JPS6330292B2 - - Google Patents
Info
- Publication number
- JPS6330292B2 JPS6330292B2 JP56180706A JP18070681A JPS6330292B2 JP S6330292 B2 JPS6330292 B2 JP S6330292B2 JP 56180706 A JP56180706 A JP 56180706A JP 18070681 A JP18070681 A JP 18070681A JP S6330292 B2 JPS6330292 B2 JP S6330292B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- reaction
- alkylbenzene
- silica gel
- chloroalkylbenzene
- 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
Links
- 239000003054 catalyst Substances 0.000 claims description 18
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000000741 silica gel Substances 0.000 claims description 5
- 229910002027 silica gel Inorganic materials 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 9
- RNEMUWDQJSRDMQ-UHFFFAOYSA-N 1-chloro-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1Cl RNEMUWDQJSRDMQ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- FHBSIIZALGOVLM-UHFFFAOYSA-N 1-chloro-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(Cl)C=C1 FHBSIIZALGOVLM-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000012320 chlorinating reagent Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- -1 thianthrene compound Chemical class 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 1
- KLGQWSOYKYFBTR-UHFFFAOYSA-N 2-nitrobenzamide Chemical group NC(=O)C1=CC=CC=C1[N+]([O-])=O KLGQWSOYKYFBTR-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229940065287 selenium compound Drugs 0.000 description 1
- 150000003343 selenium compounds Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56180706A JPS5883638A (ja) | 1981-11-11 | 1981-11-11 | アルキルベンゼン核塩素化物の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56180706A JPS5883638A (ja) | 1981-11-11 | 1981-11-11 | アルキルベンゼン核塩素化物の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5883638A JPS5883638A (ja) | 1983-05-19 |
| JPS6330292B2 true JPS6330292B2 (es) | 1988-06-17 |
Family
ID=16087884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56180706A Granted JPS5883638A (ja) | 1981-11-11 | 1981-11-11 | アルキルベンゼン核塩素化物の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5883638A (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998056498A1 (en) * | 1997-06-13 | 1998-12-17 | California Institute Of Technology | Porous silica having spatially organized organic functionalities |
-
1981
- 1981-11-11 JP JP56180706A patent/JPS5883638A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5883638A (ja) | 1983-05-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4025313B2 (ja) | アリール五フッ化イオウの調製方法 | |
| US5120883A (en) | Catalytic process for producing CCl3 CF3 | |
| KR970015581A (ko) | 치환된 티아졸 제조 방법 | |
| JPS6330292B2 (es) | ||
| EP0163230B1 (en) | Process for producing aromatic chlorine compounds | |
| EP0450584B1 (en) | Bromination method | |
| JP3557624B2 (ja) | ４，６−ジニトロハロベンゼンの製造方法 | |
| JP3918883B2 (ja) | ベンゾイルクロライド類の製造方法 | |
| JP2544804B2 (ja) | ジスルフイドの製造方法 | |
| JP3882855B2 (ja) | アルキルベンゾイルクロライドの製造法 | |
| JPS6327054B2 (es) | ||
| US4183873A (en) | Liquid phase fluorination process | |
| JP3857369B2 (ja) | 塩素化炭化水素の製造方法 | |
| JP3788482B2 (ja) | アルキルベンゾイルクロライドの製造方法 | |
| US4952719A (en) | Process for the preparation of halo aromatic compounds | |
| JPH04305544A (ja) | パラジクロロベンゼンの製法 | |
| JP3783733B2 (ja) | アルキルベンゾイルクロライドの製造法 | |
| JPH06184018A (ja) | 置換塩化クミルの製造方法 | |
| JPS60178829A (ja) | 含フツ素芳香族誘導体の製造法 | |
| JPH0153260B2 (es) | ||
| EP0752418B1 (en) | Method for preparing 4-alkyl-2-hydroxy-3,5-dichlorobenzene sulphonic acids | |
| JPH0322854B2 (es) | ||
| JP2658070B2 (ja) | 含フツ素アルカンの製造方法 | |
| JP3998075B2 (ja) | ポドフィロトキシンの脱メチル化法 | |
| JP2808695B2 (ja) | チオホスゲンの製法 |