JPH0149253B2 - - Google Patents
Info
- Publication number
- JPH0149253B2 JPH0149253B2 JP57120529A JP12052982A JPH0149253B2 JP H0149253 B2 JPH0149253 B2 JP H0149253B2 JP 57120529 A JP57120529 A JP 57120529A JP 12052982 A JP12052982 A JP 12052982A JP H0149253 B2 JPH0149253 B2 JP H0149253B2
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- water
- nitrobenzoic acid
- mmol
- bis
- 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
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 229910052801 chlorine Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- -1 fluoromethylphenyl Chemical group 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical class [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 235000011181 potassium carbonates Nutrition 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
- GOFURTAJNOZTTO-UHFFFAOYSA-N bis[2-chloro-4-(trifluoromethyl)phenyl] carbonate Chemical compound ClC1=CC(C(F)(F)F)=CC=C1OC(=O)OC1=CC=C(C(F)(F)F)C=C1Cl GOFURTAJNOZTTO-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- YYQSMJVVERBZPU-UHFFFAOYSA-N 4-chloro-2-ethoxy-1-nitrobenzene Chemical compound CCOC1=CC(Cl)=CC=C1[N+]([O-])=O YYQSMJVVERBZPU-UHFFFAOYSA-N 0.000 description 3
- 150000001339 alkali metal compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- ABEUJUYEUCCZQF-UHFFFAOYSA-N 4-chloro-2-methoxy-1-nitrobenzene Chemical compound COC1=CC(Cl)=CC=C1[N+]([O-])=O ABEUJUYEUCCZQF-UHFFFAOYSA-N 0.000 description 2
- CTHFLLKVPMYCPY-UHFFFAOYSA-N 5-chloro-2-nitro-n-propylbenzamide Chemical compound CCCNC(=O)C1=CC(Cl)=CC=C1[N+]([O-])=O CTHFLLKVPMYCPY-UHFFFAOYSA-N 0.000 description 2
- CKCQLHDNVOCCCN-UHFFFAOYSA-N 5-chloro-n-methyl-2-nitrobenzamide Chemical compound CNC(=O)C1=CC(Cl)=CC=C1[N+]([O-])=O CKCQLHDNVOCCCN-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000008422 chlorobenzenes Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- YXYKZYIDUAHCMZ-UHFFFAOYSA-N n,n-dibutyl-5-chloro-2-nitrobenzamide Chemical compound CCCCN(CCCC)C(=O)C1=CC(Cl)=CC=C1[N+]([O-])=O YXYKZYIDUAHCMZ-UHFFFAOYSA-N 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- BAYGVMXZJBFEMB-UHFFFAOYSA-N 4-(trifluoromethyl)phenol Chemical compound OC1=CC=C(C(F)(F)F)C=C1 BAYGVMXZJBFEMB-UHFFFAOYSA-N 0.000 description 1
- CMDZDRYXYNKLNL-UHFFFAOYSA-N 5-chloro-n,n-dimethyl-2-nitrobenzamide Chemical compound CN(C)C(=O)C1=CC(Cl)=CC=C1[N+]([O-])=O CMDZDRYXYNKLNL-UHFFFAOYSA-N 0.000 description 1
- ZHAXSUDLGOYKQV-UHFFFAOYSA-N 5-chloro-n-ethyl-2-nitrobenzamide Chemical compound CCNC(=O)C1=CC(Cl)=CC=C1[N+]([O-])=O ZHAXSUDLGOYKQV-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- JFQUVGSOOYKCAH-UHFFFAOYSA-N bis[4-(trifluoromethyl)phenyl] carbonate Chemical compound C1=CC(C(F)(F)F)=CC=C1OC(=O)OC1=CC=C(C(F)(F)F)C=C1 JFQUVGSOOYKCAH-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- RICLVXMCOVKPRW-UHFFFAOYSA-N ethyl 5-chloro-2-nitrobenzoate Chemical compound CCOC(=O)C1=CC(Cl)=CC=C1[N+]([O-])=O RICLVXMCOVKPRW-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 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
- VRUZAGKMLZNXMG-UHFFFAOYSA-N n-tert-butyl-5-chloro-2-nitrobenzamide Chemical compound CC(C)(C)NC(=O)C1=CC(Cl)=CC=C1[N+]([O-])=O VRUZAGKMLZNXMG-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- GBSQFXHHPRSEBL-UHFFFAOYSA-N tert-butyl 5-chloro-2-nitrobenzoate Chemical compound CC(C)(C)OC(=O)C1=CC(Cl)=CC=C1[N+]([O-])=O GBSQFXHHPRSEBL-UHFFFAOYSA-N 0.000 description 1
- 239000003799 water insoluble solvent Substances 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 |
|---|---|---|---|
| JP57120529A JPS5913749A (ja) | 1982-07-13 | 1982-07-13 | ４−トリフルオロメチル−４′−ニトロジフエニルエ−テル類の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57120529A JPS5913749A (ja) | 1982-07-13 | 1982-07-13 | ４−トリフルオロメチル−４′−ニトロジフエニルエ−テル類の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5913749A JPS5913749A (ja) | 1984-01-24 |
| JPH0149253B2 true JPH0149253B2 (fr) | 1989-10-24 |
Family
ID=14788524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57120529A Granted JPS5913749A (ja) | 1982-07-13 | 1982-07-13 | ４−トリフルオロメチル−４′−ニトロジフエニルエ−テル類の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5913749A (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2605668B2 (ja) * | 1986-11-28 | 1997-04-30 | カシオ計算機株式会社 | 電子弦楽器 |
| JP2679725B2 (ja) * | 1987-03-24 | 1997-11-19 | カシオ計算機株式会社 | 電子弦楽器 |
| JPS63155194U (fr) * | 1987-03-30 | 1988-10-12 | ||
| JPS63191397U (fr) * | 1987-05-27 | 1988-12-09 | ||
| JPS642297U (fr) * | 1987-06-22 | 1989-01-09 | ||
| JPS63137295A (ja) * | 1987-09-24 | 1988-06-09 | カシオ計算機株式会社 | 電子弦楽器 |
| JPH0493995A (ja) * | 1990-08-07 | 1992-03-26 | Yamaha Corp | 電子楽器 |
-
1982
- 1982-07-13 JP JP57120529A patent/JPS5913749A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5913749A (ja) | 1984-01-24 |
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