DE3486207T2 - Verfahren zur Abtrennung von 2-Chlor-m-xylol. - Google Patents
Verfahren zur Abtrennung von 2-Chlor-m-xylol.Info
- Publication number
- DE3486207T2 DE3486207T2 DE90202602T DE3486207T DE3486207T2 DE 3486207 T2 DE3486207 T2 DE 3486207T2 DE 90202602 T DE90202602 T DE 90202602T DE 3486207 T DE3486207 T DE 3486207T DE 3486207 T2 DE3486207 T2 DE 3486207T2
- Authority
- DE
- Germany
- Prior art keywords
- adsorbent
- substituted benzene
- benzene compound
- xylene
- chloro
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims description 22
- 238000000926 separation method Methods 0.000 title claims description 16
- VDXLAYAQGYCQEO-UHFFFAOYSA-N 2-chloro-1,3-dimethylbenzene Chemical group CC1=CC=CC(C)=C1Cl VDXLAYAQGYCQEO-UHFFFAOYSA-N 0.000 title claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 50
- 239000003463 adsorbent Substances 0.000 claims description 31
- -1 benzene compound Chemical class 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 21
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 17
- 229910021536 Zeolite Inorganic materials 0.000 claims description 16
- 239000010457 zeolite Substances 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- NVLHGZIXTRYOKT-UHFFFAOYSA-N 1-chloro-2,3-dimethylbenzene Chemical group CC1=CC=CC(Cl)=C1C NVLHGZIXTRYOKT-UHFFFAOYSA-N 0.000 claims description 14
- 150000001768 cations Chemical class 0.000 claims description 11
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000012013 faujasite Substances 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- 239000004332 silver Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052788 barium Inorganic materials 0.000 claims description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 230000000274 adsorptive effect Effects 0.000 claims 1
- 238000001179 sorption measurement Methods 0.000 description 24
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 238000005342 ion exchange Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 229910052593 corundum Inorganic materials 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229910001845 yogo sapphire Inorganic materials 0.000 description 4
- DMEDNTFWIHCBRK-UHFFFAOYSA-N 1,3-dichloro-2-methylbenzene Chemical compound CC1=C(Cl)C=CC=C1Cl DMEDNTFWIHCBRK-UHFFFAOYSA-N 0.000 description 3
- RYMMNSVHOKXTNN-UHFFFAOYSA-N 1,3-dichloro-5-methyl-benzene Natural products CC1=CC(Cl)=CC(Cl)=C1 RYMMNSVHOKXTNN-UHFFFAOYSA-N 0.000 description 3
- 238000003795 desorption Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- GWLKCPXYBLCEKC-UHFFFAOYSA-N 1,2-dichloro-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1Cl GWLKCPXYBLCEKC-UHFFFAOYSA-N 0.000 description 1
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical class ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-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
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- XDGJPYMXPXATNG-UHFFFAOYSA-N chlorobenzene;toluene Chemical compound CC1=CC=CC=C1.ClC1=CC=CC=C1 XDGJPYMXPXATNG-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/02—Monocyclic aromatic halogenated hydrocarbons
-
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58073855A JPS59199642A (ja) | 1983-04-28 | 1983-04-28 | ２，６−ジクロルトルエンの分離方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3486207D1 DE3486207D1 (de) | 1993-10-07 |
| DE3486207T2 true DE3486207T2 (de) | 1994-02-17 |
Family
ID=13530183
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE90202602T Expired - Fee Related DE3486207T2 (de) | 1983-04-28 | 1984-04-27 | Verfahren zur Abtrennung von 2-Chlor-m-xylol. |
| DE8484302846T Expired DE3478809D1 (en) | 1983-04-28 | 1984-04-27 | Adsorptive separation process |
| DE8787200465T Expired - Fee Related DE3485064D1 (de) | 1983-04-28 | 1984-04-27 | Verfahren zur abtrennung eines chlortoluolisomers. |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8484302846T Expired DE3478809D1 (en) | 1983-04-28 | 1984-04-27 | Adsorptive separation process |
| DE8787200465T Expired - Fee Related DE3485064D1 (de) | 1983-04-28 | 1984-04-27 | Verfahren zur abtrennung eines chlortoluolisomers. |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4774371A (enExample) |
| EP (3) | EP0125077B1 (enExample) |
| JP (1) | JPS59199642A (enExample) |
| DE (3) | DE3486207T2 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59122433A (ja) * | 1982-12-28 | 1984-07-14 | Toray Ind Inc | ３，５−キシレノ−ルの分離回収方法 |
| DE3334674A1 (de) * | 1983-09-24 | 1985-04-11 | Hoechst Ag, 6230 Frankfurt | Verfahren zur isomerisierung von dichlortoluolen |
| FR2572395B1 (fr) * | 1984-10-26 | 1986-12-19 | Atochem | Procede de separation des dichlorotoluenes isomeres par adsorption sur zeolithes |
| 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 |
| 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 |
| US4922039A (en) * | 1987-12-28 | 1990-05-01 | Toray Industries | Process for separating dichlorocumene isomer |
| US4798913A (en) * | 1988-01-14 | 1989-01-17 | Hodogaya Chemical Co., Ltd. | Method for separating a trihalogenobenzene isomer |
| 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 |
| US5097835A (en) * | 1990-04-09 | 1992-03-24 | Ad-Tech Medical Instrument Corporation | Subdural electrode with improved lead connection |
| US6235952B1 (en) * | 1996-12-05 | 2001-05-22 | Toray Industries, Inc. | Method for isomerizing halogenated ethylbenzene and method for separating halogenated ethylbenzene isomers |
| US6130338A (en) * | 1998-09-08 | 2000-10-10 | Toray Industries, Inc. | Method of producing pyrrolidine derivatives |
| US6262322B1 (en) * | 1998-11-20 | 2001-07-17 | Toray Industries, Inc. | Adsorbent for aromatic isomers and production of aromatic isomers |
| JP2001131094A (ja) * | 1999-08-26 | 2001-05-15 | Toray Ind Inc | 芳香族化合物異性体の製造方法 |
| CN102311306B (zh) * | 2010-06-29 | 2014-03-26 | 中国石油化工股份有限公司 | 吸附分离二氯甲苯异构体的方法 |
| US9583891B2 (en) | 2015-06-10 | 2017-02-28 | Ad-Tech Medical Instrument Corp. | High-density electrical connector for plural multi-contact linear-array connections |
| CN106699505B (zh) * | 2016-12-30 | 2020-05-05 | 中触媒新材料股份有限公司 | 一种吸附分离二氯甲苯异构体的方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2882244A (en) * | 1953-12-24 | 1959-04-14 | Union Carbide Corp | Molecular sieve adsorbents |
| US3013985A (en) * | 1958-09-24 | 1961-12-19 | Union Carbide Corp | Group ib metal catalysts |
| US2958708A (en) * | 1959-03-23 | 1960-11-01 | Union Oil Co | Separation of isomeric halogenated aromatic compounds |
| US3135809A (en) * | 1960-07-21 | 1964-06-02 | Southern Res Inst | Isomerization process |
| US3560579A (en) * | 1968-12-20 | 1971-02-02 | Gulf Research Development Co | Process for preparing meta-halotoluene |
| FI69248C (fi) * | 1976-12-21 | 1986-01-10 | Mitsubishi Chem Ind | Foerfarande foer reglering av operationsprocessen av en simulerad roerlig baedd |
| US4155846A (en) * | 1977-10-19 | 1979-05-22 | Bowdle Paul H | Multi-segmented adsorption ion exchange or gell filtration column apparatus and process |
| DE2804203C3 (de) * | 1978-02-01 | 1980-09-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur Trennung von isomeren Dichlortoluolen |
| JPS5945371B2 (ja) * | 1980-06-13 | 1984-11-06 | 有限会社川西機械工業 | 小魚類の連続煮沸装置 |
| US4605799A (en) * | 1980-08-13 | 1986-08-12 | Toray Industries, Inc. | Process for separating a halogenated toluene isomer |
| JPS5740428A (en) * | 1980-08-25 | 1982-03-06 | Toray Ind Inc | Isomerization of halogenated toluene |
| JPS57163327A (en) * | 1981-03-31 | 1982-10-07 | Toray Ind Inc | Isomerizing method of halogenated toluene |
| DE3131682A1 (de) * | 1981-08-11 | 1983-02-24 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von p-chlortoluol und/oder m-chlortoluol |
| FR2545669B1 (fr) | 1983-05-03 | 1985-08-09 | France Etat Armement | Oscillateur a quartz compense en temperature |
-
1983
- 1983-04-28 JP JP58073855A patent/JPS59199642A/ja active Granted
-
1984
- 1984-04-27 DE DE90202602T patent/DE3486207T2/de not_active Expired - Fee Related
- 1984-04-27 DE DE8484302846T patent/DE3478809D1/de not_active Expired
- 1984-04-27 DE DE8787200465T patent/DE3485064D1/de not_active Expired - Fee Related
- 1984-04-27 EP EP84302846A patent/EP0125077B1/en not_active Expired
- 1984-04-27 EP EP90202602A patent/EP0412623B1/en not_active Expired - Lifetime
- 1984-04-27 EP EP87200465A patent/EP0246673B1/en not_active Expired
-
1986
- 1986-04-03 US US06/848,839 patent/US4774371A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59199642A (ja) | 1984-11-12 |
| EP0412623A1 (en) | 1991-02-13 |
| EP0246673B1 (en) | 1991-09-11 |
| EP0125077A1 (en) | 1984-11-14 |
| EP0246673A1 (en) | 1987-11-25 |
| DE3485064D1 (de) | 1991-10-17 |
| EP0412623B1 (en) | 1993-09-01 |
| US4774371A (en) | 1988-09-27 |
| DE3478809D1 (en) | 1989-08-03 |
| EP0125077B1 (en) | 1989-06-28 |
| JPH0145457B2 (enExample) | 1989-10-03 |
| DE3486207D1 (de) | 1993-10-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3486207T2 (de) | Verfahren zur Abtrennung von 2-Chlor-m-xylol. | |
| DE68916794T2 (de) | Verfahren zur adsorptiven Abtrennung von para-Xylol. | |
| DE2646790C3 (de) | Verfahren zur Abtennung von p-Xylol aus Gemischen mit aromatischen C8. Isomeren | |
| DE3327146C2 (de) | Verfahren zur Abtrennung von substituierten Benzolisomeren | |
| DE68914673T2 (de) | Isomerisierungskatalysator und Verfahren für seine Verwendung. | |
| DE69007683T2 (de) | Verfahren zur Herstellung von Alkylbenzolen unter Verwendung eines entaluminierten Zeolith-y-Katalysators und eines entaluminierten Mordenitkatalysators. | |
| DE2143248A1 (de) | Verfahren zum Trennen aromatischer C tief 8 Kohlenwasserstoffe | |
| EP0074651B1 (de) | Gallium- und/oder indiumhaltige Zeolithe und Verfahren zu deren Herstellung sowie ihre Verwendung | |
| DE2436076A1 (de) | Xylol-trennverfahren | |
| DE2804203B2 (de) | Verfahren zur Trennung von isomeren Dichlortoluolen | |
| DE1931519A1 (de) | Verfahren zum Trennen von aromatischen C8-Isomeren | |
| EP0077523B1 (de) | Zirkon- und/oder hafniumhaltige Zeolithe und Verfahren zu ihrer Herstellung sowie ihre Verwendung | |
| EP0164045B1 (de) | Verfahren zur Isomerisierung von Mono- oder Dichlortoluolen | |
| DE2218742A1 (de) | Verfahren zur Trennung von aromatischen C tief 8-Isomeren | |
| DE2063640C3 (de) | Verfahren zur Gewinnung von p-Xylol | |
| DE68902666T2 (de) | Verfahren zur Abtrennung von halogenierten Benzolabkömmlingen. | |
| DE3874507T2 (de) | Verfahren zur trennung von dichlorcumolisomeren. | |
| DE2703777B2 (de) | Verfahren zur Abtrennung von Xylenolen aus einem Gemisch mit Kresolen | |
| DE68905461T2 (de) | Verfahren zur behandlung eines abfallöls. | |
| EP0352505B1 (de) | Verfahren zur Herstellung von Thymol | |
| DE2049584A1 (de) | Verfahren zur Herstellung eines mit Kupfer ausgetauschten Zeohths und dessen Verwendung | |
| DE2437471C2 (de) | Verfahren zur Herstellung von p-Diäthylbenzol | |
| DE3781722T2 (de) | Verfahren zur adsorptiven trennung von dichlortoluen. | |
| EP0552633B1 (de) | Verfahren zur Trennung von m- und p-Kresol | |
| EP0094024A1 (de) | Titanhaltige Zeolithe und Verfahren zu ihrer Herstellung sowie ihre Verwendung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |