JPS6230972B2 - - Google Patents
Info
- Publication number
- JPS6230972B2 JPS6230972B2 JP12537481A JP12537481A JPS6230972B2 JP S6230972 B2 JPS6230972 B2 JP S6230972B2 JP 12537481 A JP12537481 A JP 12537481A JP 12537481 A JP12537481 A JP 12537481A JP S6230972 B2 JPS6230972 B2 JP S6230972B2
- Authority
- JP
- Japan
- Prior art keywords
- chloride
- benzal
- chlorides
- reaction
- benzaldehydes
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
- 150000003935 benzaldehydes Chemical class 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 8
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229910052748 manganese Inorganic materials 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 150000003841 chloride salts Chemical class 0.000 claims 1
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 26
- 238000000034 method Methods 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 10
- 239000007789 gas Substances 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 230000003301 hydrolyzing effect Effects 0.000 description 6
- 239000006200 vaporizer Substances 0.000 description 6
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 5
- 229960003280 cupric chloride Drugs 0.000 description 5
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 235000012239 silicon dioxide Nutrition 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- JIJFXGFHPXLJME-UHFFFAOYSA-N 1-(dichloromethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1C(Cl)Cl JIJFXGFHPXLJME-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 229940045803 cuprous chloride Drugs 0.000 description 3
- 238000007598 dipping method Methods 0.000 description 3
- -1 trifluoro-substituted benzal chlorides Chemical class 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- ACNQJGLSENYFQJ-UHFFFAOYSA-N 1-chloro-3-(dichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=CC(Cl)=C1 ACNQJGLSENYFQJ-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- ZDVRPKUWYQVVDX-UHFFFAOYSA-N 2-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC=C1C=O ZDVRPKUWYQVVDX-UHFFFAOYSA-N 0.000 description 2
- SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 229910001510 metal chloride Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- QMRLRZLQIJAGSQ-UHFFFAOYSA-N 1,3-dibromo-2-(dichloromethyl)benzene Chemical compound ClC(Cl)C1=C(Br)C=CC=C1Br QMRLRZLQIJAGSQ-UHFFFAOYSA-N 0.000 description 1
- QQPXXHAEIGVZKQ-UHFFFAOYSA-N 1,3-dichloro-2-(dichloromethyl)benzene Chemical compound ClC(Cl)C1=C(Cl)C=CC=C1Cl QQPXXHAEIGVZKQ-UHFFFAOYSA-N 0.000 description 1
- VBPLROSJWVETJQ-UHFFFAOYSA-N 1,4-dichloro-2-(dichloromethyl)benzene Chemical compound ClC(Cl)C1=CC(Cl)=CC=C1Cl VBPLROSJWVETJQ-UHFFFAOYSA-N 0.000 description 1
- XFAFBKQDEPXWCS-UHFFFAOYSA-N 1-(dichloromethyl)-2-fluorobenzene Chemical compound FC1=CC=CC=C1C(Cl)Cl XFAFBKQDEPXWCS-UHFFFAOYSA-N 0.000 description 1
- MVRCPAOYPLZMLB-UHFFFAOYSA-N 1-(dichloromethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(C(Cl)Cl)=C1 MVRCPAOYPLZMLB-UHFFFAOYSA-N 0.000 description 1
- GDZMMXXMEMTSJY-UHFFFAOYSA-N 1-(dichloromethyl)-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(C(Cl)Cl)C=C1 GDZMMXXMEMTSJY-UHFFFAOYSA-N 0.000 description 1
- MFIOEEWGBMJNGG-UHFFFAOYSA-N 1-(dichloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(C(Cl)Cl)C=C1 MFIOEEWGBMJNGG-UHFFFAOYSA-N 0.000 description 1
- PQYGNIRJOCANCU-UHFFFAOYSA-N 1-bromo-4-(dichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=C(Br)C=C1 PQYGNIRJOCANCU-UHFFFAOYSA-N 0.000 description 1
- VWHNJDGWDOQJRM-UHFFFAOYSA-N 1-chloro-4-(dichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=C(Cl)C=C1 VWHNJDGWDOQJRM-UHFFFAOYSA-N 0.000 description 1
- XQAYFQKXUOLNPQ-UHFFFAOYSA-N 2,4-dibromo-1-(dichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=C(Br)C=C1Br XQAYFQKXUOLNPQ-UHFFFAOYSA-N 0.000 description 1
- PGSVNTIDEZRNES-UHFFFAOYSA-N 2,4-dibromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C(Br)=C1 PGSVNTIDEZRNES-UHFFFAOYSA-N 0.000 description 1
- AQVKVGOTPBBVMS-UHFFFAOYSA-N 2,4-dichloro-1-(dichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=C(Cl)C=C1Cl AQVKVGOTPBBVMS-UHFFFAOYSA-N 0.000 description 1
- YSFBEAASFUWWHU-UHFFFAOYSA-N 2,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C(Cl)=C1 YSFBEAASFUWWHU-UHFFFAOYSA-N 0.000 description 1
- BQBXKWGMPUCSQV-UHFFFAOYSA-N 2,5-dibromobenzaldehyde Chemical compound BrC1=CC=C(Br)C(C=O)=C1 BQBXKWGMPUCSQV-UHFFFAOYSA-N 0.000 description 1
- BUXHYMZMVMNDMG-UHFFFAOYSA-N 2,5-dichlorobenzaldehyde Chemical compound ClC1=CC=C(Cl)C(C=O)=C1 BUXHYMZMVMNDMG-UHFFFAOYSA-N 0.000 description 1
- YDYNSAUGVGAOLO-UHFFFAOYSA-N 2,6-dibromobenzaldehyde Chemical compound BrC1=CC=CC(Br)=C1C=O YDYNSAUGVGAOLO-UHFFFAOYSA-N 0.000 description 1
- DMIYKWPEFRFTPY-UHFFFAOYSA-N 2,6-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(Cl)=C1C=O DMIYKWPEFRFTPY-UHFFFAOYSA-N 0.000 description 1
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
- ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 1
- NMTUHPSKJJYGML-UHFFFAOYSA-N 3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1 NMTUHPSKJJYGML-UHFFFAOYSA-N 0.000 description 1
- PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 description 1
- BEOBZEOPTQQELP-UHFFFAOYSA-N 4-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=C(C=O)C=C1 BEOBZEOPTQQELP-UHFFFAOYSA-N 0.000 description 1
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- BAOZSBKGJKXRTG-UHFFFAOYSA-N C1=CC=C(C(=C1)C(Cl)(Cl)Br)Br Chemical compound C1=CC=C(C(=C1)C(Cl)(Cl)Br)Br BAOZSBKGJKXRTG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 229940097267 cobaltous chloride Drugs 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229940032296 ferric chloride Drugs 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 229940099607 manganese chloride Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229960001939 zinc chloride Drugs 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12537481A JPS5829735A (ja) | 1981-08-12 | 1981-08-12 | ベンズアルデヒド類の製造法 |
| GB08218612A GB2103208B (en) | 1981-07-21 | 1982-06-28 | Vapor phase catalytic hydrolysis of benzal chloride or its halogen- or trifluoromethyl-substitute to form benzaldehyde or substitute |
| IT22211/82A IT1157289B (it) | 1981-07-21 | 1982-07-02 | Idrolisi catalitica in fas vapore di cloruro di benzale o il suo alogeno o trifluorometil-sostituto per formare benzaldeide o sostituto |
| DE3226490A DE3226490C2 (de) | 1981-07-21 | 1982-07-15 | Verfahren zur Herstellung von Benzaldehyd oder dessen Halogen- oder Trifluormethylverbindungen durch katalytische Dampfphasenhydrolyse von Benzalchlorid oder den entsprechend substituierten Verbindungen |
| FR8212665A FR2510101B1 (fr) | 1981-07-21 | 1982-07-20 | Procede d'hydrolyse catalytique en phase vapeur de chlorure de benzal ou son substitut avec un halogene ou un trifluoromethyle, pour former du benzaldehyde ou son substitut |
| US06/400,011 US4450298A (en) | 1981-07-21 | 1982-07-20 | Vapor phase catalytic hydrolysis of benzal chloride or its halogen- or trifluoromethyl-substitute to form benzaldehyde or substitute |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12537481A JPS5829735A (ja) | 1981-08-12 | 1981-08-12 | ベンズアルデヒド類の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5829735A JPS5829735A (ja) | 1983-02-22 |
| JPS6230972B2 true JPS6230972B2 (enrdf_load_stackoverflow) | 1987-07-06 |
Family
ID=14908544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12537481A Granted JPS5829735A (ja) | 1981-07-21 | 1981-08-12 | ベンズアルデヒド類の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5829735A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4621678A (en) * | 1982-09-13 | 1986-11-11 | Cosden Technology, Inc. | Heat exchanger apparatus for extruding thermoplastic compositions |
| JP4489532B2 (ja) * | 2004-08-03 | 2010-06-23 | セントラル硝子株式会社 | ３−ホルミル−５−トリフルオロメチルベンゾニトリル誘導体とその製造方法 |
-
1981
- 1981-08-12 JP JP12537481A patent/JPS5829735A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5829735A (ja) | 1983-02-22 |
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