DE2030994A1 - Verfahren zur Abtrennung von Phenyl phenolen und Resorcin aus Mischungen die diese Verbindungen enthalten - Google Patents
Verfahren zur Abtrennung von Phenyl phenolen und Resorcin aus Mischungen die diese Verbindungen enthaltenInfo
- Publication number
- DE2030994A1 DE2030994A1 DE19702030994 DE2030994A DE2030994A1 DE 2030994 A1 DE2030994 A1 DE 2030994A1 DE 19702030994 DE19702030994 DE 19702030994 DE 2030994 A DE2030994 A DE 2030994A DE 2030994 A1 DE2030994 A1 DE 2030994A1
- Authority
- DE
- Germany
- Prior art keywords
- solvent
- resorcinol
- water
- phenylphenol
- aqueous phase
- 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
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 title claims description 88
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical class OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 title claims description 40
- 238000000034 method Methods 0.000 title claims description 27
- 239000000203 mixture Substances 0.000 title claims description 27
- 238000000926 separation method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 title claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
- 239000002904 solvent Substances 0.000 claims description 38
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 37
- 239000008346 aqueous phase Substances 0.000 claims description 29
- 239000012071 phase Substances 0.000 claims description 19
- 238000000605 extraction Methods 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 10
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 8
- 235000010292 orthophenyl phenol Nutrition 0.000 claims description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 230000005484 gravity Effects 0.000 claims description 2
- 239000004306 orthophenyl phenol Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000000284 extract Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 238000004821 distillation Methods 0.000 description 10
- 239000000463 material Substances 0.000 description 7
- 239000003513 alkali Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- MIAUJDCQDVWHEV-UHFFFAOYSA-N benzene-1,2-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O MIAUJDCQDVWHEV-UHFFFAOYSA-N 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WEJVHFVGNQBRGH-UHFFFAOYSA-N 2,3,4,6-tetramethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1C WEJVHFVGNQBRGH-UHFFFAOYSA-N 0.000 description 1
- MZZFCCMTELEPFL-UHFFFAOYSA-N 2-phenylphenol;4-phenylphenol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1.OC1=CC=CC=C1C1=CC=CC=C1 MZZFCCMTELEPFL-UHFFFAOYSA-N 0.000 description 1
- PMLQZTOGKPQMKO-UHFFFAOYSA-L C1(O)=C(C(O)=CC=C1)C(=O)[O-].[Na+].[Na+].C1(O)=C(C(O)=CC=C1)C(=O)[O-] Chemical compound C1(O)=C(C(O)=CC=C1)C(=O)[O-].[Na+].[Na+].C1(O)=C(C(O)=CC=C1)C(=O)[O-] PMLQZTOGKPQMKO-UHFFFAOYSA-L 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- KSQXVLVXUFHGJQ-UHFFFAOYSA-M Sodium ortho-phenylphenate Chemical compound [Na+].[O-]C1=CC=CC=C1C1=CC=CC=C1 KSQXVLVXUFHGJQ-UHFFFAOYSA-M 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 1
- DALDUXIBIKGWTK-UHFFFAOYSA-N benzene;toluene Chemical compound C1=CC=CC=C1.CC1=CC=CC=C1 DALDUXIBIKGWTK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- -1 o-phenylphenol Chemical class 0.000 description 1
- FTDXCHCAMNRNNY-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1 FTDXCHCAMNRNNY-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 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
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/72—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6269869A JPS5011896B1 (enrdf_load_stackoverflow) | 1969-08-08 | 1969-08-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2030994A1 true DE2030994A1 (de) | 1971-02-18 |
Family
ID=13207759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702030994 Pending DE2030994A1 (de) | 1969-08-08 | 1970-06-23 | Verfahren zur Abtrennung von Phenyl phenolen und Resorcin aus Mischungen die diese Verbindungen enthalten |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5011896B1 (enrdf_load_stackoverflow) |
| DE (1) | DE2030994A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2057053B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1308026A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4239921A (en) * | 1978-07-10 | 1980-12-16 | Mitsu, Petrochemical Industries, Ltd. | Process for purification of crude resorcinol |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0480308A1 (de) * | 1990-10-08 | 1992-04-15 | Hoechst Aktiengesellschaft | Verfahren zur Abtrennung von Resorcin aus Resorcin-Vorkondensaten |
-
1969
- 1969-08-08 JP JP6269869A patent/JPS5011896B1/ja active Pending
-
1970
- 1970-06-03 GB GB2675570A patent/GB1308026A/en not_active Expired
- 1970-06-23 DE DE19702030994 patent/DE2030994A1/de active Pending
- 1970-06-30 FR FR7024122A patent/FR2057053B1/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4239921A (en) * | 1978-07-10 | 1980-12-16 | Mitsu, Petrochemical Industries, Ltd. | Process for purification of crude resorcinol |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2057053A1 (enrdf_load_stackoverflow) | 1971-05-07 |
| JPS5011896B1 (enrdf_load_stackoverflow) | 1975-05-07 |
| FR2057053B1 (enrdf_load_stackoverflow) | 1973-01-12 |
| GB1308026A (en) | 1973-02-21 |
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