CN102015648B - 在碱性介质中稳定的过氧丙酸组合物 - Google Patents
在碱性介质中稳定的过氧丙酸组合物 Download PDFInfo
- Publication number
- CN102015648B CN102015648B CN200980115133.0A CN200980115133A CN102015648B CN 102015648 B CN102015648 B CN 102015648B CN 200980115133 A CN200980115133 A CN 200980115133A CN 102015648 B CN102015648 B CN 102015648B
- Authority
- CN
- China
- Prior art keywords
- acid
- composition
- perpropionic
- aqueous solution
- perpropionic acid
- 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 - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 46
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims description 26
- VPTUPAVOBUEXMZ-UHFFFAOYSA-N (1-hydroxy-2-phosphonoethyl)phosphonic acid Chemical compound OP(=O)(O)C(O)CP(O)(O)=O VPTUPAVOBUEXMZ-UHFFFAOYSA-N 0.000 claims description 20
- GJAWHXHKYYXBSV-UHFFFAOYSA-N pyridinedicarboxylic acid Natural products OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 claims description 15
- LVPMIMZXDYBCDF-UHFFFAOYSA-N isocinchomeronic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)N=C1 LVPMIMZXDYBCDF-UHFFFAOYSA-N 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 230000000087 stabilizing effect Effects 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 6
- 239000000872 buffer Substances 0.000 description 5
- 235000019260 propionic acid Nutrition 0.000 description 5
- 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 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- -1 alkoxy fatty alcohols Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 238000005202 decontamination Methods 0.000 description 3
- 230000003588 decontaminative effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000003352 sequestering agent Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 229940120146 EDTMP Drugs 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 235000019353 potassium silicate Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NQIBQILAMKZKFE-UHFFFAOYSA-N 2-(5-bromo-2-fluorophenyl)-3-fluoropyridine Chemical compound FC1=CC=C(Br)C=C1C1=NC=CC=C1F NQIBQILAMKZKFE-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- XEORTEPGCNJPRV-UHFFFAOYSA-N P(O)(O)=O.OC=C Chemical class P(O)(O)=O.OC=C XEORTEPGCNJPRV-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- 239000004111 Potassium silicate Substances 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- YSMAMMWBEBTNEH-UHFFFAOYSA-N [2-[2-[bis(phosphonomethyl)amino]ethoxy]ethyl-(phosphonomethyl)amino]methylphosphonic acid Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCOCCN(CP(O)(O)=O)CP(O)(O)=O YSMAMMWBEBTNEH-UHFFFAOYSA-N 0.000 description 1
- UBJQWPYKKRPJRP-UHFFFAOYSA-N [Na].CP(O)(O)O Chemical compound [Na].CP(O)(O)O UBJQWPYKKRPJRP-UHFFFAOYSA-N 0.000 description 1
- BDJWAIRNDDBNES-UHFFFAOYSA-N [Na].P(=O)(O)OP(=O)O.OC=C Chemical compound [Na].P(=O)(O)OP(=O)O.OC=C BDJWAIRNDDBNES-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- ITZXULOAYIAYNU-UHFFFAOYSA-N cerium(4+) Chemical compound [Ce+4] ITZXULOAYIAYNU-UHFFFAOYSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- NSFKBZXCXCJZDQ-UHFFFAOYSA-N cumene;sodium Chemical compound [Na].CC(C)C1=CC=CC=C1 NSFKBZXCXCJZDQ-UHFFFAOYSA-N 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- DUYCTCQXNHFCSJ-UHFFFAOYSA-N dtpmp Chemical compound OP(=O)(O)CN(CP(O)(O)=O)CCN(CP(O)(=O)O)CCN(CP(O)(O)=O)CP(O)(O)=O DUYCTCQXNHFCSJ-UHFFFAOYSA-N 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 229940100242 glycol stearate Drugs 0.000 description 1
- 230000003165 hydrotropic effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- HPEUEJRPDGMIMY-IFQPEPLCSA-N molybdopterin Chemical compound O([C@H]1N2)[C@H](COP(O)(O)=O)C(S)=C(S)[C@@H]1NC1=C2N=C(N)NC1=O HPEUEJRPDGMIMY-IFQPEPLCSA-N 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229920000059 polyethylene glycol stearate Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 229940093916 potassium phosphate Drugs 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 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
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- PODWXQQNRWNDGD-UHFFFAOYSA-L sodium thiosulfate pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[O-]S([S-])(=O)=O PODWXQQNRWNDGD-UHFFFAOYSA-L 0.000 description 1
- ODBPOHVSVJZQRX-UHFFFAOYSA-M sodium;[2-[2-[bis(phosphonomethyl)amino]ethyl-(phosphonomethyl)amino]ethyl-(phosphonomethyl)amino]methyl-hydroxyphosphinate Chemical compound [Na+].OP(=O)(O)CN(CP(O)(O)=O)CCN(CP(O)(=O)O)CCN(CP(O)(O)=O)CP(O)([O-])=O ODBPOHVSVJZQRX-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- WYXIGTJNYDDFFH-UHFFFAOYSA-Q triazanium;borate Chemical compound [NH4+].[NH4+].[NH4+].[O-]B([O-])[O-] WYXIGTJNYDDFFH-UHFFFAOYSA-Q 0.000 description 1
- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3839—Polyphosphonic acids
- C07F9/386—Polyphosphonic acids containing hydroxy substituents in the hydrocarbon radicals
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
- A62D3/30—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
- A62D3/36—Detoxification by using acid or alkaline reagents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/02—Chemical warfare substances, e.g. cholinesterase inhibitors
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/04—Pesticides, e.g. insecticides, herbicides, fungicides or nematocides
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/20—Organic substances
- A62D2101/26—Organic substances containing nitrogen or phosphorus
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/20—Organic substances
- A62D2101/28—Organic substances containing oxygen, sulfur, selenium or tellurium, i.e. chalcogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Toxicology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Business, Economics & Management (AREA)
- Emergency Management (AREA)
- Detergent Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Abstract
本发明涉及在碱性介质中是稳定的过氧丙酸的组合物，涉及使过氧丙酸稳定的方法，以及用于在碱性介质中使过氧丙酸稳定的化合物的特定组合的用途。
Description
本发明涉及在碱性介质中是稳定的过氧丙酸的组合物，涉及使过氧丙酸稳定的方法，以及用于在碱性介质中使过氧丙酸稳定的化合物的特定组合的用途。
众所周知，由过氧化氢和丙酸制备的过氧丙酸溶液遵从平衡定律，其方程式可以示意地用下列方式表示：
该体系的发展动力学是相对缓慢的；它们通过强酸(如，硫酸或者磷酸)进行加速，其在适当情况下用作为催化剂。这些强酸的存在可以使该体系更快速发展直至它的平衡状态。然而，众所周知，一旦它达到了它的平衡状态，该体系慢慢地失去它包含的活性氧，这种损失表现为过酸和过氧化氢的含量的缓慢减少。为了克服这种现象，使用稳定剂如吡啶二羧酸。
过氧丙酸的一些用途需要使用过氧丙酸在碱性介质中的溶液。这涉及，例如基于过氧丙酸的组合物用于去污有机磷或者有机硫毒性产品的用途，例如用于军事领域的毒性剂或者用于农业领域的植物保护产品。
国际申请WO 01/30452描述了包含过氧丙酸、用作稳定剂的吡啶二羧酸的碱性组合物。这种组合物用于去污毒性产品的用途描述在该文献中。然而，这种组合物没有显示令人满意的稳定性。因此存在对新型的在碱性介质中更稳定的过氧丙酸组合物的需求。
本发明人因此开发了新型的基于过氧丙酸的组合物。根据本发明，该组合物包括过氧丙酸、吡啶二羧酸和羟基亚乙基二膦酸(HEDP)。
令人惊讶地，已经观察到如上面所定义的组合物是很稳定的，特别地比包含过氧丙酸、不同于HEDP的有机螯合剂的组合物更加稳定，所述不同于HEDP的有机螯合剂如通常用作H2O2稳定剂的DETMP钠(二亚乙基三胺五亚甲基膦酸的盐)或者EDTMP钠(乙二胺四亚甲基膦酸的盐)。这是因为与HEDP(实施例2)不同，这些有机螯合剂没有提供在该去污组合物的稳定方面的优点。
有利地，使用的过氧丙酸呈水溶液形式，特别地其如在催化剂(如硫酸或者硼酸)存在下，通过过氧化氢的水溶液与丙酸的反应获得的那些。这种制备方法例如描述在法国专利申请FR2462425中。与在法国专利申请No.FR2464947和FR2519634中描述的过氧丙酸的无水溶液不同，所述水溶液由简单方法得到，其不实施与有毒的或者易燃的有机溶剂(如1，2-二氯乙烷或者环己烷)共沸蒸馏的步骤。
由此，使用的过氧丙酸呈水溶液形式，其包含：作为产物的过氧丙酸，作为没有反应的反应剂的丙酸，作为没有反应的反应剂的过氧化氢水溶液，和作为催化剂的硫酸或者硼酸。
作为本发明主题的组合物因此可以包含：
-过氧丙酸
-吡啶二羧酸
-羟基亚乙基二膦酸
-丙酸
-过氧化氢水溶液，和
-硫酸和/或硼酸。
上面定义的组合物是在水中仅形成单相的溶液，这可以在水溶液中易于使用本发明主题的组合物。
举例来说，为本发明主题的组合物的羟基亚乙基二膦酸可以由Solutia公司以商标名Dequest销售的产品组成。
在一优选实施方案中，本发明主题的组合物包含(以相对于该组合物的总重量的重量表示)：
-30％-40％过氧丙酸，
-0.05％-2％吡啶二羧酸，和
-0.5％-5％羟基亚乙基二膦酸。
当本发明主题的组合物被稀释在碱性水溶液中时，获得的溶液是稳定的，如在实施例3中举例说明的那样。
在本发明的一种特殊的实施方案中，上面定义的组合物呈碱性水溶液形式。因此，本发明的主题还是包含如上面所定义的组合物的碱性水溶液。
对本发明来说，术语“碱性含水溶液”用来表示任何其pH高于7的包含水的溶液。
有利地，根据本发明的碱性水溶液具有8-12，甚至更优选地8.5-9.5的pH。必要时，pH可以使用碱化试剂进行调节。因此，在本发明的一个实施方案中，碱性水溶液包含碱化剂。这种碱化剂可以选自氢氧化钠，氢氧化钾，氢氧化铵，碳酸钠或碳酸氢钠，碳酸钾或碳酸氢钾，磷酸钠，磷酸钾，磷酸铵，硅酸钠，硅酸钾，硅酸铵，硼酸钠，硼酸钾，硼酸铵，和它们的混合物。
当本发明主题的组合物被稀释在碱性水溶液中时，吡啶二羧酸、过氧丙酸和HEDP可以呈它们相应的盐形式。
