CA1120048A - Process for the preparation of halogenoalkyl- substituted oxiranes - Google Patents
Process for the preparation of halogenoalkyl- substituted oxiranesInfo
- Publication number
- CA1120048A CA1120048A CA000308194A CA308194A CA1120048A CA 1120048 A CA1120048 A CA 1120048A CA 000308194 A CA000308194 A CA 000308194A CA 308194 A CA308194 A CA 308194A CA 1120048 A CA1120048 A CA 1120048A
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- substituted
- dichloro
- dibromo
- process according
- 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 title claims abstract description 35
- 230000008569 process Effects 0.000 title claims abstract description 30
- 150000002924 oxiranes Chemical class 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 44
- 239000002253 acid Substances 0.000 claims abstract description 28
- 150000001336 alkenes Chemical class 0.000 claims abstract description 28
- 150000007513 acids Chemical class 0.000 claims abstract description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 44
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 claims description 30
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 claims description 20
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 20
- -1 methylene, chloromethylene Chemical group 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 13
- 150000004965 peroxy acids Chemical class 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- XVEASTGLHPVZNA-UHFFFAOYSA-N 3,4-dichlorobut-1-ene Chemical compound ClCC(Cl)C=C XVEASTGLHPVZNA-UHFFFAOYSA-N 0.000 claims description 6
- 150000005673 monoalkenes Chemical class 0.000 claims description 6
- FQDIANVAWVHZIR-OWOJBTEDSA-N trans-1,4-Dichlorobutene Chemical compound ClC\C=C\CCl FQDIANVAWVHZIR-OWOJBTEDSA-N 0.000 claims description 6
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-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
- 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 claims 1
- 125000003963 dichloro group Chemical group Cl* 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 16
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 8
- 238000006735 epoxidation reaction Methods 0.000 description 8
- 235000019260 propionic acid Nutrition 0.000 description 8
- 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 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 229960002163 hydrogen peroxide Drugs 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RMXLHIUHKIVPAB-OWOJBTEDSA-N (e)-1,4-dibromobut-2-ene Chemical compound BrC\C=C\CBr RMXLHIUHKIVPAB-OWOJBTEDSA-N 0.000 description 4
- VUSYFNXNYLAECV-UHFFFAOYSA-N 2,3-bis(chloromethyl)oxirane Chemical compound ClCC1OC1CCl VUSYFNXNYLAECV-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000000875 corresponding effect Effects 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
- 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
