JPH03287548A - Purification of cyclohexane - Google Patents
Purification of cyclohexaneInfo
- Publication number
- JPH03287548A JPH03287548A JP8746190A JP8746190A JPH03287548A JP H03287548 A JPH03287548 A JP H03287548A JP 8746190 A JP8746190 A JP 8746190A JP 8746190 A JP8746190 A JP 8746190A JP H03287548 A JPH03287548 A JP H03287548A
- Authority
- JP
- Japan
- Prior art keywords
- cyclohexane
- methylcyclopentenes
- crude
- methylcyclopentane
- catalyst
- 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
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims abstract description 65
- 238000000746 purification Methods 0.000 title abstract description 4
- ATQUFXWBVZUTKO-UHFFFAOYSA-N 1-methylcyclopentene Chemical class CC1=CCCC1 ATQUFXWBVZUTKO-UHFFFAOYSA-N 0.000 claims abstract description 31
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims description 19
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000004821 distillation Methods 0.000 abstract description 10
- 239000012535 impurity Substances 0.000 abstract description 5
- 239000013462 industrial intermediate Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 238000005984 hydrogenation reaction Methods 0.000 description 17
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- CXOZQHPXKPDQGT-UHFFFAOYSA-N 3-Methylcyclopentene Chemical compound CC1CCC=C1 CXOZQHPXKPDQGT-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- FWMRUAODTCVEQK-UHFFFAOYSA-N 4-methylcyclopentene Chemical compound CC1CC=CC1 FWMRUAODTCVEQK-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- KDDXDCZUWXOADG-UHFFFAOYSA-N cyclohexene;hydrate Chemical compound O.C1CCC=CC1 KDDXDCZUWXOADG-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、シクロヘキサンの精製方法に関し、さらに詳
しくは、シクロヘキサンの工業的用途において要求され
る高純度シクロヘキサンを採取するに当たり、特にメチ
ルシクロペンテン類を含有する粗シクロヘキサンを精製
する方法に関するも（従来の技術）
シクロヘキサンは重要な工業中間原料であり、ベンゼン
の水素化により製造されている。製品シクロヘキサンに
要求される純度は極めて高く、ベンゼンの水素化におい
て、未反応ベンゼン量を低減したり、他の副反応生成物
、例えば、環状メチル化合物などを低く抑えるなどの工
夫をしているのが普通である。このようなベンゼンの単
純な水素化によるシクロヘキサンの製造方法は、工業的
完成度が高く、また、プロセスや反応が単純なため、製
品シクロヘキサンにオレフィン類が混在もしくは残存す
ることはほとんどない。本発明が意図する技術は、従来
の単純なシクロヘキサンの製造方法に関わるものとは異
なり、例えば、以下のごとき場合に適用される新しい技
術である。Detailed Description of the Invention (Field of Industrial Application) The present invention relates to a method for purifying cyclohexane, and more specifically, in collecting high-purity cyclohexane required for industrial use of cyclohexane, in particular, methylcyclopentenes are purified. Related to a method for purifying crude cyclohexane containing cyclohexane (prior art) Cyclohexane is an important industrial intermediate raw material and is produced by hydrogenation of benzene. The purity required for the product cyclohexane is extremely high, and in the hydrogenation of benzene, efforts are made to reduce the amount of unreacted benzene and to keep other side reaction products, such as cyclic methyl compounds, low. is normal. This method of producing cyclohexane by simple hydrogenation of benzene has a high degree of industrial perfection, and the process and reaction are simple, so olefins are hardly mixed or left in the cyclohexane product. The technology contemplated by the present invention is different from the conventional simple method for producing cyclohexane, and is a new technology that can be applied, for example, to the following cases.
シクロヘキサンの工業用途は、その多くが酸化反応によ
ってシクロヘキサノン、シクロヘキサノール混合物（以
下「オロン」と略す）を得るためのものである、しかし
、最近において、オロンではなく、純水のシクロヘキサ
ノールを得る方法が例えば、特開昭６３−１５６７３６
号公報、特公平１−３３４５３号公報などで検討されて
いる。Most of the industrial uses of cyclohexane are to obtain a mixture of cyclohexanone and cyclohexanol (hereinafter referred to as "Olon") through oxidation reactions.However, recently, a method for obtaining pure water cyclohexanol instead of Olone has been developed. For example, JP-A-63-156736
This method is discussed in Japanese Patent Publication No. 1-33453, etc.
これらの方法は、ベンゼンを部分水素化してシクロヘキ
センとシクロヘキサンの混合物を得、このうちシクロヘ
キセンを酸触媒の存在下に水和してシクロヘキサノール
を得ようとするものであり、従来のオロン製造法とは技
術的に全く異なるものであり、工業的価値も高い、しか
し、一方では、シクロヘキセンの酸触媒による水和反応
においては、シクロヘキサノール以外に多少なりともシ
クロヘキセンの異性化物であるメチルシクロペンテン類
を副生ずることがわかっている（例えば、特公平１−３
３４５３号公報）、このメチルシクロペンテン類は、最
終的には部分水素化反応のもうひとつの生成物であるシ
クロヘキサンとともに取り出すことがシクロヘキサノー
ル製造プロセス上最適であ−ることか、本発明者らの別
の検討で明らかとなっている。ここに、従来にないメチ
ルシクロペンテンを含有する粗シクロヘキサンが得うし
ることになるが、前述のごとく、シクロヘキサンの工業
的な要求純度が高く、該粗シクロヘキサンを精製する新
しい技術が必要となるのである。These methods partially hydrogenate benzene to obtain a mixture of cyclohexene and cyclohexane, and hydrate cyclohexene in the presence of an acid catalyst to obtain cyclohexanol, which is different from the conventional olone production method. are technically completely different and have high industrial value. However, on the other hand, in the acid-catalyzed hydration reaction of cyclohexene, methylcyclopentenes, which are isomerized products of cyclohexene, are used as sub-agents in addition to cyclohexanol. It is known that this occurs (for example,
3453), the present inventors have determined that it is optimal for the cyclohexanol production process to ultimately extract these methylcyclopentenes together with cyclohexane, which is another product of the partial hydrogenation reaction. This was made clear in another study. Here, crude cyclohexane containing methylcyclopentene, which is unprecedented, can be obtained, but as mentioned above, the industrially required purity of cyclohexane is high, and a new technology for purifying the crude cyclohexane is required. .
以上メチルシクロペンテン類を含有する粗シクロヘキサ
ンの例を示したが、本発明方法を適用できる範囲は、当
然のことながらこの例に限られるものではない。Although an example of crude cyclohexane containing methylcyclopentenes has been shown above, the scope to which the method of the present invention can be applied is not limited to this example, as a matter of course.
（発明が解決しようとする課Ｂ）
従来、メチルシクロペンテン類を例えば数千ｐｐ−以上
含むような粗シクロヘキサンは、従来のベンゼンの水素
化反応によって得られるものとは全く異なり、したがっ
て、その精製方法も知られていない０例えば、該粗シク
ロヘキサンからメチルシクロペンテン類を単なる蒸留操
作によって分離しようとすると、シクロヘキサンとメチ
ルシクロペンテン類との比揮発度が極めて１に近いため
、実質的に不可能である。また、抽出蒸留による分離も
考えられるが、やはり比揮発度が小さく、また、抽出溶
媒という新たな成分を必要とするため、工業的にみて価
値のある方法とは言いがたい。(Problem B to be Solved by the Invention) Conventionally, crude cyclohexane containing, for example, several thousand pp- or more of methylcyclopentenes is completely different from that obtained by the conventional hydrogenation reaction of benzene. For example, it is virtually impossible to separate methylcyclopentenes from the crude cyclohexane by simple distillation because the relative volatility of cyclohexane and methylcyclopentenes is extremely close to 1. Separation by extractive distillation is also considered, but it is difficult to say that it is a valuable method from an industrial perspective because the specific volatility is low and a new component called an extraction solvent is required.
