JP3089780B2 - Method for producing phenol and methyl ethyl ketone - Google Patents
Method for producing phenol and methyl ethyl ketoneInfo
- Publication number
- JP3089780B2 JP3089780B2 JP34497891A JP34497891A JP3089780B2 JP 3089780 B2 JP3089780 B2 JP 3089780B2 JP 34497891 A JP34497891 A JP 34497891A JP 34497891 A JP34497891 A JP 34497891A JP 3089780 B2 JP3089780 B2 JP 3089780B2
- Authority
- JP
- Japan
- Prior art keywords
- sec
- methyl ethyl
- ethyl ketone
- butylbenzene
- phenol
- 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 - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
- C07C407/003—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明はフェノール及びメチルエ
チルケトンの製造方法に関するものである。更に詳しく
は、本発明はｓｅｃ−ブチルベンゼンを出発原料とする
フェノール及びメチルエチルケトンの製造方法に関する
ものである。The present invention relates to a method for producing phenol and methyl ethyl ketone. More specifically, the present invention relates to a method for producing phenol and methyl ethyl ketone using sec-butylbenzene as a starting material.
【０００２】[0002]
【従来の技術】ｓｅｃ−ブチルベンゼンを酸化して得ら
れるｓｅｃ−ブチルベンゼンハイドロパーオキサイドを
主成分とする反応液を蒸留により濃縮し、得られる濃縮
液中のｓｅｃ−ブチルベンゼンハイドロパーオキサイド
を酸性触媒によりフェノールとメチルエチルケトンに分
解する技術は公知である（特開昭４８−８０５２４号公
報）。2. Description of the Related Art A reaction solution containing sec-butylbenzene hydroperoxide as a main component obtained by oxidizing sec-butylbenzene is concentrated by distillation, and sec-butylbenzene hydroperoxide in the obtained concentrate is acidified. The technique of decomposing into phenol and methyl ethyl ketone with a catalyst is known (JP-A-48-80524).
【０００３】[0003]
【発明が解決しようとする課題】上記の方法により得ら
れたフェノールとメチルエチルケトンの混合液からフェ
ノールとメチルエチルケトンを各々分離するためには、
該混合液を蒸留に付す必要がある。しかしながら、該混
合液には酸化工程及び分解工程で副生する脂肪酸類と中
和工程で使用するアルカリとに起因する少量の脂肪酸塩
類、並びに分解工程で使用する酸性触媒と中和工程で使
用するアルカリとに起因する無機塩類が含有されてお
り、該混合液をそのまま蒸留に付した場合には、リボイ
ラーその他の蒸留装置の各所に該脂肪酸塩類及び無機塩
類が析出・堆積し、リボイラーの熱効率を低下させる、
閉塞により蒸留操作が不可能になるといった問題を生じ
る。In order to separate phenol and methyl ethyl ketone from a mixture of phenol and methyl ethyl ketone obtained by the above method, respectively:
The mixture must be subjected to distillation. However, the mixed solution contains a small amount of fatty acid salts caused by the fatty acids produced as a by-product in the oxidation step and the decomposition step and the alkali used in the neutralization step, and is used in the acid catalyst used in the decomposition step and the neutralization step. Inorganic salts derived from alkalis are contained, and when the mixture is subjected to distillation as it is, the fatty acid salts and inorganic salts are deposited and deposited at various points in a reboiler and other distillation apparatuses, thereby reducing the thermal efficiency of the reboiler. Lower,
Blockage causes a problem that the distillation operation becomes impossible.
【０００４】かかる現状に鑑み、本発明が解決しようと
する課題は、ｓｅｃ−ブチルベンゼンを酸化して得られ
るｓｅｃ−ブチルベンゼンハイドロパーオキサイドを主
成分とする酸化反応液を蒸留により濃縮し、得られる濃
縮液中のｓｅｃ−ブチルベンゼンハイドロパーオキサイ
ドを酸性触媒によりフェノールとメチルエチルケトンに
分解し、得られる分解液中のフェノールとメチルエチル
ケトンとを各々蒸留により回収するフェノール及びメチ
ルエチルケトンの製造方法であって、蒸留に付する液中
の脂肪酸塩類及び無機塩類を極めて低い水準に維持で
き、よって蒸留装置各所への脂肪酸塩類及び無機塩類の
析出を防止し、熱効率の点において優れ、かつ閉塞によ
り蒸留操作を中断せざるを得ないといった問題を伴なわ
ず、長期間にわたって安定な連続運転が可能であるとい
う優れたフェノール及びメチルエチルケトンの製造方法
を提供する点に存するものである。In view of the current situation, the problem to be solved by the present invention is to concentrate an oxidation reaction solution containing sec-butylbenzene hydroperoxide obtained by oxidizing sec-butylbenzene as a main component by distillation, and to concentrate the solution. A method for producing phenol and methyl ethyl ketone, comprising decomposing sec-butylbenzene hydroperoxide in the obtained concentrated solution into phenol and methyl ethyl ketone with an acidic catalyst, and recovering the phenol and methyl ethyl ketone in the obtained decomposed solution by distillation, respectively. Can maintain the fatty acid salts and inorganic salts in the solution to an extremely low level, thereby preventing the precipitation of fatty acid salts and inorganic salts at various places in the distillation apparatus, being excellent in terms of thermal efficiency, and interrupting the distillation operation due to blockage. For a long period of time without the In which resides in providing excellent phenol and methyl ethyl ketone of a manufacturing method that are possible stable continuous operation.
【０００５】[0005]
【課題を解決するための手段】すなわち、本発明は、ｓ
ｅｃ−ブチルベンゼンを出発原料としてフェノール及び
メチルエチルケトンを製造する方法であって、下記の工
程を含むことを特徴とするフェノール及びメチルエチル
ケトンの製造方法に係るものである。 酸化工程：ｓｅｃ−ブチルベンゼンを酸化してｓｅｃ−
ブチルベンゼンハイドロパーオキサイドを主成分とする
酸化反応液を得る工程 濃縮工程：酸化反応液を蒸留により濃縮し、塔底部から
ｓｅｃ−ブチルベンゼンハイドロパーオキサイドを主成
分とする塔底液を得、塔頂部からｓｅｃ−ブチルベンゼ
ンを主成分とする留出液を得る工程 分解工程：濃縮工程の塔底液を酸性触媒と接触させるこ
とにより、ｓｅｃ−ブチルベンゼンハイドロパーオキサ
イドをフェノールとメチルエチルケトンに分解する工程 中和工程：分解工程で得られた分解液をアルカリ水溶液
により中和し、油層と水層に分離し、水層の一部を再度
中和工程へリサイクルする工程 水洗工程：中和工程で得られた油層を水洗し、フェノー
ル及びメチルエチルケトンを主成分とする油層と水層に
分離し、水層の一部又は全部を中和工程へリサイクルす
る工程 精製工程：水洗工程で得られた油層を蒸留に付し、フェ
ノールとメチルエチルケトンを分離する工程That is, the present invention provides a s
A method for producing phenol and methyl ethyl ketone using ec-butylbenzene as a starting material, which relates to a method for producing phenol and methyl ethyl ketone, comprising the following steps. Oxidation step: sec-butylbenzene is oxidized to sec-
Step of obtaining an oxidation reaction solution containing butylbenzene hydroperoxide as a main component Concentration step: Concentrating the oxidation reaction solution by distillation to obtain a bottom solution containing sec-butylbenzene hydroperoxide as a main component from the bottom of the column. Step of obtaining a distillate containing sec-butylbenzene as the main component from the top Decomposition step: a step of decomposing sec-butylbenzene hydroperoxide into phenol and methyl ethyl ketone by bringing the bottom liquid of the concentration step into contact with an acidic catalyst. Neutralization step: The decomposition solution obtained in the decomposition step is neutralized with an aqueous alkali solution, separated into an oil layer and an aqueous layer, and a part of the aqueous layer is recycled to the neutralization step. The separated oil layer is washed with water, separated into an oil layer mainly composed of phenol and methyl ethyl ketone and an aqueous layer, and a part or all of the aqueous layer is neutralized. Refining process: A process in which the oil layer obtained in the water washing process is subjected to distillation to separate phenol and methyl ethyl ketone.
【０００６】以下詳細に説明する。本発明の酸化工程と
は、ｓｅｃ−ブチルベンゼンを酸化してｓｅｃ−ブチル
ベンゼンハイドロパーオキサイドを主成分とする酸化反
応液を得る工程であり、たとえば次のとおり行われる。
すなわち、液体のｓｅｃ−ブチルベンゼンを、９０〜１
５０℃の温度、１〜１０ｋｇ／ｃｍ2 Ｇの圧力下、酸素
含有ガスと接触させることによりｓｅｃ−ブチルベンゼ
ンハイドロパーオキサイドとする。The details will be described below. The oxidation step of the present invention is a step of oxidizing sec-butylbenzene to obtain an oxidation reaction solution containing sec-butylbenzene hydroperoxide as a main component, and is performed, for example, as follows.
That is, 90 sec.
It is made into sec-butylbenzene hydroperoxide by contacting with an oxygen-containing gas at a temperature of 50 ° C. and a pressure of 1 to 10 kg / cm 2 G.
【０００７】本発明の濃縮工程とは、酸化反応液を蒸留
により濃縮し、塔底部からｓｅｃ−ブチルベンゼンハイ
ドロパーオキサイドを主成分とする塔底液を得、塔頂部
からｓｅｃ−ブチルベンゼンを主成分とする留出液を得
る工程である。濃縮工程における蒸留の条件は、要する
にｓｅｃ−ブチルベンゼンハイドロパーオキサイドを主
成分とする塔底液とｓｅｃ−ブチルベンゼンを主成分と
する留出液が得られるように設定すればよく、たとえば
塔底温度５０〜１５０℃、塔頂圧力１〜２００ｔｏｒｒ
があげられる。In the concentration step of the present invention, the oxidation reaction solution is concentrated by distillation to obtain a column bottom liquid containing sec-butylbenzene hydroperoxide as a main component from the column bottom, and sec-butylbenzene mainly from the column top. This is a step of obtaining a distillate as a component. The distillation conditions in the concentration step may be set so that a bottom liquid mainly composed of sec-butylbenzene hydroperoxide and a distillate mainly composed of sec-butylbenzene are obtained. Temperature 50-150 ° C, overhead pressure 1-200 torr
Is raised.
【０００８】本発明の分解工程とは、濃縮工程の塔底液
を酸性触媒と接触させることにより、ｓｅｃ−ブチルベ
ンゼンハイドロパーオキサイドをフェノールとメチルエ
チルケトンに分解する工程である。酸性触媒としては、
硫酸、無水硫酸、過塩素酸、リン酸などが用いられる。
酸性触媒の使用量は、通常０．０１〜１ｗｔ％であり、
温度は通常５０〜１００℃の範囲である。[0008] The decomposition step of the present invention is a step of decomposing sec-butylbenzene hydroperoxide into phenol and methyl ethyl ketone by bringing the bottom liquid of the concentration step into contact with an acidic catalyst. As the acidic catalyst,
Sulfuric acid, sulfuric anhydride, perchloric acid, phosphoric acid and the like are used.
The amount of the acidic catalyst used is usually 0.01 to 1 wt%,
The temperature is usually in the range of 50-100C.
【０００９】本発明の中和工程とは、分解工程で得られ
た分解液をアルカリ水溶液により中和し、油層と水層に
分離し、水層の一部を再度中和工程の入口へリサイクル
する工程である。中和のために用いられるアルカリとし
ては、ナトリウム、カリウム、リチウムなどの水酸化
物、炭酸塩、重炭酸塩などが使用できる。アルカリの使
用量は、水層のｐＨを通常５〜１１、好ましくは６〜１
０に維持するのに十分な量である。温度は常温〜９０
℃、油層／水層の重量比は０．５〜５が好ましい。中和
工程は、中和されるべき液層とアルカリ水溶液とを十分
に接触させ、その後油層と水層とを分離できればよく、
たとえば攪拌器付の槽、ラインミキサー、パイプミキサ
ーなどが用いられる。中和工程においては、排水量を減
少させるために、中和工程で使用後の水層の一部を再度
中和工程でリサイクル使用する。その結果、中和工程の
塩濃度は上昇するが、通常１〜３０ｗｔ％の塩濃度に維
持することが好ましい。中和工程で得られた油層は次の
水洗工程へ送られ、一方水層は、その一部を中和工程へ
リサイクルし、残りは廃棄される。[0009] The neutralization step of the present invention is to neutralize the decomposition solution obtained in the decomposition step with an aqueous alkali solution, separate the oil layer and the aqueous layer, and recycle a part of the aqueous layer to the inlet of the neutralization step again. This is the step of performing As the alkali used for neutralization, hydroxides such as sodium, potassium and lithium, carbonates, bicarbonates and the like can be used. The amount of the alkali used is usually 5 to 11, preferably 6 to 1 pH of the aqueous layer.
This is an amount sufficient to maintain zero. Temperature is normal temperature to 90
C., and the weight ratio of the oil layer / water layer is preferably 0.5 to 5. The neutralization step is sufficient if the liquid layer to be neutralized and the aqueous alkali solution are sufficiently brought into contact with each other, and thereafter the oil layer and the aqueous layer can be separated,
For example, a tank with a stirrer, a line mixer, a pipe mixer and the like are used. In the neutralization step, in order to reduce the amount of wastewater, a part of the water layer used in the neutralization step is recycled and used again in the neutralization step. As a result, the salt concentration in the neutralization step increases, but it is generally preferable to maintain the salt concentration at 1 to 30 wt%. The oil layer obtained in the neutralization step is sent to the next washing step, while part of the aqueous layer is recycled to the neutralization step, and the rest is discarded.
【００１０】本発明の水洗工程とは、中和工程で得られ
た油層を水洗し、フェノール及びメチルエチルケトンを
主成分とする油層と水層に分離し、水層の一部又は全部
を中和工程へリサイクルする工程である。従来、ハイド
ロパーオキサイドの分解によりフェノールを製造するプ
ロセスにおいて、中和後に水洗が実施された例はない。
すなわち、クメンハイドロパーオキサイドからフェノー
ルを製造するプロセスでは、副生するアセトンが水と無
制限に混和するため、水洗を行うことはできなかった。
これに対し、本発明においては、副生するメチルエチル
ケトンが水と分液するため、水洗が可能なのである。The water washing step of the present invention is to wash the oil layer obtained in the neutralization step, separate it into an oil layer containing phenol and methyl ethyl ketone as a main component and an aqueous layer, and neutralize a part or all of the aqueous layer. This is the process of recycling to Conventionally, in a process for producing phenol by decomposing a hydroperoxide, there is no example of washing with water after neutralization.
That is, in the process of producing phenol from cumene hydroperoxide, the by-product acetone was mixed with water indefinitely, so that water could not be washed.
On the other hand, in the present invention, the by-produced methyl ethyl ketone is separated from water, so that it can be washed with water.
【００１１】水洗のために新たに水洗工程へ加えられる
水の量は、中和工程で得られた油層に対して、通常２〜
１０ｗｔ％である。温度は常温〜９０℃、油層／水層の
重量比は０．５〜５が好ましい。水洗工程は水洗される
べき液層と水洗水とを十分に接触させ、その後油層と水
層とを分離できればよく、たとえば攪拌器付の槽、ライ
ンミキサー、パイプミキサーなどが用いられる。ここで
得られた油層は精製工程へ送られる。一方、水層の一部
又は全部は前工程の中和工程へリサイクルされる。この
ことにより、中和工程の液の塩濃度を好ましい範囲に制
御できる。本発明によると、油層中の脂肪酸塩類及び無
機塩類は極めて効率的に水層へ除去され、油層中の脂肪
酸塩類及び無機塩類は、通常数ｐｐｍ以下に維持され得
る。The amount of water newly added to the rinsing step for rinsing is usually 2 to 2 with respect to the oil layer obtained in the neutralization step.
10 wt%. The temperature is preferably from room temperature to 90 ° C., and the weight ratio of the oil layer / water layer is preferably 0.5 to 5. In the water washing step, it is sufficient that the liquid layer to be washed and the washing water are sufficiently brought into contact with each other, and thereafter, the oil layer and the water layer can be separated. The oil layer obtained here is sent to a refining process. On the other hand, part or all of the aqueous layer is recycled to the neutralization step in the previous step. This makes it possible to control the salt concentration of the solution in the neutralization step to a preferred range. According to the present invention, fatty acid salts and inorganic salts in the oil layer are very efficiently removed to the aqueous layer, and the fatty acid salts and inorganic salts in the oil layer can be generally maintained at a few ppm or less.
【００１２】本発明の精製工程とは、水洗工程で得られ
た油層を蒸留に付し、フェノールとメチルエチルケトン
を分離する工程であり、通常複数の蒸留塔により実現さ
れる。The purification step of the present invention is a step of subjecting the oil layer obtained in the water washing step to distillation to separate phenol and methyl ethyl ketone, and is usually realized by a plurality of distillation columns.
【００１３】本発明によると、精製工程に付される油層
に含まれる脂肪酸塩類及び無機塩類は十分に除去されて
いるので、精製工程の蒸留塔のリボイラーその他への脂
肪酸塩類及び無機塩類の堆積がなく、優れた熱効率の
下、長期的に安定した精製操作が可能となる。かかる効
果は、大規模下、長期連続運転を要求される工業的製造
プロセスにおいて、特に重要不可欠なものとなる。According to the present invention, since the fatty acid salts and inorganic salts contained in the oil layer subjected to the refining step are sufficiently removed, the accumulation of the fatty acid salts and inorganic salts on the reboiler and the like of the distillation column in the refining step is prevented. And a long-term stable purification operation is possible under excellent thermal efficiency. This effect is particularly important in an industrial manufacturing process that requires long-term continuous operation on a large scale.
【００１４】[0014]
【実施例】次に、実施例により本発明を説明する。 実施例１ 容積５．２ｌの分解反応装置に、ｓｅｃ−ブチルベンゼ
ンハイドロパーオキサイド６１．５ｗｔ％、ｓｅｃ−ブ
チルベンゼン１６．７ｗｔ％、アセトフェノン１０．６
ｗｔ％を含有する濃縮液１２．８ｋｇ／ｈ及び９８ｗｔ
％硫酸１０ｇ／ｈを供給し、６５℃の温度で分解反応を
実施した。得られた分解液の組成は、フェノール３５．
６ｗｔ％、メチルエチルケトン２５．８ｗｔ％、ｓｅｃ
−ブチルベンゼン１６７ｗｔ％、アセトフェノン１１．
２ｗｔ％、蟻酸３０８ｐｐｍ、酢酸４０４ｐｐｍ、及び
硫酸８００ｐｐｍであった。次に、中和槽、中和静置
槽、水洗槽及び水洗静置槽を直列に配してなる装置によ
り中和工程及び水洗工程を実施した。すなわち、容積
０．５ｌの中和槽に上記の分解液１２００ｇ／ｈ、４８
ｗｔ％水酸化ナトリウム水溶液４．９ｇ／ｈを連続的に
供給し、更に中和静置槽からのリサイクル水７３０ｇ／
ｈ及び水洗静置槽からのリサイクル水５７ｇ／ｈを供給
し、滞留時間１０分、温度６５℃、ｐＨ８の条件下にて
中和を行った。次に、中和された液を中和静置槽に送
り、水層と油層に分離した。なお、水層の一部（７３０
ｇ／ｈ）を中和槽へリサイクルし、残り２５ｇ／ｈは廃
棄した。なお、廃棄した水層中には、硫酸ナトリウム
４．８ｗｔ％、蟻酸ナトリウム２．０ｗｔ％及び酢酸ナ
トリウム２．８ｗｔ％が含まれていた。次に、中和静置
槽の油層１２３７ｇ／ｈを容積０．５ｌの水洗槽へ送
り、水洗用の水５７ｇ／ｈ及び水洗静置槽からのリサイ
クル水７６０ｇ／ｈを用いて、滞留時間１０分、温度６
５℃にて水洗を実施した。更に、水洗後の液を水洗静置
槽へ送り、水層と油層に分離した。得られた油層中に
は、蟻酸ナトリウム５ｗｔｐｐｍ、酢酸ナトリウム９ｗ
ｔｐｐｍが含有され、硫酸ナトリウムは不検出であっ
た。Next, the present invention will be described by way of examples. Example 1 In a 5.2 l decomposition reactor, 61.5 wt% of sec-butylbenzene hydroperoxide, 16.7 wt% of sec-butylbenzene, and 10.6 wt% of acetophenone were added.
12.8 kg / h and 98 wt.
% Sulfuric acid was supplied at 10 g / h, and a decomposition reaction was carried out at a temperature of 65 ° C. The composition of the obtained decomposition solution was phenol 35.
6 wt%, methyl ethyl ketone 25.8 wt%, sec
-Butylbenzene 167 wt%, acetophenone 11.
2 wt%, formic acid 308 ppm, acetic acid 404 ppm, and sulfuric acid 800 ppm. Next, a neutralization tank, a neutralization standing tank, a water washing tank, and a neutralization step and a water washing step were performed by a device including a series of water washing and standing tanks. That is, 1200 g / h, 48
4.9 g / h of an aqueous solution of wt% sodium hydroxide was continuously supplied, and 730 g of recycled water from a neutralization still tank was supplied.
h and 57 g / h of recycled water from the washing and standing tank were supplied, and neutralization was performed under the conditions of a residence time of 10 minutes, a temperature of 65 ° C., and a pH of 8. Next, the neutralized liquid was sent to a neutralization standing tank, and separated into an aqueous layer and an oil layer. A part of the water layer (730
g / h) was recycled to the neutralization tank, and the remaining 25 g / h was discarded. The discarded aqueous layer contained 4.8% by weight of sodium sulfate, 2.0% by weight of sodium formate, and 2.8% by weight of sodium acetate. Next, 1237 g / h of the oil layer in the neutralization standing tank was sent to a 0.5 l water washing tank, and 57 g / h of water for washing and 760 g / h of recycled water from the water washing standing tank were used for a retention time of 10 g. Min, temperature 6
Washing was performed at 5 ° C. Further, the liquid after water washing was sent to a water washing standing tank, and separated into an aqueous layer and an oil layer. In the obtained oil layer, sodium formate 5wtppm, sodium acetate 9w
tppm was contained and sodium sulfate was not detected.
【００１５】比較例１ 実施例１の水洗及び水洗後の静置を行わなかったこと以
外は、実施例１と同様に実施した。その結果、得られた
油層中に含まれる脂肪酸塩の含有量は、蟻酸ナトリウム
７１ｗｔｐｐｍ、酢酸ナトリウム１０９ｗｔｐｐｍ及び
硫酸ナトリウム２０ｗｔｐｐｍであった。すなわち、本
発明の水洗工程により、脂肪酸塩類及び無機塩類が極め
て効率的に除去されていることがわかる。Comparative Example 1 The procedure of Example 1 was repeated, except that the washing in Example 1 and the standing after the washing were not performed. As a result, the content of the fatty acid salt contained in the obtained oil layer was 71 wtppm of sodium formate, 109 wtppm of sodium acetate, and 20 wtppm of sodium sulfate. That is, it is understood that the fatty acid salts and the inorganic salts are extremely efficiently removed by the water washing step of the present invention.
【００１６】[0016]
【発明の効果】以上説明したとおり、本発明により、ｓ
ｅｃ−ブチルベンゼンを出発原料とするフェノール及び
メチルエチルケトンの製造方法であって、蒸留に付する
液中の脂肪酸塩類及び無機塩類を極めて低い水準に維持
でき、よって蒸留装置各所への脂肪酸塩類及び無機塩類
の析出を防止し、熱効率の点において優れ、かつ閉塞に
より蒸留操作を中断せざるを得ないといった問題を伴な
わず、長期間にわたって安定な連続運転が可能であると
いう優れたフェノール及びメチルエチルケトンの製造方
法を提供することができた。As described above, according to the present invention, s
A method for producing phenol and methyl ethyl ketone using ec-butylbenzene as a starting material, wherein fatty acid salts and inorganic salts in a liquid subjected to distillation can be maintained at an extremely low level, and thus fatty acid salts and inorganic salts can be sent to various parts of a distillation apparatus. Production of phenol and methyl ethyl ketone, which prevent precipitation of phenol and are excellent in terms of thermal efficiency, and are capable of stable continuous operation for a long period of time without the problem that the distillation operation must be interrupted due to clogging. A method could be provided.
フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ Ｃ０７Ｃ 49/10 Ｃ０７Ｃ 49/10 407/00 407/00 409/08 409/08 // Ｃ０７Ｂ 61/00 ３００ Ｃ０７Ｂ 61/00 ３００ (58)調査した分野(Int.Cl.7，ＤＢ名) C07C 27/00 C07C 37/08 C07C 39/02 - 39/11 C07C 45/53 C07C 49/04 - 49/185 Continuation of front page (51) Int.Cl. 7 Identification code FI C07C 49/10 C07C 49/10 407/00 407/00 409/08 409/08 // C07B 61/00 300 C07B 61/00 300 (58) Field surveyed (Int. Cl. 7 , DB name) C07C 27/00 C07C 37/08 C07C 39/02-39/11 C07C 45/53 C07C 49/04-49/185
Claims (1)
フェノール及びメチルエチルケトンを製造する方法であ
って、下記の工程を含むことを特徴とするフェノール及
びメチルエチルケトンの製造方法。 酸化工程：ｓｅｃ−ブチルベンゼンを酸化してｓｅｃ−
ブチルベンゼンハイドロパーオキサイドを主成分とする
酸化反応液を得る工程 濃縮工程：酸化反応液を蒸留により濃縮し、塔底部から
ｓｅｃ−ブチルベンゼンハイドロパーオキサイドを主成
分とする塔底液を得、塔頂部からｓｅｃ−ブチルベンゼ
ンを主成分とする留出液を得る工程 分解工程：濃縮工程の塔底液を酸性触媒と接触させるこ
とにより、ｓｅｃ−ブチルベンゼンハイドロパーオキサ
イドをフェノールとメチルエチルケトンに分解する工程 中和工程：分解工程で得られた分解液をアルカリ水溶液
により中和し、油層と水層に分離し、水層の一部を再度
中和工程の入口へリサイクルする工程 水洗工程：中和工程で得られた油層を水洗し、フェノー
ル及びメチルエチルケトンを主成分とする油層と水層に
分離し、水層の一部又は全部を中和工程へリサイクルす
る工程 精製工程：水洗工程で得られた油層を蒸留に付し、フェ
ノールとメチルエチルケトンを分離する工程1. A method for producing phenol and methyl ethyl ketone using sec-butylbenzene as a starting material, comprising the following steps: Oxidation step: sec-butylbenzene is oxidized to sec-
Step of obtaining an oxidation reaction solution containing butylbenzene hydroperoxide as a main component Concentration step: Concentrating the oxidation reaction solution by distillation to obtain a bottom solution containing sec-butylbenzene hydroperoxide as a main component from the bottom of the column. Step of obtaining a distillate containing sec-butylbenzene as the main component from the top Decomposition step: a step of decomposing sec-butylbenzene hydroperoxide into phenol and methyl ethyl ketone by bringing the bottom liquid of the concentration step into contact with an acidic catalyst. Neutralization step: The decomposition solution obtained in the decomposition step is neutralized with an aqueous alkali solution, separated into an oil layer and an aqueous layer, and a part of the aqueous layer is recycled to the inlet of the neutralization step. The oil layer obtained in the above is washed with water, separated into an oil layer mainly composed of phenol and methyl ethyl ketone and an aqueous layer, and a part or all of the aqueous layer is separated. Recycling process to neutralization process Purification process: The oil layer obtained in the water washing process is subjected to distillation to separate phenol and methyl ethyl ketone
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34497891A JP3089780B2 (en) | 1991-12-26 | 1991-12-26 | Method for producing phenol and methyl ethyl ketone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34497891A JP3089780B2 (en) | 1991-12-26 | 1991-12-26 | Method for producing phenol and methyl ethyl ketone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05178773A JPH05178773A (en) | 1993-07-20 |
| JP3089780B2 true JP3089780B2 (en) | 2000-09-18 |
Family
ID=18373449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP34497891A Expired - Fee Related JP3089780B2 (en) | 1991-12-26 | 1991-12-26 | Method for producing phenol and methyl ethyl ketone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3089780B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003183248A (en) * | 2001-12-19 | 2003-07-03 | Sumitomo Chem Co Ltd | Purification method of oxidation reaction solution |
| TW200744986A (en) * | 2006-02-14 | 2007-12-16 | Exxonmobil Chemical Patents Inc | Process for producing phenol and methyl ethyl ketone |
| JP5656343B2 (en) * | 2007-12-27 | 2015-01-21 | 三菱化学株式会社 | Process for producing purified pentamethylenediamine |
| JP7683268B2 (en) * | 2021-03-26 | 2025-05-27 | 三菱ケミカル株式会社 | Phenol production method |
-
1991
- 1991-12-26 JP JP34497891A patent/JP3089780B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05178773A (en) | 1993-07-20 |
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