JPS62263135A - Separation of m-cresol - Google Patents
Separation of m-cresolInfo
- Publication number
- JPS62263135A JPS62263135A JP10304186A JP10304186A JPS62263135A JP S62263135 A JPS62263135 A JP S62263135A JP 10304186 A JP10304186 A JP 10304186A JP 10304186 A JP10304186 A JP 10304186A JP S62263135 A JPS62263135 A JP S62263135A
- Authority
- JP
- Japan
- Prior art keywords
- cresol
- cyclohexane
- mixture
- isomers
- hydroxyphenyl
- 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.)
- Pending
Links
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 238000000926 separation method Methods 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 14
- 150000001896 cresols Chemical class 0.000 claims abstract description 13
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 11
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 abstract description 16
- 229930003836 cresol Natural products 0.000 abstract description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 4
- 238000001914 filtration Methods 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 239000003208 petroleum Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229920003987 resole Polymers 0.000 description 2
- JEFSTMHERNSDBC-UHFFFAOYSA-N 1,2-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC=CCC1(C)O JEFSTMHERNSDBC-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 101100428830 Caenorhabditis elegans mml-1 gene Proteins 0.000 description 1
- 239000005574 MCPA Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000003717 m-cresyl group Chemical group [H]C1=C([H])C(O*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、クレゾール異性体混合物から、ｍ−クレゾー
ルを分離する新規な方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a novel method for separating m-cresol from a mixture of cresol isomers.
一般に、クレゾールの工業的製法としては、タール留分
からるアルカリ抽出法、トルエンの塩素化加水分解法、
トルエンのスルホン化アルカリ溶融法がある。これらの
方法では、いずれも得られる生成物はｏ−、ｍ−、ｐ−
の三種の異性体の混合物である。Generally, industrial methods for producing cresol include alkali extraction from tar fraction, chlorination hydrolysis of toluene,
There is an alkali melting method for sulfonating toluene. In these methods, the products obtained are o-, m-, p-
It is a mixture of three isomers.
一方、クレゾールの用途としては、これらの三種の異性
体混合物としての用途もあるが、これらの特定の異性体
のみが適する用途も多い。混合物としては主に殺菌、防
腐剤に用いられ、０−クレゾールの単独の用途としては
、ＭＣＰ剤（２−メチル−４−クロロフェノキシ酢酸）
を中心とする除草剤向があげられ、ｍ−クレゾール単独
用途としては、スミチオン（０，０−ジメチル−３−メ
チル−４−ニトロフェニルチオリン酸塩）を中心とする
殺虫剤向がある。また、ｐ−クレゾール単独用途として
は、［１ＩＩＴ（２，６−ジーｔ−ブチル−ｐ−クレゾ
ール）を中心とする酸化防止剤や染料向がある。On the other hand, cresol can be used as a mixture of these three isomers, but there are also many uses where only these specific isomers are suitable. As a mixture, it is mainly used as a disinfectant and preservative, and as a single use of 0-cresol, it is used as an MCP agent (2-methyl-4-chlorophenoxyacetic acid).
m-cresol is mainly used as a herbicide, and m-cresol is used alone as an insecticide, mainly sumithion (0,0-dimethyl-3-methyl-4-nitrophenylthiophosphate). In addition, p-cresol can be used alone as an antioxidant and dye, mainly 1IIT (2,6-di-t-butyl-p-cresol).
従って、混合物としての用途に供する場合には前述の生
成りレゾール混合物をそのまま使用できるが、異性体単
独の用途に供するには生成りレゾール混合物から、それ
ぞれの異性体を分離する必要がある。Therefore, when used as a mixture, the above-mentioned product resol mixture can be used as is, but when using the isomers alone, it is necessary to separate each isomer from the product resol mixture.
ところが各異性体の沸点は、ｏ−１９１，０℃、ｍ−２
０２、２℃、ｐ−２０１，９℃となっており、０−クレ
ゾールの蒸留分離は容易であるが、ｍ−、ｐ−の沸点は
近似しており、単なる蒸留で分離することはできない。However, the boiling point of each isomer is o-191.0℃, m-2
02.2°C and p-201.9°C, and it is easy to separate 0-cresol by distillation, but the boiling points of m- and p- are similar and cannot be separated by simple distillation.
５
従来、混合クレゾールよりｍ−クレゾールを分離する方
法としては、まず、Ｏ−クレゾール蒸留分離後、残ｍ−
，ｐ−クレゾールをスルホン化した後、水蒸気分解によ
りｍ−クレゾールを分解分離するという複雑なプロセス
を必要としている。また、ｍ−。5 Conventionally, as a method for separating m-cresol from mixed cresol, first, after separating O-cresol by distillation, the remaining m-cresol was separated by distillation.
, requires a complicated process of sulfonating p-cresol and then decomposing and separating m-cresol by steam decomposition. Also, m-.
ｐ−クレゾールよりｍ−クレゾールを分離する方法とし
て、一旦、ｍ−＊Ｐ一体をブチル化し、その後、ｍ−１
ｐ一体のジブチル化物を精留分離した後、ｍ一体の脱ブ
チル化によりｍ−クレゾールを得る方法もあるが極めて
複雑な工程を要する。As a method for separating m-cresol from p-cresol, m-*P is once butylated, and then m-1
There is a method of obtaining m-cresol by rectifying and separating the dibutylated product of p-unit and then debutylating the m-unit, but this requires an extremely complicated process.
本発明者は、クレゾールの異性体よりｍ−クレゾールを
分離する方法について鋭意研究を行った結果、三種のク
レゾール異性体の中で、特にｍ−クレゾールのみが１．
１−ビス （４−ヒドロキシフェニル）−シクロヘキサ
ンと包接錯体を形成して結晶とじて析出し、他の異性体
と容易に分離できることを見出し、本発明に至ったもの
である。The present inventor conducted intensive research on a method for separating m-cresol from cresol isomers, and found that among the three types of cresol isomers, only m-cresol had 1.
It was discovered that it forms an inclusion complex with 1-bis (4-hydroxyphenyl)-cyclohexane, precipitates as crystals, and can be easily separated from other isomers, leading to the present invention.
即ち本発明は、クレゾール異性体の混合物を、有Ｒ溶媒
中で １．１−ビス （４−ヒドロキシフェニル）シク
ロヘキサンと接触させ、析出するｍ−クレゾールと前記
シクロヘキサンとの包接錯体を分離した後、その包接錯
体を分解することを特徴とするクレゾール異性体混合物
からｍ−クレゾールを分離する方法であり、異性体混合
物からｍ−クレゾールを分離する有利な方法を提供する
ものである。That is, the present invention provides a method for contacting a mixture of cresol isomers with 1,1-bis(4-hydroxyphenyl)cyclohexane in an R solvent to separate the precipitated inclusion complex of m-cresol and the cyclohexane. , a method for separating m-cresol from a mixture of cresol isomers, characterized by decomposing its inclusion complex, and provides an advantageous method for separating m-cresol from a mixture of isomers.
本発明は、ｏ−、ｍ−、ｐ−クレゾールの各種混合物に
適用でき、更に、クレゾール以外の成分を含むクレゾー
ル混合物にも適用できる。The present invention can be applied to various mixtures of o-, m-, and p-cresol, and can also be applied to cresol mixtures containing components other than cresol.
本発明によれば、以上の各種の混合系よりｍ−クレゾー
ルのみを選択的に容易に分離することができることはも
ちろん、クレゾール異性体の分離にも利用できる。According to the present invention, it is possible not only to selectively and easily separate only m-cresol from the various mixed systems described above, but also to separate cresol isomers.
本発明に用いられる１、１−ビス （４−ヒドロキシフ
ェニル）−シクロヘキサンは、シクロヘキサンとフェノ
ールとから工業的に製造されていて容易に入手でき、次
の構造式で示されるものである。1,1-bis(4-hydroxyphenyl)-cyclohexane used in the present invention is industrially produced from cyclohexane and phenol, is easily available, and is represented by the following structural formula.
１、１−ヒス （４−ヒドロキシフェニル）−シクロヘ
キサンの使用量は、クレゾールの異性体混合物中のｍ−
クレゾール１モルに対し、１モル以上、好ましくは２〜
ｌＯモルである。The amount of 1,1-his(4-hydroxyphenyl)-cyclohexane used is the m-
1 mol or more, preferably 2 to 1 mol per mol of cresol
It is 10 mole.
本発明において使用される有機溶媒は、クレゾールの各
異性体および１．１−ビス （４−ヒドロキシフェニル
）−シクロヘキサンとを良く溶解し、かつ生成したｍ−
クレゾールと当該シクロヘキサンとの包接錯体の溶解度
の小さいものが望ましい。具体的には、石油エーテル、
エチルエーテル、クロロホルム、グリコール類、ベンゼ
ン、ヘキサン、アセトニトリル、酢酸エチル等が用いら
れる。有機溶媒の使用量は、１．１−ビス （４−ヒド
ロキシフェニル）シクロヘキサン１ｇに対して一般に２
〜２０ｍ ｌが用いられる。The organic solvent used in the present invention can dissolve each isomer of cresol and 1,1-bis (4-hydroxyphenyl)-cyclohexane well, and the m-
It is desirable that the inclusion complex of cresol and the cyclohexane has low solubility. Specifically, petroleum ether,
Ethyl ether, chloroform, glycols, benzene, hexane, acetonitrile, ethyl acetate, etc. are used. The amount of organic solvent used is generally 2 to 1 g of 1.1-bis(4-hydroxyphenyl)cyclohexane.
~20ml is used.
クレゾール異性体混合物と当該シクロヘキサンとの接触
条件は、通常、温度１０〜５０℃、時間１〜２０時間で
ある。この接触工程により、クレゾール異性体のうち、
ｍ−クレゾールのみが当該シクロヘキサンと包接錯体を
形成し析出してくる。析出した錯体は濾過などの操作に
より、容易に分離できる。回収した錯体を減圧下に加熱
することによりｍ−クレゾールを分離、取得できる。The conditions for contacting the cresol isomer mixture with the cyclohexane are usually a temperature of 10 to 50°C and a time of 1 to 20 hours. Through this contact step, among the cresol isomers,
Only m-cresol forms an inclusion complex with the cyclohexane and precipitates. The precipitated complex can be easily separated by operations such as filtration. By heating the recovered complex under reduced pressure, m-cresol can be separated and obtained.
■−クレゾールを分離した残液は、蒸留等によりクレゾ
ールの他の異性体分離に供することができる。尚、ｍ−
クレゾールを分離した当該シクロヘキサンは再び、本発
明に使用することできる。(2) The residual liquid from which cresol has been separated can be used to separate other isomers of cresol by distillation or the like. Furthermore, m-
The cyclohexane from which the cresol has been separated can be used again in the present invention.
本発明によれば、クレゾール異性体混合物又はクレゾー
ル以外の成分を含むクレゾール混合物の混合系よりｍ−
クレゾールのみを選択的に容易に分離することができる
。また、クレゾール異性体の分離にも利用することがで
きる。According to the present invention, m-
Only cresol can be selectively and easily separated. It can also be used to separate cresol isomers.
以下に実施例を挙げて説明する。 Examples will be described below.
実施例１
ｔ、１−ヒス （４−ヒドロキシフェニル）−シクロヘ
キサン２．０ｇとクレゾール混合物（ｍ−クレゾニル５
４．１％、ｐ−クレゾール２７．３％、２．４−及び２
，５−キシレノール１４．４％、０−クレゾール及び２
．６−キシレノール４．０％） １．、．４７ｇを酢酸
エチル１０ｍ１に溶解し、室温で１２時間放置すると結
晶が析出した。ａα別して得られた結晶を酢酸エチル１
０＋ｎｌで１回、再結晶すると当該シクロヘキサンとｍ
−クレゾールのｌ＝ｌ包接化合物（無色プリズム状結晶
）１．７４ｇが得られた。Example 1 2.0 g of t,1-his (4-hydroxyphenyl)-cyclohexane and a cresol mixture (m-cresonyl 5
4.1%, p-cresol 27.3%, 2.4- and 2
, 5-xylenol 14.4%, 0-cresol and 2
．． 6-xylenol 4.0%) 1. ,．． 47 g was dissolved in 10 ml of ethyl acetate and allowed to stand at room temperature for 12 hours to precipitate crystals. The crystals obtained by aα separation were mixed with ethyl acetate 1
When recrystallized once at 0+nl, the cyclohexane and m
-1.74 g of l=l clathrate of cresol (colorless prismatic crystals) was obtained.
この結晶を減圧下（１０ｍｍｌ１ｇ）、１８０℃で加熱
するとｍ−クレゾール０．４４ｇ （純度９８．５％）
が得られた。When this crystal is heated at 180°C under reduced pressure (10 mml 1 g), 0.44 g of m-cresol (purity 98.5%) is obtained.
was gotten.
Claims (1)
ス（４−ヒドロキシフェニル）−シクロヘキサンと接触
させ、析出するｍ−クレゾールと前記シクロヘキサンと
の包接錯体を分離した後、その包接錯体を分解すること
を特徴とするクレゾール異性体混合物からｍ−クレゾー
ルを分離する方法A mixture of cresol isomers is brought into contact with 1,1-bis(4-hydroxyphenyl)-cyclohexane in an organic solvent to separate the precipitated inclusion complex of m-cresol and the cyclohexane, and then the inclusion complex is separated. A method for separating m-cresol from a cresol isomer mixture, characterized by decomposing
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10304186A JPS62263135A (en) | 1986-05-07 | 1986-05-07 | Separation of m-cresol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10304186A JPS62263135A (en) | 1986-05-07 | 1986-05-07 | Separation of m-cresol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62263135A true JPS62263135A (en) | 1987-11-16 |
Family
ID=14343582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10304186A Pending JPS62263135A (en) | 1986-05-07 | 1986-05-07 | Separation of m-cresol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62263135A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0943598A1 (en) * | 1998-03-20 | 1999-09-22 | Adchemco Corporation | Process for the separation and purification of xylenol isomers |
| WO2004073996A1 (en) * | 2003-02-18 | 2004-09-02 | Sanko Co., Ltd. | 1,2-bis(3-methylphenoxy)ethane composition and thermal recording media made by using the same |
| CN100379580C (en) * | 2003-02-18 | 2008-04-09 | 三光株式会社 | 1,2-bis(3-methylphenoxy)ethane composition and thermal recording media made by using the same |
-
1986
- 1986-05-07 JP JP10304186A patent/JPS62263135A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0943598A1 (en) * | 1998-03-20 | 1999-09-22 | Adchemco Corporation | Process for the separation and purification of xylenol isomers |
| WO2004073996A1 (en) * | 2003-02-18 | 2004-09-02 | Sanko Co., Ltd. | 1,2-bis(3-methylphenoxy)ethane composition and thermal recording media made by using the same |
| CN100379580C (en) * | 2003-02-18 | 2008-04-09 | 三光株式会社 | 1,2-bis(3-methylphenoxy)ethane composition and thermal recording media made by using the same |
| US7566682B2 (en) | 2003-02-18 | 2009-07-28 | Sanko Co., Ltd | 1,2-bis(3-methylphenoxy)ethane composition and thermal recording media made by using the same |
| US7645396B2 (en) | 2003-02-18 | 2010-01-12 | Sanko Co., Ltd. | 1,2-bis(3-methylphenoxy)ethane composition and thermal recording media made by using the same |
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