CA1097377A - Process for the purification of a phenol - Google Patents
Process for the purification of a phenolInfo
- Publication number
- CA1097377A CA1097377A CA287,187A CA287187A CA1097377A CA 1097377 A CA1097377 A CA 1097377A CA 287187 A CA287187 A CA 287187A CA 1097377 A CA1097377 A CA 1097377A
- Authority
- CA
- Canada
- Prior art keywords
- column
- phenol
- acid
- benzene
- phosphoric acid
- 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims abstract description 14
- 238000000746 purification Methods 0.000 title claims abstract description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 36
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 16
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 14
- 230000003647 oxidation Effects 0.000 claims abstract description 12
- -1 phenol compound Chemical class 0.000 claims abstract description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract description 11
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract description 6
- 235000010233 benzoic acid Nutrition 0.000 abstract description 5
- 239000005711 Benzoic acid Substances 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 150000003935 benzaldehydes Chemical class 0.000 abstract description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 229910001882 dioxygen Inorganic materials 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000005749 Copper compound Substances 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001868 cobalt Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 1
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000004401 m-toluyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C(*)=O 0.000 description 1
- PJJZFXPJNUVBMR-UHFFFAOYSA-L magnesium benzoate Chemical compound [Mg+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 PJJZFXPJNUVBMR-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 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
- C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7610598 | 1976-09-24 | ||
| NL7610598A NL7610598A (nl) | 1976-09-24 | 1976-09-24 | Werkwijze voor het zuiveren van een door oxidatie via een benzeenmonocarbonzuur uit een alkylbenzeenverbinding bereid fenol. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1097377A true CA1097377A (en) | 1981-03-10 |
Family
ID=19826961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA287,187A Expired CA1097377A (en) | 1976-09-24 | 1977-09-21 | Process for the purification of a phenol |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4154964A (en:Method) |
| JP (1) | JPS5340730A (en:Method) |
| BE (1) | BE858603A (en:Method) |
| CA (1) | CA1097377A (en:Method) |
| DE (1) | DE2742930A1 (en:Method) |
| ES (1) | ES462417A1 (en:Method) |
| FR (1) | FR2365544A1 (en:Method) |
| GB (1) | GB1577560A (en:Method) |
| IN (1) | IN147209B (en:Method) |
| IT (1) | IT1090002B (en:Method) |
| NL (1) | NL7610598A (en:Method) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52130138U (en:Method) * | 1976-03-31 | 1977-10-03 | ||
| US5210331A (en) * | 1989-12-19 | 1993-05-11 | Dsm Nv | Method for the preparation of a phenol |
| BE1004951A4 (nl) * | 1991-06-14 | 1993-03-02 | Dsm Nv | Werkwijze voor de bereiding van een fenol. |
| US5025090A (en) * | 1990-02-01 | 1991-06-18 | Akzo Nv | Decolorization of dihydroxydiphenyl sulfone |
| US5962751A (en) * | 1996-04-26 | 1999-10-05 | General Electric Company | Phenol tar desalting method |
| US5777171A (en) * | 1997-10-17 | 1998-07-07 | Swearengin; John V. | Method of purifying arylphenones |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA705919A (en) * | 1965-03-16 | Stamicarbon N.V. | Phenol from benzoic acid | |
| FR858627A (fr) * | 1938-08-08 | 1940-11-29 | Ig Farbenindustrie Ag | Procédé pour produire des phénols pours à partir de phénols bruts |
| US2301709A (en) * | 1938-08-08 | 1942-11-10 | Rumscheidt Carl | Recovery of pure phenols from crude phenols |
| US2752398A (en) * | 1953-06-23 | 1956-06-26 | Union Carbide & Carbon Corp | Color stabilization of phenols with phosphoric acids |
| US2727928A (en) * | 1953-12-23 | 1955-12-20 | Shell Dev | Stabilization of alkyl phenol compounds |
| US2727926A (en) * | 1954-01-08 | 1955-12-20 | Dow Chemical Co | Catalytic oxidation of armoatic carboxylic acids to phenols |
| NL248138A (en:Method) * | 1959-02-11 | 1900-01-01 | ||
| AT264993B (de) * | 1966-03-09 | 1968-09-25 | Evg Entwicklung Verwert Ges | Querdraht-Einschießgetriebe für Gitterschweißmaschinen |
| FR2119624A5 (en) * | 1970-12-23 | 1972-08-04 | Sumitomo Chemical Co | Defluorescence of cresol - for tricresyl phosphate prepn by treatment with acid and distillation |
-
1976
- 1976-09-24 NL NL7610598A patent/NL7610598A/xx not_active Application Discontinuation
-
1977
- 1977-09-12 BE BE180826A patent/BE858603A/xx unknown
- 1977-09-13 GB GB38168/77A patent/GB1577560A/en not_active Expired
- 1977-09-13 US US05/832,950 patent/US4154964A/en not_active Expired - Lifetime
- 1977-09-16 ES ES462417A patent/ES462417A1/es not_active Expired
- 1977-09-21 CA CA287,187A patent/CA1097377A/en not_active Expired
- 1977-09-21 FR FR7728455A patent/FR2365544A1/fr not_active Withdrawn
- 1977-09-22 JP JP11453377A patent/JPS5340730A/ja active Pending
- 1977-09-22 IT IT51117/77A patent/IT1090002B/it active
- 1977-09-23 DE DE19772742930 patent/DE2742930A1/de not_active Withdrawn
- 1977-11-03 IN IN371/DEL/77A patent/IN147209B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7610598A (nl) | 1978-03-29 |
| ES462417A1 (es) | 1978-06-01 |
| JPS5340730A (en) | 1978-04-13 |
| FR2365544A1 (fr) | 1978-04-21 |
| US4154964A (en) | 1979-05-15 |
| DE2742930A1 (de) | 1978-03-30 |
| BE858603A (nl) | 1978-03-13 |
| IT1090002B (it) | 1985-06-18 |
| GB1577560A (en) | 1980-10-22 |
| IN147209B (en:Method) | 1979-12-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |