JP2001206874A - Method for extracting and purifying hydroperoxide compounds - Google Patents
Method for extracting and purifying hydroperoxide compoundsInfo
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- JP2001206874A JP2001206874A JP2000016281A JP2000016281A JP2001206874A JP 2001206874 A JP2001206874 A JP 2001206874A JP 2000016281 A JP2000016281 A JP 2000016281A JP 2000016281 A JP2000016281 A JP 2000016281A JP 2001206874 A JP2001206874 A JP 2001206874A
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- solution
- purifying
- aqueous
- aqueous solution
- extracting
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Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、ヒドロペルオキシ
ド類の精製方法に関するものである。更に詳しくは、本
発明は、アルキル芳香族炭化水素の酸化で得られるヒド
ロペルオキシド類が含まれる液から、少なくとも一種の
ヒドロペルオキシド類をアルカリ水溶液を用いて抽出精
製する方法であって、精製工程中におけるヒドロペルオ
キシドの分解による損失を抑制し、よって経済的に有利
な条件下に実施し得るヒドロペルオキシドの精製方法に
関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for purifying hydroperoxides. More specifically, the present invention relates to a method for extracting and purifying at least one hydroperoxide from a liquid containing hydroperoxides obtained by oxidation of an alkyl aromatic hydrocarbon using an aqueous alkaline solution, wherein the method comprises the steps of: The present invention relates to a method for purifying hydroperoxide, which can suppress loss due to decomposition of hydroperoxide in the above, and can be carried out under economically advantageous conditions.
【０００２】[0002]
【従来の技術】アルキル芳香族炭化水素の酸化で得られ
るヒドロペルオキシド類は、酸分解反応を経てヒドロキ
シベンゼン類を得るための原料として用いられる。アル
キル芳香族炭化水素の酸化で得られる酸化反応液には、
所望のヒドロペルオキシド類の他、種々のヒドロペルオ
キシド類、ヒドロペルオキシド類から派生するアルコー
ル類、酸化原料であるアルキル芳香族炭化水素等が含ま
れている。かかる酸化反応液は精製工程に付され、所望
のヒドロペルオキシド類が分離・取得される。精製工程
としては、水洗、アルカリ水溶液を用いる抽出、有機溶
媒による洗浄、有機溶媒による抽出等がある。ところ
が、従来の方法によると、アルカリ水溶液を用いる抽出
時において、ヒドロペルオキシド類の一部が分解（ここ
での「分解」は、プロセス中に設けられる酸分解工程で
の分解を除き、ヒドロペルオキシドの劣化を意味す
る。）され、損失を生じるという問題があった。2. Description of the Related Art Hydroperoxides obtained by oxidation of alkyl aromatic hydrocarbons are used as raw materials for obtaining hydroxybenzenes through an acid decomposition reaction. The oxidation reaction solution obtained by oxidation of the alkyl aromatic hydrocarbon includes:
In addition to the desired hydroperoxides, various hydroperoxides, alcohols derived from the hydroperoxides, alkyl aromatic hydrocarbons as an oxidation raw material, and the like are included. Such an oxidation reaction solution is subjected to a purification step, and desired hydroperoxides are separated and obtained. The purification step includes washing with water, extraction with an aqueous alkali solution, washing with an organic solvent, extraction with an organic solvent, and the like. However, according to the conventional method, during the extraction using an aqueous alkali solution, a part of the hydroperoxide is decomposed ("decomposition" herein means the decomposition of the hydroperoxide except for the decomposition in the acid decomposition step provided in the process). This means that there is a problem of deterioration.)
【０００３】[0003]
【発明が解決しようとする課題】かかる状況の下、本発
明が解決しようとする課題は、アルキル芳香族炭化水素
の酸化で得られるヒドロペルオキシド類が含まれる液か
ら、少なくとも一種のヒドロペルオキシド類をアルカリ
水溶液を用いて抽出精製する方法であって、精製工程中
におけるヒドロペルオキシドの分解による損失を抑制
し、よって経済的に有利な条件下に実施し得るヒドロペ
ルオキシドの精製方法を提供する点に存するものであ
る。Under such circumstances, an object to be solved by the present invention is to convert at least one hydroperoxide from a liquid containing hydroperoxides obtained by oxidation of an alkyl aromatic hydrocarbon. Abstract: A method for extracting and purifying an aqueous solution using an alkaline aqueous solution, which is intended to provide a method for purifying a hydroperoxide which can suppress loss due to decomposition of hydroperoxide in a purification step and can be carried out under economically advantageous conditions. Things.
【０００４】[0004]
【課題を解決するための手段】すなわち、本発明は、ア
ルキル芳香族炭化水素の酸化で得られるヒドロペルオキ
シド類が含まれる液から、少なくとも一種のヒドロペル
オキシド類をアルカリ水溶液を用いて抽出精製する方法
であって、下記で定義されるA値が１０以下であるアル
カリ水溶液を用いるヒドロペルオキシド類の抽出精製方
法に係るものである。 Ａ：アルカリ水溶液１０ｍｌを１規定の塩酸水溶液で滴
定して得られるｐＨ滴定曲線の第一変曲点から第二変曲
点までの間に消費された塩酸水溶液の容量（ｍｌ）であ
る。ただし、変曲点が明確でない場合又は変曲点を３個
以上有する場合は、ｐＨ７からｐＨ２までの間に消費さ
れた塩酸水溶液の容量（ｍｌ）である。That is, the present invention provides a method for extracting and purifying at least one hydroperoxide from a solution containing hydroperoxides obtained by oxidation of an alkyl aromatic hydrocarbon using an aqueous alkali solution. The present invention relates to a method for extracting and purifying hydroperoxides using an alkaline aqueous solution having an A value of 10 or less as defined below. A: The volume (ml) of the aqueous hydrochloric acid solution consumed between the first inflection point and the second inflection point of the pH titration curve obtained by titrating 10 ml of the aqueous alkaline solution with a 1N aqueous hydrochloric acid solution. However, when the inflection point is not clear or has three or more inflection points, it is the volume (ml) of the hydrochloric acid aqueous solution consumed between pH 7 and pH 2.
【０００５】[0005]
【発明の実施の形態】アルキル芳香族炭化水素として
は、通常２級又は３級のアルキル基を有する芳香族炭化
水素が用いられ、アルキル基の具体例としてはエチル
基、イソプロピル基等をあげることができる。アルキル
基は、芳香環に通常１〜３個存在している。アルキル芳
香族炭化水素の具体例としては、エチルベンゼン、１，
３−ジイソプロピルベンゼン、１，４−ジイソプロピル
ベンゼン、１−メチル−３−イソプロピルベンゼン等を
あげることができる。BEST MODE FOR CARRYING OUT THE INVENTION As the alkyl aromatic hydrocarbon, an aromatic hydrocarbon having a secondary or tertiary alkyl group is usually used. Specific examples of the alkyl group include an ethyl group and an isopropyl group. Can be. Usually, 1 to 3 alkyl groups are present on the aromatic ring. Specific examples of the alkyl aromatic hydrocarbon include ethylbenzene,
Examples thereof include 3-diisopropylbenzene, 1,4-diisopropylbenzene, 1-methyl-3-isopropylbenzene, and the like.
【０００６】本発明においては、アルキル芳香族炭化水
素の酸化で得られるヒドロペルオキシド類が含まれる液
から、少なくとも一種のヒドロペルオキシド類をアルカ
リ水溶液を用いて抽出精製するにあたって、前記で定義
されるＡ値が１０以下、好ましくは５以下であるアルカ
リ水溶液を用いることを最大の特徴とする。このことに
より、抽出精製中におけるヒドロペルオキシドの分解に
よる損失を効率的に抑制できる。In the present invention, when extracting and purifying at least one kind of hydroperoxide from an aqueous solution containing hydroperoxides obtained by oxidation of an alkyl aromatic hydrocarbon by using an aqueous alkali solution, A is defined as above. The greatest feature is that an alkaline aqueous solution having a value of 10 or less, preferably 5 or less is used. Thereby, the loss due to the decomposition of the hydroperoxide during the extraction and purification can be efficiently suppressed.
【０００７】Ａ値とは、アルカリ水溶液１０ｍｌを１規
定の塩酸水溶液で滴定して得られるｐＨ滴定曲線の第一
変曲点から第二変曲点までの間に消費された塩酸水溶液
の容量（ｍｌ）である。ただし、変曲点が明確でない場
合又は変曲点を３個以上有する場合は、ｐＨ７からｐＨ
２までの間に消費された塩酸水溶液の容量（ｍｌ）であ
る。ここで、ｐＨ滴定曲線の高ｐＨ側から順次、第一変
曲点及び第二変曲点とする。The A value is defined as the volume of the aqueous hydrochloric acid solution consumed between the first inflection point and the second inflection point of the pH titration curve obtained by titrating 10 ml of an aqueous alkaline solution with a 1N aqueous hydrochloric acid solution ( ml). However, when the inflection point is not clear or when there are three or more inflection points, pH 7 to pH 7
The volume (ml) of the aqueous hydrochloric acid solution consumed up to 2. Here, the first inflection point and the second inflection point are sequentially set from the high pH side of the pH titration curve.
【０００８】以下、本発明を適用する具体的な例を、
１，３−ジイソプロピルベンゼンからレゾルシノールを
得るプロセスを用いて説明するが、本発明は該プロセス
に限定されるものではない。また、説明するプロセスは
代表的な例であり、適宜変更が可能である。また、下記
にあげたプロセス中の工程は、代表的なものであり、必
要に応じ、工程が追加される。Hereinafter, specific examples to which the present invention is applied will be described.
The present invention is described using a process for obtaining resorcinol from 1,3-diisopropylbenzene, but the present invention is not limited to this process. Further, the process to be described is a typical example, and can be appropriately changed. The steps in the process described below are typical, and steps may be added as necessary.
【０００９】なお、「ＭＤＣ」は１，３−ジイソプロピ
ルベンゼンを表し、「ＭＨＰＯ」は３−イソプロピル−
１−（２−ヒドロペルオキシ−２−プロピル）−ベンゼ
ンを表し、「ＤＨＰＯ」は１，３−ジ−（２−ヒドロペ
ルオキシ−２−プロピル）−ベンゼンを表し、「ＣＨＰ
Ｏ」は３−（２−ヒドロキシ−２−プロピル）−１−
（２−ヒドロペルオキシ−２−プロピル）−ベンゼンを
表し、「ＭＩＢＫ」はメチルイソブチルケトンを表し、
「ＯＳＴ」は３−（２−プロペニル）フェノールを表
し、「ＲＥＳ」はレゾルシノールを表し、「ＡＣＴ」は
アセトンを表す。Note that "MDC" represents 1,3-diisopropylbenzene, and "MHPO" is 3-isopropyl-
Represents 1- (2-hydroperoxy-2-propyl) -benzene, "DHPO" represents 1,3-di- (2-hydroperoxy-2-propyl) -benzene, and represents "CHP
“O” is 3- (2-hydroxy-2-propyl) -1-
Represents (2-hydroperoxy-2-propyl) -benzene, "MIBK" represents methyl isobutyl ketone,
"OST" represents 3- (2-propenyl) phenol, "RES" represents resorcinol, and "ACT" represents acetone.
【００１０】プロセスは、酸化工程、アルカリ抽出工
程、有機溶媒抽出工程、酸分解工程、蒸留工程および精
製工程を含む。The process includes an oxidation step, an alkali extraction step, an organic solvent extraction step, an acid decomposition step, a distillation step and a purification step.
【００１１】酸化工程は、ＭＤＣを含有する酸化原料液
を酸素又は空気で酸化する工程である。酸化原料液中に
は、主原料であるＭＨＰＯ２０〜６０重量％及びＭＤＣ
１０〜４０重量％の他、ＤＨＰＯ０〜５重量％及びＣＨ
ＰＯ０〜１０重量％が通常含有される。通常の反応条件
としては、温度７０〜１１０℃、圧力０〜１ＭＰａ
（Ｇ）、滞留時間０〜５０時間等をあげることができ
る。酸化工程に用いることができる装置としては、たと
えば流通式反応槽や反応塔をあげることができる。酸化
工程で得られる酸化反応液の通常の組成としては、ＤＨ
ＰＯ３〜３０重量％、ＣＨＰＯ０〜１０重量％、ＭＨＰ
Ｏ２０〜６０重量％及びＭＤＣ０〜３５重量％をあげる
ことができる。The oxidation step is a step of oxidizing an oxidizing raw material liquid containing MDC with oxygen or air. The oxidizing raw material liquid contains 20 to 60% by weight of the main raw material MHPO and MDC.
10-40% by weight, 0-5% by weight of DHPO and CH
PO0 to 10% by weight is usually contained. Normal reaction conditions include a temperature of 70 to 110 ° C. and a pressure of 0 to 1 MPa.
(G), a residence time of 0 to 50 hours, and the like. Examples of the apparatus that can be used in the oxidation step include a flow-type reaction tank and a reaction tower. The usual composition of the oxidation reaction solution obtained in the oxidation step is DH
PO3-30% by weight, CHPO0-10% by weight, MHP
O20 to 60% by weight and MDC0 to 35% by weight can be mentioned.
【００１２】アルカリ抽出工程において、酸化反応液は
アルカリ水溶液で抽出され、主としてＤＨＰＯ及びＣＨ
ＰＯを含むアルカリ水溶液が得られる。アルカリ水溶液
と酸化反応液の重量比は、通常０．２〜５である。アル
カリ水としては、コストの観点から、水酸化ナトリウム
水溶液が望ましい。アルカリ水溶液中のアルカリ濃度
は、通常０．１〜３０重量％である。通常の抽出条件と
しては、温度０〜７０℃、１〜１０段の向流抽出をあげ
ることができる。アルカリ抽出工程に用いる装置として
は、たとえばミキサーセトラーや抽出塔等をあげること
ができる。In the alkali extraction step, the oxidation reaction solution is extracted with an aqueous alkali solution, and is mainly composed of DHPO and CH.
An alkaline aqueous solution containing PO is obtained. The weight ratio between the aqueous alkali solution and the oxidation reaction solution is usually 0.2 to 5. As the alkaline water, an aqueous sodium hydroxide solution is desirable from the viewpoint of cost. The alkali concentration in the alkali aqueous solution is usually 0.1 to 30% by weight. Usual extraction conditions include a countercurrent extraction at a temperature of 0 to 70 ° C. and 1 to 10 stages. Examples of the apparatus used in the alkali extraction step include a mixer settler and an extraction tower.
【００１３】有機溶媒抽出工程において、ＤＨＰＯ及び
ＣＨＰＯを含むアルカリ水溶液は、有機溶媒中にＤＨＰ
ＯとＣＨＰＯのそれぞれに分離精製される。アルカリ水
溶液と有機溶媒の重量比は、通常０．２〜１０である。
有機溶媒としては、ＭＩＢＫが望ましい。通常の抽出条
件としては、温度２０〜８０℃をあげることができる。
有機溶媒抽出工程に用いる装置としては、たとえばミキ
サーセトラーや抽出塔等をあげることができる。抽出に
用いられたアルカリ水溶液は、次回のアルカリ抽出及び
有機溶媒抽出にリサイクル使用されるのが一般である。In the organic solvent extraction step, an alkaline aqueous solution containing DHPO and CHPO is mixed with DHP in an organic solvent.
O and CHPO are separated and purified. The weight ratio between the aqueous alkali solution and the organic solvent is usually from 0.2 to 10.
MIBK is desirable as the organic solvent. Normal extraction conditions include a temperature of 20 to 80 ° C.
Examples of the apparatus used in the organic solvent extraction step include a mixer settler and an extraction tower. The aqueous alkali solution used for the extraction is generally recycled for the next alkali extraction and organic solvent extraction.
【００１４】本発明の特徴は、前記のとおり、アルカリ
抽出工程および有機溶媒抽出工程で用いるアルカリ水溶
液のA値を１０以下とする点にある。用いるアルカリ水
溶液のＡ値が過多であると、抽出精製においてヒドロペ
ルオキシドの一部が分解され、損失を生じる。A feature of the present invention is that, as described above, the A value of the aqueous alkali solution used in the alkali extraction step and the organic solvent extraction step is 10 or less. If the A value of the aqueous alkaline solution used is excessive, a part of the hydroperoxide is decomposed in the extraction and purification, resulting in loss.
【００１５】酸分解工程では、酸分解により、ＤＨＰＯ
を含む有機溶媒液からＲＥＳとＡＣＴを含む有機溶媒液
が得られる。In the acid decomposition step, DHPO is formed by acid decomposition.
The organic solvent liquid containing RES and ACT is obtained from the organic solvent liquid containing.
【００１６】蒸留工程では、酸分解工程で得られた有機
溶媒液を中和し、該中和された有機溶媒液を蒸留又は蒸
留及びアルカリ水洗浄に付すことにより有機溶媒を回収
する。有機溶媒は抽出精製にリサイクルされるのが一般
である。In the distillation step, the organic solvent liquid obtained in the acid decomposition step is neutralized, and the organic solvent is recovered by subjecting the neutralized organic solvent liquid to distillation or distillation and washing with alkaline water. Organic solvents are generally recycled for extraction and purification.
【００１７】上記の有機溶媒回収に際して、有機溶媒を
抽出精製にリサイクル使用するにあたり、アルカリ水溶
液のA値を１０以下に維持する。In recovering the organic solvent, the A value of the aqueous alkali solution is maintained at 10 or less when the organic solvent is recycled for extraction and purification.
【００１８】精製工程では、ＲＥＳを製品として得る。In the purification step, RES is obtained as a product.
【００１９】[0019]
【実施例】次に、実施例により、本発明を説明する。 実施例１ ＭＤＣの酸化で得られた反応液６０ｇと調合水酸化ナト
リウム水溶液(Ａ値＝０)３０ｇを用いて、ＭＨＰＯ劣化
率の測定を実施した。装置としてはコンデンサ付き２０
０ｃｃフラスコを用い、温度は７０℃で２時間攪拌し
た。このサンプルを取り、Ｔ−ＭＨＰＯの分析を行なう
ことにより、劣化率を求めた結果を表１に示した。なお
「Ｔ−ＭＨＰＯ」は実験液中のヒドロペルオキシド類を
滴定してＭＨＰＯに重量換算した数値を表す。Next, the present invention will be described by way of examples. Example 1 The MHPO deterioration rate was measured using 60 g of the reaction solution obtained by oxidation of MDC and 30 g of the prepared aqueous sodium hydroxide solution (A value = 0). The device has a condenser 20
The mixture was stirred at 70 ° C. for 2 hours using a 0 cc flask. Table 1 shows the results of obtaining the deterioration rate by taking this sample and analyzing the T-MHPO. In addition, "T-MHPO" represents a numerical value obtained by titrating hydroperoxides in a test solution and converting the weight into MHPO.
【００２０】実施例２及び比較例１ Ａ値が異なる水酸化ナトリウム水溶液を用いたこと以
外、実施例１と同様に行った。結果を表１に示した。Example 2 and Comparative Example 1 The same procedure as in Example 1 was carried out except that aqueous sodium hydroxide solutions having different A values were used. The results are shown in Table 1.
【００２１】[0021]
【表１】Ｔ−ＭＨＰＯ劣化率（％） Ｔ−ＭＨＰＯ劣化率（％）＝((保持時間後の実験液中の
Ｔ−ＭＨＰＯ量)−(実験開始直後の実験液中のＴ−ＭＨ
ＰＯ量))×１００／(実験開始直後の実験液中のＴ−Ｍ
ＨＰＯ量)[Table 1] T-MHPO deterioration rate (%) T-MHPO degradation rate (%) = ((T-MHPO amount in test solution after holding time) − (T-MH in test solution immediately after start of experiment)
PO amount) × 100 / (TM in the test solution immediately after the start of the experiment)
HPO amount)
【００２２】[0022]
【発明の効果】以上説明したとおり、本発明により、ア
ルカリ水溶液中でのヒドロペルオキシド類の分解による
損失が抑制される。すなわち、アルキル芳香族炭化水素
の酸化で得られるヒドロペルオキシド類が含まれる液か
ら、少なくとも一種のヒドロペルオキシド類をアルカリ
水溶液を用いて抽出精製する方法であって、精製工程中
におけるヒドロペルオキシドの分解による損失を抑制
し、よって経済的に有利な条件下に実施し得るヒドロペ
ルオキシドの精製方法を提供することができた。As described above, according to the present invention, the loss due to the decomposition of hydroperoxides in an aqueous alkaline solution is suppressed. That is, a method of extracting and purifying at least one hydroperoxide from an aqueous solution containing hydroperoxides obtained by oxidation of an alkyl aromatic hydrocarbon using an aqueous alkali solution, wherein the hydroperoxide is obtained by decomposition of the hydroperoxide during the purification step. It has been possible to provide a method for purifying hydroperoxide which can suppress loss and can be carried out under economically advantageous conditions.
【手続補正書】[Procedure amendment]
【提出日】平成１２年９月１３日（２０００．９．１
３）[Submission date] September 13, 2000 (2009.1)
3)
【手続補正１】[Procedure amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】０００９[Correction target item name] 0009
【補正方法】変更[Correction method] Change
【補正内容】[Correction contents]
【０００９】なお、「ＭＤＣ」は１，３−ジイソプロピ
ルベンゼンを表し、「ＭＨＰＯ」は３−イソプロピル−
１−（２−ヒドロペルオキシ−２−プロピル）−ベンゼ
ンを表し、「ＤＨＰＯ」は１，３−ジ−（２−ヒドロペ
ルオキシ−２−プロピル）−ベンゼンを表し、「ＣＨＰ
Ｏ」は３−（２−ヒドロキシ−２−プロピル）−１−
（２−ヒドロペルオキシ−２−プロピル）−ベンゼンを
表し、「ＭＩＢＫ」はメチルイソブチルケトンを表し、
「ＲＥＳ」はレゾルシノールを表し、「ＡＣＴ」はアセ
トンを表す。Note that "MDC" represents 1,3-diisopropylbenzene, and "MHPO" is 3-isopropyl-
Represents 1- (2-hydroperoxy-2-propyl) -benzene, "DHPO" represents 1,3-di- (2-hydroperoxy-2-propyl) -benzene, and represents "CHP
“O” is 3- (2-hydroxy-2-propyl) -1-
Represents (2-hydroperoxy-2-propyl) -benzene, "MIBK" represents methyl isobutyl ketone ,
“RES” stands for resorcinol and “ACT” stands for acetone.
Claims (1)
るヒドロペルオキシド類が含まれる液から、少なくとも
一種のヒドロペルオキシド類をアルカリ水溶液を用いて
抽出精製する方法であって、下記で定義されるA値が１
０以下であるアルカリ水溶液を用いるヒドロペルオキシ
ド類の抽出精製方法。 Ａ：アルカリ水溶液１０ｍｌを１規定の塩酸水溶液で滴
定して得られるｐＨ滴定曲線の第一変曲点から第二変曲
点までの間に消費された塩酸水溶液の容量（ｍｌ）であ
る。ただし、変曲点が明確でない場合又は変曲点を３個
以上有する場合は、ｐＨ７からｐＨ２までの間に消費さ
れた塩酸水溶液の容量（ｍｌ）である。1. A method for extracting and purifying at least one hydroperoxide from a liquid containing hydroperoxides obtained by oxidation of an alkyl aromatic hydrocarbon using an aqueous alkali solution, wherein A Value is 1
A method for extracting and purifying hydroperoxides using an aqueous alkaline solution of 0 or less. A: The volume (ml) of the aqueous hydrochloric acid solution consumed between the first inflection point and the second inflection point of the pH titration curve obtained by titrating 10 ml of the aqueous alkaline solution with a 1N aqueous hydrochloric acid solution. However, when the inflection point is not clear or has three or more inflection points, it is the volume (ml) of the hydrochloric acid aqueous solution consumed between pH 7 and pH 2.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000016281A JP4018307B2 (en) | 2000-01-25 | 2000-01-25 | Extraction and purification method of hydroperoxides |
| US09/730,583 US6369278B2 (en) | 1999-12-21 | 2000-12-07 | Process for preparing extract containing at least one hydroperoxide |
| CA002328629A CA2328629A1 (en) | 1999-12-21 | 2000-12-15 | Process for preparing extract containing at least one hydroperoxide |
| BE2000/0797A BE1014017A3 (en) | 1999-12-21 | 2000-12-18 | PROCESS FOR THE PREPARATION OF AN EXTRACT CONTAINING AT LEAST ONE HYDROPEROXIDE. |
| DE10063065A DE10063065A1 (en) | 1999-12-21 | 2000-12-18 | Process for the preparation of an extract containing at least one hydroperoxide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000016281A JP4018307B2 (en) | 2000-01-25 | 2000-01-25 | Extraction and purification method of hydroperoxides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001206874A true JP2001206874A (en) | 2001-07-31 |
| JP4018307B2 JP4018307B2 (en) | 2007-12-05 |
Family
ID=18543442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000016281A Expired - Fee Related JP4018307B2 (en) | 1999-12-21 | 2000-01-25 | Extraction and purification method of hydroperoxides |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4018307B2 (en) |
-
2000
- 2000-01-25 JP JP2000016281A patent/JP4018307B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP4018307B2 (en) | 2007-12-05 |
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