CN106866388A - A kind of method of ionic liquid-catalyzed synthesis diethoxymethane - Google Patents
A kind of method of ionic liquid-catalyzed synthesis diethoxymethane Download PDFInfo
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- CN106866388A CN106866388A CN201710019928.8A CN201710019928A CN106866388A CN 106866388 A CN106866388 A CN 106866388A CN 201710019928 A CN201710019928 A CN 201710019928A CN 106866388 A CN106866388 A CN 106866388A
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- cationoid
- formaldehyde
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- ionic liquid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
- C07C41/56—Preparation of compounds having groups by reactions producing groups by condensation of aldehydes, paraformaldehyde, or ketones
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Abstract
The invention discloses a kind of method of ionic liquid-catalyzed synthesis diethoxymethane, the method is with acidic ion liquid as catalyst, with formaldehyde and ethanol as reactant, under nitrogen atmosphere reaction temperature be 80 ~ 160 DEG C, reaction pressure be 0.5 ~ 5.0Mpa react 0.5 ~ 6 h;The cationic moiety of ionic liquid is selected from alkyl imidazolium cation, pyridine cationoid, quaternary ammonium cationoid, season phosphine cation or heterocycle cationoid.The method reaction raw materials can derive from Coal Chemical Industry and biomass, cheap and easy to get;Catalyst activity is high, reusable, and corrosivity is low, to equipment without particular/special requirement;Reaction condition is gentle, and reaction and separation process are simple.
Description
Technical field
The present invention relates to one kind with ionic liquid as catalyst, formaldehyde synthesizes diethoxymethane with ethanol acetalation
Method.
Background technology
Diethoxymethane is also known as ethylal(DEM), boiling point is 88 DEG C, and the solubility in water is 4.4%(20
℃), the affinity to water is low, and binary azeotrope can be respectively formed with water, ethanol;With preferable stability, hydroxide,
Stabilization under the highly basic such as sodium hydride, RMgBr and solutions of weak acidity, and be difficult to form peroxide;Viscosity is small, and brushing performance is good.
DEM is increasingly being used for the fields such as organic synthesis, extraction, dilution, recrystallization as a kind of more economical solvent, and most probably
Substitute some common solvents such as tetrahydrofuran(THF), ethyl acetate, dichloroethanes, toluene, oxirane, methyl tertbutyl
Ether etc., realizes commercial Application.Additionally, DEM can be additionally used in synthetic resin, spices, paint, the solvent of neoprene adhesive and
Coating additive.DEM is mainly used as ethoxymethyl reagent, carbonylation substrate, formaldehyde equivalent etc. as reaction reagent.
The preparation method of DEM mainly has dichloromethane method, dimethyl sulfoxide method, Calcium Chloride Method, acetalation method etc., wherein dichloro
Methane method requirement is operated in anhydrous conditions, and product yield is low;Dimethyl sulfoxide method generates SO2, it is unfavorable for large-scale production;Chlorination
The calcium method reaction time is long, and post processing is complicated.Acetalation method raw material is cheap and easy to get, process is simple, is that current researcher pays close attention to the most
Preparation method.Acetalation method is that DME is synthesized in the presence of acidic catalyst using ethanol and formaldehyde, and that has reported urges
Agent system is mainly liquid acid and solid acid.Liquid acid catalyst such as sulfuric acid(CN 102180777A, C), hydrochloric acid(CN
1272298C)Deng Bronsted acid, Gu Zhenggui et al., using reactive distillation mode, reacts, diethyl with hydrochloric acid as catalyst at 80 DEG C
The yield highest of epoxide methane can reach 76%.But, there is seriously corroded, material requirement height, environment to equipment in liquid acid
The defect such as pollute, be difficult to reuse.The immobilized sulfuric acid catalyst of solid acid catalyst such as activated carbon(CN 102795976B), tree
Fat, molecular sieve etc..Solid acid overcomes liquid acid and separates the defects such as difficulty, seriously corroded, but generally existing target product yield
It is low, the easy carbon distribution of catalyst surface and inactivate.Acidic ion liquid has that sour density is high, acid strength is evenly distributed, corrosivity is low, easy
The advantages of reclaiming and reuse, is widely used in some important organic synthesis.Therefore, develop a kind of high living
Property, low-corrosiveness, easily reclaim, environment-friendly catalyst system be synthesize DEM key.
The content of the invention
It is an object of the invention to provide a kind of method of ionic liquid-catalyzed synthesis diethoxymethane.
Chemical equation of the invention is as follows, and wherein IL is ionic liquid.
It is a kind of it is ionic liquid-catalyzed synthesis diethoxymethane method, it is characterised in that with acidic ion liquid for be catalyzed
Agent, with formaldehyde and ethanol as reactant, under nitrogen atmosphere reaction temperature be 80 ~ 160 DEG C, reaction pressure be 0.5 ~ 5.0Mpa it is anti-
Answer 0.5 ~ 6 h;The cationic moiety of the ionic liquid be selected from alkyl imidazolium cation, pyridine cationoid, quaternary ammonium cationoid,
Season phosphine cation or heterocycle cationoid;
The alkyl imidazolium cation is selected from the one kind in following structural formula:
,
Wherein:M, n are the integer of 1-10, and R is H, alkyl or aryl, and X is SO3H、SO3CH3Or COOH;
The pyridine cationoid is selected from the one kind in following structural formula:
,
Wherein:M is the integer of 1-10, and n is the integer of 0-10, and R is H, alkyl or aryl, and X is SO3H、SO3CH3Or COOH;
The quaternary ammonium cationoid is selected from the one kind in following structural formula:
,
Wherein:M, n are the integer of 1-10, R, R1、R2It is alkyl or aryl, X is SO3H、SO3CH3Or COOH;
The season phosphine cation is selected from the one kind in following structural formula:
,
Wherein:M, n are the integer of 1-10, R, R1、R2It is alkyl or aryl, X is SO3H、SO3CH3Or COOH;
The heterocycle cationoid is selected from the one kind in following structural formula:
,
Wherein:M, n are the integer of 1-10, and R is H, alkyl or aryl, and X is SO3H、SO3CH3Or COOH.
The anionicsite of the ionic liquid be selected from p-methyl benzenesulfonic acid root, trifluoromethane sulfonic acid root, pyrovinic acid root,
Bisulfate ion, trifluoroacetic acid root or phosphate radical.
The donor of the formaldehyde is formalin, metaformaldehyde or paraformaldehyde.
The concentration of the formalin is 30wt.% ~ 90wt.%.
The ethanol is 1 ~ 6 with the mol ratio of formaldehyde:1, the consumption of the ionic liquid is 1~10wt. of total amount of feeding
%。
The ethanol is 2 ~ 4 with the mol ratio of formaldehyde:1, the consumption of the ionic liquid for total amount of feeding 2~
8wt.%。
The reaction temperature is 100~150 DEG C, and reaction pressure is 2.0~4.0 Mpa;Reaction time is 1 ~ 2h.
The present invention has advantages below:
1)Catalyst amount is few, and catalysis activity is high, and the conversion ratio of formaldehyde can reach more than 80%, and selectivity of product is more than
95%。
2)Catalytic erosion is low, to equipment without particular/special requirement.
3)Catalyst is recyclable and reuses, and reduce further the cost of catalyst.
4)It is cheap and easy to get to reaction raw materials without particular/special requirement.
5)Reaction condition is gentle, and course of reaction is simple, controllability is strong.
Specific embodiment
Catalyst is expressed as follows:
Embodiment 1:
In 100mL autoclaves, formalin, the 0.73g/2.3mmol of 4.3g/0.1mol (70%) are sequentially added
Ionic liquid a and 13.6g/0.3mol ethanol, closed reactor, with the N of 1.0MPa2Air in displacement reaction system, fills N2
To 1.0MPa.Stirring, is warming up to 120 in 30minoC, 1h is reacted under conditions of 2.0 MPa.Reaction terminates, and is cooled to room
Temperature, release.GC is analyzed, inner mark method ration.The conversion ratio of formaldehyde is 81.3%, and the selectivity of diethoxymethane is 95.5%.
Embodiment 2:
With embodiment 1, using 0.85g/2.3mmol catalyst b, the conversion ratio of formaldehyde is 82.1%, the choosing of diethoxymethane
Selecting property is 95.8%.
Embodiment 3:
With embodiment 1, using 0.72g/2.3mmol catalyst c, 60% formalin is reaction raw materials, and inventory is
5.0g/0.1mol.The conversion ratio of formaldehyde is 78.2%, and the selectivity of diethoxymethane is 96.1%.
Embodiment 4:
With embodiment 1, using 0.84g/2.3mmol catalyst d, 55% formalin is reaction raw materials, and inventory is
5.5g/0.1mol.The conversion ratio of formaldehyde is 76.3%, and the selectivity of diethoxymethane is 96.2%.
Embodiment 5:
With embodiment 1, using 0.77g/2.3mmol catalyst e, 75% formalin is reaction raw materials, and inventory is
4.0g/0.1mol.The conversion ratio of formaldehyde is 83.1%, and the selectivity of diethoxymethane is 94.1%.
Embodiment 6:
With embodiment 1, using 1.14 g/2.3mmol catalyst f, the conversion ratio of formaldehyde is 76.2%, the choosing of diethoxymethane
Selecting property is 96.4%.
Embodiment 7:
With embodiment 1, using 0.55 g/2.3mmol catalyst g, the conversion ratio of formaldehyde is 70.1%, the choosing of diethoxymethane
Selecting property is 97.4%.
Embodiment 8:
With embodiment 1, using 0.69 g/2.3mmol catalyst h, the conversion ratio of formaldehyde is 80.5%, the choosing of diethoxymethane
Selecting property is 95.4%.
Embodiment 9:
With embodiment 1, using 1.52 g/2.3mmol catalyst i, the conversion ratio of formaldehyde is 82.8%, the choosing of diethoxymethane
Selecting property is 96.5%.
Embodiment 10:
With embodiment 1, using 1.44 g/2.3mmol catalyst j, the conversion ratio of formaldehyde is 82.2%, the choosing of diethoxymethane
Selecting property is 93.5%.
Embodiment 11:
With embodiment 1, ethanol inventory is 18.4g/0.4mol, and the conversion ratio of formaldehyde is 81.4%, the choosing of diethoxymethane
Selecting property is 95.8%.
Embodiment 12:
With embodiment 1, ethanol inventory is 9.2g/0.2mol, and the conversion ratio of formaldehyde is 55.3%, the selection of diethoxymethane
Property is 95.1%.
Embodiment 13:
With embodiment 1, reaction temperature is 100oC, the conversion ratio of formaldehyde is 75.0%, and the selectivity of diethoxymethane is
95.5%。
Embodiment 14:
With embodiment 1, reaction temperature is 140oC, the conversion ratio of formaldehyde is 83.0%, and the selectivity of diethoxymethane is
95.0%。
Embodiment 15:
With embodiment 1, reaction pressure is 3.0MPa, and the conversion ratio of formaldehyde is 81.4%, and the selectivity of diethoxymethane is
95.3%。
Embodiment 16:
With embodiment 1, the reaction time is 2h, and the conversion ratio of formaldehyde is 80.8%, and the selectivity of diethoxymethane is 95.4%.
Embodiment 17:
With embodiment 1, reused after catalyst vacuum dehydration.The conversion ratio of formaldehyde is 81.0%, the choosing of diethoxymethane
Selecting property is 95.0%.
Embodiment 18:
With embodiment 15, the conversion ratio of formaldehyde is 81.2%, and the selectivity of diethoxymethane is 95.3%.
Claims (7)
1. it is a kind of it is ionic liquid-catalyzed synthesis diethoxymethane method, it is characterised in that with acidic ion liquid for be catalyzed
Agent, with formaldehyde and ethanol as reactant, under nitrogen atmosphere reaction temperature be 80 ~ 160 DEG C, reaction pressure be 0.5 ~ 5.0Mpa it is anti-
Answer 0.5 ~ 6 h;The cationic moiety of the ionic liquid be selected from alkyl imidazolium cation, pyridine cationoid, quaternary ammonium cationoid,
Season phosphine cation or heterocycle cationoid;
The alkyl imidazolium cation is selected from the one kind in following structural formula:
,
Wherein:M, n are the integer of 1-10, and R is H, alkyl or aryl, and X is SO3H、SO3CH3Or COOH;
The pyridine cationoid is selected from the one kind in following structural formula:
,
Wherein:M is the integer of 1-10, and n is the integer of 0-10, and R is H, alkyl or aryl, and X is SO3H、SO3CH3Or COOH;
The quaternary ammonium cationoid is selected from the one kind in following structural formula:
,
Wherein:M, n are the integer of 1-10, R, R1、R2It is alkyl or aryl, X is SO3H、SO3CH3Or COOH;
The season phosphine cation is selected from the one kind in following structural formula:
,
Wherein:M, n are the integer of 1-10, R, R1、R2It is alkyl or aryl, X is SO3H、SO3CH3Or COOH;
The heterocycle cationoid is selected from the one kind in following structural formula:
,
Wherein:M, n are the integer of 1-10, and R is H, alkyl or aryl, and X is SO3H、SO3CH3Or COOH.
2. the method for claim 1, it is characterised in that the anionicsite of the ionic liquid is selected to methylbenzene sulphur
Acid group, trifluoromethane sulfonic acid root, pyrovinic acid root, bisulfate ion, trifluoroacetic acid root or phosphate radical.
3. the method for claim 1, it is characterised in that the donor of the formaldehyde is formalin, metaformaldehyde or many
Polyformaldehyde.
4. method as claimed in claim 3, it is characterised in that the concentration of the formalin is 30wt.% ~ 90wt.%.
5. the method for claim 1, it is characterised in that the ethanol is 1 ~ 6 with the mol ratio of formaldehyde:1, the ion
The consumption of liquid is 1~10wt. % of total amount of feeding.
6. method as claimed in claim 5, it is characterised in that the ethanol is 2 ~ 4 with the mol ratio of formaldehyde:1, the ion
The consumption of liquid is 2~8wt.% of total amount of feeding.
7. the method for claim 1, it is characterised in that the reaction temperature is 100~150 DEG C, and reaction pressure is 2.0
~4.0 Mpa;Reaction time is 1 ~ 2h.
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Cited By (3)
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CN114437018A (en) * | 2020-11-05 | 2022-05-06 | 中国科学院化学研究所 | Method for preparing 1, 4-dioxane compound by dehydrating and cyclizing diol compound |
CN114920628A (en) * | 2022-03-30 | 2022-08-19 | 江西浩普海诚新材料有限公司 | Continuous method for preparing dialkoxy methane compound by reactor series dehydration membrane |
CN114920628B (en) * | 2022-03-30 | 2024-09-24 | 江西浩普海诚新材料有限公司 | Continuous method for preparing dialkoxy methane compound by reactor serial dehydration film |
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CN114920628A (en) * | 2022-03-30 | 2022-08-19 | 江西浩普海诚新材料有限公司 | Continuous method for preparing dialkoxy methane compound by reactor series dehydration membrane |
CN114920628B (en) * | 2022-03-30 | 2024-09-24 | 江西浩普海诚新材料有限公司 | Continuous method for preparing dialkoxy methane compound by reactor serial dehydration film |
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