JPS6239140B2 - - Google Patents
Info
- Publication number
- JPS6239140B2 JPS6239140B2 JP54165761A JP16576179A JPS6239140B2 JP S6239140 B2 JPS6239140 B2 JP S6239140B2 JP 54165761 A JP54165761 A JP 54165761A JP 16576179 A JP16576179 A JP 16576179A JP S6239140 B2 JPS6239140 B2 JP S6239140B2
- Authority
- JP
- Japan
- Prior art keywords
- dichlorobenzene
- stage
- distillation
- distillation column
- 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.)
- Expired
Links
- 238000004821 distillation Methods 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 41
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 31
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 claims description 27
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 23
- 229940117389 dichlorobenzene Drugs 0.000 claims description 18
- 239000007791 liquid phase Substances 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 7
- 239000007790 solid phase Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- 150000004816 dichlorobenzenes Chemical class 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- 150000001555 benzenes Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000374 eutectic mixture Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical class ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GBDZXPJXOMHESU-UHFFFAOYSA-N 1,2,3,4-tetrachlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1Cl GBDZXPJXOMHESU-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- 101100111462 Arabidopsis thaliana BHLH71 gene Proteins 0.000 description 1
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
- 229910000640 Fe alloy Inorganic materials 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 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 description 1
- 239000003921 oil Substances 0.000 description 1
- CEOCDNVZRAIOQZ-UHFFFAOYSA-N pentachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl CEOCDNVZRAIOQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000001993 wax Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2855940A DE2855940C2 (de) | 1978-12-23 | 1978-12-23 | Verfahren zur Auftrennung von Dichlorbenzol enthaltenden Isomerengemischen unter Gewinnung von ortho-, meta- und/oder para-Dichlorbenzol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5587731A JPS5587731A (en) | 1980-07-02 |
| JPS6239140B2 true JPS6239140B2 (enExample) | 1987-08-21 |
Family
ID=6058244
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16576179A Granted JPS5587731A (en) | 1978-12-23 | 1979-12-21 | Manufacture of dichlorobenzene |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4300004A (enExample) |
| EP (1) | EP0012891B1 (enExample) |
| JP (1) | JPS5587731A (enExample) |
| DE (2) | DE2855940C2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01200118A (ja) * | 1988-02-04 | 1989-08-11 | Dainichi Kogyo Kk | 燃焼器の燃焼空気量制御装置 |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61268637A (ja) * | 1985-05-23 | 1986-11-28 | Kureha Chem Ind Co Ltd | ジクロロベンゼン異性体混合物からパラ体を分離する方法 |
| US5001290A (en) * | 1989-01-11 | 1991-03-19 | Battelle Memorial Institute | Production of dichlorobenzene with high para to ortho ratios |
| DE4011501A1 (de) * | 1990-04-10 | 1991-10-17 | Hoechst Ag | Verfahren zur trennung von m- und p-dichlorbenzol |
| DE4218841A1 (de) * | 1992-06-09 | 1993-12-16 | Bayer Ag | Verfahren zur Trennung von Gemischen von m- und p-Dichlorbenzol |
| US7375319B1 (en) | 2000-06-09 | 2008-05-20 | Willoughby Ross C | Laser desorption ion source |
| US7095019B1 (en) | 2003-05-30 | 2006-08-22 | Chem-Space Associates, Inc. | Remote reagent chemical ionization source |
| US6949740B1 (en) | 2002-09-13 | 2005-09-27 | Edward William Sheehan | Laminated lens for introducing gas-phase ions into the vacuum systems of mass spectrometers |
| DE10251191A1 (de) * | 2002-11-04 | 2004-05-13 | Bayer Ag | Verfahren zur Trennung von m- und p-Dichlorbenzol enthaltenden Gemischen |
| US7138626B1 (en) | 2005-05-05 | 2006-11-21 | Eai Corporation | Method and device for non-contact sampling and detection |
| US7568401B1 (en) | 2005-06-20 | 2009-08-04 | Science Applications International Corporation | Sample tube holder |
| US7576322B2 (en) | 2005-11-08 | 2009-08-18 | Science Applications International Corporation | Non-contact detector system with plasma ion source |
| US8123396B1 (en) | 2007-05-16 | 2012-02-28 | Science Applications International Corporation | Method and means for precision mixing |
| US8008617B1 (en) | 2007-12-28 | 2011-08-30 | Science Applications International Corporation | Ion transfer device |
| CN101270031B (zh) * | 2008-04-29 | 2011-02-16 | 南京师范大学 | 连续单塔多股侧线出料精馏法提取混合氯化苯中的二氯苯馏分的方法 |
| US8252965B2 (en) * | 2008-08-22 | 2012-08-28 | Honeywell International Inc. | Method for separating halocarbons |
| US8071957B1 (en) | 2009-03-10 | 2011-12-06 | Science Applications International Corporation | Soft chemical ionization source |
| WO2022045960A1 (en) * | 2020-08-28 | 2022-03-03 | Sui Jianjun | Method and device for purification of p-dichlorobenzene |
| PL246553B1 (pl) | 2022-11-04 | 2025-02-10 | Pcc Rokita Spolka Akcyjna | Sposób selektywnego otrzymywania paradichlorobenzenu z ulepszonym odzyskiem układu katalitycznego |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2527606A (en) * | 1946-07-24 | 1950-10-31 | Koppers Co Inc | Paradichlorobenzene |
| FR1374863A (fr) * | 1963-11-19 | 1964-10-09 | Bayer Ag | Séparation continue d'un mélange d'isomères dichlorobenzènes |
-
1978
- 1978-12-23 DE DE2855940A patent/DE2855940C2/de not_active Expired
-
1979
- 1979-12-05 DE DE7979104929T patent/DE2960855D1/de not_active Expired
- 1979-12-05 EP EP79104929A patent/EP0012891B1/de not_active Expired
- 1979-12-10 US US06/102,178 patent/US4300004A/en not_active Expired - Lifetime
- 1979-12-21 JP JP16576179A patent/JPS5587731A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01200118A (ja) * | 1988-02-04 | 1989-08-11 | Dainichi Kogyo Kk | 燃焼器の燃焼空気量制御装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2960855D1 (en) | 1981-12-03 |
| EP0012891B1 (de) | 1981-09-16 |
| EP0012891A1 (de) | 1980-07-09 |
| JPS5587731A (en) | 1980-07-02 |
| DE2855940C2 (de) | 1980-08-21 |
| US4300004A (en) | 1981-11-10 |
| DE2855940B1 (de) | 1979-12-13 |
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