CN106278816A - A kind of method that cellulose two-step method prepares ethanol and normal propyl alcohol - Google Patents

A kind of method that cellulose two-step method prepares ethanol and normal propyl alcohol Download PDF

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Publication number
CN106278816A
CN106278816A CN201510246428.9A CN201510246428A CN106278816A CN 106278816 A CN106278816 A CN 106278816A CN 201510246428 A CN201510246428 A CN 201510246428A CN 106278816 A CN106278816 A CN 106278816A
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cellulose
catalyst
tungsten
normal propyl
propyl alcohol
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CN106278816B (en
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王爱琴
徐刚
张涛
郑明远
庞纪峰
王�华
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Dalian Institute of Chemical Physics of CAS
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Dalian Institute of Chemical Physics of CAS
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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
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/02—Monohydroxylic acyclic alcohols
    • C07C31/08—Ethanol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/02—Monohydroxylic acyclic alcohols
    • C07C31/10—Monohydroxylic acyclic alcohols containing three carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters

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

Abstract

The invention provides a kind of cellulose two-step method and prepare ethanol, the method for normal propyl alcohol.Comprise the steps: in (1) alcohol solvent system with cellulose as raw material, under the first catalyst action, react generation ethyl glycolate, lactate with alcohol；(2) the liquid mixing product obtained to step (1) adds the second catalyst, is passed through hydrogen and carries out hydrogenation and obtain ethanol, normal propyl alcohol.The present invention is esterified and is hydrogenated with two-step reaction by alcohol, and cellulose conversion ratio can reach 100%, and ethanol, normal propyl alcohol productivity, up to more than 70%, reduce separation costs simultaneously, provides a new way for high-efficiency comprehensive utilization cellulose.

Description

A kind of method that cellulose two-step method prepares ethanol and normal propyl alcohol
Technical field
The present invention relates to cellulose production field, particularly relate to a kind of cellulose two-step method and prepare Ethanol, the method for normal propyl alcohol.
Background technology
Lignocellulose biomass be the most unique predictable can for the mankind provide material and The sustainable resource of fuel, rich reserves, wide material sources, there is universality, easily taking property, energy Effectively solve the problem that traditional biological fuel " strives grain with people ".Wherein cellulosic ethanol is as second For bio-fuel it is considered to be one of the most rising non-grain bio-fuel, have wide Development prospect.
At present, the production method of cellulosic ethanol is mainly biochemical process, will cellulose water Solve generation can ferment monosaccharide, and then generated the technology [document of alcohol fuel by fermentable 1:Mohammad J, Enzyme-based hydrolysis processes for ethanol from Lignocellulosic materials:A review.Bioresources, 2 (4): 707-738.] and just Propanol is mainly obtained [document 2: the cleaning of a kind of preparing normal propyl alcohol by propionaldehyde hydrogenation by hydrogenation of propionaldehyde Production technology, CN101774887A], the former is high for enzyme cost and the cycle is long, and latter raw material relies on In petroleum resources, and catalyst is noble metal, Response time is long, all has certain limitation.
Cellulose two-step method designed by the present invention prepares ethanol, and the method raw material of normal propyl alcohol is green Renewable, process step-wise controllable, catalyst can be separately recovered, and catalyst is cheap and product separates Solvent recovery cost is relatively low.
Summary of the invention
It is an object of the invention to provide a kind of cellulose and prepare ethanol, the method for normal propyl alcohol, first will Cellulose catalytic is converted into ethyl glycolate, lactate, then carry out hydrogenation obtain ethanol, positive third Alcohol.
For achieving the above object, the technical scheme that the present invention takes is:
With cellulose as raw material in alcohol solvent system, exist with alcohol under the first catalyst action 180-300 DEG C of reaction 0.5-3h generates ethyl glycolate, lactate；Produce to the liquid mixing obtained Thing adds the second catalyst, is passed through 1-7MPa hydrogen and carries out being hydrogenated with 1-3h at 220-300 DEG C Obtain the mixture of ethanol and normal propyl alcohol.
Alcoholic solvent is at least one in methanol, normal propyl alcohol or isopropanol.First catalyst is tungsten Oxide, the sulfide of tungsten, the chloride of tungsten, the carbide of tungsten, the hydroxide of tungsten, Tungsten bronze, wolframic acid, tungstates, metatungstic acid, metatungstate, para-tungstic acid, paratungstate, mistake At least one in oxygen wolframic acid, peroxotungstate, heteropoly acid containing tungsten or heteropoly acid containing tungsten salt.
The ethyl glycolate produced in step (1) is methyl glycollate, ethyl glycolate, ethanol At least one in propyl propionate, alcohol acid isopropyl, lactate is methyl lactate, ethyl lactate, At least one in propyl lactate or isopropyl lactate.
Second catalyst uses silicon dioxide to be carrier, with Cu as active component or chief active Component, contains Ag, Mg, Ca, Ba, Zn, Zr, Co, Cr, Ni, Mn, Sn, Au, Pt, Pd simultaneously, One or more in Ru or Re are as auxiliary agent, and wherein the mass fraction of Cu is 0.5-40%. Auxiliary agent mass fraction is 0-5%, and remaining is carrier.
Described alcoholic solvent consumption is 10-200 times of cellulose quality, and described first catalyst is used Amount is the 5%-50% of cellulose quality, and described second catalyst amount is cellulose quality 10-40%.
Present invention have the advantage that
1., relative to existing ethanol, propanol production technology, prepared by two-step method involved in the present invention Technological reaction raw material green is renewable, with short production cycle, totally realizes sustainable.
The catalyst chief active center of step (2) the most involved in the present invention is Cu, relative to The noble metals such as some Ru, Ni are compared, and catalyst cost is lower.
3. the alcoholic solvent that the present invention relates to is relative to the aqueous solvent boiling point in existing hydrolysis hydrogen addition technology Lower, follow-up product is separated and solvent recovery cost is lower.
Detailed description of the invention
Below by specific embodiment, the present invention is described in detail, but these embodiments are not to this The Composition of contents of invention limits.
Embodiment 1
Cs2.5H0.5PW12O40The preparation of catalyst
Respectively 2.5g CS2CO3The H obtained with 18.12g pretreatment3PW12O40×6H2O is made into 0.1 Mol × L-1 and 0.08mol × L-1Solution, 0.1 × mol × L-1Cs2CO3Solution is with 1mL × min-1 Speed be at room temperature added drop-wise to 0.08mol × L-1H3PW12O40In solution.Drip complete, continue After continuous stirring 0.5h, stand 20h at room temperature.Then slow evaporation moisture under 323K, Obtain white solid, then about 110 DEG C drying, with front at 300 DEG C of roasting 2h, specific surface Amass as 108m2g-1。
Embodiment 2
W2The preparation of C/AC: claim 50g activated carbon (AC), 250mL 33wt%HNO3, it is placed in 500mL In there-necked flask, 80 DEG C of water bath processing 24h, washing, to neutral, dries 24h for 120 DEG C.By 1g Pretreated AC pours in the aqueous solution containing 0.588g ammonium metatungstate, does through 120 DEG C of baking ovens After dry, this catalyst precarsor carrying out in hydrogen temperature programmed reduction, concrete course of reaction is: 550 DEG C are risen to the heating rate of 8.8 DEG C/min, then with the intensification of 1 DEG C/min by room temperature Ramp is to 900 DEG C and keeps 1h, and hydrogen flow rate is 120mL/min.Prepared urges In agent, the theoretical loading of W is 30wt%.
Embodiment 3
Take 0.3g SBA-15 to be dispersed in 30mL ethanol, 0.13g phosphotungstic acid is dissolved in 10mL In ethanol, then drop to above-mentioned suspension, stirring dipping 24h, solvent evaporated, be dried, It is prepared as the solid-carried catalyst that load capacity is 30%.Wherein SBA-15 preparation process is: take 2.0 G P123 is dissolved in 15mL water, and then dropping 55mL hydrochloric acid, is warming up to 40 DEG C at least Stirring 2-3h, drips 4.24g tetraethyl orthosilicate, reacts 24h, then shift at 40 DEG C To hydrothermal reaction kettle, stand 24h at 100 DEG C, use sand core funnel sucking filtration, be washed to neutrality, Remaining solid is placed in calcination 6h at 500 DEG C after first drying at 60 DEG C again.
Embodiment 4
At room temperature by 7.56g Cu (NO3)2×3H2O is dissolved in 100mL deionized water, adds dense ammonia Water regulation pH value, to 9.0, adds 8.0g SiO2.After stirring 20min, mixture is turned Move in ice-water bath, under agitation with 15mL × min-1Speed add deionized water, dilution Filter to 2L.After being washed with deionized 3 times, it is dried overnight at 120 DEG C, then Roasting 4h at 450 DEG C.The 3h. that reduces at 350 DEG C before reaction obtains 20%-Cu/SiO2。
Embodiment 5
By 1.90g Cu (NO3)2×3H2O is dissolved in 100mL deionized water, slowly drips in solution 30min is stirred under room temperature after adding the ammonia of 11mL 28wt.%, molten to above-mentioned cupric ammine complex Liquid adds the load containing 4.0g difference ferrum oxide (magnesium oxide, cobalt oxide) with silica ratios After body, be vigorously agitated again 2h, the initial pH=11-12 of solution, then heat to 90 DEG C vaporized The ammonia of amount and solvent so that copper species deposit to ferrum oxide and silica support in the process On, stop evaporation when being neutrality to solution, centrifugal, at 120 DEG C, it is dried 12h after washing, so After at 450 DEG C roasting 4h.The front 3h that reduces at 350 DEG C of reaction.So prepare 5%Fe-15%Cu/SiO2, 5%Mg-15%Cu/SiO2, 5%Co-15%Cu/SiO2。
Embodiment 6
Catalyzed conversion is tested: by 0.5g cellulose, 0.2g the first catalyst H2WO4, and 50ml Methanol joins in 100ml reactor, is stirred with the speed of 800 turns/min, simultaneously It is warmed up to 260 DEG C, reacts 2h.After reaction terminates, be down to room temperature, 5000rpm is centrifuged 10min Separate product liquid and catalyst.Take 0.2g the second catalyst 20%Cu/SiO2(join liquid In body product, it is passed through 3MPa H2, it is warming up to 260 DEG C of reaction 2h, after reaction terminates, is down to Room temperature, 5000rpm are centrifuged 10min and separate product liquid and catalyst.Product liquid uses Agilent company 7890B chromatographic, is furnished with hydrogen flame (FID) detector, from Dynamic injector.HP-INNOWAX capillary column (30m × 250 μ m 0.5 μm .), Carrier gas is nitrogen, temperature programming: stops 3min at 45 DEG C, then rises to 5 DEG C/min speed 100 DEG C, rise to 250 DEG C with 12 DEG C/min subsequently and stop 3min.Detector temperature 270 DEG C, Hydrogen flowing quantity 30ml/min, air mass flow 400ml/min, N2Flow 35ml/min.Injection port Temperature 220 DEG C, sample size 1 μ l, split ratio 20:1.
Cellulose conversion ratio is calculated by following formula:
Ethanol, normal propyl alcohol yield computing formula following (wherein in reactant cellulose phosphorus content by element Analyser determines):
Other product liquid and gaseous product (CO, CO2, CH4Deng) do not calculate its yield.
Embodiment 7
Replace the first catalyst and the kind of the second catalyst, the same embodiment of other reaction conditions 6, relatively all kinds of tungsten-containing catalyst H2WO4, WO3, Na2WO4,AMT,W2C/AC, HPW/SBA-15,Cs2.5H0.5PW12O40And Cu-contained catalyst 20%Cu/SiO2, 5%Fe-15%Cu/SiO2, 5%Mg-15%Cu/SiO2, 5%Co-15%Cu/SiO2Under catalysis The catalyzed conversion result of cellulose, is shown in Table 1.
The comparison of cellulose catalytic conversion performance on the various catalyst of table 1
It is as shown in the table, and cellulose can be on various tungstenics involved in the present invention and Cu-contained catalyst It is converted into ethanol, normal propyl alcohol with high yield.Wherein, W2C/AC Fe-Cu/SiO2On can make Ethanol, normal propyl alcohol yield reaches 66.3% and 7.8%.
Embodiment 8
Replacing solvent species, other reaction conditions, with embodiment 6, compare methanol, normal propyl alcohol body Cellulose catalytic conversion results in system, is shown in Table 2.
The comparison of cellulose catalytic conversion performance in the various alcoholic solvent of table 2
It is as shown in the table, and cellulose can be efficiently converted in all kinds of alcoholic solvents involved in the present invention Ethanol, normal propyl alcohol.
Embodiment 9
The comparison of cellulose catalytic conversion performance at a temperature of differential responses.It is shown in Table 3, except reaction temperature Outside degree difference, other reaction conditions are with embodiment 6.
The comparison of cellulose catalytic conversion performance at a temperature of table 3 differential responses
As can be seen from the table, within the scope of certain temperature, cellulose all has excellent ethanol, Normal propyl alcohol yield.
Embodiment 10
The comparison of cellulose catalytic conversion performance under the differential responses time.It is shown in Table 4, except the response time not With outward, other reaction conditions are with embodiment 6.
The comparison of cellulose catalytic conversion performance under the table 4 differential responses time
As can be seen from the table, in the range of the regular hour, cellulose all has excellent ethanol, Normal propyl alcohol yield.

Claims (7)

1. the method that a cellulose two-step method prepares ethanol and normal propyl alcohol, it is characterised in that include Following steps:
(1) alcoholic solvent adds cellulose, react under the first catalyst action；
(2) mix products obtained to step (1) adds the second catalyst, is passed through hydrogen and carries out instead The mixture of ethanol and normal propyl alcohol should be obtained.
2. the method for claim 1, it is characterised in that: the alcohol described in step (1) is molten Agent is the one in methanol, normal propyl alcohol or isopropanol or two kinds or three kinds.
3. the method for claim 1, it is characterised in that: first described in step (1) Catalyst is the oxide of tungsten, the sulfide of tungsten, the chloride of tungsten, the carbide of tungsten, tungsten Hydroxide, tungsten bronze, wolframic acid, tungstates, metatungstic acid, metatungstate, para-tungstic acid, secondary In tungstates, peroxide wolframic acid, peroxotungstate, heteropoly acid containing tungsten or heteropoly acid containing tungsten salt one Plant or more than two kinds.
4. the method for claim 1, it is characterised in that: second described in step (2) Catalyst is with silicon dioxide as carrier, with Cu as active component, contain simultaneously Ag, Mg, Ca, Ba, Zn, Zr, Co, Cr, Ni, Mn, Sn, Au, Pt, Pd, Ru or Re In one or two or more kinds as auxiliary agent, wherein the mass fraction of Cu is 0.5-40%, helps Agent mass fraction is 0-5%, and remaining is carrier.
5. the method for claim 1, it is characterised in that: alcoholic solvent described in step (1) Quality is 10-200 times of cellulose quality, and described first catalyst quality is cellulose quality 5%-50%, cellulose during the second catalyst quality is step (1) described in step (2) The 10-40% of quality.
6. the method for claim 1, it is characterised in that: the reaction described in step (1), Reaction temperature is 180-300 DEG C, and the response time is 0.5-3h.
7. the method for claim 1, it is characterised in that: the reaction described in step (2), Reaction temperature is 220-300 DEG C, and the response time is 1-3h, and Hydrogen Vapor Pressure is 1-7MPa.
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CN107970932A (en) * 2017-11-23 2018-05-01 黑龙江省能源环境研究院 A kind of catalytic cellulose converts polynary alcohol catalyst and preparation method thereof and application method
CN108623436A (en) * 2018-04-08 2018-10-09 华东师范大学 A kind of one kettle way conversion cellulose is the method for bio-ethanol
CN109289909A (en) * 2018-10-16 2019-02-01 郑州大学 A kind of complicated sugared conversion of catalysis prepares the catalyst of lactate
CN109833884A (en) * 2017-11-29 2019-06-04 中国科学院大连化学物理研究所 A kind of methyl glycollate hydrogenolysis prepares catalyst of ethyl alcohol and its preparation method and application
CN110385131A (en) * 2018-04-18 2019-10-29 中国科学院大连化学物理研究所 A kind of catalyst of C2 acid esters preparation of ethanol by hydrogenating and its preparation and application
CN111217672A (en) * 2018-11-25 2020-06-02 中国科学院大连化学物理研究所 Method for preparing ethanol from carbohydrate
CN115974646A (en) * 2021-10-14 2023-04-18 中国科学院大连化学物理研究所 Method for preparing ethanol by catalyzing carbohydrate with monatomic catalyst

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Publication number Priority date Publication date Assignee Title
CN107970932A (en) * 2017-11-23 2018-05-01 黑龙江省能源环境研究院 A kind of catalytic cellulose converts polynary alcohol catalyst and preparation method thereof and application method
CN109833884A (en) * 2017-11-29 2019-06-04 中国科学院大连化学物理研究所 A kind of methyl glycollate hydrogenolysis prepares catalyst of ethyl alcohol and its preparation method and application
CN108623436A (en) * 2018-04-08 2018-10-09 华东师范大学 A kind of one kettle way conversion cellulose is the method for bio-ethanol
CN110385131A (en) * 2018-04-18 2019-10-29 中国科学院大连化学物理研究所 A kind of catalyst of C2 acid esters preparation of ethanol by hydrogenating and its preparation and application
CN109289909A (en) * 2018-10-16 2019-02-01 郑州大学 A kind of complicated sugared conversion of catalysis prepares the catalyst of lactate
CN109289909B (en) * 2018-10-16 2021-03-19 郑州大学 Catalyst for preparing lactate by catalyzing conversion of complex sugar
CN111217672A (en) * 2018-11-25 2020-06-02 中国科学院大连化学物理研究所 Method for preparing ethanol from carbohydrate
CN111217672B (en) * 2018-11-25 2021-08-17 中国科学院大连化学物理研究所 Method for preparing ethanol from carbohydrate
CN115974646A (en) * 2021-10-14 2023-04-18 中国科学院大连化学物理研究所 Method for preparing ethanol by catalyzing carbohydrate with monatomic catalyst

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