JPH0156054B2 - - Google Patents
Info
- Publication number
- JPH0156054B2 JPH0156054B2 JP63040946A JP4094688A JPH0156054B2 JP H0156054 B2 JPH0156054 B2 JP H0156054B2 JP 63040946 A JP63040946 A JP 63040946A JP 4094688 A JP4094688 A JP 4094688A JP H0156054 B2 JPH0156054 B2 JP H0156054B2
- Authority
- JP
- Japan
- Prior art keywords
- bromine
- halogenated hydrocarbon
- formula
- starting material
- polar neutral
- 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
- 238000000034 method Methods 0.000 claims description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 150000008282 halocarbons Chemical class 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- 230000007935 neutral effect Effects 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 8
- 150000008045 alkali metal halides Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical group [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000001030 gas--liquid chromatography Methods 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 1
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical class CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 1
- JXOGUSUARSCHAD-UHFFFAOYSA-N 2,2,4-trichloro-1,1,1-trifluoro-5-methylhexane Chemical compound CC(C)C(Cl)CC(Cl)(Cl)C(F)(F)F JXOGUSUARSCHAD-UHFFFAOYSA-N 0.000 description 1
- GSSNCQXGQSCKSL-UHFFFAOYSA-N 2-chloro-1,1,1-trifluoro-5-methylhexa-2,4-diene Chemical group CC(C)=CC=C(Cl)C(F)(F)F GSSNCQXGQSCKSL-UHFFFAOYSA-N 0.000 description 1
- JRAGTVVQLNANCA-UHFFFAOYSA-N 5,5-dichloro-6,6,6-trifluoro-2-methylhex-2-ene Chemical compound CC(C)=CCC(Cl)(Cl)C(F)(F)F JRAGTVVQLNANCA-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-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
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- AFVLVVWMAFSXCK-VMPITWQZSA-N alpha-cyano-4-hydroxycinnamic acid Chemical class OC(=O)C(\C#N)=C\C1=CC=C(O)C=C1 AFVLVVWMAFSXCK-VMPITWQZSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- -1 α-ethynyl Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/19—Halogenated dienes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2242978 | 1978-05-25 | ||
| GB22429/78 | 1978-05-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63258435A JPS63258435A (ja) | 1988-10-25 |
| JPH0156054B2 true JPH0156054B2 (en]) | 1989-11-28 |
Family
ID=10179232
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6407079A Granted JPS54163506A (en) | 1978-05-25 | 1979-05-25 | Halogenated hydrocarbon and its manufacture |
| JP63040946A Granted JPS63258435A (ja) | 1978-05-25 | 1988-02-25 | ハロゲン化炭化水素の製法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6407079A Granted JPS54163506A (en) | 1978-05-25 | 1979-05-25 | Halogenated hydrocarbon and its manufacture |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4210611A (en]) |
| JP (2) | JPS54163506A (en]) |
| CH (1) | CH642041A5 (en]) |
| DE (1) | DE2920591A1 (en]) |
| DK (1) | DK213479A (en]) |
| FR (1) | FR2426665A1 (en]) |
| IT (1) | IT1115235B (en]) |
| NL (1) | NL7904057A (en]) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4228107A (en) * | 1978-05-25 | 1980-10-14 | Imperial Chemical Industries Limited | Polyhalogenated hydrocarbons, useful as insecticide intermediates, and methods for their preparation |
| DE2835480A1 (de) * | 1978-08-12 | 1980-02-28 | Hoechst Ag | Fluorhaltige 1.3-diene, deren herstellung und deren verwendung |
| EP0022606B1 (en) * | 1979-07-13 | 1983-01-12 | Imperial Chemical Industries Plc | Process for the manufacture of halogenated hydrocarbons |
| ZA849230B (en) * | 1983-12-07 | 1985-07-31 | Fmc Corp | Biocidal fluoroalkanes and fluoroalkenes |
| US8530708B2 (en) * | 2003-07-25 | 2013-09-10 | Honeywell International Inc. | Processes for selective dehydrohalogenation of halogenated alkanes |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3925491A (en) * | 1973-02-28 | 1975-12-09 | Ugine Kuhlmann | New fluorinated dienes and process for preparing same |
| EP0010856B1 (en) * | 1978-10-26 | 1982-10-27 | Imperial Chemical Industries Plc | Halogenated hydrocarbons and a method for their preparation |
-
1979
- 1979-05-18 US US06/040,455 patent/US4210611A/en not_active Expired - Lifetime
- 1979-05-21 DE DE19792920591 patent/DE2920591A1/de active Granted
- 1979-05-22 CH CH480179A patent/CH642041A5/de not_active IP Right Cessation
- 1979-05-23 NL NL7904057A patent/NL7904057A/xx not_active Application Discontinuation
- 1979-05-23 DK DK213479A patent/DK213479A/da unknown
- 1979-05-23 FR FR7913265A patent/FR2426665A1/fr active Granted
- 1979-05-23 IT IT22924/79A patent/IT1115235B/it active
- 1979-05-25 JP JP6407079A patent/JPS54163506A/ja active Granted
-
1988
- 1988-02-25 JP JP63040946A patent/JPS63258435A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4210611A (en) | 1980-07-01 |
| DE2920591C2 (en]) | 1989-11-16 |
| JPS63258435A (ja) | 1988-10-25 |
| FR2426665B1 (en]) | 1983-03-11 |
| DE2920591A1 (de) | 1979-11-29 |
| JPH0154333B2 (en]) | 1989-11-17 |
| DK213479A (da) | 1979-11-26 |
| IT1115235B (it) | 1986-02-03 |
| FR2426665A1 (fr) | 1979-12-21 |
| IT7922924A0 (it) | 1979-05-23 |
| JPS54163506A (en) | 1979-12-26 |
| NL7904057A (nl) | 1979-11-27 |
| CH642041A5 (de) | 1984-03-30 |
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