CN109896923A - A kind of method that ethyl alcohol conversion prepares high carbon primary alcohol on bicomponent catalyst - Google Patents
A kind of method that ethyl alcohol conversion prepares high carbon primary alcohol on bicomponent catalyst Download PDFInfo
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Abstract
The present invention provides the methods that ethyl alcohol conversion on a kind of bicomponent catalyst prepares high carbon primary alcohol.The catalyst of this method includes catalyst A and catalyst B, the active constituent of catalyst A is the 8th, 9, the transition metal iron of 10 races, cobalt, nickel, ruthenium, rhodium, palladium, iridium, one of platinum or two kinds or more, and catalyst B is one or more of alkali, formates, carbonate and bicarbonate in I A group alkali metal；It is stirred to react in reaction kettle or in fixed bed reaction；Reaction atmosphere is one or more of nitrogen, helium, argon gas, reaction temperature >=120 DEG C.Compared with prior art, the raw material that the present invention uses is bio-ethanol, the advantages that there are rich reserves, environmental-friendly, green non-pollution.The advantages that even carbon primary alconol generated simultaneously, mainly includes butanol, hexanol, octanol, economical high, utilization ways are wide.In addition, this process catalyst is cheap, reaction selectivity is high, stability is good, product can be easily separated, there is important economic value and potential industrial prospect.
Description
Technical field
The present invention relates to bioenergy development technique fields more particularly to a kind of alcohol catalysis conversion to prepare high carbon primary alcohol
Method.
Background technique
With the aggravation of exhaustion, the environmental pollution of fossil fuel and the fast development of fermentation technique, ethyl alcohol is as a kind of new
The energy chemistry platform chemicals of type cause the extensive attention of people.By 2010, the yield of ethyl alcohol reached 60,000,000,000 liters.At present
Most ethyl alcohol is mainly used for oil product addition, so that part replaces fuel oil.However, the limitation compatible based on safety and solvent,
Ethyl alcohol additive amount in oil product is limited, can only be less than 10%, this serious development and application for constraining ethyl alcohol.
Corresponding, the higher alcohols such as butanol have higher adding proportion, and do not influence the normal of available engine
Operating.Meanwhile the low molecules idol carbon alcohol such as butanol, hexanol is also a kind of intermediate chemical, thus it is widely used in fragrance addition
The various fields such as agent, medicine intermediate, life science, tool has been widely used and industrialization potential.
Preparation method that there are two types of the idol carbon alcohol such as green butanol, a method of for biomass direct fermentation, abbreviation ABE work
Skill, this process primary product are ethyl alcohol, butanol and acetone.This process reaction time is long, reaction efficiency is low, enzyme cost compared with
It is high.Another method is that catalysis ethanol conversion prepares the even carbon alcohol such as butanol.The most important process of this process is " borrowing hydrogen ".First
Ethyl alcohol dehydrogenation, dissociation on a catalyst, using aldol condensation, the hydrogen on last catalyst, which is then added in product, generates butanol etc.
Single methanol.At present under catalyst system, this reaction ethanol conversion is low, and dehydrogenation rate is slower, influences the progress of subsequent reactions.Together
When, ethyl alcohol is easy to happen intramolecular or intermolecular dehydration generates ethylene or ether, to reduce the selectivity of product.In addition,
Metal is easy to reunite, grow up in reaction, so as to cause catalyst inactivation.Therefore, there are still larger for highly selective generation higher alcohols
Challenge.
Purpose provided by the invention is to provide the side that alcohol catalysis conversion on a kind of bicomponent catalyst prepares high carbon primary alcohol
Method, this method can significantly improve the yield of even carbon alcohol, reduce the generation of by-product in reaction process, the stability of catalyst and
Service life is improved significantly, and it is excellent that this method has that easy to operate, catalyst is at low cost, stability is good, reaction efficiency is high etc.
Point.
Summary of the invention
The purpose of the present invention is to provide the methods that ethyl alcohol conversion on a kind of bicomponent catalyst prepares high carbon primary alcohol.The party
Method is with easy to operate, catalyst is at low cost, economical and practical, the even carbon alcohol of production is high-efficient, low power consumption and other advantages.
