JPH05345736A - Purification of secondary butanol - Google Patents
Purification of secondary butanolInfo
- Publication number
- JPH05345736A JPH05345736A JP3133313A JP13331391A JPH05345736A JP H05345736 A JPH05345736 A JP H05345736A JP 3133313 A JP3133313 A JP 3133313A JP 13331391 A JP13331391 A JP 13331391A JP H05345736 A JPH05345736 A JP H05345736A
- Authority
- JP
- Japan
- Prior art keywords
- secondary butanol
- butene
- aqueous solution
- butanol
- under
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 238000000746 purification Methods 0.000 title description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000007864 aqueous solution Substances 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 24
- 238000006703 hydration reaction Methods 0.000 claims abstract description 12
- CGFYHILWFSGVJS-UHFFFAOYSA-N silicic acid;trioxotungsten Chemical compound O[Si](O)(O)O.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 CGFYHILWFSGVJS-UHFFFAOYSA-N 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract description 6
- 238000004821 distillation Methods 0.000 abstract description 6
- 239000007788 liquid Substances 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 2
- 238000000605 extraction Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000011964 heteropoly acid Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- 230000036571 hydration Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Classifications
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は第2級ブタノールの精製
法に関し、詳しくは第2級ブタノールの水溶液から高純
度の第2級ブタノールを効率よく分離、精製する方法に
関する。TECHNICAL FIELD The present invention relates to a method for purifying secondary butanol, and more particularly to a method for efficiently separating and purifying highly pure secondary butanol from an aqueous solution of secondary butanol.
【0002】[0002]
【従来の技術及び発明が解決しようとする課題】n−ブ
テンの間接水和による第2級ブタノールの製造法は、硫
酸を用いてn−ブテンの硫酸エステルを形成し、このエ
ステルを加水分解して第2級ブタノールを製造する方法
である。BACKGROUND OF THE INVENTION A process for producing secondary butanol by indirect hydration of n-butene is to use sulfuric acid to form a sulfuric ester of n-butene and hydrolyze the ester. Is a method for producing secondary butanol.
【0003】しかし、この間接水和法は硫酸を用いるた
め、硫酸による製造装置の腐蝕,廃硫酸の処理,廃水処
理等の好ましくない問題が多く、また製造装置が複雑に
なるという問題もあった。However, since this indirect hydration method uses sulfuric acid, there are many unfavorable problems such as corrosion of the production equipment by sulfuric acid, treatment of waste sulfuric acid, wastewater treatment and the like, and the production equipment becomes complicated. .
【0004】一方、n−ブテンの直接水和による第2級
ブタノールの製造法は、気相法と液相法が知られてい
る。気相法には、n−ブテンの転化率が低く、用いる固
体触媒成分の溶出が見られるなど様々な欠点がある。ま
た、液相法はイオン交換樹脂やヘテロポリ酸を触媒とし
て用いる方法が知られている。この液相法には、上記気
相法における欠点は見られないが、第2級ブタノールが
比較的低濃度の水溶液として得られるので、この水溶液
から第2級ブタノールを分離し、精製する必要があっ
た。On the other hand, as a method for producing secondary butanol by direct hydration of n-butene, a vapor phase method and a liquid phase method are known. The gas phase method has various drawbacks such as a low conversion rate of n-butene and elution of the solid catalyst component used. Further, as the liquid phase method, a method using an ion exchange resin or a heteropoly acid as a catalyst is known. This liquid phase method does not show the drawbacks of the gas phase method, but since secondary butanol is obtained as an aqueous solution having a relatively low concentration, it is necessary to separate and purify the secondary butanol from this aqueous solution. there were.
【0005】この精製を蒸留操作により行う場合、第2
級ブタノールが水と共沸混合物を形成するので、共沸剤
を用いる共沸蒸留法,エントレーナー蒸留法あるいは抽
出・脱水蒸留法等の複雑な蒸留操作を行うことが必要で
あった。特に、ヘテロポリ酸を触媒とする液相法では、
生成する第2級ブタノールが触媒との水溶液として得ら
れるため、従来の精製方法では、腐蝕性を有する触媒水
溶液を大量に装置内を循環させることになり、耐食性の
高価な設備を用い、しかもエネルギー消費量も大きくな
るという重大な欠点があった。When this purification is carried out by a distillation operation, the second
Since grade-butanol forms an azeotropic mixture with water, it is necessary to perform complicated distillation operations such as an azeotropic distillation method using an azeotropic agent, an entrainer distillation method or an extraction / dehydration distillation method. In particular, in the liquid phase method using a heteropoly acid as a catalyst,
Since the produced secondary butanol is obtained as an aqueous solution with a catalyst, a large amount of a corrosive catalyst aqueous solution is circulated in the apparatus in the conventional refining method, and expensive equipment having corrosion resistance is used, and energy consumption is reduced. There was a serious drawback that the consumption amount also increased.
【0006】[0006]
【課題を解決するための手段】本発明者らは、効率のよ
い第2級ブタノールの精製方法について検討を重ねた結
果、液相法によるn−ブテンの水和反応において反応系
内の圧力を所定の圧力以上に維持すると、水和反応によ
り生成した第2級ブタノールが予想以上に多量にガス状
態で存在し、それ故、このガス相を系外へ抜き出し、冷
却液化すれば、容易かつ効率よく純粋な第2級ブタノー
ルを得ることができることを見出し、本発明を完成する
に至った。As a result of repeated studies on an efficient method for purifying secondary butanol, the present inventors have found that the pressure in the reaction system in the hydration reaction of n-butene by the liquid phase method is controlled. When the pressure is maintained above a certain level, a large amount of secondary butanol produced by the hydration reaction is present in an unexpectedly large amount in a gas state. Therefore, if this gas phase is taken out of the system and cooled and liquefied, it is easy and efficient. The present inventors have found that a highly pure secondary butanol can be obtained, and completed the present invention.
【0007】すなわち、本発明はn−ブテンを含む第2
級ブタノールの水溶液を100kg/cm2 以上の圧力
下に保持した後、得られるガス相を系外に抜き出し、冷
却して油層と水層に分離し、次いで該油層からn−ブテ
ンを除去することを特徴とする第2級ブタノールの精製
法に関し、表現を変えるならば、第2級ブタノールの水
溶液とn−ブテンを100kg/cm2 以上の圧力下で
接触させた後、得られるガス相を系外に抜き出し、冷却
して油層と水層に分離し、次いで該油層からn−ブテン
を除去することを特徴とする第2級ブタノールの精製法
に関する。That is, the present invention relates to a second invention containing n-butene.
After maintaining an aqueous solution of butanol of a higher grade under a pressure of 100 kg / cm 2 or more, the obtained gas phase is taken out of the system, cooled to separate into an oil layer and an aqueous layer, and then n-butene is removed from the oil layer. Regarding the method for purifying secondary butanol, characterized in that, if the expression is changed, after contacting an aqueous solution of secondary butanol with n-butene under a pressure of 100 kg / cm 2 or more, the obtained gas phase is used as a system. The present invention relates to a method for purifying secondary butanol, which comprises extracting to the outside, cooling to separate an oil layer and an aqueous layer, and then removing n-butene from the oil layer.
【0008】上記の如く、本発明では第2級ブタノール
の水溶液にn−ブテンを導入することなどにより形成さ
れるn−ブテンを含む第2級ブタノールの水溶液を10
0kg/cm2 以上、さらに効果的には150kg/c
m2 以上の圧力下に保持すると、第2級ブタノールと水
との気液平衡関係が常用の推算法や常圧の実測データか
ら予測される関係から大きくずれて、第2級ブタノール
が多量にガス相側に移行する。したがって、このガス相
をガス状態のまま系外に抜き出し、これを冷却,液化す
ると、油相と水相に分かれるが、このうちの油相中から
蒸留等によりn−ブテンを除去すれば、高収率でほぼ純
粋な第2級ブタノールが得られる。As described above, in the present invention, an aqueous solution of secondary butanol containing n-butene formed by introducing n-butene into an aqueous solution of secondary butanol is used.
0 kg / cm 2 or more, more effectively 150 kg / c
When kept under a pressure of m 2 or more, the vapor-liquid equilibrium relationship between the secondary butanol and water deviates greatly from the relationship predicted by the conventional estimation method or the measured data of the atmospheric pressure, and the secondary butanol is contained in a large amount. Move to the gas phase side. Therefore, if this gas phase is taken out of the system in the gas state, cooled and liquefied, it is separated into an oil phase and an aqueous phase. If n-butene is removed from the oil phase by distillation or the like, the Yield of almost pure secondary butanol is obtained.
【0009】なお、第2級ブタノールの水溶液として
は、上記のように、直接水和して得られる比較的低濃度
の水溶液に限らず、様々な濃度の水溶液が用いられる。The aqueous solution of secondary butanol is not limited to the relatively low concentration aqueous solution obtained by direct hydration as described above, but various concentration aqueous solutions may be used.
【0010】n−ブテンの水和反応により第2級ブタノ
ールを製造する場合、触媒としてヘテロポリ酸を用いる
が、これを水溶液の形態で反応系に存在させる。反応温
度は180〜300℃、好ましくは200〜250℃と
し、反応圧力は100kg/cm2 以上、好ましくは1
50kg/cm2 以上とする。また、ヘテロポリ酸水溶
液のpHを2.3以下、好ましくは1.0〜2.0の範
囲に調節する。When the secondary butanol is produced by the hydration reaction of n-butene, a heteropoly acid is used as a catalyst, which is present in the reaction system in the form of an aqueous solution. The reaction temperature is 180 to 300 ° C., preferably 200 to 250 ° C., and the reaction pressure is 100 kg / cm 2 or more, preferably 1
50 kg / cm 2 or more. Further, the pH of the aqueous solution of the heteropolyacid is adjusted to 2.3 or less, preferably 1.0 to 2.0.
【0011】ここで、反応温度が300℃を越えると、
原料であるn−ブテンの重合反応などの副反応が起こり
好ましくない。一方、180℃未満にすると、反応の平
衡論上は有利になるが、反応速度が低下し、実用上好ま
しくない。また、反応圧力が100kg/cm2 未満で
は、反応速度が小さく実用的でない。ヘテロポリ酸水溶
液のpHが2.3よりも大きいと、n−ブテンの水和反
応の速度が充分に上がらず、また生成する第2級ブタノ
ールの平衡濃度も低下する。逆にpHの下限については
特に制限はなく、水和反応の進行上問題はないが、あま
り強酸性領域にすると、反応容器などの腐食のおそれが
あり、そのため金属チタンを使うなど反応容器の材質を
選定する必要がある。When the reaction temperature exceeds 300 ° C.,
A side reaction such as a polymerization reaction of the raw material n-butene occurs, which is not preferable. On the other hand, if the temperature is lower than 180 ° C., it is advantageous in the equilibrium theory of the reaction, but the reaction rate decreases, which is not preferable in practice. If the reaction pressure is less than 100 kg / cm 2 , the reaction rate is too low to be practical. When the pH of the aqueous solution of heteropolyacid is higher than 2.3, the rate of n-butene hydration reaction is not sufficiently increased, and the equilibrium concentration of the secondary butanol produced is also lowered. On the contrary, the lower limit of pH is not particularly limited, and there is no problem in the progress of the hydration reaction, but if it is set in a too strong acidic region, there is a risk of corrosion of the reaction container, and therefore the material of the reaction container such as using metallic titanium. Need to be selected.
【0012】なお、上記ヘテロポリ酸水溶液の濃度は、
用いるヘテロポリ酸の種類、その他様々な条件により異
なり、一義的に定めることはできないが、通常は1/1
000〜1/5モル/リットル、好ましくは1/500
〜1/10モル/リットルとする。また、ここで用いる
ヘテロポリ酸としては、様々なものをあげることができ
るが、ケイタングステン酸,リンタングステン酸,ケイ
モリブデン酸,リンモリブデン酸などのほか、二種以上
のヘテロ原子,ポリ原子の組合せでもよい。The concentration of the above aqueous solution of heteropolyacid is
It varies depending on the type of heteropolyacid used and various other conditions and cannot be uniquely determined, but is usually 1/1
000 to 1/5 mol / liter, preferably 1/500
˜1 / 10 mol / liter. As the heteropolyacid used here, various ones can be mentioned, and in addition to silicotungstic acid, phosphotungstic acid, silicomolybdic acid, phosphomolybdic acid, etc., a combination of two or more kinds of heteroatoms and polyatoms. But it's okay.
【0013】第2級ブタノール水溶液に導入するn−ブ
テンは、その純度に特に制限はなく、液相法によるn−
ブテンの直接水和反応に用いる原料n−ブテンであって
もよい。The purity of n-butene introduced into the secondary butanol aqueous solution is not particularly limited, and n-butene obtained by the liquid phase method is used.
The raw material n-butene used for the direct hydration reaction of butene may be used.
【0014】前述のように、n−ブテンと第2級ブタノ
ールの水溶液を100kg/cm2以上の圧力下で接触
させると、第2級ブタノールと水との気液平衡関係が大
きくずれて、第2級ブタノールが多量にガス相側に移行
するので、このガス相を系外に抜き出し、冷却,液化す
ると、油相と水相に分離する。この油相からn−ブテン
を除去するには、簡単な蒸留操作によればよい。油相に
は水がほとんど含まれていないため、n−ブテンを除去
すれば高純度の第2級ブタノールが得られる。As described above, when the aqueous solution of n-butene and the secondary butanol is brought into contact with each other under a pressure of 100 kg / cm 2 or more, the vapor-liquid equilibrium relationship between the secondary butanol and water is largely deviated, and Since a large amount of secondary butanol migrates to the gas phase side, when this gas phase is taken out of the system, cooled and liquefied, it is separated into an oil phase and an aqueous phase. A simple distillation operation may be used to remove n-butene from this oil phase. Since the oil phase contains almost no water, high-purity secondary butanol can be obtained by removing n-butene.
【0015】[0015]
【実施例】次に、本発明を実施例によりさらに詳しく説
明する。 実施例1〜3および比較例1,2 内容量120mlのチタン製反応管(長さ1m)にpH
1.6のケイタングステン酸水溶液100mlを仕込
み、該反応管下部より1−ブテンを120g/hrの流
量で流し、所定の温度,圧力条件に保持した。反応管の
液レベルを一定に調節しながら該反応管上部の気相部よ
りガスを抜き出し、これを冷却液化した。EXAMPLES Next, the present invention will be described in more detail by way of examples. Examples 1 to 3 and Comparative Examples 1 and 2 pH was set in a titanium reaction tube (length 1 m) having an internal capacity of 120 ml.
100 ml of an aqueous solution of silicotungstic acid of 1.6 was charged, and 1-butene was caused to flow from the lower part of the reaction tube at a flow rate of 120 g / hr, and the temperature and pressure were maintained at predetermined conditions. While adjusting the liquid level in the reaction tube to a constant level, gas was extracted from the gas phase portion above the reaction tube, and cooled and liquefied.
【0016】得られた液体を蒸留して1−ブテンを分離
して純度99.5%以上の第2級ブタノールを得た。こ
の際に得られた第2級ブタノールの量,反応管内の触媒
水溶液中の第2級ブタノール濃度および気相中の第2級
ブタノールと水蒸気との重量比を第1表に示す。The obtained liquid was distilled to separate 1-butene to obtain a secondary butanol having a purity of 99.5% or more. Table 1 shows the amount of the secondary butanol obtained at this time, the concentration of the secondary butanol in the catalyst aqueous solution in the reaction tube, and the weight ratio of the secondary butanol to water vapor in the gas phase.
【0017】[0017]
【表1】 [Table 1]
【0018】[0018]
【発明の効果】本発明の方法によれば、第2級ブタノー
ルの水溶液から効率よく高純度の第2級ブタノールを得
ることができる。特に油相と水相を分離する操作以降に
おいては、抽出剤を用いない簡単な蒸留操作等を適用で
きるため、エネルギー消費量が少ない。According to the method of the present invention, highly pure secondary butanol can be efficiently obtained from an aqueous solution of secondary butanol. In particular, after the operation of separating the oil phase and the water phase, a simple distillation operation or the like without using an extractant can be applied, so that the energy consumption is small.
Claims (3)
溶液を100kg/cm2 以上の圧力下に保持した後、
得られるガス相を系外に抜き出し、冷却して油層と水層
に分離し、次いで該油層からn−ブテンを除去すること
を特徴とする第2級ブタノールの精製法。1. After maintaining an aqueous solution of secondary butanol containing n-butene under a pressure of 100 kg / cm 2 or more,
A method for purifying secondary butanol, which comprises extracting the obtained gas phase out of the system, cooling it to separate it into an oil layer and an aqueous layer, and then removing n-butene from the oil layer.
を100kg/cm2 以上の圧力下で接触させた後、得
られるガス相を系外に抜き出し、冷却して油層と水層に
分離し、次いで該油層からn−ブテンを除去することを
特徴とする第2級ブタノールの精製法。2. An aqueous secondary butanol solution and n-butene are contacted with each other under a pressure of 100 kg / cm 2 or more, and the obtained gas phase is extracted from the system and cooled to separate into an oil layer and an aqueous layer. And then removing n-butene from the oil layer, wherein the secondary butanol is purified.
と100kg/cm2 以上の圧力下で接触させ水和反応
を行った後、得られた反応混合物からガス相を系外に抜
き出し、冷却液化して油層と水層に分離し、次いで該油
層からn−ブテンを除去することを特徴とする第2級ブ
タノールの精製法。3. A n-butene is brought into contact with an aqueous silicotungstic acid solution under a pressure of 100 kg / cm 2 or more to carry out a hydration reaction, and then a gas phase is extracted from the obtained reaction mixture to the outside of the system to be cooled and liquefied. To separate an oil layer and an aqueous layer, and then remove n-butene from the oil layer, to purify the secondary butanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3133313A JPH07569B2 (en) | 1991-05-10 | 1991-05-10 | Purification method of secondary butanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3133313A JPH07569B2 (en) | 1991-05-10 | 1991-05-10 | Purification method of secondary butanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05345736A true JPH05345736A (en) | 1993-12-27 |
| JPH07569B2 JPH07569B2 (en) | 1995-01-11 |
Family
ID=15101764
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3133313A Expired - Fee Related JPH07569B2 (en) | 1991-05-10 | 1991-05-10 | Purification method of secondary butanol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07569B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101104087B1 (en) * | 2003-03-22 | 2012-01-12 | 에보니크 옥세노 게엠베하 | Separation of 2-butanol from t-butanol / water mixture |
-
1991
- 1991-05-10 JP JP3133313A patent/JPH07569B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101104087B1 (en) * | 2003-03-22 | 2012-01-12 | 에보니크 옥세노 게엠베하 | Separation of 2-butanol from t-butanol / water mixture |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07569B2 (en) | 1995-01-11 |
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