DE1518967A1 - Process for the production of epoxies - Google Patents

Description

Halcon International, Ino _u> New York, NY, V-St.A " Process for the production of epoxies

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The invention relates to a process for the production of epoxies. When carrying out the inventive lake Process are propylene, oxygen and alkylaromatieche Compounds with at least one hydrogen atom on one directly on the aromatic ring bonded carbon atom (preferably cumene or ethylbenzene) as the only starting materials required According to one embodiment of the process according to the invention, propylene oxide is produced by the epoxidation of propylene made with do-phenylethylhydroperoxide * where propylene, Oxygen and ethylbenzene are the only necessary starting materials and a by-product is formed

909836 / U87 BAD ORfGINAL.

will ,, Ultimately can dU-phenylethanol, styrene or acetophenone be. According to a further feature of the invention, as Noban product formed alcohol back into the original Hydrocarbon transferred so that one mode of operation is made possible, in which no by-product is formed, but hydrogen is consumed

The importance of propylene oxide and similar epoxy compounds as starting materials for the chemical industry is growing steadily. Intermediate products are used, the basic question of propylene oxide, which is also supposed to be more easily accessible up to now. For this, Ohlor is one of the main starting points. fabrics required. The custom of chlorine is converted into the sale of hydrochloric acid in the process in which it is not possible to recycle chlorine economically in the production process. This process sur.Herstellung of Propylonoxyd is therefore substantially less favorable than those of Her "tellung of ethylene oxide ₉ can dns be prepared using ethylene and oxygen as the main raw materials * Except propylene oxide ea are white tei * € Epoxyverblndungenj.die equally valuable HändeJsprodukte

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BATH ORIGINAL

represent, e.g., those of unsaturated esters and alcohols and of serving.

Ee is known to use low olefins in processes sum epoxidized, such as propylene, very reactive · Use substances such as peracids as epoacydation agents. For example has feracetic acid widespread in such epoxidations

Use found. Si · use of feracetic acid · is Je- | but not satisfactory for two reasons, and once, because a sienlioh great effort is required to produce it

• ■ *

is necessary and, on the other hand, because the ^{acetic acid formed as a by-product 0} during the epoxidation cannot be used profitably in many cases.

The invention solves the problem, propylene oxide or to produce other epoxides in a more economical way than before and at the same time the value of the main starting materials to maintain or increase su. l |

Daa erfindungigemä ·· Yerfsfcre * Rr leretelltmg vdtt Jeoxyiea ie *, characterized by the fact that Mn tin is an aralkyl hydroprotein and an oil content of an olefin compound containing a catalyst converts and the formed · Ipoxyd wins, whereby Molybdenum «· Vanadium and / or Wolfra» is used as a catalyst will. · I

909836/1487

BATH ORIGINAL

Preferred embodiments of the invention are described below Procedure described *

1. The hydroperoxide is made by reacting Xthylhensol with gaseous oxygen In the presence of an oxidation initiator manufactured; a compound having at least 3 carbon atoms is used as the olefin; that as By-product formed dL-fhenylethanol is obtained

2. The ethylbene sol that is not used is divided into the stage Hydroperoxydheretellun «swUokttfttfartf dft · Biobt usgtsetEte Propylene is used in the 8th stage of propylene oxide production surUok led.

3 · The ^ -phenylttthanol obtained as a by-product is dehydrated with styrene; the dehydration takes place in the vapor phase over a titanium dioxide catalyst at a fine temperature in the range of 180 - 28O ⁰ O «

4 "As a catalyst," int catalytically · quantity "of a Kolybdenummaleses an organic carboxylic acid (e.g. the haphthenate) or a catalytic amount of permolybdic acid · or Uolybdenum disulfide is used.

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BAD ORIOINAt

5. Me stage of Epoxydhorβteilung is carried out at a temperature ranging from -20 to +200 ⁰ C.

6, The A -phenylethanol is dehydrated and the formed Acetophenone is obtained "

7ο The cL 'phenylethanol is hydrogenated and the ethylbenzene formed is used to produce the ethylbenzene hydroperoxide «. · "

8. Bas Hydropeι oxide is duroh the formation of cumene aft prepared according to oxygen in the presence of an oxidation initiator; the olefin used has weplgetens as above 3. Carbon atoms} cumyl alcohol is obtained as a by-product.

.9 "The catalyst used here is a catalytic amount of a molybdenum as an oarboxylic acid (eg da · vaphthenate) λ or a catalytic amount of molybdenum acid β _# molybdenum» - the sulfide, vanadium naphthenate or tungsten carbonyl.

10c The cumyl alcohol is hydrogenated to cumene, which is then used for the Production of its hydroperoxide is used «

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BAD ORIGINAU

1518867

11. The Cumyla alcohol is converted into ^ .- methyletyrene.

Surprisingly, it was found daJ da * Hyroe * eacyd, that by oxidation of the above-mentioned alkylaro-tieohan Hydrocarbon borrows sugänglloh let, tin »excellent is a suitable agent for oxidizing propylene or analogous higher olefins. The new procedures mentioned above consists of a series of stages, dooh let it be not necessary, the one that occurs during the Umeetiung Separate intermediate products, so that the entire reaction sequence takes place in a particularly advantageous manner can be.

In the first stage of the process according to the invention, the aralkyhydrocarbon is oxidized with oxygen in the air, for example cumene or cumene hydroperoxide is oxidized. The) oxidation of the hydrocarbon "," .B. of cumene, can be carried out at degrees of conversion of blue 40% with high selectivity. Allphatiaohe HydroParoxides know that an O ₂ oxidation with a high degree of conversion and high selectivity is not obtained. The oxidation mixture obtained contains, in addition to the starting material, the hydroperoxide formed during the oxidation o In addition, it contains very small amounts of by-products. Me importation of propylene or one

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BATH ORIGINAL

equivalent higher olefins in this mixture (or in a concentrate thereof) at the same time as the addition of the catalyst or after the end of the addition of the catalyst leads to propylene oxide or the higher olefin oxide and, in the case of use, cumene hydroperoxide, results in the formation of cumyl alcohol.

Except for alcohol, it contains this as described above added a little acetophenone to the mixture of the reaction products. The propylene oxide passes easily through the mixture Separate distillation. . '

Ea can be twofold to introduce an inert solvent if the concentration of the hydroperoxide, for example of henylethylhydropoxyds or Oumolhydroperaxyds is greater than about 30-40 liters . The solvent used should be formed with the Peroxydsaueretoff or dttt in the implementation. the epoxy does not react. For example, as ( solution tert-butyl alcohol, dL-rhenylitbanol, umyl alcohol, benzene, toluene, ethylbenaol or umol) rerweaAtn.

The secondary alcohols can be dehydrated in a known manner to give ketones, e.g. and thus converted into marketable products. Instead one can use the alcohols, both the secondary ones as well as the tertiary alcohols readily known

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BATH ORIGINAL

Way dehydrate and thus in styrene or substituted Transfer styrenes, for which also sales opportunities exist. The former can be easily calibrated in a known manner Vacuum distillation obtained in a high degree of purity. Furthermore, the alcohol obtained therefrom or that from it leaves sioh obtained olefin, easily in known manner in the as Auegangasmaterial transfer used hydrocarbon, which is recycled, so that in this case the process without the formation of by-products is carried out. This consumes hydrogen *

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Di9 aralkyl hydroperoxides are particularly good oxidizing agents for the production of γοη epoxies. Compared with organic alkyl hydroperoxj d © £ _# s * B. those of isobutane, they are, among other things, several times more effective and, with reference to the peroxide, lead to better values and values, as shown in the following. YtrsuolMn gives "These V * - were, as generally described in the following Beiepislira, using 5 liters of the hydroperoxide, 5 g of the corresponding alcohols as a diluent, and 0.4 g of colybdenum naphthenate (Mo content 2 £) at 90 ^° C. (with the exception of the last isobutane experiment, which was carried out ^{at 150 ° C.)!}

909336 / U87

BATH ORIGINAL Hydroperoxide from

Duration of the peroxide Selek-C ₃ H ₆ fouling ^ change activity

Ethylbenzene (peroxide

90 $> pure) 13.9 g 0.5 hour «77.5 * 90

Cumene (90 56 pure)

14.7 .1.0

92.7

98

Isobutane (80 # pure) 16.1

Isobutane

15.7

49.5 83.9

75 96

49 ¥>

When using a Alkylhydroperoxyde, eB of tert · -Butylhydroperoxyd in tert-butanol and the selectivity falls in approximately linear relationship of about 89 to about 38 # from when the Percxydumwandlung is increased from about 30 to 96 i ". When using an aralkyl hydroperoxide, BB of ethylbenzene hydroperoxide in ethylbenzene or cumene hydroperoxide, on the other hand, the selectivity drops only slightly when the conversion is increased from 40-10 to about £ 98. Therefore, if the conversion is complete, good yields are achieved, so that the recovery and / or recycling of hydroperoxide is largely or completely avoided.

Furthermore, the mentioned aralkylcarbons can be oxidized to the hydro peroxides at a higher rate at higher degrees of conversion and with greater selectivity

as the alkyl compound *

909836/148 7

BAO ORIGINAL

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The following examples explain the invention without restricting it limit 'parts and prosentsets were eioh to the weight, if no other is given "

Examples 1 - 10

According to these examples, the spoxidation τοη propylene is carried out by adding the amount of peroxide given in the table below in g (sB QHP, Oomolhydroperoxy!), 5 g tB.A., tert-batyl alcohol or the specified solvent, the specified solvent to a pressure reactor The amount of molybdenum naphthenate or some other molybdenum salt »in g bit the specified Mo content in £ and the specified amount of propylene in g. The reaction is heated to the specified temperature in ⁰ C and stirred for the specified time without agitation at ordinary pressure. The results are also shown in the following table, in which the hydroperoxide conversion and selectivity, calculated from the molten propyleneoxy d, are given in moles per mole of converted hydroperoxides.

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BATH ORIGINAL

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909836 / U87

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BAD ORIGINAt

Example 11

The epoxidation of propylene is carried out essentially as described in Example 10, with the exception that the amount of catalyst is 0.9 g and the reaction time is 0.5 hours. The hydroperoxide conversion is 77 % and the selectivity is 94%, based on the propylene oxide formed in moles per mole of converted hydroperoxides.

Example 12 _4th

5 g 88 #iges dL Phenyläthylhydroperoxyd, 5 g of a.-phenylethanol, 0.6 g of molybdenum naphthenate (Mo content is 2 *) and 16.0 g of propylene are reacted for 15 minutes at 100 ⁰ C without stirring in eiiUtt Druokgefäas. The analysis results in a Peroxydumwandlung of 91 $> and the formation of Porpylenoxyd in a selectivity of 84 f'y based on consumed peroxide "The related propylene PropjJenoxydauabeute is 99 # 6 ^.

Example 13

The epoxidation is conducted as described in essentially as in Example 6, but Ci016 g are used as the catalyst permolybdic "The conversion is 92 # and the related peroxide selectivity 52 # _e

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BATH ORIGINAL

They use molybdenum as a catalyst in the process The procedure described above also leads to C * u good Results.

■ ο

Example U

The procedure described in Example 1 is wiedern ^ it ', but using 10 g of a solution of p-ethyltoluene in hydroperoxides Xthyltoluol, 16.8 g of propylene and 0.03 g Molybdänna ^ naphthenate bit a molybdenum content of 5 are used and temperature of 9O ⁰ C and a "Reaktlansdauer is applied for 30 minutes" you Hydrozyperoxyduonrandlung £ 75.5 and the selectivity 92 t, printed in Hol Fropylenozyds formed per mole ungesetsten hydroperoxides,

Example 15

They procedure described in Example 8 is repeated, but using 16.4 g of propylene, 0.08 g of Haphthenats, a temperature of 80 ⁰ C and a reaction time 1 hour yon "are used they Hydroperoxydumwandlung fi is 92.5 and the selectivity 83 #.

909836 / U87

Example 16

NaOH as described in Example 10 operation will be with 11 g of 63 #igen £ thylbenzolhydroperoxyda in Xthylbenzol, 29.6 g of methyl oleate, ₁₁ I O g molybdenum naphthenate having a molybdenum content of 5 $> _f a temperature of 80 ⁰ C and a Heaktionsdauer of 3 hours a Hydroperoxydumwandlung 83.8 $> and a selectivity of over 89 £ · auegedrückt achieved as Hol formed Methyloleatepoxyds per mole of unconverted Hydro "peroxide.

