CN1590356A - 含有间-和对-二氯苯的混合物的分离方法 - Google Patents
含有间-和对-二氯苯的混合物的分离方法 Download PDFInfo
- Publication number
- CN1590356A CN1590356A CN200310119849.2A CN200310119849A CN1590356A CN 1590356 A CN1590356 A CN 1590356A CN 200310119849 A CN200310119849 A CN 200310119849A CN 1590356 A CN1590356 A CN 1590356A
- Authority
- CN
- China
- Prior art keywords
- dichlorobenzene
- extraction agent
- mixture
- dcb
- different
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 36
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000000926 separation method Methods 0.000 title abstract description 20
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 title abstract 3
- 229940117389 dichlorobenzene Drugs 0.000 claims abstract description 62
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 52
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 150000002148 esters Chemical class 0.000 claims abstract description 6
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 3
- 238000000605 extraction Methods 0.000 claims description 51
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 10
- MNZAKDODWSQONA-UHFFFAOYSA-N 1-dibutylphosphorylbutane Chemical compound CCCCP(=O)(CCCC)CCCC MNZAKDODWSQONA-UHFFFAOYSA-N 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 claims description 2
- 238000007670 refining Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 238000009835 boiling Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 5
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 5
- -1 alkylene carbonate Chemical compound 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 150000004816 dichlorobenzenes Chemical class 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910002056 binary alloy Inorganic materials 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000021050 feed intake Nutrition 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
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
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
- C07C17/386—Separation; Purification; Stabilisation; Use of additives by distillation with auxiliary compounds
-
- 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
- C07C17/392—Separation; Purification; Stabilisation; Use of additives by crystallisation; Purification or separation of the crystals
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S203/00—Distillation: processes, separatory
- Y10S203/20—Power plant
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (10)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10251191.8 | 2002-11-04 | ||
DE10251191A DE10251191A1 (de) | 2002-11-04 | 2002-11-04 | Verfahren zur Trennung von m- und p-Dichlorbenzol enthaltenden Gemischen |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1590356A true CN1590356A (zh) | 2005-03-09 |
CN100391917C CN100391917C (zh) | 2008-06-04 |
Family
ID=32087333
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2003101198492A Expired - Fee Related CN100391917C (zh) | 2002-11-04 | 2003-11-04 | 含有间-和对-二氯苯的混合物的分离方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US7311807B2 (zh) |
EP (1) | EP1415964B1 (zh) |
JP (1) | JP4421873B2 (zh) |
CN (1) | CN100391917C (zh) |
DE (1) | DE10251191A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106883096A (zh) * | 2017-02-17 | 2017-06-23 | 上海科富恺机械设备有限公司 | 一种用于分离混合二氯苯的分离系统和分离方法 |
CN110746276A (zh) * | 2019-12-05 | 2020-02-04 | 万华化学集团股份有限公司 | 精馏与结晶联用生产邻叔丁基苯酚和对叔丁基苯酚的方法 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2243530A1 (de) | 2009-04-21 | 2010-10-27 | LANXESS Deutschland GmbH | Verfahren zur Trennung aromatischer Verbindungen |
CN111116309A (zh) * | 2018-10-30 | 2020-05-08 | 中国石油化工股份有限公司 | 一种混合二氯苯分离的工业化方法 |
WO2022045960A1 (en) * | 2020-08-28 | 2022-03-03 | Sui Jianjun | Method and device for purification of p-dichlorobenzene |
CN112370810A (zh) * | 2020-09-30 | 2021-02-19 | 南通新邦化工科技有限公司 | 易氧化易凝固化工物料回收利用方法及装置 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3170961A (en) | 1961-02-24 | 1965-02-23 | Dow Chemical Co | Process for separating dichlorobenzene isomers |
US3800002A (en) * | 1970-03-20 | 1974-03-26 | Japan Synthetic Rubber Co Ltd | Process for preventing the polymerization of conjugated dienes |
FR2190782B1 (zh) | 1972-06-30 | 1974-12-27 | Rhone Progil | |
FR2348903A2 (fr) | 1975-06-25 | 1977-11-18 | Rhone Poulenc Ind | Procede de separation d'hydrocarbures aliphatiques chlores ayant 1 a 3 atomes de carbone a partir de leurs melanges par distillation extractive |
JPS5344528A (en) | 1976-10-05 | 1978-04-21 | Mitsui Toatsu Chem Inc | Separation of dihalogenobenzenes |
JPS54160322A (en) | 1978-06-07 | 1979-12-19 | Nippon Kayaku Co Ltd | Separation of dichlorobenzene isomer |
DE2855940C2 (de) * | 1978-12-23 | 1980-08-21 | Bayer Ag, 5090 Leverkusen | Verfahren zur Auftrennung von Dichlorbenzol enthaltenden Isomerengemischen unter Gewinnung von ortho-, meta- und/oder para-Dichlorbenzol |
US4292142A (en) * | 1981-01-12 | 1981-09-29 | International Synthetic Rubber Co., Ltd. | Separation of ethylbenzene from para- and meta-xylenes by extractive distillation |
JPS58174333A (ja) | 1982-04-08 | 1983-10-13 | Hodogaya Chem Co Ltd | ジクロロベンゼン異性体の分離方法 |
JPS62123135A (ja) | 1985-11-21 | 1987-06-04 | Sumitomo Chem Co Ltd | 単環炭化水素類の分離方法 |
DE4011501A1 (de) | 1990-04-10 | 1991-10-17 | Hoechst Ag | Verfahren zur trennung von m- und p-dichlorbenzol |
DE4330731A1 (de) * | 1993-09-10 | 1995-03-16 | Bayer Ag | Verfahren zur Isolierung von m-Dichlorbenzol aus Dichlorbenzol-Isomerengemischen |
US5986133A (en) * | 1997-06-30 | 1999-11-16 | The Texas A&M University System | Recovery of fermentation salts from dilute aqueous solutions |
JPH11158093A (ja) | 1997-11-28 | 1999-06-15 | Toray Ind Inc | ジクロロベンゼン異性体の分離方法 |
-
2002
- 2002-11-04 DE DE10251191A patent/DE10251191A1/de not_active Withdrawn
-
2003
- 2003-10-24 EP EP03024494A patent/EP1415964B1/de not_active Expired - Lifetime
- 2003-10-31 JP JP2003373263A patent/JP4421873B2/ja not_active Expired - Fee Related
- 2003-11-04 CN CNB2003101198492A patent/CN100391917C/zh not_active Expired - Fee Related
- 2003-11-04 US US10/701,339 patent/US7311807B2/en active Active
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106883096A (zh) * | 2017-02-17 | 2017-06-23 | 上海科富恺机械设备有限公司 | 一种用于分离混合二氯苯的分离系统和分离方法 |
CN110746276A (zh) * | 2019-12-05 | 2020-02-04 | 万华化学集团股份有限公司 | 精馏与结晶联用生产邻叔丁基苯酚和对叔丁基苯酚的方法 |
CN110746276B (zh) * | 2019-12-05 | 2022-08-02 | 万华化学集团股份有限公司 | 精馏与结晶联用生产邻叔丁基苯酚和对叔丁基苯酚的方法 |
Also Published As
Publication number | Publication date |
---|---|
CN100391917C (zh) | 2008-06-04 |
DE10251191A1 (de) | 2004-05-13 |
US7311807B2 (en) | 2007-12-25 |
EP1415964A1 (de) | 2004-05-06 |
EP1415964B1 (de) | 2013-02-13 |
JP4421873B2 (ja) | 2010-02-24 |
JP2004155782A (ja) | 2004-06-03 |
US20040144637A1 (en) | 2004-07-29 |
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C06 | Publication | ||
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C10 | Entry into substantive examination | ||
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ASS | Succession or assignment of patent right |
Owner name: LANXESS DEUTSCHLAND GMBH Free format text: FORMER OWNER: BAYER CHEMICALS AG Effective date: 20070608 |
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Effective date of registration: 20070608 Address after: The Federal Republic of Germany Leverkusen Applicant after: LANXESS DEUTSCHLAND GmbH Address before: The Federal Republic of Germany Leverkusen Applicant before: BAYER CHEMICALS AG |
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C56 | Change in the name or address of the patentee |
Owner name: LANXESS GERMAN LIMITED LIABILITY COMPANY Free format text: FORMER NAME OR ADDRESS: LANXESS DEUTSCHLAND GMBH |
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CP03 | Change of name, title or address |
Address after: Germany Leverkusen Patentee after: Lanxess Deutschland GmbH Address before: The Federal Republic of Germany Leverkusen Patentee before: Lanxess Deutschland GmbH |
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CF01 | Termination of patent right due to non-payment of annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20080604 |