GB777501A - Process for the production of hydroperoxides of partly-hydrogenated polynuclear, aromatic hydrocarbons - Google Patents
Process for the production of hydroperoxides of partly-hydrogenated polynuclear, aromatic hydrocarbonsInfo
- Publication number
- GB777501A GB777501A GB2921/55A GB292155A GB777501A GB 777501 A GB777501 A GB 777501A GB 2921/55 A GB2921/55 A GB 2921/55A GB 292155 A GB292155 A GB 292155A GB 777501 A GB777501 A GB 777501A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxidation
- light
- tetrahydronaphthalene
- oxidizing gas
- hydrocarbon
- 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title abstract 2
- 150000002432 hydroperoxides Chemical class 0.000 title abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 5
- 150000002430 hydrocarbons Chemical class 0.000 abstract 5
- 239000007789 gas Substances 0.000 abstract 4
- 230000003647 oxidation Effects 0.000 abstract 4
- 238000007254 oxidation reaction Methods 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 230000001590 oxidative effect Effects 0.000 abstract 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229930002875 chlorophyll Natural products 0.000 abstract 2
- 235000019804 chlorophyll Nutrition 0.000 abstract 2
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical class C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 abstract 2
- 238000004040 coloring Methods 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 238000001953 recrystallisation Methods 0.000 abstract 2
- BDAGIAXQQBRORQ-UHFFFAOYSA-N 1,2,3,3a,4,5-hexahydroacenaphthylene Chemical compound C1CCC2CCC3=CC=CC1=C32 BDAGIAXQQBRORQ-UHFFFAOYSA-N 0.000 abstract 1
- PJDWNSYGMXODTB-UHFFFAOYSA-N 1,2,3,4,4a,4b,5,6-octahydrophenanthrene Chemical compound C1=CCCC2C(CCCC3)C3=CC=C21 PJDWNSYGMXODTB-UHFFFAOYSA-N 0.000 abstract 1
- VTIBBOHXBURHMD-UHFFFAOYSA-N 1,2,3,4,4a,5,10,10a-octahydroanthracene Chemical compound C1=CCC2CC(CCCC3)C3=CC2=C1 VTIBBOHXBURHMD-UHFFFAOYSA-N 0.000 abstract 1
- POPHMOPNVVKGRW-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7-octahydronaphthalene Chemical compound C1CCC2CCCCC2=C1 POPHMOPNVVKGRW-UHFFFAOYSA-N 0.000 abstract 1
- PUNXVEAWLAVABA-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene;1,2,5,6-tetrahydroanthracene Chemical compound C1=CC=C2C=C(CCCC3)C3=CC2=C1.C1=CCCC2=C1C=C1CCC=CC1=C2 PUNXVEAWLAVABA-UHFFFAOYSA-N 0.000 abstract 1
- UXNCDAQNSQBHEN-UHFFFAOYSA-N 1,2,3,4-tetrahydrophenanthrene Chemical compound C1=CC2=CC=CC=C2C2=C1CCCC2 UXNCDAQNSQBHEN-UHFFFAOYSA-N 0.000 abstract 1
- DWYHDSLIWMUSOO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N1 DWYHDSLIWMUSOO-UHFFFAOYSA-N 0.000 abstract 1
- OYPIMRRBVHIMLW-UHFFFAOYSA-N 9-phenyl-2,3,4,5,6,7,9,10-octahydroacridine-1,8-dione Chemical compound O=C1CCCC(NC2=C3C(CCC2)=O)=C1C3C1=CC=CC=C1 OYPIMRRBVHIMLW-UHFFFAOYSA-N 0.000 abstract 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 abstract 1
- AMDQVKPUZIXQFC-UHFFFAOYSA-N dinaphthylene dioxide Chemical compound O1C(C2=C34)=CC=CC2=CC=C3OC2=CC=CC3=CC=C1C4=C32 AMDQVKPUZIXQFC-UHFFFAOYSA-N 0.000 abstract 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- SZINCDDYCOIOJQ-UHFFFAOYSA-L manganese(2+);octadecanoate Chemical compound [Mn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O SZINCDDYCOIOJQ-UHFFFAOYSA-L 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Chemical class 0.000 abstract 1
- 229910052573 porcelain Inorganic materials 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 239000008262 pumice Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- 230000003595 spectral effect Effects 0.000 abstract 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Hydroperoxides of partly - hydrogenated, polynuclear, aromatic hydrocarbons are prepared by oxidation of the hydrocarbons in the liquid phase with oxygen or oxygen-containing gases at raised temperatures and normal or increased pressures under exposure to light and in the presence of an organic colouring matter which absorbs light in the red to yellow spectral range, and separating the resulting hydroperoxide in known manner from the reaction mixture. Hydrocarbons which may be oxidized are tetrahydronaphthalene, octahydronaphthalene, ar-alkyl-tetrahydronaphthalenes, tetrahydroanthracene, octahydroanthracene, tetrahydrophenanthrene, octahydrophenanthrene, and tetrahydroacenaphthene. Organic colouring matters specified are chlorophyll, metal complexes of phthalocyanines, fluorescein, dinaphthylene dioxide (2:81; 8:21 - dioxidodinaph-thyl - 1:11), 2 - phenyl - benzimidazole and 9-phenyl - 3:7 - dimethylacridine. Both sunlight and artificial light may be used. The oxidation may be conducted by passing the oxidizing gas in a finely divided state through the hydrocarbon at reaction temperature, by trickling the hydrocarbon over Raschig or porcelain rings or pumice in countercurrent to the heated oxidizing gas, or the hydrocarbon may be sprayed or atomized and contacted with the oxidizing gas. The hydroperoxide is isolated by precipitation of its salt with caustic soda solution, liberation of the free hydroperoxide by treatment with acetic acid and recrystallization from ether, or by distilling off the unreacted tetrahydronaphthalene in vacuo and recrystallization. In an example, the oxidation of tetrahydronaphthalene in the presence of chlorophyll and light is compared with a similar but uncatalysed reaction, and a similar oxidation catalysed by manganese stearate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE777501X | 1954-02-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB777501A true GB777501A (en) | 1957-06-26 |
Family
ID=6686769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2921/55A Expired GB777501A (en) | 1954-02-04 | 1955-02-01 | Process for the production of hydroperoxides of partly-hydrogenated polynuclear, aromatic hydrocarbons |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2861031A (en) |
| FR (1) | FR1118040A (en) |
| GB (1) | GB777501A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2996515A (en) * | 1957-04-16 | 1961-08-15 | Richard N Moore | Method for producing photoperoxides |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2899463A (en) * | 1959-08-11 | Preparation of oxygenated resin acid | ||
| BE535707A (en) * | 1954-02-17 | |||
| US3663393A (en) * | 1968-09-03 | 1972-05-16 | Fmc Corp | Irradiation method of preparing aralkyl hydroperoxides from hydrocarbons |
Family Cites Families (4)
| 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 |
-
1955
- 1955-01-21 FR FR1118040D patent/FR1118040A/en not_active Expired
- 1955-02-01 GB GB2921/55A patent/GB777501A/en not_active Expired
- 1955-02-01 US US485598A patent/US2861031A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2996515A (en) * | 1957-04-16 | 1961-08-15 | Richard N Moore | Method for producing photoperoxides |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1118040A (en) | 1956-05-30 |
| US2861031A (en) | 1958-11-18 |
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