To achieve the above object, the technical step that the present invention takes are as follows:
Using composite catalyst, realize that alcohol catalysis conversion prepares high carbon primary alcohol；The catalyst of this method includes catalyst A
With catalyst B, the active constituent of catalyst A is the 8th, 9, the transition metal iron of 10 races, cobalt, nickel, ruthenium, rhodium, palladium, iridium, in platinum
One or two or more kinds, catalyst B be one of alkali, formates, carbonate and bicarbonate in I A group alkali metal or
It is two or more；It is stirred to react in reaction kettle or in fixed bed reaction；Reaction atmosphere be one of nitrogen, helium, argon gas or
Two or more, reaction temperature is 120-350 DEG C.
Ethanol raw material can be aqueous, and water content is less than 20wt%；The high carbon primary alcohol product is butanol, hexanol, octanol, certain herbaceous plants with big flowers
One or more of alcohol.
When catalysis reaction carries out in a kettle, reactor is needed with one or more of nitrogen, helium, argon gas
Displacement, last filling pressure is 0.1-5MPa before reacting；The weight ratio of catalyst and reactant ethyl alcohol is between 1:1000-1:1；
Reaction time is 0.5-48 hours；Reaction temperature is between 150-250 DEG C.
Catalysis reaction on fixed bed reactors when carrying out, gas pressure 0.1-10MPa；It is catalyzed the mass space velocity of reaction
For 0.1-20h-1；Reaction temperature is between 180-350 DEG C.
The active constituent of catalyst A is the 8th, 9, the transition metal iron of 10 races, cobalt, nickel, ruthenium, rhodium, palladium, iridium, one in platinum
Kind or two kinds or more, carrier vector is that active carbon, aluminium oxide, silica, silicon carbide, zirconium oxide, zinc oxide, titanium dioxide are a kind of
Or two kinds or more；The mass ratio of active metal is 0.5-30%；Catalyst A is also possible to skeleton type catalyst, including skeleton iron,
Skeletal copper and skeletal nickel catalyst are also possible to matrix type alloy catalyst, including matrix type ferronickel, matrix type ambrose alloy, skeleton
Type copper and iron catalyst, the molar ratio of metal is 1:10-10:1 in alloy catalyst.
Catalyst A preparation method is infusion process either coprecipitation；The preparation method of skeleton catalyst is metal melting
Then dealuminzation or be coprecipitation.
Catalyst B is specially sodium hydroxide, sodium methoxide, sodium bicarbonate, potassium carbonate, potassium hydroxide, lithium hydroxide, lithium carbonate
One or more of.
Catalyst A and catalyst B is added in reaction kettle simultaneously, and the mass ratio of catalyst A and catalyst B are 1:10-10:
1, total catalyst quality and reaction substrate weight ratio are lower than 1:10；When reacting in fixed bed reactors, catalyst A is attached to fixation
In bed reactor, catalyst B is pumped into reactor with ethanol solution, and the mass concentration of catalyst B is 1:10-10:1.
Catalyst A and catalyst B is added in reaction kettle simultaneously, and the mass ratio of catalyst A and catalyst B are 1:5-5:1,
Total catalyst quality and reaction substrate weight ratio are lower than 1:20；When reacting in fixed bed reactors, catalyst A is attached to fixed bed
In reactor, catalyst B is dissolved in ethanol solution to be pumped into reactor with ethanol solution, and the mass concentration of catalyst B is
1:5-5:1。
The butanol selectivity that this process generates is more than 60%, and for higher alcohols selectively more than 85%, gaseous product is selectively low
In 10%.
The high carbon primary alcohol is one or more of butanol, hexanol, octanol, certain herbaceous plants with big flowers alcohol.
The present invention has the advantage that
1. ethanol production is big, source is sufficient, the even carbon alcohol such as butanol that this process generates has in fields such as fuel, chemicals
It is widely applied.
2. catalyst is easy preparation, at low cost, stability is good, and product can be easily separated use, and whole process has preferably
Economy and practicability, meet the requirement of sustainable development, biomass conversion in be with a wide range of applications.
Below by specific embodiment, the present invention is described in detail, but these embodiments are not to the contents of the present invention
It is construed as limiting.
Specific embodiment
Embodiment 1
The preparation method of different catalysts
The preparation of alloy catalyst:
Weigh 0.01mol nitric acid M (M is one or more of Ni and Co, Cu, Zn) and 0.04mol ferric nitrate (Fe
(NO3)3·9H2O it) is dissolved in 100mL deionized water, solution A is made.Separately weigh 0.06mol natrium carbonicum calcinatum (Na2CO3) be dissolved in
In 60mL deionized water, is mixed with the NaOH solution of 10mL 3M, obtain solution B.Solution B is placed in 35 DEG C of water-baths, in play
Under strong stirring condition, solution A is added thereto with the speed of 3mL/min, and it is 10 that a small amount of NaOH solution, which is added, to adjust pH.It will sink
Form sediment the crystallization 18h in 65 DEG C of water-baths.Through filtering, after washing, sample is dried at 80 DEG C.400 DEG C of roastings, 550 DEG C of reduction obtain
Dilval.Different alloy catalysts is prepared in same reason.
The preparation of impregnation catalyst agent:
Infusion process prepares activated carbon supported Ni catalyst, detailed process are as follows: weighs 6.27gNi (NO3)2·6H2O is dissolved in
In 10mL deionized water, separately weighs 0.74g active carbon and be added in above-mentioned nickelous nitrate solution under stiring, by excessive moisture after dipping
Drying, obtained sample roast 2h at 300 DEG C.Sample uses 10%H at 500 DEG C after above-mentioned gained roasting2/ He restores 1h,
Obtain infusion process Ni base catalyst.The catalyst such as Ir/AC are prepared in same reason.
Skeleton type catalyst preparation:
Skeleton type catalyst: Raney's nickel, raney iron, Lei Nitong are to activate dealuminzation by alloy powder alkali to obtain.Activation
Temperature is 25 DEG C, and 500rpm stirring, naoh concentration 20% activates 2 hours.
Embodiment 2
Reaction condition:
Fixed bed reaction:
Catalyzed conversion experiment carries out in fixed bed reactors, and actual conditions are as follows: catalyst prepared by 2g embodiment 1
A presoma, is added in fixed bed reactors, online hydrogen reducing, hydrogen flow rate 60ml/min, and reduction temperature is 600 DEG C,
Recovery time 2h.
Cool down after reduction, is passed through nitrogen, pressure 3MPa, gas flow rate 20ml/min.It is raised to reaction temperature and is pumped into original
Material and catalyst B reaction, liquid product and gas-phase product use gas chromatographic analysis respectively.
Still reaction:
Catalyzed conversion experiment carries out in a kettle, and actual conditions are as follows: catalyst and second being added in 100ml reaction kettle
Alcohol, nitrogen are replaced 5 times, and 0.2MPa nitrogen is filled with.Concentration of alcohol is 98wt%, and 220 DEG C of reaction temperature, ethyl alcohol volume 30ml is urged
The quality of agent A and catalyst B are respectively 0.2g and 0.2g, and reaction is for 24 hours.
Embodiment 3
It is that alcohol catalysis conversion prepares even carbon alcohol as a result, remaining reaction condition and implementing in reaction kettle under different catalysts
Example 2 is identical:
Alcohol catalysis conversion prepares reaction result (concentration of alcohol 98wt%, the reaction temperature of even carbon alcohol under 1 different catalysts of table
220 DEG C of degree, the quality of ethyl alcohol volume 30ml, catalyst A and catalyst B are respectively 0.2g and 0.2g, for 24 hours)
From response data, it can be seen that, catalyst A and catalyst B generate shadow to ethanol conversion and butanol selectivity
It rings.Ethanol conversion reaches 35.2% on dilval+ethyl alcohol sodium catalyst, and butanol and higher alcohols are selectively respectively
74.5% and 96.2%.Even if closing in the group of Raney Fe and lithium hydroxide, ethanol conversion also reaches 30.6%, and high
Carbon alcohol selectively reaches 95.3%.
Embodiment 4
On fixed bed reactors under different condition, alcohol catalysis conversion prepares the result of even carbon alcohol:
Alcohol catalysis conversion prepares reaction result (concentration of alcohol 98wt%, the reaction temperature of even carbon alcohol under 2 different catalysts of table
The quality of 250 DEG C, flow velocity 0.1ml/min, catalyst A of degree is 1.5g, and catalyst B is sodium ethoxide, is dissolved in ethanol solution, dense
Degree is 1%, and the air speed of ethyl alcohol is 0.3h-1)
From response data, it can be seen that, catalyst A and catalyst B combination also have higher reaction on fixed bed reactors
Activity.Ethanol conversion reaches 26.9% especially on dilval, and butanol and higher alcohols are selectively respectively 77.4% He
90.3%.
Embodiment 5
In reaction kettle under the conditions of differential responses, ethyl alcohol conversion prepares the reaction result of even carbon alcohol:
(catalyst is Ni-Fe-HT and ethyl alcohol to the result of the even carbon alcohol of alcohol catalysis conversion preparation under the conditions of 3 differential responses of table
The quality of sodium, concentration of alcohol 98wt%, ethyl alcohol volume 30ml, catalyst A and catalyst B is respectively 0.2g and 0.2g)
From response data, it can be seen that, reaction temperature and time are very big on reaction influence.High reaction temperature promotes ethyl alcohol to turn
Change, but be easy to happen the further degradation of product butanol, global selectivity is lower.Extending the reaction time can also be such that product selects
Selecting property reduces.Higher product yield in order to obtain, it should balanced reaction temp and reaction time.
Embodiment 6
The stability of catalyst.
(catalyst is Ni-Fe-HT and sodium ethoxide, concentration of alcohol 98wt%, ethyl alcohol volume to the test of 4 catalyst stability of table
The quality of 30ml, catalyst A and catalyst B are respectively 0.2g and 0.2g；230 DEG C, for 24 hours；Recycling catalyst A)
As shown in table 4, the Ni-Fe catalyst stability with higher of coprecipitation preparation, it is living using 7 rear catalysts
Property is not decreased obviously.
Comparative example
Different Results compare.
Catalyst activity compares on the different documents of table 5
By the comparison with document, it can be found that the application has and the progress of document substance more outstanding, this Shen
Catalyst structure please is simple, is easy preparation, and can be recycled, practicability with higher.
The above, the specific embodiment of part only of the present invention, but protection scope of the present invention is not limited to that,
Also any restrictions caused by not because of the precedence of each embodiment to the present invention, it is any to be familiar with person skilled in the art of the present invention
In the technical scope that the present invention reports, it can be changed or replace easily, should be covered by the protection scope of the present invention.
Therefore, protection scope of the present invention is not limited only to above embodiments, it should be subject to the protection scope in claims.
Claims (10)
1. a kind of method that ethyl alcohol conversion prepares high carbon primary alcohol on bicomponent catalyst, which is characterized in that composite catalyst is used,
Realize that alcohol catalysis conversion prepares high carbon primary alcohol；The catalyst of this method includes catalyst A and catalyst B, the activity of catalyst A
Ingredient is the 8th, 9, the transition metal iron of 10 races, cobalt, nickel, copper, ruthenium, rhodium, palladium, iridium, one of platinum or two kinds or more, catalyst
B is one or more of alkali, formates, carbonate and bicarbonate in I A group alkali metal；It is stirred in reaction kettle
It reacts or in fixed bed reaction；Reaction atmosphere is one or more of nitrogen, helium, argon gas, and reaction temperature is
120-350℃。
2. according to the method for claim 1, it is characterised in that: the ethanol raw material can be aqueous, and water content is less than
20wt%；The high carbon primary alcohol product is one or more of butanol, hexanol, octanol, certain herbaceous plants with big flowers alcohol.
3. according to the method for claim 1, it is characterised in that: when the catalysis reaction carries out in a kettle, reactor
It needs to be replaced with one or more of nitrogen, helium, argon gas, last filling pressure is 0.1-5MPa before reacting；Catalysis
The weight ratio of agent and reactant ethyl alcohol is between 1:1000-1:1；Reaction time is 0.5-48 hours；Reaction temperature is 150-250
Between DEG C.
4. according to the method for claim 1, it is characterised in that: the catalysis is reacted when carrying out on fixed bed reactors,
Gas pressure is 0.1-10MPa；The mass space velocity of catalysis reaction is 0.1-20h-1；Reaction temperature is between 180-350 DEG C.
