JPH11152279A - Production of propylene oxide - Google Patents
Production of propylene oxideInfo
- Publication number
- JPH11152279A JPH11152279A JP9319505A JP31950597A JPH11152279A JP H11152279 A JPH11152279 A JP H11152279A JP 9319505 A JP9319505 A JP 9319505A JP 31950597 A JP31950597 A JP 31950597A JP H11152279 A JPH11152279 A JP H11152279A
- Authority
- JP
- Japan
- Prior art keywords
- liquid phase
- ethylbenzene
- alkali
- propylene oxide
- 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.)
- Granted
Links
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、プロピレンオキサ
イドの製造方法に関するものである。更に詳しくは、本
発明は、エチルベンゼンとプロピレンを原料とするプロ
ピレンオキサイドの製造方法であって、アルカリ洗浄時
に有機酸によるエチルベンゼンハイドロパーオキサイド
の分解劣化を抑制することができるプロピレンオキサイ
ドの製造方法に関するものである。なお、プロピレンオ
キサイドは、ポリウレタン製造の原料などとして用いら
れる有用な工業薬品のひとつである。[0001] The present invention relates to a method for producing propylene oxide. More specifically, the present invention relates to a method for producing propylene oxide using ethylbenzene and propylene as raw materials, and relates to a method for producing propylene oxide which can suppress decomposition and degradation of ethylbenzene hydroperoxide due to an organic acid during alkali washing. It is. Propylene oxide is one of useful industrial chemicals used as a raw material for producing polyurethane.
【０００２】[0002]
【従来の技術】オレフィン型化合物と、エチルベンゼン
ハイドロパーオキサイドをＴｉ含有固体触媒の存在下に
反応させ、オレフィン型化合物をオキシラン化合物に変
換する方法は公知である（特公昭５６−３５９４１号公
報、５４−４０５２５号公報、５４−４０５２６号公
報、５０−３００４９号公報など参照。）。しかしなが
ら、これらの方法で調整した触媒を用いてプロピレンの
エポキシ化反応を行うと、原料中の不純物である有機酸
類によって触媒の活性が時間とともに低下する。これを
防ぐために、該原料液中の有機酸類を除去する必要があ
る。しかしながら、例えばアルカリ洗浄時に分解劣化す
るという問題がある。2. Description of the Related Art A method of converting an olefin type compound into an oxirane compound by reacting an olefin type compound with ethylbenzene hydroperoxide in the presence of a Ti-containing solid catalyst is known (JP-B-56-35941, 54). -40525, 54-40526, 50-30049, etc.). However, when an epoxidation reaction of propylene is performed using a catalyst prepared by these methods, the activity of the catalyst decreases with time due to organic acids which are impurities in the raw material. In order to prevent this, it is necessary to remove organic acids in the raw material liquid. However, there is a problem in that it is decomposed and deteriorated, for example, during alkali washing.
【０００３】[0003]
【発明が解決しようとする課題】かかる現状に鑑み、本
発明が解決しようとする課題は、エチルベンゼンとプロ
ピレンを原料とするプロピレンオキサイドの製造方法で
あって、アルカリ洗浄時に有機酸によるエチルベンゼン
ハイドロパーオキサイドの分解劣化を抑制することがで
きるプロピレンオキサイドの製造方法を提供する点に存
する。SUMMARY OF THE INVENTION In view of the above situation, an object of the present invention is to provide a method for producing propylene oxide using ethylbenzene and propylene as raw materials. An object of the present invention is to provide a method for producing propylene oxide which can suppress decomposition and degradation of propylene oxide.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、エチルベ
ンゼンの液相酸化で得られるエチルベンゼンハイドロパ
ーオキサイドのエチルベンゼン溶液である原料液のアル
カリ洗浄精製について詳細に検討した。その結果、該原
料液中に存在する有機酸類が、エチルベンゼンハイドロ
パーオキサイドの分解劣化に大きく関与することを見い
だした。つまり、有機酸類を中和された条件でアルカリ
洗浄を行うことにより、分解劣化現象が抑制又は防止さ
れることを見いだした。更に原料液中の有機酸類を中和
された状態にする方法として、エチルベンゼの液相酸化
において、アルカリ金属化合物又はアルカリ土類金属化
合物を添加し、乳化酸化を行うことが極めて有効である
ことを見いだし、本発明を完成させた。Means for Solving the Problems The present inventors have studied in detail the alkali washing and purification of a raw material solution which is an ethylbenzene solution of ethylbenzene hydroperoxide obtained by liquid phase oxidation of ethylbenzene. As a result, it has been found that organic acids present in the raw material liquid greatly contribute to decomposition and degradation of ethylbenzene hydroperoxide. That is, it has been found that by performing the alkali washing under the condition where the organic acids are neutralized, the decomposition deterioration phenomenon is suppressed or prevented. Further, as a method for neutralizing the organic acids in the raw material liquid, it is extremely effective to add an alkali metal compound or an alkaline earth metal compound in the liquid phase oxidation of ethylbenzene to perform emulsion oxidation. Have found and completed the present invention.
【０００５】すなわち、本発明は、下記、液相酸化工
程、アルカリ洗浄工程及びエポキシ化工程を含むプロピ
レンオキサイドの製造方法に係るものである。 液相酸化工程：アルカリ金属化合物又はアルカリ土類金
属化合物の存在下、エチルベンゼンの液相乳化酸化を行
い、エチルベンゼンハイドロパーオキサイドを得る工程 アルカリ洗浄工程：液相酸化工程で得た反応液をアルカ
リ洗浄する工程 エポキシ化工程：チタン含有固体触媒の存在下、アルカ
リ洗浄後の反応液中のエチルベンゼンハイドロパーオキ
サイドとプロピレンとをエポキシ化反応に付し、プロピ
レンオキサイドを得る工程That is, the present invention relates to a method for producing propylene oxide, which comprises the following liquid phase oxidation step, alkali washing step and epoxidation step. Liquid phase oxidation step: A step of performing liquid phase emulsification oxidation of ethylbenzene in the presence of an alkali metal compound or an alkaline earth metal compound to obtain ethylbenzene hydroperoxide. Alkali washing step: Alkaline washing of the reaction solution obtained in the liquid phase oxidation step. Epoxidation step: a step of subjecting ethylbenzene hydroperoxide and propylene in the reaction solution after alkali washing to propylene to an epoxidation reaction in the presence of a titanium-containing solid catalyst to obtain propylene oxide.
【０００６】[0006]
【発明の実施の形態】本発明の液相酸化工程は、アルカ
リ金属化合物又はアルカリ土類金属化合物の存在下、エ
チルベンゼンの液相乳化酸化を行い、エチルベンゼンハ
イドロパーオキサイドを得る工程である。DESCRIPTION OF THE PREFERRED EMBODIMENTS The liquid phase oxidation step of the present invention is a step in which ethylbenzene is subjected to liquid phase emulsification oxidation in the presence of an alkali metal compound or an alkaline earth metal compound to obtain ethylbenzene hydroperoxide.
