CN109503541A - A kind of preparation method of 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane - Google Patents
A kind of preparation method of 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane Download PDFInfo
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- CN109503541A CN109503541A CN201811597254.0A CN201811597254A CN109503541A CN 109503541 A CN109503541 A CN 109503541A CN 201811597254 A CN201811597254 A CN 201811597254A CN 109503541 A CN109503541 A CN 109503541A
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- methyl
- methylol
- isobutyl group
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- dioxolane
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/20—Free hydroxyl or mercaptan
Abstract
The invention discloses a kind of 2- methyl -2- isobutyl group -4- methylols -1, the preparation method of 3- dioxolanes, using hexone (MIBK) and glycerol as raw material, it is characterized by: a serialization condensation reaction is fixed using solid acid catalyst, 90-115 DEG C of reaction temperature, the water for reacting generation is removed through azeotropic distillation；The later reaction product rectifying of water will be removed, removes and recycles excessive unreacted MIBK, obtain 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane.The method of the present invention realizes 2- methyl -2- isobutyl group -4- methylol -1; the continuous production of 3- dioxolanes; mode of operation is simple; significantly improve 2- methyl -2- isobutyl group -4- methylol -1; the production efficiency of 3- dioxolanes; its production cost is reduced, and can be reduced solid pollutant and discharge of wastewater, there is splendid large-scale industrial application value.
Description
Technical field
The present invention relates to a kind of preparation method of 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane,
Especially it is particularly to a kind of continuous condensating reaction preparation 2- methyl -2- isobutyl group -4- methylol -1,3- dioxy penta
The method of ring.
Background technique
2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane, alias 4- methylol -2- isobutyl
Base -2- methyl-1,3- dioxolanes；[2- methyl -2- (2- methyl-propyl) -1,3- dioxolanes -4- base] methanol (CAS:
It 5660-53-7), is a kind of slow-evaporating solvent of novel special construction, the function with multiple elements chemical function in molecular structure
Group has special dissolubility, alternative alcohol ethers solvent, in fields such as coating, ink, leather processing as solvent, hydrotropy
Agent, coalescing agent etc..
Usual 1,3- dioxolanes can be obtained by paraformaldehyde and glycol reaction.Paraformaldehyde is reacted with ethylene glycol investment
In kettle, make catalyst with strong-acid ion exchange resin, in 90-110 DEG C of progress synthesis under normal pressure；Reaction product distillates 70-
74 DEG C of azeotropic mixtures, through sodium chloride saltout and anhydrous calcium chloride dehydration after, then carry out distilation, cut 71-74 DEG C of fraction, with point
Son sieve takes off moisture to 200ppm to get product.Another method is to keep paraformaldehyde and ethylene glycol anti-in the presence of the concentrated sulfuric acid
It answers, saltouts through sodium chloride；Solid caustic soda is dry, and rectifying obtains product.
In the prior art there is not yet preparing 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane
The public reporting of method.Optional method first is that preparing 2- using hexone (MIBK) and glycerol condensation reaction
Methyl -2- isobutyl group -4- methylol -1,3-dioxolane, reaction equation are as follows:
The synthesis of 1,3-dioxolane and its derivative, the method generallyd use are intermittent condensation dehydration technique,
Catalyst used in reaction process is inorganic acid or organic acid, and inorganic acid is main are as follows: phosphoric acid, hydrochloric acid, the concentrated sulfuric acid and chlorosulfonic acid；
Organic acid is main are as follows: oxalic acid, citric acid, methanesulfonic acid and p-methyl benzenesulfonic acid take homogeneous reaction.But with hexone
It (MIBK) is that Material synthesis 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane method has no with glycerol
Disclosed related technology reports.The above method the problem is that, need to remove by alkali neutralization after reaction used in urge
Agent, and this method side reaction is more, corrosivity is strong, complex technical process, production efficiency are low, generates a large amount of solid waste
With contaminated wastewater environment.
Summary of the invention
It is an object of that present invention to provide a kind of 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane
Preparation method, this method are able to achieve the continuous metaplasia of 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane
It produces, improves 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane production efficiency, overcome batch production
Complex technical process present in technique, production efficiency are low, generate the disadvantages of a large amount of solid waste and waste water, reduce it
Production cost.
The technical solution adopted in the present invention is as follows:
A kind of preparation method of 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane, feature exist
In: using hexone (MIBK) and glycerol as raw material, serialization is fixed using solid acid catalyst and is condensed instead
It answers, 85-115 DEG C of reaction temperature, the water for reacting generation is removed through azeotropic distillation；The later reaction product rectifying of water will be removed, is taken off
Excessive unreacted MIBK is removed and recycled, 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane is obtained.
The solid acid catalyst is a kind of composite enhanced macroporous polystyrene sulfonic acid type highly acidic cation exchange
Resin.The cation exchange resin polymer, it is usual to can be used polystyrene sulfonic acid type storng-acid cation exchange resin
Synthetic method, i.e., by styrene and divinylbenzene monomers polymerization after sulfonation be made.It is poly- for the cation exchange resin
The molal quantity for closing divinylbenzene in monomer accounts for 20~35%, and weight is added and accounts for polymerized monomer total amount 1~3% (wt/wt)
The pore-foaming agent of micron order graphite whisker and polymerized monomer total amount 40~70% (wt/wt).The pore-foaming agent includes toluene, diformazan
Benzene, gasoline, normal heptane, isooctane, isooctanol or 2- ethyl butanol etc. or their mixture.Composite pore-forming is added, it can
The ion exchange resin made has macropore, mesoporous, the substantially equally distributed aperture of aperture, to greatly improve catalyst
Intensity, thermal stability and the specific surface area of skeleton.
The fixed bed continuous reaction is recommended to carry out continuous condensating reaction using two-part fixed bed, i.e., at two
It is filled in the fixed bed reactors of the solid acid catalyst and is carried out continuously two sections of condensation reactions.It is heated in view of condensation reaction
The reversible reaction of mechanical balance limitation carries out to be conducive to condensation reaction to desired direction, and first segment condensation reaction products are de-
After the water generated except reaction, then second segment condensation reaction is carried out, to obtain higher conversion ratio.Specific practice is, first by raw material
MIBK and glycerol are mixed by certain mol ratio, are fixed after preheating continuously into the first segment equipped with solid acid catalyst
Bed reactor carries out condensation reaction, and reaction product enters rectifying column dehydration；Dewatered material is in rectifying column stripping section lower part quilt
It continuously extracts out, and the charging as second segment condensation reaction is sent in second segment fixed bed reactors and continues condensation instead
It answers.The molar ratio of raw material MIBK and glycerol into first segment fixed bed reactors are 2-6:1, preferred scope 3-4:1；In essence
Evaporating tower stripping section to extract and be input to the mass flow of second segment fixed bed reactors out is first segment fixed bed reactors inlet amount
1-5 times, preferred scope be 2-3 times.Equally, the product of second segment condensation reaction is in the reaction product with first segment condensation reaction
After merging, rectifying column dehydration is entered back into.
In two fixed bed reactors, first segment setting-up point is 85-100 DEG C, preferred scope 90-
100℃；Air speed is 1-5h-1, preferred scope 3-4h-1.Second segment setting-up point is 95-115 DEG C, and preferred scope is
100-110℃；Air speed is 5-10h-1, preferred scope 6-8h-1。
Condensation reaction water generated is removed in a manner of azeotropic distillation in rectifying column, and used water entrainer is benzene or ring
Hexane.First segment and the reaction product of second segment condensation reaction enter carry out azeotropic distillation, water and water entrainer from rectifier
The azeotropic mixture of formation is steamed from the top of the distillation column, after condenser condenses, into layering tank, and layering tank in be divided into it is organic
It is mutually brought out with water phase, lower layer's water phase, upper organic phase is water entrainer, flows back into rectifying column and uses again.
Unreacted MIBK, glycerol and purpose object condensation product 2- methyl -2- isobutyl group -4- methylol -1,3-
Dioxolanes is discharged by rectifying tower reactor bottom, and into MIBK rectifying column, the fraction that tower top steams is MIBK, is recycled.Recycling
MIBK can be used as reaction raw materials cycling and reutilization.MIBK rectifying column materials at bottom of tower is purpose object 2- methyl -2- isobutyl
Base -4- methylol -1,3-dioxolane and a small amount of unreacted glycerol mixture.
MIBK rectifying column materials at bottom of tower is sent to product rectifying column rectifying, the available 2- methyl -2- of overhead extraction is different
Butyl -4- methylol -1,3-dioxolane high purity product.Tower bottom, which produces to obtain glycerol, can be used as reaction raw materials circulation
It recycles.
Fig. 1 is to prepare 2- methyl -2- isobutyl group-using two sections of fixed bed continuous reactions of solid acid catalyst
4- methylol -1,3-dioxolane technique main part flow chart.
In Fig. 1,1For the first segment fixed bed reactors equipped with solid acid catalyst,2For equipped with solid acid catalyst
Second segment fixed bed reactors,3For rectifying column,4For condenser,5To be layered tank,6For first segment fixed bed reactors feed pipe
Road,7For second segment fixed bed reactors feeding pipe,8It is condensation reaction material into rectifying column pipeline,9It is exported for water phase,10For
Water entrainer flows back into rectifying column pipeline,11MIBK rectifying column pipeline is sent to for tower bottom of rectifying tower material.
MIBK and glycerol stocks it is preheated after by6Into the first segment fixed bed reactors that solid acid catalyst is housed1,
Condensation reaction occurs for MIBK and glycerol under catalyst action, to be conducive to Xiang Jinhang before condensation reaction, conversion ratio is improved, by first
Section fixed bed reactors 1 reaction mass by8It is sent into rectifying column3Dehydration.In rectifying column3In, the water that condensation reaction generates is in institute
It states and is constantly separated from tower top in 68-71 DEG C of formation azeotropic mixture in the presence of water entrainer.Condensation reaction material is by de-
It is continuously extracted after water in 3 stripping pars infrasegmentalis of rectifying column, by7It is sent to second segment fixed bed reactors2It is anti-to continue condensation
It answers.It is first segment fixed bed reaction in the mass flow that second segment fixed bed reactors 2 were extracted and be input to 3 stripping section of rectifying column out
1-5 times of 1 inlet amount of device, preferred scope are 2-3 times.By second segment fixed bed reactors 2 react material equally by8 intoEnter
Rectifying column3Separation removal moisture.Rectifying column3Tower top steaming thing is through condenser4After condensation, into layering tank5, and in layering tank5
In be divided into organic phase and water phase, lower layer's water phase is drawn from 9, and upper organic phase is water entrainer, by10Flow back into rectifying column3.Contracting
2- methyl -2- isobutyl group -4- methylol-the 1,3-dioxolane and unreacted MIBK and glycerol that reaction generates are closed,
By rectifying column3Bottom discharging warp11Rectifying (is not marked) in Fig. 1 into the MIBK tower being further provided with, the extraction of MIBK rectifying tower top
MIBK recycles Recycling, and it is purpose object 2- methyl -2- isobutyl group -4- methylol-that MIBK rectifying column bottom, which produces material,
The mixture of 1,3-dioxolane and a small amount of unreacted glycerol.
MIBK tower materials at bottom of tower is sent to product rectifying column rectifying, overhead extraction obtains 2- methyl -2- isobutyl group -
4- methylol -1,3-dioxolane high purity product.Tower bottom produces to obtain glycerol, and to can be used as reaction raw materials circulation sharp again
With.
The utility model has the advantages that 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane producer of the invention
Method can expeditiously realize methylol -1 2- methyl -2- isobutyl group -4- by the new process of continuous production,
The industrialized production of 3- dioxolanes product, and mode of operation is simple, high production efficiency, reduces in production process useless
The discharge of slag waste water；Reaction product is neutralized without a large amount of alkali, and production cost reduces.Continuous reaction of the invention
2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane method is prepared, there is good economic benefit and environment
Benefit.
The present invention will be described in detail combined with specific embodiments below.The scope of the present invention is not with specific embodiment
It is limited, but is limited by the scope of the claims.