すなわち、もっと簡便で有効な該粗シクロヘキサンの精
製方法が強く望まれるのである。That is, a simpler and more effective method for purifying crude cyclohexane is strongly desired.
（課題を解決するための手段）
本発明者らは、かかるメチルシクロペンテン類を含有す
る粗シクロヘキサンを簡便に、かつ、確実に精製する方
法を鋭意検討した結果、メチルシクロペンテン類を水素
化してメチルシクロペンタンとし、次に蒸留によって精
製する方法が最も適した手段であるとの結論に達し、本
発明を完成するに至った。(Means for Solving the Problems) As a result of intensive research into a method for easily and reliably purifying crude cyclohexane containing such methylcyclopentenes, the present inventors have found that methylcyclopentenes can be hydrogenated to produce methylcyclopentenes. It was concluded that the most suitable method was to convert pentane into pentane and then purify it by distillation, leading to the completion of the present invention.
すなわち、本発明は、メチルシクロペンテン類を含有す
る粗シクロヘキサンから高純度のシクロヘキサンを採取
するに際し、該粗シクロヘキサンを触媒の存在下に水素
化処理をしてメチルシクロペンテン類をメチルシクロペ
ンタンとし、次に蒸留によって塔頂よりメチルシクロペ
ンタンを分離除去することを特徴とするシクロヘキサン
の精製方法である。That is, in the present invention, when extracting highly pure cyclohexane from crude cyclohexane containing methylcyclopentenes, the crude cyclohexane is hydrogenated in the presence of a catalyst to convert the methylcyclopentenes into methylcyclopentane, and then This is a cyclohexane purification method characterized by separating and removing methylcyclopentane from the top of the column by distillation.
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.
本発明方法によって精製しようとする粗シクロヘキサン
とは、主にメチルシクロペンテン類を不純物として含有
するものである。ここでメチルシクロペンテン類とは、
１−メチルシクロペンテン、３−メチルシクロペンテン
および４−メチルシクロペンテンをいい、特に１−メチ
ルシクロペンテン、３−メチルシクロペンテンをいう。The crude cyclohexane to be purified by the method of the present invention mainly contains methylcyclopentenes as impurities. Here, methylcyclopentenes are
It refers to 1-methylcyclopentene, 3-methylcyclopentene and 4-methylcyclopentene, particularly 1-methylcyclopentene and 3-methylcyclopentene.
メチルシクロペンテン類の含有量としては、該粗シクロ
ヘキサン中の重量分率として０．０１ないし数十％であ
る。また、該粗シクロヘキサン中にはメチルシクロペン
テン類以外に他の不純物、例えばベンゼンやシクロヘキ
セン、さらには炭素数１から６の炭化水素を含んでいて
もさしつかえない。ベンゼンやシクロヘキセンは、後述
する水素化処理によってシクロヘキサンとすることがで
きる一方、炭素数１から６の炭化水素は、本発明方法に
おける蒸留操作によって塔頂より容易に除去することが
できるからである。The content of methylcyclopentenes is 0.01 to several tens of percent by weight in the crude cyclohexane. Further, the crude cyclohexane may contain other impurities other than methylcyclopentenes, such as benzene, cyclohexene, and even hydrocarbons having 1 to 6 carbon atoms. This is because benzene and cyclohexene can be converted into cyclohexane by the hydrogenation treatment described below, while hydrocarbons having 1 to 6 carbon atoms can be easily removed from the top of the column by the distillation operation in the method of the present invention.
粗シクロヘキサンの水素化処理は、触媒の存在下におい
て気相でも液相でも行うことができる。The hydrogenation of crude cyclohexane can be carried out in the presence of a catalyst in the gas phase or in the liquid phase.
触媒としては、通常のオレフィン水素化用触媒や芳香族
炭化水素の水素化用触媒を用いればよく、具体的にはＮ
ｉ触媒やＰｔ、 Ｐｄ、 Ｒｕなどの貴金属触媒が挙げ
られ、経済的観点からはＮｉ触媒が好適である。水素化
処理条件としては不純物の含有量にもよるが、通常室温
ないし３００″Ｃ１好ましくは５０ないし２００°Ｃの
温度範囲、１ないし１００気圧、好ましくは５ないし５
０気圧の水素圧力範囲で行う。反応形式としては特に制
限はないが、固定床式のいわゆるトリクルベツド型の反
応方法は好ましく用いることができる。このような水素
化処理によって、粗シクロヘキサン中のメチルシクロペ
ンテン類のほとんどすべてをメチルシクロペンタンに転
化させることができる。As a catalyst, a normal olefin hydrogenation catalyst or an aromatic hydrocarbon hydrogenation catalyst may be used. Specifically, N
Examples of the catalyst include an i catalyst and a noble metal catalyst such as Pt, Pd, and Ru, and from an economical point of view, a Ni catalyst is preferable. The hydrogenation treatment conditions depend on the content of impurities, but are usually in the temperature range of room temperature to 300" C1, preferably 50 to 200 °C, 1 to 100 atm, preferably 5 to 5
It is carried out in the hydrogen pressure range of 0 atmospheres. Although there are no particular limitations on the reaction format, a fixed bed type, so-called trickle bed type reaction method can be preferably used. By such hydrogenation treatment, almost all of the methylcyclopentenes in crude cyclohexane can be converted to methylcyclopentane.
メチルシクロペンタンを含むシクロヘキサンは、次に蒸
留によって高純度シクロヘキサンに精製する。蒸留操作
は常圧下においても、また、減圧下、加圧下においても
実施することができ、適宜選択すればよい。この蒸留に
よって、メチルシクロペンタンに冨んだ留出液を塔頂よ
り除去し、塔底より極めて高純度のシクロヘキサンを採
取することができる。また、粗シクロヘキサン中にシク
ロヘキサン、メチルシクロペンテン類以外の炭素数１か
ら６の炭化水素が含まれていても、この蒸留操作によっ
て、メチルシクロペンタンとともに容易に塔頂から除去
することができる。The cyclohexane containing methylcyclopentane is then purified to high purity cyclohexane by distillation. The distillation operation can be carried out under normal pressure, reduced pressure, or increased pressure, which may be selected as appropriate. By this distillation, the distillate containing methylcyclopentane can be removed from the top of the column, and extremely pure cyclohexane can be collected from the bottom of the column. Further, even if the crude cyclohexane contains hydrocarbons having 1 to 6 carbon atoms other than cyclohexane and methylcyclopentenes, they can be easily removed from the top of the column along with methylcyclopentane by this distillation operation.
以上のごとき本発明方法によって得られるシクロヘキサ
ンの純度は、工業的に要求される純度として充分以上で
あり、具体的には９９％以上、または９９．５％以上、
さらには９９．９％以上のシクロヘキサンを取得するこ
とができる。The purity of cyclohexane obtained by the method of the present invention as described above is more than sufficient for industrially required purity, specifically, 99% or more, or 99.5% or more,
Furthermore, 99.9% or more of cyclohexane can be obtained.
（発明の効果）
本発明方法によってメチルシクロペンテン類を含有する
粗シクロヘキサンを精製して、極めて高純度のシクロヘ
キサンを取得することができ、その工業的価値は高い。(Effects of the Invention) By the method of the present invention, crude cyclohexane containing methylcyclopentenes can be purified to obtain extremely pure cyclohexane, which has high industrial value.
（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 explained in more detail with reference to Examples, but the present invention is not limited to these Examples in any way.
実施例
〈粗シクロヘキサンの水素化処理〉
シクロヘキサン９３．０重量％、メチルシクロペンテン
類４．５重量％、その他の不純物としてシクロヘキセン
２．０重量％、炭素数４から６の飽和炭化水素０．５重
量％を含有する粗シクロヘキサンを、水素化処理装置に
１．０ｋｇ／Ｆｉｒで供給し、粗シクロヘキサンの水素
化処理を連続的に行った。水素化処理装置には水素化触
媒としてＮｉ触媒（日照ガードラー社製ｃ−３３）５０
０ｇを充填し、入口温度を１２０°Ｃに制御しつつ、５
０気圧の水素圧下で行った。処理後の液を連続的に取り
出し、その組成を分析したところ、シクロヘキサン９４
．９重量％、メチルシクロペンタン４゜６重量％、炭素
数４から６の飽和炭化水素０．５重置％であり、メチル
シクロペンテン類、シクロヘキサンは０．０１重量％以
下であり、はとんど検出されなかった。Example <Hydrogenation treatment of crude cyclohexane> 93.0% by weight of cyclohexane, 4.5% by weight of methylcyclopentenes, 2.0% by weight of cyclohexene as other impurities, and 0.5% by weight of saturated hydrocarbons having 4 to 6 carbon atoms. % of crude cyclohexane was supplied to the hydrogenation apparatus at a rate of 1.0 kg/Fir, and the crude cyclohexane was continuously hydrogenated. Ni catalyst (C-33 manufactured by Nissho Girdler) 50 is used as a hydrogenation catalyst in the hydrogenation equipment.
0g while controlling the inlet temperature to 120°C.
The test was carried out under a hydrogen pressure of 0 atm. After the treatment, the liquid was continuously taken out and its composition was analyzed, and it was found that cyclohexane 94
．． 9% by weight, 4.6% by weight of methylcyclopentane, 0.5% by weight of saturated hydrocarbons having 4 to 6 carbon atoms, and 0.01% by weight or less of methylcyclopentenes and cyclohexane. Not detected.
〈蒸留による高純度シクロヘキサンの取得〉上記の水素
化処理を経た液を、濃縮部２０段、回収部２０段を有す
る蒸留塔に１．０ｋｇ／Ｈｒで連続的に供給し、シクロ
ヘキサンの精製を行った。<Obtaining high-purity cyclohexane by distillation> The liquid subjected to the above hydrogenation treatment was continuously supplied at 1.0 kg/Hr to a distillation column having 20 stages of concentration section and 20 stages of recovery section to purify cyclohexane. Ta.
還流比は４０で行い、塔、貝から約０．０９ｋｇ／Ｈｒ
で留出液を連続的に抜き出し、その組成を分析したとこ
ろ、シクロヘキサン４４．７重量％、メチルシクロペン
タン４９．９重量％、炭素数４から６の飽和炭化水素５
．４重量％であった。このとき塔底から連続的に採取さ
れる液の組成は、シクロヘキサン９９．９７重量％、メ
チルシクロペンタン０．０３重量％であり、極めて高純
度のシクロヘキサンを取得することができた。The reflux ratio was 40, and about 0.09 kg/Hr from the tower and shellfish.
The distillate was extracted continuously and its composition was analyzed, and the composition was found to be 44.7% by weight of cyclohexane, 49.9% by weight of methylcyclopentane, and 5% by weight of saturated hydrocarbons having 4 to 6 carbon atoms.
．． It was 4% by weight. The composition of the liquid continuously collected from the bottom of the column at this time was 99.97% by weight of cyclohexane and 0.03% by weight of methylcyclopentane, making it possible to obtain extremely high purity cyclohexane.
比較例
水素化処理を行わず、実施例と同し粗シクロヘキサンを
実施例と同様にして蒸留操作を行った。Comparative Example The same crude cyclohexane as in the example was distilled in the same manner as in the example without hydrogenation treatment.
塔底から連続的に採取されるシクロヘキサンの純度は粗
シクロヘキサン並であり、炭素数４から６の飽和炭化水
素は塔頂に除去されるものの、メチルシクロペンテン類
はほとんど減少せず、粗シクロヘキサンの精製はできな
かった。The purity of cyclohexane that is continuously collected from the bottom of the column is comparable to that of crude cyclohexane, and although saturated hydrocarbons with 4 to 6 carbon atoms are removed at the top of the column, methylcyclopentenes are hardly reduced, and the purification of crude cyclohexane is I couldn't.
（ほか１名）(1 other person)
Claims (1)
ら高純度のシクロヘキサンを採取するに際し、該粗シク
ロヘキサンを触媒の存在下に水素化処理をしてメチルシ
クロペンテン類をメチルシクロペンタンとし、次に蒸留
によって塔頂よりメチルシクロペンタンを分離除去する
ことを特徴とするシクロヘキサンの精製方法。When extracting highly pure cyclohexane from crude cyclohexane containing methylcyclopentenes, the crude cyclohexane is hydrogenated in the presence of a catalyst to convert methylcyclopentenes into methylcyclopentane, and then methyl is distilled from the top of the column. A method for purifying cyclohexane, characterized by separating and removing cyclopentane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2087461A JPH0649660B2 (en) | 1990-04-03 | 1990-04-03 | Cyclohexane purification method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2087461A JPH0649660B2 (en) | 1990-04-03 | 1990-04-03 | Cyclohexane purification method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03287548A true JPH03287548A (en) | 1991-12-18 |
| JPH0649660B2 JPH0649660B2 (en) | 1994-06-29 |
Family
ID=13915521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2087461A Expired - Lifetime JPH0649660B2 (en) | 1990-04-03 | 1990-04-03 | Cyclohexane purification method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0649660B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002308813A (en) * | 2001-04-05 | 2002-10-23 | Nippon Petrochemicals Co Ltd | High purity diisopropyl ether and method for producing the same |
| KR20160148598A (en) * | 2014-04-22 | 2016-12-26 | 바스프 에스이 | Process for preparing cyclohexane from benzene and methylcyclopentane with upstream benzene hydrogenation |
| CN106397088A (en) * | 2016-09-13 | 2017-02-15 | 中国天辰工程有限公司 | High-efficiency refining method for making cyclohexanone and producing cyclohexane as by-product by cyclohexene method |
| CN113248341A (en) * | 2021-05-21 | 2021-08-13 | 重庆华峰化工有限公司 | Device and process for preparing methylcyclopentane from cyclohexene |
-
1990
- 1990-04-03 JP JP2087461A patent/JPH0649660B2/en not_active Expired - Lifetime
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002308813A (en) * | 2001-04-05 | 2002-10-23 | Nippon Petrochemicals Co Ltd | High purity diisopropyl ether and method for producing the same |
| JP4687849B2 (en) * | 2001-04-05 | 2011-05-25 | Ｊｘ日鉱日石エネルギー株式会社 | High purity diisopropyl ether and process for producing the same |
| KR20160148598A (en) * | 2014-04-22 | 2016-12-26 | 바스프 에스이 | Process for preparing cyclohexane from benzene and methylcyclopentane with upstream benzene hydrogenation |
| JP2017517495A (en) * | 2014-04-22 | 2017-06-29 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Method for producing cyclohexane from benzene and methylcyclopentane by pre-connecting benzene hydrogenation |
| US9873646B2 (en) | 2014-04-22 | 2018-01-23 | Basf Se | Process for preparing cyclohexane from benzene and methylcyclopentane with upstream benzene hydrogenation |
| CN106397088A (en) * | 2016-09-13 | 2017-02-15 | 中国天辰工程有限公司 | High-efficiency refining method for making cyclohexanone and producing cyclohexane as by-product by cyclohexene method |
| CN106397088B (en) * | 2016-09-13 | 2019-05-14 | 中国天辰工程有限公司 | A kind of method of the cyclohexene method preparing cyclohexanone by-product hexamethylene effectively refining |
| CN113248341A (en) * | 2021-05-21 | 2021-08-13 | 重庆华峰化工有限公司 | Device and process for preparing methylcyclopentane from cyclohexene |
| CN113248341B (en) * | 2021-05-21 | 2023-11-24 | 重庆华峰化工有限公司 | Device and process for preparing methylcyclopentane from cyclohexene |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0649660B2 (en) | 1994-06-29 |
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