JPS6025413B2 - ヒドロキノンの単離および精製方法 - Google Patents
ヒドロキノンの単離および精製方法Info
- Publication number
- JPS6025413B2 JPS6025413B2 JP11830575A JP11830575A JPS6025413B2 JP S6025413 B2 JPS6025413 B2 JP S6025413B2 JP 11830575 A JP11830575 A JP 11830575A JP 11830575 A JP11830575 A JP 11830575A JP S6025413 B2 JPS6025413 B2 JP S6025413B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroquinone
- phenolic
- water
- solution
- aqueous
- 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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 title claims description 181
- 238000000034 method Methods 0.000 title claims description 12
- 238000000746 purification Methods 0.000 title description 6
- 238000002955 isolation Methods 0.000 title 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 62
- 239000000243 solution Substances 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 21
- 150000002576 ketones Chemical class 0.000 claims description 18
- 239000012071 phase Substances 0.000 claims description 18
- 239000008346 aqueous phase Substances 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 description 24
- 238000000605 extraction Methods 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 11
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 10
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- 239000012535 impurity Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000005192 partition Methods 0.000 description 5
- 239000006286 aqueous extract Substances 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 239000004071 soot Substances 0.000 description 2
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000003809 water extraction Methods 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742446992 DE2446992C2 (de) | 1974-10-02 | 1974-10-02 | Verfahren zur Gewinnung einer wäßrigen Lösung von reinem Hydrochinon |
| DE2446992.9 | 1974-10-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5186429A JPS5186429A (en) | 1976-07-29 |
| JPS6025413B2 true JPS6025413B2 (ja) | 1985-06-18 |
Family
ID=5927322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11830575A Expired JPS6025413B2 (ja) | 1974-10-02 | 1975-10-02 | ヒドロキノンの単離および精製方法 |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS6025413B2 (enExample) |
| BE (1) | BE834120A (enExample) |
| DE (1) | DE2446992C2 (enExample) |
| FR (1) | FR2286809A1 (enExample) |
| GB (1) | GB1528375A (enExample) |
| NL (1) | NL7511556A (enExample) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS501011B1 (enExample) * | 1970-06-18 | 1975-01-14 |
-
1974
- 1974-10-02 DE DE19742446992 patent/DE2446992C2/de not_active Expired
-
1975
- 1975-10-01 NL NL7511556A patent/NL7511556A/xx not_active Application Discontinuation
- 1975-10-02 BE BE160626A patent/BE834120A/xx unknown
- 1975-10-02 FR FR7530258A patent/FR2286809A1/fr active Granted
- 1975-10-02 JP JP11830575A patent/JPS6025413B2/ja not_active Expired
- 1975-10-02 GB GB4042675A patent/GB1528375A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2286809A1 (fr) | 1976-04-30 |
| DE2446992C2 (de) | 1983-06-30 |
| GB1528375A (en) | 1978-10-11 |
| NL7511556A (nl) | 1976-04-06 |
| DE2446992A1 (de) | 1976-04-15 |
| BE834120A (fr) | 1976-02-02 |
| FR2286809B1 (enExample) | 1980-09-12 |
| JPS5186429A (en) | 1976-07-29 |
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