Example 17

According to the working wheat described in Example 16, 5.6 g of the hydroperoxide solution and 10.8 g of 4-vinyloyclohex ^ v at a temperature of 20 50 ⁰ C and a reaction time of 1 hour are a hydroperoxide conversion of 87 · 7 i> and about 100 Ige selectivity, expressed as 4 ~ vinyloyclohexene epoxide formed as per 1 mole of converted hydroperoxide achieved.

Coten-1, dodecene-1 and hexadecene-1 are used in the same way converted into their epoxies "

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Example 18

The procedure described in Example 17 gives 5 g of cumene hydroperoxide, 5 g of cumyl alcohol, 0.2 g of a catalyst solution which contains 3 * 4 ^ vanadium as naphthenate, and 15.4 g of propylene at a temperature of 90 ^° C. and one Reaction time of 3 hours, a hydroperoxide conversion of 68.2 # and a selectivity of 38 *.

In the procedure described above can also Tungsten carbonyl can be used as a catalyst *

The oxidation of armylic hydrocarbons, for example ethylbenzene or cumene, can be carried out in a known manner in such a way that the formation of the hydroperoxide is favored. Instead, the alcohol can be dehydrated to a styrene or in the group of secondary alcohols, acetophenone can be dehydrated in a known manner, both of which are valuable substances.

For example, oC phenylethanol (derived from the Hydroperoxide in a molar ratio of about 1: 1. is formed) in 80 ^ iger or higher yield by dehydration

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BAD OR) OINAL

In the gas phase at 200-250 ⁰ C for granular Titandioxy or a similar Oxydkatalysator at Atmosphärendruok in styrene converted »Additional catalysts suitable for this purpose, for example Bind Silioiumdioxyd or alumina. By distillation, styrene is obtained as a highly pure, marketable product,

After another procedure <L -Phenyläthanol at 200 - 300 ⁰ C in the presence of a copper catalyst to ^ acetophenone dehydrated and the ketone is obtained in a known manner and purified by distillation.

After a further procedure, the alcohol is converted in a known manner into the hydrocarbon used as the starting material , which is then returned to the process *

The temperatures which can be used in the epoxidation can vary widely depending on the reactivity and other characteristics of the other reactants. Temperaturtn in the range of about -20 ⁰ C to +200 ⁰ C, preferably 40-150 ⁰ C, especially from 60 «120 ⁰ O may be used. The conversion is carried out in a Druok, which is sufficient to maintain a liquid reaction phase. Although it is possible to work under reduced pressure, pressures in the range from about atmospheric pressure to 70 atü ('000 peig) are generally preferred »

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BATH ORIGINAL

1S18967

The catalyst is used in an amount which is at least sufficient to provide 0.01 mmoles of molybdenum or an equivalent catalytically active substance per mole of peroxide compound. 0.02-40 mmoles, in particular 0.1 to 4.0 mmoles, are preferably used. The molybdenum compounds that can be used include the organic molybdenum salts, the oxides, such as Mo ₂ O ₅ , MoO ₂ , MoO ₅ , molybdic acid, the molybdenum chlorides and oxychlorides, jiolybdenum fluoride, phosphate, sulfide and the like. Htteropoly acids containing molybdenum and their salts can also be used. Examples include phosphomolybdic acid and its sodium · - and Κβϋμπιββίζ ,.

The hydroperoxides used are obtained from alkyl aromatic hydrocarbons with at least one hydrogen atom on a carbon atom bonded to the ring. Acyl, φ carboxyl or esterified carboxyl groups may be substituted. can * The ring can have one or more side chains with up to 12 carbon atoms per chain. The chains can be branched = Examples are the hydroperoxides of toluene "ethylbenzene, cumene", p-ethyltoluene, leobutylbeneol, tetrahydranaphthalene ,. Diieopropylbenzene, p-propyltotuene, o-xylene, m-xylene, p-xylene and phenylcyolohexene called "The preferred hydroperoxides are those obtained from cumene and xethylbenzene. *

909836 / U87

For the practical implementation of the process according to the invention, catalytically active components can be used in the form of a compound or mixture which is initially soluble in the implementation medium Soluble substances suitable for purposes according to the invention, e.g. denote the carbon-soluble organometallic compounds with a solubility in methanol of at least 0.1 g / l at room temperature. Exemplary · soluble forms of the catalytically active substances are dl "Haphthenate, Stearale, Ootoate and carbonyls" Various chelates facility Runge connections and Enolsalze, such as the Acetoaoetonate can also apply ver ~ be · According to the invention ■ used · katalytisoh effective compounds of this type lind dl · Haphthenate and carbonyls of molybdenum, vanadium and tungsten.

The duration of the oxydation reaction depends on the usual conversion Applied for 10 hours and frequent sound for 5 minutes to 4 hours.

To the epoxydierbaaren by the method according to the invention

Unsaturated substances include substituted and 909836 / U87

BATH ORIGINAL

and non-substituted aliphatic and aliphatic olefins, which can be hydrocarbons, esters, alcohols, ketones or ethers and the like with generally about 2-30 carbon atoms, preferably at least 3 carbon atoms. Examples of olefins are ethylene, propylene, butylene, isobutylene, the pentenes, the methyl pentenes, the hexenes "the octenes _s öyclohexen the dodecenes, methyl cyclohexene, 1 * 3-butadiene ,, styrene, methyl styrene, vinyl toluene, vinyl cyclohexane and the biphenyl-cyclohexene, olefins having substituents containing for example, halogen, oxygen or sulfur , can also be used * Examples of such substituted olefins are allyl alcohol, allyl mercaptan, methallyl alcohol, cyclohexenols, diallyl ether, methyl methacrylate, methyl oleate, methyl vinyl ketone and allyl chloride. In general, all olefins which are converted into Bpoxides by processes known to date can be epoxidized according to the invention i

The lower olefinite would be a particular advantage 3 or 4 carbon atoms in an aliphatic chain epoxidized using the process according to the invention "

The ratio of olefins to organic peroxy compounds can vary within a wide range in the epoxidation reaction. In general, molar ratios of

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BATH

to

Olefin to Hyciroperoxyd in the range of 1 t 15 to 20 ti. Advantageously-1 »1 to 10 ί1 and in particular 2 ti to 5 ti applied

The concentration of hydroperoxide in the Epoxydierungsreaktionsgemiech is to begin implementing usually at 1 $> or above, but AUOH lower concentrations can be used with good effect.

The epoxidation can be carried out in the presence of a solvent and it is generally two-fold Solvent to use. In most cases, aqueous solvents are not considered. Suitable substances include hydrocarbons, and aliphatic, aromatic or aliphatic Naphthenic hydrocarbons and their oxygenated derivatives Alcohols, ketones, ethers and esters are particularly advantageous and the presence of alcoholic or ketonisohen * Subetanzen often has a beneficial effect even if the solvent mainly consists of coal consists. The use of Ettigsäurtlthyleeter, tert-butyl alcohol, Cumyl alcohol, L-phenyl ethanol and acetone are particularly favorable, and tert-butanol is a preventive solvent.

The dehydration catalyst * for the production of styrene can be used in a supported form or in granules or pellets. Typical carrier substances are

909836 / U87

ORiGiNAL INSPECTED

crushed sandstone, Silieiumdioxyd, filter stone and bound by ceramic method geschmolzeneβ alumina * For example, one can wet the carrier with water, then bring Titandioxydpulver in an amount of about 10 15 fo dos carrier and the catalyst and support to dry at 15O ⁰ C. The activity of the titanium dioxide can be increased by treatment with aqueous sulfuric acid (eg 10 %) and then washing with water to remove the acid before the titanium dioxide is applied to the carrier With a size of 4x6 mesh as a carrier, a production speed of 400 - 650 g styrene per liter of catalyst and hour can be achieved. Higher production speeds can be achieved with the titanium oxide catalyst in granular form, e.g. with a catalyst which is obtained as follows: chemically pure powdery anhydrous titanium oxide is wetted with water and the paste obtained is dried at 130-150 ° C, whereupon is powdered of dried · product and then pelletieiert. the pellets or granules are then fired in a furnace at a temperature of at least 800 ⁰ G, they woduroh a high mechanical strength gain ₀ then can a Aktivierungsetufe by immersing lh boiling aqueous nitric acid / concentration 18 - 20 $>) for about 90 minutes, washing with

909836 / U87

Subject verden 150 ⁰ C <> for this acid treatment may nan instead of nitric acid and hydrochloric acid "phosphoric acid or sulfuric use - water and drying at about 130th Between 800 and 1000 ⁰ O, the pellets shrink, making them harder and denser. These denser, harder pellets activate lassen.sich apparently by nitric acid not as leioht how fired at 800 ⁰ C, even if concentrated nitric acid used · You can, however, be activated by aqueous phosphoric acid with a concentration of 20 i ". Ba in the case of the denser, harder pellets dust formation of the catalyst, for example, is largely eliminated during the Besohickene, a grate temperature is preferably from about 1000 ⁰ C *

In general, the higher the production ratio, the higher the grain size is smaller. Grain sizes of less than 4.7 no (3/16 inch) largest dimensions are not well suited for mechanical reasons. Good production conditions are with Grains that measure up to 9 * 5 mm (3/8 inch) in one or more directions.

Favorable dehydration temperatures are "wipe 180 and 280 ⁰ C. It is usually necessary to temperatures below 220 ⁰ C, or

909836 / Utf

above 25O ⁰ O apply. At ⁰ C under 220 can be steam or vacuum applied "to the evaporation of the Oarbinole to promote" temperatures above about 250 ⁰ O bie to 280 ⁰ C can be used in conjunction with a high Celtic Beschickungegeechwlndlg.

Other methods of dehydration can, if desired, can also be used

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Claims (3)

1618967 p.atent entitlements 1. Process for the production of Epoxydtn, daduroh marked, that one is a mixture, the aralkyl hydroperoxide and a molybdenum, vanadium or tungsten compound as Contains catalyst, umsst with an olefin and the formed Bpoxyd win * 2. Method naoh claim 1, daduroh gekennseiohnet that aan a hydroperoxide is used, which tint by reaction of gaseous oxygen alt Xthylbensol in the presence · Oxidation initiator has been obtained by using tin Olefin having at least 3 carbon atoms is used and cL-phenylethanol wins as a vine product. 3. Procedure naoh Anspruoh 2, daduroh gekennstlohnet, dsj Bandst Unreacted ethylbene sol in the form of hydroxide formation eurUok leads.
I. 4 "Method according to claim 2, because you know that" an not absolutely propylene in the class of propylene oxide formation surttok leads. 909836 / U87 BATH ORIGINAL 5ο method naoh claim 2, characterized in that the ά-phenylethanol is dehydrated to styrene. 6ο method of claim 5 * characterized in that the dehydration in the gas phase above titanium dioxide as a catalyst at a temperature in the range of 180 - performs 28O ⁰ O. 7, method according to claim 2, characterized in that one is a molybdenum salt of a carboxylic acid, permolybdic acid or molybdenum sulphide used as a catalyst « Process according to claim 1, characterized in that the reaction is carried out at a temperature in the Bereloh of -20 ⁰ O to +200 ⁰ O, 9ο method naoh claim 2, characterized in that the cC-phenylethanol is dehydrated and the acetophenone formed is obtained. . 10οVerfahren according to claim 2, characterized in that one hydrogenated the «C-phenylethanol and the ethylbenzene formed used to form its hydroperoxide » 909836 / H87 11ο _r method according to claim 1, characterized in "that one of the Oxydationsinitiators prepared hydroperoxide and an olefin having 3 wenigstes Kohlenetoffatomen used by reacting with gaseous oxygen in the presence of cumene and cumyl alcohol ale lifting product wins * 12, method according to claim 11, characterized in that one a molybdenum salt of a carboxylic acid, ptrino Iy bd anic acid, MoIyV dandisulfide, vanadium naphthenate or wolfraaoarbonyl ala Catalyst used « 13 * Method according to claim 11, characterized in that the cumyl alcohol is converted into cumene and the latter is used to produce its hydroperoxide., U, process according to claim 11, characterized in that the cumyl alcohol is converted into <k ~ -methylstyrene. 909836 / U87