JPS6236030B2 - - Google Patents
Info
- Publication number
- JPS6236030B2 JPS6236030B2 JP53090568A JP9056878A JPS6236030B2 JP S6236030 B2 JPS6236030 B2 JP S6236030B2 JP 53090568 A JP53090568 A JP 53090568A JP 9056878 A JP9056878 A JP 9056878A JP S6236030 B2 JPS6236030 B2 JP S6236030B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- dichloro
- dibromo
- reaction
- 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
- 238000006243 chemical reaction Methods 0.000 claims description 55
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 38
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 claims description 32
- 150000001336 alkenes Chemical class 0.000 claims description 31
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical class OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 claims description 26
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 150000002924 oxiranes Chemical class 0.000 claims description 13
- 150000004965 peroxy acids Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000005673 monoalkenes Chemical class 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 9
- RMXLHIUHKIVPAB-OWOJBTEDSA-N (e)-1,4-dibromobut-2-ene Chemical compound BrC\C=C\CBr RMXLHIUHKIVPAB-OWOJBTEDSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- -1 methylene, chloromethylene Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 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 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 150000002431 hydrogen Chemical class 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
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 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 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 20
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
- 235000019260 propionic acid Nutrition 0.000 description 10
- 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 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 9
- 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
- VUSYFNXNYLAECV-UHFFFAOYSA-N 2,3-bis(chloromethyl)oxirane Chemical compound ClCC1OC1CCl VUSYFNXNYLAECV-UHFFFAOYSA-N 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 150000007522 mineralic acids Chemical class 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
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UKXROSORAUTSSH-UHFFFAOYSA-N 2-(1,2-dichloroethyl)oxirane Chemical compound ClCC(Cl)C1CO1 UKXROSORAUTSSH-UHFFFAOYSA-N 0.000 description 3
- ZBQFRDTZYRRHRU-UHFFFAOYSA-N 3,4-dibromobut-1-ene Chemical compound BrCC(Br)C=C ZBQFRDTZYRRHRU-UHFFFAOYSA-N 0.000 description 3
- VZGLVCFVUREVDP-UHFFFAOYSA-N 3-chlorobut-1-ene Chemical compound CC(Cl)C=C VZGLVCFVUREVDP-UHFFFAOYSA-N 0.000 description 3
- 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 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
- 238000004458 analytical method Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- YTKRILODNOEEPX-NSCUHMNNSA-N crotyl chloride Chemical compound C\C=C\CCl YTKRILODNOEEPX-NSCUHMNNSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 238000010992 reflux 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
- YTXXOKPWZPVIFH-SNAWJCMRSA-N (e)-1-chlorohex-2-ene Chemical compound CCC\C=C\CCl YTXXOKPWZPVIFH-SNAWJCMRSA-N 0.000 description 2
- 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
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-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
- TTWRDHJRYYHEKD-UHFFFAOYSA-N 1,4-dibromopent-2-ene Chemical compound CC(Br)C=CCBr TTWRDHJRYYHEKD-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
- PRDDYLMTZYBCDV-UHFFFAOYSA-N 1,4-dichloropent-2-ene Chemical compound CC(Cl)C=CCCl PRDDYLMTZYBCDV-UHFFFAOYSA-N 0.000 description 2
- SGEUYXUPUOLFHQ-UHFFFAOYSA-N 1-bromohex-2-ene Chemical compound CCCC=CCBr SGEUYXUPUOLFHQ-UHFFFAOYSA-N 0.000 description 2
- UPJCRKZUCADENN-UHFFFAOYSA-N 1-chloropent-2-ene Chemical compound CCC=CCCl UPJCRKZUCADENN-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
- GHRUELLVRVXPEW-UHFFFAOYSA-N 2,5-dichlorohex-3-ene Chemical compound CC(Cl)C=CC(C)Cl GHRUELLVRVXPEW-UHFFFAOYSA-N 0.000 description 2
- DMVMFPGTEDCOLO-UHFFFAOYSA-N 2-chlorohex-3-ene Chemical compound CCC=CC(C)Cl DMVMFPGTEDCOLO-UHFFFAOYSA-N 0.000 description 2
- JIDWPAITGBATKS-UHFFFAOYSA-N 3,4-dibromohex-1-ene Chemical compound CCC(Br)C(Br)C=C JIDWPAITGBATKS-UHFFFAOYSA-N 0.000 description 2
- ZTXFMTFPERLGES-UHFFFAOYSA-N 3,4-dibromopent-1-ene Chemical compound CC(Br)C(Br)C=C ZTXFMTFPERLGES-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
- KNAGFNYSMXRYMW-UHFFFAOYSA-N 3,6-dichlorocyclohexene Chemical compound ClC1CCC(Cl)C=C1 KNAGFNYSMXRYMW-UHFFFAOYSA-N 0.000 description 2
- 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 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
- 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
- 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
- MAUHKVNIHVSMSP-UHFFFAOYSA-N 3-bromopent-1-ene Chemical compound CCC(Br)C=C MAUHKVNIHVSMSP-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
- LNGQLHZIYFQUIR-UHFFFAOYSA-N 3-chlorocyclohexene Chemical compound ClC1CCCC=C1 LNGQLHZIYFQUIR-UHFFFAOYSA-N 0.000 description 2
- BXPJRVPVIHMAAA-UHFFFAOYSA-N 3-chlorohex-1-ene Chemical compound CCCC(Cl)C=C BXPJRVPVIHMAAA-UHFFFAOYSA-N 0.000 description 2
- GEVKGFRTXNJNKK-UHFFFAOYSA-N 3-chloropent-1-ene Chemical compound CCC(Cl)C=C GEVKGFRTXNJNKK-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
- 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
- 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
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-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
- 125000001931 aliphatic group Chemical group 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 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
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 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
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 2
- 238000004448 titration Methods 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
- 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
- OWNFMPKLXRVOQC-AATRIKPKSA-N (e)-1-bromohept-2-ene Chemical compound CCCC\C=C\CBr OWNFMPKLXRVOQC-AATRIKPKSA-N 0.000 description 1
- WFPIZALUFFTDFF-VOTSOKGWSA-N (e)-1-bromooct-2-ene Chemical compound CCCCC\C=C\CBr WFPIZALUFFTDFF-VOTSOKGWSA-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
- LOBQTAYIGUBNDX-AATRIKPKSA-N (e)-1-chlorohept-2-ene Chemical compound CCCC\C=C\CCl LOBQTAYIGUBNDX-AATRIKPKSA-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
- KIJVFSLXNWLMOW-VOTSOKGWSA-N (e)-1-chlorooct-2-ene Chemical compound CCCCC\C=C\CCl KIJVFSLXNWLMOW-VOTSOKGWSA-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
- IFTGEZOPUAJVMG-UHFFFAOYSA-N 1,1-dibromobut-1-ene Chemical compound CCC=C(Br)Br IFTGEZOPUAJVMG-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-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
- 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
- JTNJYYDGJVTTAG-UHFFFAOYSA-N 1,4-dibromoundec-2-ene Chemical compound BrCC=CC(CCCCCCC)Br JTNJYYDGJVTTAG-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
- DZKKXXFTSNFNAT-UHFFFAOYSA-N 1,4-dichlorododec-2-ene Chemical compound ClCC=CC(CCCCCCCC)Cl DZKKXXFTSNFNAT-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
- RIRZYCCNCIHMTP-UHFFFAOYSA-N 1,4-dichloroundec-2-ene Chemical compound ClCC=CC(CCCCCCC)Cl RIRZYCCNCIHMTP-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- RRLNGSBUIADGRX-UHFFFAOYSA-N 1-bromo-1-ethenylcyclohexane Chemical compound C=CC1(Br)CCCCC1 RRLNGSBUIADGRX-UHFFFAOYSA-N 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 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 (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19772734086 DE2734086A1 (de) | 1977-07-28 | 1977-07-28 | Verfahren zur herstellung von halogenalkylsubstituierten oxiranen |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5427514A JPS5427514A (en) | 1979-03-01 |
JPS6236030B2 true JPS6236030B2 (fr) | 1987-08-05 |
Family
ID=6015053
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP9056878A Granted JPS5427514A (en) | 1977-07-28 | 1978-07-26 | Process for preparing substituted oxilane |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0000555B1 (fr) |
JP (1) | JPS5427514A (fr) |
AT (1) | AT358058B (fr) |
CA (1) | CA1120048A (fr) |
DD (1) | DD138066A5 (fr) |
DE (2) | DE2734086A1 (fr) |
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/fr 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 CA CA000308194A patent/CA1120048A/fr not_active Expired
- 1978-07-26 JP JP9056878A patent/JPS5427514A/ja active Granted
- 1978-07-26 AT AT544678A patent/AT358058B/de not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
DE2734086A1 (de) | 1979-02-22 |
DE2861620D1 (en) | 1982-03-18 |
JPS5427514A (en) | 1979-03-01 |
AT358058B (de) | 1980-08-25 |
EP0000555B1 (fr) | 1982-02-10 |
ATA544678A (de) | 1980-01-15 |
EP0000555A1 (fr) | 1979-02-07 |
CA1120048A (fr) | 1982-03-16 |
DD138066A5 (de) | 1979-10-10 |
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