5. according to the method for claim 1, it is characterised in that: the active constituent of the catalyst A is the 8th, 9,10 races
One of transition metal iron, cobalt, nickel, copper, ruthenium, rhodium, palladium, iridium, platinum or two kinds or more, carrier are active carbon, aluminium oxide, oxidation
Silicon, silicon carbide, zirconium oxide, zinc oxide, titanium dioxide are one or two or more kinds of；The mass ratio of active metal is 0.5-30%；It urges
Agent A is also possible to skeleton type catalyst, including skeleton iron, skeletal copper and skeletal nickel catalyst, is also possible to matrix type alloy
Catalyst, including matrix type ferronickel, matrix type ambrose alloy, matrix type copper and iron catalyst.
6. catalyst according to claim 5, it is characterised in that: catalyst A preparation method is that infusion process is either coprecipitated
Shallow lake method；The preparation method of skeleton catalyst is metal melting and then dealuminzation or is coprecipitation.
7. according to the method for claim 1, it is characterised in that: catalyst B is specially sodium hydroxide, sodium methoxide, bicarbonate
One or more of sodium, potassium carbonate, potassium hydroxide, lithium hydroxide, lithium carbonate.
8. according to the method for claim 1, it is characterised in that: catalyst A and catalyst B is added in reaction kettle simultaneously,
The mass ratio of catalyst A and catalyst B are 1:10-10:1, and total catalyst quality and reaction substrate weight ratio are lower than 1:10；Solid
When reacting in fixed bed reactor, catalyst A is attached in fixed bed reactors, and catalyst B is dissolved in molten with ethyl alcohol in ethanol solution
Liquid is pumped into reactor, and the mass concentration of catalyst B is 1:10-10:1.
9. according to the method for claim 1 with claim 9 range, it is characterised in that: catalyst A and catalyst B are simultaneously
It is added in reaction kettle, the mass ratio of catalyst A and catalyst B are 1:5-5:1, total catalyst quality and reaction substrate weight ratio
Lower than 1:20；When reacting in fixed bed reactors, catalyst A is attached in fixed bed reactors, and catalyst B is pumped with ethanol solution
Enter into reactor, the mass concentration of catalyst B is 1:5-5:1.
10. according to the method for claim 1, it is characterised in that: the butanol selectivity that this process generates is more than 60%, high-carbon
For alcohol selectively more than 85%, gaseous product is selectively lower than 10%.
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| CN113019404A (en) * | 2021-03-23 | 2021-06-25 | 中国科学院兰州化学物理研究所 | Nickel-based catalyst for synthesizing high-carbon alcohol and preparation method and application thereof |
| CN113145155A (en) * | 2021-03-09 | 2021-07-23 | 广东工业大学 | Nitrogen-doped carbon-coated nickel catalyst applied to assembly of bioethanol to synthesize high-carbon alcohol and preparation method thereof |
| CN114713244A (en) * | 2021-01-06 | 2022-07-08 | 浙江省化工研究院有限公司 | Hydrodechlorination catalyst, preparation method and application thereof |
| WO2022247717A1 (en) * | 2021-05-28 | 2022-12-01 | 浙江工业大学 | Method for synthesizing higher alcohol by means of catalytic conversion of ethanol |
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Cited By (6)
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| CN113145155A (en) * | 2021-03-09 | 2021-07-23 | 广东工业大学 | Nitrogen-doped carbon-coated nickel catalyst applied to assembly of bioethanol to synthesize high-carbon alcohol and preparation method thereof |
| WO2022188432A1 (en) * | 2021-03-09 | 2022-09-15 | 广东工业大学 | Nitrogen-doped carbon coated nickel catalyst applied to synthesis of high-carbon alcohol by assembly of bioethanol, and preparation method therefor |
| CN113019404A (en) * | 2021-03-23 | 2021-06-25 | 中国科学院兰州化学物理研究所 | Nickel-based catalyst for synthesizing high-carbon alcohol and preparation method and application thereof |
| WO2022247717A1 (en) * | 2021-05-28 | 2022-12-01 | 浙江工业大学 | Method for synthesizing higher alcohol by means of catalytic conversion of ethanol |
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