Detailed description of the invention
Fig. 1 successive reaction prepares the process flow of 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane
Schematic diagram.
Specific embodiment
Detailed description of the preferred embodiments below, it should be noted however that protection of the invention
Range is not limited to these specific embodiments, but is determined by claims.
Embodiment 1
By be preheated to 95 DEG C raw material MIBK and glycerol in molar ratio 3:1, continuously inputted equipped with 5L solid with 15L/h flow
The first segment fixed bed reactors 1 of acid catalyst, 95 DEG C of setting-up point, air speed 3h-1.Solid acid catalyst is compound increasing
Strong type macroporous polystyrene sulfonic acid type storng-acid cation exchange resin, the molal quantity of divinylbenzene accounts in polymerized monomer
25%, and the 50% (wt/ of micron order graphite whisker and polymerized monomer total amount that weight accounts for polymerized monomer total amount 1% (wt/wt) is added
Wt pore-foaming agent).The material reacted through first segment fixed bed reactors 1 enters rectifying column 3, and in rectifying column 3, condensation reaction is raw
At water in the presence of water liquid benzene, constantly separated in 68-71 DEG C of formation azeotropic mixture.The material of moisture is removed in essence
The stripping section of tower 3 is evaporated continuously to be extracted with 30L/h flow and be transported to the second segment fixed bed equipped with 5L solid acid catalyst
Reactor 2 continues condensation reaction, and 105 DEG C of reaction temperature, air speed 6h-1.It is input to the object of second segment fixed bed reactors 2
Stream amount is 2 times of 1 inlet amount of first segment fixed bed reactors.The material reacted by second segment fixed bed reactors 2 is same
Into 3 separation removal moisture of rectifying column, 3 tower top steaming thing of rectifying column into layering tank 5, and is being layered after the condensation of condenser 4
It is divided into organic phase and water phase in tank 5, water phase is brought out, and organic phase flows back into rectifying column 3 for water liquid benzene and uses again.Rectifying column 3
Tower reactor discharging composition mass ratio are as follows: MIBK56.09%, 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane
40.96%, glycerol 2.66%, other impurities 0.29%.The discharging of 3 tower reactor of rectifying column enters the MIBK rectifying column essence being further provided with
It evaporates, the MIBK of overhead extraction recycles Recycling, and kettle material is sent to the purifying of product rectifying column, and product the top of the distillation column is per hour
Can output 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane product 5.62kg, product purity 99.6%.
Tower bottom, which produces to obtain glycerol, can be used as reaction raw materials cycling and reutilization.Using two sections of fixed bed continuous reaction results: glycerol
Conversion per pass 89% generates 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane selectivity 99%.
Embodiment 2
By be preheated to 100 DEG C raw material MIBK and glycerol in molar ratio 2:1, continuously inputted with 20L/h flow and consolidated equipped with 5L
The first segment fixed bed reactors 1 of body acid catalyst, 100 DEG C of setting-up point, air speed 4h-1.Solid acid catalyst is multiple
Enhanced macroporous polystyrene sulfonic acid type storng-acid cation exchange resin is closed, the molal quantity of divinylbenzene in polymerized monomer
35% is accounted for, and micron order graphite whisker and polymerized monomer total amount 60% that weight accounts for polymerized monomer total amount 3% (wt/wt) is added
(wt/wt) pore-foaming agent.The material reacted through first segment fixed bed reactors 1 enters rectifying column 3, and in rectifying column 3, condensation is anti-
The water that should be generated constantly is separated in the presence of cyclohexane in 69-71 DEG C of formation azeotropic mixture.Remove the contracting of moisture
Reaction mass is closed to be continuously withdrawn and be transported to equipped with 5L solid acid catalyst with 40L/h flow in the stripping section of rectifying column 3
Second segment fixed bed reactors 2,110 DEG C of setting-up point, air speed 8h-1.It is input to second segment fixed bed reactors 2
Mass flow is 2 times of 1 inlet amount of first segment fixed bed reactors.The material reacted by second segment fixed bed reactors 2 is same
Sample enters 3 separation removal moisture of rectifying column, and 3 tower top steaming thing of rectifying column is after the condensation of condenser 4, into layering tank 5, and is dividing
It is divided into organic phase and water phase in layer tank 5, water phase is brought out, and organic phase is hexamethylene, returns to rectifying column 3.3 tower reactor of rectifying column
Discharging composition are as follows: MIBK40.91%, 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane 54.44%, it is sweet
Oil 4.34%, other impurities 0.31.Tower bottom of rectifying tower discharging enters the MIBK rectifying column rectifying being further provided with, overhead extraction
MIBK recycles Recycling, and kettle material is sent to the purifying of product rectifying column, and product the top of the distillation column per hour can output 2- first
Base -2- isobutyl group -4- methylol -1,3-dioxolane product 10.20kg, product purity 99.5%.Tower bottom produces
It can be used as reaction raw materials cycling and reutilization to glycerol.Using two sections of fixed bed continuous reaction results: glycerol conversion per pass
87%, generate 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane selectivity 98%.
Claims (9)
1. a kind of preparation method of 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane, it is characterised in that:
Using hexone and glycerol as raw material, a serialization condensation reaction is fixed using solid acid catalyst, it is described
Solid acid catalyst is composite enhanced macroporous polystyrene sulfonic acid type storng-acid cation exchange resin；Reaction temperature 85-115
DEG C, the water for reacting generation is removed through azeotropic distillation；The later reaction product rectifying of water will be removed, removes and recycles excessive unreacted
Hexone, obtain 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane.
2. the preparation side of 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane according to claim 1
Method, it is characterised in that: sulfonation is made after the ion exchange resin is polymerize by styrene and divinylbenzene monomers, polymerize
The molal quantity of divinylbenzene accounts for 20~35% in monomer, and the micron order graphite that weight accounts for polymerized monomer total amount 1~3% is added
Whisker and 40~70% pore-foaming agent.
3. the preparation side of 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane according to claim 1
Method, it is characterised in that: the fixed bed serialization condensation reaction is the fixed bed that solid acid catalyst is filled at two
Two sections of condensation reactions being carried out continuously in reactor, first segment condensation reaction products elimination reaction generate water after carry out second segment
Condensation reaction.
4. 2- methyl-2- isobutyl group-4- methylol according to claim 3-1,3-dioxolane preparation side
Method, it is characterised in that: the fixed bed continuous condensating reaction includes that raw material hexone is mixed and preheated with glycerol
Afterwards, condensation reaction is carried out continuously into the first segment fixed bed reactors equipped with solid acid catalyst, reaction product enters essence
Evaporate tower dehydration；Dewatered material is continuously withdrawn in rectifying column stripping section lower part, and as second segment contractingization reaction into
Material, which is sent in second segment fixed bed reactors, continues condensation reaction.
5. the system of 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane according to claim 3 or 4
Preparation Method, it is characterised in that: the molar ratio of raw material hexone and glycerol into first segment fixed bed reactors is
2-6:1；The mass flow for entering second segment fixed bed reactors is 1-5 times of first segment fixed bed reactors inlet amount.
6. the system of 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane according to claim 3 or 4
Preparation Method, it is characterised in that: first segment setting-up point is 85-100 DEG C, and second segment setting-up point is 95-115 DEG C.
7. the system of 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane according to claim 3 or 4
Preparation Method, it is characterised in that: the condensation reaction air speed of the first segment fixed bed reactors is 1-5h-1, second segment fixed bed
The condensation reaction air speed of reactor is 5-10h-1。
8. the preparation side of 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane according to claim 1
Method, it is characterised in that: the water entrainer that the azeotropic distillation uses is benzene or hexamethylene.
9. the preparation side of 2- methyl -2- isobutyl group -4- methylol -1,3-dioxolane according to claim 1
Method, it is characterised in that: it is rectifying to obtain methylol -1 2- methyl -2- isobutyl group -4- after condensation reaction material removing water,
3- dioxolanes product.
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| CN110527015A (en) * | 2019-08-29 | 2019-12-03 | 苏州长业材料技术有限公司 | A kind of preparation method of modified poly ester and coating containing the modified poly ester |
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