JP2802673B2 - Purification method of cyclohexene for hydration reaction - Google Patents
Purification method of cyclohexene for hydration reactionInfo
- Publication number
- JP2802673B2 JP2802673B2 JP2145282A JP14528290A JP2802673B2 JP 2802673 B2 JP2802673 B2 JP 2802673B2 JP 2145282 A JP2145282 A JP 2145282A JP 14528290 A JP14528290 A JP 14528290A JP 2802673 B2 JP2802673 B2 JP 2802673B2
- Authority
- JP
- Japan
- Prior art keywords
- extractant
- cyclohexene
- benzene
- cyclohexane
- reaction
- 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.)
- Expired - Lifetime
Links
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 title claims description 62
- 238000000034 method Methods 0.000 title claims description 17
- 238000006703 hydration reaction Methods 0.000 title claims description 9
- 238000000746 purification Methods 0.000 title description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 51
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 12
- 238000000354 decomposition reaction Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000000895 extractive distillation Methods 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical group CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical group N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 4
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical group COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 claims description 3
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical group COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 claims description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical group O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 description 2
- 150000002830 nitrogen compounds Chemical class 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- NGCJVMZXRCLPRQ-UHFFFAOYSA-N 2-methylidenepentanedinitrile Chemical compound N#CC(=C)CCC#N NGCJVMZXRCLPRQ-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 1
- -1 sulfolane is used Chemical class 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
- C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
- C07C7/08—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by extractive distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は、水和反応用のシクロヘキセンの精製方法に
関し、さらに詳しくは、ベンゼンの部分水素化反応にお
いて得られるシクロヘキサン、シクロヘキセンおよびベ
ンゼンの混合物から、抽出蒸留によりシクロヘキサン、
シクロヘキセンおよびベンゼンを分離した後、得られる
シクロヘキセン中に含まれる抽剤および／または抽剤の
分解物を水で抽出除去した後、水和反応に供するように
した水和反応用のシクロヘキセンの精製方法に関する。Description: TECHNICAL FIELD The present invention relates to a method for purifying cyclohexene for a hydration reaction, and more particularly, to a method for producing a mixture of cyclohexane, cyclohexene and benzene obtained in a partial hydrogenation reaction of benzene. , Cyclohexane by extractive distillation,
After separating cyclohexene and benzene, a method for purifying cyclohexene for a hydration reaction, wherein the extractant and / or a decomposition product of the extractant contained in the obtained cyclohexene is extracted and removed with water, and then subjected to a hydration reaction. About.
（従来の技術） ベンゼンの部分水素化反応においては、未反応のベン
ゼン、シクロヘキセンと完全水素化されたシクロヘキサ
ンとの混合物として得られる。シクロヘキサン、シクロ
ヘキセンおよびベンゼンの沸点はあまりにも接近してい
るため、通常の蒸留では各３成分を分離取得することが
できない。(Prior Art) In the partial hydrogenation reaction of benzene, it is obtained as a mixture of unreacted benzene, cyclohexene and fully hydrogenated cyclohexane. Since the boiling points of cyclohexane, cyclohexene and benzene are too close, each of the three components cannot be separated and obtained by ordinary distillation.
これらの混合物より各成分を分離取得する方法として
は、抽出蒸留による方法が提案されている。例えば、特
開昭58−172323号公報、特開昭58−164524号公報、特開
昭58−164525号公報が挙げられる。As a method for separating and obtaining each component from these mixtures, a method using extractive distillation has been proposed. For example, JP-A-58-172323, JP-A-58-164524, and JP-A-58-164525 can be mentioned.
（発明が解決しようとする課題） しかしながら、かかる抽出蒸留によって分離取得され
たベンゼン、シクロヘキセン、シクロヘキサン中の抽剤
もしくはその分解物を皆無にすることは極めて困難であ
る。(Problems to be Solved by the Invention) However, it is extremely difficult to eliminate the extractant or its decomposed product in benzene, cyclohexene, and cyclohexane separated and obtained by the extractive distillation.
一方、これらの製品は、溶剤あるいは各種化学品中間
原料として使用されるため、抽剤もしくはその分解物が
混入すると、以下のような弊害を生じることとなる。例
えば、カルボン酸エステルあるいはカルボン酸アミドを
抽剤として使用した場合には、分解物であるカルボン酸
等が装置の腐食をもたらすことがあり、また、アジポニ
トリルやアミド類を抽剤として用いた場合には、それ自
身もしくはその分解物である窒素化合物が各種反応の触
媒毒となることがあり、さらには、スルホランのごとき
硫黄化合物を用いた場合には、例えば、水素化反応の触
媒毒となることがある。On the other hand, since these products are used as a solvent or an intermediate material for various chemicals, if an extractant or a decomposition product thereof is mixed, the following adverse effects will occur. For example, when a carboxylic acid ester or a carboxylic acid amide is used as an extractant, a carboxylic acid or the like as a decomposition product may cause corrosion of the device, and when adiponitrile or an amide is used as an extractant, In some cases, a nitrogen compound that is itself or a decomposition product thereof may be a catalyst poison for various reactions, and when a sulfur compound such as sulfolane is used, for example, it may be a catalyst poison for a hydrogenation reaction. There is.
以上のように、ベンゼン、シクロヘキセン、シクロヘ
キサンに抽剤もしくは抽剤の分解物が混入することは、
工業的にみて非常に好ましくない。As described above, benzene, cyclohexene, and cyclohexane are mixed with the extractant or the decomposition product of the extractant,
It is very unfavorable industrially.
（課題を解決するための手段） 本発明者らは、かかる課題を解決するために鋭意検討
した結果、シクロヘキセンを水和反応に供する場合に
は、シクロヘキセン中に含まれる抽剤および／または抽
剤の分解物を除去する方法として、水で抽出除去する方
法が極めて有効であることを見出し、本発明に至ったも
のである。(Means for Solving the Problems) The present inventors have conducted intensive studies to solve the problems, and as a result, when cyclohexene is subjected to a hydration reaction, an extractant and / or extractant contained in cyclohexene is used. It has been found that a method of extracting and removing with water is extremely effective as a method of removing the decomposition products of the present invention, and has led to the present invention.
すなわち、本発明は、ベンゼンの部分水添反応におい
て得られるシクロヘキサン、シクロヘキセンおよびベン
ゼンの混合物から、各３成分の分離可能な、かつ、20℃
における誘電率が10〜60の範囲にある抽剤を用い、抽出
蒸留によりシクロヘキサン、シクロヘキセンおよびベン
ゼンを分離した後、得られるシクロヘキセン中に含まれ
る抽剤および／または抽剤の分解物を水で抽出除去した
後、水和反応に供することを特徴とする水和反応用のシ
クロヘキセンの精製方法に関するものである。That is, the present invention provides a process for separating each of three components from a mixture of cyclohexane, cyclohexene and benzene obtained in a partial hydrogenation reaction of benzene, at 20 ° C.
After extracting cyclohexane, cyclohexene and benzene by extractive distillation using an extractant having a dielectric constant in the range of 10 to 60, the extractant contained in the obtained cyclohexene and / or a decomposition product of the extractant is extracted with water. The present invention relates to a method for purifying cyclohexene for a hydration reaction, which is subjected to a hydration reaction after removal.
以下、本発明の具体的な実施態様を説明する。 Hereinafter, specific embodiments of the present invention will be described.
本発明の効果が得られる抽剤は、20℃における誘電率
が10〜60の範囲にあるものである。例えば、N,N−ジメ
チルアセトアミド、アジポニトリル、スルホラン、マロ
ン酸ジメチル、コハク酸ジメチル、ジエチレングリコー
ル、N,N−ジメチルホルムアミド、フルフラール、ジメ
チルスルホキシド、スクシノニトリル、グルタロニトリ
ル、２−メチレングルタロニトリル、マロンニトリル、
ベンゾニトリル、γ−ブチロラクトン、γ−バレロラク
トン、γ−カプロラクトン、Ｎ−メチルピロリドン、ｍ
−クレゾール、ニトロベンゼン、ニトロメタン、メチル
イソブチルケトンが挙げられる。The extractant which can obtain the effects of the present invention has a dielectric constant at 20 ° C. in the range of 10 to 60. For example, N, N-dimethylacetamide, adiponitrile, sulfolane, dimethyl malonate, dimethyl succinate, diethylene glycol, N, N-dimethylformamide, furfural, dimethylsulfoxide, succinonitrile, glutaronitrile, 2-methyleneglutaronitrile, Malononitrile,
Benzonitrile, γ-butyrolactone, γ-valerolactone, γ-caprolactone, N-methylpyrrolidone, m
-Cresol, nitrobenzene, nitromethane, methyl isobutyl ketone.
