JPS6251248B2 - - Google Patents
Info
- Publication number
- JPS6251248B2 JPS6251248B2 JP13166279A JP13166279A JPS6251248B2 JP S6251248 B2 JPS6251248 B2 JP S6251248B2 JP 13166279 A JP13166279 A JP 13166279A JP 13166279 A JP13166279 A JP 13166279A JP S6251248 B2 JPS6251248 B2 JP S6251248B2
- Authority
- JP
- Japan
- Prior art keywords
- isopropenylphenol
- parts
- crude
- distillation
- distillate
- 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
Links
- REWLXMVGEZMKSG-UHFFFAOYSA-N 3-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC(O)=C1 REWLXMVGEZMKSG-UHFFFAOYSA-N 0.000 claims description 59
- 238000000034 method Methods 0.000 claims description 25
- 238000004821 distillation Methods 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- WHGXZPQWZJUGEP-UHFFFAOYSA-N 2-prop-1-enylphenol Chemical compound CC=CC1=CC=CC=C1O WHGXZPQWZJUGEP-UHFFFAOYSA-N 0.000 claims 1
- UOUMSRHFISCLAL-UHFFFAOYSA-N hydrogen peroxide 2-(3-propan-2-ylphenyl)propan-2-ol Chemical compound OO.CC(C)C1=CC=CC(C(C)(C)O)=C1 UOUMSRHFISCLAL-UHFFFAOYSA-N 0.000 claims 1
- 229930015698 phenylpropene Natural products 0.000 claims 1
- 239000007788 liquid Substances 0.000 description 18
- 238000011084 recovery Methods 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 5
- VLJSLTNSFSOYQR-UHFFFAOYSA-N 3-propan-2-ylphenol Chemical compound CC(C)C1=CC=CC(O)=C1 VLJSLTNSFSOYQR-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical class CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 2
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- -1 distillate liquid ) Chemical compound 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- UNEATYXSUBPPKP-UHFFFAOYSA-N 1,3-Diisopropylbenzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1 UNEATYXSUBPPKP-UHFFFAOYSA-N 0.000 description 1
- KNCICOZTHWGRMY-UHFFFAOYSA-N 3-(2-hydroxypropan-2-yl)phenol Chemical compound CC(C)(O)C1=CC=CC(O)=C1 KNCICOZTHWGRMY-UHFFFAOYSA-N 0.000 description 1
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical class CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明はｍ―イソプロペニルフエノールの精製
法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for purifying m-isopropenylphenol.
ｍ―イソプロペニルフエノールは、工業的には
ジイソプロピルベンゼンの酸化により得られるｍ
―（２―ヒドロキシ―２―プロピル）キユメンヒ
ドロペルオキシド（以下ｍ―CHPOと称す）を酸
分解することにより得られるが、この分解液中に
はｍ―イソプロペニルフエノールの他にアセト
ン、イソプロピルフエノール、ヒドロキシアセト
フエノン、ジイソプロペニルベンゼン、その他タ
ール化物および溶媒（たとえばメチルイソブチル
ケトン）などが多数含有されており、かかる分解
液よりｍ―イソプロペニルフエノールを効率よく
精製、回収することが重要な課題となつていた。 m-isopropenylphenol is industrially obtained by oxidation of diisopropylbenzene.
It is obtained by acid decomposition of -(2-hydroxy-2-propyl)kyumene hydroperoxide (hereinafter referred to as m-CHPO), but this decomposition solution contains acetone and isopropylphenol in addition to m-isopropenylphenol. , hydroxyacetophenone, diisopropenylbenzene, other tar compounds and solvents (e.g. methyl isobutyl ketone), etc., and it is important to efficiently purify and recover m-isopropenylphenol from such decomposition liquid. This had become an issue.
ところで、従来よりビニール基を有するフエノ
ール類の精製は、かかるフエノール類が熱により
重合し易いため、蒸留法は避け、抽出、晶析法な
どにより行なわれているが、この方法では操作が
煩雑であり、安価に効率よく目的物を精製、回収
することは困難であつた。 By the way, conventionally, phenols having a vinyl group have been purified by extraction, crystallization, etc., avoiding distillation because such phenols are easily polymerized by heat, but this method requires complicated operations. Therefore, it has been difficult to efficiently purify and recover the target product at low cost.
このようなことから、本発明者らはジイソプロ
ピルベンゼンの酸化によるｍ―CHPOを経由して
製造される粗ｍ―イソプロペニルフエノールの精
製法として、操作が容易な蒸留法に着目し、該方
法について種々検討の結果、ｍ―CHPOの酸分解
液を中和後、溶媒等の低沸点留分を蒸留等により
除去（軽沸カツト工程）して得られる粗ｍ―イソ
プロペニルフエノール（たとえば蒸留缶液）は加
熱により生成したものと思われる有機酸（たとえ
ば酪酸、吉草酸など）によりそのPHが低下し、こ
れをそのまま次の蒸留工程に用いれば、蒸留中に
ｍ―イソプロペニルフエニルの重合が激しくな
り、純度よく、かつ高収率でｍ―イソプロペニル
フエノールを回収することができなくなるが、蒸
留前に予じめｍ―イソプロペニルフエノールのPH
（但し、粗ｍ―イソプロペニルフエノールに対し
て0.5重量倍の水を加え、振盪分液後の水層のPH
を意味する。以下同じ）を５〜９の範囲に調整処
理したのち、蒸留することにより、目的物が殆ん
ど重合することなく、純度よく、かつ効率よく回
収できることを見出し、本発明に至つた。 For this reason, the present inventors focused on an easy-to-operate distillation method as a method for purifying crude m-isopropenylphenol produced via m-CHPO by oxidation of diisopropylbenzene, and developed the method. As a result of various studies, we found that crude m-isopropenylphenol (e.g., distillate liquid ), its pH decreases due to organic acids (e.g. butyric acid, valeric acid, etc.) that are thought to have been generated by heating, and if this is used as is in the next distillation process, polymerization of m-isopropenyl phenyl will occur during distillation. However, the pH of m-isopropenylphenol must be adjusted in advance before distillation.
(However, add 0.5 times the weight of water to crude m-isopropenylphenol, and PH of the aqueous layer after shaking and liquid separation.
means. The present inventors have discovered that the target product can be efficiently recovered in high purity with almost no polymerization by adjusting the target product to a value in the range of 5 to 9 and then distilling it, leading to the present invention.
すなわち、本発明はイソプロピルベンゼンの酸
化により得られるｍ―（２―ヒドロキシ―２―プ
ロピル）キユメンヒドロペルオキシドを酸分解
し、中和後、低沸点成分を除去したのちの粗ｍ―
イソプロペニルフエノールからｍ―イソプロペニ
ルフエノールを蒸留法により精製、回収するにあ
たり、蒸留前に予め粗ｍ―イソプロペニルフエノ
ールのPH（但し、粗ｍ―イソプロペニルフエノー
ルに対して0.5重量倍の水を加え、振盪分液後の
水層のPHを意味する）を５〜９に調整処理するこ
とを特徴とするｍ―イソプロペニルフエノールの
精製法である。 That is, the present invention is a crude m-
When purifying and recovering m-isopropenylphenol from isopropenylphenol by distillation, the pH of the crude m-isopropenylphenol (however, 0.5 times the weight of water relative to the crude m-isopropenylphenol is added before distillation) This is a method for purifying m-isopropenylphenol, which is characterized by adjusting the pH of the aqueous layer after shaking and separation to 5 to 9.
本発明におけるPHの調整は、通常蒸留前に予め
行なわれるが、蒸留時にPH調整剤を缶液中に供給
し、蒸留系内でPHを調整させることもできる。 The PH adjustment in the present invention is usually carried out in advance before distillation, but it is also possible to adjust the PH within the distillation system by supplying a PH adjusting agent into the bottom liquid during distillation.
PHの調整法には特に制限されないが、通常は
NaOH、KOH、Na2CO3、K2CO3などのアルカリ
性物質を水溶液状または固体状で粗ｍ―イソプロ
ペニルフエノールと接触させることにより行われ
る。 There are no particular restrictions on the method of adjusting PH, but usually
This is carried out by contacting an alkaline substance such as NaOH, KOH, Na 2 CO 3 or K 2 CO 3 in the form of an aqueous solution or solid with crude m-isopropenylphenol.
本発明において、PHを５〜９の範囲に調整する
ことは極めて重要であり、蒸留前の粗ｍ―イソプ
ロペニルフエノールのPHが５未満の場合には蒸留
時に急激にｍ―イソプロペニルフエノールの重合
が起こり、またPHが９を越えも乙同様に重合が起
き易くなつて、精製効果が低下する。 In the present invention, it is extremely important to adjust the pH to a range of 5 to 9. If the pH of crude m-isopropenylphenol before distillation is less than 5, m-isopropenylphenol will rapidly polymerize during distillation. occurs, and if the pH exceeds 9, polymerization tends to occur as well, reducing the purification effect.
本発明は、このように粗ｍ―イソプロペニルフ
エノールによりｍ―イソプロペニルフエノールを
蒸留法により精製、回収するにあたり、蒸留前に
予め粗ｍ―イソプロペニルフエノールのPHを５〜
９の範囲に調整することを必須条件とするもので
あつて、その具体的な精製方法としてはたとえば
以下の方法が例示される。 In the present invention, when purifying and recovering m-isopropenylphenol from crude m-isopropenylphenol by a distillation method, the pH of the crude m-isopropenylphenol is adjusted to 5 to 5 before distillation.
The essential condition is to adjust the content to within the range of 9. Specific purification methods include the following methods, for example.
(1) 粗ｍ―イソプロペニルフエノールをPH調整し
たのち精留してｍ―イソプロペニルフエノール
を回収する方法。(1) A method of adjusting the pH of crude m-isopropenylphenol and then rectifying it to recover m-isopropenylphenol.
(2) 粗ｍ―イソプロペニルフエノールをPH調整し
たのち蒸留してｍ―イソプロペニルフエノール
留分を留出させて不純物として含有されている
高沸点物（タール状物等）を除去し（脱タール
工程）、上記留出液について再度PH調整したの
ち精留してｍ―イソプロペニルフエノールを回
収する方法。(2) After adjusting the pH of crude m-isopropenylphenol, distill it to distill out the m-isopropenylphenol fraction to remove high-boiling substances (tar-like substances, etc.) contained as impurities (detarring). Step), a method in which the pH of the above distillate is adjusted again and then rectified to recover m-isopropenylphenol.
(3) 前(2)項の脱タールした留出液を有機溶媒の存
在下にアルカリ水で抽出処理し、OH基等のな
いジイソプロペニルベンゼンなどを有機溶媒層
に、水溶性のアルカリ塩となる化合物（たとえ
ばｍ―イソプロペニルフエノール、イソプロピ
ルフエノールなど）をアルカリ塩としてアルカ
リ水に抽出し、このアルカリ水を有機溶媒の存
在下に酸析して溶媒層に抽出し、溶媒を蒸留分
液後、PHを５〜９に調整したのち精留してｍ―
イソプロペニルフエノールを回収する方法。(3) Extract the detarred distillate from (2) above with alkaline water in the presence of an organic solvent, add diisopropenylbenzene, etc., which does not have OH groups, etc. to the organic solvent layer, and add a water-soluble alkali salt. A compound (for example, m-isopropenylphenol, isopropylphenol, etc.) is extracted into alkaline water as an alkali salt, and this alkaline water is acidified in the presence of an organic solvent to extract the solvent layer, and the solvent is separated by distillation. After that, after adjusting the pH to 5 to 9, it is rectified and m-
Method for recovering isopropenylphenol.
これらの例示された方法のうち、(2)又は(3)項に
示す粗ｍ―イソプロペニルフエノールを脱タール
したのち精留するか、或いは脱タールしたのちア
ルカリ抽出処理を行ない、次いで精留する方法が
好ましい。尚、(2)又は(3)項において、脱タールし
た留出液を精留する前に再びPH調整するのは、脱
タール工程における加熱のために該留出液中に酸
性成分が副生し、これをそのまま精留するとｍ―
イソプロペニルフエノールの重合が起こるためで
ある。 Among these exemplified methods, crude m-isopropenylphenol shown in item (2) or (3) is detarred and then rectified, or detarred and then subjected to alkali extraction treatment, and then rectified. The method is preferred. In addition, in item (2) or (3), the reason why the pH of the detarred distillate is adjusted again before rectification is because acidic components are produced as by-products in the distillate due to heating in the detarring process. However, if this is rectified as it is, m-
This is because polymerization of isopropenylphenol occurs.
もちろん、本発明は上記例示された方法にのみ
適用されるものではなく、具体方法の如何を問わ
ず、蒸留法により粗ｍ―イソプロペニルフエノー
ルを精製、回収する際の全ての蒸留工程について
適用される。 Of course, the present invention is not applied only to the methods exemplified above, but is applicable to all distillation steps when purifying and recovering crude m-isopropenylphenol by distillation, regardless of the specific method. Ru.
かくして、本発明の方法に従つて、粗ｍ―イソ
プロペニルフエノールを蒸留する前に、予めPHを
５〜９の範囲となるようにPH調整を行うことによ
り、蒸留中にｍ―イソプロペニルフエノールが重
合することが極めて少なくなり、高純度、高回収
率でｍ―イソプロペニルフエノールを精製するこ
とができる。 Thus, according to the method of the present invention, by adjusting the pH in advance to a range of 5 to 9 before distilling crude m-isopropenylphenol, m-isopropenylphenol can be reduced during distillation. Polymerization is extremely reduced, and m-isopropenylphenol can be purified with high purity and high recovery rate.
以下、本発明を実施例により説明する。 The present invention will be explained below using examples.
但し、例中部および％とあるのは重量単位を示
す。 However, "Example Middle" and "%" indicate weight units.
実施例 １
ｍ―ジイソプロピルベンゼンの酸化反応液より
得られたｍ―（２―ヒドロキシ―２―プロピル）
キユメンヒドロペルオキシドを含むメチルイソブ
チルケトン溶液を酸性分解して得られた反応液を
NaOH水にてPH７に中和する。Example 1 m-(2-hydroxy-2-propyl) obtained from the oxidation reaction solution of m-diisopropylbenzene
The reaction solution obtained by acidic decomposition of a methyl isobutyl ketone solution containing kyumene hydroperoxide is
Neutralize to pH 7 with NaOH water.
この中和液1000部中にはｍ―イソプロペニルフ
エノール70部、ｍ―（２―ヒドロキシ―２―プロ
ピル）フエノール（以下ｍ―OCAと略す）10
部、ｍ―イソプロピルフエノール５部等が含まれ
ている。 In 1000 parts of this neutralizing solution, 70 parts of m-isopropenylphenol and 10 parts of m-(2-hydroxy-2-propyl)phenol (hereinafter abbreviated as m-OCA) were contained.
1 part, m-isopropylphenol 5 parts, etc.
この中和液を連続精留にてアセトンとメチルイ
ソブチルケトンを回収する。この時の条件は塔頂
100mmHg、缶液温度180℃、缶液滞留時間１時間
である。 This neutralized solution is subjected to continuous rectification to recover acetone and methyl isobutyl ketone. The conditions at this time are the top of the tower.
100 mmHg, can liquid temperature 180°C, can liquid residence time 1 hour.
この様にして得られた軽沸カツトした缶液220
部（この内のｍ―イソプロペニルフエノールは63
部であつた）のPHは4.5であつた。 Light boiling cut can liquid obtained in this way 220
parts (of which m-isopropenylphenol is 63
The pH of the phthalate was 4.5.
この缶液に50％苛性水を0.10部加えてPHを６と
した後脱タールを行つた。条件は回分法にて缶液
温度230℃、圧30mmHg2時間で単蒸留させた。 0.10 part of 50% caustic water was added to this tank liquid to adjust the pH to 6, and then detaring was performed. Simple distillation was carried out using a batch method at a temperature of the can liquid of 230°C and a pressure of 30 mmHg for 2 hours.
これにより留出液155部を回収した（この内の
ｍ―イソプロペニルフエノールは70部であつ
た。）。ここでｍ―イソプロペニルフエノールの回
収率が100％以上となるのは、ｍ―OACの一部が
脱水してｍ―イソプロペニルフエノールになるこ
とと更にタール化物の一部が熱分解してｍ―イソ
プロペニルフエノールになつた為と考える。この
様にして分解液から脱タール留出液までのｍ―イ
ソプロペニルフエノールの回収率は100％であつ
た。 As a result, 155 parts of distillate were recovered (70 parts of which were m-isopropenylphenol). Here, the recovery rate of m-isopropenylphenol is over 100% because part of the m-OAC is dehydrated to become m-isopropenylphenol, and in addition, part of the tar compound is thermally decomposed into m-OAC. -I think it's because it turned into isopropenylphenol. In this manner, the recovery rate of m-isopropenylphenol from the decomposition liquid to the detarred distillate was 100%.
又、軽沸カツトした缶液のPHを９としてのち、
脱タールを上記と同条件で行つたところ留出液
155部を回収した（この内のｍ―イソプロペニル
フエノールは65部であつた。）。分解液から脱ター
ル留出液までのｍ―イソプロペニルフエノールの
回収率は92.9％であつた。 In addition, after setting the pH of the canned liquid that has been cut at a low boil to 9,
When detaring was carried out under the same conditions as above, the distillate
155 parts were recovered (65 parts of which were m-isopropenylphenol). The recovery rate of m-isopropenylphenol from the cracked solution to the detarred distillate was 92.9%.
一方、軽沸カツトした缶液をPH調整を行うこと
なく、そのまま上記と同条件で脱タールを行つた
ところ留出液110部を回収した（この内のｍ―イ
ソプロペニルフエノールは45部であつた）。分解
液から脱タール留出液までのｍ―イソプロペニル
フエノールの回収率は64.3％にとどまつた。 On the other hand, when the bottom liquid that had been cut at a low boiling point was detarred under the same conditions as above without adjusting the pH, 110 parts of distillate was recovered (of which m-isopropenylphenol was 45 parts and Ta). The recovery rate of m-isopropenylphenol from the cracked solution to the detarred distillate remained at 64.3%.
この様にPH調整をしないと分解液から脱タール
留出液までのｍ―イソプロペニルフエノールの回
収率は著しく悪くなる。 If the pH is not adjusted in this way, the recovery rate of m-isopropenylphenol from the decomposition liquid to the detarred distillate will be extremely poor.
実施例 ２
実施例１の方法で回収した脱タール留出液155
部（この内のｍ―イソプロペニルフエノール70
部）のPHは3.5であつた。この脱タール留出液を
50％苛性水を0.14部加えてPHを７に調整した後に
回分法で精留を行つた。条件は圧10mmHg、缶液
温度170℃、理論段Ca20段である。これにより主
留分としてｍ―イソプロペニルフエノールを純度
95％で45部回収した。回収率は64％であつた。Example 2 Detarred distillate 155 recovered by the method of Example 1
parts (of which m-isopropenylphenol 70
The pH of the part) was 3.5. This detarred distillate is
After adjusting the pH to 7 by adding 0.14 parts of 50% caustic water, rectification was carried out using a batch method. The conditions were a pressure of 10 mmHg, a tank liquid temperature of 170°C, and a theoretical stage of Ca 20. This allows m-isopropenylphenol to be purified as the main distillate.
45 copies were collected at 95%. The recovery rate was 64%.
尚この時のｍ―イソプロペニルフエノールの保
持率は85％であつた。又、脱タール留出液のPHを
５に調整した後に同条件で精留を行つたところ主
留分としてｍ―イソプロペニルフエノールを純度
95％で40部回収した。回収率は57％、保持率は78
％あつた。 The retention rate of m-isopropenylphenol at this time was 85%. In addition, when the pH of the detarred distillate was adjusted to 5 and rectification was performed under the same conditions, m-isopropenylphenol was found as the main distillate.
40 copies were collected at 95%. Recovery rate is 57%, retention rate is 78
% hot.
一方、脱タールのPHを3.5のままで同条件で精
留を行つたところ、主留分としてｍ―イソプロペ
ニルフエノールを純度90％で７部回収したのみに
とどまつた。回収率は10％、保持率21％と極めて
悪いものであつた。 On the other hand, when rectification was carried out under the same conditions with the detarring pH kept at 3.5, only 7 parts of m-isopropenylphenol with a purity of 90% was recovered as the main fraction. The recovery rate was extremely poor at 10% and the retention rate was 21%.
実施例 ３
実施例１の方法で回収した脱タール液155部
（この内のｍ―イソプロペニルフエノール70部）
を10％アルカリ水300部及びベンゼン100部を加え
てアルカリ抽出し、得られたアルカリ水をベンゼ
ン150部の存在下10％H2SO4にて中和し、PHを７
とした。Example 3 155 parts of detaring liquid recovered by the method of Example 1 (70 parts of m-isopropenylphenol)
was subjected to alkaline extraction by adding 300 parts of 10% alkaline water and 100 parts of benzene, and the resulting alkaline water was neutralized with 10% H 2 SO 4 in the presence of 150 parts of benzene to bring the pH to 7.
And so.
ベンゼンに抽出されたｍ―イソプロペニルフエ
ノールは65部、ｍ―イソプロピルフエノール５部
等であつた。 65 parts of m-isopropenylphenol and 5 parts of m-isopropylphenol were extracted with benzene.
このベンゼン層を常圧にて回分法で単蒸留し
た。缶液温度160℃、１時間で行つた。この様に
して得られた缶液89部（ｍ―イソプロペニルフエ
ノールは62部であつた）のPHは4.5であつた。こ
の缶液に50％アルカリ水を0.04部加えてPH８とし
た後、実施例２と同じ条件にて精留を行い、主留
分としてｍ―イソプロペニルフエノールを純度98
％で45部回収した。 This benzene layer was subjected to simple distillation using a batch method at normal pressure. The test was carried out at a tank liquid temperature of 160°C for 1 hour. The PH of 89 parts of the bottom liquid thus obtained (m-isopropenylphenol was 62 parts) was 4.5. After adding 0.04 part of 50% alkaline water to this bottom liquid to adjust the pH to 8, rectification was performed under the same conditions as in Example 2, and m-isopropenylphenol was obtained as the main fraction with a purity of 98.
%, 45 copies were recovered.
この精留時におけるｍ―イソプロペニルフエノ
ールの回収率は72.6％、保持率は86％であつた。 The recovery rate of m-isopropenylphenol during this rectification was 72.6%, and the retention rate was 86%.
一方PH4.5のまま、アルカリ処理せずに精留を
行つたところ主留分としてｍ―イソプロペニルフ
エノールを純度95％で10部を回収したにとどまつ
た。ｍ―イソプロペニルフエノールの回収率は
13.9％、保持率は25％であつた。 On the other hand, when rectification was carried out at pH 4.5 without alkali treatment, only 10 parts of m-isopropenylphenol with a purity of 95% was recovered as the main fraction. The recovery rate of m-isopropenylphenol is
13.9%, and the retention rate was 25%.
一方、アルカリ処理でPHを10として精留を行つ
たところ主留分としてｍ―イソプロペニルフエノ
ールを純度98％で30部を回収したにとどまつた。
ｍ―イソプロペニルフエノールの回収率48.4％、
保持率60％であつた。 On the other hand, when rectification was carried out with the pH adjusted to 10 through alkali treatment, only 30 parts of m-isopropenylphenol with a purity of 98% was recovered as the main fraction.
Recovery rate of m-isopropenylphenol 48.4%,
The retention rate was 60%.
Claims (1)
るｍ―（２―ヒドロキシ―２―プロピル）キユメ
ンヒドロペルオキシドを酸分解し、中和後、低沸
点成分を除去したのちの粗ｍ―イソプロペニルフ
エノールからｍ―イソプロペニルフエノールを蒸
留法により精製、回収するにあたり、蒸留前に予
め粗ｍ―イソプロペニルフエノールのPH（但し、
粗ｍ―イソプロペニルフエノールに対して0.5重
量倍の水を加え、振盪分液後の水層のPHを意味す
る）を５〜９に調整処理することを特徴とするｍ
―イソプロペニルフエノールの精製法。1 m-(2-hydroxy-2-propyl) cumene hydroperoxide obtained by oxidation of diisopropylbenzene is decomposed with acid, neutralized, and after removing low-boiling components, m-isopropenylphenol is extracted from crude m-isopropenylphenol. When purifying and recovering propenylphenol by distillation, the pH of crude m-isopropenylphenol (however,
m-isopropenylphenol is characterized by adding 0.5 times the weight of water to crude m-isopropenylphenol and adjusting the pH of the aqueous layer after shaking and separation to 5 to 9.
- Purification method of isopropenylphenol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13166279A JPS5655329A (en) | 1979-10-11 | 1979-10-11 | Purification of m-isopropenylphenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13166279A JPS5655329A (en) | 1979-10-11 | 1979-10-11 | Purification of m-isopropenylphenol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5655329A JPS5655329A (en) | 1981-05-15 |
| JPS6251248B2 true JPS6251248B2 (en) | 1987-10-29 |
Family
ID=15063287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13166279A Granted JPS5655329A (en) | 1979-10-11 | 1979-10-11 | Purification of m-isopropenylphenol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5655329A (en) |
-
1979
- 1979-10-11 JP JP13166279A patent/JPS5655329A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5655329A (en) | 1981-05-15 |
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