JPH0242824B2 - - Google Patents
Info
- Publication number
- JPH0242824B2 JPH0242824B2 JP58248050A JP24805083A JPH0242824B2 JP H0242824 B2 JPH0242824 B2 JP H0242824B2 JP 58248050 A JP58248050 A JP 58248050A JP 24805083 A JP24805083 A JP 24805083A JP H0242824 B2 JPH0242824 B2 JP H0242824B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- dichloro
- trifluorobenzonitrile
- reacted
- solvent
- 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 - Lifetime
Links
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 17
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 16
- -1 aluminum halide Chemical class 0.000 claims description 15
- HTKFGTCCOJIUIK-UHFFFAOYSA-N 2,4,6-trifluorobenzonitrile Chemical compound FC1=CC(F)=C(C#N)C(F)=C1 HTKFGTCCOJIUIK-UHFFFAOYSA-N 0.000 claims description 11
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- YEYBWCZPVMFKKZ-UHFFFAOYSA-N 2-bromo-4,6-dichlorobenzonitrile Chemical compound ClC1=CC(Cl)=C(C#N)C(Br)=C1 YEYBWCZPVMFKKZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- DZHFFMWJXJBBRG-UHFFFAOYSA-N 1-bromo-3,5-dichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Br)=C1 DZHFFMWJXJBBRG-UHFFFAOYSA-N 0.000 claims description 3
- PGODHCIOIPODFE-UHFFFAOYSA-N 2,4,6-trichlorobenzonitrile Chemical compound ClC1=CC(Cl)=C(C#N)C(Cl)=C1 PGODHCIOIPODFE-UHFFFAOYSA-N 0.000 claims description 3
- NKWBLKGGKNHCSU-UHFFFAOYSA-N 4-bromo-2,6-dichlorobenzonitrile Chemical compound ClC1=CC(Br)=CC(Cl)=C1C#N NKWBLKGGKNHCSU-UHFFFAOYSA-N 0.000 claims description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims 2
- OXOHTICHGYFWNF-UHFFFAOYSA-N 1,3,5-trichloro-2-(trichloromethyl)benzene Chemical compound ClC1=CC(Cl)=C(C(Cl)(Cl)Cl)C(Cl)=C1 OXOHTICHGYFWNF-UHFFFAOYSA-N 0.000 claims 1
- KTPHYLJFAZNALV-UHFFFAOYSA-N 2,3,4-trifluorobenzonitrile Chemical compound FC1=CC=C(C#N)C(F)=C1F KTPHYLJFAZNALV-UHFFFAOYSA-N 0.000 claims 1
- 235000011164 potassium chloride Nutrition 0.000 claims 1
- 239000001103 potassium chloride Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 18
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 18
- 239000002904 solvent Substances 0.000 description 12
- 235000003270 potassium fluoride Nutrition 0.000 description 9
- 239000011698 potassium fluoride Substances 0.000 description 9
- 238000007333 cyanation reaction Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical compound ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000003682 fluorination reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- XKEFYDZQGKAQCN-UHFFFAOYSA-N 1,3,5-trichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Cl)=C1 XKEFYDZQGKAQCN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- BAPPAFMEUDJAQI-UHFFFAOYSA-N 2-bromo-1,3,5-trichlorobenzene Chemical compound ClC1=CC(Cl)=C(Br)C(Cl)=C1 BAPPAFMEUDJAQI-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HVKCZUVMQPUWSX-UHFFFAOYSA-N 1-bromo-2,3-dichlorobenzene Chemical compound ClC1=CC=CC(Br)=C1Cl HVKCZUVMQPUWSX-UHFFFAOYSA-N 0.000 description 1
- HZPJPMSPYIODNA-UHFFFAOYSA-N 2,4,6-trifluorobenzamide Chemical compound NC(=O)C1=C(F)C=C(F)C=C1F HZPJPMSPYIODNA-UHFFFAOYSA-N 0.000 description 1
- KROBIUFTVIMUQL-UHFFFAOYSA-N 2,4,6-trifluorobenzoyl isocyanate Chemical compound FC1=CC(F)=C(C(=O)N=C=O)C(F)=C1 KROBIUFTVIMUQL-UHFFFAOYSA-N 0.000 description 1
- KCLWRVQIRVOVLJ-UHFFFAOYSA-N 3,5-dichloro-4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxyaniline Chemical compound ClC1=CC(N)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl KCLWRVQIRVOVLJ-UHFFFAOYSA-N 0.000 description 1
- HQSCPPCMBMFJJN-UHFFFAOYSA-N 4-bromobenzonitrile Chemical compound BrC1=CC=C(C#N)C=C1 HQSCPPCMBMFJJN-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GWCREUPCCPPMNC-UHFFFAOYSA-N n-[[3,5-dichloro-4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxyphenyl]carbamoyl]-2,4,6-trifluorobenzamide Chemical compound FC1=CC(F)=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl GWCREUPCCPPMNC-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
Classifications
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58248050A JPS60142950A (ja) | 1983-12-28 | 1983-12-28 | ２，４，６−トリフルオロベンゾニトリルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58248050A JPS60142950A (ja) | 1983-12-28 | 1983-12-28 | ２，４，６−トリフルオロベンゾニトリルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60142950A JPS60142950A (ja) | 1985-07-29 |
| JPH0242824B2 true JPH0242824B2 (en, 2012) | 1990-09-26 |
Family
ID=17172447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58248050A Granted JPS60142950A (ja) | 1983-12-28 | 1983-12-28 | ２，４，６−トリフルオロベンゾニトリルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60142950A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3592724B1 (en) * | 2017-03-08 | 2023-05-10 | Srf Limited | Processes for the preparation of halo substituted benzoic acid compounds |
| CN113024412A (zh) * | 2021-03-23 | 2021-06-25 | 上海立科化学科技有限公司 | 2,4,6-三氯苯腈的制备方法 |
-
1983
- 1983-12-28 JP JP58248050A patent/JPS60142950A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60142950A (ja) | 1985-07-29 |
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