JPH0112733B2 - - Google Patents
Info
- Publication number
- JPH0112733B2 JPH0112733B2 JP10288782A JP10288782A JPH0112733B2 JP H0112733 B2 JPH0112733 B2 JP H0112733B2 JP 10288782 A JP10288782 A JP 10288782A JP 10288782 A JP10288782 A JP 10288782A JP H0112733 B2 JPH0112733 B2 JP H0112733B2
- Authority
- JP
- Japan
- Prior art keywords
- adsorption
- tcb
- adsorbent
- trihalogenated
- present
- 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
- 239000000203 mixture Substances 0.000 claims description 21
- 239000010457 zeolite Substances 0.000 claims description 15
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 13
- 229910021536 Zeolite Inorganic materials 0.000 claims description 12
- 239000003463 adsorbent Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 238000001179 sorption measurement Methods 0.000 description 22
- 150000001555 benzenes Chemical class 0.000 description 16
- PBKONEOXTCPAFI-UHFFFAOYSA-N TCB Natural products ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- 239000007791 liquid phase Substances 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012013 faujasite Substances 0.000 description 3
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- BDMRCAWYRXJKLK-UHFFFAOYSA-N 1,2-dibromo-3-chlorobenzene Chemical compound ClC1=CC=CC(Br)=C1Br BDMRCAWYRXJKLK-UHFFFAOYSA-N 0.000 description 1
- CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 description 1
- -1 1,3,5-trisubstituted benzenes Chemical class 0.000 description 1
- FNKCOUREFBNNHG-UHFFFAOYSA-N 1,3-dibromo-5-chlorobenzene Chemical compound ClC1=CC(Br)=CC(Br)=C1 FNKCOUREFBNNHG-UHFFFAOYSA-N 0.000 description 1
- RNABGKOKSBUFHW-UHFFFAOYSA-N 1,3-dichloro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(Cl)=C1 RNABGKOKSBUFHW-UHFFFAOYSA-N 0.000 description 1
- HVKCZUVMQPUWSX-UHFFFAOYSA-N 1-bromo-2,3-dichlorobenzene Chemical compound ClC1=CC=CC(Br)=C1Cl HVKCZUVMQPUWSX-UHFFFAOYSA-N 0.000 description 1
- QBELEDRHMPMKHP-UHFFFAOYSA-N 1-bromo-2-chlorobenzene Chemical compound ClC1=CC=CC=C1Br QBELEDRHMPMKHP-UHFFFAOYSA-N 0.000 description 1
- DZHFFMWJXJBBRG-UHFFFAOYSA-N 1-bromo-3,5-dichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Br)=C1 DZHFFMWJXJBBRG-UHFFFAOYSA-N 0.000 description 1
- NVLHGZIXTRYOKT-UHFFFAOYSA-N 1-chloro-2,3-dimethylbenzene Chemical group CC1=CC=CC(Cl)=C1C NVLHGZIXTRYOKT-UHFFFAOYSA-N 0.000 description 1
- GFJKASVFAWFUNI-UHFFFAOYSA-N 1-chloro-3,5-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC([N+]([O-])=O)=C1 GFJKASVFAWFUNI-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 238000010586 diagram 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
- 239000002360 explosive Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10288782A JPS58219131A (ja) | 1982-06-15 | 1982-06-15 | トリハロゲン化ベンゼン異性体の分離方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10288782A JPS58219131A (ja) | 1982-06-15 | 1982-06-15 | トリハロゲン化ベンゼン異性体の分離方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58219131A JPS58219131A (ja) | 1983-12-20 |
| JPH0112733B2 true JPH0112733B2 (ko) | 1989-03-02 |
Family
ID=14339369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10288782A Granted JPS58219131A (ja) | 1982-06-15 | 1982-06-15 | トリハロゲン化ベンゼン異性体の分離方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58219131A (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62292736A (ja) * | 1986-06-13 | 1987-12-19 | Toray Ind Inc | モノクロロモノフルオロベンゾトリフルオライド異性体の分離方法 |
| JP2516340B2 (ja) * | 1986-07-18 | 1996-07-24 | 保土谷化学工業株式会社 | トリハロゲノベンゼン異性体の分離方法 |
-
1982
- 1982-06-15 JP JP10288782A patent/JPS58219131A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58219131A (ja) | 1983-12-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0145457B2 (ko) | ||
| JPS6323976B2 (ko) | ||
| JPH0112733B2 (ko) | ||
| KR920003117B1 (ko) | 디클로로큐멘 이성질체의 분리방법 | |
| US4714783A (en) | Separation of nitrobenzaldehyde isomers | |
| JPS6014005B2 (ja) | ルビジウム―ｘシーブを用いるｃ↓８芳香族系混合物からのエチルベンゼンの分離および回収 | |
| JPS6324981B2 (ko) | ||
| JP2678205B2 (ja) | ２，６―及び２，５―ジクロルトルエンの分離方法 | |
| US5143685A (en) | Process for purification of ortho-chlorotoluene | |
| JP2576725B2 (ja) | ２，４−ジクロロトルエンの分離方法 | |
| JP3151931B2 (ja) | ２−クロロ−４−フルオロトルエンの分離方法 | |
| JPS6324495B2 (ko) | ||
| JPS64371B2 (ko) | ||
| JPH09188638A (ja) | ジハロゲン化ベンゼン異性体の分離方法 | |
| JPH0413639A (ja) | ２，４―ジクロロフルオロベンゼンの分離方法 | |
| JPH0112735B2 (ko) | ||
| JPS6364412B2 (ko) | ||
| JPH0140016B2 (ko) | ||
| JPH0112734B2 (ko) | ||
| JPH04330025A (ja) | ジクロロベンゼン異性体の分離方法 | |
| JP3807061B2 (ja) | ハロゲン化エチルベンゼン異性体の分離方法 | |
| JPH0665114A (ja) | ２，６−ジメチルナフタレンの分離方法 | |
| EP0181106B1 (en) | Separation of ortho-nitrotoluene | |
| JPH0437063B2 (ko) | ||
| US4922040A (en) | Process for extracting 2,5-dichlorotoluene from isomer mixtures with sodium-L zeolite adsorbents |