Process for producing hydrogen peroxide

Details Process for producing hydrogen peroxide Process for producing hydrogen peroxide

2000-10-06

2002-04-23

Langel, Wayne (Department: 1754)

Chemistry of inorganic compounds

Oxygen or compound thereof

Peroxide

Reexamination Certificate

active

06375922

ABSTRACT:

This application is the national phase under 35 U.S.C. § 371 of PCT International Application No. PCT/JP00/00528 which has an International filing date of Feb. 1, 2000, which designated the United States of America.
TECHNICAL FIELD
The present invention relates to a process for producing hydrogen peroxide which is useful as, for example, oxidizing agents, bleaching agents, disinfectants, and bactericides or fungicides.
BACKGROUND ART
As processes for the commercial production of hydrogen peroxide, (i) a process of reacting sulfuric acid with ammonia to yield an ammonium hydrogensulfate solution, adding an electrolysis accelerator to the solution to subject the solution to electrolysis and anodic oxidation to thereby form ammonium peroxodisulfate, adding sulfuric acid to ammonium peroxodisulfate to yield hydrogen peroxide, and distilling hydrogen peroxide in vacuo, and (ii) a process of utilizing autoxidation of 2-ethylanthraquinol or another anthraquinol compound to yield hydrogen peroxide are known. The former process, however, has complicated steps and costs dearly, and the latter process requires materials which are not so readily available.
DISCLOSURE OF INVENTION
Accordingly, it is an object of the present invention to provide a process capable of easily and efficiently obtaining hydrogen peroxide from readily available materials.
After intensive investigations to achieve the above object, the present inventors found that the oxidation of a primary or secondary alcohol with oxygen using an imide compound having a specific structure can efficiently yield hydrogen peroxide. The invention has been accomplished on the basis of the above finding.
Specifically, the invention provides a process for producing hydrogen peroxide, which process includes the step of reacting a primary or secondary alcohol with oxygen in the presence of an imide compound of the following formula (1):
wherein each of R
1
and R
2
s identical to or different from each other, a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cycloalkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group, or an acyl group, where R
1
and R
2
may be combined to form a double bond, or an aromatic or non-aromatic ring; X is an oxygen atom or a hydroxyl group; where one or two N-substituted cyclic imido groups indicated in the formula (1) may be further bonded to the aforementioned R
1
, R
2
, or to the double bond or aromatic or non-aromatic ring formed together by R
1
and R
2
, to yield hydrogen peroxide.
The primary or secondary alcohol(s) maybe simply referred to as “substrate(s)” in the present specification.
BEST MODE FOR CARRYING OUT THE INVENTION
[Substrate]
The primary or secondary alcohols include a wide variety of alcohols inclusive of monohydric, dihydric, and polyhydric alcohols. Each of the primary or secondary alcohols may have a substituent. Such substituents include, but are not limited to, halogen atoms, an oxo group, a hydroxyl group, a mercapto group, substituted oxy groups (e.g., alkoxy groups, aryloxy groups, and acyloxy groups), substituted thio groups, a carboxyl group, substituted oxycarbonyl groups, substituted or unsubstituted carbamoyl groups, a cyano group, a nitro group, substituted or unsubstituted amino groups, alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, cycloalkenyl groups, aryl groups (e.g., phenyl and naphthyl groups), aralkyl groups, and heterocyclic groups.
The primary alcohols include, but are not limited to, methanol, ethanol, 1-propanol, 1-butanol, 2-methyl-1-propanol, 1-pentanol, 1-hexanol, 1-octanol, 1-decanol, 1-hexadecanol, and other saturated or unsaturated aliphatic primary alcohols each having about 1 to 30 (preferably 1 to 20, and more preferably 1 to 15) carbon atoms; cyclopentylmethyl alcohol, cyclohexylmethyl alcohol, 2-cyclohexylethyl alcohol, and other saturated or unsaturated alicyclic primary alcohols; benzyl alcohol, 2-phenylethyl alcohol, 3-phenylpropyl alcohol, and other aromatic primary alcohols; and 2-hydroxymethylpyridine, and other heterocyclic primary alcohols. Preferred primary alcohols include saturated aliphatic primary alcohols each having about 1 to 20 carbon atoms, and other aliphatic primary alcohols.
Examples of the secondary alcohols include 2-propanol, s-butyl alcohol, 2-pentanol, 3-pentanol, 2-hexanol, 2-octanol, 4-decanol, 2-hexadecanol, and other saturated or unsaturated aliphatic secondary alcohols each having about 3 to 30 (preferably 3 to 20, and more preferably 3 to 15) carbon atoms; cyclobutanol, cyclopentanol, cyclohexanol, cyclooctanol, cyclododecanol, cyclopentadecanol, and other saturated or unsaturated alicyclic secondary alcohols each having about 3 to 20 (preferably 3 to 15, more preferably 5 to 15, and especially 5 to 8) members; 1-phenylethanol, 1-phenylpropanol, 1-phenylmethylethanol, benzhydrol (diphenylmethanol), 9,10-dihydroanthracene-9,10-diol and other aromatic secondary alcohols; and 1-(2-pyridyl)ethanol, and other heterocyclic secondary alcohols.
Preferred substrates include secondary alcohols such as s-butyl alcohol, 2-octanol, and other aliphatic secondary alcohols, cyclohexanol and other alicyclic secondary alcohols, 1-phenylethanol, benzhydrol, and other aromatic alcohols. Each of the aforementioned alcohols can be used alone or in combination.
[Imide Compound]
The imide compounds of the formula (1) are for use as a catalyst in the invented process. Of the substituents R
1
and R
2
in the formula (1), the halogen atom includes iodine, bromine, chlorine and fluorine atoms. The alkyl group includes, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, decyl, and other straight- or branched-chain alkyl groups each having about 1 to 10 carbon atoms. Preferred alkyl groups are alkyl groups each having about 1 to 6 carbon atoms, and are more preferably lower alkyl groups each having about 1 to 4 carbon atoms.
The aryl group includes phenyl, and naphthyl groups, for example; and the illustrative cycloalkyl group includes cyclopentyl, and cyclohexyl groups. As the alkoxy group, there may be mentioned, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, t-butoxy, pentyloxy, hexyloxy, and other alkoxy groups each having about 1 to 10 carbon atoms, preferably about 1 to 6 carbon atoms, of which lower alkoxy groups each having about 1 to 4 carbon atoms are especially preferred.
Examples of the alkoxycarbonyl group include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, t-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, and other alkoxycarbonyl groups each having about 1 to 10 carbon atoms in the alkoxy moiety. Preferred alkoxycarbonyl groups are alkoxycarbonyl groups each having about 1 to 6 carbon atoms in the alkoxy moiety, and are especially lower alkoxycarbonyl groups each having about 1 to 4 carbon atoms in the alkoxy moiety.
The illustrative acyl groups include, but are not limited to, formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, pivaloyl, and other acyl groups each having about 1 to 6 carbon atoms.
The substituents R
1
and R
2
maybe identical to, or different from each other. The substituents R
1
and R
2
in the formula (1) may be combined to form a double bond, or an aromatic or non-aromatic ring. The preferred aromatic or non-aromatic ring is a 5- to 12-membered ring, and especially a 6- to 10-membered ring. The ring may be a heterocyclic ring or condensed heterocyclic ring, but it is often a hydrocarbon ring. Such rings include, for example, non-aromatic alicyclic rings (e.g., cyclohexane ring and other cycloalkane rings which may have a substituent, cyclohexene ring and other cycloalkene rings which may have a substituent), non-aromatic bridged rings (e.g., 5-norbornene ring and other bridged hydrocarbon rings which may have a substituent), benzene ring, naphthalene ring and other aromatic rings (including condensed rings) which may have a substituent. The ring is compose

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