CH649979A5 - Verfahren zur herstellung eines 1,1-dihalogen-4-methyl-1,3-pentadiens. - Google Patents

Verfahren zur herstellung eines 1,1-dihalogen-4-methyl-1,3-pentadiens. Download PDF

Info

Publication number: CH649979A5
Authority: CH; Switzerland
Prior art keywords: methyl; alkyl; methylpentane; pentadiene; mol
Prior art date: 1979-09-24

Application number

CH7152/80A

Other languages

German (de)

English (en)

Inventor

Alexander Mihailovski

Jeffrey Dean Robbins

Raymond Augustus Simone

Original Assignee

Stauffer Chemical Co

Priority date (The priority date 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 date listed.)

1979-09-24

Filing date

1980-09-24

Publication date

1985-06-28

1980-09-24 Application filed by Stauffer Chemical Co filed Critical Stauffer Chemical Co

1985-06-28 Publication of CH649979A5 publication Critical patent/CH649979A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 2
238000006243 chemical reaction Methods 0.000 claims description 61
238000000034 method Methods 0.000 claims description 61
239000003054 catalyst Substances 0.000 claims description 33
229910000039 hydrogen halide Inorganic materials 0.000 claims description 32
239000012433 hydrogen halide Substances 0.000 claims description 32
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 20
229910052757 nitrogen Inorganic materials 0.000 claims description 19
230000008569 process Effects 0.000 claims description 18
-1 tetraalkylammonium halides Chemical class 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 9
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 8
150000001408 amides Chemical class 0.000 claims description 8
230000003197 catalytic effect Effects 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 7
150000004820 halides Chemical class 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
229910017053 inorganic salt Inorganic materials 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
239000002585 base Substances 0.000 claims description 4
150000003950 cyclic amides Chemical class 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
150000003512 tertiary amines Chemical class 0.000 claims description 4
229910001615 alkaline earth metal halide Inorganic materials 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
241000267722 Genidens Species 0.000 claims 1
239000000047 product Substances 0.000 description 44
150000001993 dienes Chemical class 0.000 description 38
150000001875 compounds Chemical class 0.000 description 25
239000011541 reaction mixture Substances 0.000 description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
238000010438 heat treatment Methods 0.000 description 20
238000010992 reflux Methods 0.000 description 17
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 15
150000001336 alkenes Chemical class 0.000 description 15
239000000203 mixture Substances 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
238000004458 analytical method Methods 0.000 description 10
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 10
NEPBEPYINQHTKZ-UHFFFAOYSA-N 1,1,1,3-tetrachloro-4-methylpentane Chemical compound CC(C)C(Cl)CC(Cl)(Cl)Cl NEPBEPYINQHTKZ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000007788 liquid Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
230000035484 reaction time Effects 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
150000001335 aliphatic alkanes Chemical class 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
239000007789 gas Substances 0.000 description 5
XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 5
239000004215 Carbon black (E152) Substances 0.000 description 4
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
235000011089 carbon dioxide Nutrition 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
230000008030 elimination Effects 0.000 description 4
238000003379 elimination reaction Methods 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
238000011065 in-situ storage Methods 0.000 description 4
239000002243 precursor Substances 0.000 description 4
PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000010924 continuous production Methods 0.000 description 3
230000018044 dehydration Effects 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
238000006704 dehydrohalogenation reaction Methods 0.000 description 3
239000002917 insecticide Substances 0.000 description 3
230000009467 reduction Effects 0.000 description 3
230000004044 response Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 2
KDISMIMTGUMORD-UHFFFAOYSA-N 1-acetylpiperidine Chemical compound CC(=O)N1CCCCC1 KDISMIMTGUMORD-UHFFFAOYSA-N 0.000 description 2
YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 2
DLOXDLMFKIZCRH-UHFFFAOYSA-N 5,5,5-trichloropent-1-en-1-ol Chemical compound ClC(CCC=CO)(Cl)Cl DLOXDLMFKIZCRH-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
229910001508 alkali metal halide Inorganic materials 0.000 description 2
150000008045 alkali metal halides Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
238000004821 distillation Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000012467 final product Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 2
LHTVMBMETNGEAN-UHFFFAOYSA-N pent-1-en-1-ol Chemical class CCCC=CO LHTVMBMETNGEAN-UHFFFAOYSA-N 0.000 description 2
230000000737 periodic effect Effects 0.000 description 2
239000012071 phase Substances 0.000 description 2
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
239000002728 pyrethroid Substances 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
239000000126 substance Substances 0.000 description 2
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
KLBOFRLEHJAXIU-UHFFFAOYSA-N tributylazanium;chloride Chemical compound Cl.CCCCN(CCCC)CCCC KLBOFRLEHJAXIU-UHFFFAOYSA-N 0.000 description 2
239000011701 zinc Substances 0.000 description 2
BOGRNZQRTNVZCZ-UHFFFAOYSA-N 1,2-dimethyl-butadiene Natural products CC=C(C)C=C BOGRNZQRTNVZCZ-UHFFFAOYSA-N 0.000 description 1
ZEZOIRFVLXEXBC-UHFFFAOYSA-N 1-ethylazetidine Chemical compound CCN1CCC1 ZEZOIRFVLXEXBC-UHFFFAOYSA-N 0.000 description 1
LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 description 1
VTDIWMPYBAVEDY-UHFFFAOYSA-N 1-propylpiperidine Chemical compound CCCN1CCCCC1 VTDIWMPYBAVEDY-UHFFFAOYSA-N 0.000 description 1
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
XALHICXNSREUAV-UHFFFAOYSA-N 2-oxopyrrolidine-1-carbaldehyde Chemical compound O=CN1CCCC1=O XALHICXNSREUAV-UHFFFAOYSA-N 0.000 description 1
XPMMAKUHNMSONL-UHFFFAOYSA-N 6-methylpiperidin-2-one Chemical compound CC1CCCC(=O)N1 XPMMAKUHNMSONL-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241000238631 Hexapoda Species 0.000 description 1
238000004566 IR spectroscopy Methods 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
239000002841 Lewis acid Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
SPUNPYVHONNUPH-UHFFFAOYSA-N N-methyl-N-propylpentanamide Chemical compound C(CCCC)(=O)N(C)CCC SPUNPYVHONNUPH-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
BKVIQODYSREJQH-UHFFFAOYSA-M [Br-].CC(C)=C[Mg+] Chemical compound [Br-].CC(C)=C[Mg+] BKVIQODYSREJQH-UHFFFAOYSA-M 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910001413 alkali metal ion Inorganic materials 0.000 description 1
229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
229910001626 barium chloride Inorganic materials 0.000 description 1
WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
APPOKADJQUIAHP-UHFFFAOYSA-N hexa-2,4-diene Chemical compound CC=CC=CC APPOKADJQUIAHP-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000010952 in-situ formation Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000003999 initiator Substances 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 description 1
OAERLTPBKQBWHJ-UHFFFAOYSA-N n,n-dimethylhexanamide Chemical compound CCCCCC(=O)N(C)C OAERLTPBKQBWHJ-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
SSJOFYZNKQFVBK-UHFFFAOYSA-N n-ethyl-n-methylbutanamide Chemical compound CCCC(=O)N(C)CC SSJOFYZNKQFVBK-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
VWBWQOUWDOULQN-UHFFFAOYSA-N nmp n-methylpyrrolidone Chemical compound CN1CCCC1=O.CN1CCCC1=O VWBWQOUWDOULQN-UHFFFAOYSA-N 0.000 description 1
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH7152/80A 1979-09-24 1980-09-24 Verfahren zur herstellung eines 1,1-dihalogen-4-methyl-1,3-pentadiens. CH649979A5 (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US7812779A	1979-09-24	1979-09-24
US7812679A	1979-09-24	1979-09-24
US13961580A	1980-04-11	1980-04-11

Publications (1)

Publication Number	Publication Date
CH649979A5 true CH649979A5 (de)	1985-06-28

Family

ID=27373215

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH7152/80A CH649979A5 (de)	1979-09-24	1980-09-24	Verfahren zur herstellung eines 1,1-dihalogen-4-methyl-1,3-pentadiens.

Country Status (12)

Country	Link
AT (1)	AT375332B (da)
BE (1)	BE885355A (da)
BR (1)	BR8006075A (da)
CA (1)	CA1147350A (da)
CH (1)	CH649979A5 (da)
DE (1)	DE3035847A1 (da)
DK (1)	DK403380A (da)
ES (1)	ES8106688A1 (da)
FR (1)	FR2465701B1 (da)
GB (1)	GB2062623B (da)
IL (1)	IL61119A (da)
NL (1)	NL8005323A (da)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1536685A (en) *	1975-06-02	1978-12-20	Shell Int Research	Process for the preparation of 1,1-dihalo-1,3-dienes
DE3061593D1 (en) *	1979-07-13	1983-02-17	Ici Plc	Process for the preparation of halogenated hydrocarbons

1980
- 1980-09-22 FR FR8020321A patent/FR2465701B1/fr not_active Expired
- 1980-09-22 GB GB8030505A patent/GB2062623B/en not_active Expired
- 1980-09-23 DE DE19803035847 patent/DE3035847A1/de not_active Withdrawn
- 1980-09-23 AT AT0474880A patent/AT375332B/de not_active IP Right Cessation
- 1980-09-23 BR BR8006075A patent/BR8006075A/pt unknown
- 1980-09-23 IL IL61119A patent/IL61119A/xx unknown
- 1980-09-24 DK DK403380A patent/DK403380A/da not_active Application Discontinuation
- 1980-09-24 ES ES80495300A patent/ES8106688A1/es not_active Expired
- 1980-09-24 NL NL8005323A patent/NL8005323A/nl not_active Application Discontinuation
- 1980-09-24 CH CH7152/80A patent/CH649979A5/de not_active IP Right Cessation
- 1980-09-24 BE BE2/58763A patent/BE885355A/nl not_active IP Right Cessation
1981
- 1981-02-09 CA CA000370443A patent/CA1147350A/en not_active Expired

Also Published As

Publication number	Publication date
ES495300A0 (es)	1981-09-01
IL61119A (en)	1985-02-28
DE3035847A1 (de)	1981-04-16
ATA474880A (de)	1983-12-15
FR2465701B1 (fr)	1985-04-05
DK403380A (da)	1981-03-25
IL61119A0 (en)	1980-11-30
BE885355A (nl)	1981-03-24
ES8106688A1 (es)	1981-09-01
GB2062623A (en)	1981-05-28
FR2465701A1 (fr)	1981-03-27
GB2062623B (en)	1983-06-29
BR8006075A (pt)	1981-04-07
NL8005323A (nl)	1981-03-26
AT375332B (de)	1984-07-25
CA1147350A (en)	1983-05-31

Legal Events

Date	Code	Title	Description
1986-05-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE3735467A1 (de)	1989-05-03	Verfahren zur herstellung von fluorierten c(pfeil abwaerts)4(pfeil abwaerts)- bis c(pfeil abwaerts)6(pfeil abwaerts)-kohlenwasserstoffen und neue cyclische fluorierte kohlenwasserstoffe, sowie die verwendung von fluorierten c(pfeil abwaerts)4(pfeil abwaerts)- bis c(pfeil abwaerts)6(pfeil abwaerts)-kohlenwasserstoffen als treibgas und arbeitsfluessigkeit fuer waermepumpensysteme
CH639357A5 (de)	1983-11-15	Verfahren zur herstellung von hexamethyltetrahydronaphthalin.
DE2607294C2 (de)	1985-12-05	Verfahren zur Herstellung von 2-Amino-1-butanol
DE2318941C2 (de)	1982-09-16	Verfahren zur Herstellung von Polyfluoralkylestern und/oder -alkoholen
EP0012224B1 (de)	1989-01-18	Verfahren zur Herstellung von Riechstoffgemischen
CH647500A5 (de)	1985-01-31	Verfahren zur herstellung von 2',6'-dialkyl-n-(alkoxymethyl)-2-chloracetaniliden.
DE69604327T2 (de)	2000-04-13	Herstellung von polyalkylierten Cyclopentadienen aus Isobornylcarboxylaten
CH649979A5 (de)	1985-06-28	Verfahren zur herstellung eines 1,1-dihalogen-4-methyl-1,3-pentadiens.
DE3941472C1 (da)	1991-02-21
EP0220412B1 (de)	1991-04-17	Verfahren zur Herstellung von reinen, chlorfreien Cyclopropancarbonsäureestern
EP0037548A2 (de)	1981-10-14	Verfahren zur Herstellung von 2,2,6,6-Tetramethylpiperidon-4
DE1543083B1 (de)	1971-07-01	Verfahren zur Herstellung von Terpenverbindungen
DE2824976C2 (de)	1983-12-29	Verfahren zur Herstellung von Cycloalkanoläthern
DE2659597C2 (da)	1987-09-10
DE1203760B (de)	1965-10-28	Verfahren zur Herstellung von Sorbinsaeure-alkylestern
CH663204A5 (de)	1987-11-30	Propannitrilderivate.
DE2345360A1 (de)	1974-03-14	Verfahren zur herstellung von transchrysanthemummonocarbonsaeure und deren alkylestern
EP0732316A1 (de)	1996-09-18	Verfahren zur katalytischen Dehydrohalogenierung von halogenierten Kohlenwasserstoffen
DE2400326C2 (de)	1983-10-27	Verfahren zur Herstellung höherer Alkohole
DE69404920T2 (de)	1998-01-08	Verfahren zur Herstellung von Cyclobutanonen
DE2921220C2 (de)	1981-10-08	Verfahren zur Herstellung von 2.3.4.4.-Tetrachlor-3-butensäurealkylestern
DE2265299C3 (de)	1981-01-08	Verfahren zur Herstellung von 1,4-Dicyanbutenen
DE69418343T2 (de)	1999-09-09	Herstellung von difluormethan
EP0564979B1 (de)	1996-08-28	Verfahren zur Herstellung von Dixylylpropan
DE3344870C2 (da)	1989-07-13