DE1060868B - Verfahren zur Gewinnung von reinem Phenol - Google Patents
Verfahren zur Gewinnung von reinem PhenolInfo
- Publication number
- DE1060868B DE1060868B DED12688A DED0012688A DE1060868B DE 1060868 B DE1060868 B DE 1060868B DE D12688 A DED12688 A DE D12688A DE D0012688 A DED0012688 A DE D0012688A DE 1060868 B DE1060868 B DE 1060868B
- Authority
- DE
- Germany
- Prior art keywords
- phenol
- mixture
- distillation
- methylstyrene
- isopropylbenzene
- 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.)
- Pending
Links
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims description 94
- 238000000034 method Methods 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000000203 mixture Substances 0.000 claims description 59
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 52
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 38
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 claims description 34
- 238000004821 distillation Methods 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 26
- 238000000354 decomposition reaction Methods 0.000 claims description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 20
- 238000004508 fractional distillation Methods 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 12
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical group OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 claims description 11
- CJWNFAKWHDOUKL-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)phenol Chemical group C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1 CJWNFAKWHDOUKL-UHFFFAOYSA-N 0.000 claims description 9
- 238000000926 separation method Methods 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 5
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 claims description 3
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 claims description 3
- 238000003421 catalytic decomposition reaction Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims 2
- 238000005336 cracking Methods 0.000 claims 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 21
- 229930195733 hydrocarbon Natural products 0.000 description 13
- 150000002430 hydrocarbons Chemical class 0.000 description 13
- 238000009835 boiling Methods 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000003776 cleavage reaction Methods 0.000 description 5
- 230000007017 scission Effects 0.000 description 5
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 4
- 230000033228 biological regulation Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- -1 α-methylstyrene Chemical class 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- UFOFRAGRYOYPKN-UHFFFAOYSA-N hydrogen peroxide;propylbenzene Chemical class OO.CCCC1=CC=CC=C1 UFOFRAGRYOYPKN-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- 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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB305422X | 1951-07-18 | ||
| GB230652X | 1952-06-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1060868B true DE1060868B (de) | 1959-07-09 |
Family
ID=26256292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED12688A Pending DE1060868B (de) | 1951-07-18 | 1952-07-08 | Verfahren zur Gewinnung von reinem Phenol |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE512888A (en, 2012) |
| CH (1) | CH305422A (en, 2012) |
| DE (1) | DE1060868B (en, 2012) |
| FR (1) | FR1065345A (en, 2012) |
| IT (1) | IT490392A (en, 2012) |
| LU (1) | LU31582A1 (en, 2012) |
| NL (2) | NL90104C (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1219035B (de) | 1961-04-26 | 1966-06-16 | Inst Gorjutschich Iskopajemych | Verfahren zum Aufarbeiten der Destillations-rueckstaende, die bei der Herstellung von Phenol durch Spalten von Cumolhydroperoxyd erhalten worden sind |
| DE2150076A1 (de) * | 1970-10-08 | 1972-04-13 | Hercules Inc | Verfahren zur Herstellung eines Phenolproduktes mit einem betraechtlich herabgesetzten Acetonphenongehalt aus einem Phenol-Acetophenon-Azeotrop |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1075120B (de) * | 1960-02-11 | Rutgerswerke Aktiengesellschaft Frankfurt/M | Verfahren zur Gewinnung von Remphenol aus dem bei der Phenolherstel lung aus Cumolhydroperoxyd entstehenden Rohphenol | |
| IT608859A (en, 2012) * | 1958-03-04 | |||
| DE1121621B (de) * | 1959-04-06 | 1962-01-11 | Phenolchemie Ges Mit Beschraen | Verfahren zum Aufarbeiten der Destillationsrueckstaende, die bei der Herstellung von Phenol und Aceton durch Spalten von Cumolhydroperoxyd erhalten werden |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE496062A (en, 2012) * | 1949-06-08 | |||
| FR961022A (en, 2012) * | 1947-02-13 | 1950-04-28 |
-
0
- LU LU31582D patent/LU31582A1/xx unknown
- IT IT490392D patent/IT490392A/it unknown
- NL NLAANVRAGE7201028,A patent/NL170964B/xx unknown
- BE BE512888D patent/BE512888A/fr unknown
- NL NL90104D patent/NL90104C/xx active
-
1952
- 1952-07-05 FR FR1065345D patent/FR1065345A/fr not_active Expired
- 1952-07-08 DE DED12688A patent/DE1060868B/de active Pending
- 1952-07-12 CH CH305422D patent/CH305422A/fr unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR961022A (en, 2012) * | 1947-02-13 | 1950-04-28 | ||
| BE496062A (en, 2012) * | 1949-06-08 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1219035B (de) | 1961-04-26 | 1966-06-16 | Inst Gorjutschich Iskopajemych | Verfahren zum Aufarbeiten der Destillations-rueckstaende, die bei der Herstellung von Phenol durch Spalten von Cumolhydroperoxyd erhalten worden sind |
| DE2150076A1 (de) * | 1970-10-08 | 1972-04-13 | Hercules Inc | Verfahren zur Herstellung eines Phenolproduktes mit einem betraechtlich herabgesetzten Acetonphenongehalt aus einem Phenol-Acetophenon-Azeotrop |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1065345A (fr) | 1954-05-24 |
| IT490392A (en, 2012) | |
| CH305422A (fr) | 1955-02-28 |
| BE512888A (en, 2012) | |
| LU31582A1 (en, 2012) | |
| NL90104C (en, 2012) | |
| NL170964B (nl) |
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