CN105130770A - Method for combined production of ethyl methyl ketone and ethanol - Google Patents

Method for combined production of ethyl methyl ketone and ethanol Download PDF

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Publication number
CN105130770A
CN105130770A CN201510455581.2A CN201510455581A CN105130770A CN 105130770 A CN105130770 A CN 105130770A CN 201510455581 A CN201510455581 A CN 201510455581A CN 105130770 A CN105130770 A CN 105130770A
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China
Prior art keywords
methylethylketone
copper
sec
butyl acetate
ethanol
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李永刚
付朋
向浩
王敏芝
孙思杰
宁春利
张春雷
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Shanghai Huayi Group Corp
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Shanghai Huayi Group Corp
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    • 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
    • C07C29/147—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 carboxylic acids or derivatives thereof
    • C07C29/149—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 carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to a method for combined production of ethyl methyl ketone and ethanol. The method solves the problem that the prior art cannot recycle hydrogen. The method comprises 1, feeding a sec-butyl acetate raw material and a hydrogen raw material into a hydrogenation unit, feeding a material flow from a hydrogenation unit outlet into a first separation unit, carrying out separation to obtain an unreacted sec-butyl acetate flow, a sec-butyl alcohol flow, an ethanol flow and a by-product flow, and returning the unreacted sec-butyl acetate flow to the hydrogenation unit, 2, feeding the sec-butyl alcohol flow into a dehydrogenation reaction unit to obtain an ethyl methyl ketone flow and a hydrogen flow, feeding the ethyl methyl ketone flow and unreacted sec-butyl alcohol in the dehydrogenation reaction unit into a second separation unit, carrying out separation to obtain an ethyl methyl ketone flow and an unreacted sec-butyl alcohol flow, and returning the hydrogen flow into the hydrogenation unit. The method successfully solves the above problem and can be used for ethyl methyl ketone and ethanol production.

Description

The method of coproduction methylethylketone and ethanol
Technical field
The present invention relates to a kind of method of coproduction methylethylketone and ethanol.
Background technology
Methylethylketone is a kind of important low boiling point solvent, has excellent solubility property.Can dissolve each other with hydrocarbons kind solvent, and its solid content and viscosity are not had an impact, have been widely used at industrial sectors such as coating adhesive tape sizing agent and synthetic leather ink tapes.In addition, methylethylketone is also a kind of important fine chemical material, can be used for producing methylethyl ketone peroxide, and first class allyl ketone, methyl amyl ketoxime, dimethyl diketone, can be widely used in spices, catalyzer, coating antioxidant agent and stopping agent etc.The production method of methylethylketone mainly contains n-butene method, divinyl catalyzed hydrolytic methods, butylene liquid phase oxidation, Isobuytel Benzene method, isobutyric aldehyde isomerate process and fermentation method etc. more than 10 plants method, but industrialized production method has only had n-butene method, normal butane liquid phase oxidation and Isobuytel Benzene method.Wherein n-butene two-step approach produces the most general method of methylethylketone both at home and abroad at present.Butane liquid phase oxidation is the byproduct for the production of acetic acid, and along with the development of low-pressure methanol carbonylation legal system acetic acid, the method produces methylethylketone dim future.N-butene method produces methylethylketone single stage method and two-step approach two kinds of methods, and single stage method is that normal butane generates methylethylketone with oxygen direct reaction in catalyst solution, but because reaction preference is low, does not have industrialization at present.N-butene two-step approach first n-butylene hydration is generated sec-butyl alcohol, and then dehydrogenation generates methylethylketone.This method is the main method of producing at present methylethylketone in the world, its output account for Gross World Product 80%.The methylethylketone of China is produced and is also mainly taked the method.
The technology developed at present has utilize biomass to obtain through biological fermentation process 2,3 Butanediol routes, CN102962092A discloses to adopt in effective catalyst gas phase and realizes dehydration, under 220 DEG C of conditions, butyleneglycol transformation efficiency can reach 100%, methylethylketone selectivity 81.3%, liquid hourly space velocity 2.37g/ (gh).CN102826980A discloses a continuous print fixed bed liquid-phase dehydration technology, and butyleneglycol transformation efficiency is greater than 97%, and methylethylketone yield is greater than 95%.CN101580462A and CN101293817A obtains similar results in different catalysts.CN102351672A discloses and utilizes organic sulfonic acid to realize liquid-phase dehydration in extractive distillation column, and butyleneglycol transformation efficiency is greater than 95%, and methylethylketone yield is greater than 91%.
Ethanol is commonly called as alcohol, and be a kind of important industrial chemicals, it is widely used in food, chemical industry, military project, medicine and other fields.Ethanol or a kind of green liquid fuel, can substitute harmful oxygenation agent and detonation suppressor as gasoline dope simultaneously completely.Meanwhile, along with process of industrialization, Global Greenhouse Effect is aggravated, and environmental pollution is on the rise, and Global Greenhouse Effect is aggravated, and this has promoted the exploitation dynamics of people to Green Product greatly, and ethanol is more and more concerned in recent years as fuel and gasoline dope.The current ethanol of global 98% adopts fermentative Production, and the method economic competitiveness is lower.The operational path of the synthesizing alcohol of development of new is significant.
Petrochemical complex and in recent years domestic flourish Coal Chemical Industry produce abundant hybrid C 4 resource.The acetic acid synthesized device of low-pressure methanol carbonylation method builds up in a large number, makes acetic acid production capacity greatly superfluous, the continued downturn of acetic acid price.Utilize hybrid C 4 and acetic acid addition esterification to prepare 2-butyl acetate technology and realize industrialization.Along with 2-butyl acetate is in production-scale rapid expansion, it becomes a kind of large Chemicals gradually, the exploitation of its derived product has been caused to the extensive concern of academia and industry member.
Utilize 2-butyl acetate for raw material, produce the operational path that methylethylketone is a very attractive.CN102992984A discloses after a kind of 2-butyl acetate and low-carbon alcohol carry out transesterification reaction, more further prepared by sec-butyl alcohol dehydrogenizing the method for methylethylketone.But sec-butyl is converted into methylethylketone by this method on the one hand, but senior acetic ester higher for added value is converted into the lower acetic ester of added value on the other hand.Macroeconomic sexual needs improve further.Can by-product hydrogen when methylethylketone is produced in sec-butyl alcohol dehydration, the main emptying of hydrogen or make fuel in the method, not only wastes hydrogen resources, and there is potential safety hazard.
Summary of the invention
The invention provides a kind of method of new coproduction methylethylketone and ethanol, technical problem to be solved is the economic benefit that improve existing methylethylketone production technology by the mode of coproduction, by the coupling of hydrogenation process and dehydration processes, realizes the recycle of hydrogen.The method is used in the production of methylethylketone and ethanol, having high financial profit, the advantage that hydrogen comprehensive utilization ratio improves.
For solving the problem, the technical solution used in the present invention is as follows: a kind of method of coproduction methylethylketone and ethanol, comprise the following steps: (1) 2-butyl acetate raw material and hydrogen feed enter hydrogenation unit, hydrogenation unit outlet streams enters the first separating unit and is separated, obtain unreacted 2-butyl acetate logistics, sec-butyl alcohol logistics, ethanol stream and byproduct streams respectively, described unreacted 2-butyl acetate logistics returns hydrogenation unit; (2) described sec-butyl alcohol logistics enters dehydrogenation reaction unit, generate methylethylketone logistics and hydrogen gas stream, described methylethylketone logistics enters the second separating unit with the unreacted sec-butyl alcohol of dehydrogenation reaction unit and is separated, obtain methylethylketone logistics and unreacted sec-butyl alcohol logistics, described hydrogen gas stream returns hydrogenation unit, and described unreacted sec-butyl alcohol logistics returns dehydrogenation reaction unit.
In technique scheme, preferably, described 2-butyl acetate raw material comprises the 2-butyl acetate that n-butylene hydration method route and hybrid C 4 and acetic acid addition esterification process route are produced; The mol ratio of the 2-butyl acetate raw material and hydrogen feed that enter hydrogenation unit is 5-80.
In technique scheme, preferably, the temperature of described hydrogenation unit is 150-350 DEG C, and reaction pressure is 0.3-10.0MPaG, and the 2-butyl acetate raw materials quality liquid hourly space velocity of hydrogenation unit is 0.1-5.0h -1; The catalyzer that hydrogenation unit uses comprises the oxide compound of copper or copper.
In technique scheme, more preferably, the catalyzer that hydrogenation unit uses comprises the oxide compound of copper or copper, second component and three components, and second component is ZnO, ZrO 2, TiO 2, Al 2o 3, SiO 2in at least one, three components is La 2o 3, CeO 2, Fe 2o 3, CaO, MgO, MnO, B 2o 3, K 2o, BaO, Li 2at least one in O, in catalyzer, the oxide mass content of copper or copper is 19-75%, and second component mass content is 20-80%, and three components mass content is 1-40%.
In technique scheme, preferably, the temperature of dehydrogenation reaction unit is 180-320 DEG C, and pressure is 0.03-1.0MPaG, and the quality liquid hourly space velocity of sec-butyl alcohol is 1.0-10.0h -1, dehydrogenation catalyst is copper-based catalysts.
In technique scheme, more preferably, the catalyzer of dehydrogenation reaction unit use comprises the oxide compound of copper or copper, second component and three components, and second component is ZnO, Al 2o 3, SiO 2in at least one, three components is La 2o 3, Fe 2o 3, CaO, MgO, MnO, B 2o 3, K 2at least one in O, BaO, in catalyzer, the oxide mass content of copper or copper is 40-70%, and second component mass content is 29-59%, and three components mass content is 0.5-30%.
In technique scheme, preferably, described byproduct streams comprises acetaldehyde, vinyl acetic monomer, C8 alkene and diisobutyl ether.
This patent provides a kind of method of coproduction methylethylketone and ethanol.2-butyl acetate generates sec-butyl alcohol and ethanol at copper-based catalysts hydrogenation, and after being separated, sec-butyl alcohol dehydrogenation on copper-based catalysts generates methylethylketone.In the method, hydrogenation reaction and dehydrogenation reaction are coupled, and achieve the comprehensive utilization of hydrogen.In the method, sec-butyl acetate transformation efficiency is greater than 99%, and methylethylketone yield is higher than 95%, and ethanol yield is higher than 95%.The coproduction methylethylketone that present method provides and the method for ethanol can significantly reduce costs, and obtain higher Production Gain, achieve good technique effect.
Below by embodiment, the invention will be further elaborated, but be not limited only to the present embodiment.
Embodiment
The invention provides a kind of method of coproduction methylethylketone and ethanol.Reaction system by 2-butyl acetate, hydrogen and hydrogenation catalyst and dehydrogenation catalyst composition.The generation sec-butyl alcohol of 2-butyl acetate high-activity high-selectivity on hydrogenation catalyst and ethanol, after being separated, sec-butyl alcohol dehydrogenation on dehydrogenation catalyst generates methylethylketone.In the present invention, hydrogenation catalyst and dehydrogenation catalyst use conventional hydrogen reduction method to activate.Activation temperature 200-350 DEG C, 2-30 hour.
[embodiment 1]
Coprecipitation method is adopted to prepare CuO-ZnO-ZrO 2hydrogenation commercial catalysts (cylindrical, Φ 5*5mm), wherein CuO content 65wt%, ZnO content 25wt%, ZrO 2content 10wt%.Coprecipitation method is adopted to prepare CuO-ZnO-MgO dehydrogenation commercial catalysts (cylindrical, Φ 5*5mm), wherein CuO content 60wt%, ZnO content 25wt%, content of MgO 15wt%.Hydrogenator and dehydrogenation reactor are 316 stainless steel tubes, internal diameter 38mm, hydrogenation catalyst loadings 9Kg, dehydrogenation reactor catalyst loadings 0.4Kg.2-butyl acetate enters hydrogenator, and hydrogenation reaction product utilizes rectifying tower to be separated; After being separated, sec-butyl alcohol enters dehydrogenation reactor, and the hydrogen that dehydrogenation reactor produces, after supercharger supercharging, mixes with hydrogenating materials hydrogen, jointly enters hydrogenator.
Hydrogenation conditions: 2-butyl acetate raw material and hydrogen mol ratio are 15; 2-butyl acetate raw materials quality liquid hourly space velocity is 0.5h -1; Temperature of reaction is 190 DEG C; Reaction pressure is 4.0MPaG.
Dehydrogenation reaction conditions: sec-butyl alcohol quality liquid hourly space velocity is 7.0h -1; Temperature of reaction is 240 DEG C; Reaction pressure is 0.05MPaG.
Test steady running, after 72 hours, carries out material balance, 2-butyl acetate transformation efficiency 97.2%, methylethylketone yield 96.2%, ethanol yield 97.3%.
[embodiment 2]
According to the condition described in embodiment 1 and step, adopting coprecipitation method to prepare hydrogenation catalyst is CuO-CaO-SiO 2(cylindrical, Φ 5*5mm), wherein CuO content 60wt%, CaO content 10wt%, SiO 2content 30wt%.Coprecipitation method is adopted to prepare CuO-K 2o-SiO 2dehydrogenation commercial catalysts (cylindrical, Φ 5*5mm), wherein CuO content 55wt%, SiO 2content 40wt%, K 2o content 5wt%.Hydrogenation catalyst loadings 4Kg, dehydrogenation reactor catalyst loadings 1.8Kg.
Hydrogenation conditions: 2-butyl acetate raw material and hydrogen mol ratio are 20; 2-butyl acetate raw materials quality liquid hourly space velocity is 2.0h -1; Temperature of reaction is 220 DEG C; Reaction pressure is 2.0MPaG.
Dehydrogenation reaction conditions: sec-butyl alcohol quality liquid hourly space velocity is 3.0h -1; Temperature of reaction is 200 DEG C; Reaction pressure is 0.8MPaG.
Test steady running, after 72 hours, carries out material balance, 2-butyl acetate transformation efficiency 98.7%, methylethylketone yield 95.6%, ethanol yield 97.1%.
[embodiment 3]
According to the condition described in embodiment 1 and step, adopting coprecipitation method to prepare hydrogenation catalyst is CuO-ZnO-Al 2o 3-MnO 2(cylindrical, Φ 5*5mm), wherein CuO content 60wt%, ZnO content 15wt%, MnO 23wt%, Al 2o 322wt%.Pickling process is adopted to prepare CuO-La 2o 3-CaO-Al 2o 3dehydrogenation commercial catalysts (spherical, Φ 5mm), wherein CuO content 15wt%, La 2o 3content 2wt%, Al 2o 3content 80wt%, CaO3wt%.Hydrogenation catalyst loadings 4Kg, dehydrogenation reactor catalyst loadings 1.2Kg.
Hydrogenation conditions: 2-butyl acetate raw material and hydrogen mol ratio are 30; 2-butyl acetate raw materials quality liquid hourly space velocity is 4.5h -1; Temperature of reaction is 240 DEG C; Reaction pressure is 8.0MPaG.
Dehydrogenation reaction conditions: sec-butyl alcohol quality liquid hourly space velocity is 10.0h -1; Temperature of reaction is 280 DEG C; Reaction pressure is 0.2MPaG.
Test steady running, after 72 hours, carries out material balance, 2-butyl acetate transformation efficiency 99.2%, methylethylketone yield 94.3%, ethanol yield 95.1%.
[embodiment 4]
According to the condition described in embodiment 1 and step, adopting coprecipitation method to prepare hydrogenation catalyst is CuO-ZnO-Al 2o 3-ZrO 2-MgO (cylindrical, Φ 5*5mm), wherein CuO content 65wt%, ZnO content 15wt%, MnO 23wt%, Al 2o 38wt%, MgO9wt%.Pickling process is adopted to prepare CuO-B 2o 3-MgO-Al 2o 3dehydrogenation commercial catalysts (spherical, Φ 5mm), wherein CuO content 15wt%, B 2o 3content 3wt%, Al 2o 3content 80wt%, MgO2wt%.Hydrogenation catalyst loadings 4Kg, dehydrogenation reactor catalyst loadings 0.6Kg.
Hydrogenation conditions: 2-butyl acetate raw material and hydrogen mol ratio are 30; 2-butyl acetate raw materials quality liquid hourly space velocity is 2.0h -1; Temperature of reaction is 220 DEG C; Reaction pressure is 5.0MPaG.
Dehydrogenation reaction conditions: sec-butyl alcohol quality liquid hourly space velocity is 8.0h -1; Temperature of reaction is 240 DEG C; Reaction pressure is 0.08MPaG.
Test steady running, after 72 hours, carries out material balance, 2-butyl acetate transformation efficiency 99.5%, methylethylketone yield 98.1%, ethanol yield 97.5%.
Obviously, in method provided by the invention, H-H reaction and dehydrogenation reaction are carried out jointly, achieve the comprehensive utilization of hydrogen.Reaction system highly selective obtain product methylethylketone and ethanol.In the method, sec-butyl acetate transformation efficiency is greater than 99%, and methylethylketone yield is higher than 95%, and ethanol yield is higher than 95%.
These are only preferred embodiment of the present invention, not in order to limit the present invention, all any changes done within principle of the present invention and spirit, equivalent replacement and improvement, all should be included within protection scope of the present invention.

Claims (7)

1. a method for coproduction methylethylketone and ethanol, comprises the following steps:
(1) 2-butyl acetate raw material and hydrogen feed enter hydrogenation unit, hydrogenation unit outlet streams enters the first separating unit and is separated, obtain unreacted 2-butyl acetate logistics, sec-butyl alcohol logistics, ethanol stream and byproduct streams respectively, described unreacted 2-butyl acetate logistics returns hydrogenation unit;
(2) described sec-butyl alcohol logistics enters dehydrogenation reaction unit, generate methylethylketone logistics and hydrogen gas stream, described methylethylketone logistics enters the second separating unit with the unreacted sec-butyl alcohol of dehydrogenation reaction unit and is separated, obtain methylethylketone logistics and unreacted sec-butyl alcohol logistics, described hydrogen gas stream returns hydrogenation unit, and described unreacted sec-butyl alcohol logistics returns dehydrogenation reaction unit.
2. the method for coproduction methylethylketone and ethanol according to claim 1, is characterized in that the 2-butyl acetate that described 2-butyl acetate raw material comprises n-butylene hydration method route and hybrid C 4 and acetic acid addition esterification process route and produces; The mol ratio of the 2-butyl acetate raw material and hydrogen feed that enter hydrogenation unit is 5-80.
3. the method for coproduction methylethylketone and ethanol according to claim 1, it is characterized in that the temperature of described hydrogenation unit is 150-350 DEG C, reaction pressure is 0.3-10.0MPaG, and the 2-butyl acetate raw materials quality liquid hourly space velocity of hydrogenation unit is 0.1-5.0h -1; The catalyzer that hydrogenation unit uses comprises the oxide compound of copper or copper.
4. the method for coproduction methylethylketone and ethanol according to claim 3, it is characterized in that catalyzer that hydrogenation unit uses comprises the oxide compound of copper or copper, second component and three components, second component is ZnO, ZrO 2, TiO 2, Al 2o 3, SiO 2in at least one, three components is La 2o 3, CeO 2, Fe 2o 3, CaO, MgO, MnO, B 2o 3, K 2o, BaO, Li 2at least one in O, in catalyzer, the oxide mass content of copper or copper is 19-75%, and second component mass content is 20-80%, and three components mass content is 1-40%.
5. the method for coproduction methylethylketone and ethanol according to claim 1, it is characterized in that the temperature of dehydrogenation reaction unit is 180-320 DEG C, pressure is 0.03-1.0MPaG, and the quality liquid hourly space velocity of sec-butyl alcohol is 1.0-10.0h -1, dehydrogenation catalyst is copper-based catalysts.
6. the method for coproduction methylethylketone and ethanol according to claim 1, its feature comprises the oxide compound of copper or copper, second component and three components at the catalyzer that dehydrogenation reaction unit uses, and second component is ZnO, Al 2o 3, SiO 2in at least one, three components is La 2o 3, Fe 2o 3, CaO, MgO, MnO, B 2o 3, K 2at least one in O, BaO, in catalyzer, the oxide mass content of copper or copper is 40-70%, and second component mass content is 29-59%, and three components mass content is 0.5-30%.
7. the method for coproduction methylethylketone and ethanol according to claim 1, is characterized in that described byproduct streams comprises acetaldehyde, vinyl acetic monomer, C8 alkene and diisobutyl ether.
CN201510455581.2A 2015-07-29 2015-07-29 Method for combined production of ethyl methyl ketone and ethanol Pending CN105130770A (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105503526A (en) * 2016-01-18 2016-04-20 上海华谊（集团）公司 Method for producing sec-butyl alcohol and co-producing ethanol through sec-butyl acetate hydrogenation
CN105903471A (en) * 2016-05-06 2016-08-31 北京石油化工学院 Catalyst for preparing MEK (Methyl Ethyl Ketone) by carrying out dehydrogenation on 2-butanol and preparation method and application thereof
CN106117025A (en) * 2016-06-23 2016-11-16 九江齐鑫化工有限公司 Sec-butyl alcohol Dichlorodiphenyl Acetate secondary butyl ester transfer hydrogenation produces the process of butanone simultaneously
CN106140170A (en) * 2016-06-23 2016-11-23 九江齐鑫化工有限公司 A kind of alcohol is to carboxylate transfer hydrogenation catalyst and preparation method thereof
CN115974660A (en) * 2022-12-15 2023-04-18 湖南中创化工股份有限公司 Method for preparing methyl ethyl ketone by taking sec-butyl acetate as raw material

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105503526A (en) * 2016-01-18 2016-04-20 上海华谊（集团）公司 Method for producing sec-butyl alcohol and co-producing ethanol through sec-butyl acetate hydrogenation
CN105903471A (en) * 2016-05-06 2016-08-31 北京石油化工学院 Catalyst for preparing MEK (Methyl Ethyl Ketone) by carrying out dehydrogenation on 2-butanol and preparation method and application thereof
CN106117025A (en) * 2016-06-23 2016-11-16 九江齐鑫化工有限公司 Sec-butyl alcohol Dichlorodiphenyl Acetate secondary butyl ester transfer hydrogenation produces the process of butanone simultaneously
CN106140170A (en) * 2016-06-23 2016-11-23 九江齐鑫化工有限公司 A kind of alcohol is to carboxylate transfer hydrogenation catalyst and preparation method thereof
CN106140170B (en) * 2016-06-23 2019-06-25 九江齐鑫化工有限公司 A kind of alcohol is to carboxylate transfer hydrogenation catalyst and preparation method thereof
CN115974660A (en) * 2022-12-15 2023-04-18 湖南中创化工股份有限公司 Method for preparing methyl ethyl ketone by taking sec-butyl acetate as raw material

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Application publication date: 20151209