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- AVMHMVJVHYGDOO-NSCUHMNNSA-N (e)-1-bromobut-2-ene Chemical compound C\C=C\CBr AVMHMVJVHYGDOO-NSCUHMNNSA-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
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- RMXLHIUHKIVPAB-UHFFFAOYSA-N 1,4-dibromobut-2-ene Chemical compound BrCC=CCBr RMXLHIUHKIVPAB-UHFFFAOYSA-N 0.000 description 2
- FQDIANVAWVHZIR-UHFFFAOYSA-N 1,4-dichlorobut-2-ene Chemical compound ClCC=CCCl FQDIANVAWVHZIR-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-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
- UKXROSORAUTSSH-UHFFFAOYSA-N 2-(1,2-dichloroethyl)oxirane Chemical compound ClCC(Cl)C1CO1 UKXROSORAUTSSH-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
- UICQHIPTNUWGAT-UHFFFAOYSA-N 3,4-dichloropent-1-ene Chemical compound CC(Cl)C(Cl)C=C UICQHIPTNUWGAT-UHFFFAOYSA-N 0.000 description 2
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-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
- AJKDUJRRWLQXHM-UHFFFAOYSA-N 3-bromocyclohexene Chemical compound BrC1CCCC=C1 AJKDUJRRWLQXHM-UHFFFAOYSA-N 0.000 description 2
- UTVCDGRAYVLNBH-UHFFFAOYSA-N 3-bromohex-1-ene Chemical compound CCCC(Br)C=C UTVCDGRAYVLNBH-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
- LNGQLHZIYFQUIR-UHFFFAOYSA-N 3-chlorocyclohexene Chemical compound ClC1CCCC=C1 LNGQLHZIYFQUIR-UHFFFAOYSA-N 0.000 description 2
- JAVRINALENERJS-UHFFFAOYSA-N 4,5-dibromopent-2-ene Chemical compound CC=CC(Br)CBr JAVRINALENERJS-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-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
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- YTKRILODNOEEPX-NSCUHMNNSA-N crotyl chloride Chemical compound C\C=C\CCl YTKRILODNOEEPX-NSCUHMNNSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229940058172 ethylbenzene Drugs 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UVMIILJLDZZDBA-VQHVLOKHSA-N (E)-6-chlorodec-4-ene Chemical compound CCCCC(Cl)\C=C\CCC UVMIILJLDZZDBA-VQHVLOKHSA-N 0.000 description 1
- FTBPZRNURKMEFD-ONEGZZNKSA-N (e)-1-bromopent-2-ene Chemical compound CC\C=C\CBr FTBPZRNURKMEFD-ONEGZZNKSA-N 0.000 description 1
- YTXXOKPWZPVIFH-SNAWJCMRSA-N (e)-1-chlorohex-2-ene Chemical compound CCC\C=C\CCl YTXXOKPWZPVIFH-SNAWJCMRSA-N 0.000 description 1
- BNALNZBXPXBMTK-BQYQJAHWSA-N (e)-1-chloronon-2-ene Chemical compound CCCCCC\C=C\CCl BNALNZBXPXBMTK-BQYQJAHWSA-N 0.000 description 1
- ZTXLEHGBELXWCK-SNAWJCMRSA-N (e)-2-bromohex-3-ene Chemical compound CC\C=C\C(C)Br ZTXLEHGBELXWCK-SNAWJCMRSA-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
- DDZTTWQJEJYUKA-UHFFFAOYSA-N 1,4-dibromodec-2-ene Chemical compound CCCCCCC(Br)C=CCBr DDZTTWQJEJYUKA-UHFFFAOYSA-N 0.000 description 1
- TUBRGNVWYALUBI-UHFFFAOYSA-N 1,4-dibromododec-2-ene Chemical compound CCCCCCCCC(Br)C=CCBr TUBRGNVWYALUBI-UHFFFAOYSA-N 0.000 description 1
- IROITDWRHMPXOO-UHFFFAOYSA-N 1,4-dibromohept-2-ene Chemical compound BrCC=CC(CCC)Br IROITDWRHMPXOO-UHFFFAOYSA-N 0.000 description 1
