DE2507779C2 - Phosphorsäureesterhalogenide sowie Verfahren zu deren Herstellung - Google Patents
Phosphorsäureesterhalogenide sowie Verfahren zu deren HerstellungInfo
- Publication number
- DE2507779C2 DE2507779C2 DE2507779A DE2507779A DE2507779C2 DE 2507779 C2 DE2507779 C2 DE 2507779C2 DE 2507779 A DE2507779 A DE 2507779A DE 2507779 A DE2507779 A DE 2507779A DE 2507779 C2 DE2507779 C2 DE 2507779C2
- Authority
- DE
- Germany
- Prior art keywords
- radical
- halogen
- phosphoric acid
- carbon atoms
- group
- 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
- -1 Phosphoric acid ester halides Chemical class 0.000 title claims description 46
- 238000000034 method Methods 0.000 title claims description 27
- 239000000460 chlorine Substances 0.000 claims description 68
- 229910052801 chlorine Inorganic materials 0.000 claims description 34
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 33
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 25
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 25
- 229910052794 bromium Inorganic materials 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 150000002367 halogens Chemical group 0.000 claims description 24
- 239000011737 fluorine Substances 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 150000003254 radicals Chemical class 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
- 150000001336 alkenes Chemical class 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 8
- 230000002140 halogenating effect Effects 0.000 claims description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 8
- RLAROPIDCNCRNR-UHFFFAOYSA-N Cl.Cl.[C-]#N Chemical compound Cl.Cl.[C-]#N RLAROPIDCNCRNR-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002560 nitrile group Chemical group 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 150000002825 nitriles Chemical class 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 125000003172 aldehyde group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 7
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 238000003541 multi-stage reaction Methods 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003138 primary alcohols Chemical class 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 6
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- KNLUSLUJCULKTE-UHFFFAOYSA-N propyl dihydrogen phosphate;dihydrochloride Chemical compound Cl.Cl.CCCOP(O)(O)=O KNLUSLUJCULKTE-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- YZBOZNXACBQJHI-UHFFFAOYSA-N 1-dichlorophosphoryloxyethane Chemical compound CCOP(Cl)(Cl)=O YZBOZNXACBQJHI-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical group CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- ILXZMTJXXHNZJS-UHFFFAOYSA-N diethyl hydrogen phosphate;hydrochloride Chemical compound Cl.CCOP(O)(=O)OCC ILXZMTJXXHNZJS-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- YBBUMZUSUMRUKT-UHFFFAOYSA-N dimethyl hydrogen phosphate hydrochloride Chemical compound Cl.COP(O)(=O)OC YBBUMZUSUMRUKT-UHFFFAOYSA-N 0.000 description 2
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 description 1
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical class FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 1
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- BUAKPITZELZWNI-UHFFFAOYSA-N 1-chlorocyclohexene Chemical compound ClC1=CCCCC1 BUAKPITZELZWNI-UHFFFAOYSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- PNLQPWWBHXMFCA-UHFFFAOYSA-N 2-chloroprop-1-ene Chemical compound CC(Cl)=C PNLQPWWBHXMFCA-UHFFFAOYSA-N 0.000 description 1
- UKQJZQQPMIFNHE-UHFFFAOYSA-N 2-isocyanatoprop-1-ene Chemical compound CC(=C)N=C=O UKQJZQQPMIFNHE-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 1
- FAYFWMOSHFCQPG-UHFFFAOYSA-N 3-Methyl sulfolene Chemical compound CC1=CCS(=O)(=O)C1 FAYFWMOSHFCQPG-UHFFFAOYSA-N 0.000 description 1
- LNGQLHZIYFQUIR-UHFFFAOYSA-N 3-chlorocyclohexene Chemical compound ClC1CCCC=C1 LNGQLHZIYFQUIR-UHFFFAOYSA-N 0.000 description 1
- LXJDXBGQVSHLOJ-UHFFFAOYSA-N 3-isocyanoprop-1-ene Chemical compound C=CC[N+]#[C-] LXJDXBGQVSHLOJ-UHFFFAOYSA-N 0.000 description 1
- QVGKEZQXVLUDED-UHFFFAOYSA-N 4-chloro-1-isocyanatobut-1-ene Chemical compound ClCCC=CN=C=O QVGKEZQXVLUDED-UHFFFAOYSA-N 0.000 description 1
