GB641250A - Process for the manufacture of di-isopropyl-benzene hydro-peroxides and products resulting therefrom - Google Patents
Process for the manufacture of di-isopropyl-benzene hydro-peroxides and products resulting therefromInfo
- Publication number
- GB641250A GB641250A GB1711847A GB1711847A GB641250A GB 641250 A GB641250 A GB 641250A GB 1711847 A GB1711847 A GB 1711847A GB 1711847 A GB1711847 A GB 1711847A GB 641250 A GB641250 A GB 641250A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroperoxides
- benzene
- hydroperoxide
- mono
- aqueous
- 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
- 238000000034 method Methods 0.000 title abstract 5
- -1 di-isopropyl-benzene hydro-peroxides Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 12
- 239000000203 mixture Substances 0.000 abstract 6
- 150000002978 peroxides Chemical group 0.000 abstract 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 239000007788 liquid Substances 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- 239000001301 oxygen Substances 0.000 abstract 4
- 239000003513 alkali Substances 0.000 abstract 3
- 150000002432 hydroperoxides Chemical class 0.000 abstract 3
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
- 239000006227 byproduct Substances 0.000 abstract 2
- 239000013065 commercial product Substances 0.000 abstract 2
- 239000006185 dispersion Substances 0.000 abstract 2
- 239000000839 emulsion Substances 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 150000002989 phenols Chemical class 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 abstract 2
- 238000005406 washing Methods 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
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 abstract 1
- HEOVGVNITGAUKL-UHFFFAOYSA-N 3-Methyl-1-phenyl-1-butanone Chemical class CC(C)CC(=O)C1=CC=CC=C1 HEOVGVNITGAUKL-UHFFFAOYSA-N 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 238000010521 absorption reaction Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- WSPJXOUAPDKTOI-UHFFFAOYSA-N benzene 2-diazoacetic acid Chemical compound [N+](=[N-])=CC(=O)O.C1=CC=CC=C1 WSPJXOUAPDKTOI-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 230000005587 bubbling Effects 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 229910001882 dioxygen Inorganic materials 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 239000011790 ferrous sulphate Substances 0.000 abstract 1
- 235000003891 ferrous sulphate Nutrition 0.000 abstract 1
- 238000005194 fractionation Methods 0.000 abstract 1
- 229910001385 heavy metal Inorganic materials 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 150000002736 metal compounds Chemical class 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 235000010755 mineral Nutrition 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical class [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 235000010265 sodium sulphite Nutrition 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- 238000010792 warming Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
-
- 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
- C07C407/00—Preparation of peroxy compounds
- C07C407/003—Separation; Purification; Stabilisation; Use of additives
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE498321D BE498321A (enrdf_load_stackoverflow) | 1947-06-28 | ||
| GB1711847A GB641250A (en) | 1947-06-28 | 1947-06-28 | Process for the manufacture of di-isopropyl-benzene hydro-peroxides and products resulting therefrom |
| FR968209D FR968209A (fr) | 1947-06-28 | 1948-06-25 | Composés peroxydés |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1711847A GB641250A (en) | 1947-06-28 | 1947-06-28 | Process for the manufacture of di-isopropyl-benzene hydro-peroxides and products resulting therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB641250A true GB641250A (en) | 1950-08-09 |
Family
ID=10089580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1711847A Expired GB641250A (en) | 1947-06-28 | 1947-06-28 | Process for the manufacture of di-isopropyl-benzene hydro-peroxides and products resulting therefrom |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE498321A (enrdf_load_stackoverflow) |
| FR (1) | FR968209A (enrdf_load_stackoverflow) |
| GB (1) | GB641250A (enrdf_load_stackoverflow) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2785205A (en) * | 1954-07-01 | 1957-03-12 | Hercules Powder Co Ltd | Recovery of phenols |
| US2820832A (en) * | 1954-06-18 | 1958-01-21 | Ici Ltd | Production of hydroperoxides |
| DE969266C (de) * | 1951-04-28 | 1958-05-14 | Rhone Poulenc Sa | Verfahren zur Herstellung von Cumolhydroperoxyd durch katalytische Oxydation von Cumol |
| US2862857A (en) * | 1954-07-01 | 1958-12-02 | Hercules Powder Co Ltd | Azeotropic distillation of monohydric and dihydric phenols |
| US2911391A (en) * | 1952-12-31 | 1959-11-03 | Hercules Powder Co Ltd | Polymer hydroperoxides |
| US2915557A (en) * | 1956-06-05 | 1959-12-01 | Shell Dev | Process for recovering di-isopropylbenzene-di-hydroperoxide from di-isopropylbenzene oxidation products |
| US2950320A (en) * | 1953-05-27 | 1960-08-23 | Hercules Powder Co Ltd | 5-benzoyl pentanol-1 |
| DE1247313B (de) * | 1959-06-24 | 1967-08-17 | Hibernia Ag | Verfahren zur Gewinnung von Diisopropylbenzol-Dihydroperoxyden |
| US3993696A (en) * | 1973-05-02 | 1976-11-23 | Sumitomo Chemical Company, Limited | Method for recovering hydroperoxide |
| EP0084417A1 (en) * | 1982-01-07 | 1983-07-27 | Sumitomo Chemical Company, Limited | Production of aromatic carbonyl compounds including novel acetophenones |
| EP0012613B1 (en) * | 1978-12-14 | 1984-08-08 | Mobil Oil Corporation | A process for producing 3-alkylphenols and 1,3-dihydroxybenzene |
| US4929771A (en) * | 1987-12-09 | 1990-05-29 | Ciba-Geigy Corporation | Process for the preparation of alkyl-substituted phenols or naphthols |
| EP0796833A3 (de) * | 1996-03-20 | 1998-04-01 | Rütgers Kureha Solvents GmbH | Verfahren zur Herstellung von Hydroxyaromaten |
| CN113135819A (zh) * | 2021-04-29 | 2021-07-20 | 北京工业大学 | 一种提高间二异丙苯氧化制备间苯二酚的收率的方法 |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE947308C (de) * | 1952-06-19 | 1956-08-16 | Rhone Poulenc Sa | Verfahren zur Herstellung von Hydrochinon |
| DE947309C (de) * | 1952-06-19 | 1956-08-16 | Rhone Poulenc Sa | Verfahren zur Herstellung von Hydrochinon |
| DE961168C (de) * | 1952-08-23 | 1957-04-04 | Distillers Co Yeast Ltd | Verfahren zur Herstellung von m- und p-Diisopropylbenzoldihydroperoxyden |
| US2736753A (en) * | 1952-09-10 | 1956-02-28 | Hercules Powder Co Ltd | Recovery of phenols |
| US2790010A (en) * | 1952-12-18 | 1957-04-23 | Hooker Electrochemical Co | Synthesis of meta-substituted phenols |
| US2784238A (en) * | 1953-02-21 | 1957-03-05 | Hercules Powder Co Ltd | Catalyst reactivation in process for production of resorcinols |
| DE1084731B (de) * | 1953-06-13 | 1960-07-07 | Distillers Co Yeast Ltd | Verfahren zur Herstellung von Resorcin |
| US2820064A (en) * | 1953-06-24 | 1958-01-14 | Eastman Kodak Co | Autoxidation of hydrocarbons |
| US2856432A (en) * | 1953-09-04 | 1958-10-14 | Hercules Powder Co Ltd | Aromatic dihydroperoxide production |
| DE961708C (de) * | 1953-09-05 | 1957-04-11 | Distillers Co Yeast Ltd | Verfahren zur Gewinnung von Dihydroperoxyden aus den bei der Oxydation substituierter aromatischer Kohlenwasserstoffe erhaltenen Gemischen |
| US2856433A (en) * | 1953-09-05 | 1958-10-14 | Hercules Powder Co Ltd | Separation of organic compounds |
| US2812357A (en) * | 1954-01-12 | 1957-11-05 | Hercules Powder Co Ltd | Removal of hydroperoxide carbinols from aromatic hydroperoxides |
| US2805258A (en) * | 1955-05-23 | 1957-09-03 | Koppers Co Inc | Process for the preparation of hydroperoxides from diisopropylbenzenes |
| DE1643971C3 (de) * | 1967-07-13 | 1975-04-10 | Bayer Ag, 5090 Leverkusen | m- und p-lsopropenylphenyl-dimethylcarbinol und Verfahren zu deren Herstellung |
-
0
- BE BE498321D patent/BE498321A/xx unknown
-
1947
- 1947-06-28 GB GB1711847A patent/GB641250A/en not_active Expired
-
1948
- 1948-06-25 FR FR968209D patent/FR968209A/fr not_active Expired
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE969266C (de) * | 1951-04-28 | 1958-05-14 | Rhone Poulenc Sa | Verfahren zur Herstellung von Cumolhydroperoxyd durch katalytische Oxydation von Cumol |
| US2911391A (en) * | 1952-12-31 | 1959-11-03 | Hercules Powder Co Ltd | Polymer hydroperoxides |
| US2950320A (en) * | 1953-05-27 | 1960-08-23 | Hercules Powder Co Ltd | 5-benzoyl pentanol-1 |
| US2820832A (en) * | 1954-06-18 | 1958-01-21 | Ici Ltd | Production of hydroperoxides |
| US2862857A (en) * | 1954-07-01 | 1958-12-02 | Hercules Powder Co Ltd | Azeotropic distillation of monohydric and dihydric phenols |
| US2785205A (en) * | 1954-07-01 | 1957-03-12 | Hercules Powder Co Ltd | Recovery of phenols |
| US2915557A (en) * | 1956-06-05 | 1959-12-01 | Shell Dev | Process for recovering di-isopropylbenzene-di-hydroperoxide from di-isopropylbenzene oxidation products |
| DE1247313B (de) * | 1959-06-24 | 1967-08-17 | Hibernia Ag | Verfahren zur Gewinnung von Diisopropylbenzol-Dihydroperoxyden |
| US3993696A (en) * | 1973-05-02 | 1976-11-23 | Sumitomo Chemical Company, Limited | Method for recovering hydroperoxide |
| EP0012613B1 (en) * | 1978-12-14 | 1984-08-08 | Mobil Oil Corporation | A process for producing 3-alkylphenols and 1,3-dihydroxybenzene |
| EP0084417A1 (en) * | 1982-01-07 | 1983-07-27 | Sumitomo Chemical Company, Limited | Production of aromatic carbonyl compounds including novel acetophenones |
| US4929771A (en) * | 1987-12-09 | 1990-05-29 | Ciba-Geigy Corporation | Process for the preparation of alkyl-substituted phenols or naphthols |
| EP0796833A3 (de) * | 1996-03-20 | 1998-04-01 | Rütgers Kureha Solvents GmbH | Verfahren zur Herstellung von Hydroxyaromaten |
| US6107527A (en) * | 1996-03-20 | 2000-08-22 | Rutgers Kureha Solvents Gmbh | Process for the production of hydroxy-aromatic substances |
| CN113135819A (zh) * | 2021-04-29 | 2021-07-20 | 北京工业大学 | 一种提高间二异丙苯氧化制备间苯二酚的收率的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| BE498321A (enrdf_load_stackoverflow) | |
| FR968209A (fr) | 1950-11-22 |
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