- IVNXCZYKOHEIGF-UHFFFAOYSA-N 1,4-dibromohex-2-ene Chemical compound CCC(Br)C=CCBr IVNXCZYKOHEIGF-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
- TTWRDHJRYYHEKD-UHFFFAOYSA-N 1,4-dibromopent-2-ene Chemical compound CC(Br)C=CCBr TTWRDHJRYYHEKD-UHFFFAOYSA-N 0.000 description 1
- JTNJYYDGJVTTAG-UHFFFAOYSA-N 1,4-dibromoundec-2-ene Chemical compound BrCC=CC(CCCCCCC)Br JTNJYYDGJVTTAG-UHFFFAOYSA-N 0.000 description 1
- DZKKXXFTSNFNAT-UHFFFAOYSA-N 1,4-dichlorododec-2-ene Chemical compound ClCC=CC(CCCCCCCC)Cl DZKKXXFTSNFNAT-UHFFFAOYSA-N 0.000 description 1
- JDFBGPUSKMHVBN-UHFFFAOYSA-N 1,4-dichlorohex-2-ene Chemical compound CCC(Cl)C=CCCl JDFBGPUSKMHVBN-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
- RIRZYCCNCIHMTP-UHFFFAOYSA-N 1,4-dichloroundec-2-ene Chemical compound ClCC=CC(CCCCCCC)Cl RIRZYCCNCIHMTP-UHFFFAOYSA-N 0.000 description 1
- MQLMJMLDYCCOHU-UHFFFAOYSA-N 1-bromododec-3-ene Chemical compound CCCCCCCCC=CCCBr MQLMJMLDYCCOHU-UHFFFAOYSA-N 0.000 description 1
- SGEUYXUPUOLFHQ-UHFFFAOYSA-N 1-bromohex-2-ene Chemical compound CCCC=CCBr SGEUYXUPUOLFHQ-UHFFFAOYSA-N 0.000 description 1
- WSXIDSNEEOYBFA-UHFFFAOYSA-N 1-bromopent-1-ene Chemical compound CCCC=CBr WSXIDSNEEOYBFA-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- KYRQIMSYGJMMRU-UHFFFAOYSA-N 1-chlorodec-3-ene Chemical compound CCCCCCC=CCCCl KYRQIMSYGJMMRU-UHFFFAOYSA-N 0.000 description 1
- UPJCRKZUCADENN-UHFFFAOYSA-N 1-chloropent-2-ene Chemical compound CCC=CCCl UPJCRKZUCADENN-UHFFFAOYSA-N 0.000 description 1
- YRCBNVMRRBIDNF-UHFFFAOYSA-N 2,3-dichlorobut-2-ene Chemical compound CC(Cl)=C(C)Cl YRCBNVMRRBIDNF-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
- ZBQCPZFPSVPIRS-UHFFFAOYSA-N 2,5-dichlorodec-3-ene Chemical compound ClC(C)C=CC(CCCCC)Cl ZBQCPZFPSVPIRS-UHFFFAOYSA-N 0.000 description 1
- HOPZJQSNNOKJCF-UHFFFAOYSA-N 2,5-dichlorododec-3-ene Chemical compound ClC(C)C=CC(CCCCCCC)Cl HOPZJQSNNOKJCF-UHFFFAOYSA-N 0.000 description 1
- WEUFFNGVWNVNED-UHFFFAOYSA-N 2,5-dichlorohept-3-ene Chemical compound ClC(C)C=CC(CC)Cl WEUFFNGVWNVNED-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
- GSDNIHWDVZMYBP-UHFFFAOYSA-N 2,5-dichlorooct-3-ene Chemical compound ClC(C)C=CC(CCC)Cl GSDNIHWDVZMYBP-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
- SGKRQBSZEHPDKH-UHFFFAOYSA-N 2-bromonon-3-ene Chemical compound BrC(C)C=CCCCCC SGKRQBSZEHPDKH-UHFFFAOYSA-N 0.000 description 1
- JWEUXNAOBUWKEF-UHFFFAOYSA-N 2-bromooct-3-ene Chemical compound BrC(C)C=CCCCC JWEUXNAOBUWKEF-UHFFFAOYSA-N 0.000 description 1
- UABCCEUZEDTYOZ-UHFFFAOYSA-N 2-bromoundec-3-ene Chemical compound BrC(C)C=CCCCCCCC UABCCEUZEDTYOZ-UHFFFAOYSA-N 0.000 description 1
- DNFOGEQIMJQCPG-UHFFFAOYSA-N 2-chlorodec-3-ene Chemical compound CCCCCCC=CC(C)Cl DNFOGEQIMJQCPG-UHFFFAOYSA-N 0.000 description 1
- XSCYNSZXBSINQM-UHFFFAOYSA-N 2-chlorododec-3-ene Chemical compound ClC(C)C=CCCCCCCCC XSCYNSZXBSINQM-UHFFFAOYSA-N 0.000 description 1
- AZRSIPLLMJADSK-UHFFFAOYSA-N 2-chlorohept-3-ene Chemical compound ClC(C)C=CCCC AZRSIPLLMJADSK-UHFFFAOYSA-N 0.000 description 1
- YZOPWNASQGPFJR-UHFFFAOYSA-N 2-chlorohex-2-ene Chemical compound CCCC=C(C)Cl YZOPWNASQGPFJR-UHFFFAOYSA-N 0.000 description 1
- AYRDQPCXJLQOQB-UHFFFAOYSA-N 2-chloroundec-3-ene Chemical compound ClC(C)C=CCCCCCCC AYRDQPCXJLQOQB-UHFFFAOYSA-N 0.000 description 1
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- JIDWPAITGBATKS-UHFFFAOYSA-N 3,4-dibromohex-1-ene Chemical compound CCC(Br)C(Br)C=C JIDWPAITGBATKS-UHFFFAOYSA-N 0.000 description 1
- ZTXFMTFPERLGES-UHFFFAOYSA-N 3,4-dibromopent-1-ene Chemical compound CC(Br)C(Br)C=C ZTXFMTFPERLGES-UHFFFAOYSA-N 0.000 description 1
- NGGBWBHYRHZBSH-UHFFFAOYSA-N 3,4-dichlorohept-1-ene Chemical compound CCCC(Cl)C(Cl)C=C NGGBWBHYRHZBSH-UHFFFAOYSA-N 0.000 description 1
- JQGARBLJULSUFA-UHFFFAOYSA-N 3,4-dichlorohex-1-ene Chemical compound CCC(Cl)C(Cl)C=C JQGARBLJULSUFA-UHFFFAOYSA-N 0.000 description 1
- ZZLDYZLPDLYQAC-UHFFFAOYSA-N 3,6-dibromocyclohexene Chemical compound BrC1CCC(Br)C=C1 ZZLDYZLPDLYQAC-UHFFFAOYSA-N 0.000 description 1
- KXMFSMNVGHBTBV-UHFFFAOYSA-N 3,6-dibromodec-4-ene Chemical compound BrC(CC)C=CC(CCCC)Br KXMFSMNVGHBTBV-UHFFFAOYSA-N 0.000 description 1
- NDDHILKZBFZYQR-UHFFFAOYSA-N 3,6-dibromonon-4-ene Chemical compound BrC(CC)C=CC(CCC)Br NDDHILKZBFZYQR-UHFFFAOYSA-N 0.000 description 1
- IHWVCKNEBWHOFC-UHFFFAOYSA-N 3,6-dibromooct-4-ene Chemical compound BrC(CC)C=CC(CC)Br IHWVCKNEBWHOFC-UHFFFAOYSA-N 0.000 description 1
- KNAGFNYSMXRYMW-UHFFFAOYSA-N 3,6-dichlorocyclohexene Chemical compound ClC1CCC(Cl)C=C1 KNAGFNYSMXRYMW-UHFFFAOYSA-N 0.000 description 1
- ACJADAAEJYGBAQ-UHFFFAOYSA-N 3,6-dichlorodec-4-ene Chemical compound ClC(CC)C=CC(CCCC)Cl ACJADAAEJYGBAQ-UHFFFAOYSA-N 0.000 description 1
- YTCDBXPPNABYAZ-UHFFFAOYSA-N 3,7-dibromocycloheptene Chemical compound BrC1CCCC(Br)C=C1 YTCDBXPPNABYAZ-UHFFFAOYSA-N 0.000 description 1
- DVVNBOLACJIERT-UHFFFAOYSA-N 3,7-dichlorocycloheptene Chemical compound ClC1CCCC(Cl)C=C1 DVVNBOLACJIERT-UHFFFAOYSA-N 0.000 description 1
- CFLJKGVEPOSUFX-UHFFFAOYSA-N 3,8-dibromocyclooctene Chemical compound BrC1CCCCC(Br)C=C1 CFLJKGVEPOSUFX-UHFFFAOYSA-N 0.000 description 1
- LUWLLVYQLSHGGK-UHFFFAOYSA-N 3,8-dichlorocyclooctene Chemical compound ClC1CCCCC(Cl)C=C1 LUWLLVYQLSHGGK-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- USEGQJLHQSTGHW-UHFFFAOYSA-N 3-bromo-2-methylprop-1-ene Chemical compound CC(=C)CBr USEGQJLHQSTGHW-UHFFFAOYSA-N 0.000 description 1
- XOTGLEGIDHZTIM-UHFFFAOYSA-N 3-bromobut-1-ene Chemical compound CC(Br)C=C XOTGLEGIDHZTIM-UHFFFAOYSA-N 0.000 description 1
- ZKGXAEJNBLJUQF-UHFFFAOYSA-N 3-bromocycloheptene Chemical compound BrC1CCCCC=C1 ZKGXAEJNBLJUQF-UHFFFAOYSA-N 0.000 description 1
- XOAUXFIKYVGQHT-UHFFFAOYSA-N 3-bromocyclooctene Chemical compound BrC1CCCCCC=C1 XOAUXFIKYVGQHT-UHFFFAOYSA-N 0.000 description 1
- GQWYECAAVJTKGA-UHFFFAOYSA-N 3-bromocyclopentene Chemical compound BrC1CCC=C1 GQWYECAAVJTKGA-UHFFFAOYSA-N 0.000 description 1
- ZUSOFIHBLJHKGP-UHFFFAOYSA-N 3-bromodec-1-ene Chemical compound CCCCCCCC(Br)C=C ZUSOFIHBLJHKGP-UHFFFAOYSA-N 0.000 description 1
- XQJHHZZFKOELOK-UHFFFAOYSA-N 3-bromododec-1-ene Chemical compound CCCCCCCCCC(Br)C=C XQJHHZZFKOELOK-UHFFFAOYSA-N 0.000 description 1
- XKJHNOAFZFHACN-UHFFFAOYSA-N 3-bromohept-1-ene Chemical compound CCCCC(Br)C=C XKJHNOAFZFHACN-UHFFFAOYSA-N 0.000 description 1
- VDDMJYXQNNXTGJ-UHFFFAOYSA-N 3-bromonon-4-ene Chemical compound BrC(CC)C=CCCCC VDDMJYXQNNXTGJ-UHFFFAOYSA-N 0.000 description 1
- NOLDKTAGFOFTDX-UHFFFAOYSA-N 3-bromooct-1-ene Chemical compound CCCCCC(Br)C=C NOLDKTAGFOFTDX-UHFFFAOYSA-N 0.000 description 1
- NUISHJZOHUGWPN-UHFFFAOYSA-N 3-bromooct-4-ene Chemical compound BrC(CC)C=CCCC NUISHJZOHUGWPN-UHFFFAOYSA-N 0.000 description 1
- MAUHKVNIHVSMSP-UHFFFAOYSA-N 3-bromopent-1-ene Chemical compound CCC(Br)C=C MAUHKVNIHVSMSP-UHFFFAOYSA-N 0.000 description 1
- IRHKGPSAHUIAJJ-UHFFFAOYSA-N 3-bromoundec-1-ene Chemical compound BrC(C=C)CCCCCCCC IRHKGPSAHUIAJJ-UHFFFAOYSA-N 0.000 description 1
- YOFOIVOBZGXZMQ-UHFFFAOYSA-N 3-chlorocyclooctene Chemical compound ClC1CCCCCC=C1 YOFOIVOBZGXZMQ-UHFFFAOYSA-N 0.000 description 1
- TXGLKDMFMUJORC-UHFFFAOYSA-N 3-chlorodec-1-ene Chemical compound CCCCCCCC(Cl)C=C TXGLKDMFMUJORC-UHFFFAOYSA-N 0.000 description 1
- ACBFABDGNLRWRX-UHFFFAOYSA-N 3-chlorododec-1-ene Chemical compound CCCCCCCCCC(Cl)C=C ACBFABDGNLRWRX-UHFFFAOYSA-N 0.000 description 1
- LDPWDXLYZCXUCU-UHFFFAOYSA-N 3-chlorohept-1-ene Chemical compound CCCCC(Cl)C=C LDPWDXLYZCXUCU-UHFFFAOYSA-N 0.000 description 1
- BXPJRVPVIHMAAA-UHFFFAOYSA-N 3-chlorohex-1-ene Chemical compound CCCC(Cl)C=C BXPJRVPVIHMAAA-UHFFFAOYSA-N 0.000 description 1
- WQEMCADLIQDYOT-UHFFFAOYSA-N 3-chloronon-1-ene Chemical compound CCCCCCC(Cl)C=C WQEMCADLIQDYOT-UHFFFAOYSA-N 0.000 description 1
- NXSPTWAMDYTBOX-UHFFFAOYSA-N 3-chloronon-4-ene Chemical compound ClC(CC)C=CCCCC NXSPTWAMDYTBOX-UHFFFAOYSA-N 0.000 description 1
- MTROFQOXRRQZST-UHFFFAOYSA-N 3-chlorooct-1-ene Chemical compound CCCCCC(Cl)C=C MTROFQOXRRQZST-UHFFFAOYSA-N 0.000 description 1
- VKSIAHZNPNRVLE-UHFFFAOYSA-N 3-chlorooct-4-ene Chemical compound ClC(CC)C=CCCC VKSIAHZNPNRVLE-UHFFFAOYSA-N 0.000 description 1
- GEVKGFRTXNJNKK-UHFFFAOYSA-N 3-chloropent-1-ene Chemical compound CCC(Cl)C=C GEVKGFRTXNJNKK-UHFFFAOYSA-N 0.000 description 1
- PVWZVFSKEIXAML-UHFFFAOYSA-N 3-chloroundec-1-ene Chemical compound CCCCCCCCC(Cl)C=C PVWZVFSKEIXAML-UHFFFAOYSA-N 0.000 description 1
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 1
- WSVIAQNBRKPWKO-UHFFFAOYSA-N 4,5-dichloropent-2-ene Chemical compound CC=CC(Cl)CCl WSVIAQNBRKPWKO-UHFFFAOYSA-N 0.000 description 1
- DCKUONBZBWQYPQ-UHFFFAOYSA-N 4,7-dibromodec-5-ene Chemical compound CCCC(Br)C=CC(Br)CCC DCKUONBZBWQYPQ-UHFFFAOYSA-N 0.000 description 1
- GQTCQKSNJUOQSF-UHFFFAOYSA-N 4,7-dichlorodec-5-ene Chemical compound CCCC(Cl)C=CC(Cl)CCC GQTCQKSNJUOQSF-UHFFFAOYSA-N 0.000 description 1
- YRBLHULVHIZPNA-UHFFFAOYSA-N 4,7-dichloroundec-5-ene Chemical compound ClC(CCC)C=CC(CCCC)Cl YRBLHULVHIZPNA-UHFFFAOYSA-N 0.000 description 1
- FDTQKQUQJQKWCL-UHFFFAOYSA-N 4-bromodec-2-ene Chemical compound BrC(C=CC)CCCCCC FDTQKQUQJQKWCL-UHFFFAOYSA-N 0.000 description 1
- QGWHHCPOKGZTAJ-UHFFFAOYSA-N 4-bromodec-5-ene Chemical compound BrC(CCC)C=CCCCC QGWHHCPOKGZTAJ-UHFFFAOYSA-N 0.000 description 1
- VRMOXJOYDMZXJT-UHFFFAOYSA-N 4-bromododec-2-ene Chemical compound BrC(C=CC)CCCCCCCC VRMOXJOYDMZXJT-UHFFFAOYSA-N 0.000 description 1
- RBLOYLDZRWUPRL-UHFFFAOYSA-N 4-bromododec-5-ene Chemical compound BrC(CCC)C=CCCCCCC RBLOYLDZRWUPRL-UHFFFAOYSA-N 0.000 description 1
- BJCRYDXWPSCJGO-UHFFFAOYSA-N 4-bromoundec-2-ene Chemical compound BrC(C=CC)CCCCCCC BJCRYDXWPSCJGO-UHFFFAOYSA-N 0.000 description 1
- LEUAOONRBYJTAF-UHFFFAOYSA-N 4-bromoundec-5-ene Chemical compound BrC(CCC)C=CCCCCC LEUAOONRBYJTAF-UHFFFAOYSA-N 0.000 description 1
- XZBVVWVGGMIDEL-UHFFFAOYSA-N 4-chlorodec-2-ene Chemical compound CCCCCCC(Cl)C=CC XZBVVWVGGMIDEL-UHFFFAOYSA-N 0.000 description 1
- FXYNRIVEAIJOPD-UHFFFAOYSA-N 4-chlorodec-5-ene Chemical compound CCCCC=CC(Cl)CCC FXYNRIVEAIJOPD-UHFFFAOYSA-N 0.000 description 1
- ASBLWUQJQHMKPN-UHFFFAOYSA-N 4-chlorododec-5-ene Chemical compound ClC(CCC)C=CCCCCCC ASBLWUQJQHMKPN-UHFFFAOYSA-N 0.000 description 1
- SAYCWWMDUXXRGU-UHFFFAOYSA-N 4-chloroundec-5-ene Chemical compound ClC(CCC)C=CCCCCC SAYCWWMDUXXRGU-UHFFFAOYSA-N 0.000 description 1
- DBFGDQQUEATQIT-UHFFFAOYSA-N 5,8-dibromododec-6-ene Chemical compound BrC(CCCC)C=CC(CCCC)Br DBFGDQQUEATQIT-UHFFFAOYSA-N 0.000 description 1
- MVPSIWCDGQZWJS-UHFFFAOYSA-N 5-bromodec-3-ene Chemical compound BrC(C=CCC)CCCCC MVPSIWCDGQZWJS-UHFFFAOYSA-N 0.000 description 1
- ZLMKKDKHRKFFGE-UHFFFAOYSA-N 5-bromododec-3-ene Chemical compound BrC(C=CCC)CCCCCCC ZLMKKDKHRKFFGE-UHFFFAOYSA-N 0.000 description 1
- JEAQCUYZWSCYCZ-UHFFFAOYSA-N 5-bromododec-6-ene Chemical compound BrC(CCCC)C=CCCCCC JEAQCUYZWSCYCZ-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- UNIPWVNARIEKBC-UHFFFAOYSA-N 5-chlorodec-3-ene Chemical compound ClC(C=CCC)CCCCC UNIPWVNARIEKBC-UHFFFAOYSA-N 0.000 description 1
- SMADMTGIGNRXNC-UHFFFAOYSA-N 5-chlorododec-3-ene Chemical compound ClC(C=CCC)CCCCCCC SMADMTGIGNRXNC-UHFFFAOYSA-N 0.000 description 1
- NHNOVVKNDWDEHZ-UHFFFAOYSA-N 5-chlorododec-6-ene Chemical compound ClC(CCCC)C=CCCCCC NHNOVVKNDWDEHZ-UHFFFAOYSA-N 0.000 description 1
- KITRKSHGHDLSLE-UHFFFAOYSA-N 5-chloroundec-3-ene Chemical compound ClC(C=CCC)CCCCCC KITRKSHGHDLSLE-UHFFFAOYSA-N 0.000 description 1
- ARARARGBJHYEJM-UHFFFAOYSA-N 6-bromodec-4-ene Chemical compound BrC(C=CCCC)CCCC ARARARGBJHYEJM-UHFFFAOYSA-N 0.000 description 1
- JSWVYUCTXVMISS-UHFFFAOYSA-N 6-bromododec-4-ene Chemical compound BrC(C=CCCC)CCCCCC JSWVYUCTXVMISS-UHFFFAOYSA-N 0.000 description 1
- CTXVGRHAYDBMFL-UHFFFAOYSA-N 6-bromonon-4-ene Chemical compound BrC(C=CCCC)CCC CTXVGRHAYDBMFL-UHFFFAOYSA-N 0.000 description 1
- UULNUANBDZGDEC-UHFFFAOYSA-N 6-bromoundec-4-ene Chemical compound BrC(C=CCCC)CCCCC UULNUANBDZGDEC-UHFFFAOYSA-N 0.000 description 1
- VZXMNMWKAIYUEY-UHFFFAOYSA-N 6-chlorododec-4-ene Chemical compound ClC(C=CCCC)CCCCCC VZXMNMWKAIYUEY-UHFFFAOYSA-N 0.000 description 1
- IFUDYWQYVKOXTC-UHFFFAOYSA-N 6-chloroundec-4-ene Chemical compound CCCCCC(Cl)C=CCCC IFUDYWQYVKOXTC-UHFFFAOYSA-N 0.000 description 1
- DTNWUDZGFAYNRM-UHFFFAOYSA-N 7-bromododec-5-ene Chemical compound BrC(C=CCCCC)CCCCC DTNWUDZGFAYNRM-UHFFFAOYSA-N 0.000 description 1
- MOGKHPPQABOVRC-UHFFFAOYSA-N 7-bromoundec-5-ene Chemical compound BrC(CCCC)C=CCCCC MOGKHPPQABOVRC-UHFFFAOYSA-N 0.000 description 1
- HBXWJEPDDMUFEA-UHFFFAOYSA-N 7-chlorododec-5-ene Chemical compound ClC(C=CCCCC)CCCCC HBXWJEPDDMUFEA-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- GVKSADHYWCFNSZ-CMDGGOBGSA-N CCCCCCC\C=C\CCCl Chemical compound CCCCCCC\C=C\CCCl GVKSADHYWCFNSZ-CMDGGOBGSA-N 0.000 description 1
- SJCDFDNNDQOELC-AATRIKPKSA-N CCC\C=C\C(C)Br Chemical compound CCC\C=C\C(C)Br SJCDFDNNDQOELC-AATRIKPKSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BQYNOLBRYLJDDB-UHFFFAOYSA-N ClC(C)C=CCCCCC Chemical compound ClC(C)C=CCCCCC BQYNOLBRYLJDDB-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001387976 Pera Species 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 241000193803 Therea Species 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 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
- LBAYFEDWGHXMSM-UHFFFAOYSA-N butaneperoxoic acid Chemical compound CCCC(=O)OO LBAYFEDWGHXMSM-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000002844 continuous effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 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
- DZGHBGLILAEHOR-UHFFFAOYSA-N dodec-6-ene Chemical compound CCCCCC=CCCCCC DZGHBGLILAEHOR-UHFFFAOYSA-N 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
- 125000005843 halogen group Chemical group 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
- 239000013067 intermediate product Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 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
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 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
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2734086.9 | 1977-07-28 | ||
| DE19772734086 DE2734086A1 (de) | 1977-07-28 | 1977-07-28 | Verfahren zur herstellung von halogenalkylsubstituierten oxiranen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1120048A true CA1120048A (en) | 1982-03-16 |
Family
ID=6015053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000308194A Expired CA1120048A (en) | 1977-07-28 | 1978-07-26 | Process for the preparation of halogenoalkyl- substituted oxiranes |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0000555B1 (enExample) |
| JP (1) | JPS5427514A (enExample) |
| AT (1) | AT358058B (enExample) |
| CA (1) | CA1120048A (enExample) |
| DD (1) | DD138066A5 (enExample) |
| DE (2) | DE2734086A1 (enExample) |
Families Citing this family (1)
| 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 |
Family Cites Families (2)
| 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 |
| DE2519297B2 (de) * | 1975-04-30 | 1981-05-14 | Bayer Ag, 5090 Leverkusen | Verfahren zur kontinuierlichen Herstellung von Propylenoxid |
-
1977
- 1977-07-28 DE DE19772734086 patent/DE2734086A1/de not_active Withdrawn
-
1978
- 1978-07-20 EP EP19780100457 patent/EP0000555B1/de not_active Expired
- 1978-07-20 DE DE7878100457T patent/DE2861620D1/de not_active Expired
- 1978-07-26 DD DD20695678A patent/DD138066A5/xx unknown
- 1978-07-26 JP JP9056878A patent/JPS5427514A/ja active Granted
- 1978-07-26 CA CA000308194A patent/CA1120048A/en not_active Expired
- 1978-07-26 AT AT544678A patent/AT358058B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DD138066A5 (de) | 1979-10-10 |
| JPS5427514A (en) | 1979-03-01 |
| ATA544678A (de) | 1980-01-15 |
| EP0000555A1 (de) | 1979-02-07 |
| AT358058B (de) | 1980-08-25 |
| DE2734086A1 (de) | 1979-02-22 |
| JPS6236030B2 (enExample) | 1987-08-05 |
| EP0000555B1 (de) | 1982-02-10 |
| DE2861620D1 (en) | 1982-03-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP3294720B1 (en) | A process for the preparation of terpinolene epoxide | |
| EP1406885A1 (en) | Process for manufacturing an a-dihydroxy derivative and epoxy resins prepared therefrom | |
| US4570011A (en) | Preparation of cyclobutene substituted aromatic hydrocarbons | |
| IE42394B1 (en) | Production of peracids and of epoxides | |
| GB1585012A (en) | Process for the epoxidation of olefins | |
| Mahadevan et al. | Synthesis via Vinyl Sulfones. 57. Facile Synthesis of Allyl,. gamma.-Iodoallyl, and Cyclopropyl Triflones via Radical-Mediated Atom-Transfer Addition of Iodomethyl Triflone to Olefins and Acetylenes | |
| US2861084A (en) | Process for the production of | |
| CA1120047A (en) | Process for the preparation of halogenoalkyl- substituted oxiranes | |
| EP0425555A1 (en) | PREPARATION OF EPOXIDE NITRATES. | |
| JPH0365348B2 (enExample) | ||
| US3708506A (en) | Manufacture of epoxy compounds by reaction of olefins with hydroperoxides and borate esters in situ | |
| US3475498A (en) | Process for preparing ethyl benzene hydroperoxide | |
| JPS6236030B2 (enExample) | ||
| US3232957A (en) | Process for the preparation of olefin oxides | |
| US6673947B2 (en) | Process for preparing 3-fluoroalkoxymethyl-3-alkyloxetanes | |
| US3290336A (en) | Epoxide production | |
| EP0019804B1 (en) | Bromination of side chain of m-phenoxytoluene | |
| US4212809A (en) | Process for the preparation of 5-(oxiranylmethyl)-1,3-benzodioxole | |
| WO1995005370A1 (en) | Epoxidation process with a partially neutralised caro's acid solution | |
| US2987525A (en) | Synthesis of polycyclic heterocyclic compounds | |
| JP2952027B2 (ja) | シクロヘキセンオキシドの製造方法 | |
| US4238618A (en) | Process for the preparation of diacylated 4-imidazolin-2-ones | |
| JP2012131732A (ja) | ジクロロエポキシブタンの製造方法 | |
| JP2010100546A (ja) | オレフィン化合物のエポキシ化方法 | |
| GB2330358A (en) | Epoxidation of Alkenes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |