CN105753663B - A kind of preparation method of butoxymethoxy methane - Google Patents
A kind of preparation method of butoxymethoxy methane Download PDFInfo
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- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
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Abstract
A kind of preparation method of butoxymethoxy methane is related to a kind of preparation method of methane, the synthesis path of butyl glycol ether of the present invention, which includes three steps, and first step dimethoxym ethane and butanol synthesize butoxymethoxy methane；Second step butoxymethoxy methane orientation carbonylation, generates butoxy acetic acid methyl esters；Third walks butoxy acetic acid methyl ester hydrogenation and generates butyl glycol ether and methanol；Using dimethoxymethane and n-butanol as raw material, at temperature and pressure, using resin as catalyst, butoxymethoxy methane is prepared.Open the preparation method of the synthesis path and butoxymethoxy methane of a completely new butyl glycol ether.Raw material needed for this method is cheap and easy to get and whole flow process is easy to operate, and product is single and high selectivity, has a good application prospect, and is suitble to industrialized production.
Description
Technical field
The present invention relates to a kind of preparation methods of methane, more particularly to a kind of preparation side of butoxymethoxy methane
Method.
Background technology
Butyl glycol ether（HOCH2CH2OCH2CH2CH2CH3）, colourless flammable liquid, with moderate ether taste, boiling point 171
℃.Due to not only containing ehter bond in its molecule but also containing hydroxyl, this unique property makes it both can dissolve organic molecule, synthesis
Or natural high-molecular compound, and can dissolve each other to some extent with water or water soluble compound, thus be used as applying extensively
The uses such as material, ink, cleaning agent, pharmaceutical extraction agent.According to statistics, China's coating, ink industry in 2010 about consume glycol ether
200000 tons, account for about the 80% of glycol ether aggregate consumption.Cleaning agent industry about consumes 20,000 tons of glycol ether, and it is total to account for about glycol ether
The 8% of consumption figure, it can be seen that paint solvent is still the largest application areas of glycol ether.However recently some researches show that,
Gylcol ether（Especially methyl ether and ether）Hematologic disease and fetal anomaly are may result in, beginning limits for developed country
It makes its production and uses.But butyl glycol ether does not show similar toxicity, it is external its not as hazardous materials transportation and storage.
Therefore ethylene glycol monomethyl ether and ether is replaced to use in a solvent by butyl glycol ether imperative.Currently, in China's ethylene glycol fourth
Ether dosage is maximum, and dosage accounts for about the 60% of gylcol ether product consumption total amount.But since the country produces butyl glycol ether
Technology it is immature, the source of China's butyl glycol ether depends on import, and import volume accounts for 90% of total amount or more, and close several
Year, China grew at top speed again for the demand of butyl glycol ether with 10% average growth rate per annum, and imbalance of supply and demand phenomenon is on the rise.Cause
This opens up a practicable butyl glycol ether production ways and is particularly important.
Consulting literatures and patent are it is found that the synthetic method of butyl glycol ether mainly has following two approach：
One, using ethylene oxide and butanol as raw material preparing ethylene glycol butyl ether
Such as equation（1）Shown, Zhang Mu exists《Petrochemical industry》Second is prepared with the response path in supplementary issues of volume 37 in 2008
Glycol butyl ether.This method is prepared using heteropoly acid as catalyst in 70~120 DEG C of low pressure using ethylene oxide and n-butanol as raw material
Butyl glycol ether, glycol product butyl ether selectively up to 75%.However the byproduct of reaction is more, and be strong exothermal reaction, instead
It should be not easily controlled, a large amount of butyl, triethylene glycol butyl ether, tetraethylene glycol butyl ether, five ethylene glycol are contained in product
Butyl ether, six butyl glycol ethers and corresponding bis ether, later separation is difficult, and energy consumption is higher.
Two, synthesis gas formaldehyde method preparing ethylene glycol butyl ether
Such as equation（2）Shown, Japanese chemists Kurashiki is in 4071568 intermediaries of United States Patent
It continues using synthesis gas, formaldehyde and n-butanol as raw material, is catalyst under the conditions of 100~250 DEG C, 50 Mpa extremely high pressures using cobalt
Synthesizing butyl cellosolve, wherein butyl glycol ether yield are up to 55.6%.But the disadvantages of this method is that reaction is needed in extra-high voltage
Lower progress needs 500 atmospheric pressure, high to consersion unit requirement, and the preparation process of the Co catalysts reacted is cumbersome, nothing
Method is reused, therefore is used without using in large-scale industrial production.
Three, ethylene glycol reacts preparing ethylene glycol butyl ether with butanol
Such as equation（3）It is shown, using ethylene glycol and butanol as reaction raw materials, ethylene glycol fourth is prepared under acid catalysed conditions
Ether, this method are the preparation methods of industrial butyl glycol ether at present.But the reaction product is more complex, there is butyl cellosolve,
Butyl ether, diethanol butyl ether, dibutyl ethylene glycol ether etc., later separation is difficult, and energy consumption is higher.
Based on the above reason, we open a kind of synthesis path of completely new butyl glycol ether, the first step by dimethoxym ethane and
The highly selective synthesis butoxymethoxy methane of butanol；Second step butoxymethoxy methane orientation carbonylation, generates fourth oxygen
Acetic acid methyl ester；Third walks butoxy acetic acid methyl ester hydrogenation and generates butyl glycol ether and methanol.Wherein third step ester through hydrogenation reaction
It is very easy to carry out, and selectivity is higher.Second step orients carbonylation, all it has been reported that crossing dimethoxym ethane in document and patent
The highly selective generation methoxy menthyl acetate of carbonylation.The synthesis of first step reaction raw materials methoxybutoxy methane only, at present
The report in relation to specific synthetic method and path is had no on SciFinder.
Invention content
The purpose of the present invention is to provide a kind of preparation methods of butoxymethoxy methane, and the present invention provides completely new
The synthesis path of butyl glycol ether, the response path product is single, and raw material is simple and easy to get, and selectivity of product is high and anti-without high pressure
Answer condition that can carry out, compared to epoxyethane method and glycol method synthesizing butyl cellosolve path, product it is relatively single and
Cost is reduced significantly.
The purpose of the present invention is what is be achieved through the following technical solutions：
A kind of preparation method of butoxymethoxy methane, the method includes following procedure：
A. the synthesis path of butyl glycol ether, the path include three steps, the first step such as equation（1）It is shown, dimethoxym ethane and
Butanol synthesizes butoxymethoxy methane；Second step such as equation（2）Shown, butoxymethoxy methane orientation carbonylation is raw
At butoxy acetic acid methyl esters；Third step such as equation（3）Shown, butoxy acetic acid methyl ester hydrogenation generates butyl glycol ether and first
Alcohol；
B. butoxymethoxy methane is prepared：Using dimethoxymethane and n-butanol as raw material, at temperature and pressure, with
Resin is catalyst, prepares butoxymethoxy methane.
A kind of preparation method of the butoxymethoxy methane, the resin catalyst be KAD302, KC107,
The one or more resin catalysts of NKC-9, DA-330, D009B, Amberlyst-15, D072H；Resin catalyst is to contain sulfonic acid
Based on the resin catalyst of group.
A kind of preparation method of butoxymethoxy methane, the reaction temperature are 0~160 DEG C, reaction pressure
For 0.1~10.0 MPa；Filling gas is inert gas, is argon gas, helium, and carbon dioxide is either a kind of or mixed in nitrogen
Close gas；Reactor is fixed bed or tank reactor, still more preferably tank reactor.
A kind of preparation method of butoxymethoxy methane, the raw material dimethoxymethane and n-butanol mole
Than being 1:2~5:1；Still more preferably 1:1.
Advantages of the present invention is with effect：
1. the advantages of synthesis butoxymethoxy methanol method is that by-product is less, target product selectivity is higher, instead
Mild condition is answered, product yield is higher, and has a good application prospect.And raw material dimethoxym ethane and butanol needed for this method are honest and clean
Valence is easy to get, and whole flow process is easy to operate, while this method does not generate the chemical substance of any pollution environment, belongs to environmental-friendly
The processing route of type.
2. the method for the present invention uses resin for catalyst, using dimethoxymethane and n-butanol as raw material, highly selective life
At butoxymethoxy methane.Entire building-up process product is simple, and side reaction is less, products therefrom butoxymethoxy methane
Selectivity is higher.
Description of the drawings
Influence curve figure of the reaction temperature to butoxymethoxy methane selectively when Fig. 1 is using NKC-9 as catalyst.
Specific implementation mode
The following describes the present invention in detail with reference to examples.
In the reaction of the present invention, raw material is it may also happen that following side reaction：
Actually it is by the mixture obtained after raw material dimethoxymethane and n-butanol reaction：Butoxymethoxy first
Alkane, dibutoxy methane and methanol, also a small amount of remaining reaction raw materials dimethoxymethane and n-butanol.
For the present invention, it is desirable to which dimethoxymethane and n-butanol are with molar ratio 1:1 reaction completely, generates molar ratio
It is 1:1 butoxymethoxy methane and methanol, without generating dibutoxy methane.The selectivity of two kinds of products can be by changing
The type of change catalyzer, reaction raw materials ratio, the temperature of reaction, reaction contact time, the conditions such as reaction pressure change.
In the present invention, product is detected and is determined by gas-chromatography and mass spectrometer analysis.Pass through gas-
Mass spectrometry analysis detection, it is determined that the mixture composition after reaction is simple, only dimethoxymethane, n-butanol, two fourth oxygen
Methylmethane, butoxymethoxy methane and methanol.
Embodiment 1
38 g dimethoxymethane, 37 g n-butanols and 3 g catalyst are added in 180 mL autoclaves, are catalyzed
Agent is respectively KAD302（The triumphant auspicious environmental protection in Beijing）, KC107（Tianjin, which permits, opens）、NKC-9（Its tunami letter）、DA-330（Jiang Sute
China）、D009B（Dandong jewel）、Amberlyst-15（Jiangsu Se Kesai thinks）、D072H（Tianjin, which permits, opens）.Use N2In 1.0 MPa
Under the conditions of air in displacement kettle three times, so that remaining air content is less than 0.1 %, and be passed through 2.0 MPa N again2,
30 min are stood, are leaked hunting for reaction kettle, it is ensured that empty gas reactor after device is air tight.Under the conditions of ensuring gastight,
Carry out heat temperature raising reaction, 500 revs/min, reaction pressure 0.1MPa of reaction kettle mixing speed, 70 DEG C of reaction temperature, reaction time
4 hours, reaction result was as shown in table 1.
Influence of the 1. different resins catalyst of table to dimethoxymethane and n-butanol reactivity and selectivity of product
From the response data of table 1 it is found that normal pressure, 70 DEG C, reaction raw materials dimethoxymethane and n-butanol with mole
Than 1：1 reaction 4 hours, different catalyst is affected to selectivity of product, butoxy methoxy when wherein catalyst is NKC-9
The selective highest of methylmethane is 88 %.
Embodiment 2
Normal pressure, under the conditions of 70 DEG C, it is 1 that molar ratio is added in 180 mL autoclaves:3、1:2、2:1、3:1、4:
1、5:1 raw material dimethoxymethane and n-butanol and 3 g NKC-9 catalyst（Wherein n-butanol quality is 37 g）, in room
N is used under the conditions of temperature2Air under the conditions of 1.0 MPa in displacement kettle three times, makes remaining air content in kettle be less than 0.1 %,
And it is passed through 2.0 MPa N again2, 30 min are stood, are leaked hunting for reaction kettle, it is ensured that empty gas reactor after device is air tight.
Under the conditions of ensuring gastight, heat temperature raising is carried out under normal pressure, 500 revs/min of reaction kettle mixing speed, the reaction time 4 is small
When, influence of the different ratios of raw materials to reactivity and selectivity of product is as shown in table 2.
Influence of 2. different ratios of raw materials of table to reactivity and selectivity of product
From Table 2, it can be seen that normal pressure, 70 DEG C, reaction pass through 4 hours, the reaction raw materials dimethoxy of different mol ratio
Methylmethane and n-butanol result obtained by the reaction are different, and levels of n-butanol is higher in raw material, the selection of butoxymethoxy methane
Property is lower, and the selectivity of the more low then butoxymethoxy methane of levels of n-butanol is higher in raw material.Improve dimethoxy in raw material
The molar ratio of methane and n-butanol can increase the selectivity of butoxymethoxy methane.
Embodiment 3
It is added 38 g dimethoxymethane in 180 mL autoclaves, 37 g n-butanols, 3 g NKC-9 catalyst,
N is used at ambient temperature2Air under the conditions of 1.0 MPa in displacement kettle three times, makes remaining air content in kettle be less than 0.1
%, and it is passed through 2.0 MPa N again2, 30 min are stood, are leaked hunting for reaction kettle, it is ensured that gas in emptying kettle after device is air tight
Body.Under the conditions of ensuring gastight, progress heat temperature raising, 500 revs/min of reaction kettle mixing speed, 4 hours reaction time, instead
It is respectively 25,40,60,80,100,120,130,140,150 and 160 DEG C to answer 0.1 MPa of pressure, reaction temperature, different anti-
Answer the reaction result under temperature condition as shown in table 3.
Influence of the 3. NKC-9 catalyst of table to reactivity and selectivity of product under differential responses temperature condition
From table 3 it is observed that when using NKC-9 as catalyst, reacted 4 hours under normal pressure, reactant dimethoxy
Methylmethane and n-butanol molar ratio are 1：When 1, temperature range be 25~120 DEG C of butoxymethoxy methane selectivelies with temperature
The raising of degree reduces, the conversion ratio and butoxymethoxy of dimethoxymethane, n-butanol when temperature range is 120~160 DEG C
Methane, dibutoxy methane selectivity all no longer change, the reason is that temperature is excessively high to lead to NKC-9 catalyst inactivations.From table 3
It could be assumed that：The selective higher of butoxymethoxy methane within the scope of relatively low temperature.
Embodiment 4
NKC-9 catalyst is selected, is added 38 g dimethoxymethane in 180 mL autoclaves, 37 g n-butanols, 3
G NKC-9 catalyst, uses N at ambient temperature2Air under the conditions of 1.0 MPa in displacement kettle makes remaining in kettle three times
Air content is less than 0.1 %, and is passed through 2.0 MPa N again2, 30 min are stood, are leaked hunting for reaction kettle, it is ensured that device does not leak
Gas reactor is emptied after gas.Under the conditions of ensuring gastight, heat temperature raising is carried out, temperature is 70 DEG C, reaction kettle mixing speed
500 revs/min, 4 hours reaction time, respectively pressure be 0.1 MPa, 1.0 MPa, 1.5 MPa, 2.0 MPa, 3.0 MPa,
It is reacted under 4.0 MPa, 6.0 MPa, 8.0 MPa, 10.0 MPa, such as table 4 of the reaction result under differential responses pressure condition
It is shown.
From table 4, it can be seen that when using NKC-9 as catalyst, 70 DEG C of 4 hours reaction time, reactant dimethoxy
Methylmethane and n-butanol molar ratio are 1：It is 0.1~10.0 MPa, raw material dimethoxymethane and positive fourth in pressure limit when 1
The conversion ratio of alcohol is improved with the increase of pressure, and the selectivity of product butoxymethoxy methane is in 0.1~1.5 MPa ranges
Increased with the raising of pressure, but under conditions of 1.5~10.0 MPa relatively high pressures selectively with the raising of pressure and
It reduces.Butoxymethoxy methane has higher selectivity in the pressure limit of 0.1~1.5 MPa.
Influence of the 4. NKC-9 catalyst of table to reactivity and selectivity of product under differential responses pressure condition
。
Embodiment 5
NKC-9 catalyst is selected, is added 38 g dimethoxymethane in 180 mL autoclaves, 37 g n-butanols, 3
G NKC-9 catalyst, uses N at ambient temperature2Air under the conditions of 1.0 MPa in displacement kettle makes remaining in kettle three times
Air content is less than 0.1 %, and is passed through 2.0 MPa N again2, 30 min are stood, are leaked hunting for reaction kettle, it is ensured that device does not leak
Gas reactor is emptied after gas.Under the conditions of ensuring gastight, heat temperature raising is carried out under normal pressure, temperature is set as 70 DEG C, reaction kettle
500 revs/min of mixing speed, reaction time are respectively 2 hours, 4 hours, 6 hours, 8 hours, 10 hours, differential responses pressure strip
Reaction result under part is as shown in table 5.
Influence of the 5. NKC-9 catalyst of table to reactivity and selectivity of product under differential responses time conditions
As can be seen from Table 5, when using NKC-9 as catalyst, 70 DEG C, synthesis under normal pressure, reactant dimethoxy first
Alkane and n-butanol molar ratio are 1：When 1, the reaction time short generation conducive to butoxymethoxy methane, reaction time longer reaction
More abundant, the selectivity of butoxymethoxy methane is lower.
Embodiment 6
It is added 38 g dimethoxymethane in 180 mL autoclaves, 37 g n-butanols and the different NKC- of quality
9 catalyst, use N at ambient temperature2Air under the conditions of 1.0 MPa in displacement kettle makes remaining air in kettle contain three times
Amount is less than 0.1 %, and is passed through 2.0 MPa N again2, 30 min are stood, are leaked hunting for reaction kettle, it is ensured that the air tight heel row of device
Empty gas reactor.Under the conditions of ensuring gastight, heat temperature raising is carried out under normal pressure, 70 DEG C are reacted, reaction kettle stirring speed
500 revs/min of degree, in 4 hours reaction time, the NKC-9 catalyst of different quality is to dimethoxymethane and n-butanol reactivity
And the influence of selectivity of product is as shown in table 6.
The NKC-9 catalyst of 6. different quality of table is to dimethoxymethane and n-butanol reactivity and selectivity of product
It influences
As can be seen from Table 6, it at 70 DEG C, is reacted 4 hours under normal pressure, reactant dimethoxymethane and n-butanol mole
Than being 1：When 1, when the quality of catalyst increases the conversion ratio increase of dimethoxymethane, n-butanol, while butoxymethoxy
The selectivity of methane reduces, after catalyst quality is more than 7 g, dimethoxymethane, the conversion ratio of n-butanol and butoxy first
The selectivity variation of oxygroup methane is little, the reason is that catalytic amount reaches saturation value.
Embodiment 7
Under condition of normal pressure, 38 g dimethoxymethane, 37 g n-butanols and 3 g are added in 180 mL autoclaves
Catalyst, catalyst are respectively KAD302, KC107, D009B, DA-330, temperature be respectively 50 DEG C, 70 DEG C, 90 DEG C,
N is used under the conditions of 130 DEG C, 160 DEG C2Air under the conditions of 1.0 MPa in displacement kettle makes remaining air content in kettle three times
Less than 0.1 %, and it is passed through 2.0 MPa N again2, 30 min are stood, are leaked hunting for reaction kettle, it is ensured that emptying after device is air tight
Gas reactor.Under the conditions of ensuring gastight, progress heat temperature raising reaction under normal pressure, 500 revs/min of reaction kettle mixing speed,
4 hours reaction time, various resin catalysts at different temperatures under the conditions of raw material dimethoxymethane and n-butanol reaction live
The results are shown in Table 7 for property and selectivity of product.As can be seen from Table 7, it reacts 4 hours in atmospheric conditions, reactant dimethoxy
Methylmethane and n-butanol molar ratio are 1：When 1, with the raising of temperature, the reaction of various catalysts, reactant dimethoxy
The conversion ratio of methylmethane and n-butanol all increases, and high temperature is unfavorable for the raising of product butoxymethoxy methane selectively.It is various
Resin catalyst can all inactivate after reaction temperature is higher than 130 DEG C, can not continue to improve selectivity and conversion ratio, it is seen that table
Resin catalyst in lattice is not suitable for the reaction of high temperature.
The influence of table 7. various catalyst reactivity and selectivity of product under condition of different temperatures
。
Embodiment 8
38 g dimethoxymethane, 37 g n-butanols, 3 g catalyst, catalyst are added in 180 mL autoclaves
Respectively KAD302, KC107, D009B, DA-330 use N at ambient temperature2The air in kettle is replaced under the conditions of 1.0 MPa
Three times, so that remaining air content in kettle is less than 0.1 %, and be passed through 2.0 MPa N again2, 30 min are stood, reaction kettle is used for
It leaks hunting, it is ensured that gas reactor is emptied after device is air tight.Under the conditions of ensuring gastight, heat temperature raising, temperature 70 are carried out
DEG C, 500 revs/min of reaction kettle mixing speed, 4 hours reaction time, respectively pressure be 0.1 MPa, 1.5 MPa, 2.0 MPa,
Reacted under 6.0 MPa, 10.0 MPa, various catalyst at various pressures under the conditions of raw material dimethoxymethane and positive fourth
Alcohol reactivity and selectivity of product are as shown in table 8.
As can be seen from Table 8, it at 70 DEG C, reacts 4 hours, reactant dimethoxymethane and n-butanol molar ratio are 1：1
When, the reaction of various catalysts, the conversion ratio for increasing stress reaction object dimethoxymethane and n-butanol all increases, but produces
The selectivity of object butoxymethoxy methane still conforms to the rule of embodiment 4.
The influence of 8. different catalysts of table reactivity and selectivity of product under the conditions of different pressures
。
Embodiment 9
38 g dimethoxymethane, 37 g n-butanols are added in 180 mL autoclaves, catalyst is respectively 3 g
KAD302, KC107, D009B, DA-330 use N in atmospheric conditions2Under the conditions of 1.0 MPa replace kettle in air three times,
So that remaining air content in kettle is less than 0.1 %, and is passed through 2.0 MPa N again2, 30 min are stood, are leaked hunting for reaction kettle,
Ensure to empty gas reactor after device is air tight.Under the conditions of ensuring gastight, heat temperature raising, reaction temperature are carried out under normal pressure
70 DEG C, 500 revs/min of reaction kettle mixing speed, the reaction time is respectively 2 hours, 4 hours, 6 hours, 8 hours, 10 hours, instead
Answer that the results are shown in Table 9.
As can be seen from Table 9, in 70 DEG C, normal pressure, reactant dimethoxymethane and n-butanol molar ratio are 1：When 1, increase
The conversion ratio of reaction time reactant dimethoxymethane and n-butanol is added all to increase, but the choosing of product butoxymethoxy methane
Selecting property still conforms to the rule of embodiment 5.
Influence of 9. different catalysts of table under differential responses time conditions to reactivity and selectivity of product
The above is only several embodiments of the application, not does any type of limitation to the application, although this Shen
Please disclosed as above with preferred embodiment, however not to limit the application, any person skilled in the art is not taking off
In the range of technical scheme, makes a little variation using the technology contents of the disclosure above or modification is equal to
Case study on implementation is imitated, is belonged in technical proposal scope.
Claims (1)
1. a kind of preparation method of butyl glycol ether, which is characterized in that the method includes following procedure：
A. the synthesis path of butyl glycol ether, the path include three steps, the first step such as equation（1）It is shown, dimethoxym ethane and butanol
Synthesize butoxymethoxy methane；Second step such as equation（2）Shown, butoxymethoxy methane orientation carbonylation generates fourth
Ethoxyacetic acid methyl esters；Third step such as equation（3）Shown, butoxy acetic acid methyl ester hydrogenation generates butyl glycol ether and methanol；
CH3OCH2OCH3 + CH3CH2CH2CH2OH → CH3CH2CH2CH2OCH2OCH3+CH3O(1)
CH3CH2CH2CH2OCH2OCH3 + CO → CH3CH2CH2CH2OCH2COOCH3 (2)
CH3CH2CH2CH2OCH2COOCH3 +H2 → HOCH2CH2OCH2CH2CH2CH3+CH3OH(3)
B. butoxymethoxy methane is prepared：Using dimethoxymethane and n-butanol as raw material, at temperature and pressure, with resin
For catalyst, butoxymethoxy methane is prepared；
The resin catalyst is based on the resin catalyst containing sulfonic acid group；
The reaction temperature is 0~160 DEG C, and reaction pressure is 0.1~10.0 MPa；Filling gas is inert gas, is argon gas,
Helium, carbon dioxide either one kind or gaseous mixture in nitrogen；Reactor is fixed bed or tank reactor；The original
Expect that dimethoxymethane and n-butanol molar ratio are 1:2~5:1.
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