DE2535696B2 - Verfahren zur Herstellung von a , a , a , a ', a '-Pentachlor-o-xylol - Google Patents
Verfahren zur Herstellung von a , a , a , a ', a '-Pentachlor-o-xylolInfo
- Publication number
- DE2535696B2 DE2535696B2 DE2535696A DE2535696A DE2535696B2 DE 2535696 B2 DE2535696 B2 DE 2535696B2 DE 2535696 A DE2535696 A DE 2535696A DE 2535696 A DE2535696 A DE 2535696A DE 2535696 B2 DE2535696 B2 DE 2535696B2
- Authority
- DE
- Germany
- Prior art keywords
- xylene
- chlorine
- reaction
- carbon tetrachloride
- chlorination
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 22
- 229940078552 o-xylene Drugs 0.000 title claims description 18
- 230000008569 process Effects 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 46
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 41
- 239000000460 chlorine Substances 0.000 claims description 35
- 229910052801 chlorine Inorganic materials 0.000 claims description 33
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 238000010521 absorption reaction Methods 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 11
- 239000011521 glass Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000008096 xylene Substances 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000007789 gas Substances 0.000 claims description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 5
- 229910052753 mercury Inorganic materials 0.000 claims description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 238000003795 desorption Methods 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 210000003298 dental enamel Anatomy 0.000 claims description 2
- 239000000428 dust Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 229910052715 tantalum Inorganic materials 0.000 claims description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000009189 diving Effects 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 description 29
- 239000000047 product Substances 0.000 description 20
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229910052742 iron Inorganic materials 0.000 description 8
- 238000009835 boiling Methods 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 238000007086 side reaction Methods 0.000 description 5
- MFHPYLFZSCSNST-UHFFFAOYSA-N 1-chloro-2-(trichloromethyl)benzene Chemical compound ClC1=CC=CC=C1C(Cl)(Cl)Cl MFHPYLFZSCSNST-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- -1 halogen cations Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- QICXTGCEPZAKNJ-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5-(chloromethyl)-6-methylbenzene Chemical group CC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1CCl QICXTGCEPZAKNJ-UHFFFAOYSA-N 0.000 description 3
- BXSVYGKOUULJCL-UHFFFAOYSA-N 1-chloro-2-(dichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=CC=C1Cl BXSVYGKOUULJCL-UHFFFAOYSA-N 0.000 description 3
- 150000001804 chlorine Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000007701 flash-distillation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 2
- SCOSFGXUBLANNC-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5,6-dimethylbenzene Chemical group CC1=C(C)C(Cl)=C(Cl)C(Cl)=C1Cl SCOSFGXUBLANNC-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000011403 purification operation Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GTLWADFFABIGAE-UHFFFAOYSA-N 1-chloroethylbenzene Chemical compound CC(Cl)C1=CC=CC=C1 GTLWADFFABIGAE-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 101100102516 Clonostachys rogersoniana vern gene Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- UETQVDZZPKAQIC-UHFFFAOYSA-N chlorane Chemical compound Cl.Cl.Cl.Cl UETQVDZZPKAQIC-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010367 cloning Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000001491 hyper Rayleigh scattering spectroscopy Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002506 iron compounds Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 150000002673 m-xylene Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229940054441 o-phthalaldehyde Drugs 0.000 description 1
- 150000002884 o-xylenes Chemical class 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2535696A DE2535696B2 (de) | 1975-08-09 | 1975-08-09 | Verfahren zur Herstellung von a , a , a , a ', a '-Pentachlor-o-xylol |
| US05/710,834 US4056454A (en) | 1975-08-09 | 1976-08-02 | Process for the preparation of α,α,αα',α'-pentachloro-o-xylene |
| GB32565/76A GB1503877A (en) | 1975-08-09 | 1976-08-04 | Process for producing alpha alpha alpha alpha',alpha' pentachloro-ortho-xylene |
| NL7608770A NL7608770A (nl) | 1975-08-09 | 1976-08-06 | Werkwijze ter bereiding van (alpha),(alpha),(alpha),(alpha)',(alpha)'-penta- chloor-o-xylenen. |
| FR7624215A FR2320927A1 (fr) | 1975-08-09 | 1976-08-06 | Procede pour l'obtention d'a,a,a,a',a', pentachloro-o-xylene |
| JP51094727A JPS5223028A (en) | 1975-08-09 | 1976-08-09 | Preparation of alpha* alpha* alpha** alpha** alphaapentachlorooooxylol |
| BE169667A BE845017A (fr) | 1975-08-09 | 1976-08-09 | Procede pour l'obtention d'alpha,alpha,alpha,alpha',alpha',-pentachloro-o-xylene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2535696A DE2535696B2 (de) | 1975-08-09 | 1975-08-09 | Verfahren zur Herstellung von a , a , a , a ', a '-Pentachlor-o-xylol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2535696A1 DE2535696A1 (de) | 1977-02-17 |
| DE2535696B2 true DE2535696B2 (de) | 1979-09-13 |
Family
ID=5953698
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2535696A Ceased DE2535696B2 (de) | 1975-08-09 | 1975-08-09 | Verfahren zur Herstellung von a , a , a , a ', a '-Pentachlor-o-xylol |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4056454A (enExample) |
| JP (1) | JPS5223028A (enExample) |
| BE (1) | BE845017A (enExample) |
| DE (1) | DE2535696B2 (enExample) |
| FR (1) | FR2320927A1 (enExample) |
| GB (1) | GB1503877A (enExample) |
| NL (1) | NL7608770A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3233392A1 (de) * | 1982-08-31 | 1984-03-01 | Gebrüder Sulzer AG, 8401 Winterthur | Tellerventil fuer ein gaswechselventil |
| JP4641839B2 (ja) * | 2005-03-23 | 2011-03-02 | セントラル硝子株式会社 | ４−メチル−３−トリフルオロメチル安息香酸の製造方法 |
| WO2016142669A1 (en) | 2015-03-06 | 2016-09-15 | Micromass Uk Limited | Physically guided rapid evaporative ionisation mass spectrometry ("reims") |
| CN111825520A (zh) * | 2020-07-27 | 2020-10-27 | 西安思科赛实业有限公司 | α,α,α’,α’-四氯邻二甲苯的制备工艺 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE668033C (de) * | 1935-10-26 | 1938-11-25 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von o-Trifluormethyldifluorchlormethylbenzolen bzw. o-Hexafluordimethylbenzolen |
| US2810688A (en) * | 1954-08-20 | 1957-10-22 | Dow Chemical Co | Process for preparation of poly(perchloromethyl) benzenes |
| NL248810A (enExample) * | 1959-03-27 | |||
| US3703473A (en) * | 1966-06-29 | 1972-11-21 | Diamond Shamrock Corp | Sequestering agents for metal ion contamination of alkyl-aromatic hydrocarbons |
| JPS5545536B2 (enExample) * | 1973-09-10 | 1980-11-18 |
-
1975
- 1975-08-09 DE DE2535696A patent/DE2535696B2/de not_active Ceased
-
1976
- 1976-08-02 US US05/710,834 patent/US4056454A/en not_active Expired - Lifetime
- 1976-08-04 GB GB32565/76A patent/GB1503877A/en not_active Expired
- 1976-08-06 FR FR7624215A patent/FR2320927A1/fr active Granted
- 1976-08-06 NL NL7608770A patent/NL7608770A/xx not_active Application Discontinuation
- 1976-08-09 JP JP51094727A patent/JPS5223028A/ja active Pending
- 1976-08-09 BE BE169667A patent/BE845017A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5223028A (en) | 1977-02-21 |
| US4056454A (en) | 1977-11-01 |
| NL7608770A (nl) | 1977-02-11 |
| DE2535696A1 (de) | 1977-02-17 |
| GB1503877A (en) | 1978-03-15 |
| FR2320927A1 (fr) | 1977-03-11 |
| FR2320927B1 (enExample) | 1981-09-18 |
| BE845017A (fr) | 1976-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8235 | Patent refused |