CN106866364A - A kind of method that 1,3- ring pentanediols are prepared by furfuryl alcohol - Google Patents
A kind of method that 1,3- ring pentanediols are prepared by furfuryl alcohol Download PDFInfo
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- CN106866364A CN106866364A CN201510923635.3A CN201510923635A CN106866364A CN 106866364 A CN106866364 A CN 106866364A CN 201510923635 A CN201510923635 A CN 201510923635A CN 106866364 A CN106866364 A CN 106866364A
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- furfuryl alcohol
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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
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
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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
- C07C29/143—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 ketones
- C07C29/145—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 ketones with hydrogen or hydrogen-containing gases
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- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
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Abstract
The present invention relates to a kind of method that 1,3- ring pentanediols are prepared by furfuryl alcohol.The method prepares 1,3- ring pentanediols and is divided into two-step reaction with furfuryl alcohol as raw material：The first step be furfuryl alcohol solution in base catalyst or without catalyst under conditions of, it is rearranged reaction prepare hydroxycyclopent ketenes, second step be hydroxycyclopent ketenes hydrogenation catalyst catalysis under with hydrogen reaction prepare 1,3- ring pentanediols.Used catalyst, raw material are cheap and easy to get in the present invention, preparation process is simple, and the hydrogenation reaction of rearrangement reaction and hydroxycyclopent ketenes to furfuryl alcohol has activity and selectivity higher.A kind of Cheap highly effective synthetic method that furfuryl alcohol synthesizes 1,3- ring pentanediols is closed by lignocellulosic based platform compound the invention provides a kind of.
Description
Technical field
The present invention relates to a kind of method that 1,3- ring pentanediols are prepared by furfuryl alcohol.Specifically include two-step reaction：First
Walk for furfuryl alcohol solution in base catalyst or without catalyst under conditions of, it is rearranged reaction prepare hydroxycyclopent alkene
Ketone, second step is that hydroxycyclopent ketenes prepares 1,3- ring pentanediols under hydrogenation catalyst catalysis with hydrogen reaction.
With currently reported preparation 1, the method for 3- ring pentanediols compares, and catalyst of the present invention is cheap and easy to get, prepares
Process is simple, the activity and selectivity of reaction is high.The invention provides one kind by lignocellulosic based platform chemical combination
Thing closes a kind of Cheap highly effective synthetic method that furfuryl alcohol synthesizes 1,3- ring pentanediols.
Background technology
The environment such as a large amount of rows of greenhouse gases for increasingly reducing and being caused by fossil energy burning of fossil resource
Problem becomes increasingly conspicuous, and the social required quantity of the energy is also continuing to increase in addition, and oil price rises steadily, and can replace
Exploitation for the new energy of fossil resource is imperative.Biomass are applied to as a kind of reproducible organic carbon source
Turn into current hot research in the production of carbon material, fuel and chemicals.
1,3- ring pentanediol is one of important industrial chemicals, is widely used in synthesizing polyester, polyurethane, agricultural chemicals
And other organic synthesis intermediates (A1 of CN 103642005 A, US 20130244170,
WO 2013138161 A1).The synthetic method of 1,3- ring pentanediols is mainly by the product ring in petrochemical industry route
Pentadiene synthesizes (J.Am.Chem.Soc., 1963,85 (14) through borane reduction, then by hydrogen peroxide oxidation：
2066).The route needs the hypertoxic borine and hydrogen peroxide of consumption metering ratio, is the conjunction of very not environmental protection
Into method.On the other hand, the raw material sources of the method are in the product of fossil energy, with non-renewable.Chaff
Alcohol be in agriculture and forestry organic waste material hemicellulose fraction by hydrolysis and dehydration obtain it is a kind of important
Platform chemicals, the industrialized production history for having had decades at present.It is raw material conjunction with furfural and its derivative
It is rarely reported in the world into 1,3- ring pentanediols.Recently, Huber et al. (J.Catal., 2015,330:19–27)
Report and 1,5-PD is prepared by one-step method hydrogenation biomass platform chemicals furfuryl alcohol, wherein by-product is a small amount of
1,3- rings pentanediol (yield is less than 7%).
Work (the Chinese patent of oil product and chemicals is prepared in the long campaigns biomass catalyzing conversion of this seminar：
Application number：201110346501.1 and ChemSusChem.2012,5,1958-1966；Bioresource
Technology.2013,134,66–72；Chem.Commun.,2013,49,5727-5729).Developing one is
The route that row biomass and its platform chemicals are efficiently utilized.This patent description by furfural selective hydrogenation product
- furfuryl alcohol prepares the preparation method of 1,3- ring pentanediols, and used catalyst is simple and easy to get, cheap；Prepare work
In skill, in addition to hydrogen, the reagent without consuming other metering ratios.Whole route environmental protection, using can be again
Raw biomass platform chemicals furfuryl alcohol has efficiently prepared 1,3- ring pentanediols.
The content of the invention
Present invention aim at a kind of method that 1,3- ring pentanediols are prepared by furfuryl alcohol of offer.
The present invention is achieved by the following technical solutions：
1,3- ring pentanediols are prepared as raw material with furfuryl alcohol and is divided into two-step reaction：
The first step be furfuryl alcohol solution in base catalyst or without catalyst under conditions of, rearranged reaction prepares hydroxyl
Cyclopentene ketone, second step is that hydroxycyclopent ketenes prepares 1,3- under hydrogenation catalyst catalysis with hydrogen reaction
Ring pentanediol.
With document (J.Catal., 2015,330:19-27) compare, this patent synthesizes 1,3- rings penta using two-step method
Glycol, synthesizes hydroxycyclopent ketenes this intermediate compound in the first step first, then carries out hydrogenation reaction,
1,3- ring pentanediols can be in high yield obtained, and is hydrogenated with using one-step method in documents, its product up to ten is several,
Wherein, the yield of 1,3- rings pentanediol is less than 7%.And the yield of 1,3- rings pentanediol can easily reach in this patent
To more than 50%, even up to more than 90%, the wound of this exactly this patent under some specific reaction conditions
New part.
During the base catalyst that wherein first step furfuryl alcohol solution prepares the reaction of hydroxycyclopent ketenes is following catalyst
One or two or more kinds mixing：
NaOH、KOH、Na2CO3、NaHCO3, ammoniacal liquor, Ca (OH)2、Mg(OH)2、CaO、MgO、
Magnalium hydrotalcite, nickel aluminum hydrotalcite, CeO2；
Wherein, the quality of addition catalyst and the ratio of reaction substrate solution quality are between 0-0.05.
Second step hydroxycyclopent ketenes hydrogenation catalyst is one or two or more kinds mixing in following catalyst：
With activated carbon (AC), mesoporous carbon (MC), silica (SiO2), aluminum oxide (Al2O3), oxidation
Cerium (CeO2), titanium oxide (TiO2) in one or two or more kinds mixture be carrier, carried metal Pt,
The load type metal catalyst of one or two or more kinds in Pd, Ru, Ir, Ni, Co, Cu, transition metal
Carbide or nitride catalyst, Raney's nickel catalyst, amorphous alloy catalyst；
Load type metal catalyst is prepared using the method for incipient impregnation：Prepare the gold of mass concentration 0.1-10%
Category precursor solution, according to metering than adding the above-mentioned medium volume impregnation of carrier, the quality of metal contains in catalyst
Amount accounts for 0.01-30%, 6-24h is dried at 80-120 DEG C after standing 2h, then use hydrogen at 200-600 DEG C
Gas reduces 1-10h, and 1%O containing volumetric concentration is passed through after temperature is reduced to room temperature2Nitrogen inerting more than 4h；
Wherein, the quality of addition catalyst and the ratio of reaction substrate solution quality are between 0.01%-20%.
The solvent that first step furfuryl alcohol solution prepares the reaction of hydroxycyclopent ketenes is in water or water and following solvents
Plant or two kinds mixed above：Methyl alcohol, ethanol, propyl alcohol, isopropanol, butanol, isobutanol, tetrahydrofuran (THF),
Dimethyl sulfoxide (DMSO) (DMSO), N,N-dimethylformamide (DMF)；
Wherein the mass concentration of furfuryl alcohol is 0.01%-99%, and preferred concentration range is 0.1%-10%.
One kind that can not be used solvent, can also use in following solvents of second step hydroxycyclopent ketenes hydrogenation reaction
Or two kinds mixed above：Water, methyl alcohol, ethanol, propyl alcohol, isopropanol, butanol, isobutanol, tetrahydrofuran (THF),
Dimethyl sulfoxide (DMSO) (DMSO), N,N-dimethylformamide (DMF)；
Wherein the mass concentration of hydroxycyclopent ketenes is 0.01%-100%, and preferred concentration range is 0.1%-10%.
First step furfuryl alcohol solution prepares the reaction of hydroxycyclopent ketenes and can be carried out in tank reactor, it is also possible to solid
Carried out in fixed bed reactor, between 50 DEG C -300 DEG C, preferable reaction temperature is at 160 DEG C -250 for its reaction temperature
Between DEG C；
During using tank reactor, the reaction time, preferred reaction time was 0.01 between 0.001h-10h
Between h-0.5h；During using fixed bed reactors, its mass space velocity is in 0.01h-1-100h-1Between；It is preferred that empty
Speed is in 10h-1-100h-1Between；
Second step hydroxycyclopent ketenes hydrogenation reaction can be carried out in tank reactor, it is also possible in fixed bed reaction
Carried out in device, between 0 DEG C -300 DEG C, preferable reaction temperature is between 15 DEG C -160 DEG C for its reaction temperature；
Between 0.1MPa-10MPa, preferably pressure is between 1MPa-5MPa for its Hydrogen Vapor Pressure；
During using tank reactor, the reaction time, preferred reaction time was in 0.1h-2 between 0.001h-10h
Between h；During using fixed bed reactors, its mass space velocity is in 0.01h-1-100h-1Between；It is preferred that air speed exists
1h-1-10h-1Between；Hydrogen is 20-1500 with the mol ratio of reaction raw materials.
The invention has the advantages that：
Method provided by the present invention synthesizes 1,3- ring pentanediols, and its raw material comes from reproducible lignocellulosic
Platform chemicals furfuryl alcohol.Its rearrangement reaction and hydrogenation reaction use common base catalyst and hydrogenation catalyst,
Simple and easy to get, catalyst cost is relatively low.Compared to furfuryl alcohol Hydrogenation 1 reported in the literature, 3- ring pentanediols are received
Rate has significantly improved.Therefore the method for this patent is a kind of side of very useful synthesis 1,3- ring pentanediols
Method.
Brief description of the drawings
Fig. 1 furfuryl alcohol rearrangement reaction product hydroxy cyclopentenones1H-NMR spectrum；
Fig. 2 furfuryl alcohol rearrangement reaction product hydroxy cyclopentenones13C-NMR spectrograms；
Fig. 3 hydroxycyclopent ketenes hydrogenation products 1,3- ring pentanediols1H-NMR spectrum；
Fig. 4 hydroxycyclopent ketenes hydrogenation products 1,3- ring pentanediols13C-NMR spectrograms；
Specific embodiment
The present invention will be illustrated with specific embodiment below, but protection scope of the present invention is not limited to
These examples.
1. the experiment (influence of catalyst, tank reactor) of hydroxycyclopent ketenes is prepared by furfuryl alcohol
In 100mL reactors, the furfuryl alcohol aqueous solution that 50mL mass concentrations are 2% is added, added a certain amount of
Base catalyst, the specific time is reacted at a certain temperature.
The rearrangement reaction activity of the different base catalysts of table 1.
Rearrangement reaction activity (continued) of the different base catalysts of table 1.
Can be seen that different base catalysts by the result of table 1 can effectively be catalyzed the generation of furfuryl alcohol rearrangement reaction,
Obtain hydroxycyclopent ketenes in high yield, the weaker CeO of its neutral and alkali2Effect is poor.Even but being not added with
Any catalyst, still can obtain the yield of 60% hydroxycyclopent ketenes under preferably reaction condition.Urge
Influence of the agent consumption to reactivity than more significant, wherein can obtain more excellent in the NaOH of 5mg or so
Yield, more than or less than the numerical value, can cause that the yield of hydroxycyclopent ketenes lowers.And the reaction time
Influence is similar with catalytic amount, there is optimal yield when 0.02h, and overlong time can lead target product
Further there is side reaction, reduce product yield；It is too short, then have part material and do not convert completely, cause to produce
Rate is relatively low.Reaction temperature equally also has optimal value, and at 240 DEG C, the yield of hydroxycyclopent ketenes reaches most
Greatly, too high or too low temperature causes yield to decline by a small margin.
2. the experiment (influence of solvent, tank reactor) of hydroxycyclopent ketenes is prepared by furfuryl alcohol
In 100mL reactors, the certain density furfuryl alcohol aqueous solution of 50mL or water and other solvents are added
Mixed solution, with NaOH as catalyst, 0.02h is reacted at 240 DEG C.
Influence of the different solvents of table 2. to rearrangement reactivity
Influence (continued) of the different solvents of table 2. to reactivity
Be can be seen that with the increase of reaction substrate furfuryl alcohol concentration, the receipts of hydroxycyclopent ketenes by the result of table 2
Rate has significant reduction, but remains at a level higher.This in actual production process, it is necessary to
Consider yield yield with energy efficiency to obtain optium concentration.Using mixed solvent to the yield of target product
Influence is little, even the ratio of mixed solvent and water can still obtain hydroxyl higher in interior floating in a big way
The yield of cyclopentenone.
3. the experiment (fixed bed reactors) of hydroxycyclopent ketenes is prepared by furfuryl alcohol
In fixed bed reactors, difference is dense in pumping into fixed bed reactors with certain speed with liquid chromatography pump
The furfuryl alcohol aqueous solution of degree, with magnalium hydrotalcite as catalyst, is reacted at different temperature.
Furfuryl alcohol rearrangement reaction activity in the fixed bed reactors of table 3.
From table 3 it can be seen that in fixed bed reactors, under identical furfuryl alcohol concentration conditions, can obtain more
The yield of hydroxycyclopent ketenes high.The air speed of fixed bed is too big or too small receipts that can cause hydroxycyclopent ketenes
Rate reduction, this is similar with the reason of reaction time influence yield in tank reactor.Temperature is to hydroxycyclopent ketenes
Generation have a large effect, the too low generation for being unfavorable for target product of temperature, 240 DEG C is optimal reaction temperature
Degree.
4. the experiment (influence of catalyst, tank reactor) of hydroxycyclopent ketenes hydrogenation
In 100mL reactors, the hydroxycyclopent ketenes solution of 50mL mass concentrations 2%, solvent are added
It is tetrahydrofuran (THF) to add the hydrogenation catalyst of 0.1g, the specific time is reacted at a certain temperature.
The hydrogenation reaction activity of the different catalysts of table 4.
Hydrogenation reaction activity (continued) of the different catalysts of table 4.
Nearly all common hydrogenation catalyst is can be seen that from the data in table 4 to add hydroxycyclopent ketenes
Hydrogen reaction has good effect, wherein, it is optimal with the activity that W metal and Ru are showed.Metal Supported
Amount and reaction time slightly have influence to the yield of 1,3- ring pentanediols, but whether apparent.Reaction temperature is relative
For influence larger, 160 DEG C be optimal reaction temperature.
5. the experiment (influence of solvent, tank reactor) of hydroxycyclopent ketenes hydrogenation
In 100mL reactors, the hydroxycyclopent ketenes solution for adding 50mL certain density, with Ru/AC
Or Raney Ni are catalyst, catalyst charge is 0.1g, and 1h is reacted at 160 DEG C.
Influence of the different solvents of table 5. to hydrogenation reaction activity
Influence (continued) of the different solvents of table 5. to hydrogenation reaction activity
Influence of the solvent to hydrogenation reaction is can be seen that from the data in table 5 very big, in aprotic solvents such as
THF, DMF, DMSO etc. can obtain 1,3- ring pentanediol yields very high.And in the systems such as water, alcohol
1,3- ring pentanediol yields are relatively low.Its mixed solvent effect falls between.Concentration of substrate is to 1,3- rings
The influence of pentanediol yield is larger, and concentration is smaller, and yield is higher.
6. the experiment (fixed bed reactors) of hydroxycyclopent ketenes hydrogenation
In fixed bed reactors, difference is dense in pumping into fixed bed reactors with certain speed with liquid chromatography pump
The hydroxycyclopent ketenes THF solution of degree, with Ru/AC as catalyst, is reacted at different temperature.
Hydrogenation reaction activity in the fixed bed reactors of table 6.
Hydrogenation reaction activity (continued) in the fixed bed reactors of table 6.
Can be seen that influence of the concentration of substrate to hydrogenation reaction is very big from the data in table 6, too high substrate is dense
Degree will cause 1,3- ring pentanediol yields substantially to lower.Air speed influences relatively small to 1,3- ring pentanediols yield.
Reaction temperature is little to the influence of 1,3- ring pentanediols yield in 160 DEG C -300 DEG C of high temperature section, when temperature is less than 100 DEG C
When, 1,3- ring pentanediol yield is significantly reduced.
From above-described embodiment as can be seen that by two-step method, preparing in high yield can be realized from furfuryl alcohol completely
1,3- ring pentanediols.And the catalyst used during being somebody's turn to do is common, cheap base catalyst and hydrogenation catalyst.
During being somebody's turn to do in addition to hydrogen, it is not required to add other extra running stores, whole process environmental protection is very high
The synthetic method of the 1,3- ring pentanediols of effect.
Claims (4)
1. the method that one kind is prepared 1,3- ring pentanediols by furfuryl alcohol, it is characterised in that：
1,3- ring pentanediols are prepared as raw material with furfuryl alcohol and is divided into two-step reaction：
The first step be furfuryl alcohol solution in base catalyst or without catalyst under conditions of, rearranged reaction prepares hydroxyl
Cyclopentene ketone, second step is that hydroxycyclopent ketenes prepares 1,3- under hydrogenation catalyst catalysis with hydrogen reaction
Ring pentanediol.
2. preparation method according to claim 1, it is characterised in that：
The base catalyst that first step furfuryl alcohol solution prepares the reaction of hydroxycyclopent ketenes is the one kind in following catalyst
Or two kinds mixed above：
NaOH、KOH、Na2CO3、NaHCO3, ammoniacal liquor, Ca (OH)2、Mg(OH)2、CaO、MgO、
Magnalium hydrotalcite, nickel aluminum hydrotalcite, CeO2；
Wherein, the quality of addition catalyst and the ratio of reaction substrate solution quality are between 0-0.05；
Second step hydroxycyclopent ketenes hydrogenation catalyst is one or two or more kinds mixing in following catalyst：
With one or two or more kinds in activated carbon, mesoporous carbon, silica, aluminum oxide, cerium oxide, titanium oxide
Mixture is carrier, one or two or more kinds kind in carried metal Pt, Pd, Ru, Ir, Ni, Co, Cu
Load type metal catalyst, transition metal carbide or nitride catalyst, Raney's nickel catalyst, amorphous state
Alloy catalyst；
Load type metal catalyst is prepared using the method for incipient impregnation：Prepare the gold of mass concentration 0.1-10%
Category precursor solution, according to metering than adding the above-mentioned medium volume impregnation of carrier, the quality of metal contains in catalyst
Amount accounts for 0.01-30%, 6-24h is dried at 80-120 DEG C after standing 2h, then use hydrogen at 200-600 DEG C
Gas reduces 1-10h, and 1%O containing volumetric concentration is passed through after temperature is reduced to room temperature2Nitrogen inerting more than 4h；
Wherein, the quality of addition catalyst and the ratio of reaction substrate solution quality are between 0.01%-20%.
3. preparation method according to claim 1, it is characterised in that：
The solvent that first step furfuryl alcohol solution prepares the reaction of hydroxycyclopent ketenes is in water or water and following solvents
Plant or two kinds mixed above：Methyl alcohol, ethanol, propyl alcohol, isopropanol, butanol, isobutanol, tetrahydrofuran, two
Methyl sulfoxide, N,N-dimethylformamide；
Wherein the mass concentration of furfuryl alcohol is 0.01%-99%, and preferred concentration range is 0.1%-10%；
Second step hydroxycyclopent ketenes hydrogenation reaction can without solvent, also can using the one kind in following solvents or
Two kinds mixed above：Water, methyl alcohol, ethanol, propyl alcohol, isopropanol, butanol, isobutanol, tetrahydrofuran, two
Methyl sulfoxide, N,N-dimethylformamide；
Wherein the mass concentration of hydroxycyclopent ketenes is 0.01%-100%, and preferred concentration range is 0.1%-10%.
4. preparation method according to claim 1, it is characterised in that：
First step furfuryl alcohol solution prepares the reaction of hydroxycyclopent ketenes and can be carried out in tank reactor, it is also possible to solid
Carried out in fixed bed reactor, between 50 DEG C -300 DEG C, preferable reaction temperature is at 160 DEG C -250 for its reaction temperature
Between DEG C；
During using tank reactor, the reaction time, preferred reaction time was 0.01 between 0.001h-10h
Between h-0.5h；During using fixed bed reactors, its mass space velocity is in 0.01h-1-100h-1Between；It is preferred that empty
Speed is in 10h-1-100h-1Between；
Second step hydroxycyclopent ketenes hydrogenation reaction can be carried out in tank reactor, it is also possible in fixed bed reaction
Carried out in device, between 0 DEG C -300 DEG C, preferable reaction temperature is between 15 DEG C -160 DEG C for its reaction temperature；
Between 0.1MPa-10MPa, preferably pressure is between 1MPa-5MPa for its Hydrogen Vapor Pressure；
During using tank reactor, the reaction time, preferred reaction time was in 0.1h-2 between 0.001h-10h
Between h；During using fixed bed reactors, its mass space velocity is in 0.01h-1-100h-1Between；It is preferred that air speed exists
1h-1-10h-1Between；Hydrogen is 20-1500 with the mol ratio of reaction raw materials.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109608304A (en) * | 2019-01-24 | 2019-04-12 | 嘉兴学院 | A kind of method that furfural hydrogenation directly produces 1,2- pentanediol |
| CN111253231A (en) * | 2020-02-03 | 2020-06-09 | 厦门大学 | Preparation method of 4-cyclopentene-1, 3-dione |
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| CN109608304B (en) * | 2019-01-24 | 2021-08-06 | 嘉兴学院 | Method for directly producing 1, 2-pentanediol by furfural hydrogenation |
| CN109608304A (en) * | 2019-01-24 | 2019-04-12 | 嘉兴学院 | A kind of method that furfural hydrogenation directly produces 1,2- pentanediol |
| CN114302904A (en) * | 2019-08-30 | 2022-04-08 | 可隆工业株式会社 | Polymer compound containing cyclic monomer derived from biomass and method for producing same |
| EP4006078A4 (en) * | 2019-08-30 | 2023-09-06 | Kolon Industries, Inc. | Polymer compound comprising biomass-derived cyclic monomer and preparation method therefor |
| WO2021040474A1 (en) * | 2019-08-30 | 2021-03-04 | 코오롱인더스트리 주식회사 | Polymer compound comprising biomass-derived cyclic monomer and preparation method therefor |
| KR20210026396A (en) * | 2019-08-30 | 2021-03-10 | 코오롱인더스트리 주식회사 | Polymer comprising cyclic monomer from biomass and method for preparing comprising the same |
| US12043700B2 (en) | 2019-08-30 | 2024-07-23 | Kolon Industries, Inc. | Polymer compound comprising biomass-derived cyclic monomer and preparation method therefor |
| KR102478598B1 (en) | 2019-08-30 | 2022-12-15 | 코오롱인더스트리 주식회사 | Polymer comprising cyclic monomer from biomass and method for preparing comprising the same |
| WO2021086089A1 (en) * | 2019-10-29 | 2021-05-06 | 코오롱인더스트리 주식회사 | Method for preparing 1,3-cyclopentanediol |
| KR20210051070A (en) * | 2019-10-29 | 2021-05-10 | 코오롱인더스트리 주식회사 | Method for preparing 1,3-cyclopentanediol |
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| KR102559646B1 (en) * | 2019-10-29 | 2023-07-24 | 코오롱인더스트리 주식회사 | Method for preparing 1,3-cyclopentanediol |
| CN113045392A (en) * | 2019-12-27 | 2021-06-29 | 中国科学院大连化学物理研究所 | Application of hierarchical pore molecular sieve in preparation of cyclopentadiene and JP-10 aviation fuel |
| CN111253231B (en) * | 2020-02-03 | 2021-08-03 | 厦门大学 | Preparation method of 4-cyclopentene-1, 3-dione |
| CN111253231A (en) * | 2020-02-03 | 2020-06-09 | 厦门大学 | Preparation method of 4-cyclopentene-1, 3-dione |
| CN113968771A (en) * | 2021-11-17 | 2022-01-25 | 大连理工大学 | Method for preparing o-xylene glycol by selective hydrogenolysis of phthalide |
| CN113968771B (en) * | 2021-11-17 | 2022-07-19 | 大连理工大学 | Method for preparing o-xylene glycol by selective hydrogenolysis of phthalide |
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