BE598169A - - Google Patents
Info
- Publication number
- BE598169A BE598169A BE598169DA BE598169A BE 598169 A BE598169 A BE 598169A BE 598169D A BE598169D A BE 598169DA BE 598169 A BE598169 A BE 598169A
- Authority
- BE
- Belgium
- Prior art keywords
- halogen
- alkyl
- cycloalkyl
- substituted
- aryl
- Prior art date
Links
- 239000000460 chlorine Substances 0.000 description 20
- 229910052801 chlorine Inorganic materials 0.000 description 19
- 229910052736 halogen Inorganic materials 0.000 description 18
- 150000002367 halogens Chemical class 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- VUSBWOJGUYDBOG-UHFFFAOYSA-N 1,2,3,4,5-pentachloro-5-ethylcyclopenta-1,3-diene Chemical compound CCC1(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl VUSBWOJGUYDBOG-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 230000026030 halogenation Effects 0.000 description 3
- 238000005658 halogenation reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 150000001941 cyclopentenes Chemical class 0.000 description 2
- -1 for example Chemical group 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BSGFSGBHTAMBAP-UHFFFAOYSA-N (1,2,3,4,5-pentachlorocyclopenta-2,4-dien-1-yl)benzene Chemical compound C1(=CC=CC=C1)C1(C(=C(C(=C1Cl)Cl)Cl)Cl)Cl BSGFSGBHTAMBAP-UHFFFAOYSA-N 0.000 description 1
- MHDVDBORUDNIBB-UHFFFAOYSA-N 1,2,3,3,4,4,5-heptachloro-5-(2-chloroethyl)cyclopentene Chemical compound ClCCC1(C(C(C(=C1Cl)Cl)(Cl)Cl)(Cl)Cl)Cl MHDVDBORUDNIBB-UHFFFAOYSA-N 0.000 description 1
- OSLMEQKWPOBEJZ-UHFFFAOYSA-N 1,2,3,4,5-pentachloro-5-(2-methoxyethyl)cyclopenta-1,3-diene Chemical compound COCCC1(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl OSLMEQKWPOBEJZ-UHFFFAOYSA-N 0.000 description 1
- BQYLVEKTQDSTAZ-UHFFFAOYSA-N 1,2,3,4,5-pentachloro-5-propan-2-ylcyclopenta-1,3-diene Chemical compound CC(C)C1(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl BQYLVEKTQDSTAZ-UHFFFAOYSA-N 0.000 description 1
- FKHSKADADUMFAM-UHFFFAOYSA-N 1,2,3,4,5-pentachloro-5-propylcyclopenta-1,3-diene Chemical compound C(CC)C1(C(=C(C(=C1Cl)Cl)Cl)Cl)Cl FKHSKADADUMFAM-UHFFFAOYSA-N 0.000 description 1
- SPEJYXWMSKCTFT-UHFFFAOYSA-N 1,2,3,4,5-pentachlorocyclopenta-1,3-diene Chemical compound ClC1C(Cl)=C(Cl)C(Cl)=C1Cl SPEJYXWMSKCTFT-UHFFFAOYSA-N 0.000 description 1
- XNDOHPGHNCJWSF-UHFFFAOYSA-N 1,2,3-trichlorocyclopenta-1,3-diene Chemical compound ClC1=C(Cl)C(Cl)=CC1 XNDOHPGHNCJWSF-UHFFFAOYSA-N 0.000 description 1
- NAILWBJNNIXJEK-UHFFFAOYSA-N 1-butyl-2,3,4-trichloro-5,5-difluorocyclopenta-1,3-diene Chemical compound C(CCC)C1=C(C(=C(C1(F)F)Cl)Cl)Cl NAILWBJNNIXJEK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 241001596957 Brama Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CQVHCSDJHYKUAU-UHFFFAOYSA-N CCC(C(C1(Cl)Cl)(Cl)Cl)(C(Cl)=C1Cl)Cl Chemical compound CCC(C(C1(Cl)Cl)(Cl)Cl)(C(Cl)=C1Cl)Cl CQVHCSDJHYKUAU-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 241001343083 Tonna Species 0.000 description 1
- 241000927721 Tritia Species 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012237 artificial material Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 150000008027 tertiary esters Chemical class 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000009489 vacuum treatment Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/04—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE598169A true BE598169A (de) |
Family
ID=192394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE598169D BE598169A (de) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE598169A (de) |
-
0
- BE BE598169D patent/BE598169A/fr unknown
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