【０００７】エチルベンゼン（以下、「ＥＢ」と略
す。）の液相自動酸化は、通常５０〜１５０℃で分子状
酸素により行われる。エチルベンゼンハイドロパーオキ
サイド（以下、「ＥＢＨＰ」と略す。）への選択率を高
く維持するため、ＥＢの転化率は低く抑えられる。この
ため酸化反応液中のＥＢＨＰの濃度は通常５〜１５重量
％となる。通常はこの酸化反応液を濃縮工程に供し、蒸
留により一部のＥＢ等の軽沸分を留去させることによっ
て、ＥＢＨＰの濃度を高めたあとで、プロピレンとのエ
ポキシ化反応に供する。ところが、該酸化反応液中に相
当量の有機酸が存在しており、この一部は濃縮工程で除
かれず、次のエポキシ化反応でのＴｉ含有固体触媒の触
媒毒となるため、アルカリ洗浄に供することで有機酸類
を除去することが好ましい。しかしながら、脂肪族カル
ボン酸類、その中でも特に水溶性の低級脂肪族カルボン
酸はＥＢＨＰの分解劣化への影響が大きいことが判明し
た。従って、アルカリ洗浄の原料液中の有機酸類を中和
させるために、ＥＢの液相自動酸化において少量のアル
カリ化合物又はその水溶液を存在させる液相乳化酸化を
採用することが有効である。The liquid phase autoxidation of ethylbenzene (hereinafter abbreviated as “EB”) is usually carried out at 50 to 150 ° C. with molecular oxygen. In order to maintain a high selectivity to ethylbenzene hydroperoxide (hereinafter abbreviated as “EBHP”), the conversion of EB is kept low. Therefore, the concentration of EBHP in the oxidation reaction solution is usually 5 to 15% by weight. Usually, this oxidation reaction liquid is subjected to a concentration step, and a part of light boiling components such as EB is distilled off by distillation to increase the concentration of EBHP, and then subjected to an epoxidation reaction with propylene. However, a considerable amount of organic acid is present in the oxidation reaction solution, and a part of the organic acid is not removed in the concentration step and becomes a catalyst poison of the Ti-containing solid catalyst in the next epoxidation reaction. To remove organic acids. However, it has been found that aliphatic carboxylic acids, especially water-soluble lower aliphatic carboxylic acids, have a great influence on the degradation and degradation of EBHP. Therefore, in order to neutralize the organic acids in the raw material liquid for the alkali washing, it is effective to employ liquid phase emulsification oxidation in which a small amount of an alkali compound or an aqueous solution thereof is present in the liquid phase autoxidation of EB.
【０００８】ＥＢの液相乳化酸化は、通常５０〜１５０
℃で、アルカリ金属化合物又はアルカリ土類金属化合物
を添加し、分子状酸素により行われる。アルカリ金属化
合物又はアルカリ土類金属化合物としては、ＮａＯＨ、
ＫＯＨ、Ｎａ2 ＣＯ3 、Ｋ2ＣＯ3 などのアルカリ金属
水酸化物やアルカリ金属炭酸塩が好ましく用いられる。
ＮａＯＨとＮａ2 ＣＯ3 が工業的に安価で入手容易のた
め特に好まれる。ＥＢＨＰへの選択率を高く維持するた
め、ＥＢの転化率は低く抑えられる。このため酸化反応
液中のＥＢＨＰ濃度は通常５〜１５重量％となる。添加
するアルカリ金属化合物又はアルカリ土類金属化合物の
量はＥＢに対し０．００１〜１０モル％であり、好まし
くは０．００５〜５モル％である。添加量が大きすぎる
とアルカリ化合物が大量に必要なり、経済性でコスト高
になり不利であり、一方小さすぎると生成した有機酸類
が中和されない場合がある。アルカリ化合物の添加方法
は、そのままもしくは水溶液として行う。水溶液で添加
する場合は原料油とアルカリ水溶液の容量比（Ｏ／Ｗ）
は０．１〜１００であり、好ましくは０．２〜５０であ
る。Ｏ／Ｗは大きすぎると油・水の混合性が悪くなり、
十分に反応が進行しない場合があり、小さすぎると多量
の排水により不経済となる。[0008] The liquid phase emulsion oxidation of EB is usually 50 to 150
At 0 ° C., an alkali metal compound or an alkaline earth metal compound is added and the reaction is carried out with molecular oxygen. As the alkali metal compound or the alkaline earth metal compound, NaOH,
Alkali metal hydroxides and alkali metal carbonates such as KOH, Na 2 CO 3 and K 2 CO 3 are preferably used.
NaOH and Na 2 CO 3 are particularly preferred because they are industrially inexpensive and readily available. To keep the selectivity to EBHP high, the conversion of EB is kept low. For this reason, the EBHP concentration in the oxidation reaction solution is usually 5 to 15% by weight. The amount of the alkali metal compound or alkaline earth metal compound to be added is 0.001 to 10 mol%, preferably 0.005 to 5 mol%, based on EB. If the addition amount is too large, a large amount of the alkali compound is required, which is disadvantageous because the cost and cost are high, while if it is too small, the generated organic acids may not be neutralized. The alkali compound is added as it is or as an aqueous solution. When adding as an aqueous solution, the volume ratio between the feed oil and the aqueous alkali solution (O / W)
Is from 0.1 to 100, preferably from 0.2 to 50. If O / W is too large, the mixing property of oil and water will be poor,
In some cases, the reaction does not proceed sufficiently, and if it is too small, a large amount of drainage becomes uneconomical.
【０００９】本発明のアルカリ洗浄工程は、液相酸化工
程で得た反応液をアルカリ洗浄する工程である。The alkali washing step of the present invention is a step of washing the reaction solution obtained in the liquid phase oxidation step with alkali.
【００１０】前記のごとく得られたＥＢＨＰ溶液は、脂
肪族カルボン酸類の大部分は除かれるものの、例えば安
息香酸等の芳香族カルボン酸類を含んでいるため、さら
にアルカリ洗浄に供される。原料液中のＥＢＨＰ濃度は
１０〜２５重量％が好ましく、更に好ましくは１２〜２
０重量％である。これより低いＥＢＨＰ濃度では、洗浄
装置も過大となり経済的でない。また、これより高い濃
度では、アルカリ洗浄時の分液性が悪化し、有機酸類の
除去率が低下する。[0010] The EBHP solution obtained as described above contains most of the aliphatic carboxylic acids, but contains an aromatic carboxylic acid such as benzoic acid. The EBHP concentration in the raw material liquid is preferably from 10 to 25% by weight, more preferably from 12 to 2% by weight.
0% by weight. If the EBHP concentration is lower than this, the cleaning device becomes too large and is not economical. On the other hand, if the concentration is higher than this, the liquid separating property at the time of washing with alkali deteriorates, and the removal rate of organic acids decreases.
【００１１】前記のごとき濃度範囲のＥＢＨＰ溶液は酸
化反応液の適度の蒸留による濃縮操作により容易に得ら
れる。アルカリ源としては、ＮａＯＨ、ＫＯＨ、Ｎａ2
ＣＯ 3 、Ｋ2 ＣＯ3 、ＮａＨＣＯ3 、ＫＨＣＯ3 などの
アルカリ金属水酸化物やアルカリ金属炭酸塩が好ましく
用いられる。ＮａＯＨとＮａ2 ＣＯ3 が工業的に安価で
入手容易のため、特に好ましい。アルカリ水溶液の濃度
は通常０．０１〜３０重量％であり、好ましくは０．０
５〜１０重量％である。The EBHP solution having the above concentration range is an acid solution.
Of the reaction solution by moderate distillation.
It is. NaOH, KOH, NaTwo
CO Three, KTwoCOThree, NaHCOThree, KHCOThreeSuch as
Alkali metal hydroxides and alkali metal carbonates are preferred
Used. NaOH and NaTwoCOThreeBut industrially cheap
It is particularly preferable because it is easily available. Alkaline aqueous solution concentration
Is usually 0.01 to 30% by weight, preferably 0.0
5 to 10% by weight.
【００１２】原料油とフレッシュのアルカリ水溶液のＯ
／Ｗは、通常１０００／１〜１／１であり、好ましくは
１００／１〜１／１である。Ｏ／Ｗが大きすぎると有機
酸類の除去が不十分となり、また小さすぎると排水量が
増えるために不経済となる。[0012] O of raw material oil and fresh alkaline aqueous solution
/ W is generally 1000/1 to 1/1, preferably 100/1 to 1/1. If the O / W is too large, the removal of organic acids becomes insufficient, and if the O / W is too small, the wastewater volume increases, which is uneconomical.
【００１３】アルカリ洗浄は前述のＥＢＨＰ原料油とア
ルカリ水溶液を適度に混合したのち静置して分液させ、
ＥＢＨＰを含む油層を回収すればよい。洗浄や静置の温
度は通常０〜１００℃であり、好ましくは３０〜８０℃
である。高温すぎると、ＥＢＨＰの熱分解等の好ましく
ない副反応が併発し、また低温すぎるのは、冷却に要す
るエネルギーが過大となる。油水の混合時間と静置時間
は限定的でなく、必要十分な混合および分液に要する静
置が行えればよいが、通常は１〜１００分程度である。
洗浄方法は、回分法、連続法のいずれでも可能である。In the alkali washing, the above-mentioned EBHP base oil and an aqueous alkali solution are mixed appropriately, and then allowed to stand still to be separated.
What is necessary is just to collect | recover the oil layer containing EBHP. The temperature for washing and standing is usually 0 to 100 ° C, preferably 30 to 80 ° C.
It is. If the temperature is too high, undesired side reactions such as thermal decomposition of EBHP occur simultaneously, and if the temperature is too low, the energy required for cooling becomes excessive. The mixing time and the standing time of the oil and water are not limited, and it is sufficient that the necessary and sufficient mixing and separation for the liquid separation can be performed, but it is usually about 1 to 100 minutes.
The washing method can be any of a batch method and a continuous method.
【００１４】アルカリ洗浄で得た油層を更に水洗浄に供
してもよい。この場合、水洗浄時の条件（Ｏ／Ｗ、温
度、時間）は前述したアルカリ洗浄と同じでよい。The oil layer obtained by the alkali washing may be further subjected to water washing. In this case, the conditions (O / W, temperature, time) at the time of water washing may be the same as those of the above-described alkali washing.
【００１５】本発明のエポキシ化工程は、チタン含有固
体触媒の存在下、アルカリ洗浄後の反応液中のエチルベ
ンゼンハイドロパーオキサイドとプロピレンとをエポキ
シ化反応に付し、プロピレンオキサイドを得る工程であ
る。[0015] The epoxidation step of the present invention is a step of subjecting ethylbenzene hydroperoxide and propylene in the reaction solution after washing with alkali to epoxidation reaction in the presence of a titanium-containing solid catalyst to obtain propylene oxide.
【００１６】触媒はＴｉ含有固体触媒、例えばＴｉ化合
物を各種担体に担持したもの、共沈法やゾルゲル法で他
の酸化物を複合したもの、あるいはＴｉを含むゼオライ
ト系酸化物などで、好ましくは固体シリカ及び／又は無
機珪酸塩と化学的に結合したＴｉを含有する、いわゆる
Ｔｉ−シリカ触媒存在下、プロピレンと反応させる。エ
ポキシ化反応に供するプロピレンとＥＢＨＰのモル比は
通常１：１〜５０：１であり、好ましくは１：１〜２
０：１である。未反応プロピレンは回収してエポキシ化
反応に再使用すればよい。反応温度は通常０〜２００℃
であり、好ましくは３０〜１５０℃であり、また反応圧
力は通常１〜１００ａｔｍであり、好ましくは１０〜５
０ａｔｍである。The catalyst is a Ti-containing solid catalyst, for example, a catalyst in which a Ti compound is supported on various carriers, a compound in which another oxide is compounded by a coprecipitation method or a sol-gel method, or a zeolite-based oxide containing Ti. It is reacted with propylene in the presence of a so-called Ti-silica catalyst containing Ti chemically bonded to solid silica and / or inorganic silicate. The molar ratio of propylene to EBHP to be subjected to the epoxidation reaction is usually 1: 1 to 50: 1, preferably 1: 1 to 2
0: 1. Unreacted propylene may be recovered and reused in the epoxidation reaction. Reaction temperature is usually 0 to 200 ° C
, Preferably 30 to 150 ° C, and the reaction pressure is usually 1 to 100 atm, preferably 10 to 5 atm.
0 atm.
【００１７】[0017]
【実施例】以下、実施例により本発明を説明する。以下
の記号を使用する。 ＥＢ：エチルベンゼン ＥＢＨＰ：エチルベンゼンハイドロパーオキサイド ＬＡＣ：乳酸 ＦＯＡ：ぎ酸 ＡＣＤ：酢酸 ＰＲＡＣ：プロピオン酸 ＢＥＣ：安息香酸 ＡＣＰ：アセトフェノン ＭＢＡ：α−メチルベンジルアルコールThe present invention will be described below with reference to examples. Use the following symbols: EB: ethylbenzene EBHP: ethylbenzene hydroperoxide LAC: lactic acid FOA: formic acid ACD: acetic acid PRAC: propionic acid BEC: benzoic acid ACP: acetophenone MBA: α-methylbenzyl alcohol
【００１８】実施例１ＥＢの液相酸化 ＥＢ（７０ｇ）と０．０００４重量％ＮａＯＨ水溶液
（１．５Ｌ）を３Ｌ丸底フラスコに入れ酸素を通じて、
１５０℃で４時間反応を行う。フラスコを氷浴中で冷却
した後、反応混合物を分析する。結果として、ＥＢ反応
率５％、ＥＢＨＰ選択率（ＥＢ基準）８５％が得られ
る。ＥＢＨＰ溶液のアルカリ洗浄 上記の乳化酸化によって得られるＥＢＨＰ溶液（１００
ｇ）とＮａＯＨ水溶液（１９ｇ）を６０℃、１５分間攪
拌混合し、同温で１５分間静置した後、ＥＢＨＰを含む
油層を得る。本洗浄中のＥＢＨＰの分解は原料中のＥＢ
ＨＰに対し０．０５％である。なお、分解物としては、
ＭＢＡは検出されずにＡＣＰのみである。Example 1 Liquid Phase Oxidation of EB EB (70 g) and a 0.0004 wt% NaOH aqueous solution (1.5 L) were placed in a 3 L round bottom flask, and oxygen was passed through.
The reaction is performed at 150 ° C. for 4 hours. After cooling the flask in an ice bath, the reaction mixture is analyzed. As a result, an EB reaction rate of 5% and an EBHP selectivity (based on EB) of 85% are obtained. Alkaline washing of EBHP solution The EBHP solution (100
g) and an aqueous NaOH solution (19 g) were stirred and mixed at 60 ° C. for 15 minutes and allowed to stand at the same temperature for 15 minutes to obtain an oil layer containing EBHP. Decomposition of EBHP during main cleaning is based on EB
0.05% based on HP. In addition, as a decomposition product,
MBA is not detected but only ACP.
【００１９】比較例１ＥＢの液相酸化 ＥＢ（７０ｇ）を３Ｌ丸底フラスコに入れ酸素を通じ
て、１５０℃で４時間反応を行う。反応は乳化酸化では
なく、液相自動酸化とする。フラスコを氷浴中で冷却し
た後、反応混合物を分析する。結果として、ＥＢ反応率
５％、ＥＢＨＰ選択率（ＥＢ基準）８５％が得られる。ＥＢＨＰ溶液のアルカリ洗浄 上記の自動酸化によって得られるＥＢＨＰ溶液を、実施
例と同様のアルカリ洗浄を行う。ＥＢＨＰの分解は０．
４８％と大きく、分解物としてはＭＢＡが検出される。Comparative Example 1 Liquid Phase Oxidation of EB EB (70 g) was placed in a 3 L round-bottomed flask, and allowed to react at 150 ° C. for 4 hours through oxygen. The reaction is not emulsion oxidation but liquid phase autoxidation. After cooling the flask in an ice bath, the reaction mixture is analyzed. As a result, an EB reaction rate of 5% and an EBHP selectivity (based on EB) of 85% are obtained. Alkaline cleaning of EBHP solution The EBHP solution obtained by the above-mentioned autoxidation is subjected to the same alkali cleaning as in the examples. The degradation of EBHP is 0.
As large as 48%, MBA is detected as a decomposition product.
【００２０】[0020]
【発明の効果】以上説明したとおり、本発明により、エ
チルベンゼンとプロピレンを原料とするプロピレンオキ
サイドの製造方法であって、アルカリ洗浄時に有機酸に
よるエチルベンゼンハイドロパーオキサイドの分解劣化
を抑制することができるプロピレンオキサイドの製造方
法を提供することができる。As described above, according to the present invention, there is provided a method for producing propylene oxide using ethylbenzene and propylene as raw materials, wherein the degradation of ethylbenzene hydroperoxide by an organic acid during alkali washing can be suppressed. An oxide production method can be provided.
Claims (1)
及びエポキシ化工程を含むプロピレンオキサイドの製造
方法。 液相酸化工程：アルカリ金属化合物又はアルカリ土類金
属化合物の存在下、エチルベンゼンの液相乳化酸化を行
い、エチルベンゼンハイドロパーオキサイドを得る工程 アルカリ洗浄工程：液相酸化工程で得た反応液をアルカ
リ洗浄する工程 エポキシ化工程：チタン含有固体触媒の存在下、アルカ
リ洗浄後の反応液中のエチルベンゼンハイドロパーオキ
サイドとプロピレンとをエポキシ化反応に付し、プロピ
レンオキサイドを得る工程1. A method for producing propylene oxide, comprising the following liquid phase oxidation step, alkali washing step and epoxidation step. Liquid phase oxidation step: A step of performing liquid phase emulsification oxidation of ethylbenzene in the presence of an alkali metal compound or an alkaline earth metal compound to obtain ethylbenzene hydroperoxide. Alkali washing step: Alkaline washing of the reaction solution obtained in the liquid phase oxidation step. Epoxidation step: a step of subjecting ethylbenzene hydroperoxide and propylene in the reaction solution after alkali washing to propylene to an epoxidation reaction in the presence of a titanium-containing solid catalyst to obtain propylene oxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31950597A JP3965745B2 (en) | 1997-11-20 | 1997-11-20 | Propylene oxide production method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31950597A JP3965745B2 (en) | 1997-11-20 | 1997-11-20 | Propylene oxide production method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH11152279A true JPH11152279A (en) | 1999-06-08 |
| JP3965745B2 JP3965745B2 (en) | 2007-08-29 |
Family
ID=18110981
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31950597A Expired - Fee Related JP3965745B2 (en) | 1997-11-20 | 1997-11-20 | Propylene oxide production method |
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| Country | Link |
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| JP (1) | JP3965745B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003081886A (en) * | 2001-09-13 | 2003-03-19 | Sumitomo Chem Co Ltd | Method for producing cumene |
| JP2003081888A (en) * | 2001-09-13 | 2003-03-19 | Sumitomo Chem Co Ltd | Method for producing cumene |
-
1997
- 1997-11-20 JP JP31950597A patent/JP3965745B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003081886A (en) * | 2001-09-13 | 2003-03-19 | Sumitomo Chem Co Ltd | Method for producing cumene |
| JP2003081888A (en) * | 2001-09-13 | 2003-03-19 | Sumitomo Chem Co Ltd | Method for producing cumene |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3965745B2 (en) | 2007-08-29 |
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