DE69512480T2 - Verfahren zur selektiven Desulfonierung - Google Patents
Verfahren zur selektiven DesulfonierungInfo
- Publication number
- DE69512480T2 DE69512480T2 DE69512480T DE69512480T DE69512480T2 DE 69512480 T2 DE69512480 T2 DE 69512480T2 DE 69512480 T DE69512480 T DE 69512480T DE 69512480 T DE69512480 T DE 69512480T DE 69512480 T2 DE69512480 T2 DE 69512480T2
- Authority
- DE
- Germany
- Prior art keywords
- mixture
- desulfonation
- isomers
- temperature
- sulfuric acid
- 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 - Fee Related
Links
- 238000005869 desulfonation reaction Methods 0.000 title claims description 29
- 230000006326 desulfonation Effects 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 20
- 239000000203 mixture Substances 0.000 claims description 38
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 claims description 10
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003518 caustics Substances 0.000 claims description 5
- 230000029087 digestion Effects 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- UGHLEPMKNSFGCE-UHFFFAOYSA-N 2-ethylbenzenesulfonic acid Chemical class CCC1=CC=CC=C1S(O)(=O)=O UGHLEPMKNSFGCE-UHFFFAOYSA-N 0.000 claims description 2
- BRIXOPDYGQCZFO-UHFFFAOYSA-N 4-ethylphenylsulfonic acid Chemical compound CCC1=CC=C(S(O)(=O)=O)C=C1 BRIXOPDYGQCZFO-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000001816 cooling Methods 0.000 description 12
- 150000004996 alkyl benzenes Chemical class 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- 238000006277 sulfonation reaction Methods 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- VLJSLTNSFSOYQR-UHFFFAOYSA-N 3-propan-2-ylphenol Chemical compound CC(C)C1=CC=CC(O)=C1 VLJSLTNSFSOYQR-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 230000001934 delay Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- YXOGSLZKOVPUMH-UHFFFAOYSA-N ethene;phenol Chemical class C=C.OC1=CC=CC=C1 YXOGSLZKOVPUMH-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 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
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of SO3H groups or a derivative thereof
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 |
|---|---|---|---|
| JP6176550A JPH0840960A (ja) | 1994-07-28 | 1994-07-28 | 選択的脱スルホン化法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69512480D1 DE69512480D1 (de) | 1999-11-04 |
| DE69512480T2 true DE69512480T2 (de) | 2000-04-13 |
Family
ID=16015549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69512480T Expired - Fee Related DE69512480T2 (de) | 1994-07-28 | 1995-07-19 | Verfahren zur selektiven Desulfonierung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5741954A (enExample) |
| EP (1) | EP0694516B1 (enExample) |
| JP (1) | JPH0840960A (enExample) |
| CZ (1) | CZ286796B6 (enExample) |
| DE (1) | DE69512480T2 (enExample) |
| ES (1) | ES2136775T3 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2956960B2 (ja) * | 1996-10-24 | 1999-10-04 | 田岡化学工業株式会社 | ｍ−ヒドロキシアルキルベンゼンの製造方法 |
| WO2016187678A1 (en) | 2015-05-28 | 2016-12-01 | Katholieke Universiteit Leuven | Production of 3-alkylphenols and uses thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7314330A (enExample) | 1973-02-21 | 1974-08-23 | ||
| DE3262826D1 (en) * | 1981-11-27 | 1985-05-02 | Taoka Chemical Co Ltd | Process for preparing m-alkylhydroxybenzene |
| JPS5976033A (ja) | 1982-10-22 | 1984-04-28 | Taoka Chem Co Ltd | 高純度ｍ−アルキルヒドロキシベンゼンの製造方法 |
| JPH0229057B2 (ja) * | 1982-12-14 | 1990-06-27 | Taoka Chemical Co Ltd | Mmarukiruhidorokishibenzennoseizohoho |
-
1994
- 1994-07-28 JP JP6176550A patent/JPH0840960A/ja active Pending
-
1995
- 1995-07-19 DE DE69512480T patent/DE69512480T2/de not_active Expired - Fee Related
- 1995-07-19 ES ES95111325T patent/ES2136775T3/es not_active Expired - Lifetime
- 1995-07-19 US US08/504,161 patent/US5741954A/en not_active Expired - Fee Related
- 1995-07-19 EP EP95111325A patent/EP0694516B1/en not_active Expired - Lifetime
- 1995-07-27 CZ CZ19951948A patent/CZ286796B6/cs not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CZ194895A3 (en) | 1996-02-14 |
| JPH0840960A (ja) | 1996-02-13 |
| US5741954A (en) | 1998-04-21 |
| DE69512480D1 (de) | 1999-11-04 |
| ES2136775T3 (es) | 1999-12-01 |
| EP0694516A2 (en) | 1996-01-31 |
| EP0694516B1 (en) | 1999-09-29 |
| CZ286796B6 (en) | 2000-07-12 |
| EP0694516A3 (enExample) | 1996-02-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: KEMIRA FINE CHEMICALS OY, HELSINKI, FI |
|
| 8339 | Ceased/non-payment of the annual fee |