CA1120047A - Procede d'obtention d'oxyranes a substitution par des halogenoalkyles - Google Patents

Procede d'obtention d'oxyranes a substitution par des halogenoalkyles

Info

Publication number: CA1120047A
Authority: CA; Canada
Prior art keywords: alkyl; substituted; dichloro; dibromo; process according
Prior art date: 1977-07-28
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

Application number

CA000308193A

Other languages

English (en)

Inventor

Gebhard Rauleder

Hermann Seifert

Hubert Kastenhuber

Gunter Prescher

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Evonik Operations GmbH

Original Assignee

Bayer AG

Deutsche Gold und Silber Scheideanstalt

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.)

1977-07-28

Filing date

1978-07-26

Publication date

1982-03-16

1978-07-26 Application filed by Bayer AG, Deutsche Gold und Silber Scheideanstalt filed Critical Bayer AG

1982-03-16 Application granted granted Critical

1982-03-16 Publication of CA1120047A publication Critical patent/CA1120047A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 40
150000002924 oxiranes Chemical class 0.000 title claims abstract description 20
238000002360 preparation method Methods 0.000 title claims abstract description 13
238000006243 chemical reaction Methods 0.000 claims abstract description 45
150000001336 alkenes Chemical class 0.000 claims abstract description 28
239000002253 acid Substances 0.000 claims abstract description 27
150000007513 acids Chemical class 0.000 claims abstract description 10
CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 claims description 26
SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 claims description 22
-1 methylene, chloromethylene Chemical group 0.000 claims description 21
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 20
150000004965 peroxy acids Chemical class 0.000 claims description 15
239000011541 reaction mixture Substances 0.000 claims description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
FQDIANVAWVHZIR-OWOJBTEDSA-N trans-1,4-Dichlorobutene Chemical compound ClC\C=C\CCl FQDIANVAWVHZIR-OWOJBTEDSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
150000005673 monoalkenes Chemical class 0.000 claims description 9
RMXLHIUHKIVPAB-OWOJBTEDSA-N (e)-1,4-dibromobut-2-ene Chemical compound BrC\C=C\CBr RMXLHIUHKIVPAB-OWOJBTEDSA-N 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
XVEASTGLHPVZNA-UHFFFAOYSA-N 3,4-dichlorobut-1-ene Chemical compound ClCC(Cl)C=C XVEASTGLHPVZNA-UHFFFAOYSA-N 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
238000000605 extraction Methods 0.000 claims description 3
KFUSEUYYWQURPO-UHFFFAOYSA-N 1,2-dichloroethene Chemical group ClC=CCl KFUSEUYYWQURPO-UHFFFAOYSA-N 0.000 claims description 2
239000002904 solvent Substances 0.000 abstract description 4
239000004215 Carbon black (E152) Substances 0.000 abstract 1
229930195733 hydrocarbon Natural products 0.000 abstract 1
150000002430 hydrocarbons Chemical class 0.000 abstract 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
238000006735 epoxidation reaction Methods 0.000 description 9
239000000203 mixture Substances 0.000 description 9
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 8
229960002163 hydrogen peroxide Drugs 0.000 description 7
229910052500 inorganic mineral Inorganic materials 0.000 description 7
239000011707 mineral Substances 0.000 description 7
235000019260 propionic acid Nutrition 0.000 description 7
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
230000000875 corresponding effect Effects 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
VUSYFNXNYLAECV-UHFFFAOYSA-N 2,3-bis(chloromethyl)oxirane Chemical compound ClCC1OC1CCl VUSYFNXNYLAECV-UHFFFAOYSA-N 0.000 description 3
UKXROSORAUTSSH-UHFFFAOYSA-N 2-(1,2-dichloroethyl)oxirane Chemical compound ClCC(Cl)C1CO1 UKXROSORAUTSSH-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
239000011521 glass Substances 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 3
ZTXLEHGBELXWCK-SNAWJCMRSA-N (e)-2-bromohex-3-ene Chemical compound CC\C=C\C(C)Br ZTXLEHGBELXWCK-SNAWJCMRSA-N 0.000 description 2
LIPODSDLKCMVON-ONEGZZNKSA-N (e)-4-bromopent-2-ene Chemical compound C\C=C\C(C)Br LIPODSDLKCMVON-ONEGZZNKSA-N 0.000 description 2
FKKCIOTUMHPTSB-ONEGZZNKSA-N (e)-4-chloropent-2-ene Chemical compound C\C=C\C(C)Cl FKKCIOTUMHPTSB-ONEGZZNKSA-N 0.000 description 2
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 description 2
WBCSJABQCRFUCP-UHFFFAOYSA-N 1,2-dichloroheptane Chemical compound CCCCCC(Cl)CCl WBCSJABQCRFUCP-UHFFFAOYSA-N 0.000 description 2
ZHFXSKJYCSWRJA-UHFFFAOYSA-N 1,2-dichlorohexane Chemical compound CCCCC(Cl)CCl ZHFXSKJYCSWRJA-UHFFFAOYSA-N 0.000 description 2
LYVLPCUIYWOEBI-UHFFFAOYSA-N 1,2-dichlorooctane Chemical compound CCCCCCC(Cl)CCl LYVLPCUIYWOEBI-UHFFFAOYSA-N 0.000 description 2
IVNXCZYKOHEIGF-UHFFFAOYSA-N 1,4-dibromohex-2-ene Chemical compound CCC(Br)C=CCBr IVNXCZYKOHEIGF-UHFFFAOYSA-N 0.000 description 2
JDFBGPUSKMHVBN-UHFFFAOYSA-N 1,4-dichlorohex-2-ene Chemical compound CCC(Cl)C=CCCl JDFBGPUSKMHVBN-UHFFFAOYSA-N 0.000 description 2
SGEUYXUPUOLFHQ-UHFFFAOYSA-N 1-bromohex-2-ene Chemical compound CCCC=CCBr SGEUYXUPUOLFHQ-UHFFFAOYSA-N 0.000 description 2
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
UQLCVPMPXJDZPX-UHFFFAOYSA-N 2,5-dibromohex-3-ene Chemical compound CC(Br)C=CC(C)Br UQLCVPMPXJDZPX-UHFFFAOYSA-N 0.000 description 2
ZBQFRDTZYRRHRU-UHFFFAOYSA-N 3,4-dibromobut-1-ene Chemical compound BrCC(Br)C=C ZBQFRDTZYRRHRU-UHFFFAOYSA-N 0.000 description 2
JQGARBLJULSUFA-UHFFFAOYSA-N 3,4-dichlorohex-1-ene Chemical compound CCC(Cl)C(Cl)C=C JQGARBLJULSUFA-UHFFFAOYSA-N 0.000 description 2
UICQHIPTNUWGAT-UHFFFAOYSA-N 3,4-dichloropent-1-ene Chemical compound CC(Cl)C(Cl)C=C UICQHIPTNUWGAT-UHFFFAOYSA-N 0.000 description 2
ZZLDYZLPDLYQAC-UHFFFAOYSA-N 3,6-dibromocyclohexene Chemical compound BrC1CCC(Br)C=C1 ZZLDYZLPDLYQAC-UHFFFAOYSA-N 0.000 description 2
BDHXXBPPYQRWMC-UHFFFAOYSA-N 3-bromo-2-(bromomethyl)prop-1-ene Chemical compound BrCC(=C)CBr BDHXXBPPYQRWMC-UHFFFAOYSA-N 0.000 description 2
USEGQJLHQSTGHW-UHFFFAOYSA-N 3-bromo-2-methylprop-1-ene Chemical compound CC(=C)CBr USEGQJLHQSTGHW-UHFFFAOYSA-N 0.000 description 2
XOTGLEGIDHZTIM-UHFFFAOYSA-N 3-bromobut-1-ene Chemical compound CC(Br)C=C XOTGLEGIDHZTIM-UHFFFAOYSA-N 0.000 description 2
XJFZOSUFGSANIF-UHFFFAOYSA-N 3-chloro-2-(chloromethyl)prop-1-ene Chemical compound ClCC(=C)CCl XJFZOSUFGSANIF-UHFFFAOYSA-N 0.000 description 2
VZGLVCFVUREVDP-UHFFFAOYSA-N 3-chlorobut-1-ene Chemical compound CC(Cl)C=C VZGLVCFVUREVDP-UHFFFAOYSA-N 0.000 description 2
WSVIAQNBRKPWKO-UHFFFAOYSA-N 4,5-dichloropent-2-ene Chemical compound CC=CC(Cl)CCl WSVIAQNBRKPWKO-UHFFFAOYSA-N 0.000 description 2
RABIGFRACNMIOB-UHFFFAOYSA-N 4,7-dibromoundec-5-ene Chemical compound BrC(CCCC)C=CC(CCC)Br RABIGFRACNMIOB-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
238000006887 Ullmann reaction Methods 0.000 description 2
DQGRFSFYQIYMHB-UHFFFAOYSA-N acetaldehyde;ethaneperoxoic acid Chemical compound CC=O.CC(=O)OO DQGRFSFYQIYMHB-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
YTKRILODNOEEPX-NSCUHMNNSA-N crotyl chloride Chemical compound C\C=C\CCl YTKRILODNOEEPX-NSCUHMNNSA-N 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
229910001385 heavy metal Inorganic materials 0.000 description 2
239000000463 material Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000009257 reactivity Effects 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
239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 2
KFTRXTSNTQSGNE-UHFFFAOYSA-N (1-methylpyrazol-4-yl)methanamine Chemical compound CN1C=C(CN)C=N1 KFTRXTSNTQSGNE-UHFFFAOYSA-N 0.000 description 1
WLTSXAIICPDFKI-FNORWQNLSA-N (E)-3-dodecene Chemical compound CCCCCCCC\C=C\CC WLTSXAIICPDFKI-FNORWQNLSA-N 0.000 description 1
UVMIILJLDZZDBA-VQHVLOKHSA-N (E)-6-chlorodec-4-ene Chemical compound CCCCC(Cl)\C=C\CCC UVMIILJLDZZDBA-VQHVLOKHSA-N 0.000 description 1
ULIUKQDFGSZIRQ-SOFGYWHQSA-N (e)-6-chloronon-4-ene Chemical compound CCC\C=C\C(Cl)CCC ULIUKQDFGSZIRQ-SOFGYWHQSA-N 0.000 description 1
PHCKFVVLVZFFLU-VQHVLOKHSA-N (e)-dodec-4-ene Chemical compound CCCCCCC\C=C\CCC PHCKFVVLVZFFLU-VQHVLOKHSA-N 0.000 description 1
QMMOXUPEWRXHJS-HYXAFXHYSA-N (z)-pent-2-ene Chemical compound CC\C=C/C QMMOXUPEWRXHJS-HYXAFXHYSA-N 0.000 description 1
IFTGEZOPUAJVMG-UHFFFAOYSA-N 1,1-dibromobut-1-ene Chemical compound CCC=C(Br)Br IFTGEZOPUAJVMG-UHFFFAOYSA-N 0.000 description 1
IXZVKECRTHXEEW-UHFFFAOYSA-N 1,2,3,4-tetrachlorobutane Chemical compound ClCC(Cl)C(Cl)CCl IXZVKECRTHXEEW-UHFFFAOYSA-N 0.000 description 1
XITTYWHEFIYYHQ-UHFFFAOYSA-N 1,2,3,4-tetrachloroheptane Chemical compound CCCC(Cl)C(Cl)C(Cl)CCl XITTYWHEFIYYHQ-UHFFFAOYSA-N 0.000 description 1
RESQRQVUNRBEQB-UHFFFAOYSA-N 1,2,3,4-tetrachlorooctane Chemical compound CCCCC(Cl)C(Cl)C(Cl)CCl RESQRQVUNRBEQB-UHFFFAOYSA-N 0.000 description 1
PQBOTZNYFQWRHU-UHFFFAOYSA-N 1,2-dichlorobutane Chemical compound CCC(Cl)CCl PQBOTZNYFQWRHU-UHFFFAOYSA-N 0.000 description 1
PPLBPDUKNRCHGG-UHFFFAOYSA-N 1,2-dichloropentane Chemical compound CCCC(Cl)CCl PPLBPDUKNRCHGG-UHFFFAOYSA-N 0.000 description 1
KNKRKFALVUDBJE-VMIGTVKRSA-N 1,2-dichloropropane Chemical group [13CH3][13CH](Cl)[13CH2]Cl KNKRKFALVUDBJE-VMIGTVKRSA-N 0.000 description 1
QBGVARBIQGHVKR-UHFFFAOYSA-N 1,3-dichlorobutane Chemical compound CC(Cl)CCCl QBGVARBIQGHVKR-UHFFFAOYSA-N 0.000 description 1
DDZTTWQJEJYUKA-UHFFFAOYSA-N 1,4-dibromodec-2-ene Chemical compound CCCCCCC(Br)C=CCBr DDZTTWQJEJYUKA-UHFFFAOYSA-N 0.000 description 1
JICFWWNKYPMMJY-UHFFFAOYSA-N 1,4-dibromonon-2-ene Chemical compound BrCC=CC(CCCCC)Br JICFWWNKYPMMJY-UHFFFAOYSA-N 0.000 description 1
HZGSTPGRGVBIHO-UHFFFAOYSA-N 1,4-dibromooct-2-ene Chemical compound CCCCC(Br)C=CCBr HZGSTPGRGVBIHO-UHFFFAOYSA-N 0.000 description 1
TTWRDHJRYYHEKD-UHFFFAOYSA-N 1,4-dibromopent-2-ene Chemical compound CC(Br)C=CCBr TTWRDHJRYYHEKD-UHFFFAOYSA-N 0.000 description 1
KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 description 1
VBJCBKGMCSNOQH-UHFFFAOYSA-N 1,4-dichlorodec-2-ene Chemical compound ClCC=CC(CCCCCC)Cl VBJCBKGMCSNOQH-UHFFFAOYSA-N 0.000 description 1
HJVFQQWQWHUHLS-UHFFFAOYSA-N 1,4-dichlorohept-2-ene Chemical compound ClCC=CC(CCC)Cl HJVFQQWQWHUHLS-UHFFFAOYSA-N 0.000 description 1
XMBILWBZDHDMFX-UHFFFAOYSA-N 1,4-dichloronon-2-ene Chemical compound ClCC=CC(CCCCC)Cl XMBILWBZDHDMFX-UHFFFAOYSA-N 0.000 description 1
OKKSGCZXXKVVCB-UHFFFAOYSA-N 1,4-dichlorooct-2-ene Chemical compound ClCC=CC(CCCC)Cl OKKSGCZXXKVVCB-UHFFFAOYSA-N 0.000 description 1
PRDDYLMTZYBCDV-UHFFFAOYSA-N 1,4-dichloropent-2-ene Chemical compound CC(Cl)C=CCCl PRDDYLMTZYBCDV-UHFFFAOYSA-N 0.000 description 1
LBKDGROORAKTLC-UHFFFAOYSA-N 1,5-dichloropentane Chemical compound ClCCCCCCl LBKDGROORAKTLC-UHFFFAOYSA-N 0.000 description 1
OVISMSJCKCDOPU-UHFFFAOYSA-N 1,6-dichlorohexane Chemical compound ClCCCCCCCl OVISMSJCKCDOPU-UHFFFAOYSA-N 0.000 description 1
OLFPNOLTKBHRSO-UHFFFAOYSA-N 1-bromodec-3-ene Chemical compound CCCCCCC=CCCBr OLFPNOLTKBHRSO-UHFFFAOYSA-N 0.000 description 1
LEFZUVORTWHIMT-UHFFFAOYSA-N 1-bromonon-2-ene Chemical compound CCCCCCC=CCBr LEFZUVORTWHIMT-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
YTKRILODNOEEPX-UHFFFAOYSA-N 1-chlorobut-2-ene Chemical compound CC=CCCl YTKRILODNOEEPX-UHFFFAOYSA-N 0.000 description 1
KYRQIMSYGJMMRU-UHFFFAOYSA-N 1-chlorodec-3-ene Chemical compound CCCCCCC=CCCCl KYRQIMSYGJMMRU-UHFFFAOYSA-N 0.000 description 1
SPEHXBXRRMYRDX-UHFFFAOYSA-N 1-chlorododec-3-ene Chemical compound CCCCCCCCC=CCCCl SPEHXBXRRMYRDX-UHFFFAOYSA-N 0.000 description 1
JCUPTNHYJZXKIH-UHFFFAOYSA-N 1-chlorododec-5-ene Chemical compound CCCCCCC=CCCCCCl JCUPTNHYJZXKIH-UHFFFAOYSA-N 0.000 description 1
DZMDPHNGKBEVRE-UHFFFAOYSA-N 1-chloroheptane Chemical compound CCCCCCCCl DZMDPHNGKBEVRE-UHFFFAOYSA-N 0.000 description 1
MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 description 1
UPJCRKZUCADENN-UHFFFAOYSA-N 1-chloropent-2-ene Chemical compound CCC=CCCl UPJCRKZUCADENN-UHFFFAOYSA-N 0.000 description 1
SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
RMISVOPUIFJTEO-UHFFFAOYSA-N 2,3-dichlorobutane Chemical compound CC(Cl)C(C)Cl RMISVOPUIFJTEO-UHFFFAOYSA-N 0.000 description 1
KOSQLOKDRQRHHR-UHFFFAOYSA-N 2,5-dibromododec-3-ene Chemical compound BrC(C)C=CC(CCCCCCC)Br KOSQLOKDRQRHHR-UHFFFAOYSA-N 0.000 description 1
JMXOCABVBADJGL-UHFFFAOYSA-N 2,5-dibromonon-3-ene Chemical compound BrC(C)C=CC(CCCC)Br JMXOCABVBADJGL-UHFFFAOYSA-N 0.000 description 1
VUPJBPHTPOZSPX-UHFFFAOYSA-N 2,5-dibromooct-3-ene Chemical compound CCCC(Br)C=CC(C)Br VUPJBPHTPOZSPX-UHFFFAOYSA-N 0.000 description 1
JNSPBVJVHSIYJA-UHFFFAOYSA-N 2,5-dibromoundec-3-ene Chemical compound BrC(C)C=CC(CCCCCC)Br JNSPBVJVHSIYJA-UHFFFAOYSA-N 0.000 description 1
GHRUELLVRVXPEW-UHFFFAOYSA-N 2,5-dichlorohex-3-ene Chemical compound CC(Cl)C=CC(C)Cl GHRUELLVRVXPEW-UHFFFAOYSA-N 0.000 description 1
ZOEKCESTXHOYHU-UHFFFAOYSA-N 2,5-dichloronon-3-ene Chemical compound ClC(C)C=CC(CCCC)Cl ZOEKCESTXHOYHU-UHFFFAOYSA-N 0.000 description 1
FAPHKEWVOARSSG-UHFFFAOYSA-N 2,5-dichloroundec-3-ene Chemical compound ClC(C)C=CC(CCCCCC)Cl FAPHKEWVOARSSG-UHFFFAOYSA-N 0.000 description 1
JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
XPLXPLDYYNFTCE-UHFFFAOYSA-N 2-bromodec-3-ene Chemical compound BrC(C)C=CCCCCCC XPLXPLDYYNFTCE-UHFFFAOYSA-N 0.000 description 1
RCGPJWGMDKZPMQ-UHFFFAOYSA-N 2-bromododec-3-ene Chemical compound BrC(C)C=CCCCCCCCC RCGPJWGMDKZPMQ-UHFFFAOYSA-N 0.000 description 1
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QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
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239000004115 Sodium Silicate Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
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150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
LBAYFEDWGHXMSM-UHFFFAOYSA-N butaneperoxoic acid Chemical compound CCCC(=O)OO LBAYFEDWGHXMSM-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
LDOZEEFSUYHNPM-UHFFFAOYSA-N chlorocyclooctane Chemical compound ClC1CCCCCCC1 LDOZEEFSUYHNPM-UHFFFAOYSA-N 0.000 description 1
NDTCXABJQNJPCF-UHFFFAOYSA-N chlorocyclopentane Chemical compound ClC1CCCC1 NDTCXABJQNJPCF-UHFFFAOYSA-N 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
230000009918 complex formation Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000004913 cyclooctene Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000006704 dehydrohalogenation reaction Methods 0.000 description 1
125000000950 dibromo group Chemical group Br* 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
MVPBBROXZRXGSO-UHFFFAOYSA-L disodium;dimethoxyphosphoryl phosphate Chemical compound [Na+].[Na+].COP(=O)(OC)OP([O-])([O-])=O MVPBBROXZRXGSO-UHFFFAOYSA-L 0.000 description 1
229940069096 dodecene Drugs 0.000 description 1
XUFQPHANEAPEMJ-UHFFFAOYSA-N famotidine Chemical compound NC(N)=NC1=NC(CSCCC(N)=NS(N)(=O)=O)=CS1 XUFQPHANEAPEMJ-UHFFFAOYSA-N 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 1
AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
230000036647 reaction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
229940048086 sodium pyrophosphate Drugs 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
229910052911 sodium silicate Inorganic materials 0.000 description 1
235000019794 sodium silicate Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
- 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
- C07C17/02—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated hydrocarbons
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof

Landscapes

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

CA000308193A 1977-07-28 1978-07-26 Procede d'obtention d'oxyranes a substitution par des halogenoalkyles Expired CA1120047A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19772734085 DE2734085A1 (de)	1977-07-28	1977-07-28	Verfahren zur herstellung von halogenalkylsubstituierten oxiranen
DEP2734085.8		1977-07-28

Publications (1)

Publication Number	Publication Date
CA1120047A true CA1120047A (fr)	1982-03-16

Family

ID=6015052

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000308193A Expired CA1120047A (fr)	1977-07-28	1978-07-26	Procede d'obtention d'oxyranes a substitution par des halogenoalkyles

Country Status (6)

Country	Link
EP (1)	EP0000554B1 (fr)
JP (1)	JPS5424806A (fr)
AT (1)	AT358057B (fr)
CA (1)	CA1120047A (fr)
DD (1)	DD138067A5 (fr)
DE (2)	DE2734085A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2456096A1 (fr) *	1979-05-10	1980-12-05	Solvay	Procede pour la fabrication d'oxydes d'olefines
DE102005019296A1 (de)	2005-04-26	2006-11-09	Deutsche Exide Gmbh	Entgasungsventil für Säurebatterien
DE102021123420A1 (de)	2020-09-11	2022-03-17	Illinois Tool Works Inc.	Notentgasungsventil
DE102023106792A1 (de)	2022-04-11	2023-10-12	Illinois Tool Works Inc.	Notentgasungsventilvorrichtung

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1535313A (en) *	1975-02-04	1978-12-13	Interox Chemicals Ltd	Production of peracids and of epoxides
BE860029A (fr) *	1976-10-26	1978-04-24	Propylox Sa	Procede pour l'epoxydation d'olefines
GB1584355A (en) *	1976-10-26	1981-02-11	Propylox Sa	Epoxidation

1977
- 1977-07-28 DE DE19772734085 patent/DE2734085A1/de not_active Withdrawn
1978
- 1978-07-20 DE DE7878100456T patent/DE2861619D1/de not_active Expired
- 1978-07-20 EP EP78100456A patent/EP0000554B1/fr not_active Expired
- 1978-07-26 JP JP9056778A patent/JPS5424806A/ja active Pending
- 1978-07-26 AT AT544578A patent/AT358057B/de not_active IP Right Cessation
- 1978-07-26 DD DD78206957A patent/DD138067A5/xx unknown
- 1978-07-26 CA CA000308193A patent/CA1120047A/fr not_active Expired

Also Published As

Publication number	Publication date
AT358057B (de)	1980-08-25
EP0000554B1 (fr)	1982-02-10
EP0000554A1 (fr)	1979-02-07
DE2734085A1 (de)	1979-02-22
DE2861619D1 (en)	1982-03-18
ATA544578A (de)	1980-01-15
JPS5424806A (en)	1979-02-24
DD138067A5 (de)	1979-10-10

Legal Events

Date	Code	Title	Description
1999-03-16	MKEX	Expiry

Publication	Publication Date	Title
US5166372A (en)	1992-11-24	Epoxidation process
PL197538B1 (pl)	2008-04-30	Oczyszczony produkt epichlorohydryny oraz sposób wytwarzania produktu na bazie epichlorohydryny
GB1585012A (en)	1981-02-18	Process for the epoxidation of olefins
Trost et al.	1991	A convenient synthesis of. gamma.-hydroxy. alpha.,. beta.-unsaturated sulfones
CA1120047A (fr)	1982-03-16	Procede d'obtention d'oxyranes a substitution par des halogenoalkyles
Sato et al.	1985	Palladium-catalysed oxidation of alcohols with carbon tetrachloride, formation of 4, 4, 4-trichloro ketones from allylic alcohols and carbon tetrachlorid
Tsuji et al.	1982	A palladium catalyzed conversion of halohydrins to ketones
CA1120048A (fr)	1982-03-16	Procede d'obtention d'oxyranes a substitution par des halogenoalkyles
US4344887A (en)	1982-08-17	Method for epoxidizing olefins
US3232957A (en)	1966-02-01	Process for the preparation of olefin oxides
US3290336A (en)	1966-12-06	Epoxide production
US3316291A (en)	1967-04-25	Unsaturated esters of halohydrins
US3419579A (en)	1968-12-31	Synthesis of 2,3-dihydro-2,2-dimethyl-7-benzofuranol
Uchiyama et al.	1985	Acyclic stereoselection using relative 1, 2-asymmetric induction. Selective synthesis of (+)-blastmycinone.
EP0019804B1 (fr)	1983-04-13	Bromuration de la chaîne latérale de m-phénoxytoluène
US4562274A (en)	1985-12-31	Process for the preparation and isolation of polyglycidyl compounds
Metzger et al.	1997	Radical Additions of Alkyl 2‐Haloalkanoates and 2‐Haloalkanenitriles to Alkenes Initiated by Electron Transfer from Copper in Solvent‐Free Systems
EP0008112A1 (fr)	1980-02-20	Procédé pour la préparation d'esters glycidiques d'acides aromatiques polycarboxyliques
US3538124A (en)	1970-11-03	Method for the production of 3,4-epoxy-2-methyl-1-butene
US4212809A (en)	1980-07-15	Process for the preparation of 5-(oxiranylmethyl)-1,3-benzodioxole
US4120877A (en)	1978-10-17	Oxidation of olefins to oxirane compounds with periodate compounds
US4389529A (en)	1983-06-21	Method for epoxidizing olefins
US4242285A (en)	1980-12-30	Novel 2,6-dinitrophenyl selenium compounds and their use as epoxidation catalysts
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JP2012131732A (ja)	2012-07-12	ジクロロエポキシブタンの製造方法