JPS61236735A - ２，６−ジクロロトルエンの選択的分離法 - Google Patents
２，６−ジクロロトルエンの選択的分離法Info
- Publication number
- JPS61236735A JPS61236735A JP60078445A JP7844585A JPS61236735A JP S61236735 A JPS61236735 A JP S61236735A JP 60078445 A JP60078445 A JP 60078445A JP 7844585 A JP7844585 A JP 7844585A JP S61236735 A JPS61236735 A JP S61236735A
- Authority
- JP
- Japan
- Prior art keywords
- dct
- zsm
- zeolite
- adsorption
- isomer mixture
- 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
- DMEDNTFWIHCBRK-UHFFFAOYSA-N 1,3-dichloro-2-methylbenzene Chemical compound CC1=C(Cl)C=CC=C1Cl DMEDNTFWIHCBRK-UHFFFAOYSA-N 0.000 title claims 3
- RYMMNSVHOKXTNN-UHFFFAOYSA-N 1,3-dichloro-5-methyl-benzene Natural products CC1=CC(Cl)=CC(Cl)=C1 RYMMNSVHOKXTNN-UHFFFAOYSA-N 0.000 title claims 3
- 238000000926 separation method Methods 0.000 title description 18
- 239000000203 mixture Substances 0.000 claims description 39
- 239000010457 zeolite Substances 0.000 claims description 31
- 229910021536 Zeolite Inorganic materials 0.000 claims description 30
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 28
- 239000003463 adsorbent Substances 0.000 claims description 11
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical class ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 description 19
- 239000007788 liquid Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001768 cations Chemical class 0.000 description 7
- 238000003795 desorption Methods 0.000 description 7
- 238000005342 ion exchange Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000011437 continuous method Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- -1 protons Chemical class 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
- FUNUTBJJKQIVSY-UHFFFAOYSA-N 2,4-Dichlorotoluene Chemical compound CC1=CC=C(Cl)C=C1Cl FUNUTBJJKQIVSY-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 241001061127 Thione Species 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006326 desulfonation Effects 0.000 description 1
- 238000005869 desulfonation reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000012013 faujasite Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/389—Separation; Purification; Stabilisation; Use of additives by adsorption on solids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60078445A JPS61236735A (ja) | 1985-04-15 | 1985-04-15 | ２，６−ジクロロトルエンの選択的分離法 |
| EP86104983A EP0199212B1 (en) | 1985-04-15 | 1986-04-11 | Method for selective separation of 2,6-dichlorotoluene |
| DE8686104983T DE3660378D1 (en) | 1985-04-15 | 1986-04-11 | Method for selective separation of 2,6-dichlorotoluene |
| CA000506615A CA1274253A (en) | 1985-04-15 | 1986-04-14 | Method for selective separation of 2,6- dichlorotoluene |
| US07/060,862 US4831198A (en) | 1985-04-15 | 1987-06-12 | Method for adsorptive separation of dichlorotoluenes |
| US07/062,385 US4777306A (en) | 1985-04-15 | 1987-06-15 | Method for selective separation of 2,6-dichlorotoluene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60078445A JPS61236735A (ja) | 1985-04-15 | 1985-04-15 | ２，６−ジクロロトルエンの選択的分離法 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21125789A Division JPH02131440A (ja) | 1989-08-18 | 1989-08-18 | ２，６―ジクロロトルエンの選択的分離法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61236735A true JPS61236735A (ja) | 1986-10-22 |
| JPH0247970B2 JPH0247970B2 (en]) | 1990-10-23 |
Family
ID=13662238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60078445A Granted JPS61236735A (ja) | 1985-04-15 | 1985-04-15 | ２，６−ジクロロトルエンの選択的分離法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4777306A (en]) |
| EP (1) | EP0199212B1 (en]) |
| JP (1) | JPS61236735A (en]) |
| CA (1) | CA1274253A (en]) |
| DE (1) | DE3660378D1 (en]) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61236735A (ja) * | 1985-04-15 | 1986-10-22 | Hodogaya Chem Co Ltd | ２，６−ジクロロトルエンの選択的分離法 |
| US4831198A (en) * | 1985-04-15 | 1989-05-16 | Hodogaya Chemical Co., Ltd. | Method for adsorptive separation of dichlorotoluenes |
| EP0249883B1 (en) * | 1986-06-18 | 1992-09-16 | Hodogaya Chemical Company, Limited | Method for adsorptive separation of dichlorotoluenes |
| JPS63196530A (ja) * | 1987-02-10 | 1988-08-15 | Hodogaya Chem Co Ltd | ｍ−ジクロロベンゼンの選択的分離法 |
| DE68902666T2 (de) * | 1988-02-26 | 1996-05-02 | Toray Industries | Verfahren zur Abtrennung von halogenierten Benzolabkömmlingen. |
| US4922040A (en) * | 1988-12-28 | 1990-05-01 | Uop | Process for extracting 2,5-dichlorotoluene from isomer mixtures with sodium-L zeolite adsorbents |
| JPH046977U (en]) * | 1990-05-07 | 1992-01-22 | ||
| JPH0656713A (ja) * | 1991-04-27 | 1994-03-01 | Hoechst Ag | クロロフルオロ炭化水素の精製方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61112034A (ja) * | 1984-10-26 | 1986-05-30 | エルフ アトケム ソシエテ アノニム | ゼオライトでの吸着による異性体ジクロロトルエンの分離法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2958708A (en) * | 1959-03-23 | 1960-11-01 | Union Oil Co | Separation of isomeric halogenated aromatic compounds |
| DE2804203C3 (de) * | 1978-02-01 | 1980-09-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur Trennung von isomeren Dichlortoluolen |
| US4453029A (en) * | 1979-12-19 | 1984-06-05 | Mobil Oil Corporation | Selective sorption by zeolites |
| JPS59199642A (ja) * | 1983-04-28 | 1984-11-12 | Toray Ind Inc | ２，６−ジクロルトルエンの分離方法 |
| JPS61236735A (ja) * | 1985-04-15 | 1986-10-22 | Hodogaya Chem Co Ltd | ２，６−ジクロロトルエンの選択的分離法 |
-
1985
- 1985-04-15 JP JP60078445A patent/JPS61236735A/ja active Granted
-
1986
- 1986-04-11 EP EP86104983A patent/EP0199212B1/en not_active Expired
- 1986-04-11 DE DE8686104983T patent/DE3660378D1/de not_active Expired
- 1986-04-14 CA CA000506615A patent/CA1274253A/en not_active Expired
-
1987
- 1987-06-15 US US07/062,385 patent/US4777306A/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61112034A (ja) * | 1984-10-26 | 1986-05-30 | エルフ アトケム ソシエテ アノニム | ゼオライトでの吸着による異性体ジクロロトルエンの分離法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0247970B2 (en]) | 1990-10-23 |
| EP0199212B1 (en) | 1988-07-13 |
| US4777306A (en) | 1988-10-11 |
| EP0199212A1 (en) | 1986-10-29 |
| DE3660378D1 (en) | 1988-08-18 |
| CA1274253A (en) | 1990-09-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS5838224A (ja) | ｐ‐クロロトルエンの製造方法 | |
| EP0246673A1 (en) | Process for separating a chlorotoluene isomer | |
| JPS61236735A (ja) | ２，６−ジクロロトルエンの選択的分離法 | |
| US4336410A (en) | Process for absorptive separation of cyclohexene | |
| EP0334025B2 (en) | Process for the separation of halogenated benzene derivatives | |
| EP0046068A1 (en) | Process for separating a mononuclear halogenated toluene isomer | |
| EP0249883B1 (en) | Method for adsorptive separation of dichlorotoluenes | |
| EP0322869B1 (en) | Process for separating dichlorocumene isomer | |
| US4831198A (en) | Method for adsorptive separation of dichlorotoluenes | |
| EP0278680B1 (en) | Method for selective isolation of m-dichlorobenzene | |
| JP2516339B2 (ja) | ジクロロトルエンの吸着分離方法 | |
| US4798913A (en) | Method for separating a trihalogenobenzene isomer | |
| US5143685A (en) | Process for purification of ortho-chlorotoluene | |
| US4814526A (en) | Selective adsorption/separation of diiodonaphthalenes | |
| JPS63264537A (ja) | ２，６−ジクロロトルエンの選択的分離法 | |
| JP3092218B2 (ja) | １，３，５−トリクロルベンゼンの製造方法 | |
| JPH02131440A (ja) | ２，６―ジクロロトルエンの選択的分離法 | |
| JPH07566B2 (ja) | ジクロロトルエンの選択的分離法 | |
| JPS61254535A (ja) | ジクロロトルエンの脱着方法 | |
| JPS6293243A (ja) | ２，６−ジクロロトルエンの吸着分離法 | |
| JP2576725B2 (ja) | ２，４−ジクロロトルエンの分離方法 | |
| JPS62149636A (ja) | ジクロロトルエンの選択的分離法 | |
| JP2004238391A (ja) | ジクロロフェノール分離方法 | |
| JPH0665114A (ja) | ２，６−ジメチルナフタレンの分離方法 | |
| JPH01163140A (ja) | トリハロゲノベンゼン異性体の分離方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |