JPS6241580B2 - - Google Patents
Info
- Publication number
- JPS6241580B2 JPS6241580B2 JP16443580A JP16443580A JPS6241580B2 JP S6241580 B2 JPS6241580 B2 JP S6241580B2 JP 16443580 A JP16443580 A JP 16443580A JP 16443580 A JP16443580 A JP 16443580A JP S6241580 B2 JPS6241580 B2 JP S6241580B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- formula
- trifluoropropyl
- catalyst
- trifluoropropene
- 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
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 claims description 12
- -1 3,3,3-trifluoropropyl group Chemical group 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000003054 catalyst Substances 0.000 description 18
- 150000001555 benzenes Chemical class 0.000 description 13
- 238000009835 boiling Methods 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 238000004949 mass spectrometry Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- FFTOUVYEKNGDCM-OWOJBTEDSA-N (e)-1,3,3-trifluoroprop-1-ene Chemical compound F\C=C\C(F)F FFTOUVYEKNGDCM-OWOJBTEDSA-N 0.000 description 3
- IWDSRIHZWYDMFC-UHFFFAOYSA-N 1,1,1-trifluoro-3-(3,3,3-trifluoropropoxy)propane Chemical compound FC(F)(F)CCOCCC(F)(F)F IWDSRIHZWYDMFC-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 2
- NLMURJDGDBEMAB-UHFFFAOYSA-N 3,3,3-trifluoropropylbenzene Chemical compound FC(F)(F)CCC1=CC=CC=C1 NLMURJDGDBEMAB-UHFFFAOYSA-N 0.000 description 2
- JSBATMDYLPVVSP-UHFFFAOYSA-N 4-(3,3,3-trifluoropropyl)phenol Chemical compound OC1=CC=C(CCC(F)(F)F)C=C1 JSBATMDYLPVVSP-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SPXIVMSQSADHRY-UHFFFAOYSA-N 1-(trifluoromethyl)-2,3,4-tris(3,3,3-trifluoropropyl)benzene Chemical compound FC(F)(F)CCC1=CC=C(C(F)(F)F)C(CCC(F)(F)F)=C1CCC(F)(F)F SPXIVMSQSADHRY-UHFFFAOYSA-N 0.000 description 1
- IHVLSQJVHNPMBU-UHFFFAOYSA-N 1-(trifluoromethyl)-2,3-bis(3,3,3-trifluoropropyl)benzene Chemical compound FC(F)(F)CCC1=CC=CC(C(F)(F)F)=C1CCC(F)(F)F IHVLSQJVHNPMBU-UHFFFAOYSA-N 0.000 description 1
- YRFFLHLXMDGVFT-UHFFFAOYSA-N 1-bromo-4-(3,3,3-trifluoropropyl)benzene Chemical class FC(F)(F)CCC1=CC=C(Br)C=C1 YRFFLHLXMDGVFT-UHFFFAOYSA-N 0.000 description 1
- SPQHFZZYMOQXPJ-UHFFFAOYSA-N 1-chloro-2,3,4-tris(3,3,3-trifluoropropyl)benzene Chemical compound FC(F)(F)CCC1=CC=C(Cl)C(CCC(F)(F)F)=C1CCC(F)(F)F SPQHFZZYMOQXPJ-UHFFFAOYSA-N 0.000 description 1
- ULZSGMVXWZCQEX-UHFFFAOYSA-N 1-chloro-2,3-bis(3,3,3-trifluoropropyl)benzene Chemical compound FC(F)(F)CCC1=CC=CC(Cl)=C1CCC(F)(F)F ULZSGMVXWZCQEX-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16443580A JPS5788133A (en) | 1980-11-21 | 1980-11-21 | Preparation of benzene derivative having 3,3,3- trifluoropropyl group |
| DE3106170A DE3106170C2 (de) | 1980-02-22 | 1981-02-19 | 3,3,3-trifluorpropylierte Benzolderivate |
| FR8103389A FR2476638A1 (fr) | 1980-02-22 | 1981-02-20 | Derives substitues du benzene ayant au moins un cycle benzenique substitue par le groupe 3,3,3-trifluoropropyle, et leur preparation |
| GB8105501A GB2071087B (en) | 1980-02-22 | 1981-02-20 | Substituted benzene derivative having at least one benzene ring substituted by 3,3,3-trifluoropropyl |
| US06/320,538 US4476328A (en) | 1980-02-22 | 1981-11-12 | Process for producing 3,3,3-trifluoropropyl substituted phenol |
| US06/412,963 US4451674A (en) | 1980-02-22 | 1982-08-30 | Substituted benzene derivatives having at least one benzene ring substituted by 3,3,3-trifluoropropyl group and process for their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16443580A JPS5788133A (en) | 1980-11-21 | 1980-11-21 | Preparation of benzene derivative having 3,3,3- trifluoropropyl group |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5788133A JPS5788133A (en) | 1982-06-01 |
| JPS6241580B2 true JPS6241580B2 (enrdf_load_stackoverflow) | 1987-09-03 |
Family
ID=15793101
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16443580A Granted JPS5788133A (en) | 1980-02-22 | 1980-11-21 | Preparation of benzene derivative having 3,3,3- trifluoropropyl group |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5788133A (enrdf_load_stackoverflow) |
-
1980
- 1980-11-21 JP JP16443580A patent/JPS5788133A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5788133A (en) | 1982-06-01 |
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