US2861031A - Process for the production of hydroperoxides of partially hydrogenated polycyclic aromatic hydrocarbons - Google Patents

Process for the production of hydroperoxides of partially hydrogenated polycyclic aromatic hydrocarbons Download PDF

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US2861031A
US2861031A US485598A US48559855A US2861031A US 2861031 A US2861031 A US 2861031A US 485598 A US485598 A US 485598A US 48559855 A US48559855 A US 48559855A US 2861031 A US2861031 A US 2861031A
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hydroperoxides
partially hydrogenated
aromatic hydrocarbons
tetrahydronaphthalene
oxidation
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US485598A
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Heise Rudolf
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Dehydag Deutsche Hydrierwerke GmbH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C409/00—Peroxy compounds
    • C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
    • C07C409/14—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom belonging to a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00—Preparation of peroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S204/00—Chemistry: electrical and wave energy
    • Y10S204/902—Production of desired compound by wave energy in presence of a chemically designated nonreactant chemical treating agent, excluding water, chloroform, carbon tetrachloride, methylene chloride or benzene
    • Y10S204/911—Nitrogen treating agent
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S204/00—Chemistry: electrical and wave energy
    • Y10S204/902—Production of desired compound by wave energy in presence of a chemically designated nonreactant chemical treating agent, excluding water, chloroform, carbon tetrachloride, methylene chloride or benzene
    • Y10S204/912—Oxygen treating agent

Definitions

  • This invention relates to a process for the production of hydroperoxides of partially hydrogenated polycyclic aromatic hydrocarbons, and more particularly to the oxidation of such aromatic hydrocarbons into the correspondmg hydroperoxides with the aid of an oxidizing gas, in the pi-(esence of fluorescent dyes, such as chlorophyll and the It has long been known that tetrahydronaphthalene tends to undergo an auto-oxidation reaction when it is brought into contact with oxygen or oxygen-containing gases.
  • the tetrahydronaphthalene takes up one mol of oxygen to form an oxidation product the structure of which has been ascertained to be 1,2,33,4- tetrahydronaphthalene-l-peroxide .(a-tetrahydronaphthalene peroxide).
  • the product which is essentially colorless, is however simultaneously discolored by this autooxidation and turns more or less yellow.
  • the prior art also discloses the use of suitable catalysts.
  • tetrahydronaphthalene peroxide itself is an effective catalyst.
  • certain metals and their compounds are effective catalysts; thus, it is known that the auto-oxidation of tetrahydronaphthalene intoits peroxide can be accelerated by the presence of copper, tin, lead, and the oxides and carbonates of these metallic elements, or by the presence of cobalt in the form of its naphthenates.
  • manganese stearate is a very effective catalyst.
  • Another object of the present invention is to provide a method of oxidizing partially hydrogenated polycyclic aromatic hydrocarbons into their hydroperoxides which will yield the desired product in a substantially pure form uncontaminated by undesirable dissociation and polymerization products.
  • Still another object of the present invention is to provide catalysts for the oxidation of partially hydrogenated iolycyclic aromatic hydrocarbons into the corresponding atom hydroperoxides which will produce higher yields of uncontaminated pure hydroperoxides.
  • Examples of partially hydrogenated polycyclic aromatic hydrocarbons which may be oxidized into the corresponding hydroperoxides by the method according to my invention are tetrahydropnaphthalene, octahydronaphthalene, benzene-alkyl-tetrahydronaphthalene, tetrahydroanthracene, octahydroanthracene, tetrahydropenanthrene, octahydrophenanthrene, tetrahydroacenaphthene, and the like.
  • the sensitizable organic dye is dissolved in the reaction mixture and uniformly distributed therethrough in a fluorescent state, whereby the quanta of light absorbed by the dye are released to every particle of the reaction mixture uniformly throughout the solution, producing a catalyzing photochemical eifect.
  • sensitizable organic dyes examples include chlorophyll, metal complex compounds such as the phthalocyanins, fluorescein, dinaphthylenedioxide, phenylbenzimidazole, phenyldlmethylacridine, and the like. Of these, however, chlorophyll has been found to be the most desirable catalyst because of its superior photochemical eflect.
  • the above-named fluorescent dyes, and particularly chlorophyll absorb primarily those quanta of light which have a relatively long wave length, i. e. those Which lie in the red and yellow range of the spectrum.
  • the most suitable sources of light which may be used for irradiating the reaction mixture in accordance with my invention are sunlight and incandescent light sources, both of which contain a large amount of red and yellow light quanta.
  • Electric incandescent light sources have the advantage that they simultaneously furnish some of the heat required for the oxidation reaction.
  • the transformation of partially hydrogenated polycyclic aromatic hydrocarbons into their corresponding hydroperoxides can also be accelerated by carrying out the oxidation in accordance with my invention at temperatures between 20 C. and 120 C., particularly between 60 C. and C.
  • the prevailing pressure may be either atmospheric pressure or an elevated pressure.
  • the process of oxidizing partially hydrogenated polycyclic aromatic hydrocarbons into their hydroperoxides has two distinct advantages over the processes heretofore known. First, the oxidation takes place within a much shorter time and produces much better yields than the known processes, and secondly, the short time required to reach a certain peroxide content practically eliminates undesirable side reactions, which tend to decoinpose the hydroperoxide formed and produce dark, tar-like dissociation products if the oxidation reaction requires an extended period of time.
  • the three tubes were then filled withtechnical grade tetrahydronaphthalene having a density of 0.968 at C. until the level of'liquid in the threetubes reached 50 cm. above the bottom. -A'finely divided, uniform stream of air, dried over concentrated sulfuric acid, was-then passedtlir'ou'gh' the"tetrahydronaphthalene in each tube" V L 'and'the temperature was adjusted to between 7 C. and
  • tube No. 2 the density at the end of 24 hours had increased to 0.996 at 20 C.', and in tube-No. 3 the photochemical oxidation had increased the density of the reaction mixture to 1.005 at 20 C.
  • peroxide which comprises passing air through tetrahydronaphthalene at a temperature from 70-75" C. in I the presence ofchlorophyll while exposing the reaction within of the amount of time.
  • yields produced by the uncatalyzed oxidation reaction after 24 hours are produced by the photochemical oxidation reaction after only 11-12 hours, i. e. in half the time.
  • the reaction product obtained by the process in accordance with 'the present invention is a solution of tetrahydronaphthalene peroxide in tetrahydronaphthalene.
  • the solution is practically free from dark, tar-like, decomposition or polymerization products;
  • the raw product may readily be purified by methods well known in the art to yield tetrahydronaphthalene peroxide of high purity. Both the raw and the purified'product are well suited as intermediate products in the' production of hydroaromatic alcohols, ketones and carbbxylic'acids; as
  • the intimate admixture of the tetrahydronaphthalene with the oxidizing gas is relatively important, for the etficient performance ofthe process according to my invention.
  • This intimate admixture can be brought about in a variety of ways.
  • the hydrocarbon may also be brought in intimate contact withv the gas in counter-current fashion, for example by trickling the hydrocarbon downwardly over Raschig rings or the like against aistream of rising,pre-
  • Still another method is to atomize the hydrocarbon into a mist or fog and then condeparting from the spirit of my invention or the .scope of the appended claims.
  • a light-sensitizable organic dye' selected from the group consisting of chlorophyll, phthalocyanins, fluorescein, dinaphthylenedioxide,'phenylbenzimidazole and phenyldimethylacridine,

Description

States Rudolf Heise, Dusseldorf-Holthausen, Germany, assignor to Dehydag, Deutsclie Hydrierwerke G. m. b. H., Dusseldorf, Germany, a corporation of Germany No Drawing. Application February 1, 1955 Serial No. 485,598
Claims priority, application Germany February 4, 1954 3 Claims. (Cl. 204-162) This invention relates to a process for the production of hydroperoxides of partially hydrogenated polycyclic aromatic hydrocarbons, and more particularly to the oxidation of such aromatic hydrocarbons into the correspondmg hydroperoxides with the aid of an oxidizing gas, in the pi-(esence of fluorescent dyes, such as chlorophyll and the It has long been known that tetrahydronaphthalene tends to undergo an auto-oxidation reaction when it is brought into contact with oxygen or oxygen-containing gases. In this reaction the tetrahydronaphthalene takes up one mol of oxygen to form an oxidation product the structure of which has been ascertained to be 1,2,33,4- tetrahydronaphthalene-l-peroxide .(a-tetrahydronaphthalene peroxide). The product, which is essentially colorless, is however simultaneously discolored by this autooxidation and turns more or less yellow.
It is also known that such an auto-oxidation reaction can be materially accelerated by passing the oxygen or oxygen-containing gas through the tetrahydronaphthalene in a finely divided form and maintaining the temperature of the reaction mixture above room temperature in order to increase the rate of oxidation.
As a further improvement of this auto-oxidation reaction, the prior art also discloses the use of suitable catalysts. For example, it is known that tetrahydronaphthalene peroxide itself is an effective catalyst. In addition, prior workers in this field have found that certain metals and their compounds are effective catalysts; thus, it is known that the auto-oxidation of tetrahydronaphthalene intoits peroxide can be accelerated by the presence of copper, tin, lead, and the oxides and carbonates of these metallic elements, or by the presence of cobalt in the form of its naphthenates. Within recent years it was also found that manganese stearate is a very effective catalyst.
While the above catalyst tends to accelerate the oxidation of partially hydrogenated polycyclic aromatic hydrocarbons into their hydroperoxides and produce improved yields, the methods employed by the prior art do not pro duce commercially attractive yields, and the oxidation products obtained by these methods are often discolored by undesirable dissociation products and polymerizates.
It is one object of the present invention to provide a method of oxidizing partially hydrogenated polycyclic aromatic hydrocarbons into their hydroperoxides which will produce commercially attractive yields of such hydroperoxides.
Another object of the present invention is to provide a method of oxidizing partially hydrogenated polycyclic aromatic hydrocarbons into their hydroperoxides which will yield the desired product in a substantially pure form uncontaminated by undesirable dissociation and polymerization products.
Still another object of the present invention is to provide catalysts for the oxidation of partially hydrogenated iolycyclic aromatic hydrocarbons into the corresponding atom hydroperoxides which will produce higher yields of uncontaminated pure hydroperoxides.
Other objects and advantages of this invention will become apparent as the description thereof proceeds.
I have found that the transformation of partially hydrogenated polycyclic aromatic hydrocarbons into their corresponding hydroperoxides can be carried out much more rapidly and with much improved yields over the methods of the prior art, by oxidizing such hydrocarbons with oxygen or oxygen-containing gases in the presence of sensitizable organic dyes, i. e. organic dyes which absorb certain portions of the spectrum, and while exposing the reaction mixture, including said organic dye, to light. The reaction according to my invention is preferably carried out at elevated temperatures and at atmospheric or elevated pressure.
Examples of partially hydrogenated polycyclic aromatic hydrocarbons Which may be oxidized into the corresponding hydroperoxides by the method according to my invention are tetrahydropnaphthalene, octahydronaphthalene, benzene-alkyl-tetrahydronaphthalene, tetrahydroanthracene, octahydroanthracene, tetrahydropenanthrene, octahydrophenanthrene, tetrahydroacenaphthene, and the like.
The sensitizable organic dye is dissolved in the reaction mixture and uniformly distributed therethrough in a fluorescent state, whereby the quanta of light absorbed by the dye are released to every particle of the reaction mixture uniformly throughout the solution, producing a catalyzing photochemical eifect.
Examples of suitable sensitizable organic dyes are chlorophyll, metal complex compounds such as the phthalocyanins, fluorescein, dinaphthylenedioxide, phenylbenzimidazole, phenyldlmethylacridine, and the like. Of these, however, chlorophyll has been found to be the most desirable catalyst because of its superior photochemical eflect.
The above-named fluorescent dyes, and particularly chlorophyll, absorb primarily those quanta of light which have a relatively long wave length, i. e. those Which lie in the red and yellow range of the spectrum. Hence, the most suitable sources of light which may be used for irradiating the reaction mixture in accordance with my invention are sunlight and incandescent light sources, both of which contain a large amount of red and yellow light quanta. Electric incandescent light sources have the advantage that they simultaneously furnish some of the heat required for the oxidation reaction.
The transformation of partially hydrogenated polycyclic aromatic hydrocarbons into their corresponding hydroperoxides can also be accelerated by carrying out the oxidation in accordance with my invention at temperatures between 20 C. and 120 C., particularly between 60 C. and C. The prevailing pressure may be either atmospheric pressure or an elevated pressure.
The process of oxidizing partially hydrogenated polycyclic aromatic hydrocarbons into their hydroperoxides according to my invention has two distinct advantages over the processes heretofore known. First, the oxidation takes place within a much shorter time and produces much better yields than the known processes, and secondly, the short time required to reach a certain peroxide content practically eliminates undesirable side reactions, which tend to decoinpose the hydroperoxide formed and produce dark, tar-like dissociation products if the oxidation reaction requires an extended period of time.
The following example will further illustrate my invention and enable others skilled in the art to understand my invention more completely. It is understood, however, that the present invention is not limited to the example.
Example Three identical glass tubes, each having an internal volume of 650 c c., were closed ofi at one end with sin- 'tered glass or ceramic fritl The other end of each tube was provided with a spherical enlargement to -receive the foam' formed during the oxidation reaction. I Each tube was also'providedwith a water jacket'to maintain the temperature substantially constant during the reaction.
The three tubes were then filled withtechnical grade tetrahydronaphthalene having a density of 0.968 at C. until the level of'liquid in the threetubes reached 50 cm. above the bottom. -A'finely divided, uniform stream of air, dried over concentrated sulfuric acid, was-then passedtlir'ou'gh' the"tetrahydronaphthalene in each tube" V L 'and'the temperature was adjusted to between 7 C. and
The 'oxidationof tetrahydronaphthalene in tube No. 1
was permittedto proceed in the absence of any catalyst whatsoever. To the reaction mixture in tube No.,2,'0.1% by weight of manganeSeJstearate based on theweight of tetrahydronaphthalene was added. The reaction mixture in tube No. 3 was modified by the addition 050.1% by 'weight .ofroil-soluble, copper-free chlorophyll and the tube'was exposed to light which was rich in red and yellow light quanta. 1 J
The progress of theioxidation in each of,the three tubes was followed by determining the peroxide content by iodometrictitration and periodic measurement of the density of thereaction mixture. I
The period of observation extended over 24 hours since it is known that during that period the density and the peroxide content increase uniformly and steadily,
whereas if the reaction is allowed to continue over a longer period of time the density of the reaction mixture .continues to increase while the peroxide content, after having reached a certain maximum value, begins to decrease due to decomposition reactions Since the oxidation reactions in the three tubes were carried out under identical conditions except with respect to the presence of a catalyst and the exposure to light in the case of tube No. 3, an excellent basis for comparison was given. Such a comparison confirmed the known fact that the oxidation of tetrahydronaphthalene into its peroxides in the presence of manganese stearate as a .catalyst proceeds much more rapidly than the oxidation in the absence of a catalyst. In addition, the comparison of the periodic measurements of density and peroxide content surprisingly showed that the photochemical oxida- .tion in the presence of chlorophyll while exposing the reaction mixture to light proceeds much more rapidly than the oxidation in the presence of manganese stearate.
. In other words, the oxidation in tube No.' 3 produced considerably higher yields of tetrahydronaphthalene .peroxide in the same period of time.
More particularly, the following data were obtained: The density of the reaction mixture in tube No. 1 at the end of 24 hours had increased from 0.968 at 20 C.
to 0.987 at 20 C. In tube No. 2 the density at the end of 24 hours had increased to 0.996 at 20 C.', and in tube-No. 3 the photochemical oxidation had increased the density of the reaction mixture to 1.005 at 20 C. Similarly, the content of tetrahydronaphthalene peroxide in tube Nol 1 at the end of 24 hours was 17% and in tube No. 2 it was 27%; in tube No. 3 itwas 37%.
Comparison of the periodic measurements of density and peroxide content in the three tubes respectively showed that the yields produced by the oxidation reaction catalyzed by manganese stearate after 24 hours, are
produced by'the photochemical reaction in accordance with the present invention after only 15 to 16 hours, i. e.
tacting' it in that form with the oxidizing gas.
While. I have. disclosed certain specific embodiments of myinventiomfI wish it to. be understood that various changes and modifications can be made therein without.
peroxide, which comprises passing air through tetrahydronaphthalene at a temperature from 70-75" C. in I the presence ofchlorophyll while exposing the reaction within of the amount of time. Similarly, the yields produced by the uncatalyzed oxidation reaction after 24 hours, are produced by the photochemical oxidation reaction after only 11-12 hours, i. e. in half the time.
The reaction product obtained by the process in accordance with 'the present invention is a solution of tetrahydronaphthalene peroxide in tetrahydronaphthalene. The solution is practically free from dark, tar-like, decomposition or polymerization products; The raw product may readily be purified by methods well known in the art to yield tetrahydronaphthalene peroxide of high purity. Both the raw and the purified'product are well suited as intermediate products in the' production of hydroaromatic alcohols, ketones and carbbxylic'acids; as
initiators for polymerization processes, as oxidizing and bleaching agents, and for many other industrial purposes. The intimate admixture of the tetrahydronaphthalene with the oxidizing gas is relatively important, for the etficient performance ofthe process according to my invention. This intimate admixture can be brought about in a variety of ways. In addition to introducing the oxygen or oxygen-containing gas in a finely divided state into the partially hydrogenated polycyclic aromatic hydrocarbon, the hydrocarbon may also be brought in intimate contact withv the gas in counter-current fashion, for example by trickling the hydrocarbon downwardly over Raschig rings or the like against aistream of rising,pre-
heated oxidizing gases. Still another method is to atomize the hydrocarbon into a mist or fog and then condeparting from the spirit of my invention or the .scope of the appended claims.
According to the procedure of the above-mentidned example, other partially hydrogenated polycyclic aromatic hydrocarbons may be oxidized, such as octahydr'onaphthalene, benzene-alkyl-tetrahydronaphthalenes, ara'lkyltetrahydronaphthalenes, tetrahydroanthracene and: trahydrophenanthrene. I] claimz 1. The method of tially hydrogenated naphthalene derivatives, whichpomprises passing an oxygen-containing gas through apartially hydrogenated naphthalene at a temperature between 20 and C. in ,the presence of a light-sensitizable organic dye' selected from the group consisting of chlorophyll, phthalocyanins, fluorescein, dinaphthylenedioxide,'phenylbenzimidazole and phenyldimethylacridine,
while exposing the reaction mixture to light.
2.The method of producing 'tetrahydronapthal'ene mixture to light.
3. The method of producing tetrahydronaphthalene peroxide as'in claim 2, wherein the light to which the reaction mixture is exposed is rich in red and yellow light quanta. r I
References Cited in the file of this patent UNITED STATES PATENTS 2,165,130 2,435,763 Vaughan et al. Feb; 10,1948 2,543,817 Weil Mar. 6,19511 2,727,857 Carter Dec. 20, 1955 producing hydroperoxides ofipafr- A July 4. 1939'

