CN109896922A - A kind of lignocellulosic efficiently separates and realizes the method that full constituent utilizes - Google Patents
A kind of lignocellulosic efficiently separates and realizes the method that full constituent utilizes Download PDFInfo
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Abstract
The method that full constituent utilizes is efficiently separated and realized the present invention provides a kind of lignocellulosic, realizes that lignin and cellulose efficiently separate by pretreatment, obtained cellulose can Efficient Conversion be ethylene glycol.It is renewable resource with raw material, exists and do not strive the advantages of grain strives ground with people.In addition, preprocess method mild condition of the invention, solvent are recycled, obtain the advantages that solid matter content of cellulose is high, lignin is with high purity.Solid cellulose substance highly selective can be converted into ethylene glycol, realize the highly selective conversion from protist system to ethylene glycol.Lignin can be used as the important as precursors of polyester, and the full constituent for realizing lignocellulosic utilizes.
Description
Technical field
The method that full constituent utilizes is efficiently separated and realized the present invention relates to a kind of lignocellulosic, it is specifically wooden
Cellulose pre-processes in a solvent, realizes the separation of lignin and solid cellulose substance, and by solid cellulose catalyzed conversion
For the method for ethylene glycol.
Background technique
Lignocellulosic is most important biomass resource, has the advantages that from a wealth of sources, rich reserves, thus it is efficiently
Utilize the common concern for causing people.However hemicellulose, cellulose, lignin and a small amount of impurity are incorporated in lignocellulosic
Together, fine and close protective layer is formed, lignocellulosic is made to be difficult to catalyzed conversion utilization.Conventional pretreatment is removed wooden using alkali
Element is neutralized in subsequent process using acid, achievees the purpose that precipitate lignin.This process consumes a large amount of soda acids, and generates salt, has
The disagreeableness feature of environment.
On the other hand, the small molecular alcohols such as ethylene glycol are important energy liquid fuel, are also very important polyester synthesis
Raw material, for example, being used for polyethylene terephthalate (PET), polyethylene naphthalate (PEN) is also used as antifreeze
Agent, lubricant, plasticizer, surfactant etc. are widely used Organic Chemicals.
Ethylene glycol is prepared using the biomass with reproducibility, it is possible to reduce dependence of the mankind to fossil energy substance,
It is advantageously implemented environmental-friendly and sustainable economic development.Cellulose substances, including cellulose, hemicellulose, crops straw
The C such as stalk, corncob, rice straw, straw, Chinese silvergrass, pine, white birch wood, poplarn(H2O)mCompound is deposited extensively in nature
?.With agrotechnical development, yield is growing.Development prepares small point of ethylene glycol, propylene glycol etc. with carbohydrate
Sub- alcohol can not only reduce the dependence to petroleum resources to a certain extent, meanwhile, help to realize deep processing of farm products system height
Added value chemicals.
Currently, preparing ethylene glycol (document 1:Direct by catalytic hydroconversion cellulose under hydrothermal condition
catalytic conversion of cellulose into ethylene glycol using nickel-promoted
tungsten carbide catalysts,Angew.Chem.Int.Ed.2008,47,8510-8513；Document 2:
Transition metal-tungsten bimetallic catalysts for the conversion of
Cellulose into ethylene glycol, ChemSusChem 2010,3,63-66；101735014 A of document 3:CN,
A kind of method of carbohydrate preparing ethylene glycol；102190562 A of document 4:CN, a kind of side of carbohydrate preparing ethylene glycol
Method).This method carries out catalyzed conversion to cellulose with the mixed catalyst that tungsten-based catalyst and hydrogenation catalyst form, to obtain
Obtain the ethylene glycol of 60-75%.Similarly, the dual-component catalyst constituted using oxidation state tungsten and hydrogenation metal, in hydro-thermal plus hydrogen
Under conditions of also can be realized cellulose, starch etc. and prepare ethylene glycol, a kind of propylene glycol (document 5: containing sugar compounds are highly selective
The method WO2011113281A of preparing ethanediol from polyhydroxy compounds).
During these selectivity of ethylene glycol preferably, yield it is higher, but the raw material reacted is cellulose, there are still from
The soda acid process extracted in lignocellulosic, the environment friendly of overall process are poor.When using stalk for raw material, ethylene glycol
Yield be decreased obviously, even if being still below 40% (document 6:Catalytic hydrogenation of after oxygenation pretreatment
corn stalk to ethylene glycol and 1,2-propylene glycol."Industrial&
Engineering Chemistry Research 50,11(2011):6601-6608).Therefore cheap and environment is urgently developed
Friendly lignocellulosic separation method, realizes efficiently separating for lignocellulosic, and makes that treated cellulose matter mass-energy is high
Effect is converted into ethylene glycol.
Method provided by the invention, by solvent pre-treatment, isolates lignin and fiber using lignocellulosic as raw material
Plain substance, and cellulose substances are catalytically conveted to ethylene glycol.The method is not only easy to operate, low in cost, and realizes
The full constituent of lignocellulosic utilizes, and improves the catalytic conversion efficiency of cellulosic material and two in lignocellulosic significantly
The space-time yield of first alcohol.
Summary of the invention
The method that full constituent utilizes is efficiently separated and realized the purpose of the present invention is to provide a kind of lignocellulosic, is passed through
Pretreatment realizes that lignin and cellulose efficiently separate, obtained cellulose can Efficient Conversion be ethylene glycol, relatively conventional separation
Process the method lignin purity is high, impurity content are few, dihydric alcohol space-time yield is high, and by-product is few, is easier to industrialized production.
To achieve the above object, the technical scheme adopted by the invention is as follows:
Using natural wooden fiber's element as raw material, one of formic acid, acetic acid, propionic acid, ethanedioic acid, maleic acid or two kinds or more
For solvent, hydrogen peroxide or/and ozone are added, carries out the pretreatment of lignocellulosic at a certain temperature；It was carried out after pretreatment
Filter, obtains filtrate and solid insoluble cellulose, and the latter prepares polyalcohol for catalyzed conversion；Filtrate is distilled to recover solvent, together
When obtain remaining solid component lignin；
Solid cellulose substance catalyzed conversion carries out in water in enclosed high pressure reaction kettle, and used catalyst is multiple
Close catalyst, including catalyst A and catalyst B, catalyst A active constituent be the 8th, 9, the transition metal iron of 10 races, cobalt,
One of nickel, ruthenium, rhodium, palladium, iridium, platinum or two kinds or more, catalyst B be wolframic acid, ammonium metatungstate, tungsten oxide, in tungsten bronze
It is one or more kinds of；It is stirred to react in reaction kettle；Fill hydrogen before reacting in reaction kettle, reaction temperature >=120 DEG C, when reaction
Between no less than 5 minutes.
Lignocellulosic refers to the biomass containing lignin, cellulose and hemicellulose, including agricultural crop straw, corn
Core, rice straw, straw, Chinese silvergrass, fortune windmillpalm sheath-fibre, pine, white birch wood, one of poplar or two kinds or more.
Lignocellulosic is less than 5cm by pulverized particles partial size, and water content is lower than 20%, and water solubles content is lower than 10%,
The content of material that can dissolve at room temperature in water is lower than 10%.
Lignocellulosic and solvent quality ratio are between 10:1 and 1:10；Solvent is formic acid, acetic acid, propionic acid, ethanedioic acid
One of or two kinds or more；Between 0.001% to the 5% of the total lignocellulosic of the quality Zhan of hydrogen peroxide and/or ozone；Ozone
Pre-processing lower pressure is 0.2-1MPa, and for pretreated temperature between 20-100 DEG C, pretreatment time is 0.2-5 hours.
Contain lignin, a small amount of low molecular sugar and solvent in pretreated filtrate；Solvent is recycled by distillation, molten
Agent loss late is lower than 5%；Remaining solid adds water washing after distillation, the remaining solid substance that is obtained by filtration is lignin, is dissolved in water
In low molecular sugar can be used for catalytic cracking polyalcohol together with cellulose.
Pretreated solid cellulose substance is rich cellulose-containing reaction substrate, and content of cellulose is greater than 80%, contains
There are a small amount of hemicellulose and lignin.
Solid cellulose substance prepares glycol reaction, reaction Yu Shuizhong in enclosed high pressure reaction kettle for catalyzed conversion
Carry out, used catalyst be composite catalyst, including catalyst A and catalyst B, catalyst A active constituent be the 8th,
9, one of transition metal iron, cobalt, nickel, ruthenium, rhodium, palladium, iridium, platinum of 10 races or two kinds or more, carrier are active carbon, oxidation
Aluminium, silica, silicon carbide, zirconium oxide, zinc oxide, titanium dioxide are one or two or more kinds of；Catalyst B be wolframic acid, ammonium metatungstate,
One or more of tungsten oxide, tungsten bronze；It is stirred to react in reaction kettle；Hydrogen is filled in reaction kettle before reacting, is reacted
Temperature >=120 DEG C, reaction time are no less than 5 minutes.
Catalyst A is skeleton nickel, one in ruthenium/carbon, iridium/carbon, ruthenium/titanium dioxide, nickel-ruthenium/active carbon, nickel-iridium/active carbon
Kind or two kinds or more；The nickel content of skeleton nickel is greater than 80wt%, and the content of metal of supported catalyst is between 1-10wt%；It urges
Agent B is wolframic acid, ammonium metatungstate, one or two or more kinds of in tungsten oxide；Catalyst A and catalyst B accounts for the 1- of raw material respectively
Between 20wt%；Hydrogen, pressure 1-10MPa are filled before reacting in reaction kettle, reaction temperature is reaction between 200-260 DEG C
Time was greater than 5 minutes less than 240 minutes.
The primary product of solid cellulose substance catalyzed conversion is polyalcohol, including ethylene glycol, propylene glycol, butanediol, sweet
Oil, wherein the selectivity of ethylene glycol is more than 50%, and pre-treated solid product yield is more than 90%.
Lignocellulosic can be utilized by pretreatment by full constituent, and lignocellulosic loss late is lower than 20%, and solvent can
To be recycled, loss late is lower than 5%, and product is respectively lignin and the polyalcohol based on ethylene glycol.
The present invention has the advantage that
1. with lignocellulosic (including but not limited to agricultural crop straw, corncob, rice straw, straw, Chinese silvergrass, fortune windmillpalm sheath-fibre, pine
Wood, white birch wood, poplar) it is reaction raw materials, grain not to be striven with people and strives ground, rich reserves, most of is agricultural wastes, relative to
Ethylene raw used in existing ethylene glycol industrial production, has the advantages that raw material resources are reproducible, meets sustainable
The requirement of development has great importance to waste utilization, increasing peasant income.
2. this preprocess method solvent boiling point is lower, it is easy recycling and uses, loss late is low, and separation process is simple, convenient for behaviour
Make, lignin purity is higher, and the content of cellulose of cellulosic material is high.
3. under this composite catalyst, the high conversion efficiency of cellulose family raw material, the selectivity of ethylene glycol is good, space-time yield
Height is easier to industrialized utilization.
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
Lignocellulosic pre-treatment:
It needs to wash before lignocellulosic pretreatment, is dry, crushing, by taking Chinese silvergrass as an example, detailed process is as follows:
10g Chinese silvergrass room temperature is washed with 50g, then in 80 DEG C of dryings, after with pulverizer be crushed to partial size less than 1cm.
Preprocessing process:
By after pre-treatment 10g lignocellulosic and 50g solvent be added in flask, hydrogen peroxide or/and ozone is added, it is smelly
Oxygen pressure is 0.2MPa, is pre-processed 1 hour at 20-100 DEG C.
Separation process:
After pretreatment, solution and solid cellulose substance is obtained by filtration, after cellulosic material washing (or dry) is used for afterwards
Continuous catalytic conversion reaction, filtrate rotate recycling design, obtain water solubility after revolving bottom substance washing and contain sugar substance and not water
Molten lignin.
Catalyzed conversion experiment:
By 2g cellulose substances, 0.4g composite catalyst and 50ml water are added in 100ml reaction kettle, then pass to hydrogen
Gas displacement after gas, is flushed with hydrogen gas to 5MPa, is warming up to 240 DEG C, reacts 120min three times.After reaction, it is down to room temperature.Centrifugation
Product liquid and catalyst are separated, product liquid, which uses, to be analyzed on high performance liquid chromatography calcium type ion exchange column, is detected.It produces
Ethylene glycol, propylene glycol are calculated in object yield.
Embodiment 2
The composition for the cellulosic material that Chinese silvergrass obtains under the conditions of different pretreatments, pretreatment condition is the same as 1 (table of embodiment
One).
(analysis method uses Van to the composition for the cellulosic material that one Chinese silvergrass of table obtains under the conditions of different pretreatments
Soest method)
As shown in Table 1, under the conditions of different pretreatments, the obtained composition in cellulosic material is different, is molten with formic acid
Agent, 0.1% hydrogen peroxide, the content of cellulose of 2h available 91.5% is handled at 80 DEG C.Acetic acid, propionic acid, ethanedioic acid
Delignification ability is slightly below formic acid, but is also able to achieve the removing of lignin.
Embodiment 3
Composition analysis (table two) after different cellulose family pretreatments of raw material, pretreatment condition is the same as embodiment 1.
The different lignocellulosic material pretreated composition analysis (pretreatment conditions: formic acid, 0.1% dioxygen of table two
Water, 80 DEG C, 2h)
As shown in Table 2, constituent content is different after different lignocellulose pretreatments of raw material, wherein the fiber of white birch wood
Cellulose content highest, reaches 93.7%.
Embodiment 4
Chinese silvergrass catalyzed conversion is to the result (table three) of dihydric alcohol on different composite catalyst, and reaction condition is with embodiment 1, in advance
It is formic acid under treatment conditions, 0.1% hydrogen peroxide, 80 DEG C, 2h.
Result (the mass ratio of catalyst A and B of the Chinese silvergrass catalyzed conversion to dihydric alcohol on three different composite catalyst of table
For 1:1, catalyst charge 0.4g, water 50ml, the mass concentration of substrate in water is 10wt%)
As shown in Table 3, by pretreatment after, Chinese silvergrass can Efficient Conversion be ethylene glycol, ethylene glycol yield reach 60% a left side
The right side achieves with cellulose similar reaction result when being raw material.
Embodiment 5
Catalysis reaction result (table four) of the lignocellulosic of different condition processing on Raney Ni+ tungstic acid catalyst,
For reaction condition with embodiment 1, wolframic acid and Raney Ni ratio are 1:1.
(catalyst is Raney Ni+ wolframic acid, the two to the lignocellulosic catalyzed conversion result of four different condition of table processing
Than for 1:1)
As shown in Table 4, pretreatment condition is very big to subsequent affect, formic acid and the pretreated lignocellulosic energy of hydrogen peroxide
Enough Efficient Conversions are ethylene glycol, and ethylene glycol yield is close to 60%.
Embodiment 6
Under the conditions of different pretreatments, cellulosic material catalyzed conversion obtains ethylene glycol yield and compares (table five), reaction condition
With embodiment 1.
Under the conditions of five different pretreatments of table, cellulosic material catalyzed conversion obtains ethylene glycol yield and compares
As shown in Table 5, the yield of ethylene glycol can be significantly turned up in preprocess method provided by the invention, urge similar
Under agent and raw material, the yield of ethylene glycol reaches 65%.
The used solvent boiling point of this preprocess method in the present invention is lower, is easy recycling and uses, loss late is low, separates
Journey is simple, and convenient for operation, obtained lignin purity is higher, and the content of cellulose of cellulosic material is high.It is especially compound herein
Under catalyst, the high conversion efficiency of cellulose family raw material, the selectivity of ethylene glycol is good, space-time yield is high, is easier to industrialized utilization.
Claims (10)
1. a kind of lignocellulosic efficiently separates and realizes the method that full constituent utilizes, it is characterised in that:
Using natural wooden fiber's element as raw material, hydrogen peroxide or/and ozone are added in a solvent, carries out wooden fibre at a certain temperature
Tie up the pretreatment of element；It is filtered after pretreatment, obtains filtrate and solid insoluble cellulose, the latter prepares for catalyzed conversion
Polyalcohol；Filtrate is distilled to recover solvent, while obtaining remaining solid component lignin；
Solid cellulose substance catalyzed conversion carries out in water in enclosed high pressure reaction kettle, and used catalyst is compound urges
Agent, including catalyst A and catalyst B, catalyst A active constituent be the 8th, 9, the transition metal iron of 10 races, cobalt, nickel, ruthenium,
One of rhodium, palladium, iridium, platinum or two kinds or more, catalyst B be one of wolframic acid, ammonium metatungstate, tungsten oxide, tungsten bronze or
It is two or more；It is stirred to react in reaction kettle；Fill hydrogen before reacting in reaction kettle, reaction temperature >=120 DEG C, the reaction time is many
In 5 minutes.
2. according to the method for claim 1, it is characterised in that: the lignocellulosic refers to containing lignin, cellulose
With the biomass of hemicellulose, including agricultural crop straw, corncob, rice straw, straw, Chinese silvergrass, fortune windmillpalm sheath-fibre, pine, white birch wood, poplar
One of wood or two kinds or more.
3. according to the method for claim 1, it is characterised in that: the lignocellulosic is less than by pulverized particles partial size
5cm, water content are lower than 20%, and water solubles content is lower than 10%, i.e., the content of material that can dissolve at room temperature in water is lower than 10%.
4. according to the method for claim 1, it is characterised in that: the lignocellulosic and solvent quality ratio in 10:1 and
Between 1:10；Solvent is one of formic acid, acetic acid, propionic acid, ethanedioic acid or two kinds or more；The quality of hydrogen peroxide and/or ozone
Between 0.001% to the 5% of the total lignocellulosic of Zhan；It is 0.2-1MPa that ozone, which pre-processes lower pressure, and pretreated temperature is in 20-
Between 100 DEG C, pretreatment time is 0.2-5 hours.
5. according to the method for claim 1, it is characterised in that: contain lignin, a small amount of in the pretreated filtrate
Low molecular sugar and solvent；Solvent is recycled by distillation, and solvent loss rate is lower than 5%；After distillation remaining solid add water washing,
The remaining solid substance being obtained by filtration is lignin, and low molecular sugar soluble in water can be used for catalyzed conversion with cellulose together
Polyalcohol processed.
6. according to the method for claim 1, it is characterised in that: the pretreated solid cellulose substance is rich in fibre
The reaction substrate of element is tieed up, content of cellulose is greater than 80%, contains a small amount of hemicellulose and lignin.
7. according to the method for claim 1, it is characterised in that: the carrier of catalyst A be active carbon, aluminium oxide, silica,
Silicon carbide, zirconium oxide, zinc oxide, titanium dioxide are one or two or more kinds of.
8. according to the method for claim 1 with catalyst as claimed in claim 7, it is characterised in that: the catalyst A is
It is skeleton nickel, ruthenium/carbon, iridium/carbon, ruthenium/titanium dioxide, nickel-ruthenium/active carbon, one or two or more kinds of in nickel-iridium/active carbon；Skeleton
Nickel content in Raney nickel is greater than 80wt%, and the content of metal of supported catalyst is between 1-10wt%；Catalyst B is tungsten
It is acid, ammonium metatungstate, one or two or more kinds of in tungsten oxide；Catalyst A and catalyst B is respectively between the 1-20wt% of raw material；
Hydrogen, pressure 1-10MPa are filled before reacting in reaction kettle, reaction temperature is between 200-260 DEG C, and the reaction time is greater than 5 points
Clock was less than 240 minutes.
9. according to the method for claim 1, it is characterised in that: the primary product of the solid cellulose substance catalyzed conversion
For polyalcohol, including ethylene glycol, propylene glycol, butanediol, glycerol, wherein the selectivity of ethylene glycol is more than 50%, pre-treated solid
Product yield is more than 90%.
10. according to the method for claim 1, it is characterised in that: the lignocellulosic can be by complete group by pretreatment
Divide and utilize, lignocellulosic loss late is lower than 20%, and solvent can be recycled, and loss late is lower than 5%, and product is respectively wooden
Element and the polyalcohol based on ethylene glycol.
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| CN114423728A (en) * | 2019-09-25 | 2022-04-29 | 国际壳牌研究有限公司 | Pretreatment of lignocellulosic feedstock for glycol production |
| CN114981234A (en) * | 2020-01-15 | 2022-08-30 | 芬欧汇川集团 | Production of monoethylene glycol |
| CN116103949A (en) * | 2022-12-13 | 2023-05-12 | 华东理工大学 | Method for preparing cellulose and lignin oil by non-exogenous hydrogenolysis of polylignocellulose |
| CN117298670A (en) * | 2023-09-26 | 2023-12-29 | 广州旭璟科技有限公司 | Sugar solution and lignin separation equipment and method in lignin preparation process by organic solvent method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117298670A (en) * | 2023-09-26 | 2023-12-29 | 广州旭璟科技有限公司 | Sugar solution and lignin separation equipment and method in lignin preparation process by organic solvent method |
| CN117298670B (en) * | 2023-09-26 | 2024-04-30 | 广州旭璟科技有限公司 | Sugar solution and lignin separation equipment and method in lignin preparation process by organic solvent method |
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| CN109896922B (en) | 2022-03-22 |
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