JPH0330584B2 - - Google Patents
Info
- Publication number
- JPH0330584B2 JPH0330584B2 JP57030222A JP3022282A JPH0330584B2 JP H0330584 B2 JPH0330584 B2 JP H0330584B2 JP 57030222 A JP57030222 A JP 57030222A JP 3022282 A JP3022282 A JP 3022282A JP H0330584 B2 JPH0330584 B2 JP H0330584B2
- Authority
- JP
- Japan
- Prior art keywords
- acetone
- treatment
- alkali
- present
- hydrogen peroxide
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 92
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 31
- 239000003513 alkali Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- -1 2-hydroperoxy-2-propyl group Chemical group 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000011282 treatment Methods 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000012286 potassium permanganate Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- 229930007927 cymene Natural products 0.000 description 6
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 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 description 1
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- QBEZHXMLBPSPCU-UHFFFAOYSA-N hydrogen peroxide;1-propan-2-ylnaphthalene Chemical compound OO.C1=CC=C2C(C(C)C)=CC=CC2=C1 QBEZHXMLBPSPCU-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明はアセトンの精製方法に関し、さらに詳
しくは、２−ヒドロペルオキシ−２−プロピル基
を有する芳香族化合物を分解した反応液から得ら
れた粗アセトンを、過酸化水素とアルカリで処理
することを特徴とする粗アセトンの精製方法に関
する。Detailed Description of the Invention The present invention relates to a method for purifying acetone, and more specifically, crude acetone obtained from a reaction solution obtained by decomposing an aromatic compound having a 2-hydroperoxy-2-propyl group is purified by hydrogen peroxide. The present invention relates to a method for purifying crude acetone, characterized by treating it with alkali and alkali.
ヒドロペルオキシドを経由して製造したアセト
ンの精製方法として、粗アセトンをアルカリと接
触させる方法が従来知られている。この方法は、
粗アセトンをアルカリ処理し、次いでアルカリを
中和した後、精留してアセトンを回収する方法で
あり、このアルカリ処理によつて、アセトンの品
質規格で要求される過マンガン酸カリテスト
（JISK−1503）で許容されうる品質に到達すると
されていた。しかしながら、このアルカリ処理を
行つても、満足のできる高品質アセトンを得るこ
とが困難な場合があり、より確実に高品質アセト
ンが得られる効果的なアセトンの精製法が求めら
れていた。 As a method for purifying acetone produced via hydroperoxide, a method in which crude acetone is brought into contact with an alkali is conventionally known. This method is
This is a method of treating crude acetone with an alkali, then neutralizing the alkali, and then rectifying it to recover acetone. ) was considered to reach acceptable quality. However, even with this alkali treatment, it is sometimes difficult to obtain satisfactory high-quality acetone, and there has been a need for an effective acetone purification method that can more reliably obtain high-quality acetone.
本発明は、この様なアセトン精製上の問題点を
解消し、より確実に品質上問題のないアセトンを
回収する方法を提供するものである。 The present invention solves these problems in refining acetone and provides a method for more reliably recovering acetone without any quality problems.
ヒドロペルオキシドを経由して製造した粗アセ
トンとは、キユメンヒドロペルオキシド、シメン
ヒドロペルオキシド、ジイソプロピルベンゼンモ
ノ（又はジ）ヒドロペルオキシド、イソプロピル
ナフタレンヒドロペルオキシド等の様に、２−ヒ
ドロペルオキシ−２−プロピル基を有する芳香族
化合物を、各種の触媒（例えば硫酸、無水硫酸、
過塩素酸、硫黄、含硫黄化合物、イオン交換樹
脂、固体酸触媒等のヒドロペルオキシドの分解触
媒）を用いて分解し、生成したアセトンを反応液
から蒸留等の方法で回収したものであるが、この
中にはアセトンの他に量的には少いものの、何種
類かのアセトンと沸点の接近した不純物が含まれ
ており、通常単に蒸留処理をしただけでは、アセ
トンの品質分析である過マンガン酸カリテストに
合格する品質のものにならない。過マンガン酸カ
リテストに不合格となる原因物質としては、粗ア
セトン中に含有される不純物であるアセトアルデ
ヒド等のアルデヒド類が公知であり、これらのア
ルデヒドは、粗アセトンをアルカリと接触させる
アルカリ処理を行えば、アルドール縮合により、
高沸点物となるため、次に精留を行うことによつ
て分離除去することが可能である。しかし、これ
らのアルデヒド類以外にも、粗アセトン中には不
純物が存在し、アルカリ処理を行つても高品質の
アセトンが得られず、過マンガン酸カリテストで
不合格となることがあつた。本発明は、この様に
通常のアルカリ処理だけでは、充分に高品質化精
製の目的が達成できず、過マンガン酸カリテスト
で不合格となりやすい粗アセトンの精製をより確
実にするための新しい処理方法であり、具体的に
は、アルカリと過酸化水素を併用使用することを
特徴とする処理方法である。 Crude acetone produced via hydroperoxide refers to 2-hydroperoxy-2-propyl group, such as cymene hydroperoxide, cymene hydroperoxide, diisopropylbenzene mono(or di)hydroperoxide, isopropylnaphthalene hydroperoxide, etc. The aromatic compound having
Hydroperoxide decomposition catalysts such as perchloric acid, sulfur, sulfur-containing compounds, ion exchange resins, and solid acid catalysts are used to decompose the acetone, and the acetone produced is recovered from the reaction solution by distillation or other methods. In addition to acetone, this contains several types of impurities that have boiling points close to acetone, although in small amounts. The quality will not pass the acid potash test. Aldehydes such as acetaldehyde, which are impurities contained in crude acetone, are known to be the cause of failure in the potassium permanganate test. For example, by aldol condensation,
Since it is a high boiling point substance, it can be separated and removed by subsequent rectification. However, in addition to these aldehydes, there are other impurities in crude acetone, and even with alkali treatment, high-quality acetone cannot be obtained, and it sometimes fails the potassium permanganate test. The present invention is a new treatment method for more reliably refining crude acetone, which cannot achieve the purpose of high-quality purification with ordinary alkali treatment alone and is likely to fail the potassium permanganate test. Specifically, this treatment method is characterized by using alkali and hydrogen peroxide in combination.
すなわち、ヒドロペルオキシドを経由して生成
したアセトンを回収精製していく工程の中に、粗
アセトンを、水の共存下で、アルカリ性物質およ
び過酸化水素と、接触させる処理工程を含むこと
を特徴とするアセトンの精製方法である。 That is, the process of recovering and refining acetone produced via hydroperoxide includes a treatment process of bringing crude acetone into contact with an alkaline substance and hydrogen peroxide in the presence of water. This is a method for purifying acetone.
本発明において処理すべき粗アセトンは、ヒド
ロペルオキシドを経由して製造回収したものであ
つて、粗アセトンの回収方法に従い、本発明の処
理で除去される不純物ばかりでなく、他の不純物
（例えば、キユメンやシメン等）が混入していて
も、又、水や塩類、無機物等を含有するものであ
つても本発明の効果を期待することが可能であ
る。 The crude acetone to be treated in the present invention is produced and recovered via hydroperoxide, and according to the crude acetone recovery method, not only the impurities removed by the treatment of the present invention but also other impurities (e.g. The effects of the present invention can be expected even if substances such as cymene, cymene, etc.) are mixed in, or even if they contain water, salts, inorganic substances, etc.
本発明で、過酸化水素とともに用いるアルカリ
としては、例えば、苛性ソーダ、苛性カリ、ナト
リウム塩類、カリウム塩類等が例示される。アル
カリの使用量としては、粗アセトンに対して0.01
〜５％（重量）が望ましい。 In the present invention, examples of the alkali used together with hydrogen peroxide include caustic soda, caustic potash, sodium salts, potassium salts, and the like. The amount of alkali used is 0.01 per crude acetone.
~5% (by weight) is desirable.
本発明の処理においては、処理系内に水が共存
していることが望ましいが、水の共存量は本処理
系内に存在するアセトンに対して10〜50％（重
量）が適当である。 In the treatment of the present invention, it is desirable that water coexist in the treatment system, and the appropriate amount of water coexisting is 10 to 50% (by weight) of the acetone present in the treatment system.
本発明の特徴である過酸化水素の使用量は粗ア
セトンに対して0.001から１％（重量）が適当で
ある。使用する過酸化水素は高濃度品であつて
も、低濃度品であつても差しつかえない。 The appropriate amount of hydrogen peroxide, which is a feature of the present invention, is 0.001 to 1% (by weight) based on crude acetone. The hydrogen peroxide used may be a high-concentration product or a low-concentration product.
本発明の処理は、回分、連続のいづれの処理法
であつてもその効果を期待できるものである。
又、本発明の処理を、従来行なわれてきた粗アセ
トンのアルカリ処理と独立して、アルカリ処理を
行う前、又は、行つた後に実施しても差しつかえ
ないが、本発明の処理もアルカリ共存下で行うの
であるから、アルカリ処理と同時に実施するのが
効果的といえる。この場合、過酸化水素の共給
は、アルカリや水の供給と同時に行う必要はな
く、例えば、アルカリ処理を２段の連続処理で行
つている場合、２段目に過酸化水素を供給するこ
とも可能である。 The effects of the treatment of the present invention can be expected regardless of whether it is a batch or continuous treatment method.
Furthermore, the treatment of the present invention may be carried out independently of the conventional alkali treatment of crude acetone, before or after the alkali treatment; Since it is carried out below, it can be said that it is effective to carry out it at the same time as the alkaline treatment. In this case, it is not necessary to co-supply hydrogen peroxide at the same time as the supply of alkali and water; for example, if alkali treatment is performed in two consecutive stages, hydrogen peroxide may be supplied to the second stage. is also possible.
本発明の処理は、通常０℃から100℃の範囲で
実施されるが、30℃から70℃の範囲で行うのが好
ましい。 The treatment of the present invention is usually carried out at a temperature in the range of 0°C to 100°C, preferably in the range of 30°C to 70°C.
本発明の処理をした後（さらにアルカリ処理等
の精製処理を行う場合には、これらの処理をした
後）、アルカリ分が混入している場合には、酸性
物質を用いて中和又は除去して、精留を行い、高
品質アセトンを留出回収する。 After the treatment of the present invention (if further purification treatment such as alkali treatment, after these treatments), if alkaline components are present, neutralize or remove them using an acidic substance. Then, perform rectification to recover high quality acetone.
後述する実施例では詳細に述べる様に、従来知
られているアルカリ処理の方法では、精留回収し
たアセトンが、過マンガン酸カリテストで、短時
間で退色してしまうのに対して、本発明に従つて
過酸化水素の存在下にアルカリ処理を行うと、精
留後回収したアセトンは過マンガン酸カリテスト
で、２時間以上退色が見られず、極めて高品質の
アセトンが得られる。従来知られているアルカリ
処理では除去できず、本発明の実施によつて除去
される（もしくは、変性し後の精留で除去され
る）物質が何であるかは明らかではないが、メル
カプタンの様な含イオウ化合物も関係しているも
のの１ツと予想される。 As will be described in detail in the examples below, in the conventionally known alkali treatment method, the acetone recovered by rectification fades in a short period of time in the potassium permanganate test. Therefore, when alkaline treatment is carried out in the presence of hydrogen peroxide, the acetone recovered after rectification shows no discoloration in the potassium permanganate test for more than 2 hours, and extremely high quality acetone can be obtained. Although it is not clear what substances are removed by the implementation of the present invention (or removed by rectification after denaturation) that cannot be removed by conventionally known alkali treatments, they are substances such as mercaptans. Sulfur-containing compounds are also expected to be involved.
以下本発明を実施例により説明するが、本発明
は、これらの実施例のみに限定されるものではな
い。 EXAMPLES The present invention will be explained below with reference to Examples, but the present invention is not limited to these Examples.
（尚実施例中に“部”とは重量部を意味し、
“％”とは重量％を意味する）
実施例 １
メタ、パラジイソプロピルベンゼンジヒドロペ
ルオキシドのメチルイソブチルケトン溶液を硫酸
を触媒として溶解し、中和、分液、ケトン類の精
留回収、メチルイソブチルケトンの精留分離等の
処理を経て得られた粗アセトン100部（アセトン
含有量98％）に、0.5％苛性ソーダ水溶液20部と
30％過酸化水素水0.1部を加え、50℃で10分間よ
く撹拌した後、希硫酸でPH７に中和し、精留し
て、精製アセトン93部を留出回収した。この精製
アセトンはJISK−1503過マンガン酸カリテスト
で２時間以上退色しなかつた。 (In the examples, "parts" means parts by weight,
("%" means % by weight) Example 1 A solution of meta, para diisopropylbenzene dihydroperoxide in methyl isobutyl ketone was dissolved using sulfuric acid as a catalyst, neutralization, liquid separation, rectification recovery of ketones, and methyl isobutyl ketone. To 100 parts of crude acetone (acetone content 98%) obtained through treatments such as rectification separation, add 20 parts of 0.5% caustic soda aqueous solution.
After adding 0.1 part of 30% hydrogen peroxide solution and stirring well at 50°C for 10 minutes, the mixture was neutralized to pH 7 with dilute sulfuric acid and rectified to recover 93 parts of purified acetone. This purified acetone did not discolor for more than 2 hours in the JISK-1503 potassium permanganate test.
実施例 ２
シメンヒドロペルオキシドを主成分として含有
するシメンの酸化反応液を硫酸を触媒として分解
し、中和、分液、精留等の処理で得られた粗アセ
トン100部（アセトン含有量95％）に、１％苛性
ソーダ水溶液15部と、30％過酸化水素水0.2部を
加え、50℃で10分間よく撹拌した後、希硫酸でPH
７に中和し、精留して、精製アセトン90部に留出
回収した。このものはJIS Ｋ−1503過マンガン酸
カリテストで２時間以上退色しなかつた。Example 2 A cymene oxidation reaction solution containing cymene hydroperoxide as a main component was decomposed using sulfuric acid as a catalyst, and 100 parts of crude acetone (acetone content 95%) was obtained by neutralization, separation, rectification, etc. ), add 15 parts of 1% aqueous sodium hydroxide solution and 0.2 part of 30% hydrogen peroxide solution, stir well at 50℃ for 10 minutes, and then PH with dilute sulfuric acid.
7 and rectified, and distilled and recovered in 90 parts of purified acetone. This product did not discolor for more than 2 hours in the JIS K-1503 potassium permanganate test.
比較例 １
実施例１と同様の粗アセトン100部に0.5％苛性
ソーダ水溶液20部を加え、50％で10分間よく撹拌
した後、希硫酸でPH７に中和し、精留して精製ア
セトン93部を留出回収した。この精製アセトン
は、JIS Ｋ−1503過マンガン酸カリテストで15分
以内に退色した。Comparative Example 1 Add 20 parts of a 0.5% caustic soda aqueous solution to 100 parts of the same crude acetone as in Example 1, stir well at 50% for 10 minutes, neutralize to pH 7 with dilute sulfuric acid, and rectify to obtain 93 parts of purified acetone. was distilled and recovered. This purified acetone faded within 15 minutes using the JIS K-1503 potassium permanganate test.
Claims (1)
する芳香族化合物を分解した反応液から得られた
粗アセトンを、過酸化水素とアルカリで処理する
ことを特徴とする粗アセトンの精製方法。1. A method for purifying crude acetone, which comprises treating crude acetone obtained from a reaction solution obtained by decomposing an aromatic compound having a 2-hydroperoxy-2-propyl group with hydrogen peroxide and an alkali.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57030222A JPS58146529A (en) | 1982-02-25 | 1982-02-25 | Purification of acetone |
| DE19833305954 DE3305954A1 (en) | 1982-02-25 | 1983-02-21 | METHOD FOR PURIFYING ACETONE |
| IT47756/83A IT1164589B (en) | 1982-02-25 | 1983-02-22 | ACETONE PURIFICATION PROCEDURE |
| FR8302841A FR2521988A1 (en) | 1982-02-25 | 1983-02-22 | PROCESS FOR PURIFYING ACETONE |
| GB08305008A GB2116177A (en) | 1982-02-25 | 1983-02-23 | A method for purifying acetone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57030222A JPS58146529A (en) | 1982-02-25 | 1982-02-25 | Purification of acetone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58146529A JPS58146529A (en) | 1983-09-01 |
| JPH0330584B2 true JPH0330584B2 (en) | 1991-04-30 |
Family
ID=12297686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57030222A Granted JPS58146529A (en) | 1982-02-25 | 1982-02-25 | Purification of acetone |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS58146529A (en) |
| DE (1) | DE3305954A1 (en) |
| FR (1) | FR2521988A1 (en) |
| GB (1) | GB2116177A (en) |
| IT (1) | IT1164589B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6340777B1 (en) * | 1999-10-22 | 2002-01-22 | General Electric Company | Method for purifying acetone |
| US6303826B1 (en) * | 2000-01-19 | 2001-10-16 | Sunoco, Inc. (R&M) | Method for purification of acetone |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1287253A (en) * | 1961-04-27 | 1962-03-09 | It Resine Soc | Method of purification of acetone obtained by acid dissociation of cumene hydroperoxide |
-
1982
- 1982-02-25 JP JP57030222A patent/JPS58146529A/en active Granted
-
1983
- 1983-02-21 DE DE19833305954 patent/DE3305954A1/en not_active Withdrawn
- 1983-02-22 IT IT47756/83A patent/IT1164589B/en active
- 1983-02-22 FR FR8302841A patent/FR2521988A1/en not_active Withdrawn
- 1983-02-23 GB GB08305008A patent/GB2116177A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB8305008D0 (en) | 1983-03-30 |
| IT8347756A0 (en) | 1983-02-22 |
| GB2116177A (en) | 1983-09-21 |
| DE3305954A1 (en) | 1983-09-01 |
| JPS58146529A (en) | 1983-09-01 |
| IT1164589B (en) | 1987-04-15 |
| FR2521988A1 (en) | 1983-08-26 |
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