DE2205227A1 - Verfahren zur isolierung von arylhydroxy-verbindungen - Google Patents
Verfahren zur isolierung von arylhydroxy-verbindungenInfo
- Publication number
- DE2205227A1 DE2205227A1 DE2205227A DE2205227A DE2205227A1 DE 2205227 A1 DE2205227 A1 DE 2205227A1 DE 2205227 A DE2205227 A DE 2205227A DE 2205227 A DE2205227 A DE 2205227A DE 2205227 A1 DE2205227 A1 DE 2205227A1
- Authority
- DE
- Germany
- Prior art keywords
- alkali
- extraction
- naphthol
- ketone
- water
- 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
- 238000000034 method Methods 0.000 title claims description 34
- 150000001875 compounds Chemical class 0.000 title claims description 12
- 238000000605 extraction Methods 0.000 claims description 37
- 239000000243 solution Substances 0.000 claims description 25
- 239000003513 alkali Substances 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 150000002576 ketones Chemical class 0.000 claims description 20
- 238000009835 boiling Methods 0.000 claims description 15
- 239000012074 organic phase Substances 0.000 claims description 14
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 11
- 239000008346 aqueous phase Substances 0.000 claims description 11
- -1 aryl hydroxide compound Chemical class 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 5
- PMPBFICDXLLSRM-UHFFFAOYSA-N 1-propan-2-ylnaphthalene Chemical compound C1=CC=C2C(C(C)C)=CC=CC2=C1 PMPBFICDXLLSRM-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 235000011121 sodium hydroxide Nutrition 0.000 description 11
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 8
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 239000012071 phase Substances 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 239000012670 alkaline solution Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 150000002440 hydroxy compounds Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 3
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-M naphthalen-1-olate Chemical compound C1=CC=C2C([O-])=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-M 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- AJXVJQAPXVDFBT-UHFFFAOYSA-M sodium;naphthalen-2-olate Chemical compound [Na+].C1=CC=CC2=CC([O-])=CC=C21 AJXVJQAPXVDFBT-UHFFFAOYSA-M 0.000 description 3
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000000378 dietary effect Effects 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000004780 naphthols Chemical class 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 description 1
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical class CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 1
- WONRDHPFOHAWOG-UHFFFAOYSA-N 2-chloronaphthalen-1-ol Chemical class C1=CC=C2C(O)=C(Cl)C=CC2=C1 WONRDHPFOHAWOG-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical class OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 229910002056 binary alloy Inorganic materials 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000004124 hock Anatomy 0.000 description 1
- 125000003010 ionic group Chemical group 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
- 239000000155 melt Substances 0.000 description 1
- CRVVHBFLWWQMPT-UHFFFAOYSA-N naphthalene-1-sulfonic acid;sodium Chemical compound [Na].C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 CRVVHBFLWWQMPT-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- ZBNNKSSSCSTNNK-UHFFFAOYSA-M sodium;naphthalen-1-olate Chemical compound [Na+].C1=CC=C2C([O-])=CC=CC2=C1 ZBNNKSSSCSTNNK-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure 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)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE794992D BE794992A (fr) | 1972-02-04 | Procede d'isolement de composes aryl-hydroxyliques | |
| DE2205227A DE2205227A1 (de) | 1972-02-04 | 1972-02-04 | Verfahren zur isolierung von arylhydroxy-verbindungen |
| CA162,939A CA1004690A (en) | 1972-02-04 | 1973-01-30 | Process for isolating arylhydroxy compounds |
| NL7301297A NL7301297A (enExample) | 1972-02-04 | 1973-01-30 | |
| US328023A US3894095A (en) | 1972-02-04 | 1973-01-30 | Process for isolating arylhydroxy compounds |
| CH142973A CH589019A5 (enExample) | 1972-02-04 | 1973-02-01 | |
| DD168637A DD106160A5 (enExample) | 1972-02-04 | 1973-02-02 | |
| IT19987/73A IT978772B (it) | 1972-02-04 | 1973-02-02 | Procedimento per l isolamento di arilidrossicomposti |
| SU1881112A SU524512A3 (ru) | 1972-02-04 | 1973-02-02 | Способ выделени арилгидроксилсоединений |
| JP48013003A JPS4885544A (enExample) | 1972-02-04 | 1973-02-02 | |
| GB560173A GB1425226A (en) | 1972-02-04 | 1973-02-05 | Isolation of monohydroxyaryl compounds |
| FR7303922A FR2170260B1 (enExample) | 1972-02-04 | 1973-02-05 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2205227A DE2205227A1 (de) | 1972-02-04 | 1972-02-04 | Verfahren zur isolierung von arylhydroxy-verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2205227A1 true DE2205227A1 (de) | 1973-08-16 |
Family
ID=5834993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2205227A Pending DE2205227A1 (de) | 1972-02-04 | 1972-02-04 | Verfahren zur isolierung von arylhydroxy-verbindungen |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3894095A (enExample) |
| JP (1) | JPS4885544A (enExample) |
| BE (1) | BE794992A (enExample) |
| CA (1) | CA1004690A (enExample) |
| CH (1) | CH589019A5 (enExample) |
| DD (1) | DD106160A5 (enExample) |
| DE (1) | DE2205227A1 (enExample) |
| FR (1) | FR2170260B1 (enExample) |
| GB (1) | GB1425226A (enExample) |
| IT (1) | IT978772B (enExample) |
| NL (1) | NL7301297A (enExample) |
| SU (1) | SU524512A3 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5517304A (en) * | 1978-07-18 | 1980-02-06 | Hodogaya Chem Co Ltd | Preparation of 4, 4'-dihydroxybiphenyl |
| US4400553A (en) * | 1981-06-24 | 1983-08-23 | General Electric Company | Recovery of BPA and phenol from aqueous effluent streams |
| US4374283A (en) * | 1981-06-25 | 1983-02-15 | General Electric Company | Purification of aqueous effluent streams containing BPA and phenol |
| US4547596A (en) * | 1983-03-30 | 1985-10-15 | General Electric Company | Separation and recovery of alkylated phenols |
| US4705902A (en) * | 1985-10-03 | 1987-11-10 | Rohm And Haas Company | DDTR-free 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol |
| GB0016336D0 (en) * | 2000-07-03 | 2000-08-23 | Zeneca Ltd | Chemical process |
| GB0016338D0 (en) * | 2000-07-03 | 2000-08-23 | Zeneca Ltd | Chemical process |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1314138A (en) * | 1919-08-26 | Nathan goodman and benjamin grubman | ||
| US1956570A (en) * | 1931-08-15 | 1934-05-01 | Rhone Poulenc Sa | Process of recovering resorcinol |
| US1991329A (en) * | 1932-05-02 | 1935-02-12 | Dow Chemical Co | Alkali-metal trichlorophenolates |
| US2137587A (en) * | 1937-05-13 | 1938-11-22 | Dow Chemical Co | Separation of phenols |
| US2334488A (en) * | 1941-06-18 | 1943-11-16 | Allied Chem & Dye Corp | Manufacture of aromatic hydroxy compounds |
-
0
- BE BE794992D patent/BE794992A/xx unknown
-
1972
- 1972-02-04 DE DE2205227A patent/DE2205227A1/de active Pending
-
1973
- 1973-01-30 US US328023A patent/US3894095A/en not_active Expired - Lifetime
- 1973-01-30 CA CA162,939A patent/CA1004690A/en not_active Expired
- 1973-01-30 NL NL7301297A patent/NL7301297A/xx not_active Application Discontinuation
- 1973-02-01 CH CH142973A patent/CH589019A5/xx not_active IP Right Cessation
- 1973-02-02 JP JP48013003A patent/JPS4885544A/ja active Pending
- 1973-02-02 IT IT19987/73A patent/IT978772B/it active
- 1973-02-02 DD DD168637A patent/DD106160A5/xx unknown
- 1973-02-02 SU SU1881112A patent/SU524512A3/ru active
- 1973-02-05 FR FR7303922A patent/FR2170260B1/fr not_active Expired
- 1973-02-05 GB GB560173A patent/GB1425226A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA1004690A (en) | 1977-02-01 |
| JPS4885544A (enExample) | 1973-11-13 |
| NL7301297A (enExample) | 1973-08-07 |
| DD106160A5 (enExample) | 1974-06-05 |
| BE794992A (fr) | 1973-08-06 |
| CH589019A5 (enExample) | 1977-06-30 |
| IT978772B (it) | 1974-09-20 |
| FR2170260B1 (enExample) | 1976-11-05 |
| SU524512A3 (ru) | 1976-08-05 |
| US3894095A (en) | 1975-07-08 |
| FR2170260A1 (enExample) | 1973-09-14 |
| GB1425226A (en) | 1976-02-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHN | Withdrawal |