JPS5976033A - 高純度ｍ−アルキルヒドロキシベンゼンの製造方法 - Google Patents
高純度ｍ−アルキルヒドロキシベンゼンの製造方法Info
- Publication number
- JPS5976033A JPS5976033A JP18661382A JP18661382A JPS5976033A JP S5976033 A JPS5976033 A JP S5976033A JP 18661382 A JP18661382 A JP 18661382A JP 18661382 A JP18661382 A JP 18661382A JP S5976033 A JPS5976033 A JP S5976033A
- Authority
- JP
- Japan
- Prior art keywords
- temperature
- hydrolysis
- alkylbenzene
- water
- 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.)
- Granted
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 28
- 230000007062 hydrolysis Effects 0.000 claims abstract description 24
- 150000004996 alkyl benzenes Chemical class 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 239000000376 reactant Substances 0.000 claims abstract description 4
- 239000003518 caustics Substances 0.000 claims abstract description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 17
- 238000000034 method Methods 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 6
- 239000003513 alkali Substances 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 10
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- BRIXOPDYGQCZFO-UHFFFAOYSA-N 4-ethylphenylsulfonic acid Chemical compound CCC1=CC=C(S(O)(=O)=O)C=C1 BRIXOPDYGQCZFO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- -1 alkylbenzene sulfonic acids Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- QPVRKFOKCKORDP-UHFFFAOYSA-N 1,3-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC(C)(O)CC=C1 QPVRKFOKCKORDP-UHFFFAOYSA-N 0.000 description 1
- JDQDSEVNMTYMOC-UHFFFAOYSA-N 3-methylbenzenesulfonic acid Chemical compound CC1=CC=CC(S(O)(=O)=O)=C1 JDQDSEVNMTYMOC-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18661382A JPS5976033A (ja) | 1982-10-22 | 1982-10-22 | 高純度ｍ−アルキルヒドロキシベンゼンの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18661382A JPS5976033A (ja) | 1982-10-22 | 1982-10-22 | 高純度ｍ−アルキルヒドロキシベンゼンの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5976033A true JPS5976033A (ja) | 1984-04-28 |
| JPH029012B2 JPH029012B2 (enrdf_load_stackoverflow) | 1990-02-28 |
Family
ID=16191636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18661382A Granted JPS5976033A (ja) | 1982-10-22 | 1982-10-22 | 高純度ｍ−アルキルヒドロキシベンゼンの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5976033A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0694516A2 (en) | 1994-07-28 | 1996-01-31 | Kemira Oyj | Process of selective desulfonation |
| CN105906481A (zh) * | 2016-05-12 | 2016-08-31 | 金能科技股份有限公司 | 一种对甲苯酚的制备方法及设备 |
| WO2016187678A1 (en) | 2015-05-28 | 2016-12-01 | Katholieke Universiteit Leuven | Production of 3-alkylphenols and uses thereof |
-
1982
- 1982-10-22 JP JP18661382A patent/JPS5976033A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0694516A2 (en) | 1994-07-28 | 1996-01-31 | Kemira Oyj | Process of selective desulfonation |
| WO2016187678A1 (en) | 2015-05-28 | 2016-12-01 | Katholieke Universiteit Leuven | Production of 3-alkylphenols and uses thereof |
| CN105906481A (zh) * | 2016-05-12 | 2016-08-31 | 金能科技股份有限公司 | 一种对甲苯酚的制备方法及设备 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH029012B2 (enrdf_load_stackoverflow) | 1990-02-28 |
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