CN104277015A - Method for catalyzing hydroxyalkylation-alkylation reaction of 2-methylfuran by using ionic liquid - Google Patents
Method for catalyzing hydroxyalkylation-alkylation reaction of 2-methylfuran by using ionic liquid Download PDFInfo
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- CN104277015A CN104277015A CN201310274053.8A CN201310274053A CN104277015A CN 104277015 A CN104277015 A CN 104277015A CN 201310274053 A CN201310274053 A CN 201310274053A CN 104277015 A CN104277015 A CN 104277015A
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- C—CHEMISTRY; METALLURGY
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- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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Abstract
The invention discloses a method for catalyzing a hydroxyalkylation-alkylation reaction of 2-methylfuran by using an ionic liquid. The method is characterized in that under the effect of an acid functionalized ionic liquid catalyst, 2-methylfuran self, or 2-methylfuran and a carbonyl compound, is/are subjected to the hydroxyalkylation-alkylation reaction at 20-100 DEG C. The reaction system does not need adding any organic solvents during reaction, and shown the characteristics of a homogeneous reaction, the catalytic activity is high, and the catalyst has no corrosivity and can be recovered for reutilization, so that the cost is reduced and also separation and purification of reaction products are facilitated.
Description
Technical field
The present invention relates to a kind of method of 2-methyl furan hydroxyalkylation-alkylated reaction (being called for short HAA reaction), more particularly, relate to a kind of 2-methyl furan using acidic functionalized ionic liquid as catalyzer self or to prepare the method for 2-(furyl methyl)-5-methyl furan compounds through hydroxyalkylation-alkylated reaction with carbonyl containing compound.
Background technology
Along with the fluctuation of day by day exhausted, the price of petroleum resources standing stock and petroleum based fuels are to the aggravation effect of global warming, the route of synthesis finding the reproducible Wooden Biomass base replacement of fuel petroleum base energy and the foodstuff starch base energy is the study hotspot field of scientific circles and industry member, is also the focal issue that social sustainable development and government and the public show great attention to.Wooden Biomass is the widest, the most important renewable resources that distributes in the world, its essentially consist unit is mainly the carbohydrate such as glucose, fructose, how these abundant carbohydrate sources is converted into the huge challenge that the Chemicals of high added value and the energy are following rare-view set-up.
In flexible and abundant Wood Adhesives from Biomass technical network, methyl furan compounds is important platform chemicals also can as high-quality liquid fuel of new generation.Methyl furan compounds comprises 2-methyl furan and 2,5-dimethyl furan, is utilized in the past by as solvent or polymer materials synthon always, and not direct and fuel connects.In fact, methyl furan compounds has potential large-scale application prospect as fuel and important industrial foundation platform chemicals.Therefore, in the long term, utilizing Wooden Biomass to transform and producing methyl furan compounds to be the most important available sources of industrial liquid fuel.2-methyl furan, another name Si Er alkane, is obtained by the bio-based hydrogenation of furfural that can be mass-produced.Itself is only containing five carbon atoms, can not use as biofuel after hydrogenation dehydration, but in acid condition, 2-methyl furan has very strong activity, three molecule 2-methyl furans or two molecule 2-methyl furans and a part containing the compound generation hydroxyalkylation-alkylated reaction of carbonyl, the C obtained
12+ OXO products can obtain the Regeneratable biological diesel oil of high-quality again through shortening dehydration.Sulfuric acid and tosic acid can catalysis 2-methyl furan and lignocellulose hydroxyalkylation-alkylated reaction (ChemSusChem, 2011,1574 of aldehyde compound that derive; Angew. Chem. Int. Ed., 2011,2375; Energy Environ. Sci., 2012,6328), the product that HAA reaction product obtains after shortening dehydration again, cetane value reaches more than 70, and upper pour point is-75 DEG C, can as high-quality biological diesel oil.This work opens a road from bio-based platform chemicals synthesis high-quality fuel.But sulfuric acid and tosic acid have corrodibility, can increase facility investment, the acid remained in addition in HAA product can make follow-up hydrogenation poisoning of catalyst, and the acid that removal remains can produce a large amount of waste water.For overcoming the inherent defect of sulfuric acid or tosic acid, the HAA that the solid acids such as acidic resins, acidic molecular sieve and metal oxide are also used to catalysis 2-methyl furan and aldehyde reacts (ChemSusChem, 2012,1958).
Acidic functionalized ionic liquid is incorporated into by acidic-group in the positively charged ion of ionic liquid or negatively charged ion and the class functionalized ion liquid obtained, large quantifier elimination shows, such ionic liquid has the advantage of liquid acid and solid acid concurrently, is the acid catalyst of novel green close friend.Acidic functionalized ionic liquid obtains application in many important catalysis such as esterification, condensation, rearrangement, the formation of C-heteroatomic bond and organic reaction, according to current understanding, also not studies have reported that the hydroxyalkylation-alkylated reaction participated in as catalyst 2-methyl furan with acidic functionalized ionic liquid.
Summary of the invention
The object of the present invention is to provide a kind of is catalyzer with acidic functionalized ionic liquid, catalysis 2-methyl furan self or prepare the method for 2-(furyl methyl)-5-methyl furan compounds with carbonyl containing compound generation hydroxyalkylation-alkylated reaction.
For achieving the above object, the technical scheme that the present invention takes is:
A kind of by the method for 2-methyl furan through the compounds of 2-(furyl methyl)-5-methyl furan hydroxyalkylation-alkylated reaction preparation formula (I) Suo Shi, it is characterized in that with 2-methyl furan or 2-methyl furan and carbonyl containing compound for reactant, take acidic functionalized ionic liquid as catalyzer, control temperature of reaction 20 ~ 100 DEG C, 1 ~ 24 hour reaction times, after reaction terminates, isolate upper organic phase, obtain product shown in formula (I) through underpressure distillation.
R in formula (I)
1represent H or aliphatics or aromatic series or heteroaromatic group, R
2represent H or aliphatics or aromatic series or heteroaromatic group.
The method of acidic functionalized ionic liquid catalysis 2-methyl furan hydroxyalkylation-alkylated reaction of the present invention, when only with 2-methyl furan for reactant time, 3 times to be added in system to the deionized water of 2-methyl furan mole number.
According to reaction method of the present invention, described carbonyl containing compound is selected from the one in formaldehyde, acetaldehyde, propionic aldehyde, butyraldehyde, valeral, hexanal, enanthaldehyde, furfural, 5 methyl furfural, 5 hydroxymethyl furfural, acetone, 2 pentanone, ethyl levulinate.
The acidic functionalized ionic liquid catalyzer that can be used for the inventive method preferably from formula be qX
n+nY
q-ionic liquid, wherein X
n+represent the acidic cation with a positive charge (n=1) or several positive charge (n>1), and Y
q-represent the negatively charged ion with a negative charge (q=1) or several negative charge (q>1).
At described acidic cation X
n+in, can mention that general formula is following glyoxaline cation X1, pyridylium X2, quaternary ammonium cation X3, season phosphine positively charged ion X4, guanidine cationoid X5, sulfonium salt positively charged ion X6, pyrroles's positively charged ion X7 and morpholine positively charged ion X8 especially:
Wherein R
1-R
5represent aliphatic group, cyclic aliphatic base or aryl independently of one another, n is the integer of 0-6.
With the negatively charged ion Y of the ionic liquid of (q=1) or multiple negative charge (q>1)
q-preferably from anion hydrogen sulphate (Y=HSO
4), nitrate anion (Y=NO
3), tosic acid root negatively charged ion (Y=CH
3-C
6h
4-SO
3), trifluoromethane sulfonic acid root negatively charged ion (Y=CF
3sO
3), methylsulphonic acid root negatively charged ion (Y=CH
3sO
3), trifluoroacetic acid root negatively charged ion (Y=CF
3cOO), two (trifluoromethyl sulfonyl) imines acid radical anion (Y=(CF
3-SO
2)
2and halogen ion (Y=Cl, Br) N).
According to a particularly preferred embodiment of the present invention, described acidic functionalized ionic liquid catalyzer is selected from 3-(3-alkyl-1-imidazoles)-1-propane sulfonic acid ionic liquid and 4-(3-alkyl-1-the imidazoles)-1-butane azochlorosulfonate acid ion liquid of following formula (II):
Wherein n=3 or 4, Y is selected from negatively charged ion Y as defined above
q-, and R
1for aliphatic group, cyclic aliphatic base or aryl.
The ionic liquid of above formula (II) is preferably from following acidic functionalized ionic liquid:
4-(3-methyl isophthalic acid-imidazoles)-1-butane sulfonic acid hydrosulfate, 4-(3-methyl isophthalic acid-imidazoles)-1-butane sulfonic acid tosilate, 3-(3-methyl isophthalic acid-imidazoles)-1-propane sulfonic acid hydrosulfate, 3-(3-methyl isophthalic acid-imidazoles)-1-propane sulfonic acid tosilate, 4-(3-ethyl-1-imidazoles)-1-butane sulfonic acid hydrosulfate, 4-(3-ethyl-1-imidazoles)-1-butane sulfonic acid tosilate, 3-(3-ethyl-1-imidazoles)-1-propane sulfonic acid hydrosulfate, 3-(3-ethyl-1-imidazoles)-1-propane sulfonic acid tosilate, 4-(3-propyl group-1-imidazoles)-1-butane sulfonic acid hydrosulfate, 4-(3-propyl group-1-imidazoles)-1-butane sulfonic acid tosilate, 3-(3-propyl group-1-imidazoles)-1-propane sulfonic acid hydrosulfate, 3-(3-propyl group-1-imidazoles)-1-propane sulfonic acid tosilate, 4-(3-butyl-1-imidazoles)-1-butane sulfonic acid hydrosulfate, 4-(3-butyl-1-imidazoles)-1-butane sulfonic acid tosilate, 3-(3-butyl-1-imidazoles)-1-propane sulfonic acid hydrosulfate, 3-(3-butyl-1-imidazoles)-1-propane sulfonic acid tosilate, 4-(3-isobutyl--1-imidazoles)-1-butane sulfonic acid hydrosulfate, 4-(3-isobutyl--1-imidazoles)-1-butane sulfonic acid tosilate, 3-(3-isobutyl--1-imidazoles)-1-propane sulfonic acid hydrosulfate, 3-(3-isobutyl--1-imidazoles)-1-propane sulfonic acid tosilate, 4-(3-hexyl-1-imidazoles)-1-butane sulfonic acid hydrosulfate, 4-(3-hexyl-1-imidazoles)-1-butane sulfonic acid tosilate, 3-(3-hexyl-1-imidazoles)-1-propane sulfonic acid hydrosulfate, 3-(3-hexyl-1-imidazoles)-1-propane sulfonic acid tosilate, 4-(3-octyl group-1-imidazoles)-1-butane sulfonic acid hydrosulfate, 4-(3-octyl group-1-imidazoles)-1-butane sulfonic acid tosilate, 3-(3-octyl group-1-imidazoles)-1-propane sulfonic acid hydrosulfate, 3-(3-octyl group-1-imidazoles)-1-propane sulfonic acid tosilate, 4-(3-dodecyl-1-imidazoles)-1-butane sulfonic acid hydrosulfate, 4-(3-dodecyl-1-imidazoles)-1-butane sulfonic acid tosilate, 3-(3-dodecyl-1-imidazoles)-1-propane sulfonic acid hydrosulfate and 3-(3-dodecyl-1-imidazoles)-1-propane sulfonic acid tosilate.
According to the solution of the present invention, catalyst levels is the 0.1-6% of reaction substrate mole number.
Major advantage of the present invention uses acidic functionalized ionic liquid to be catalyzer, 2-(furyl methyl)-5-methyl furan compounds can be prepared by high-level efficiency catalysis 2-methyl furan through HAA reaction, catalyzer and product form two-phase after the completion of reaction, easy recycling use.From ecological and economic angle consideration, advantage of the present invention is also embodied in reaction raw materials and all carrys out authigenic material, and to react unique by product be water, and environmental pollution is little; Catalyzer in the product noresidue on subsequent process without impact.
Embodiment
Embodiment 1:
By 2-methyl furan (4.93 g, 0.06 mol), deionized water (3.24 g, 0.18 mol) and (4-(3-methyl isophthalic acid-imidazoles)-1-butane sulfonic acid hydrogen sulfate ion liquid (0.949 g, 3.0 mmol) mixes, in 50 DEG C of stirring reactions.After 16 hours, isolate upper organic phase, after underpressure distillation, obtain 5,5-bis-(5-methyl-2-furyl)-2 pentanone, its yield for 2-methyl furan is 70%.
Embodiment 2:
2-methyl furan (4.93 g, 0.06 mol), deionized water (3.24 g, 0.18 mol) and 3-(3-methyl isophthalic acid-imidazoles)-1-propane sulfonic acid hydrogen sulfate ion liquid (0.907 g, 3.0 mmol) are mixed, in 50 DEG C of stirring reactions.After 16 hours, isolate upper organic phase, after underpressure distillation, obtain 5,5-bis-(5-methyl-2-furyl)-2 pentanone, its yield for 2-methyl furan is 80%.
Embodiment 3:
By 2-methyl furan (5.75 g, 0.07 mol), acetaldehyde (0.88 g, 0.02 mol) and (4-(3-methyl isophthalic acid-imidazoles)-1-butane sulfonic acid hydrogen sulfate ion liquid (0.189 g, 0.60 mmol) mix, in 50 DEG C of stirring reactions.After 2 hours, isolate upper organic phase, after underpressure distillation, obtain 2,2 '-ethylidene two (5-methyl furan), its yield for acetaldehyde is 70%.
Embodiment 4:
By 2-methyl furan (5.75 g, 0.07 mol), acetaldehyde (0.88 g, 0.02 mol) and (4-(3-methyl isophthalic acid-imidazoles)-1-butane sulfonic acid tosic acid radical ion liquid (0.235g, 0.60 mmol) mixes, in 50 DEG C of stirring reactions.After 4 hours, isolate upper organic phase, after underpressure distillation, obtain 2,2 '-ethylidene two (5-methyl furan), its yield for acetaldehyde is 88%.
Embodiment 5:
By 2-methyl furan (5.75g, 0.07 mol), propionic aldehyde (1.17 g, 0.02 mol) and (4-(3-methyl isophthalic acid-imidazoles)-1-butane sulfonic acid hydrogen sulfate ion liquid (0.189 g, 0.60 mmol) mix, in 50 DEG C of stirring reactions.After 2 hours, isolate upper organic phase, after underpressure distillation, obtain 2,2 '-propylidene two (5-methyl furan), its yield for propionic aldehyde is 75%.
Embodiment 6:
By 2-methyl furan (5.75 g, 0.07 mol), propionic aldehyde (1.17 g, 0.02 mol) and (4-(3-methyl isophthalic acid-imidazoles)-1-butane sulfonic acid tosic acid radical ion liquid (0.235g, 0.60 mmol) mixes, in 50 DEG C of stirring reactions.After 6 hours, isolate upper organic phase, after underpressure distillation, obtain 2,2 '-propylidene two (5-methyl furan), its yield for propionic aldehyde is 90%.
Embodiment 7:
By 2-methyl furan (5.75 g, 0.07 mol), butyraldehyde (1.44 g, 0.02 mol) and (4-(3-butyl-1-imidazoles)-1-propane sulfonic acid tosic acid radical ion liquid (0.251g, 0.60 mmol) mixes, in 50 DEG C of stirring reactions.After 6 hours, isolate upper organic phase, after underpressure distillation, obtain 2,2 '-Ding pitches two (5-methyl furans), and its yield for butyraldehyde is 91%.
Embodiment 8:
By 2-methyl furan (5.75 g, 0.07 mol), valeral (1.72 g, 0.02 mol) and (4-(3-hexyl-1-imidazoles)-1-butane sulfonic acid tosic acid radical ion liquid (0.268g, 0.60 mmol) mixes, in 50 DEG C of stirring reactions.After 7 hours, isolate upper organic phase, after underpressure distillation, obtain 2,2 '-pentylidene two (5-methyl furan), its yield for valeral is 90%.
Embodiment 9:
By 2-methyl furan (4.93 g, 0.06 mol), furfural (1.94 g, 0.02 mol) and (4-(3-methyl isophthalic acid-imidazoles)-1-butane sulfonic acid tosic acid radical ion liquid (0.235g, 0.60 mmol) mixes, in 50 DEG C of stirring reactions.After 6 hours, isolate upper organic phase, after underpressure distillation, obtain 2-(two (5-methyl-2-furyl)) methyl-ribofuranosyl, its yield for furfural is 65%.
Embodiment 10:
By 2-methyl furan (3.28 g, 0.04 mol), 5 methyl furfural (2.52 g, 0.02 mol) and (4-(3-methyl isophthalic acid-imidazoles)-1-butane sulfonic acid tosic acid radical ion liquid (0.235g, 0.60 mmol) mixes, in 50 DEG C of stirring reactions.After 6 hours, isolate upper organic phase, after underpressure distillation, obtain 2,2 ', 2 ' '-methyne (5-methyl furan), its yield for 5 methyl furfural is 68%.
Embodiment 11:
By 2-methyl furan (8.21 g, 0.10 mol), 5 methyl furfural (2.52 g, 0.02 mol) and (4-(3-methyl isophthalic acid-imidazoles)-1-butane sulfonic acid tosic acid radical ion liquid (0.235g, 0.60 mmol) mixes, in 50 DEG C of stirring reactions.After 6 hours, isolate upper organic phase, after underpressure distillation, obtain 2,2 ', 2 ' '-methyne (5-methyl furan), its yield for 5 methyl furfural is 92%.
Embodiment 12:
By 2-methyl furan (7.39 g, 0.09 mol), 5 hydroxymethyl furfural (1.26 g, 0.01 mol) and (4-(3-methyl isophthalic acid-imidazoles)-1-butane sulfonic acid tosic acid radical ion liquid (0.117g, 0.30 mmol) mixes, in 20 DEG C of stirring reactions.After 24 hours, isolate upper organic phase, after underpressure distillation, obtain 5-(two (5-methyl-2-furyl) methyl)-2-furfuralcohol, its yield for 5 hydroxymethyl furfural is 60%.
Embodiment 13:
By 2-methyl furan (4.93 g, 0.06 mol), 5 hydroxymethyl furfural (1.26 g, 0.01 mol) and (4-(3-methyl isophthalic acid-imidazoles)-1-butane sulfonic acid tosic acid radical ion liquid (0.117g, 0.30 mmol) mixes, in 50 DEG C of stirring reactions.After 20 hours, isolate upper organic phase, after underpressure distillation, obtain 5-(two (5-methyl-2-furyl) methyl)-2-furfuralcohol, its yield for 5 hydroxymethyl furfural is 86%.
Embodiment 14:
By 2-methyl furan (4.93 g, 0.06 mol), acetone (1.39 g, 0.024 mol) and (4-(3-methyl isophthalic acid-imidazoles)-1-butane sulfonic acid tosic acid radical ion liquid (0.274g, 0.70 mmol) mixes, in 60 DEG C of stirring reactions.After 9.5 hours, isolate upper organic phase, after underpressure distillation, obtain 2,2 '-(1-methyl ethylidene two (5-methyl furan), its yield for acetone is 72%.
Embodiment 15:
By 2-methyl furan (4.93 g, 0.06 mol), ethyl levulinate (2.88 g, 0.02 mol) and (4-(3-methyl isophthalic acid-imidazoles)-1-butane sulfonic acid tosic acid radical ion liquid (0.235g, 0.60 mmol) mixes, in 60 DEG C of stirring reactions.After 12 hours, isolate upper organic phase, after underpressure distillation, obtain 4,4-bis-(5-methyl-2-furyl) Valeric acid ethylester, its yield for ethyl levulinate is 62%.
Claims (9)
1. the method for ionic liquid-catalyzed 2-methyl furan hydroxyalkylation-alkylated reaction, it is characterized in that, take acidic functionalized ionic liquid as catalyzer, with 2-methyl furan or 2-methyl furan and carbonyl containing compound for reactant, in 20 ~ 100 DEG C, in 1 ~ 24 hour reaction times, obtain 2-(furyl methyl)-5-methyl furan compounds shown in formula (I):
R in formula (I)
1represent H or aliphatics or aromatic series or heteroaromatic group, R
2represent H or aliphatics or aromatic series or heteroaromatic group.
2. method according to claim 1, is characterized in that, when described reaction only with 2-methyl furan for reactant time, reaction system will add 3 times to the deionized water of 2-methyl furan mole number.
3. method according to claim 1, it is characterized in that, described carbonyl containing compound is selected from the one in formaldehyde, acetaldehyde, propionic aldehyde, butyraldehyde, valeral, hexanal, enanthaldehyde, furfural, 5 methyl furfural, 5 hydroxymethyl furfural, acetone, 2 pentanone, ethyl levulinate.
4. method according to claim 1, is characterized in that, described ionic-liquid catalyst is acidic functionalized ionic liquid catalyzer.
5. the method according to claim 1 or 4, is characterized in that, described acidic functionalized ionic liquid is selected from formula qX
n+nY
q-ionic liquid, wherein X
n+represent the acidic cation with a positive charge (n=1) or several positive charge (n>1), and Y
q-represent the negatively charged ion with a negative charge (q=1) or several negative charge (q>1), and wherein said positively charged ion X
n+be selected from the glyoxaline cation X1 of following general formula, pyridylium X2, quaternary ammonium cation X3, season phosphine positively charged ion X4, guanidine cationoid X5, sulfonium salt positively charged ion X6, pyrroles's positively charged ion X7 and morpholine positively charged ion X8:
Wherein R
1-R
5represent aliphatic group, cyclic aliphatic base or aryl independently of one another, n is the integer of 0-6.
6. method according to claim 5, is characterized in that, the negatively charged ion Y of described acidic functionalized ionic liquid
q-be selected from anion hydrogen sulphate, nitrate anion, tosic acid root negatively charged ion, trifluoromethane sulfonic acid root negatively charged ion, methylsulphonic acid root negatively charged ion, trifluoroacetic acid root negatively charged ion, two (trifluoromethyl sulfonyl) imines acid radical anion and halogen ion.
7. the method according to aforementioned any one of claim, it is characterized in that, described acidic functionalized ionic liquid is selected from 3-(3-alkyl-1-imidazoles)-1-propane sulfonic acid ionic liquid and 4-(3-alkyl-1-the imidazoles)-1-butane azochlorosulfonate acid ion liquid of following formula (II):
Wherein n=3 or 4, Y is selected from negatively charged ion Y as defined in claim 6
q-, R
1for aliphatic group, cyclic aliphatic base or aryl.
8. method according to claim 7, is characterized in that, the ionic liquid of formula (II) is selected from following acidic functionalized ionic liquid:
4-(3-methyl isophthalic acid-imidazoles)-1-butane sulfonic acid hydrosulfate, 4-(3-methyl isophthalic acid-imidazoles)-1-butane sulfonic acid tosilate, 3-(3-methyl isophthalic acid-imidazoles)-1-propane sulfonic acid hydrosulfate, 3-(3-methyl isophthalic acid-imidazoles)-1-propane sulfonic acid tosilate, 4-(3-ethyl-1-imidazoles)-1-butane sulfonic acid hydrosulfate, 4-(3-ethyl-1-imidazoles)-1-butane sulfonic acid tosilate, 3-(3-ethyl-1-imidazoles)-1-propane sulfonic acid hydrosulfate, 3-(3-ethyl-1-imidazoles)-1-propane sulfonic acid tosilate, 4-(3-propyl group-1-imidazoles)-1-butane sulfonic acid hydrosulfate, 4-(3-propyl group-1-imidazoles)-1-butane sulfonic acid tosilate, 3-(3-propyl group-1-imidazoles)-1-propane sulfonic acid hydrosulfate, 3-(3-propyl group-1-imidazoles)-1-propane sulfonic acid tosilate, 4-(3-butyl-1-imidazoles)-1-butane sulfonic acid hydrosulfate, 4-(3-butyl-1-imidazoles)-1-butane sulfonic acid tosilate, 3-(3-butyl-1-imidazoles)-1-propane sulfonic acid hydrosulfate, 3-(3-butyl-1-imidazoles)-1-propane sulfonic acid tosilate, 4-(3-isobutyl--1-imidazoles)-1-butane sulfonic acid hydrosulfate, 4-(3-isobutyl--1-imidazoles)-1-butane sulfonic acid tosilate, 3-(3-isobutyl--1-imidazoles)-1-propane sulfonic acid hydrosulfate, 3-(3-isobutyl--1-imidazoles)-1-propane sulfonic acid tosilate, 4-(3-hexyl-1-imidazoles)-1-butane sulfonic acid hydrosulfate, 4-(3-hexyl-1-imidazoles)-1-butane sulfonic acid tosilate, 3-(3-hexyl-1-imidazoles)-1-propane sulfonic acid hydrosulfate, 3-(3-hexyl-1-imidazoles)-1-propane sulfonic acid tosilate, 4-(3-octyl group-1-imidazoles)-1-butane sulfonic acid hydrosulfate, 4-(3-octyl group-1-imidazoles)-1-butane sulfonic acid tosilate, 3-(3-octyl group-1-imidazoles)-1-propane sulfonic acid hydrosulfate, 3-(3-octyl group-1-imidazoles)-1-propane sulfonic acid tosilate, 4-(3-dodecyl-1-imidazoles)-1-butane sulfonic acid hydrosulfate, 4-(3-dodecyl-1-imidazoles)-1-butane sulfonic acid tosilate, 3-(3-dodecyl-1-imidazoles)-1-propane sulfonic acid hydrosulfate and 3-(3-dodecyl-1-imidazoles)-1-propane sulfonic acid tosilate.
9. method according to claim 1, is characterized in that, catalyst levels is the 0.1-6% of reaction substrate mole number.
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| CN108610227A (en) * | 2016-12-10 | 2018-10-02 | 中国科学院大连化学物理研究所 | A method of preparing bicyclic aromatic compounds |
| WO2023114459A3 (en) * | 2021-12-17 | 2023-07-27 | Sadula Sunitha | Neo acids and derivatives thereof |
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| CN101580503A (en) * | 2009-05-26 | 2009-11-18 | 西南大学 | Green synthesis method of furane derivative |
| CN102762695A (en) * | 2009-12-11 | 2012-10-31 | 康斯乔最高科学研究公司 | Production of liquid fuels (sylvan liquid fuels) from 2-methylfuran |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108610227A (en) * | 2016-12-10 | 2018-10-02 | 中国科学院大连化学物理研究所 | A method of preparing bicyclic aromatic compounds |
| CN108610227B (en) * | 2016-12-10 | 2021-02-09 | 中国科学院大连化学物理研究所 | Method for preparing bicyclic aromatic compound |
| WO2023114459A3 (en) * | 2021-12-17 | 2023-07-27 | Sadula Sunitha | Neo acids and derivatives thereof |
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