DE945506C - Verfahren zur Herstellung von Hydroperoxyden durch katalytische Oxydation von alkylaromatischen Kohlenwasserstoffen - Google Patents
Verfahren zur Herstellung von Hydroperoxyden durch katalytische Oxydation von alkylaromatischen KohlenwasserstoffenInfo
- Publication number
- DE945506C DE945506C DES27026A DES0027026A DE945506C DE 945506 C DE945506 C DE 945506C DE S27026 A DES27026 A DE S27026A DE S0027026 A DES0027026 A DE S0027026A DE 945506 C DE945506 C DE 945506C
- Authority
- DE
- Germany
- Prior art keywords
- formate
- hydroperoxide
- hydroperoxides
- hours
- production
- 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
- 230000003647 oxidation Effects 0.000 title claims description 11
- 238000007254 oxidation reaction Methods 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 8
- 150000002432 hydroperoxides Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- -1 alkyl aromatic hydrocarbons Chemical class 0.000 title claims description 3
- 230000003197 catalytic effect Effects 0.000 title claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 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 claims description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 150000003891 oxalate salts Chemical class 0.000 claims description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 22
- 229940044170 formate Drugs 0.000 description 22
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 18
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 17
- 239000004280 Sodium formate Substances 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 9
- 235000019254 sodium formate Nutrition 0.000 description 9
- 239000000047 product Substances 0.000 description 6
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
- CBOCVOKPQGJKKJ-UHFFFAOYSA-L Calcium formate Chemical compound [Ca+2].[O-]C=O.[O-]C=O CBOCVOKPQGJKKJ-UHFFFAOYSA-L 0.000 description 2
- 229940044172 calcium formate Drugs 0.000 description 2
- 235000019255 calcium formate Nutrition 0.000 description 2
- 239000004281 calcium formate Substances 0.000 description 2
- QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 description 2
- 210000004124 hock Anatomy 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
- 235000010234 sodium benzoate Nutrition 0.000 description 2
- 239000004299 sodium benzoate Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 2
- 229940039790 sodium oxalate Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BANZVKGLDQDFDV-UHFFFAOYSA-N 2-propan-2-ylbenzoic acid Chemical group CC(C)C1=CC=CC=C1C(O)=O BANZVKGLDQDFDV-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- XLPDVYGDNRIQFV-UHFFFAOYSA-N p-Cymen-8-ol Chemical compound CC1=CC=C(C(C)(C)O)C=C1 XLPDVYGDNRIQFV-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR280451X | 1951-04-28 | ||
| FR30851X | 1951-08-03 | ||
| FR103201T | 1951-08-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE945506C true DE945506C (de) | 1956-07-12 |
Family
ID=27244973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES27026A Expired DE945506C (de) | 1951-04-28 | 1952-02-02 | Verfahren zur Herstellung von Hydroperoxyden durch katalytische Oxydation von alkylaromatischen Kohlenwasserstoffen |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US2681937A (enrdf_load_stackoverflow) |
| BE (1) | BE508321A (enrdf_load_stackoverflow) |
| CH (2) | CH280451A (enrdf_load_stackoverflow) |
| DE (1) | DE945506C (enrdf_load_stackoverflow) |
| FR (1) | FR1032010A (enrdf_load_stackoverflow) |
| GB (1) | GB711392A (enrdf_load_stackoverflow) |
| LU (1) | LU31162A1 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1156411B (de) * | 1960-01-11 | 1963-10-31 | It Resine Soc | Verfahren zur Herstellung von Cumolhydroperoxyd |
Families Citing this family (6)
| 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 |
| DE1081235B (de) * | 1954-12-14 | 1960-05-05 | Polymer Corp | Verfahren zur Polymerisation und Mischpolymerisation von konjugierten Diolefinen |
| LU37885A1 (enrdf_load_stackoverflow) * | 1958-12-17 | |||
| DE1134376B (de) * | 1960-04-05 | 1962-08-09 | Phenolchemie Ges Mit Beschraen | Verfahren zur Anreicherung von tertiaeren Aralkylmonohydroperoxyden in Kohlenwasserstoffloesungen |
| US4262143A (en) * | 1979-02-16 | 1981-04-14 | Halcon International, Inc. | Preparation of hydroperoxides |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB610293A (en) * | 1946-04-08 | 1948-10-13 | Distillers Co Yeast Ltd | Improvements in or relating to the manufacture of alkyl benzene peroxides |
| GB646102A (en) * | 1948-05-19 | 1950-11-15 | Distillers Co Yeast Ltd | Manufacture of organic oxidation products |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
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/fr unknown
-
1951
- 1951-02-02 FR FR103201D patent/FR1032010A/fr 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/fr unknown
- 1952-02-02 DE DES27026A patent/DE945506C/de not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB610293A (en) * | 1946-04-08 | 1948-10-13 | Distillers Co Yeast Ltd | Improvements in or relating to the manufacture of alkyl benzene peroxides |
| GB646102A (en) * | 1948-05-19 | 1950-11-15 | Distillers Co Yeast Ltd | Manufacture of organic oxidation products |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1156411B (de) * | 1960-01-11 | 1963-10-31 | It Resine Soc | Verfahren zur Herstellung von Cumolhydroperoxyd |
Also Published As
| Publication number | Publication date |
|---|---|
| CH295995A (fr) | 1954-01-31 |
| USRE24036E (en) | 1955-07-12 |
| FR1032010A (fr) | 1953-06-29 |
| CH280451A (fr) | 1952-01-31 |
| GB711392A (en) | 1954-06-30 |
| US2681937A (en) | 1954-06-22 |
| BE508321A (enrdf_load_stackoverflow) | |
| LU31162A1 (enrdf_load_stackoverflow) |
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