GB902724A - Separation of aromatic isomers - Google Patents
Separation of aromatic isomersInfo
- Publication number
- GB902724A GB902724A GB2948061A GB2948061A GB902724A GB 902724 A GB902724 A GB 902724A GB 2948061 A GB2948061 A GB 2948061A GB 2948061 A GB2948061 A GB 2948061A GB 902724 A GB902724 A GB 902724A
- Authority
- GB
- United Kingdom
- Prior art keywords
- exchange fluid
- adsorbent
- mixture
- adsorbed
- fluid
- 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
- 125000003118 aryl group Chemical group 0.000 title 1
- 238000000926 separation method Methods 0.000 title 1
- 239000012530 fluid Substances 0.000 abstract 12
- 239000003463 adsorbent Substances 0.000 abstract 7
- 239000000203 mixture Substances 0.000 abstract 4
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 abstract 3
- 238000006073 displacement reaction Methods 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- 229910021536 Zeolite Inorganic materials 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 abstract 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 abstract 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 abstract 2
- 239000012071 phase Substances 0.000 abstract 2
- 238000004064 recycling Methods 0.000 abstract 2
- 239000007790 solid phase Substances 0.000 abstract 2
- 239000010457 zeolite Substances 0.000 abstract 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 abstract 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 abstract 1
- WJIFKOVZNJTSGO-UHFFFAOYSA-N 1-bromo-3-methylbenzene Chemical compound CC1=CC=CC(Br)=C1 WJIFKOVZNJTSGO-UHFFFAOYSA-N 0.000 abstract 1
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 abstract 1
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 abstract 1
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002250 absorbent Substances 0.000 abstract 1
- 230000002745 absorbent Effects 0.000 abstract 1
- 229910000323 aluminium silicate Inorganic materials 0.000 abstract 1
- 150000001896 cresols Chemical class 0.000 abstract 1
- 238000003795 desorption Methods 0.000 abstract 1
- 239000002808 molecular sieve Substances 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- 239000011148 porous material Substances 0.000 abstract 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 238000001179 sorption measurement Methods 0.000 abstract 1
- 230000003068 static effect Effects 0.000 abstract 1
- 150000004992 toluidines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
- C07C7/13—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers by molecular-sieve technique
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for effecting at least a partial resolution of a mixture of isomeric dihalobenzenes, cresols, monohalotoluenes or toluidines comprises contacting the mixture in fluid form with a solid granular absorbent consisting essentially of a zeolitic crystalline, partially dehydrated, metallo alumino silicate having pores of substantially uniform diameter between 7 and 13 and separating the fluid phase from the solid phase. The adsorbent used is a zeolite X "molecular sieve" of the type described in Specification 777,233 and U.S.A. Specification 2,882,244. The adsorbed component of the mixture may be desorbed by contacting the solid phase with a displacement exchange fluid which is adsorbed on the zeolite and from which the desorbed component may be readily separated. The adsorbent may be used in 1 or more static beds, when adsorption and desorption may take place simultaneously in different beds in the set, or as a moving compact bed. The process may be worked continuously by (1) contacting the mixture with a lean adsorbent upon which is adsorbed the displacement exchange fluid to obtain a rich adsorbent and a raffinate comprising unadsorbed components and displacement exchange fluid, (2) contacting the rich adsorbent with the exchange fluid to give a lean adsorbent and an extract comprising adsorbed components and exchange fluid, (3) recycling the lean adsorbent to (1), (4) separating exchange fluid from the raffinate and extract and (5) recycling the separated exchange fluid to (2). The process is preferably carried out in the vapour phase at 100-700 DEG F. and 0-100 p.s.i.g. In the examples the following pairs of isomers are partially separated: o- and m- and m- and p-bromotoluene, o- and p-chlorotoluene, p- and m- and o- and m-dichlorobenzene, (exchange fluid, chlorobenzene); o- and p- and m- and o-toluidine, (exchange fluid, aniline); and p- and m- and o- and m-cresol, (exchange fluid, phenol). Reference has been directed by the Comptroller to Specification 828,777.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL249278D NL249278A (en) | 1960-02-15 | ||
| US800961A US2958708A (en) | 1959-03-23 | 1959-03-23 | Separation of isomeric halogenated aromatic compounds |
| GB2948061A GB902724A (en) | 1960-02-15 | 1960-02-15 | Separation of aromatic isomers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2948061A GB902724A (en) | 1960-02-15 | 1960-02-15 | Separation of aromatic isomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB902724A true GB902724A (en) | 1962-08-09 |
Family
ID=10292223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2948061A Expired GB902724A (en) | 1959-03-23 | 1960-02-15 | Separation of aromatic isomers |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB902724A (en) |
| NL (1) | NL249278A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1131545B (en) * | 1959-02-18 | 1962-06-14 | Wilhelm Hegenscheidt Kommandit | Device for roller burnishing of cylindrical or slim conical workpieces |
| FR2465704A1 (en) * | 1979-09-20 | 1981-03-27 | Toray Industries | PROCESS FOR SEPARATING ISOMERIC ALKYLPHENOL FROM ISOMERIC MIXTURE BY ADSORPTION TECHNIQUES |
| EP0072008A1 (en) * | 1981-08-11 | 1983-02-16 | Hoechst Aktiengesellschaft | Process for the preparation of p-chlorotoluene and/or of m-chlorotoluene |
| EP0278680A1 (en) * | 1987-02-10 | 1988-08-17 | Hodogaya Chemical Co., Ltd. | Method for selective isolation of m-dichlorobenzene |
| CN110511121A (en) * | 2018-05-22 | 2019-11-29 | 中国石油化工股份有限公司 | Method for separating p-cresol by liquid phase adsorption |
| CN110511122A (en) * | 2018-05-22 | 2019-11-29 | 中国石油化工股份有限公司 | Method for separation of cresol isomers by liquid phase adsorption |
-
0
- NL NL249278D patent/NL249278A/xx unknown
-
1960
- 1960-02-15 GB GB2948061A patent/GB902724A/en not_active Expired
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1131545B (en) * | 1959-02-18 | 1962-06-14 | Wilhelm Hegenscheidt Kommandit | Device for roller burnishing of cylindrical or slim conical workpieces |
| FR2465704A1 (en) * | 1979-09-20 | 1981-03-27 | Toray Industries | PROCESS FOR SEPARATING ISOMERIC ALKYLPHENOL FROM ISOMERIC MIXTURE BY ADSORPTION TECHNIQUES |
| EP0072008A1 (en) * | 1981-08-11 | 1983-02-16 | Hoechst Aktiengesellschaft | Process for the preparation of p-chlorotoluene and/or of m-chlorotoluene |
| US4650915A (en) * | 1981-08-11 | 1987-03-17 | Hoechst Aktiengesellschaft | Process for preparing p-chlorotoluene and/or m-chlorotoluene |
| EP0278680A1 (en) * | 1987-02-10 | 1988-08-17 | Hodogaya Chemical Co., Ltd. | Method for selective isolation of m-dichlorobenzene |
| US4873383A (en) * | 1987-02-10 | 1989-10-10 | Hodogaya Chemical Co., Ltd. | Method for selective isolation of Dichlorobenzene |
| CN110511121A (en) * | 2018-05-22 | 2019-11-29 | 中国石油化工股份有限公司 | Method for separating p-cresol by liquid phase adsorption |
| CN110511122A (en) * | 2018-05-22 | 2019-11-29 | 中国石油化工股份有限公司 | Method for separation of cresol isomers by liquid phase adsorption |
| CN110511121B (en) * | 2018-05-22 | 2022-02-08 | 中国石油化工股份有限公司 | Method for separating p-cresol by liquid phase adsorption |
| CN110511122B (en) * | 2018-05-22 | 2022-03-11 | 中国石油化工股份有限公司 | Method for separating cresol isomer by liquid phase adsorption |
Also Published As
| Publication number | Publication date |
|---|---|
| NL249278A (en) |
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