CA1125789A - Separation of phenols - Google Patents
Separation of phenolsInfo
- Publication number
- CA1125789A CA1125789A CA344,754A CA344754A CA1125789A CA 1125789 A CA1125789 A CA 1125789A CA 344754 A CA344754 A CA 344754A CA 1125789 A CA1125789 A CA 1125789A
- Authority
- CA
- Canada
- Prior art keywords
- alkali metal
- phenols
- cresol
- cresols
- metal salt
- 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
- 150000002989 phenols Chemical class 0.000 title claims abstract description 17
- 238000000926 separation method Methods 0.000 title abstract 2
- 239000002253 acid Substances 0.000 claims abstract description 23
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000007513 acids Chemical class 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 15
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 claims abstract description 14
- -1 alkali metal salt Chemical class 0.000 claims abstract description 14
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims abstract description 9
- 150000008041 alkali metal carbonates Chemical class 0.000 claims abstract description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims abstract description 6
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 24
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 17
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 11
- 239000001569 carbon dioxide Substances 0.000 claims description 11
- 229930003836 cresol Natural products 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 7
- 238000010926 purge Methods 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000011280 coal tar Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 150000001896 cresols Chemical class 0.000 abstract description 22
- 150000003839 salts Chemical class 0.000 abstract description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 239000011269 tar Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 5
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003739 xylenols Chemical class 0.000 description 2
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000003295 industrial effluent Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000011289 tar acid Substances 0.000 description 1
- 239000002641 tar oil 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
- C07C37/86—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 |
|---|---|---|---|
| US053,968 | 1979-07-02 | ||
| US06/053,968 US4275246A (en) | 1979-07-02 | 1979-07-02 | Separation of phenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1125789A true CA1125789A (en) | 1982-06-15 |
Family
ID=21987809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA344,754A Expired CA1125789A (en) | 1979-07-02 | 1980-01-31 | Separation of phenols |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4275246A (enExample) |
| JP (1) | JPS5940371B2 (enExample) |
| AU (1) | AU529371B2 (enExample) |
| BE (1) | BE881475A (enExample) |
| CA (1) | CA1125789A (enExample) |
| DE (1) | DE3005200A1 (enExample) |
| FR (1) | FR2460282A1 (enExample) |
| GB (1) | GB2053192B (enExample) |
| IT (1) | IT1127337B (enExample) |
| ZA (1) | ZA80725B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4547596A (en) * | 1983-03-30 | 1985-10-15 | General Electric Company | Separation and recovery of alkylated phenols |
| US9162952B2 (en) | 2013-11-19 | 2015-10-20 | Uop Llc | Process for purifying products from coal tar |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB815754A (en) * | 1955-12-01 | 1959-07-01 | Leuna Werke Veb | Process for extracting phenols from phenolic oils |
| US1445668A (en) * | 1920-11-29 | 1923-02-20 | Peter C Reilly | Process of producing cresol |
| US1980384A (en) * | 1933-11-25 | 1934-11-13 | Monsanto Chemicals | Separation of meta cresol from meta cresol-para cresol mixtures |
| US3517072A (en) * | 1963-10-28 | 1970-06-23 | Consolidation Coal Co | High purity 2,6-xylenol |
| US4001341A (en) * | 1964-01-24 | 1977-01-04 | General Electric Company | Extraction separation |
| GB1316276A (en) * | 1969-12-12 | 1973-05-09 | Coalite Chemical Products Ltd | Separation of chlorophenols |
| JPS5198228A (ja) * | 1975-02-19 | 1976-08-30 | Arukirufuenooruiseitaino bunriho |
-
1979
- 1979-07-02 US US06/053,968 patent/US4275246A/en not_active Expired - Lifetime
-
1980
- 1980-01-23 AU AU54854/80A patent/AU529371B2/en not_active Ceased
- 1980-01-31 CA CA344,754A patent/CA1125789A/en not_active Expired
- 1980-01-31 BE BE0/199209A patent/BE881475A/fr unknown
- 1980-02-01 JP JP55011370A patent/JPS5940371B2/ja not_active Expired
- 1980-02-05 IT IT47808/80A patent/IT1127337B/it active
- 1980-02-07 ZA ZA00800725A patent/ZA80725B/xx unknown
- 1980-02-12 DE DE19803005200 patent/DE3005200A1/de not_active Withdrawn
- 1980-02-15 FR FR8003405A patent/FR2460282A1/fr active Granted
- 1980-03-25 GB GB8010006A patent/GB2053192B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2053192B (en) | 1983-09-07 |
| ZA80725B (en) | 1981-02-25 |
| FR2460282B1 (enExample) | 1983-12-16 |
| DE3005200A1 (de) | 1981-01-22 |
| AU5485480A (en) | 1981-01-15 |
| AU529371B2 (en) | 1983-06-02 |
| JPS5940371B2 (ja) | 1984-09-29 |
| BE881475A (fr) | 1980-05-16 |
| JPS5610126A (en) | 1981-02-02 |
| FR2460282A1 (fr) | 1981-01-23 |
| IT8047808A0 (it) | 1980-02-05 |
| US4275246A (en) | 1981-06-23 |
| IT1127337B (it) | 1986-05-21 |
| GB2053192A (en) | 1981-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |