GB981707A - Recovery of oxidation products - Google Patents
Recovery of oxidation productsInfo
- Publication number
- GB981707A GB981707A GB4897563A GB4897563A GB981707A GB 981707 A GB981707 A GB 981707A GB 4897563 A GB4897563 A GB 4897563A GB 4897563 A GB4897563 A GB 4897563A GB 981707 A GB981707 A GB 981707A
- Authority
- GB
- United Kingdom
- Prior art keywords
- organic phase
- alkali
- dihydroperoxide
- washing
- carbon dioxide
- 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 abstract 4
- 238000007254 oxidation reaction Methods 0.000 title abstract 4
- 238000011084 recovery Methods 0.000 title 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 14
- 239000012074 organic phase Substances 0.000 abstract 9
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 239000003513 alkali Substances 0.000 abstract 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 3
- 239000001569 carbon dioxide Substances 0.000 abstract 3
- 238000005406 washing Methods 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 2
- 229910001882 dioxygen Inorganic materials 0.000 abstract 2
- 238000000605 extraction Methods 0.000 abstract 2
- 238000000926 separation method Methods 0.000 abstract 2
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical class CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000012071 phase Substances 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- 239000012266 salt solution Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000005201 scrubbing Methods 0.000 abstract 1
- 239000001488 sodium phosphate Substances 0.000 abstract 1
- 229910000162 sodium phosphate Inorganic materials 0.000 abstract 1
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract 1
- 235000011152 sodium sulphate Nutrition 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 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
- C07C409/12—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
- 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
- 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
Dihydroperoxides are made by oxidation of dialkyl aromatic hydrocarbons of the formula <FORM:0981707/C2/1> wherein Ar is an arylene group and R1, R2, R3 and R4 are alkyl groups, by contacting the dialkyl aromatic hydrocarbon with molecular oxygen, subjecting the oxidate which contains the monohydroperoxide and dihydroperoxide of the dialkyl aromatic hydrocarbon to extraction with an aqueous solution of an alkali metal hydroxide to remove the dihydroperoxide, treating the resultant organic phase which is substantially free from dihydroperoxide with gaseous carbon dioxide, washing the so treated organic phase with water, and recycling the washed organic phase to the oxidation stage. Preferred hydrocarbons are m- and p-diisopropylbenzenes. The oxidation is preferably effected at a pH within the range from 3 to 7 using molecular oxygen either alone or diluted with nitrogen at temperatures in the range from 50 DEG to 150 DEG C. The alkali may be sodium hydroxide or potassium hydroxide preferable in an aqueous solu containing 1 to 12% by weight of alkali metal hydroxide. The treatment of the organic phase with carbon dioxide may be carried out at temperatures ranging from 15 DEG to 80 DEG C. at least sufficient CO2 being employed to neutralize the alkali content. The gas may be introduced through suitable distribution apparatus and preferably the organic phase and carbon dioxide are passed in countercurrent flow through a packed column. The treated organic phase is washed with water to remove salts, the washing being effected after, or simultaneously with, the CO2 treatment. Thus the water may be fed in with the organic phase at the top of a scrubbing column wherein CO2 passes in countercurrent flow. The separation of the phases after the alkali extraction, and the separation of the aqueous salt solution from the organic phase after washing, may be effected by centrifuging. Detailed examples are given and the effect of neutralizing the organic phase with CO2 is compared with neutralization using sodium sulphate containing sulphuric acid or buffered sodium phosphate solution.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1962SC032485 DE1237118B (en) | 1962-12-17 | 1962-12-17 | Process for carrying out the known oxidation of di-tert-alkyl aromatic hydrocarbons in the liquid state and in circulation with oxygen or oxygen-containing gases at elevated temperature to give aryl-di-tert-alkyl dihydroperoxides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB981707A true GB981707A (en) | 1965-01-27 |
Family
ID=7432459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4897563A Expired GB981707A (en) | 1962-12-17 | 1963-12-11 | Recovery of oxidation products |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT247307B (en) |
| DE (1) | DE1237118B (en) |
| DK (1) | DK128604B (en) |
| GB (1) | GB981707A (en) |
| LU (1) | LU45041A1 (en) |
| NL (1) | NL301578A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0105019A3 (en) * | 1982-09-29 | 1985-10-30 | The Goodyear Tire & Rubber Company | Dihydric phenol recovery process |
| CN113135819A (en) * | 2021-04-29 | 2021-07-20 | 北京工业大学 | Method for improving yield of resorcinol prepared by m-diisopropylbenzene oxidation |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5741466B2 (en) * | 1973-10-29 | 1982-09-03 | ||
| US4935551A (en) * | 1987-12-22 | 1990-06-19 | Indspec Chemical Corporation | Hydroperoxidation of diisopropylbenzene |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1102740B (en) * | 1959-07-13 | 1961-03-23 | Phenolchemie Ges Mit Beschraen | Process for the production of hydroperoxides from the oxidation products of dialkylated aromatic hydrocarbons |
-
0
- NL NL301578D patent/NL301578A/xx unknown
-
1962
- 1962-12-17 DE DE1962SC032485 patent/DE1237118B/en active Pending
-
1963
- 1963-12-09 AT AT985563A patent/AT247307B/en active
- 1963-12-11 GB GB4897563A patent/GB981707A/en not_active Expired
- 1963-12-16 DK DK585063A patent/DK128604B/en unknown
- 1963-12-17 LU LU45041A patent/LU45041A1/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0105019A3 (en) * | 1982-09-29 | 1985-10-30 | The Goodyear Tire & Rubber Company | Dihydric phenol recovery process |
| CN113135819A (en) * | 2021-04-29 | 2021-07-20 | 北京工业大学 | Method for improving yield of resorcinol prepared by m-diisopropylbenzene oxidation |
Also Published As
| Publication number | Publication date |
|---|---|
| NL301578A (en) | |
| DE1237118B (en) | 1967-03-23 |
| DK128604B (en) | 1974-06-04 |
| LU45041A1 (en) | 1964-02-17 |
| AT247307B (en) | 1966-06-10 |
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