本発明において、水で抽出除去する対象は、抽出蒸留
で分離取得されるシクロヘキセン中の抽剤と抽剤の分解
物である。抽剤の分解物とは、例えば、N,N−ジメチル
ホルムアミドやN,N−ジメチルアセトアミドを使用する
場合においては、モノメチルアミン、ジメチルアミン、
トリメチルアミン等の窒素化合物を言い、また、コハク
酸ジメチルやマロン酸ジメチルを使用する場合において
は、カルボニル化合物を言う。これらは抽剤の熱分解、
あるいは微量の水による加水分解等で生成してくるもの
である。In the present invention, the target to be extracted and removed with water is an extractant and a decomposition product of the extractant in cyclohexene separated and obtained by extractive distillation. The decomposition product of the extractant is, for example, when using N, N-dimethylformamide or N, N-dimethylacetamide, monomethylamine, dimethylamine,
The term refers to a nitrogen compound such as trimethylamine. When dimethyl succinate or dimethyl malonate is used, it refers to a carbonyl compound. These are the thermal decomposition of the extractant,
Alternatively, it is produced by hydrolysis with a small amount of water.
水を用いた抽出除去の操作温度は特に規定されるもの
でないが、除去される物質の水への液々分配比が低温側
で高くなることが多いので、好ましくは10〜70℃、より
好ましくは20〜60℃で行う。また、操作圧力は大気圧、
加圧、減圧のいずれにおいても実施することができる。The operation temperature of extraction and removal using water is not particularly limited, but the liquid-to-water distribution ratio of the substance to be removed is often higher on the low temperature side, so it is preferably 10 to 70 ° C, more preferably Is performed at 20-60 ° C. The operating pressure is atmospheric pressure,
It can be carried out either under pressure or under reduced pressure.
抽出除去操作において、水のみでも十分に効果を有す
るが、酸、アルカリあるいは塩を添加して除去性能を高
めることもできる。In the extraction removal operation, water alone has a sufficient effect, but the removal performance can be enhanced by adding an acid, an alkali or a salt.
本発明の実施態様としては、回分式、連続式がある
が、連続式が好ましく、さらに、連続式で行う場合にお
いては、向流接触式が好ましい。Embodiments of the present invention include a batch system and a continuous system, but a continuous system is preferable, and when a continuous system is used, a countercurrent contact system is preferable.
水の使用量については特に制限はなく、製品中に含ま
れる抽剤および／または分解物の濃度や分配比によって
適宜定めればよい。The amount of water used is not particularly limited, and may be appropriately determined depending on the concentration and distribution ratio of the extractant and / or the decomposition product contained in the product.
（発明の効果） 本発明方法によって、シクロヘキサン、シクロヘキセ
ンおよびベンゼンの混合物から、抽出蒸留により得られ
るシクロヘキセン中に含まれる抽剤および／または抽剤
の分解物が抽出除去され、水和反応用に好適な極めて高
度に精製されたシクロヘキセンを得ることができる。(Effects of the Invention) According to the method of the present invention, a mixture of cyclohexane, cyclohexene and benzene extracts and removes an extractant and / or a decomposition product of the extractant contained in cyclohexene obtained by extractive distillation, which is suitable for a hydration reaction. Thus, very highly purified cyclohexene can be obtained.
（実施例） 以下、実施例をもって本発明をさらに詳細に説明する
が、本発明は、これらの例によってなんら限定されるも
のではない。(Examples) Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
実施例１ シクロヘキサン、シクロヘキセンおよびベンゼンの混
合物から、抽剤としてN,N−ジメチルアセトアミドを用
いて抽出蒸留分離したところ、純度99.5重量％のシクロ
ヘキサンと99.7重量％のシクロヘキセンおよび99.9重量
％のベンゼンが得られた。また、これらの各取得物質中
にはジメチルアミンがそれぞれ5ppm、4ppm、2ppm含まれ
ていた。Example 1 Extraction and distillation of a mixture of cyclohexane, cyclohexene and benzene using N, N-dimethylacetamide as an extractant gave 99.5% by weight of cyclohexane, 99.7% by weight of cyclohexene and 99.9% by weight of benzene. Was done. Moreover, dimethylamine was contained in each of these acquired substances at 5 ppm, 4 ppm, and 2 ppm, respectively.
次に、これらの各取得物質中、シクロヘキセンを使用
するために、長さ4m、塔径150φの充填塔を用い、塔頂
より水を30kg/H、塔底より抽出蒸留で取得されたシクロ
ヘキセンを100kg/Hで供給して精製を行った。その結
果、塔頂より得られたシクロヘキセン中にジメチルアミ
ンは検出されなかった。Next, in each of these obtained substances, in order to use cyclohexene, using a packed column with a length of 4 m and a tower diameter of 150 φ, water from the top of the column 30 kg / H, cyclohexene obtained by extractive distillation from the bottom of the column Purification was performed by supplying at 100 kg / H. As a result, dimethylamine was not detected in cyclohexene obtained from the top of the tower.
実施例２ ZSM−５ 1kgと水を仕込んだ反応器を用い、120℃、6
K/G条件下で、実施例１にて精製したシクロヘキセンを5
00g/Hで連続的にフィードして反応させたところ、反応
器出口のオイル中のシクロヘキサノール濃度は、反応開
始時の12.51重量％から、10時間後においても12.45重量
％とほとんど変わらなかった。Example 2 Using a reactor charged with 1 kg of ZSM-5 and water, 120 ° C., 6
Under K / G conditions, the cyclohexene purified in Example 1 was
When the reaction was continuously fed at 00 g / H to carry out the reaction, the concentration of cyclohexanol in the oil at the outlet of the reactor was almost unchanged from 12.51% by weight at the start of the reaction to 12.45% by weight even after 10 hours.
比較例１ 実施例１の抽出蒸留で分離取得されたシクロヘキセン
を使用し、実施例２と同様の反応を行ったところ、反応
器出口のオイル中のシクロヘキサノール転化率は、反応
開始時の12.43重量％から、10時間後7.83重量％まで低
下した。Comparative Example 1 The same reaction as in Example 2 was performed using cyclohexene separated and obtained by extractive distillation in Example 1, and the conversion of cyclohexanol in the oil at the outlet of the reactor was 12.43 weight at the start of the reaction. % To 7.83% by weight after 10 hours.
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.6，ＤＢ名) C07C 13/20,7/10──────────────────────────────────────────────────続 き Continued on front page (58) Field surveyed (Int. Cl. 6 , DB name) C07C 13/20, 7/10
Claims (7)
シクロヘキサン、シクロヘキセンおよびベンゼンの混合
物から、各３成分の分離可能な、かつ、20℃における誘
電率が10〜60の範囲にある抽剤を用い、抽出蒸留により
シクロヘキサン、シクロヘキセンおよびベンゼンを分離
した後、得られるシクロヘキセン中に含まれる抽剤およ
び／または抽剤の分解物を水で抽出除去した後、水和反
応に供することを特徴とする水和反応用のシクロヘキセ
ンの精製方法。An extractant which is capable of separating each of the three components from a mixture of cyclohexane, cyclohexene and benzene obtained in a partial hydrogenation reaction of benzene and has a dielectric constant in the range of 10 to 60 at 20 ° C. Separating cyclohexane, cyclohexene and benzene by extractive distillation, extracting and extracting the extractant and / or the decomposition product of the extractant contained in the obtained cyclohexene with water, and then subjecting the extract to a hydration reaction. A method for purifying cyclohexene for a summation reaction.
１記載の方法。2. The method according to claim 1, wherein the extractant is dimethylacetamide.
の方法。3. The method according to claim 1, wherein the extractant is adiponitrile.
リルの混合溶剤である請求項１記載の方法。4. The method according to claim 1, wherein the extractant is a mixed solvent of dimethylacetamide and adiponitrile.
載の方法。5. The method according to claim 1, wherein the extractant is dimethyl malonate.
載の方法。6. The method according to claim 1, wherein the extractant is dimethyl succinate.
法。7. The method according to claim 1, wherein the extractant is sulfolane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2145282A JP2802673B2 (en) | 1990-06-05 | 1990-06-05 | Purification method of cyclohexene for hydration reaction |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2145282A JP2802673B2 (en) | 1990-06-05 | 1990-06-05 | Purification method of cyclohexene for hydration reaction |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0441441A JPH0441441A (en) | 1992-02-12 |
| JP2802673B2 true JP2802673B2 (en) | 1998-09-24 |
Family
ID=15381537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2145282A Expired - Lifetime JP2802673B2 (en) | 1990-06-05 | 1990-06-05 | Purification method of cyclohexene for hydration reaction |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2802673B2 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69613309T2 (en) * | 1995-10-20 | 2002-05-02 | Mitsubishi Chemical Corp., Tokio/Tokyo | Process for the separation of cyclohexene |
| JP5082254B2 (en) * | 2005-02-18 | 2012-11-28 | 三菱化学株式会社 | Method for producing aromatic compound and method for producing hydrogenated aromatic compound |
| EP2017247A1 (en) * | 2006-05-10 | 2009-01-21 | Idemitsu Kosan Co., Ltd. | Process for producing adamantane |
| US7790943B2 (en) * | 2006-06-27 | 2010-09-07 | Amt International, Inc. | Integrated process for removing benzene from gasoline and producing cyclohexane |
| CN102134177A (en) * | 2011-02-28 | 2011-07-27 | 河北民海化工有限公司 | Method for separating cyclohexane and cyclohexene by extraction and rectification |
| JP7369044B2 (en) * | 2020-01-21 | 2023-10-25 | 株式会社ダイセル | gas generator |
-
1990
- 1990-06-05 JP JP2145282A patent/JP2802673B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0441441A (en) | 1992-02-12 |
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