- AAMIYSNERSMTFE-UHFFFAOYSA-N 4-chloro-1-isocyanobut-1-ene Chemical compound ClCCC=C[N+]#[C-] AAMIYSNERSMTFE-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- MWLOLDRBELJKDK-UHFFFAOYSA-N Cl.COP(O)(=O)C1=CC=CC=C1 Chemical compound Cl.COP(O)(=O)C1=CC=CC=C1 MWLOLDRBELJKDK-UHFFFAOYSA-N 0.000 description 1
- KGWOWBJZJMKPKQ-UHFFFAOYSA-N Cl.Cl.CC(C)OP(O)(O)=O Chemical compound Cl.Cl.CC(C)OP(O)(O)=O KGWOWBJZJMKPKQ-UHFFFAOYSA-N 0.000 description 1
- MZAVCSVWLFEJLE-UHFFFAOYSA-N Cl.Cl.OP(O)(=O)OCCCl Chemical compound Cl.Cl.OP(O)(=O)OCCCl MZAVCSVWLFEJLE-UHFFFAOYSA-N 0.000 description 1
- NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical compound OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 description 1
- WIQHNEPWZZQSDK-UHFFFAOYSA-N F.F.CCOP(O)(O)=O Chemical compound F.F.CCOP(O)(O)=O WIQHNEPWZZQSDK-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 1
- XXHJFACWDVECEX-UHFFFAOYSA-N OP(OC(CCl)F)(OC(CCl)F)=O.Cl Chemical compound OP(OC(CCl)F)(OC(CCl)F)=O.Cl XXHJFACWDVECEX-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
- OZCRKDNRAAKDAN-UHFFFAOYSA-N but-1-ene-1,4-diol Chemical compound O[CH][CH]CCO OZCRKDNRAAKDAN-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 229930006739 camphene Natural products 0.000 description 1
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- HYPABJGVBDSCIT-UPHRSURJSA-N cyclododecene Chemical compound C1CCCCC\C=C/CCCC1 HYPABJGVBDSCIT-UPHRSURJSA-N 0.000 description 1
- YVWBQGFBSVLPIK-UHFFFAOYSA-N cyclohex-2-ene-1-carboxylic acid Chemical compound OC(=O)C1CCCC=C1 YVWBQGFBSVLPIK-UHFFFAOYSA-N 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- ONXOMWCDSXXELR-UHFFFAOYSA-N dibutyl hydrogen phosphate;hydrochloride Chemical compound Cl.CCCCOP(O)(=O)OCCCC ONXOMWCDSXXELR-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- SNVCRNWSNUUGEA-UHFFFAOYSA-N dichlorophosphoryloxymethane Chemical compound COP(Cl)(Cl)=O SNVCRNWSNUUGEA-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- NBMUEQRPPMFTJL-UHFFFAOYSA-N diethyl hydrogen phosphate hydrobromide Chemical compound Br.CCOP(O)(=O)OCC NBMUEQRPPMFTJL-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UJTPZISIAWDGFF-UHFFFAOYSA-N ethenylsulfonylbenzene Chemical compound C=CS(=O)(=O)C1=CC=CC=C1 UJTPZISIAWDGFF-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- CBWXWSRHBSRSMA-UHFFFAOYSA-N ethoxy(ethyl)phosphinic acid hydrochloride Chemical compound Cl.CCOP(O)(=O)CC CBWXWSRHBSRSMA-UHFFFAOYSA-N 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- BZAAYLBSHWLBGS-UHFFFAOYSA-N ethyl dihydrogen phosphate;hydrochloride Chemical compound Cl.CCOP(O)(O)=O BZAAYLBSHWLBGS-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 150000002238 fumaric acids Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical compound O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (26)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2507779A DE2507779C2 (de) | 1975-02-22 | 1975-02-22 | Phosphorsäureesterhalogenide sowie Verfahren zu deren Herstellung |
| HU76BA3358A HU175203B (hu) | 1975-02-22 | 1976-01-21 | Sposob poluchenija slozhnykh efirov galogenidov fosfornykh kislot |
| IE33976A IE42485B1 (en) | 1975-02-18 | 1976-02-18 | Solution welding of plastics process for the preparation of phosphoric or phosphonic acid ester halides |
| CH200576A CH623058A5 (en) | 1975-02-22 | 1976-02-18 | Process for the preparation of halophosphates or halophosphonates |
| NLAANVRAGE7601697,A NL187355C (nl) | 1975-02-22 | 1976-02-19 | Werkwijze ter bereiding van fosforzuuresterhalogeniden. |
| RO7684853A RO68979A (ro) | 1975-02-22 | 1976-02-19 | Procedeu pentru prepararea unor halogenuri ale esterilor acidului fosforic |
| GB6791/76A GB1513341A (en) | 1975-02-22 | 1976-02-20 | Process for the preparation of phosphoric or phosphonic acid ester halides |
| BE2054842A BE838737A (fr) | 1975-02-22 | 1976-02-20 | Procede de preparation d'halogenures-esters de l'acide phosphorique |
| AT122076A AT341543B (de) | 1975-02-22 | 1976-02-20 | Verfahren zur herstellung von phosphorsaureesterhalogeniden |
| LU74395A LU74395A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-02-22 | 1976-02-20 | |
| BR7601096A BR7601096A (pt) | 1975-02-22 | 1976-02-20 | Processo para a preparacao de halogenetos de acido fosforico |
| SU762325907A SU604499A3 (ru) | 1975-02-22 | 1976-02-20 | Способ получени галоидированных эфирохлорангидридов кислот фосфора |
| FR7604795A FR2301531A1 (fr) | 1975-02-22 | 1976-02-20 | Procede de preparation d'halogenures-esters de l'acide phosphorique |
| AU11307/76A AU496274B2 (en) | 1975-02-22 | 1976-02-20 | Process forthe preparation of phosphoric acid ester halides |
| IT48195/76A IT1053874B (it) | 1975-02-22 | 1976-02-20 | Procedimento per produrre alogenuri di esteri di acido fosforico e composti cosi ottenuti |
| CA246,203A CA1072574A (en) | 1975-02-22 | 1976-02-20 | Process for the preparation of phosphoric acid ester halides |
| IL7649077A IL49077A (en) | 1975-02-22 | 1976-02-20 | Preparation of phosphoric acid esterhalides and certain novel compounds thus prepared |
| DD191380A DD125577A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-02-22 | 1976-02-20 | |
| JP51017191A JPS5910677B2 (ja) | 1975-02-22 | 1976-02-20 | リン酸エステルハライドおよびその製造法 |
| ES445370A ES445370A1 (es) | 1975-02-22 | 1976-02-20 | Procedimiento para preparar halogenuros de esteres de acido fosforico. |
| ZA761006A ZA761006B (en) | 1975-02-22 | 1976-02-20 | Process for the preparation of phosphoric acid ester halides |
| DK70576A DK141936C (da) | 1975-02-22 | 1976-02-20 | Phosphorsyreesterhalogenider til anvendelse som mellemprodukter ved fremstillingen af phosphorsyreestere |
| CS7600001144A CS181696B2 (en) | 1975-02-22 | 1976-02-20 | Process for preparing esterhalogenides of phosphoric acid |
| PL1976187346A PL99859B1 (pl) | 1975-02-22 | 1976-02-20 | Sposob wytwarzania chlorowcowanych chlorkow estrow kwasu fosforowego |
| US05/857,153 US4182733A (en) | 1975-02-22 | 1977-12-05 | Process for preparing phosphoric acid esterhalides |
| US05/857,154 US4138452A (en) | 1975-02-22 | 1977-12-05 | Process for preparing phosphoric acid esterhalides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2507779A DE2507779C2 (de) | 1975-02-22 | 1975-02-22 | Phosphorsäureesterhalogenide sowie Verfahren zu deren Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2507779A1 DE2507779A1 (de) | 1976-09-02 |
| DE2507779C2 true DE2507779C2 (de) | 1982-07-01 |
Family
ID=5939608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2507779A Expired DE2507779C2 (de) | 1975-02-18 | 1975-02-22 | Phosphorsäureesterhalogenide sowie Verfahren zu deren Herstellung |
Country Status (22)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2630561A1 (de) * | 1976-07-07 | 1978-01-19 | Bayer Ag | 1-fluor-2-halogen-aethyl-thionophosphor (phosphon)-saeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL30533A (en) * | 1967-09-01 | 1972-01-27 | Bayer Ag | Thiol-or thionothiol-phosphoric or-phosphonic acid esters |
| DE2417143C2 (de) * | 1974-04-09 | 1982-04-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von (Thio) Phosphor(Phosphon)säureestern |
-
1975
- 1975-02-22 DE DE2507779A patent/DE2507779C2/de not_active Expired
-
1976
- 1976-01-21 HU HU76BA3358A patent/HU175203B/hu unknown
- 1976-02-18 CH CH200576A patent/CH623058A5/de not_active IP Right Cessation
- 1976-02-19 RO RO7684853A patent/RO68979A/ro unknown
- 1976-02-19 NL NLAANVRAGE7601697,A patent/NL187355C/xx not_active IP Right Cessation
- 1976-02-20 BE BE2054842A patent/BE838737A/xx not_active IP Right Cessation
- 1976-02-20 ES ES445370A patent/ES445370A1/es not_active Expired
- 1976-02-20 FR FR7604795A patent/FR2301531A1/fr active Granted
- 1976-02-20 LU LU74395A patent/LU74395A1/xx unknown
- 1976-02-20 BR BR7601096A patent/BR7601096A/pt unknown
- 1976-02-20 PL PL1976187346A patent/PL99859B1/pl unknown
- 1976-02-20 CA CA246,203A patent/CA1072574A/en not_active Expired
- 1976-02-20 JP JP51017191A patent/JPS5910677B2/ja not_active Expired
- 1976-02-20 AT AT122076A patent/AT341543B/de not_active IP Right Cessation
- 1976-02-20 IT IT48195/76A patent/IT1053874B/it active
- 1976-02-20 DK DK70576A patent/DK141936C/da not_active IP Right Cessation
- 1976-02-20 SU SU762325907A patent/SU604499A3/ru active
- 1976-02-20 CS CS7600001144A patent/CS181696B2/cs unknown
- 1976-02-20 IL IL7649077A patent/IL49077A/xx unknown
- 1976-02-20 GB GB6791/76A patent/GB1513341A/en not_active Expired
- 1976-02-20 ZA ZA761006A patent/ZA761006B/xx unknown
- 1976-02-20 DD DD191380A patent/DD125577A5/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |