CA1128962A - Process for the manufacture of 1,3,5-trichlorobenzene - Google Patents
Process for the manufacture of 1,3,5-trichlorobenzeneInfo
- Publication number
- CA1128962A CA1128962A CA352,305A CA352305A CA1128962A CA 1128962 A CA1128962 A CA 1128962A CA 352305 A CA352305 A CA 352305A CA 1128962 A CA1128962 A CA 1128962A
- Authority
- CA
- Canada
- Prior art keywords
- dinitrobenzene
- trichlorobenzene
- chlorine
- chloro
- 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
- XKEFYDZQGKAQCN-UHFFFAOYSA-N 1,3,5-trichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Cl)=C1 XKEFYDZQGKAQCN-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 239000000460 chlorine Substances 0.000 claims abstract description 23
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 22
- GFJKASVFAWFUNI-UHFFFAOYSA-N 1-chloro-3,5-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC([N+]([O-])=O)=C1 GFJKASVFAWFUNI-UHFFFAOYSA-N 0.000 claims abstract description 13
- RNABGKOKSBUFHW-UHFFFAOYSA-N 1,3-dichloro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(Cl)=C1 RNABGKOKSBUFHW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000005660 chlorination reaction Methods 0.000 description 15
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000001939 inductive effect Effects 0.000 description 4
- KMAQZIILEGKYQZ-UHFFFAOYSA-N 1-chloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1 KMAQZIILEGKYQZ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IZUKQUVSCNEFMJ-UHFFFAOYSA-N 1,2-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1[N+]([O-])=O IZUKQUVSCNEFMJ-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- FYFDQJRXFWGIBS-UHFFFAOYSA-N 1,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C([N+]([O-])=O)C=C1 FYFDQJRXFWGIBS-UHFFFAOYSA-N 0.000 description 2
- RMBFBMJGBANMMK-UHFFFAOYSA-N 2,4-dinitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RMBFBMJGBANMMK-UHFFFAOYSA-N 0.000 description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000011437 continuous method Methods 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007775 late Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- GBDZXPJXOMHESU-UHFFFAOYSA-N 1,2,3,4-tetrachlorobenzene Chemical class ClC1=CC=C(Cl)C(Cl)=C1Cl GBDZXPJXOMHESU-UHFFFAOYSA-N 0.000 description 1
- LQYCEPZHJMYYQE-UHFFFAOYSA-N 1,2,3-trichloro-4,5,6-trinitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C([N+]([O-])=O)=C1[N+]([O-])=O LQYCEPZHJMYYQE-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
- NATVSFWWYVJTAZ-UHFFFAOYSA-N 2,4,6-trichloroaniline Chemical compound NC1=C(Cl)C=C(Cl)C=C1Cl NATVSFWWYVJTAZ-UHFFFAOYSA-N 0.000 description 1
- -1 2,4-dinitrotoluene chloronitrobenzoic acid Chemical compound 0.000 description 1
- UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 description 1
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
- VCHSXYHBMFKRBK-UHFFFAOYSA-N 4771-47-5 Chemical compound OC(=O)C1=CC=CC(Cl)=C1[N+]([O-])=O VCHSXYHBMFKRBK-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 150000005182 dinitrobenzenes Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792920173 DE2920173A1 (de) | 1979-05-18 | 1979-05-18 | Verfahren zur herstellung von 1,3,5-trichlorbenzol |
| DEP2920173.8 | 1979-05-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1128962A true CA1128962A (en) | 1982-08-03 |
Family
ID=6071128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA352,305A Expired CA1128962A (en) | 1979-05-18 | 1980-05-16 | Process for the manufacture of 1,3,5-trichlorobenzene |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4306103A (en, 2012) |
| EP (1) | EP0019789B1 (en, 2012) |
| JP (1) | JPS55154926A (en, 2012) |
| CA (1) | CA1128962A (en, 2012) |
| DE (2) | DE2920173A1 (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2025120375A1 (en) * | 2023-12-07 | 2025-06-12 | Gharda Chemicals Limited | A process for the preparation of herbicide intermediates |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5692226A (en) * | 1979-12-25 | 1981-07-25 | Ishihara Sangyo Kaisha Ltd | Preparation of 1,3,5-trichlorobenzene |
| US5208394A (en) * | 1988-08-26 | 1993-05-04 | Asahi Glass Company Ltd. | Process for producing chlorofluorobenzenes |
| DE68919584T2 (de) * | 1988-08-26 | 1995-06-01 | Asahi Glass Co Ltd | Verfahren zur Herstellung von Chlorfluorbenzolen. |
| CN114349641B (zh) * | 2020-10-13 | 2024-01-30 | 中石化南京化工研究院有限公司 | 一种提纯方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2354813A (en) * | 1942-01-19 | 1944-08-01 | Monsanto Chemicals | Production of chlorinated diphenyl compounds |
| BE637746A (en, 2012) * | 1962-09-25 | |||
| US3256351A (en) * | 1963-08-22 | 1966-06-14 | Monsanto Co | Conversion of o-nitrochlorobenzene to o-dichlorobenzene |
| DE1543955A1 (de) * | 1965-12-03 | 1970-02-05 | Universal Oil Prod Co | Verfahren zur Herstellung von 3,4-Dihalogenanilinen |
-
1979
- 1979-05-18 DE DE19792920173 patent/DE2920173A1/de not_active Withdrawn
-
1980
- 1980-05-12 DE DE8080102622T patent/DE3060617D1/de not_active Expired
- 1980-05-12 EP EP80102622A patent/EP0019789B1/de not_active Expired
- 1980-05-16 JP JP6415980A patent/JPS55154926A/ja active Granted
- 1980-05-16 US US06/150,569 patent/US4306103A/en not_active Expired - Lifetime
- 1980-05-16 CA CA352,305A patent/CA1128962A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2025120375A1 (en) * | 2023-12-07 | 2025-06-12 | Gharda Chemicals Limited | A process for the preparation of herbicide intermediates |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0019789B1 (de) | 1982-06-30 |
| EP0019789A1 (de) | 1980-12-10 |
| US4306103A (en) | 1981-12-15 |
| JPS55154926A (en) | 1980-12-02 |
| JPH0118887B2 (en, 2012) | 1989-04-07 |
| DE3060617D1 (en) | 1982-08-19 |
| DE2920173A1 (de) | 1980-12-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |