbon alcohol until tower top temperature after, tower bottoms is discharged.
3. method according to claim 1 and 2, wherein, in step (1), the mol ratio of sec-butyl acetate and described low-carbon alcohol is 1: 2-10.
4. method according to claim 1 and 2, wherein, in step (1), described low-carbon alcohol is at least a in methyl alcohol, ethanol, propyl alcohol and the Virahol.
5. method according to claim 1 and 2, wherein, in step (1), with respect to the consumption of the sec-butyl acetate of 100 weight parts, the consumption of described transesterification catalyst is the 0.1-10 weight part.
6. method according to claim 1 and 2, wherein, in step (1), described transesterification catalyst is at least a in sodium hydroxide, potassium hydroxide, yellow soda ash, salt of wormwood, cesium carbonate, tosic acid, zinc acetate, lead acetate, cadmium acetate, calcium oxide, zinc oxide, plumbous oxide, sodium methylate, tetrabutyl titanate, stannous octoate, sulfuric acid, phosphoric acid, polyphosphoric acid, acidic molecular sieve and the ion exchange resin.
7. method according to claim 1, wherein, in step (2), described dehydrogenation reaction is carried out in fixed-bed reactor.
8. method according to claim 7, wherein, the condition of described dehydrogenation reaction comprises: temperature of reaction is 200-400 ℃, and the mass space velocity of isolated sec-butyl alcohol is 0.5-5h in the tower bottoms that obtains in the described step (1) or the tower bottoms that obtains from step (1)
-1
9. method according to claim 1, wherein, the condition of described dehydrogenation reaction comprises: temperature of reaction is 260-380 ℃, and the mass space velocity of isolated sec-butyl alcohol is 1-4h in the tower bottoms that obtains in the described step (1) or the tower bottoms that obtains from step (1)
-1
10. according to claim 1 or 9 described methods, wherein, in step (2), described dehydrogenation catalyst is the platina catalyzer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110268980XA CN102992984A (en) | 2011-09-13 | 2011-09-13 | Methyl ethyl ketone preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110268980XA CN102992984A (en) | 2011-09-13 | 2011-09-13 | Methyl ethyl ketone preparation method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102992984A true CN102992984A (en) | 2013-03-27 |
Family
ID=47922169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110268980XA Pending CN102992984A (en) | 2011-09-13 | 2011-09-13 | Methyl ethyl ketone preparation method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102992984A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103739469A (en) * | 2013-12-24 | 2014-04-23 | 山东滨州裕华化工厂有限公司 | Process for preparing MEK (Methyl Ethyl Ketone) by utilizing C4 fraction in etherified liquefied petroleum gas |
| CN104370722A (en) * | 2014-12-11 | 2015-02-25 | 湖南瑞源石化股份有限公司 | Butanone preparation and refining method |
| CN104478676A (en) * | 2014-12-11 | 2015-04-01 | 湖南瑞源石化股份有限公司 | Butanone preparing and refining system |
| CN105712819A (en) * | 2014-12-17 | 2016-06-29 | Sk新技术株式会社 | Method for recycling 1,3-butadiene and methyl ethyl ketone from 2,3-butanediol dehydration products |
| CN111517936A (en) * | 2019-02-02 | 2020-08-11 | 中国科学院大连化学物理研究所 | Method for preparing ketone organic matter |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU734182A1 (en) * | 1977-07-07 | 1980-05-15 | Ярославский политехнический институт | Method of producing secondary butanol |
| CN1289753A (en) * | 1999-09-29 | 2001-04-04 | 中国石油化工集团公司 | Process for preparing ketone by dehydrogenating para-alcohol |
| CN1289752A (en) * | 1999-09-29 | 2001-04-04 | 中国石油化工集团公司 | Process for preparing aldehyde and ketone by dehydrogenating alcohol |
| CN1415591A (en) * | 2001-10-30 | 2003-05-07 | 中国石油化工股份有限公司 | Technical method of dehydrogenating alcohols |
-
2011
- 2011-09-13 CN CN201110268980XA patent/CN102992984A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU734182A1 (en) * | 1977-07-07 | 1980-05-15 | Ярославский политехнический институт | Method of producing secondary butanol |
| CN1289753A (en) * | 1999-09-29 | 2001-04-04 | 中国石油化工集团公司 | Process for preparing ketone by dehydrogenating para-alcohol |
| CN1289752A (en) * | 1999-09-29 | 2001-04-04 | 中国石油化工集团公司 | Process for preparing aldehyde and ketone by dehydrogenating alcohol |
| CN1415591A (en) * | 2001-10-30 | 2003-05-07 | 中国石油化工股份有限公司 | Technical method of dehydrogenating alcohols |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103739469A (en) * | 2013-12-24 | 2014-04-23 | 山东滨州裕华化工厂有限公司 | Process for preparing MEK (Methyl Ethyl Ketone) by utilizing C4 fraction in etherified liquefied petroleum gas |
| CN104370722A (en) * | 2014-12-11 | 2015-02-25 | 湖南瑞源石化股份有限公司 | Butanone preparation and refining method |
| CN104478676A (en) * | 2014-12-11 | 2015-04-01 | 湖南瑞源石化股份有限公司 | Butanone preparing and refining system |
| CN104370722B (en) * | 2014-12-11 | 2015-08-26 | 湖南瑞源石化股份有限公司 | Preparation and the refining method of butanone |
| CN104478676B (en) * | 2014-12-11 | 2016-03-16 | 湖南瑞源石化股份有限公司 | Preparation and the refining system of butanone |
| CN105712819A (en) * | 2014-12-17 | 2016-06-29 | Sk新技术株式会社 | Method for recycling 1,3-butadiene and methyl ethyl ketone from 2,3-butanediol dehydration products |
| CN105712819B (en) * | 2014-12-17 | 2020-08-07 | Sk新技术株式会社 | Method for recovering 1, 3-butadiene and methyl ethyl ketone from 2,3-butanediol dehydration product |
| CN111517936A (en) * | 2019-02-02 | 2020-08-11 | 中国科学院大连化学物理研究所 | Method for preparing ketone organic matter |
| CN111517936B (en) * | 2019-02-02 | 2021-09-10 | 中国科学院大连化学物理研究所 | Method for preparing ketone organic matter |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102153465B (en) | Method for preparing low acid-value fatty acid methyl ester | |
| TWI612031B (en) | Method and device for co-production of cyclohexanol and alkanol | |
| CN104232140A (en) | Method for synthesizing high-density aviation fuel by using cyclopentanone as raw material | |
| CN104045503B (en) | One utilizes Furnan products and cyclic ketones to prepare C 10-C 18the method of oblong link alkane | |
| CN102992984A (en) | Methyl ethyl ketone preparation method | |
| CN112023982B (en) | Method for preparing zirconium-loaded PAN (Polyacrylonitrile) composite material through electrostatic spinning and application | |
| CN102372596A (en) | Method for producing glycol product by separating synthetic gas | |
| CN103288626B (en) | Method for co-producing adipic acid and nitrocyclohexane | |
| CN102875334B (en) | Synthetic method for preparing cyclopentanol and cyclopentanone by furfural | |
| CN102206142A (en) | Method for preparing 3-methoxyl-3-methyl-1-butanol | |
| CN102992956A (en) | Preparation method of 2-butyl alcohol | |
| CN108043456B (en) | Polyacid ionic liquid catalyst, preparation method and method for preparing cyclohexanol by catalyzing hydrolysis of cyclohexyl acetate with polyacid ionic liquid catalyst | |
| CN103420786B (en) | The method of coproducing methyl isobutyl ketone and methyl isobutyl carbinol | |
| CN102093183A (en) | Method for preparing 2-ethyl-2-hexenoicaldehyde by condensing n-butanal under catalysis of solid base catalyst | |
| CN102372614B (en) | Production method of polyoxymethylene dimethylether | |
| CN101580486A (en) | Method for synthesizing N-methylpyrrolidone catalyzed by particle type solid superacid | |
| CN111138278B (en) | Preparation method of butanediol caprylate | |
| CN103724210B (en) | The production method of N-ethyl-n-butylamine | |
| CN103012276B (en) | Long-chain alkyl sulfoacid functionalized heteropolyacid salt, preparation method and application of long-chain alkyl sulfoacid functionalized heteropolyacid salt | |
| CN101439295B (en) | Catalyst for preparing ethylene by ethanol dehydration and preparation method and application thereof | |
| CN103709010A (en) | Method for synthesizing cyclohexanol by reacting cyclohexene, carboxylic acid and water | |
| CN107952479B (en) | Functionalized polyacid ionic liquid catalyst, preparation method and method for catalyzing direct esterification of cyclohexene by functionalized polyacid ionic liquid catalyst | |
| CN100567237C (en) | The method of acetal or ketal preparing alkenyl ether by gas phase decomposing | |
| CN102050706A (en) | Method for serially producing dimethyl ether by dehydrating solid acid catalyzing methanol | |
| CN109384642A (en) | A kind of preparation method of sec-butyl alcohol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20130327 |