JPH0739384B2 - Method for producing organic peroxide - Google Patents
Method for producing organic peroxideInfo
- Publication number
- JPH0739384B2 JPH0739384B2 JP61053080A JP5308086A JPH0739384B2 JP H0739384 B2 JPH0739384 B2 JP H0739384B2 JP 61053080 A JP61053080 A JP 61053080A JP 5308086 A JP5308086 A JP 5308086A JP H0739384 B2 JPH0739384 B2 JP H0739384B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- group
- alkyl group
- formula
- ruthenium
- 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 - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001451 organic peroxides Chemical class 0.000 title description 2
- -1 polycyclic compound Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052707 ruthenium Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 150000002978 peroxides Chemical class 0.000 description 7
- 150000003512 tertiary amines Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RXMTUVIKZRXSSM-UHFFFAOYSA-N 2,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(CN)C1=CC=CC=C1 RXMTUVIKZRXSSM-UHFFFAOYSA-N 0.000 description 1
- IONGEXNDPXANJD-UHFFFAOYSA-N 4-chloro-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(Cl)C=C1 IONGEXNDPXANJD-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- LKUBHNYMHSNNRW-UHFFFAOYSA-N N-benzyl-N,2-diethylaniline Chemical compound C(C)C1=C(N(CC2=CC=CC=C2)CC)C=CC=C1 LKUBHNYMHSNNRW-UHFFFAOYSA-N 0.000 description 1
- ROZSPJBPUVWBHW-UHFFFAOYSA-N [Ru]=O Chemical class [Ru]=O ROZSPJBPUVWBHW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 150000004800 hydroisoquinoline derivatives Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- FZPXKEPZZOEPGX-UHFFFAOYSA-N n,n-dibutylaniline Chemical compound CCCCN(CCCC)C1=CC=CC=C1 FZPXKEPZZOEPGX-UHFFFAOYSA-N 0.000 description 1
- GBCKRQRXNXQQPW-UHFFFAOYSA-N n,n-dimethylprop-2-en-1-amine Chemical compound CN(C)CC=C GBCKRQRXNXQQPW-UHFFFAOYSA-N 0.000 description 1
- FQILZCAXBBSGEC-UHFFFAOYSA-N n-benzyl-n,2-dimethylaniline Chemical compound C=1C=CC=C(C)C=1N(C)CC1=CC=CC=C1 FQILZCAXBBSGEC-UHFFFAOYSA-N 0.000 description 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- OJLCQGGSMYKWEK-UHFFFAOYSA-K ruthenium(3+);triacetate Chemical compound [Ru+3].CC([O-])=O.CC([O-])=O.CC([O-])=O OJLCQGGSMYKWEK-UHFFFAOYSA-K 0.000 description 1
- WYRXRHOISWEUST-UHFFFAOYSA-K ruthenium(3+);tribromide Chemical compound [Br-].[Br-].[Br-].[Ru+3] WYRXRHOISWEUST-UHFFFAOYSA-K 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
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
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 本発明は有機過酸化物の製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing an organic peroxide.
更に詳しくは、 本発明は、一般式（Ｉ） （式中、R1、R2およびR3はそれぞれ独立に水素原子、ア
ルキル基、シクロアルキル基、アルケニル基または置換
されていてもよいフェニル基を表わすか、あるいはR2と
R3が結合し、単環式もしくは多環式の化合物を形成して
もよい。但しR1、R2およびR3が同時にアルキル基をとる
ことはない。） で示される過酸化物の製造法に関する。More specifically, the present invention relates to general formula (I) (In the formula, R 1 , R 2 and R 3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group or an optionally substituted phenyl group, or R 2 and
R 3 may combine to form a monocyclic or polycyclic compound. However, R 1 , R 2 and R 3 do not simultaneously take an alkyl group. ) Relates to a method for producing a peroxide.
一般式（Ｉ）で示される過酸化物は、医薬、農薬等の中
間体、添加剤をはじめとして種々の用途に用いられる重
合な化合物である。The peroxide represented by the general formula (I) is a polymerizable compound used for various purposes such as intermediates and additives of medicines and agricultural chemicals.
本発明者らは、ルテニウム触媒の存在下、一般式（II
I） R4OOH （III） （式中、R4はアルキル基を示す。） で示されるヒドロペルオキシドと一般式（II） （式中、R1、R2およびR3はそれぞれ独立に水素原子、ア
ルキル基、シクロアルキル基、アルケニル基または置換
されていてもよいフェニル基を表わすか、あるいはR2と
R3が結合し、単環式もしくは多環式の化合物を形成して
もよい。但しR1、R2およびR3が同時にアルキル基をとる
ことはない。） で示される３級アミンを反応させると極めて容易に一般
式（Ｉ）で示される過酸化物が得られることを見い出し
本発明を完成した。In the presence of a ruthenium catalyst, the inventors of the present invention have the general formula (II
I) R 4 OOH (III) (wherein R 4 represents an alkyl group) and the general formula (II) (In the formula, R 1 , R 2 and R 3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group or an optionally substituted phenyl group, or R 2 and
R 3 may combine to form a monocyclic or polycyclic compound. However, R 1 , R 2 and R 3 do not simultaneously take an alkyl group. The present invention was completed by finding that a peroxide represented by the general formula (I) can be obtained very easily by reacting a tertiary amine represented by
本発明において、原料となる３級アミン（II）は容易に
入手できるものであるが、必要ならば以下に示すルート
により容易に合成することができる。In the present invention, the tertiary amine (II) as a raw material is easily available, but if necessary, it can be easily synthesized by the route shown below.
（式中、R1、R2、R3は前記の意味を有し、Ｘはハロゲン
原子を示す。） かかる３級アミンとしては、R1、R2またはR3が水素原
子、C1〜C8のアルキル基、C5〜C7のシクロアルキル基、
C3〜C8のアルケニル基、またはハロゲン原子、C1〜C5の
アルキル基、アルコキシ基等により置換されていてもよ
いフェニル基であるか、あるいはR2とR3が結合してモル
ホリノ基のごとき単環式の化合物あるいはヒドロイソキ
ノリン、キノリンのごとき多環式の化合物を形成して得
られる化合物があげられる。具体的には、たとえば以下
のものが例示される。 (In the formula, R 1 , R 2 and R 3 have the above-mentioned meanings and X represents a halogen atom.) As such a tertiary amine, R 1 , R 2 or R 3 is a hydrogen atom, and C 1 to alkyl C 8, a cycloalkyl group of C 5 -C 7,
A C 3 -C 8 alkenyl group, or a phenyl group which may be substituted with a halogen atom, a C 1 -C 5 alkyl group, an alkoxy group, or the like, or a morpholino group in which R 2 and R 3 are bonded. And a compound obtained by forming a polycyclic compound such as hydroisoquinoline or quinoline. Specifically, the following are exemplified.
ジメチルアニリン、ジエチルアニリン、ジブチルアニリ
ン、ジフェニルメチルアミン、ジフェニルエチルアミ
ン、ジメチルアリルアミン、Ｎ−フェニルヒドロイソキ
ノリン、Ｎ−メチルヒドロイソキノリン、Ｎ−メチルヒ
ドロキノリン、ジメチルベンジルアニリン、ジエチルベ
ンジルアニリン、ジメチル−４−メチルアニリン、ジメ
チル−４−クロルアニリン、ジメチル−４−メトキシア
ニリン もう一方の原料であるヒドロペルオキシド（III）は、
たとえば一般に容易に入手できるｔ−ブチルヒドロペル
オキシドが好んで用いられる。Dimethylaniline, diethylaniline, dibutylaniline, diphenylmethylamine, diphenylethylamine, dimethylallylamine, N-phenylhydroisoquinoline, N-methylhydroisoquinoline, N-methylhydroquinoline, dimethylbenzylaniline, diethylbenzylaniline, dimethyl-4-methyl Aniline, dimethyl-4-chloroaniline, dimethyl-4-methoxyaniline Hydroperoxide (III) which is the other raw material is
For example, t-butyl hydroperoxide, which is generally readily available, is preferably used.
一般式（III）で示されるヒドロペルオキシドと一般式
（II）で示される３級アミンの反応は、通常、有機溶媒
の存在下にルテニウム触媒を用いて実施される。The reaction between the hydroperoxide represented by the general formula (III) and the tertiary amine represented by the general formula (II) is usually carried out using a ruthenium catalyst in the presence of an organic solvent.
有機溶媒を使用する場合、有機溶媒としては、ベンゼ
ン、トルエン、クロルベンゼン、クロロホルム、ジクロ
ルメタン、エチルエーテル、ジオキサン、テトラヒドロ
フラン、酢酸エチル、アセトン、メチルエチルケトン、
ヘキサン、石油エーテル等の反応に不活性な溶媒の単独
もしくは混合物が例示される。When using an organic solvent, as the organic solvent, benzene, toluene, chlorobenzene, chloroform, dichloromethane, ethyl ether, dioxane, tetrahydrofuran, ethyl acetate, acetone, methyl ethyl ketone,
Solvents such as hexane and petroleum ether, which are inert to the reaction, may be used alone or as a mixture.
一般式（III）で示されるヒドロペルオキシドの使用モ
ル比は、もう一方の原料である３級アミンに対して通常
２当量以上好ましくは２〜５当量の範囲で使用される。The molar ratio of the hydroperoxide represented by the general formula (III) to be used is usually in the range of 2 equivalents or more, preferably 2 to 5 equivalents, relative to the tertiary amine which is the other raw material.
ルテニウム触媒としては、通常、ルテニウムクロリド、
ルテニウムブロミドの如きルテニウムのハロゲン化物、
酢酸ルテニウムの如きルテニウムのカルボン酸塩、ルテ
ニウムの酸化物、さらには上記塩と他の化合物との錯体
等の種々のルテニウム触媒が例示されるが、好ましくは
ルテニウムのハロゲン化物である。ルテニウムのハロゲ
ン化物はこのままでも使用可能であるが、好ましくは、
下記式で示されるホスフィンとの化合として利用され
る。The ruthenium catalyst is usually ruthenium chloride,
Ruthenium halides such as ruthenium bromide,
Examples thereof include ruthenium carboxylates such as ruthenium acetate, ruthenium oxides, and various ruthenium catalysts such as complexes of the above salts with other compounds. Ruthenium halides are preferable. The ruthenium halide can be used as it is, but preferably,
It is used as a compound with a phosphine represented by the following formula.
RuX2（PR′３）３ （式中、Ｘはハロゲン原子、Ｒ′はアルキル基、シクロ
アルキル基、またはフェニル、トリル、クロルフェニル
の如き未置換もしくは置換フェニル基を示す。） その使用量は、通常、３級アミン（II）に対し0.1〜20
モル％の範囲である。もちろんこの範囲外でも使用でき
るが、特に大量用いる必要はない。RuX 2 (PR ′ 3 ) 3 (In the formula, X represents a halogen atom, R ′ represents an alkyl group, a cycloalkyl group, or an unsubstituted or substituted phenyl group such as phenyl, tolyl, chlorophenyl.) , Usually 0.1 to 20 for tertiary amine (II)
It is in the range of mol%. Of course, it can be used outside this range, but it is not necessary to use a large amount.
反応温度は−20〜100℃、好ましくは−10〜80℃の範囲
であり、反応時間については特に制限はない。The reaction temperature is in the range of -20 to 100 ° C, preferably -10 to 80 ° C, and the reaction time is not particularly limited.
このような反応により、目的の一般式（Ｉ）で示される
過酸化物が容易に、好収率で得られる。反応混合物から
目的の過酸化物の単離は、通常反応混合物をそのまま濃
縮するか、あるいは必要により濃縮残渣をシリカゲルカ
ラムクロマトグラフィーにより精製処理することにより
行うことができる。By such a reaction, the desired peroxide represented by the general formula (I) can be easily obtained in a good yield. The desired peroxide can be isolated from the reaction mixture by concentrating the reaction mixture as it is, or by purifying the concentrated residue by silica gel column chromatography if necessary.
かくして、本発明の方法により一般式（Ｉ）で示される
過酸化物が工業的容易に、しかも収率よく製造すること
ができる。Thus, by the method of the present invention, the peroxide represented by the general formula (I) can be produced industrially easily and in good yield.
以下、実施例により本発明を説明する。Hereinafter, the present invention will be described with reference to examples.
実施例１ 撹拌装置、温度計、滴下ロートを装着した４ツ口フラス
コにジメチルアニリン２ミリモル、RuCl2（Pph3）3 0.0
6ミリモルおよび無水ベンゼン3mlを仕込む。室温にて、
ｔ−ブチルヒドロペルオキシド６ミリモルのベンゼン4m
l溶液を３時間かかって滴下する。同温度にて15時間保
温したのち、反応液を減圧濃縮する。濃縮残渣をエチル
エーテル−ヘキサンの混合溶液を用い、シリカゲルカラ
ムクロマトグラフィーに精製する。ｔ−ブチルヒドロペ
ルオキシドジメチルアニリン1.98ミリモル（収率99％）
を得た。Example 1 2 mmol of dimethylaniline and RuCl 2 (Pph 3 ) 3 0.0 were placed in a 4-necked flask equipped with a stirrer, a thermometer and a dropping funnel.
Charge 6 mmol and 3 ml of anhydrous benzene. At room temperature
t-Butyl hydroperoxide 6 mmol benzene 4 m
l Add solution dropwise over 3 hours. After incubating at the same temperature for 15 hours, the reaction solution is concentrated under reduced pressure. The concentrated residue is purified by silica gel column chromatography using a mixed solution of ethyl ether-hexane. t-Butyl hydroperoxide dimethylaniline 1.98 mmol (99% yield)
Got
IR（neat）ν（cm-1）1200（ｓ、ｃ−ｏ）、875（ｓ、
ｏ−ｏ）； H1NMR（CDCl3、60MHz）δ1.20（ｓ、9H）、3.10（ｓ、3
H）、5.10（ｓ、2H）、6.50−7.40（ｍ、5H） 実施例２〜４ 実施例１で用いたジメチルアニリンに代えて、それと等
モルの表−１に記載の３級アミンを使用する以外は実施
例１と同様に反応、後処理して表−１に示す過酸化物を
得た。 IR (neat) ν (cm -1 ) 1200 (s, co), 875 (s,
oo); H 1 NMR (CDCl 3 , 60 MHz) δ1.20 (s, 9H), 3.10 (s, 3)
H), 5.10 (s, 2H), 6.50-7.40 (m, 5H) Examples 2 to 4 Instead of dimethylaniline used in Example 1, equimolar tertiary amines shown in Table 1 were used. The same reaction and post-treatment as in Example 1 except that the peroxides shown in Table 1 were obtained.
Claims (1)
ルキル基、シクロアルキル基、アルケニル基または置換
されていてもよいフェニル基を表わすか、あるいはR2と
R3が結合して単環式もしくは多環式の化合物を形成して
もよい。但しR1、R2およびR3が同時にアルキル基をとる
ことはない。） で示される３級アミンをルテニウム触媒の存在下、一般
式（III） R4OOH （III） （式中、R4はアルキル基を示す。） で示されるヒドロペルオキシドと反応させることを特徴
とする一般式（Ｉ） （式中、R1、R2、R3およびR4は前記と同じ意味を有す
る。） で示される有機過酸化物の製造方法。1. General formula (II) (In the formula, R 1 , R 2 and R 3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group or an optionally substituted phenyl group, or R 2 and
R 3 may combine to form a monocyclic or polycyclic compound. However, R 1 , R 2 and R 3 do not simultaneously take an alkyl group. ) Is reacted with a hydroperoxide represented by the general formula (III) R 4 OOH (III) (wherein R 4 represents an alkyl group) in the presence of a ruthenium catalyst. General formula (I) (In the formula, R 1 , R 2 , R 3 and R 4 have the same meanings as described above.).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61053080A JPH0739384B2 (en) | 1986-03-11 | 1986-03-11 | Method for producing organic peroxide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61053080A JPH0739384B2 (en) | 1986-03-11 | 1986-03-11 | Method for producing organic peroxide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62212360A JPS62212360A (en) | 1987-09-18 |
| JPH0739384B2 true JPH0739384B2 (en) | 1995-05-01 |
Family
ID=12932819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61053080A Expired - Lifetime JPH0739384B2 (en) | 1986-03-11 | 1986-03-11 | Method for producing organic peroxide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0739384B2 (en) |
-
1986
- 1986-03-11 JP JP61053080A patent/JPH0739384B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62212360A (en) | 1987-09-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0739384B2 (en) | Method for producing organic peroxide | |
| EP0647647A1 (en) | Tertiary phosphine compound and transition metal complex comprising the same as ligand | |
| JPH07330786A (en) | Optically active tertiary phosphine compound, transition metal complex having this as a ligand, and production method using the same | |
| JPH0733391B2 (en) | Method for producing peroxides | |
| JP3010264B2 (en) | Method for producing isocoumarins | |
| JP3477631B2 (en) | Purification method of 1,3-bis (3-aminopropyl) -1,1,3,3-tetraorganodisiloxane | |
| JPS6212770B2 (en) | ||
| JP2736324B2 (en) | Synthesis of silylcyanohydrin | |
| JP4157968B2 (en) | Alkenyl phosphinate and process for producing the same | |
| JP4509327B2 (en) | Process for producing N, N-disubstituted-4-aminocrotonic acid ester | |
| JP4667589B2 (en) | Method for producing 2,4-dihydroxypyridine | |
| JP3278957B2 (en) | Method for producing 3-allylphenols | |
| EP0450957B1 (en) | Production of methylphenyltrisiloxane | |
| JP3531176B2 (en) | Method for producing optically active silyl compounds | |
| JPWO2005095317A1 (en) | Method for producing halogenated unsaturated carbonyl compound | |
| JP2001247586A (en) | Allyl phosphonate compound and method for producing the same | |
| KR100619435B1 (en) | New Manufacturing Method of Amide | |
| JPH09295993A (en) | Production of alkenylphosphine oxide compound | |
| RU2283828C1 (en) | Method for production of 2,9-dimethyl-4,7-dialkyl(benzyl)iden-1,9-decadiens | |
| JPH0737467B2 (en) | Method for producing tert-butyltrialkoxysilane | |
| JPH115769A (en) | Production of tertiary amines | |
| KR100619436B1 (en) | Amide Manufacturing Method Using Diphosgene | |
| JP3348456B2 (en) | Method for producing p-quinones | |
| JPH0751585B2 (en) | Method for producing trimethylsilylated cyanohydrin | |
| JPH0376313B2 (en) |