GB999441A - Cumene oxidation - Google Patents
Cumene oxidationInfo
- Publication number
- GB999441A GB999441A GB3024563A GB3024563A GB999441A GB 999441 A GB999441 A GB 999441A GB 3024563 A GB3024563 A GB 3024563A GB 3024563 A GB3024563 A GB 3024563A GB 999441 A GB999441 A GB 999441A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cumene
- oxidation
- sodium hydroxide
- towers
- reaction mixture
- 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 22
- 238000007254 oxidation reaction Methods 0.000 title abstract 8
- 230000003647 oxidation Effects 0.000 title abstract 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 15
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 abstract 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 4
- 239000011541 reaction mixture Substances 0.000 abstract 4
- 239000005711 Benzoic acid Substances 0.000 abstract 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 235000010233 benzoic acid Nutrition 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- 238000010521 absorption reaction Methods 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003610 charcoal Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000010924 continuous production Methods 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 abstract 1
- 239000000347 magnesium hydroxide Substances 0.000 abstract 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000126 substance Substances 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
- C07C409/04—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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A continuous process for the preparation of cumene hydroperoxide by the oxidation of cumene, in which unreacted cumene is removed from the oxidation reaction mixture leaving a residue rich in cumene hydroperoxide, the separated cumene is treated with an aqueous solution of sodium hydroxide having a concentration not greater than 3% by weight, the ratio of cumene: sodium hydroxide solution being such that the cumene after the treatment has a pH of at least 3.5 and an acid concentration (calculated as benzoic acid) of not more than 500 parts per million; and any unreacted sodium hydroxide is separated from the treated cumene which is then returned to the oxidation stage. In a preferred form of the invention a cumene oxidation reaction mixture is passed successively through three or four towers and contacted with air bubbled up at about atmospheric pressure, the temperature levels in the successive towers, being successively lower, e.g. at about 105-115 DEG C. in the first tower, about 95-105 DEG C. in the second and third towers and about 90-100 DEG C. in the last tower. A neutral to mildly basic, e.g. pH of 7-10.5, substantially water-insoluble, powdered substance, e.g. calcium carbonate or magnesium hydroxide, is suspended in the reaction mixture as a promoter or catalyst of the desired oxidation. The cumene hydroperoxide concentration is brought to about 25-40% by weight of the reaction mixture in the final tower; and this crude oxidation product is flash distilled under vacuum to leave about 75-90 weight per cent crude cumene hydroperoxide. The distilled cumene is recovered by condensation, and cumene in the exhaust gases from the towers is recovered by absorption on charcoal and in each case is washed with aqueous sodium hydroxide solution in proportions between about 100 : 1 and about 1000: 1 of cumene:aqueous sodium hydroxide by volume, separated from the aqueous layer, filtered and recycled to the oxidation zone as a clear stream having pH of about 4.0 to 7.0, and having an acid concentration of about 100 p.p.m. to nil calculated as benzoic acid. An example is given.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21486462A | 1962-08-06 | 1962-08-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB999441A true GB999441A (en) | 1965-07-28 |
Family
ID=22800704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3024563A Expired GB999441A (en) | 1962-08-06 | 1963-07-30 | Cumene oxidation |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1443379A1 (en) |
| GB (1) | GB999441A (en) |
| NL (1) | NL296118A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2631016A1 (en) * | 1975-07-10 | 1977-01-27 | Halcon International Inc | PROCESS FOR THE PRODUCTION OF ORGANOHYDROPEROXIDES |
-
0
- NL NL296118D patent/NL296118A/xx unknown
-
1963
- 1963-07-30 GB GB3024563A patent/GB999441A/en not_active Expired
- 1963-07-31 DE DE19631443379 patent/DE1443379A1/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2631016A1 (en) * | 1975-07-10 | 1977-01-27 | Halcon International Inc | PROCESS FOR THE PRODUCTION OF ORGANOHYDROPEROXIDES |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1443379A1 (en) | 1968-11-14 |
| NL296118A (en) |
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