CA1120048A - Process for the preparation of halogenoalkyl- substituted oxiranes - Google Patents

Process for the preparation of halogenoalkyl- substituted oxiranes

Info

Publication number: CA1120048A
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

CA000308194A

Other languages

English (en)

French (fr)

Inventor

Gebhard Rauleder

Helmut Waldmann

Willi Hofen

Rolf Wirthwein

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 CA1120048A publication Critical patent/CA1120048A/en

Status Expired legal-status Critical Current

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
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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
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DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
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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
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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
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ACJADAAEJYGBAQ-UHFFFAOYSA-N 3,6-dichlorodec-4-ene Chemical compound ClC(CC)C=CC(CCCC)Cl ACJADAAEJYGBAQ-UHFFFAOYSA-N 0.000 description 1
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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
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HBXWJEPDDMUFEA-UHFFFAOYSA-N 7-chlorododec-5-ene Chemical compound ClC(C=CCCCC)CCCCC HBXWJEPDDMUFEA-UHFFFAOYSA-N 0.000 description 1
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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)

CA000308194A 1977-07-28 1978-07-26 Process for the preparation of halogenoalkyl- substituted oxiranes Expired CA1120048A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19772734086 DE2734086A1 (de)	1977-07-28	1977-07-28	Verfahren zur herstellung von halogenalkylsubstituierten oxiranen
DEP2734086.9		1977-07-28

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 (de)
JP (1)	JPS5427514A (de)
AT (1)	AT358058B (de)
CA (1)	CA1120048A (de)
DD (1)	DD138066A5 (de)
DE (2)	DE2734086A1 (de)

Families Citing this family (1)

* 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

Family Cites Families (2)

* 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
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 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
- 1978-07-26 DD DD20695678A patent/DD138066A5/de unknown

Also Published As

Publication number	Publication date
JPS6236030B2 (de)	1987-08-05
EP0000555A1 (de)	1979-02-07
AT358058B (de)	1980-08-25
JPS5427514A (en)	1979-03-01
EP0000555B1 (de)	1982-02-10
DE2861620D1 (en)	1982-03-18
DD138066A5 (de)	1979-10-10
ATA544678A (de)	1980-01-15
DE2734086A1 (de)	1979-02-22

Legal Events

Date	Code	Title	Description
1999-03-16	MKEX	Expiry

Publication	Publication Date	Title
EP3294720B1 (de)	2020-12-02	Verfahren zur herstellung von terpinolenepoxid
EP1406885A1 (de)	2004-04-14	Verfahren zur herstellung von dihydroxyderivaten und epoxidharz davon
US4570011A (en)	1986-02-11	Preparation of cyclobutene substituted aromatic hydrocarbons
GB1585012A (en)	1981-02-18	Process for the epoxidation of olefins
CA1120048A (en)	1982-03-16	Process for the preparation of halogenoalkyl- substituted oxiranes
Mahadevan et al.	1995	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
JPS6339578B2 (de)	1988-08-05
US2861084A (en)	1958-11-18	Process for the production of
CA1120047A (en)	1982-03-16	Process for the preparation of halogenoalkyl- substituted oxiranes
EP0425555A1 (de)	1991-05-08	Herstellung von epoxinitraten.
JPH0365348B2 (de)	1991-10-11
US3708506A (en)	1973-01-02	Manufacture of epoxy compounds by reaction of olefins with hydroperoxides and borate esters in situ
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