GB711392A - Improvements in or relating to the production of the hydroperoxides of cumene and other alkyl-aromatic hydrocarbons - Google Patents
Improvements in or relating to the production of the hydroperoxides of cumene and other alkyl-aromatic hydrocarbonsInfo
- Publication number
- GB711392A GB711392A GB1456/52A GB145652A GB711392A GB 711392 A GB711392 A GB 711392A GB 1456/52 A GB1456/52 A GB 1456/52A GB 145652 A GB145652 A GB 145652A GB 711392 A GB711392 A GB 711392A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sodium
- oxygen
- cumene
- hydroperoxides
- oxalate
- 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
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 title abstract 8
- 150000002432 hydroperoxides Chemical class 0.000 title abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 5
- 239000001301 oxygen Substances 0.000 abstract 5
- 229910052760 oxygen Inorganic materials 0.000 abstract 5
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 abstract 4
- CBOCVOKPQGJKKJ-UHFFFAOYSA-L Calcium formate Chemical compound [Ca+2].[O-]C=O.[O-]C=O CBOCVOKPQGJKKJ-UHFFFAOYSA-L 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 2
- 239000004280 Sodium formate Substances 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 229940044172 calcium formate Drugs 0.000 abstract 2
- 235000019255 calcium formate Nutrition 0.000 abstract 2
- 239000004281 calcium formate Substances 0.000 abstract 2
- QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 abstract 2
- 239000007789 gas Substances 0.000 abstract 2
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 abstract 2
- 235000010234 sodium benzoate Nutrition 0.000 abstract 2
- 239000004299 sodium benzoate Substances 0.000 abstract 2
- 235000019254 sodium formate Nutrition 0.000 abstract 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 abstract 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- -1 alkyl aromatic hydrocarbons Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229940050390 benzoate Drugs 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 229940044170 formate Drugs 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229940039748 oxalate Drugs 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 235000015424 sodium Nutrition 0.000 abstract 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 abstract 1
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 abstract 1
- 229940039790 sodium oxalate Drugs 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A42—HEADWEAR
- A42C—MANUFACTURING OR TRIMMING HEAD COVERINGS, e.g. HATS
- A42C1/00—Manufacturing hats
- A42C1/02—Making hat-bats; Bat-forming machines; Conical bat machines; Bat-forming tools
-
- 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
- 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
- C07C409/04—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 being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
-
- 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
- C07C409/04—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 being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
- C07C409/10—Cumene hydroperoxide
-
- 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
- C07C409/04—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 being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
- C07C409/12—Compounds containing six-membered aromatic rings with two alpha,alpha-dialkylmethyl hydroperoxy groups bound to carbon atoms of the same six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Hydroperoxides of cumene and other alkyl aromatic hydrocarbons containing a tertiary alkyl group are prepared by oxidizing the hydrocarbon with oxygen or an oxygen containing gas in the presence of the formate, oxalate or benzoate of an alkali or alkaline earth metal as a catalyst. Preferably cumene, p-cymene, diisopropyl benzene or isobutyl benzene is oxidized at an elevated temperature by means of oxygen or an oxygen-containing gas in the presence of, for example, sodium or calcium formate, sodium or calcium oxalate or sodium benzoate and in the presence of a hydroperoxide suitably a small quantity of the hydroperoxide, which forms the reaction product, to initiate the reaction. In examples, cumene, p-cymene and isobutyl benzene are oxidized to the corresponding hydroperoxides by air or oxygen in the presence of sodium formate, calcium formate, sodium oxalate, calcium oxalate or sodium benzoate. Specification 610,293 is referred to.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR280451X | 1951-04-28 | ||
| FR103201T | 1951-08-03 | ||
| FR30851X | 1951-08-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB711392A true GB711392A (en) | 1954-06-30 |
Family
ID=27244973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1456/52A Expired GB711392A (en) | 1951-04-28 | 1952-01-18 | Improvements in or relating to the production of the hydroperoxides of cumene and other alkyl-aromatic hydrocarbons |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US2681937A (en) |
| BE (1) | BE508321A (en) |
| CH (2) | CH280451A (en) |
| DE (1) | DE945506C (en) |
| FR (1) | FR1032010A (en) |
| GB (1) | GB711392A (en) |
| LU (1) | LU31162A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1081235B (en) * | 1954-12-14 | 1960-05-05 | Polymer Corp | Process for the polymerization and interpolymerization of conjugated diolefins |
| DE1134376B (en) * | 1960-04-05 | 1962-08-09 | Phenolchemie Ges Mit Beschraen | Process for the enrichment of tertiary aralkyl monohydroperoxides in hydrocarbon solutions |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB758934A (en) * | 1953-10-12 | 1956-10-10 | Ici Ltd | Improvements in and relating to the oxidation of aromatic hydrocarbons |
| US2820832A (en) * | 1954-06-18 | 1958-01-21 | Ici Ltd | Production of hydroperoxides |
| NL107808C (en) * | 1958-12-17 | |||
| DE1156411B (en) * | 1960-01-11 | 1963-10-31 | It Resine Soc | Process for the production of cumene hydroperoxide |
| US4262143A (en) * | 1979-02-16 | 1981-04-14 | Halcon International, Inc. | Preparation of hydroperoxides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE472342A (en) * | 1946-04-08 | |||
| US2547938A (en) * | 1946-04-08 | 1951-04-10 | Hercules Powder Co Ltd | Manufacture of alkyl benzene peroxides |
| US2548435A (en) * | 1946-08-01 | 1951-04-10 | Hercules Powder Co Ltd | Oxidation of aromatic hydrocarbons |
| GB646102A (en) * | 1948-05-19 | 1950-11-15 | Distillers Co Yeast Ltd | Manufacture of organic oxidation products |
-
0
- US US24036D patent/USRE24036E/en not_active Expired
- BE BE508321D patent/BE508321A/xx unknown
- LU LU31162D patent/LU31162A1/xx unknown
-
1949
- 1949-11-30 CH CH280451D patent/CH280451A/en unknown
-
1951
- 1951-02-02 FR FR103201D patent/FR1032010A/en not_active Expired
-
1952
- 1952-01-18 GB GB1456/52A patent/GB711392A/en not_active Expired
- 1952-01-28 US US268682A patent/US2681937A/en not_active Expired - Lifetime
- 1952-01-30 CH CH295995D patent/CH295995A/en unknown
- 1952-02-02 DE DES27026A patent/DE945506C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1081235B (en) * | 1954-12-14 | 1960-05-05 | Polymer Corp | Process for the polymerization and interpolymerization of conjugated diolefins |
| DE1134376B (en) * | 1960-04-05 | 1962-08-09 | Phenolchemie Ges Mit Beschraen | Process for the enrichment of tertiary aralkyl monohydroperoxides in hydrocarbon solutions |
Also Published As
| Publication number | Publication date |
|---|---|
| DE945506C (en) | 1956-07-12 |
| CH295995A (en) | 1954-01-31 |
| CH280451A (en) | 1952-01-31 |
| FR1032010A (en) | 1953-06-29 |
| US2681937A (en) | 1954-06-22 |
| BE508321A (en) | |
| LU31162A1 (en) | |
| USRE24036E (en) | 1955-07-12 |
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| Publication | Publication Date | Title |
|---|---|---|
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