CN107602354A - A kind of method of synthesizing propanediol butyl ether - Google Patents
A kind of method of synthesizing propanediol butyl ether Download PDFInfo
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- CN107602354A CN107602354A CN201710832738.8A CN201710832738A CN107602354A CN 107602354 A CN107602354 A CN 107602354A CN 201710832738 A CN201710832738 A CN 201710832738A CN 107602354 A CN107602354 A CN 107602354A
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- butyl ether
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- expoxy propane
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Abstract
The present invention relates to a kind of method of synthesizing propanediol butyl ether, this method is that KF/MgO is solid base catalyst, and closed stirring, uses N in a kettle using n-butanol and expoxy propane as raw material2Air in kettle is displaced, is heated to design temperature, reacts synthesizing propanediol butyl ether；Described reaction process condition is that material molar ratio is n-butanol：Expoxy propane=1~5:1, reaction temperature is 110~140 DEG C, and catalyst quality percentage is the 0.5~2% of gross mass；The KF/MgO solid base catalysts are prepared using solid-phase sequencing, and are made by high-temperature roasting.It is an advantage of the invention that：The reaction being catalyzed using KF/MgO solid base catalysts, the conversion ratio of expoxy propane and the yield of propandiol butyl ether will be higher than the reaction of traditional catalyst NaOH catalysis.The problems such as traditional etherification technology is harsh to equipment requirement, and product processing is more difficult is turn avoid simultaneously, and catalyst is easily separated, reusable, energy-conserving and environment-protective.
Description
Technical field
The present invention relates to the synthesis of propandiol butyl ether, and specifically n-butanol and expoxy propane is raw material, in catalyzed by solid base
In the presence of agent KF/MgO, expoxy propane open loop insertion n-butanol reaction synthesizing propanediol butyl ether.Belong to fine chemicals technology
Field.
Background technology
Contain ehter bond and hydroxyl in propandiol butyl ether molecular structure, the former has lipophile, can be with hydrophobic compound
Dissolve each other, the latter has hydrophily, can be dissolved each other with hydrophilic compounds, thus the title with " alembroth ".
Propandiol butyl ether is one of staple product of propylene glycol ether series, is a kind of excellent solvent, is widely used in coating,
Pigment, ink, efficient cleaner, printing, the industry such as leather and electronic chemical product.Compared with glycol ether, propylene glycol
Toxicity substantially reduce, therefore propylene glycol can effectively substitute glycol ether, and be connect by increasing user
By.
Propylene oxide method is the method for the industrial synthesizing propanediol butyl ether generally used at present, is also had in addition
The methods of Willamson methods and acetal method, due to there are various problems so applied to the less of actual industrialization in the latter.Mesh
It is preceding that mainly propylene oxide method synthesizing propanediol butyl ether is studied from reactor and catalyst this two broad aspect both at home and abroad.The U.S.
Dow Chemical companies develop a kind of insoluble containing positive phosphonium ion (PR4 +) polyalcohol catalyst；BPChemicals is public
Department develops a kind of metal perfluorinated sulfonic acid polymer and urges mixture, for being catalyzed the addition reaction of expoxy propane and methanol；Li Zhisong
Deng using phosphomolybdate Modification on Al2O3Make catalyst, using catalytic distillation new technique for synthesizing, the synthesis for propylene glycol monobutyl ether.
Catalyst is generally industrially used as using traditional homogeneous acid or alkalescence, but which results in corrosive equipment, catalyst
The problems such as hardly possible separates with product, particularly also there is the problem of poor selectivity, accessory substance is more in solid acid catalyst.Therefore, need badly
We develop a kind of high activity, environment-friendly catalyst, improve inductrial technology technical merit and product quality.
The content of the invention
It is acid this method avoid conventional homogeneous it is an object of the invention to provide a kind of method of synthesizing propanediol butyl ether
Or alkalescence is used as corrosive equipment caused by catalyst, catalyst is difficult the problems such as separation with product, and this method technique is simple, energy
Consume low, and catalyst is easily separated, reusable, energy-conserving and environment-protective.
The object of the present invention is achieved like this：N-butanol, catalyst are added in reactor, sealing stirring, use N2
Air in kettle is displaced, is heated to design temperature, is slowly introducing expoxy propane, and controls reactor temperature substantially permanent
Fixed, control reacting kettle inner pressure after expoxy propane is passed through setting quality, continues to enter under established temperature in 0.20~0.50MPa
Row reaction, until pressure is constant in kettle, and keeps constant in 30min, reaction cools and discharged after terminating, and obtains propandiol butyl ether
Product.
Described catalyst is KF/MgO solid base catalysts.
KF/MgO solid base catalysts provided by the invention are prepared in accordance with the following methods：Will quantitative magnesium chloride solution with
Precipitating reagent sodium hydroxide, sodium carbonate reaction, for control process conditions in 40~100 DEG C of 1~24h of crystallization, it is heavy to be filtered out after a few hours
Starch, dry to constant weight, then be placed in Muffle furnace 1~8h of high-temperature roasting at 300~1000 DEG C, high dispersive carrier MgO is made.
The KF of certain load capacity and carrier MgO are sufficiently mixed with solid-phase sequencing again, dry to constant weight, then be placed in Muffle furnace in
1~8h of high-temperature roasting at 300~1000 DEG C, solid base catalyst KF/MgO is made.
Limited as another step to the present invention, raw material molar ratio is n-butanol in the method for the invention：Epoxy
Propane=1~5:1, reaction temperature is 110~140 DEG C, and reaction pressure is 0.20~0.50MPa, and catalyst quality percentage is used
Measure 0.5~2% for raw material n-butanol and expoxy propane gross mass.
Limited as another step to the present invention, more suitable feed molar proportioning is positive fourth in the method for the invention
Alcohol：Expoxy propane=4:1, reaction temperature is 130 DEG C, and catalyst quality percentage dosage is that raw material n-butanol and expoxy propane are total
The 1.5% of quality, the mol ratio for preparing the precipitating reagent sodium hydroxide used in carrier MgO and sodium carbonate is 1:1, KF load capacity is
The 30% of MgO mass.
The solid base catalyst is filtered to be separated with product, can be recycled, environmental protection and economy.
It is an advantage of the invention that：After reaction solid base catalyst catalytic reaction used, the conversion ratio of expoxy propane and third
The yield of glycol butyl ether, which will be higher than, industrially applies traditional catalyst NaOH.It turn avoid conventional homogeneous catalytic erosion simultaneously
The problems such as equipment, more difficult product processing, with catalytic activity is high, selectivity is good, catalyst can be recycled, reaction condition temperature
The low and advantages such as environmental pollution is small with, energy consumption easily separated with product.
Brief description of the drawings
Fig. 1 is the TEM figures that different MgO carriers prepare KF/MgO, wherein figure (a) is commercially available MgO loads KF TEM figures；Figure
(b) KF TEM figures are loaded for self-control MgO；
Fig. 2 is solid base catalyst KF/MgO XRD spectra.
Embodiment
Invention is described further by following instance, but and is not so limited the present invention.
In embodiment, each content of material in product is to carry out quantitative analysis with gas chromatography.Using GC9790 types
Gas chromatograph, split sampling, equipped with temperature programming part, flame ionization ditector.Capillary chromatograph is PEG20000
Type 30m × 0.32mm × 0.45 μm.
In embodiment, the conversion ratio of expoxy propane and the yield of propandiol butyl ether obtain according to the following formula：
The catalyst KF/MgO solid base catalysts used in embodiments of the invention, its preparation method are：
Quantitative magnesium chloride solution is reacted with precipitating reagent sodium hydroxide, sodium carbonate, control process conditions are in 40~100 DEG C of crystalline substances
Change 1~24h, sediment is filtered out after a few hours, dry to constant weight, then be placed in Muffle furnace the high temperature at 300~1000 DEG C and roast
1~8h is burnt, high dispersive carrier MgO is made.The KF of certain load capacity and carrier MgO are sufficiently mixed with solid-phase sequencing again, done
It is dry then to be placed in the roasting of Muffle furnace high temperature to constant weight, solid base catalyst KF/MgO is made.
Embodiment 1
148.2g n-butanols and 1.9g catalyst KF/MgO are added in the reactor that volume is 2L, closed stirring, used
N2Air in kettle is displaced, heat temperature raising, when temperature reaches 110 DEG C, continues to be passed through expoxy propane 38.7g into reactor,
Reacting kettle inner pressure is 0.20~0.50MPa, and reaction raw materials mol ratio is n-butanol：Expoxy propane=3:1, expoxy propane conversion
Rate is 75.84%, and propandiol butyl ether yield is 64.65%.
Embodiment 2
148.2g n-butanols and 1.9g catalyst KF/MgO are added in the reactor that volume is 2L, closed stirring, used
N2Air in kettle is displaced, heat temperature raising, when temperature reaches 120 DEG C, continues to be passed through expoxy propane 38.7g into reactor,
Reacting kettle inner pressure is 0.20~0.50MPa, and reaction raw materials mol ratio is n-butanol：Expoxy propane=3:1, expoxy propane conversion
Rate is 81.80%, and propandiol butyl ether yield is 67.79%.
Embodiment 3
148.2g n-butanols and 1.9g catalyst KF/MgO are added in the reactor that volume is 2L, closed stirring, used
N2Air in kettle is displaced, heat temperature raising, when temperature reaches 130 DEG C, continues to be passed through expoxy propane 38.7g into reactor,
Reacting kettle inner pressure is 0.20~0.50MPa, and reaction raw materials mol ratio is n-butanol：Expoxy propane=3:1, expoxy propane conversion
Rate is 85.02%, and propandiol butyl ether yield is 69.73%.
Embodiment 4
148.2g n-butanols and 1.9g catalyst KF/MgO are added in the reactor that volume is 2L, closed stirring, used
N2Air in kettle is displaced, heat temperature raising, when temperature reaches 140 DEG C, continues to be passed through expoxy propane 38.7g into reactor,
Reacting kettle inner pressure is 0.20~0.50MPa, and reaction raw materials mol ratio is n-butanol：Expoxy propane=3:1, expoxy propane conversion
Rate is 82.53%, and propandiol butyl ether yield is 68.14%.
Embodiment 5
148.2g n-butanols and 0.9g catalyst KF/MgO are added in the reactor that volume is 2L, closed stirring, used
N2Air in kettle is displaced, heat temperature raising, when temperature reaches 130 DEG C, continues to be passed through expoxy propane 38.7g into reactor,
Reacting kettle inner pressure is 0.20~0.50MPa, and reaction temperature is constant at 130 DEG C, and reaction raw materials mol ratio is n-butanol：Epoxy third
Alkane=3:1, wherein described catalyst amount is the 0.5% of reactant gross mass.Epoxypropane conversion rate is 77.16%, third
Glycol butyl ether yield is 64.78%.
Embodiment 6
148.2g n-butanols and 2.8g catalyst KF/MgO are added in the reactor that volume is 2L, closed stirring, used
N2Air in kettle is displaced, heat temperature raising, when temperature reaches 130 DEG C, continues to be passed through expoxy propane 38.7g into reactor,
Reacting kettle inner pressure is 0.20~0.50MPa, and reaction temperature is constant at 130 DEG C, and reaction raw materials mol ratio is n-butanol：Epoxy third
Alkane=3:1, wherein described catalyst amount is the 1.5% of reactant gross mass.Epoxypropane conversion rate is 95.46%, third
Glycol butyl ether yield is 76.89%.
Embodiment 7
148.2g n-butanols and 3.7g catalyst KF/MgO are added in the reactor that volume is 2L, closed stirring, used
N2Air in kettle is displaced, heat temperature raising, when temperature reaches 130 DEG C, continues to be passed through expoxy propane 38.7g into reactor,
Reacting kettle inner pressure is 0.20~0.50MPa, and reaction temperature is constant at 130 DEG C, and reaction raw materials mol ratio is n-butanol：Epoxy third
Alkane=3:1, wherein described catalyst amount is the 2.0% of reactant gross mass.Epoxypropane conversion rate is 92.01%, third
Glycol butyl ether yield is 75.37%.
Embodiment 8
148.2g n-butanols and 3.1g catalyst KF/MgO are added in the reactor that volume is 2L, closed stirring, used
N2Air in kettle is displaced, heat temperature raising, when temperature reaches 130 DEG C, continues to be passed through expoxy propane 59.5g into reactor,
Reacting kettle inner pressure is 0.20~0.50MPa, and reaction temperature is constant at 130 DEG C, wherein described reaction raw materials mol ratio is just
Butanol：Expoxy propane=2:1.Epoxypropane conversion rate is 91.88%, and propandiol butyl ether yield is 68.23%.
Embodiment 9
222.3g n-butanols and 4.0g catalyst KF/MgO are added in the reactor that volume is 2L, closed stirring, used
N2Air in kettle is displaced, heat temperature raising, when temperature reaches 130 DEG C, continues to be passed through expoxy propane 46.6g into reactor,
Reacting kettle inner pressure is 0.20~0.50MPa, and reaction temperature is constant at 130 DEG C, wherein described reaction raw materials mol ratio is just
Butanol：Expoxy propane=4:1.Epoxypropane conversion rate is 98.83%, and propandiol butyl ether yield is 82.41%.
Embodiment 10
222.3g n-butanols and 3.8g catalyst KF/MgO are added in the reactor that volume is 2L, closed stirring, used
N2Air in kettle is displaced, heat temperature raising, when temperature reaches 130 DEG C, continues to be passed through expoxy propane 37.0g into reactor,
Reacting kettle inner pressure is 0.20~0.50MPa, and reaction temperature is constant at 130 DEG C, wherein described reaction raw materials mol ratio is just
Butanol：Expoxy propane=5:1.Epoxypropane conversion rate is 99.03%, and propandiol butyl ether yield is 83.12%.
Embodiment 11
Catalyst KF/MgO once will have been used to be added to volume as 2L's in 222.4g n-butanols and 4.0g examples 9
In reactor, closed stirring, N is used2Air in kettle is displaced, heat temperature raising, when temperature reaches 130 DEG C, is continued to reactor
In be passed through expoxy propane 46.6g, reacting kettle inner pressure is 0.20~0.50MPa, and reaction temperature is constant at 130 DEG C, wherein described
Reaction raw materials mol ratio be n-butanol：Expoxy propane=4:1.Epoxypropane conversion rate is 96.39%, propandiol butyl ether yield
For 80.23%.
Embodiment 12
It is 2L that the catalyst KF/MgO for having used twice in 222.4g n-butanols and 4.0g examples 11 is added into volume
Reactor in, closed stirring, use N2Air in kettle is displaced, heat temperature raising, when temperature reaches 130 DEG C, is continued to reaction
Expoxy propane 46.6g is passed through in kettle, reacting kettle inner pressure is 0.20~0.50MPa, and reaction temperature is constant at 130 DEG C, wherein institute
The reaction raw materials mol ratio stated is n-butanol：Expoxy propane=4:1.Epoxypropane conversion rate is 91.57%, propandiol butyl ether production
Rate is 77.41%.
Embodiment 13
It is 2L that the catalyst KF/MgO for having used three times in 222.4g n-butanols and 4.0g examples 12 is added into volume
Reactor in, closed stirring, use N2Air in kettle is displaced, heat temperature raising, when temperature reaches 130 DEG C, is continued to reaction
Expoxy propane 46.6g is passed through in kettle, reacting kettle inner pressure is 0.20~0.50MPa, and reaction temperature is constant at 130 DEG C, wherein institute
The reaction raw materials mol ratio stated is n-butanol：Expoxy propane=4:1.Epoxypropane conversion rate is 90.86%, propandiol butyl ether production
Rate is 76.13%.
Comparative example 1
222.1g n-butanols and 4.0g catalyst ns aOH are added in the reactor that volume is 2L, closed stirring, use N2
Air in kettle is displaced, heat temperature raising, when temperature reaches 130 DEG C, continues to be passed through expoxy propane 46.6g into reactor, instead
It is 0.20~0.50MPa to answer pressure in kettle, and reaction temperature is constant at 130 DEG C, wherein described reaction raw materials mol ratio is positive fourth
Alcohol：Expoxy propane=4:1.Epoxypropane conversion rate is 95.14%, and propandiol butyl ether yield is 69.37%.
From comparative example 1 and embodiment 9, under identical reaction conditions, the catalyst of system is uploaded with industry
After NaOH catalytic reactions, the conversion ratio of expoxy propane and the yield of propandiol butyl ether are respectively 95.14% and 69.37%, all low
The alcohol butyl ether yield 82.41% of epoxypropane conversion rate 98.83% after solid base catalyst KF/MgO catalytic reactions
Comparative example 2
148.2g n-butanols and 1.9g are used into catalyst KF/MgO (the KF loads that commonly commercially available MgO is prepared for carrier
Amount be MgO mass 30%) be added to volume be 2L reactor in, closed stirring, use N2Air in kettle is displaced, heating rises
Temperature, when temperature reaches 120 DEG C, continuing to be passed through expoxy propane 38.7g into reactor, reacting kettle inner pressure is 0.20~
0.50MPa, reaction raw materials mol ratio are n-butanol：Expoxy propane=3:1, epoxypropane conversion rate 76.25%, propane diols fourth
Ether yield is 41.48%.
By comparative example 2 and embodiment 2, after the catalyst reaction directly prepared by the use of commercially available MgO as carrier,
Epoxypropane conversion rate and propandiol butyl ether yield are respectively the 76.25% and 41.48% high dispersive MgO carriers for being below preparing
The catalyst epoxypropane conversion rate 81.80% and propandiol butyl ether yield 67.79% after catalytic reaction under the same conditions.By
TEM figures (b) are as can be seen that the high dispersive MgO prepared does the solid base catalyst KF/MgO of carrier preparation microstructure more
Loose, hole is more, so showing higher catalytic activity.And solid base catalyst KF/ prepared by commercially available MgO loads KF
MgO (figure (a)) microstructure is closer, and hole is less, so the catalytic activity shown is relatively low.
Comparative example 3
It is 2L that 148.2g n-butanols and 1.9g catalyst MgO (MgO be prepare high dispersive carrier) are added into volume
In reactor, closed stirring, N is used2Air in kettle is displaced, heat temperature raising, when temperature reaches 120 DEG C, is continued to reactor
In be passed through expoxy propane 38.7g, reacting kettle inner pressure is 0.20~0.50MPa, and reaction temperature is constant at 120 DEG C, wherein described
Reaction raw materials mol ratio be n-butanol：Expoxy propane=3:1.Epoxypropane conversion rate is 24.32%, propandiol butyl ether yield
For 14.57%.
It can be seen from comparative example 3 and embodiment 2 under identical reaction conditions, directly by the use of homemade MgO as
After catalyst reaction, the conversion ratio of expoxy propane and the yield of propandiol butyl ether are respectively 24.32% and 14.57%, all
Far below the catalyst KF/MgO for having loaded KF.By XRD it can be found that catalyst KF/MgO is in addition to MgO characteristic diffraction peak,
Also substantially there is new crystalline phase K2MgF4Diffraction maximum, this is due to KF and there occurs reaction 4KF+MgO → K by carrier MgO2O+
K2MgF4.Illustrate exactly K2MgF4Synergy improve the catalytic activity of catalyst.
It is complete by above-mentioned description, relevant staff using the above-mentioned desirable embodiment according to the present invention as enlightenment
Various changes and amendments can be carried out without departing from the scope of the technological thought of the present invention' entirely.The technology of this invention
Property scope is not limited to the content on specification, it is necessary to determines its technical scope according to right.
Claims (5)
- A kind of 1. method of synthesizing propanediol butyl ether, it is characterised in that：N-butanol, KF/MgO solid base catalysts are added to instead Answer in kettle, sealing stirring, use N2Air in kettle is displaced, is heated to design temperature, is slowly introducing expoxy propane, and control Reactor temperature substantially constant, control reacting kettle inner pressure cool and discharged after terminating, obtain in 0.20~0.50MPa, reaction To propandiol butyl ether product.
- A kind of 2. method of synthesizing propanediol butyl ether according to claims 1, it is characterised in that：Raw material molar ratio For n-butanol：Expoxy propane=1~5:1, reaction temperature is 110~140 DEG C, and reaction pressure is 0.20~0.50MPa, KF/MgO Solid base catalyst mass percent is the 0.5~2% of raw material n-butanol and expoxy propane gross mass.
- A kind of 3. method of synthesizing propanediol butyl ether according to claim 1 or 2, it is characterised in that：The KF/MgO consolidates The preparation method of body base catalyst is as follows：Quantitative magnesium chloride solution is reacted with precipitating reagent sodium hydroxide, sodium carbonate, control technique Condition filters out sediment in 40~100 DEG C of 1~24h of crystallization after a few hours, dry to constant weight, then be placed in Muffle furnace in 300 1~8h of high-temperature roasting at~1000 DEG C, high dispersive carrier is made.Again by the KF of certain load capacity and carrier MgO solid-phase grindings Method is sufficiently mixed, and is dried to constant weight, then is placed in Muffle furnace 1~8h of high-temperature roasting at 300~1000 DEG C, and obtained solid base is urged Agent KF/MgO.
- A kind of 4. preparation method of synthesizing propanediol butyl ether catalyst according to claim 3, it is characterised in that：Prepare and carry Precipitating reagent used in body MgO is that mol ratio is 1:1 sodium hydroxide and sodium carbonate, KF load capacity are the 30% of MgO mass.
- A kind of 5. method of synthesizing propanediol butyl ether according to claims 1 or 2, it is characterised in that：Material molar ratio For n-butanol：Expoxy propane=4:1；Reaction temperature is 130 DEG C；Catalyst quality percentage dosage is reactant n-butanol and ring The 1.5% of Ethylene Oxide gross mass.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108620055A (en) * | 2018-06-29 | 2018-10-09 | 江苏华伦化工有限公司 | It is used to prepare solid super basic catalyst and its application of dihydroxypropane single-ether |
| CN114539038A (en) * | 2022-03-17 | 2022-05-27 | 南京嘉言新材料科技有限公司 | Preparation method of propylene glycol monobutyl ether |
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| CN1597649A (en) * | 2004-08-04 | 2005-03-23 | 河北工业大学 | Method of synthesizing 2-hydroxyproply method ether using loading type aldaline catalyst |
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| CN108620055A (en) * | 2018-06-29 | 2018-10-09 | 江苏华伦化工有限公司 | It is used to prepare solid super basic catalyst and its application of dihydroxypropane single-ether |
| CN114539038A (en) * | 2022-03-17 | 2022-05-27 | 南京嘉言新材料科技有限公司 | Preparation method of propylene glycol monobutyl ether |
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Application publication date: 20180119 |