JPS6157536A - ２−ニトロ−４，６−ジクロル−５−エチルフエノ−ルの製造法 - Google Patents
２−ニトロ−４，６−ジクロル−５−エチルフエノ−ルの製造法Info
- Publication number
- JPS6157536A JPS6157536A JP17903284A JP17903284A JPS6157536A JP S6157536 A JPS6157536 A JP S6157536A JP 17903284 A JP17903284 A JP 17903284A JP 17903284 A JP17903284 A JP 17903284A JP S6157536 A JPS6157536 A JP S6157536A
- Authority
- JP
- Japan
- Prior art keywords
- ethylphenol
- dichloro
- give
- sulfuric acid
- nitro group
- 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
- YTVCECQSAPGJBB-UHFFFAOYSA-N 2,4-dichloro-3-ethyl-6-nitrophenol Chemical compound CCC1=C(Cl)C=C([N+]([O-])=O)C(O)=C1Cl YTVCECQSAPGJBB-UHFFFAOYSA-N 0.000 title claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 18
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 12
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 8
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract 3
- DVKVZPIRWWREJC-UHFFFAOYSA-N 4-chloro-3-ethylphenol Chemical compound CCC1=CC(O)=CC=C1Cl DVKVZPIRWWREJC-UHFFFAOYSA-N 0.000 claims abstract 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 10
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 7
- 150000008282 halocarbons Chemical class 0.000 claims description 7
- RTTKBGCGHTVPGS-UHFFFAOYSA-N 3,5-dichloro-4-ethyl-2-hydroxybenzenesulfonic acid Chemical compound CCC1=C(Cl)C=C(S(O)(=O)=O)C(O)=C1Cl RTTKBGCGHTVPGS-UHFFFAOYSA-N 0.000 claims 1
- AHUIQYHFLOYDGC-UHFFFAOYSA-N 4-ethyl-2-hydroxybenzenesulfonic acid Chemical compound CCC1=CC=C(S(O)(=O)=O)C(O)=C1 AHUIQYHFLOYDGC-UHFFFAOYSA-N 0.000 claims 1
- MFTBMHRGXBBBOI-UHFFFAOYSA-N 5-chloro-4-ethyl-2-hydroxybenzenesulfonic acid Chemical compound CCC1=CC(O)=C(S(O)(=O)=O)C=C1Cl MFTBMHRGXBBBOI-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 14
- 238000006277 sulfonation reaction Methods 0.000 abstract description 6
- 239000000543 intermediate Substances 0.000 abstract description 5
- 239000007858 starting material Substances 0.000 abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- XZZITYVICUAZNB-UHFFFAOYSA-N (3,5-dichloro-4-ethyl-2-hydroxyphenyl)azanium;chloride Chemical compound Cl.CCC1=C(Cl)C=C(N)C(O)=C1Cl XZZITYVICUAZNB-UHFFFAOYSA-N 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 150000005826 halohydrocarbons Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 125000001174 sulfone group Chemical group 0.000 description 7
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000005660 chlorination reaction Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000006396 nitration reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- -1 sulfone compound Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 230000021736 acetylation Effects 0.000 description 3
- 238000006640 acetylation reaction Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000011946 reduction process Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- MCTXOQDMAMSOCX-UHFFFAOYSA-N 2-ethylphenol;hydrochloride Chemical compound Cl.CCC1=CC=CC=C1O MCTXOQDMAMSOCX-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17903284A JPS6157536A (ja) | 1984-08-28 | 1984-08-28 | ２−ニトロ−４，６−ジクロル−５−エチルフエノ−ルの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17903284A JPS6157536A (ja) | 1984-08-28 | 1984-08-28 | ２−ニトロ−４，６−ジクロル−５−エチルフエノ−ルの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6157536A true JPS6157536A (ja) | 1986-03-24 |
| JPH0354930B2 JPH0354930B2 (en, 2012) | 1991-08-21 |
Family
ID=16058916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17903284A Granted JPS6157536A (ja) | 1984-08-28 | 1984-08-28 | ２−ニトロ−４，６−ジクロル−５−エチルフエノ−ルの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6157536A (en, 2012) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63303958A (ja) * | 1987-06-04 | 1988-12-12 | Sumitomo Chem Co Ltd | ２−アミノ−４，６−ジクロル−５−アルキルフェノ−ルの製造法 |
| US5136109A (en) * | 1990-08-28 | 1992-08-04 | Taoka Chemical Company, Ltd. | Process for preparing 2,4-dichloro-3-alkyl-6-nitrophenols |
| EP0752418A1 (en) * | 1995-07-05 | 1997-01-08 | Kemira Agro Oy | Method for preparing 4-alkyl-2-hydroxy-3, 5-dichlorobenzene sulphonic acids |
| CN106631920A (zh) * | 2016-11-17 | 2017-05-10 | 贵州大学 | 一种2‑羟基‑4‑甲基苯磺酸的制备方法 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5268854B2 (ja) | 2009-10-09 | 2013-08-21 | 花王株式会社 | 柔軟性シートの製造方法 |
| JP6062199B2 (ja) | 2012-09-28 | 2017-01-18 | ユニ・チャーム株式会社 | 吸収性物品 |
-
1984
- 1984-08-28 JP JP17903284A patent/JPS6157536A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63303958A (ja) * | 1987-06-04 | 1988-12-12 | Sumitomo Chem Co Ltd | ２−アミノ−４，６−ジクロル−５−アルキルフェノ−ルの製造法 |
| US5136109A (en) * | 1990-08-28 | 1992-08-04 | Taoka Chemical Company, Ltd. | Process for preparing 2,4-dichloro-3-alkyl-6-nitrophenols |
| EP0752418A1 (en) * | 1995-07-05 | 1997-01-08 | Kemira Agro Oy | Method for preparing 4-alkyl-2-hydroxy-3, 5-dichlorobenzene sulphonic acids |
| CN106631920A (zh) * | 2016-11-17 | 2017-05-10 | 贵州大学 | 一种2‑羟基‑4‑甲基苯磺酸的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0354930B2 (en, 2012) | 1991-08-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |