DE2038318C3 - Verfahren zur Herstellung von Percarbonsänrelösungen oder Percarbonsäuren - Google Patents
Verfahren zur Herstellung von Percarbonsänrelösungen oder PercarbonsäurenInfo
- Publication number
- DE2038318C3 DE2038318C3 DE2038318A DE2038318A DE2038318C3 DE 2038318 C3 DE2038318 C3 DE 2038318C3 DE 2038318 A DE2038318 A DE 2038318A DE 2038318 A DE2038318 A DE 2038318A DE 2038318 C3 DE2038318 C3 DE 2038318C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- ester
- mono
- dimethylphosphinic
- percarboxylic
- 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
- 239000002253 acid Substances 0.000 title claims description 39
- 238000000034 method Methods 0.000 title claims description 30
- 150000007513 acids Chemical class 0.000 title claims description 19
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 53
- 150000001735 carboxylic acids Chemical class 0.000 claims description 20
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 15
- -1 alkylene radical Chemical class 0.000 description 108
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 40
- 150000002148 esters Chemical class 0.000 description 31
- 239000000243 solution Substances 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- GOJNABIZVJCYFL-UHFFFAOYSA-N dimethylphosphinic acid Chemical compound CP(C)(O)=O GOJNABIZVJCYFL-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000004821 distillation Methods 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 17
- 239000012071 phase Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical group 0.000 description 10
- 150000004965 peroxy acids Chemical class 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 8
- 235000011054 acetic acid Nutrition 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 229910019142 PO4 Inorganic materials 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 239000010452 phosphate Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000010533 azeotropic distillation Methods 0.000 description 6
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- 229940090181 propyl acetate Drugs 0.000 description 4
- 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 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 229940072049 amyl acetate Drugs 0.000 description 3
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- GOJNABIZVJCYFL-UHFFFAOYSA-M dimethylphosphinate Chemical compound CP(C)([O-])=O GOJNABIZVJCYFL-UHFFFAOYSA-M 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- NYYLZXREFNYPKB-UHFFFAOYSA-N 1-[ethoxy(methyl)phosphoryl]oxyethane Chemical compound CCOP(C)(=O)OCC NYYLZXREFNYPKB-UHFFFAOYSA-N 0.000 description 2
- SVWHXFUUCAUJSN-UHFFFAOYSA-N 1-methyl-1$l^{5}-phospholane 1-oxide Chemical compound CP1(=O)CCCC1 SVWHXFUUCAUJSN-UHFFFAOYSA-N 0.000 description 2
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 229910014569 C—OOH Inorganic materials 0.000 description 2
- RMULOCOTJVUURF-UHFFFAOYSA-N OC1CCC(CC1)P(O)(O)=O Chemical compound OC1CCC(CC1)P(O)(O)=O RMULOCOTJVUURF-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HRKAMJBPFPHCSD-UHFFFAOYSA-N Tri-isobutylphosphate Chemical compound CC(C)COP(=O)(OCC(C)C)OCC(C)C HRKAMJBPFPHCSD-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229940043232 butyl acetate Drugs 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 2
- ZJXZSIYSNXKHEA-UHFFFAOYSA-L ethyl phosphate(2-) Chemical compound CCOP([O-])([O-])=O ZJXZSIYSNXKHEA-UHFFFAOYSA-L 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 150000003008 phosphonic acid esters Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052707 ruthenium Inorganic materials 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
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 229940074411 xylene Drugs 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- SNFZGONQCTYGML-UHFFFAOYSA-N (1-hydroxycyclohexyl) dihydrogen phosphate Chemical compound P(=O)(O)(O)OC1(CCCCC1)O SNFZGONQCTYGML-UHFFFAOYSA-N 0.000 description 1
- AOJSHUFFESHCRA-UHFFFAOYSA-N (2-chlorophenyl)phosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1Cl AOJSHUFFESHCRA-UHFFFAOYSA-N 0.000 description 1
- VTLSGZWUFXMAOD-UHFFFAOYSA-N (2-hydroxyphenyl)phosphonic acid Chemical compound OC1=CC=CC=C1P(O)(O)=O VTLSGZWUFXMAOD-UHFFFAOYSA-N 0.000 description 1
- CTXHTPXAVIXGGI-UHFFFAOYSA-N (3-methoxy-2-methyl-3-oxopropyl)phosphonic acid Chemical compound COC(=O)C(C)CP(O)(O)=O CTXHTPXAVIXGGI-UHFFFAOYSA-N 0.000 description 1
- UYPOZCXBRKUQSO-UHFFFAOYSA-N (4-cyanophenyl) dimethyl phosphate Chemical compound COP(=O)(OC)OC1=CC=C(C#N)C=C1 UYPOZCXBRKUQSO-UHFFFAOYSA-N 0.000 description 1
- GAMAZXUFLYJCBP-UHFFFAOYSA-N (4-methoxycyclohexyl)phosphonic acid Chemical compound COC1CCC(CC1)P(O)(O)=O GAMAZXUFLYJCBP-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- NRMHUSQXOMWJGD-UHFFFAOYSA-N 1-[methyl(propoxy)phosphoryl]oxypropane Chemical compound CCCOP(C)(=O)OCCC NRMHUSQXOMWJGD-UHFFFAOYSA-N 0.000 description 1
- ZSSWXNPRLJLCDU-UHFFFAOYSA-N 1-diethylphosphorylethane Chemical compound CCP(=O)(CC)CC ZSSWXNPRLJLCDU-UHFFFAOYSA-N 0.000 description 1
- VPHALJFXAIUBQT-UHFFFAOYSA-N 1-dimethylphosphoryloxy-2-methoxybenzene Chemical compound COC1=C(C=CC=C1)OP(=O)(C)C VPHALJFXAIUBQT-UHFFFAOYSA-N 0.000 description 1
- UFWAYTYCPIBFRV-UHFFFAOYSA-N 1-dimethylphosphoryloxy-2-methylbenzene Chemical compound CC1=CC=CC=C1OP(C)(C)=O UFWAYTYCPIBFRV-UHFFFAOYSA-N 0.000 description 1
- XYECZHZTKGITCY-UHFFFAOYSA-N 1-dimethylphosphoryloxy-2-methylbutane Chemical compound CCC(C)COP(C)(C)=O XYECZHZTKGITCY-UHFFFAOYSA-N 0.000 description 1
- ISNAIBMDOIVBSI-UHFFFAOYSA-N 1-dimethylphosphoryloxy-2-methylpentane Chemical compound CCCC(C)COP(C)(C)=O ISNAIBMDOIVBSI-UHFFFAOYSA-N 0.000 description 1
- XAZJFCQCYNQNBH-UHFFFAOYSA-N 1-dimethylphosphoryloxy-2-methylpropane Chemical compound CC(C)COP(C)(C)=O XAZJFCQCYNQNBH-UHFFFAOYSA-N 0.000 description 1
- RGIYVVXQNIIDJZ-UHFFFAOYSA-N 1-dimethylphosphoryloxy-3-methoxybenzene Chemical compound COC=1C=C(C=CC1)OP(=O)(C)C RGIYVVXQNIIDJZ-UHFFFAOYSA-N 0.000 description 1
- JAQMXWKDTKQIQQ-UHFFFAOYSA-N 1-dimethylphosphoryloxy-3-methylbenzene Chemical compound CC1=CC=CC(OP(C)(C)=O)=C1 JAQMXWKDTKQIQQ-UHFFFAOYSA-N 0.000 description 1
- MEBYWAYZDSNFCU-UHFFFAOYSA-N 1-dimethylphosphoryloxy-3-methylcyclopentane Chemical compound CC1CCC(OP(C)(C)=O)C1 MEBYWAYZDSNFCU-UHFFFAOYSA-N 0.000 description 1
- GVFPRYAPMFINSY-UHFFFAOYSA-N 1-dimethylphosphoryloxyethane Chemical compound CCOP(C)(C)=O GVFPRYAPMFINSY-UHFFFAOYSA-N 0.000 description 1
- FADVPDGMBXTDDD-UHFFFAOYSA-N 1-dimethylphosphoryloxypropane Chemical compound CCCOP(C)(C)=O FADVPDGMBXTDDD-UHFFFAOYSA-N 0.000 description 1
- SNZSAFILJOCMFM-UHFFFAOYSA-N 1-dipropylphosphorylpropane Chemical compound CCCP(=O)(CCC)CCC SNZSAFILJOCMFM-UHFFFAOYSA-N 0.000 description 1
- CSSLZLQDGHKFLE-UHFFFAOYSA-N 1-hydroxy-1$l^{5}-phospholane 1-oxide Chemical compound OP1(=O)CCCC1 CSSLZLQDGHKFLE-UHFFFAOYSA-N 0.000 description 1
- JIGONOMRLCXLSP-UHFFFAOYSA-N 1-methoxy-1$l^{5}-phospholane 1-oxide Chemical compound COP1(=O)CCCC1 JIGONOMRLCXLSP-UHFFFAOYSA-N 0.000 description 1
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- GEZGQQFKEOIGJS-UHFFFAOYSA-N 2-di(propan-2-yl)phosphorylpropane Chemical compound CC(C)P(=O)(C(C)C)C(C)C GEZGQQFKEOIGJS-UHFFFAOYSA-N 0.000 description 1
- WDOOYFHFQQWOAO-UHFFFAOYSA-N 2-dimethylphosphoryloxy-2-methylpropane Chemical compound CC(C)(C)OP(C)(C)=O WDOOYFHFQQWOAO-UHFFFAOYSA-N 0.000 description 1
- HOLJWJGAMJVPKZ-UHFFFAOYSA-N 2-dimethylphosphoryloxybenzonitrile Chemical compound C(#N)C1=C(C=CC=C1)OP(=O)(C)C HOLJWJGAMJVPKZ-UHFFFAOYSA-N 0.000 description 1
- DVLVAUUGCDHCQL-UHFFFAOYSA-N 2-dimethylphosphoryloxybutane Chemical compound CCC(C)OP(C)(C)=O DVLVAUUGCDHCQL-UHFFFAOYSA-N 0.000 description 1
- ZLPICQDCFDTOPK-UHFFFAOYSA-N 2-dimethylphosphoryloxypropane Chemical compound CC(C)OP(C)(C)=O ZLPICQDCFDTOPK-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- RZPWYCMIHVHQNB-UHFFFAOYSA-N 2-methylbutylphosphonic acid Chemical compound CCC(C)CP(O)(O)=O RZPWYCMIHVHQNB-UHFFFAOYSA-N 0.000 description 1
- HAEFDDOAYBQRGK-UHFFFAOYSA-N 2-methylpropylphosphonic acid Chemical compound CC(C)CP(O)(O)=O HAEFDDOAYBQRGK-UHFFFAOYSA-N 0.000 description 1
- GPRQVQIDIJJIHD-UHFFFAOYSA-N 2-phenylethylphosphinic acid Chemical compound OP(=O)CCC1=CC=CC=C1 GPRQVQIDIJJIHD-UHFFFAOYSA-N 0.000 description 1
- BFDYSJCMAFSRDH-UHFFFAOYSA-N 2-phenylethylphosphonic acid Chemical compound OP(O)(=O)CCC1=CC=CC=C1 BFDYSJCMAFSRDH-UHFFFAOYSA-N 0.000 description 1
- BLALDUPQYCGKAG-UHFFFAOYSA-N 3,3-dimethylbutan-2-yloxy(methyl)phosphinic acid Chemical compound CC(C)(C)C(C)OP(C)(O)=O BLALDUPQYCGKAG-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
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- LDWBZTVVUJCQMN-UHFFFAOYSA-N 3-cyanobutylphosphonic acid Chemical compound N#CC(C)CCP(O)(O)=O LDWBZTVVUJCQMN-UHFFFAOYSA-N 0.000 description 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- OHMSWSFFCKZMGL-UHFFFAOYSA-N 3-methylbutylphosphonic acid Chemical compound CC(C)CCP(O)(O)=O OHMSWSFFCKZMGL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QTTDYUNOVOANDF-UHFFFAOYSA-N 4-cyanobutylphosphonic acid Chemical compound OP(O)(=O)CCCCC#N QTTDYUNOVOANDF-UHFFFAOYSA-N 0.000 description 1
