DE2327216A1 - Verfahren zur reinigung von phenol - Google Patents
Verfahren zur reinigung von phenolInfo
- Publication number
- DE2327216A1 DE2327216A1 DE2327216A DE2327216A DE2327216A1 DE 2327216 A1 DE2327216 A1 DE 2327216A1 DE 2327216 A DE2327216 A DE 2327216A DE 2327216 A DE2327216 A DE 2327216A DE 2327216 A1 DE2327216 A1 DE 2327216A1
- Authority
- DE
- Germany
- Prior art keywords
- phenol
- impurities
- water
- distillation
- column
- 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.)
- Withdrawn
Links
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims description 82
- 238000000034 method Methods 0.000 title claims description 25
- 238000004140 cleaning Methods 0.000 title claims 2
- 239000012535 impurity Substances 0.000 claims description 57
- 238000004821 distillation Methods 0.000 claims description 49
- 238000009835 boiling Methods 0.000 claims description 36
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 35
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 34
- 238000000354 decomposition reaction Methods 0.000 claims description 25
- SHOJXDKTYKFBRD-UHFFFAOYSA-N 4-Methyl-3-penten-2-one, 9CI Chemical compound CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 claims description 19
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 15
- 238000003776 cleavage reaction Methods 0.000 claims description 12
- 230000007017 scission Effects 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 2
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 claims description 2
- 239000003344 environmental pollutant Substances 0.000 claims 1
- XDTRNDKYILNOAP-UHFFFAOYSA-N phenol;propan-2-one Chemical compound CC(C)=O.OC1=CC=CC=C1 XDTRNDKYILNOAP-UHFFFAOYSA-N 0.000 claims 1
- 231100000719 pollutant Toxicity 0.000 claims 1
- 239000000047 product Substances 0.000 description 29
- 238000005660 chlorination reaction Methods 0.000 description 6
- 238000006277 sulfonation reaction Methods 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000000895 extractive distillation Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- GBGPVUAOTCNZPT-UHFFFAOYSA-N 2-Methylcumarone Chemical compound C1=CC=C2OC(C)=CC2=C1 GBGPVUAOTCNZPT-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000009928 pasteurization Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002834 transmittance 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
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
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 |
|---|---|---|---|
| GB2559872A GB1394454A (en) | 1972-06-01 | 1972-06-01 | Process for the production of high-purity phenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2327216A1 true DE2327216A1 (de) | 1973-12-20 |
Family
ID=10230290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2327216A Withdrawn DE2327216A1 (de) | 1972-06-01 | 1973-05-28 | Verfahren zur reinigung von phenol |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS582931B2 (cs) |
| AR (1) | AR197813A1 (cs) |
| BE (1) | BE800342A (cs) |
| BR (1) | BR7304135D0 (cs) |
| CA (1) | CA989766A (cs) |
| DE (1) | DE2327216A1 (cs) |
| ES (1) | ES415422A1 (cs) |
| FR (1) | FR2186455B1 (cs) |
| GB (1) | GB1394454A (cs) |
| IT (1) | IT988825B (cs) |
| NL (1) | NL7307442A (cs) |
| NO (1) | NO141646C (cs) |
| SE (1) | SE401919B (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4832796A (en) * | 1987-07-16 | 1989-05-23 | General Electric Company | Process for purifying phenol |
| JP2015178476A (ja) * | 2014-03-19 | 2015-10-08 | 三菱化学株式会社 | フェノールの製造方法 |
-
1972
- 1972-06-01 GB GB2559872A patent/GB1394454A/en not_active Expired
-
1973
- 1973-05-28 SE SE7307543A patent/SE401919B/xx unknown
- 1973-05-28 DE DE2327216A patent/DE2327216A1/de not_active Withdrawn
- 1973-05-29 NL NL7307442A patent/NL7307442A/xx not_active Application Discontinuation
- 1973-05-30 BE BE131786A patent/BE800342A/xx unknown
- 1973-05-30 FR FR7319630A patent/FR2186455B1/fr not_active Expired
- 1973-05-30 IT IT24857/73A patent/IT988825B/it active
- 1973-05-30 AR AR248287A patent/AR197813A1/es active
- 1973-05-30 NO NO2259/73A patent/NO141646C/no unknown
- 1973-05-30 ES ES415422A patent/ES415422A1/es not_active Expired
- 1973-05-31 CA CA172,826A patent/CA989766A/en not_active Expired
- 1973-05-31 JP JP48060407A patent/JPS582931B2/ja not_active Expired
- 1973-06-01 BR BR4135/73A patent/BR7304135D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7307442A (cs) | 1973-12-04 |
| BR7304135D0 (pt) | 1974-07-18 |
| NO141646B (no) | 1980-01-07 |
| AR197813A1 (es) | 1974-05-10 |
| NO141646C (no) | 1980-04-16 |
| CA989766A (en) | 1976-05-25 |
| GB1394454A (en) | 1975-05-14 |
| SE401919B (sv) | 1978-06-05 |
| ES415422A1 (es) | 1976-02-16 |
| FR2186455A1 (cs) | 1974-01-11 |
| FR2186455B1 (cs) | 1977-04-29 |
| BE800342A (fr) | 1973-11-30 |
| JPS582931B2 (ja) | 1983-01-19 |
| JPS4948628A (cs) | 1974-05-11 |
| IT988825B (it) | 1975-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| OD | Request for examination | ||
| 8139 | Disposal/non-payment of the annual fee |