Claims (1)

1. THE METHOD OF PRODUCING HYDROPEROXIDES OF PARTIALLY HYDROGENATED NAPHTHALENE DERIVATIVES, WHICH COMPRISES PASSING AN OXYGEN-CONTAINING GAS THROUGH A PARTIALLY HYDROGENATED NAPHTHALENE AT A TEMPERATURE BETWEEN 20 AND 120*C. IN THE PRESENCE OF A LIGHT-SENSITIZABLE ORGANIC DYE SELECTED FROM THE GROUP CONSISTING OF CHLOROPHYLL, PHTHALOCYANINS, FLUORESCEIN, DINAPHTHYLENEDIOXIDE, PHENYLBENZIMIDAZOLE AND PHENYLDIMETHYLACRIDINE, WHILE EXPOSING THE REACTION MIXTURE TO LIGHT.
US485598A 1954-02-04 1955-02-01 Process for the production of hydroperoxides of partially hydrogenated polycyclic aromatic hydrocarbons Expired - Lifetime US2861031A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3663393A (en) * 1968-09-03 1972-05-16 Fmc Corp Irradiation method of preparing aralkyl hydroperoxides from hydrocarbons

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2899463A (en) * 1959-08-11 Preparation of oxygenated resin acid
BE535707A (en) * 1954-02-17
US2996515A (en) * 1957-04-16 1961-08-15 Richard N Moore Method for producing photoperoxides

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2165130A (en) * 1939-07-04 Increasing the bkzjng psmjpeitties
US2435763A (en) * 1944-03-13 1948-02-10 Shell Dev Hydrogen bromide catalyzed oxidation reactions
US2543817A (en) * 1948-07-02 1951-03-06 Weil Leopold Photochemical oxidation of nicotine
US2727857A (en) * 1951-10-25 1955-12-20 Procter & Gamble Preparation of fatty peroxides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2165130A (en) * 1939-07-04 Increasing the bkzjng psmjpeitties
US2435763A (en) * 1944-03-13 1948-02-10 Shell Dev Hydrogen bromide catalyzed oxidation reactions
US2543817A (en) * 1948-07-02 1951-03-06 Weil Leopold Photochemical oxidation of nicotine
US2727857A (en) * 1951-10-25 1955-12-20 Procter & Gamble Preparation of fatty peroxides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3663393A (en) * 1968-09-03 1972-05-16 Fmc Corp Irradiation method of preparing aralkyl hydroperoxides from hydrocarbons

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GB777501A (en) 1957-06-26

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