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- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- CKVICYBZYGZLLP-UHFFFAOYSA-N pentylphosphonic acid Chemical compound CCCCCP(O)(O)=O CKVICYBZYGZLLP-UHFFFAOYSA-N 0.000 description 1
- 125000004351 phenylcyclohexyl group Chemical group C1(=CC=CC=C1)C1(CCCCC1)* 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003007 phosphonic acid derivatives Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ATLPLEZDTSBZQG-UHFFFAOYSA-N propan-2-ylphosphonic acid Chemical compound CC(C)P(O)(O)=O ATLPLEZDTSBZQG-UHFFFAOYSA-N 0.000 description 1
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OGDSVONAYZTTDA-UHFFFAOYSA-N tert-butylphosphonic acid Chemical compound CC(C)(C)P(O)(O)=O OGDSVONAYZTTDA-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YORMZGQXMARHOP-UHFFFAOYSA-N trichloromethyl dihydrogen phosphate Chemical compound OP(O)(=O)OC(Cl)(Cl)Cl YORMZGQXMARHOP-UHFFFAOYSA-N 0.000 description 1
- IELLVVGAXDLVSW-UHFFFAOYSA-N tricyclohexyl phosphate Chemical compound C1CCCCC1OP(OC1CCCCC1)(=O)OC1CCCCC1 IELLVVGAXDLVSW-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XJAAVVLEUZQVNJ-UHFFFAOYSA-N trifluoromethylphosphonic acid Chemical compound OP(O)(=O)C(F)(F)F XJAAVVLEUZQVNJ-UHFFFAOYSA-N 0.000 description 1
- QPRUJYKKQUQRDC-UHFFFAOYSA-N trihydroxymethyl dihydrogen phosphate Chemical compound OC(O)(O)OP(O)(O)=O QPRUJYKKQUQRDC-UHFFFAOYSA-N 0.000 description 1
- KJNVZTIMVKZSJR-UHFFFAOYSA-N trimethoxymethyl dihydrogen phosphate Chemical compound COC(OC)(OC)OP(O)(O)=O KJNVZTIMVKZSJR-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- OXFUXNFMHFCELM-UHFFFAOYSA-N tripropan-2-yl phosphate Chemical compound CC(C)OP(=O)(OC(C)C)OC(C)C OXFUXNFMHFCELM-UHFFFAOYSA-N 0.000 description 1
- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
- C07C407/003—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2038318A DE2038318C3 (de) | 1970-08-01 | 1970-08-01 | Verfahren zur Herstellung von Percarbonsänrelösungen oder Percarbonsäuren |
| RO67822A RO62195A (https=) | 1970-08-01 | 1971-07-27 | |
| CA119,379,A CA951324A (en) | 1970-08-01 | 1971-07-29 | Process for the preparation of percarboxylic acids |
| US00167529A US3845112A (en) | 1970-08-01 | 1971-07-29 | Process for the preparation of percarboxylic acids |
| GB3573571A GB1363916A (en) | 1970-08-01 | 1971-07-29 | Process for the preparation of percarboxylic acids |
| NL7110584A NL7110584A (https=) | 1970-08-01 | 1971-07-30 | |
| ZA715095A ZA715095B (en) | 1970-08-01 | 1971-07-30 | Process for the preparation of percarboxylic acid |
| FR717128175A FR2101175B1 (https=) | 1970-08-01 | 1971-07-30 | |
| AT06675/71A AT316497B (de) | 1970-08-01 | 1971-07-30 | Verfahren zur herstellung von percarbonsaeureloesungen oder percarbonsaeuren |
| BE770778A BE770778A (fr) | 1970-08-01 | 1971-07-30 | Procede de preparation d'acides percaboxyliques |
| SU1688972A SU496716A3 (ru) | 1970-08-01 | 1971-07-30 | Способ получени перкарбоновых кислот |
| JP5684971A JPS5314531B1 (https=) | 1970-08-01 | 1971-07-30 | |
| ES393839A ES393839A1 (es) | 1970-08-01 | 1971-07-31 | Procedimiento para la obtencion de acidos percarboxilicos. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2038318A DE2038318C3 (de) | 1970-08-01 | 1970-08-01 | Verfahren zur Herstellung von Percarbonsänrelösungen oder Percarbonsäuren |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2038318A1 DE2038318A1 (de) | 1972-02-10 |
| DE2038318B2 DE2038318B2 (de) | 1977-12-08 |
| DE2038318C3 true DE2038318C3 (de) | 1978-08-17 |
Family
ID=5778614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2038318A Expired DE2038318C3 (de) | 1970-08-01 | 1970-08-01 | Verfahren zur Herstellung von Percarbonsänrelösungen oder Percarbonsäuren |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3845112A (https=) |
| JP (1) | JPS5314531B1 (https=) |
| AT (1) | AT316497B (https=) |
| BE (1) | BE770778A (https=) |
| CA (1) | CA951324A (https=) |
| DE (1) | DE2038318C3 (https=) |
| ES (1) | ES393839A1 (https=) |
| FR (1) | FR2101175B1 (https=) |
| GB (1) | GB1363916A (https=) |
| NL (1) | NL7110584A (https=) |
| RO (1) | RO62195A (https=) |
| SU (1) | SU496716A3 (https=) |
| ZA (1) | ZA715095B (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4172086A (en) * | 1977-03-28 | 1979-10-23 | Fmc Corporation | Process for the manufacture of peroxycarboxylic acids |
| DE3320497A1 (de) * | 1983-06-07 | 1984-12-13 | Degussa Ag, 6000 Frankfurt | Verfahren zur herstellung von wasserunloeslichen peroxycarbonsaeuren |
| WO1995024388A1 (en) * | 1994-03-09 | 1995-09-14 | Kemira Chemicals B.V. | A method for the preparation of aqueous solutions containing performic acid as well as their use |
| US20090043123A1 (en) * | 2007-08-10 | 2009-02-12 | Fmc Corporation | Dilute Stabilized Peracetic Acid Production and Treatment Process |
-
1970
- 1970-08-01 DE DE2038318A patent/DE2038318C3/de not_active Expired
-
1971
- 1971-07-27 RO RO67822A patent/RO62195A/ro unknown
- 1971-07-29 US US00167529A patent/US3845112A/en not_active Expired - Lifetime
- 1971-07-29 CA CA119,379,A patent/CA951324A/en not_active Expired
- 1971-07-29 GB GB3573571A patent/GB1363916A/en not_active Expired
- 1971-07-30 NL NL7110584A patent/NL7110584A/xx not_active Application Discontinuation
- 1971-07-30 AT AT06675/71A patent/AT316497B/de not_active IP Right Cessation
- 1971-07-30 ZA ZA715095A patent/ZA715095B/xx unknown
- 1971-07-30 SU SU1688972A patent/SU496716A3/ru active
- 1971-07-30 BE BE770778A patent/BE770778A/xx unknown
- 1971-07-30 FR FR717128175A patent/FR2101175B1/fr not_active Expired
- 1971-07-30 JP JP5684971A patent/JPS5314531B1/ja active Pending
- 1971-07-31 ES ES393839A patent/ES393839A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| RO62195A (https=) | 1977-06-15 |
| ES393839A1 (es) | 1973-08-16 |
| NL7110584A (https=) | 1972-02-03 |
| SU496716A3 (ru) | 1975-12-25 |
| US3845112A (en) | 1974-10-29 |
| FR2101175A1 (https=) | 1972-03-31 |
| GB1363916A (en) | 1974-08-21 |
| AT316497B (de) | 1974-06-15 |
| BE770778A (fr) | 1972-01-31 |
| CA951324A (en) | 1974-07-16 |
| ZA715095B (en) | 1972-04-26 |
| DE2038318B2 (de) | 1977-12-08 |
| JPS5314531B1 (https=) | 1978-05-18 |
| DE2038318A1 (de) | 1972-02-10 |
| FR2101175B1 (https=) | 1973-06-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |