CN101250094A - Method for preparing 1-methoxy-2-propanol - Google Patents
Method for preparing 1-methoxy-2-propanol Download PDFInfo
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- CN101250094A CN101250094A CNA2008100813139A CN200810081313A CN101250094A CN 101250094 A CN101250094 A CN 101250094A CN A2008100813139 A CNA2008100813139 A CN A2008100813139A CN 200810081313 A CN200810081313 A CN 200810081313A CN 101250094 A CN101250094 A CN 101250094A
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- propylene oxide
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- methoxyl group
- tertiary amine
- propyl alcohol
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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
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
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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
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
- C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation
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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
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/46—Use of additives, e.g. for stabilisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A method for preparing 1-methoxy-2-propanol is disclosed, including high propylene oxide conversion rate and high 1-methoxy-2-propanol selectivity and capable of reducing content of by-product. The method comprises the reaction procedure of reacting methanol with propylene oxide at 90 to 110 DEG C to obtain reaction crude liquid in the presence of tertiary amine, and distillation procedure of distilling the reaction crude liquid to prepare1-methoxy-2-propanol. In the method, methanol, propylene oxide and tertiary amine are continuously supplied to a tower type reactor whose interior includes a temperature control unit composed by helical pipes of communicable heat conducting medium, the obtained reaction crude liquid is consecutively distilled by using a filling tower which is full of regular fillings in order to prepare 1-methoxy-2-propanol.
Description
Technical field
The present invention relates to the preparation method of 1-methoxyl group-2-propyl alcohol, this method has high propylene oxide transformation efficiency, and prepares 1-methoxyl group-2-propyl alcohol with high selectivity.
Background technology
1-methoxyl group-2-propyl alcohol is identical with other glycol ethers, the resin solvent that can be used as coating, printing ink, also can be used as the dyeing coupler of brake solution (Block レ one キ oil), textiles, leathercraft, be to be different from the common useful industrial goods with marketability with solvent.
Common method as preparation 1-alkoxyl group-2-propyl alcohol, known preparation method is in the presence of catalyzer, make the method for alcohol and propylene oxide reaction, but often generate higher-boiling compounds such as 2-alkoxyl group-1 propyl alcohol and dipropylene glycol monoalky lether as by product.For example: when alcohol is methyl alcohol, with 1-methoxyl group-2-propyl alcohol and separation of by-products, in order to reduce content of by-products, distill sometimes, but 1-methoxyl group-2-propyl alcohol is close with 2-methoxyl group-1-propyl alcohol boiling point, both are difficult to separate fully.For example: in known 1-methoxyl group-2-propyl alcohol, be mixed with 2-methoxyl group-1-propyl alcohol of about 300ppm as the industrial goods use.Known 2-methoxyl group-1-propyl alcohol has very strong toxicity (genotoxicity etc.), and the content that reduces 2-methoxyl group-1-propyl alcohol in the industry use goods as far as possible is very important problem.
The spy opens in the clear 56-15229 communique (patent documentation 1), has put down in writing under the condition that tertiary amine exists, and alcohol is about more than 2 with respect to the mol ratio of propylene oxide, the method for low-grade monobasic alcohol and propylene oxide 1-alkoxyl group-2-propyl alcohol.
Among this preparation method, methyl alcohol and propylene oxide are reacted under the condition that tertiary amine exists, can make 1-methoxyl group-2-propyl alcohol.This method is separated 1-methoxyl group-2-propyl alcohol with by product (2-methoxyl group-higher-boiling compounds such as 1-propyl alcohol etc.), in order to reduce by product (particularly 2-methoxyl group-1-propyl alcohol) though content distill, but, be difficult to reach high efficiency separation by distillation as previously mentioned because 1-methoxyl group-2-propyl alcohol is close with 2-methoxyl group-1-propyl alcohol boiling point.Although can increase distillation efficiency by increase reflux ratio, increase distillation tower height, cost increases, and is impracticable.
Therefore, under distillation procedure condition commonly used, make 1-methoxyl group-2-propyl alcohol and by product high efficiency separation, other method is necessary.Method as other illustrates, and improves the transformation efficiency of propylene oxide and the selection rate of 1-methoxyl group-2-propyl alcohol, reduces content of by-products in advance, and it is effective that distillating method etc. are considered to.Patent documentation 1 record makes methyl alcohol and propylene oxide in reaction below 80 ℃, distills, and the transformation efficiency of propylene oxide is 93.2-98.8%, and selection rate that can 92.9-96.5% prepares 1-methoxyl group-2-propyl alcohol.
Preparing in the method for glycol ether of Te Kaiping 7-206744 communique (patent documentation 2) record by oxyalkylene and alcohol, under the condition that tertiary amine exists, methyl alcohol and propylene oxide can be that 97-100%, selection rate 94-95% prepare 1-methoxyl group-2-propyl alcohol with the transformation efficiency of propylene oxide 80 ℃, 100 ℃, 120 ℃ reactions.But, promptly use the method for the document, selection rate also is inadequate.
As mentioned above, 1-methoxyl group-2-propyl alcohol is as the widely used while of industrial goods, because 2-methoxyl group-1-propyl alcohol has very strong toxicity, therefore further reduce the content of by product (particularly 2-methoxyl group-1-propyl alcohol), it is very necessary in other words further improving the transformation efficiency of propylene oxide and the selection rate of 1-methoxyl group-2-propyl alcohol.
[patent documentation 1] spy opens clear 56-15229 communique (claim, embodiment)
[patent documentation 2] spy opens flat 7-206744 communique (claim, embodiment)
The content of invention
The problem that invention will solve
Therefore, the object of the present invention is to provide a kind of method for preparing 1-methoxyl group-2-propyl alcohol with high conversion and high selectivity.
Another object of the present invention is for providing a kind of method for preparing 1-methoxyl group-2-propyl alcohol that reduces poisonous by-products content.
Even another purpose of the present invention is for providing a kind of method that also can low-cost high-efficiency prepares 1-methoxyl group-2-propyl alcohol with industrial-scale production.
The method of dealing with problems
Present inventors through research with keen determination, found that methyl alcohol and propylene oxide react for reaching above-mentioned purpose under specific temperature, distillation, can optionally prepare 1-methoxyl group-2-propyl alcohol, prepare the very low 1-methoxyl group-2-propyl alcohol of poisonous content of by-products, thereby finished the present invention.
Be that method of the present invention is included under the condition of tertiary amine existence, make methyl alcohol and propylene oxide obtain reacting the reaction process of thick liquid, and will react thick liquid distillatory distillation process, preparation 1-methoxyl group-2-propyl alcohol 90-110 ℃ of reaction.
In this method, methyl alcohol and propylene oxide can be the doubly reaction of the ratio about mole of 2-10 of propylene oxide with methyl alcohol.In addition, the ratio of tertiary amine can 0.1-10 weight % for methyl alcohol, propylene oxide and tertiary amine total amount about.
In addition, this method can be used the tower reactor, and this tower inside reactor can be provided with the temperature control unit that is made of helical coil of negotiable heat-transfer medium.In the method for the present invention, can in above-mentioned reactor, supply with methyl alcohol, propylene oxide and tertiary amine continuously, the thick liquid of reaction that continuous still battery is flowed out by reactor.In addition, can a plurality of reactors in series (array) be provided with.The thick liquid of reaction that reaction process can be obtained in addition, distills by the packed tower that is filled with regular packing.
The invention effect
Among the present invention, owing under the condition that tertiary amine exists, methyl alcohol and propylene oxide are reacted under specific temperature, can improve the selection rate of the transformation efficiency and the 1-methoxyl group-2-propyl alcohol of propylene oxide, reduce content, optionally prepare 1-methoxyl group-2-propyl alcohol with strong toxic by-products.In addition, owing to can suppress the generation of high boiling point by-products produced (2-methoxyl group-1-propyl alcohol and dipropylene glycol monomethyl ether etc.), can under commonly used and gentle condition, carry out distillation procedure, expeditiously with 1-methoxyl group-2-propyl alcohol and separation of by-products.Therefore, even also can low-cost high-efficiency ground preparation 1-methoxyl group-2-propyl alcohol with industrial-scale production.
Embodiment
The present invention makes methyl alcohol and propylene oxide react the reaction process that obtains reacting thick liquid under specific temperature, and will react thick liquid distillatory distillation process through under the condition that exists at tertiary amine, preparation 1-methoxyl group-2-propyl alcohol.
Reaction process
The reactor of reaction process can use reactor commonly used, illustrates tower, grooved, cast etc.In addition, but also can use the flow reactor of operate continuously, but can also use the batch reactor of periodical operation (or semi-batch operation).In addition, the reactor of use preferably uses has the efficient temperature control unit, and the temperature variation that reaction causes can be alleviated in this unit, keeps the temperature of reaction of hope.As temperature control unit, can give an example, negotiable heat-transfer medium (for example: water, water vapour, wet goods), by the unit (coil pipe (コ イ Le) shape temperature control unit) that spirrillum, pipe such as cylindric constitute, can hold unit (sleeve pipe) that reactor and above-mentioned heat-transfer medium can circulate etc. between this unit and reactor.The present invention considers from the angle of temperature controlling efficiency, production efficiency, preferably uses tower reactor (reaction tower).Particularly also can use inside reactor (for example: tower reactor (reaction tower) temperature control unit that constitutes by the helical coil of negotiable heat-transfer medium) to have temperature control unit.
The number of reactor has no particular limits, and can be single reactor, in order to obtain resultant with high reaction yield, also a plurality of (base) reactor (more than 2) can be used in combination.Consider that from reaction efficiency, equipment and energy expenditure equal angles reactor is 2-3 (especially 2) usually.A plurality of reactors can configured in series, can in parallel dispose, also can connect and combining and configuring in parallel.Usually, a plurality of reactors in series configurations.In addition, when using a plurality of reactor, preferably in a plurality of reactors, have at least in one (especially supplying with first reactor of the composition that responds) and have coil-like temperature control unit.
In addition, in order to improve reaction efficiency (reaction yield), can use in case of necessity and fill Packed tower reactor (reaction tower).As filler, can give an example, bohr ring, Raschig ring (ラ シ ヒ リ Application ゲ), Lessing ring saddle fillers such as annular packing, saddle (サ De Le), McMahon packing such as (レ Star シ Application グ リ Application ゲ), ball filler, Suhl longevity (Sulzer packing, ス Le ザ one パ Star キ Application) are waited the filler of other shape etc.These fillers can use separately also and can be used in combination.The preferred annular packing of filler (for example: Raschig ring etc.).
The ratio of methyl alcohol and propylene oxide, with respect to propylene oxide, for example: quantity of methyl alcohol is (for example: 2-10 times mole) more than 2 times of moles, preferably 3-9 times mole, more preferably 4-8 times mole (particularly 5-7 times mole).Dipropylene glycol monomethyl ether etc.) methyl alcohol is with respect to the ratio of propylene oxide hour, and the high order affixture that has a propylene oxide (for example: high boiling point by-products content situation about increasing such as.
As tertiary amine, can use aliphatic tertiary amine, aromatic nitrile base, heterocycle tertiary amine etc. usually.As aliphatic tertiary amine, can give an example trialkylamines such as Trimethylamine 99, triethylamine, Tri-n-Propylamine (three C especially
1-6Alkylamine), dialkyl group alkylamine such as dimethylethyl amine (two C especially
1-6Alkyl C
1-6Alkylamine).As aromatic nitrile base, can give an example N, accelerine, N, N-alkyl-N-alkyl benzene amines such as N-Diethyl Aniline (N-C especially
1-6Alkyl-N-C
1-6Alkyl benzene amine) etc.As the heterocycle tertiary amine, can give an example pyridine, picoline, quinoline etc.These tertiary amines may be used singly or in combination of two or more.
The present invention preferably uses than 1-methoxyl group-low-boiling tertiary amine of 2-propyl alcohol.For example: can use three C such as Trimethylamine 99, triethylamine, dimethylethyl amine
1-3Alkylamine, pyridine etc.Particularly preferred tertiary amine is a triethylamine.
The ratio of tertiary amine can 0.1-10 weight % for methyl alcohol, propylene oxide and tertiary amine total amount about, be preferably 0.2-7 weight %, more preferably 0.5-5 weight %, preferred especially 0.7-2 weight % is (for example: 0.8-1.5 weight %).
Methyl alcohol, propylene oxide and tertiary amine are in above-mentioned reactor, and intermittently the mode of (or semi-batch) is supplied with, but consider to adopt continuously usually to supply with from industrial angle.The speed that methyl alcohol, propylene oxide and tertiary amine are supplied with to reactor, linear speed can be preferably 2.1-4.6m/h for about 2.0-5.0m/h, more preferably about 2.2-4.2m/h.
Method of the present invention under the condition that tertiary amine exists, makes methyl alcohol and propylene oxide at 90-110 ℃, and preferred 95-110 ℃, more preferably 95-105 ℃ of reaction.Than the lower thermotonus of said temperature scope the time, the low tendency of propylene oxide transformation efficiency appears.On the other hand, than the higher thermotonus of said temperature scope the time, the tendency that by product 2-methoxyl group-1-propyl alcohol and dipropylene glycol monomethyl ether content increase appears.
For with the propylene oxide high conversion, above-mentioned by product low levels prepares 1-methoxyl group-2-propyl alcohol, preferably temperature of reaction is controlled at certain temperature range (90-110 ℃), so control reaction temperature (temperature of reaction system) is effective as mentioned above.Aspect control reaction temperature, can use the said temperature control unit, especially above-mentioned coil-like temperature control unit.Illustrate, when being the situation of coil-like temperature control unit (the especially temperature control unit that constitutes by helical coil), heat-transfer medium circulates in above-mentioned coil-like temperature control unit, can improve heat transfer efficiency, control reaction temperature that can simple and effective.In addition, when successive supply response material reacts in reactor, change that common reaction system is formed and the temperature variation that causes because of reaction become big, be difficult to control and keep temperature of reaction (temperature of reaction system), even but in this case, heat-transfer medium (especially water) circulation in above-mentioned coil-like temperature control unit (the especially temperature control unit that is made of helical coil) can be easy to controlled temperature, temperature of reaction (temperature of reaction system) can be maintained specified temp.As above-mentioned heat-transfer medium, can use oil (silicone oil etc.) etc., can make water usually.The temperature of above-mentioned medium (especially water) can be selected according to temperature of reaction, and preferred temperature is lower than temperature of reaction.For example: the difference of the temperature of above-mentioned medium and desired temperature of reaction can be 5-30 ℃, preferred 7-25 ℃, and more preferably 10-20 ℃.The temperature of above-mentioned medium and desired temperature of reaction difference are excessive, have the problem that is difficult to temperature maintenance constant (constant substantially) temperature of reaction system.
The pressure of reaction system was defined as by the forming and the air pressure sum of the vapour pressure of temperature of reaction decision and the rare gas element (nitrogen etc.) of press seal (or being pressed into) for reaction safety is carried out of reactive material, and can be 1～20kg/cm
2( 1.0 * 10 for G
5～20 * 10
5Pa) about, preferred 2～15kg/cm
2( 2.0 * 10 for G
5～15 * 10
5Pa) about, more preferably 3～10kg/cm
2( 3.0 * 10 for G
5～10 * 10
5Pa) about.
Distillation process
Distillation process is the thick liquid distillation of reaction that reaction process is obtained.
Distillation can be used device commonly used (distillation tower) with device (water distilling apparatus), for example: column plate type tower (perforated plate column, bubble-plate column etc.), filling tower etc.The present invention preferably uses packed tower in order to reduce the pressure-losses in the device.As the filler of packed tower, can use irregular filler (random packing), but, improve distillation efficiency, preferred service regulations filler for the pressure-losses in the further restraining device.As regular packing, can use widely used regular packing (structured packing), can give an example, by formations such as metals such as titanium, zirconium or its alloy, stainless steel (austenitic stainless steel etc.), potteries.In addition, regular packing can be sheet (tabular), mesh-like (netted), palisade (reticulation) etc.These regular packings can be used alone or in combination of two or more.
Because distillation tower is along with the increase of distilling tray number (number of theoretical plate), separation performance improves, and preferably using stage number (number of theoretical plate) is (for example: 30-60, preferred 32-55, more preferably 35-50) more than 30.In addition, the number of distillation tower has no particular limits, and can be one also can be that a plurality of (more than 2) are used in combination, and considers from reaction yield, equipment and energy expenditure equal angles, can use 1-2 (especially 2) distillation tower usually.In order to improve distillation efficiency (separation efficiency), preferably carry out the multistage distillation in addition.Usually, consider, carry out the distillation of 2-3 (especially 2 stages) stage from the angle of the target product rate of recovery.Each stage uses the number of distillation tower can be the same or different.Illustrate, can use 2 distillation towers, use a distillation tower later on from subordinate phase in the fs.For example the present invention can be in the distillation procedure of fs, distill out low boiling point component (unreacted methanol, tertiary amine etc.), in the distillation procedure of subordinate phase, remove high boiling point composition (by products such as 2-methoxyl group-1-propyl alcohol, dipropylene glycol monomethyl ether etc.).Fs distillation procedure distilled methyl alcohol and tertiary amine can recycle as reactive material once more in addition.
Above-mentioned reaction process and distillation process can carry out separately, but consider from the angle of industrial production, carry out two operations more favourable continuously.If above-mentioned reaction process and distillation process are carried out continuously, can to reach 99 moles of % above (for example: about 99.1-99.9 mole % for the transformation efficiency of propylene oxide during preparation 1-methoxyl group-2-propyl alcohol, preferred 99.2-99.8 mole %, more preferably 99.3-99.7 mole % is particularly about 99.4-99.6 mole %).And, the selection rate of 1-methoxyl group-2-propyl alcohol (is benchmark with the propylene oxide) is that 99.9 moles of % are above (for example: 99.910-99.999 mole %, preferred 99.930-99.995 mole %, more preferably 99.950-99.992 mole % is about preferred especially 99.960-99.990 mole %).In addition, the selection rate of 2-methoxyl group-1-propyl alcohol (is benchmark with the propylene oxide) is about 0.001-0.03 mole % (for example: about 0.002-0.028 mole %, 0.003-0.026 mole % particularly).By method of the present invention, can prepare the very low 1-methoxyl group-2-propyl alcohol of strong toxicity 2-methoxyl group-1-propyl alcohol content.
Embodiment
The present invention is described in detail by the following examples, but the present invention is not limited to these embodiment.
Embodiment and comparative example use following reactive material, reactor, water distilling apparatus.
Reactive material: methyl alcohol: 3462kg/h (108.1kmol/h)
Propylene oxide: 1046kg/h (18.0kmol/h)
Triethylamine: 45.5kg/h (0.45kmol/h)
[methyl alcohol/propylene oxide (mol ratio)=6, triethylamine concentration=1.0 weight %]
Reactor 1: inside is filled with the tower reactor (Mitsui shipbuilding (strain) system, internal diameter 1450mm φ, high 14698mm) of Raschig ring
Reactor 2: inside is filled with the tower reactor (Mitsui shipbuilding (strain) system, internal diameter 500mm φ, high 15708mm) of Raschig ring
Distillation tower 1: regular packing, Sumimoto Heavy Plant Engineering (living in heavy プ ラ Application ト エ Application ジ ニ ア リ Application グ (strain)) system, Sumitomo SFLOW 250MY) with the highly-filled packed tower of 20200mm (Mitsui shipbuilding (strain) system, internal diameter 1100mm φ, high 30948mm, number of theoretical plate 45).
Distillation tower 2: bubble-plate column (Mitsui shipbuilding (strain) system, internal diameter 1100mm φ, high 3094mm, number of actual plates 60, number of theoretical plate 36).
In addition, the selection rate of the transformation efficiency of propylene oxide and each composition is asked calculation in order to following method in embodiment and the comparative example.
[transformation efficiency]
Use the gas chromatographic analysis reaction product, the content of propylene oxide in the assaying reaction liquid, itself and the transformation efficiency of relatively trying to achieve propylene oxide that reacts preceding propylene oxide content.Promptly the content (mole number) of propylene oxide is C before the reaction, and the content of propylene oxide (mole number) is C ' in the reaction solution, transformation efficiency (mole %)=[1-(C '/C)] * 100.
[each components selection rate]
Each components selection rate, for example the selection rate of 1-methoxyl group-2-propyl alcohol is used the gas chromatographic analysis reaction product, the content of 1-methoxyl group-2-propyl alcohol in the assaying reaction liquid, its ratio with the reaction product total amount is the selection rate of 1-methoxyl group-2-propyl alcohol.The content (mole number) that is 1-methoxyl group-2-propyl alcohol in the reaction solution is represented with S, the total amount of reaction product (total mole number) S ' expression, and selection rate (mole %)=(S/S ') * 100.In addition, other component is also asked calculation with mode of the same race.
[embodiment 1]
Reactive material is fed in the reactor 1 continuously, and this reactor 1 inside has the temperature control unit that is made of helical coil of negotiable heat-transfer medium, and feeds liquid by reactor 1 to reactor 2, reacts.In addition, in the reactor 1, in said units, feed 80 ℃ water, the temperature of reaction system is controlled at 97 ℃, react.The transformation efficiency of propylene oxide is 99.6 moles of % in the thick liquid of the reaction that obtains.In addition, 1-methoxyl group-2-propyl alcohol, 2-methoxyl group-1-propyl alcohol, dipropylene glycol monomethyl ether and other components selection rate (is benchmark with the propylene oxide) are respectively 87.7 moles of %, 6.3 moles of %, 2.3 moles of %, 3.7 moles of %.To react thick liquid then in reflux ratio 3.2, distillate under the condition of rate 86.5% with distillation tower 1 distillation.Try to achieve transformation efficiency and each components selection rate (is benchmark with the propylene oxide) of propylene oxide in the distillation gained refined liquid.
[embodiment 2]
All the other carry out according to embodiment 1 same method except that replacing distillation tower 1 use distillation tower 2, try to achieve transformation efficiency and each components selection rate (is benchmark with the propylene oxide) of propylene oxide in the distillation gained refined liquid.
[comparative example 1]
React by method similarly to Example 1 except not controlling the temperature of reaction system.Gained is reacted thick liquid to be distilled with distillation tower 2.Try to achieve transformation efficiency and each components selection rate (is benchmark with the propylene oxide) of propylene oxide in the distillation gained refined liquid.
[comparative example 2]
With reactive material by reacting with the same method of comparative example 1.Try to achieve transformation efficiency and each components selection rate (is benchmark with the propylene oxide) of propylene oxide in the thick liquid of reaction.
[comparative example 3]
React by method similarly to Example 1 except not controlling the temperature of reaction system.Try to achieve transformation efficiency and each components selection rate (is benchmark with the propylene oxide) of propylene oxide in the thick liquid of reaction.
The result of embodiment and comparative example is as shown in table 1.In addition, " transformation efficiency " in the table represented with the transformation efficiency of propylene oxide, and " 1-MMPG ", " 2-MMPG ", " high boiling component ", " other " are represented the selection rate (is benchmark with the propylene oxide) of 1-methoxyl group-2-propyl alcohol, 2-methoxyl group-1-propyl alcohol, dipropylene glycol monomethyl ether and other composition respectively.
[table 1]
| Embodiment 1 | Embodiment 2 | Comparative example 1 | Comparative example 2 | Comparative example 3 | |
| Temperature of reaction (℃) | 97 | 97 | 135 | 97 | 135 |
| Transformation efficiency (mol%) | 99.6 | 99.6 | 99.4 | 99.6 | 99.4 |
| 1-MMPG(mol％) | 99.991 | 99.968 | 99.949 | 87.7 | 85.6 |
| 2-MMPG(mol％) | 0.003 | 0.026 | 0.038 | 6.3 | 8.5 |
| High boiling point composition (mol%) | 0.006 | 0.006 | 0.005 | 2.3 | 2.5 |
| Other (mol%) | ＜0.0001 | ＜0.0001 | 0.009 | 3.7 | 3.4 |
As shown in table 1, make above-mentioned reactive material at specific temperature range internal reaction, distillation, the selection rate of the transformation efficiency of propylene oxide and 1-methoxyl group-2-propyl alcohol is very high, can obtain the lower 1-methoxyl group-2-propyl alcohol of by-products content that contains in the more industrial widely used 1-methoxyl group of by-products content-2-propyl alcohol.In addition, in the distillation process, use the packed tower that is filled with regular packing as distillation tower, effect is remarkable.
Industrial applicibility
Method of the present invention, prepare the 1-methoxy-2-propanol even in industrial production, also can reduce the content with strong toxic by-products, resulting 1-methoxy-2-propanol is safe, can be used as the resin solvent of coating, printing ink, also can be used as the industrial goods such as dyeing coupling agent of brake fluid, textile, leathercraft.
Claims (5)
1, prepare the method for 1-methoxyl group-2-propyl alcohol, this method is included under the existence of tertiary amine, makes methyl alcohol and propylene oxide obtain reacting the reaction process of thick liquid 90-110 ℃ of reaction, and will react thick liquid and carry out the distillatory distillation process.
2, the method for claim 1 record, wherein methyl alcohol is 2-10 times of mole of propylene oxide, make methyl alcohol and propylene oxide reaction with this ratio, and the ratio of tertiary amine is the 0.1-10 weight % of methyl alcohol, propylene oxide and tertiary amine total amount.
3, the method for claim 1 record, wherein in the tower reactor, supply with methyl alcohol, propylene oxide and tertiary amine continuously, will be by the thick liquid continuous still battery of the reaction that reactor flows out, described tower inside reactor is provided with the temperature control unit that the helical coil by negotiable heat-transfer medium constitutes.
4, the method for claim 3 record, wherein a plurality of reactors in series settings.
5, the method for claim 1 record wherein in distillation process, is distilled with the filling tower that is filled with regular packing.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP043712/07 | 2007-02-23 | ||
| JP2007043712A JP5127263B2 (en) | 2007-02-23 | 2007-02-23 | Method for producing 1-methoxy-2-propanol |
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| Publication Number | Publication Date |
|---|---|
| CN101250094A true CN101250094A (en) | 2008-08-27 |
| CN101250094B CN101250094B (en) | 2013-02-27 |
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| CN2008100813139A Active CN101250094B (en) | 2007-02-23 | 2008-02-25 | Method for preparing 1-methoxy-2-propanol |
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|---|---|
| JP (1) | JP5127263B2 (en) |
| KR (1) | KR101422850B1 (en) |
| CN (1) | CN101250094B (en) |
| TW (1) | TWI405751B (en) |
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| CN105693482A (en) * | 2014-12-15 | 2016-06-22 | 罗门哈斯电子材料有限责任公司 | Purification method |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5615229A (en) * | 1979-07-17 | 1981-02-14 | Daicel Chem Ind Ltd | Production of alkoxypropanol |
| KR970008589B1 (en) * | 1994-01-11 | 1997-05-27 | 주식회사 유공 | Preparation of glycolether |
| JPH07260342A (en) * | 1994-03-18 | 1995-10-13 | Hitachi Ltd | Packed fractionating tower |
| JP2002338511A (en) * | 2001-05-16 | 2002-11-27 | Kyowa Yuka Co Ltd | Distillation apparatus for propylene glycol monoalkyl ether and method for distilling the same |
-
2007
- 2007-02-23 JP JP2007043712A patent/JP5127263B2/en active Active
-
2008
- 2008-02-18 TW TW097105522A patent/TWI405751B/en active
- 2008-02-22 KR KR1020080016284A patent/KR101422850B1/en active IP Right Grant
- 2008-02-25 CN CN2008100813139A patent/CN101250094B/en active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105693482A (en) * | 2014-12-15 | 2016-06-22 | 罗门哈斯电子材料有限责任公司 | Purification method |
| CN105693482B (en) * | 2014-12-15 | 2020-05-15 | 罗门哈斯电子材料有限责任公司 | Purification method |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5127263B2 (en) | 2013-01-23 |
| KR101422850B1 (en) | 2014-07-24 |
| TWI405751B (en) | 2013-08-21 |
| CN101250094B (en) | 2013-02-27 |
| JP2008208035A (en) | 2008-09-11 |
| TW200848397A (en) | 2008-12-16 |
| KR20080078601A (en) | 2008-08-27 |
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