该组合物的稳定性通过在酸性介质中在环境温度下储存12个月之后过氧丙酸浓度没有明显的损失，即过氧丙酸浓度不低于起始浓度的90％，进行定义。根据本发明的组合物还显示出在碱性介质中在1小时之后过氧丙酸浓度的损失低于对不根据本发明的组合物(实施例3)所测量的过氧丙酸浓度的损失。一般地，该配制剂的去污效力不低于初始活性的80％。
根据本发明的组合物优选地以相对于该溶液的总重量0.5重量％-40重量％，优选地3重量％-10重量％的过氧丙酸的浓度的水溶液进行使用。它们还能以在与水不混溶的有机溶剂中分散后的乳状液或者微乳状液形式进行使用，该有机溶剂如，例如任选氯化的脂族或者芳香族烃，例如甲苯、二甲苯、二氯甲烷和四氯乙烯。
根据本发明的水溶液还可以包含，除了本发明主题的组合物外，选自碱性缓冲液、表面活性剂的化合物和它们的混合物。
这种水溶液特别地适合为用于破坏有机磷或者有机硫化合物的去污剂。
对本发明来说，术语“碱性缓冲液”用来表示单种类型的碱性缓冲液和碱性缓冲液的混合物这两者。根据本发明的组合物包含碱性缓冲液，如碱性碳酸盐或者碱性硅酸盐，特别地碳酸钾或者碳酸钠。
对本发明来说，术语“表面活性剂”用来表示阴离子的、阳离子的、非离子的或者两性表面活性剂，其以相对于该组合物的总重量的0重量％-25重量％，优选地5重量％-20重量％的比例进行使用。
作为阳离子表面活性剂，可以提到季铵类型的那些，例如：
-十六烷基三甲基溴化铵
-十六烷基三甲基氯化铵
-十六烷基二甲基2-羟基乙基溴化铵，
-十六烷基甲基双(2-羟基乙基)溴化铵，
-苄基三甲基溴化铵，和
-十六烷基二氮杂-1，4-双环[2.2.2]辛基溴化铵。
这些表面活性剂是已知的，并且它们中的大多数可商业获得。它们可以通过由C.A.Bunton等，J.Am.Chem.Soc.，95，2912(1973)和由L.Horner等，Phosphorus and Sulfur，11，339(1981)描述的方法进行制备。
作为任选地可以使用的非离子表面活性剂，可以提及，例如：
-下式的烷氧基化脂肪醇：R-[(CH2)2O]m-[CH2CH(CH3)O]n-H
其中R是包含8-22个碳原子，优选地12-14个碳原子的烷基或者链烯基；n和m独立地表示0-50的整数，其总和n+m＞1；
-下式的烷基多聚葡糖苷：R”’-[葡萄糖]n-，其中R”’是C8-C16烷基和n是1-3的整数；
-还原糖的酯、多元醇的酯和它们的乙氧基化衍生物，如，例如单硬脂酸脱水山梨糖醇酯、单硬脂酸甘油酯或者硬脂酸乙二醇酯，或者包含20个环氧乙烷的乙氧基化的单硬脂酸脱水山梨糖醇酯；
-下式的乙氧基化的烷基酰胺：
其中R如上面所定义和r和s是0-15的整数，其总和r+s＞1；
-烷基吡咯烷酮，其烷基是C6-C20烷基；和它们的混合物。
优选地，该过氧丙酸以例如0.05-4.5mol/l浓度的所述水溶液形式存在。
为本发明主题的溶液还可以包含至少一种选自水溶助长剂(如脲或者枯烯磺酸钠)、增粘剂(如黄原胶)、改性玉米淀粉、羟乙基纤维素或消泡剂的组分。
本发明的主题还是用于稳定包含过氧丙酸的碱性水溶液的方法，特征在于它包含将羟基亚乙基二膦酸或者其盐的一种溶解在所述过氧丙酸溶液中的步骤。
在上面定义的方法中，碱性水溶液还可以包含吡啶二羧酸。
在上面描述的方法中，使用的过氧丙酸可以在催化剂(如硫酸或者硼酸)存在下，通过过氧化氢的水溶液与过氧丙酸的反应而获得。
本发明还涉及羟基亚乙基二膦酸和/或其盐的一种用于稳定包含过氧丙酸和任选地吡啶二羧酸的碱性水溶液的用途。
举例来说，羟基亚乙基二膦酸的盐可以是钠盐或者钾盐。当使用羟基亚乙基二膦酸钠时，它可以由Solutia公司以商标名Dequest
销售的产品组成。
以下实施例举例说明本发明而不限制本发明的范围。在这些实施例中，百分比是按重量计的，除非另有说明。
实施例1
将1000g丙酸、15g硫酸、7.5g吡啶二羧酸和25g 60％的羟基亚乙基二膦酸(Dequest 2010，Solutia)进料到3升反应器中。在环境温度下和在搅拌下，在10分钟内加入500g 70％过氧化氢水溶液。搅拌12小时。
通过滴定碘法(与KI反应和用硫代硫酸钠滴定)定量该活性氧的量。过氧化氢水溶液使用铈(IV)硫酸盐进行定量。过氧丙酸浓度通过总活性氧和过氧化氢水溶液之间的差值进行推导。使用硫代硫酸盐定量活性氧的方法在以下手册中被提及：D.Swern Volume 1的Organic Peroxides(Wiley SBN 471839604)，第1章。
获得的组合物是：
| Cl | 重量％ |
| 过氧丙酸 | 38.2 |
| 过氧化氢水溶液 | 8.3 |
| 丙酸 | 33.8 |
| 水 | 17.2 |
| 硫酸 | 1.0 |
| 吡啶二羧酸 | 0.5 |
| 羟基亚乙基二膦酸 | 1.0 |
实施例2(不根据本发明)
3个不根据本发明的组合物根据实施例1进行制备：
实施例3
通过加入20％的氢氧化钾和碳酸钾水溶液(K2CO3/KOH质量比率＝2/1)使在实施例1和2中制备的组合物变成碱性pH。
过氧丙酸浓度通过在实施例1中描述的方法进行测量。
| 组合物 | pH | 在5分钟之后的过氧丙酸浓度，重量％ |
| C1 | 8.6 | 2.5 |
| C2 | 9.1 | 2.1 |
| C3 | 8.6 | 1.1 |
| C4 | 8.0 | 0.7 |
这些实施例说明了使用吡啶二羧酸和羟基亚乙基膦酸的组合与使用单独的吡啶二羧酸或者与其它膦酸类结合相比较的优点。
Claims (6)
1.包含组合物的水溶液，其中所述组合物包含：
(i)过氧丙酸
(ii)吡啶二羧酸，和
(iii)羟基亚乙基二膦酸
所述水溶液包含碱化剂，且具有高于7并低于或等于9.5的pH。
2.根据权利要求1的水溶液，特征在于组合物包含，以相对于该组合物的总重量的重量表示：
-30％-40％过氧丙酸，
-0.05％-2％吡啶二羧酸，
-0.5％-5％羟基亚乙基二膦酸。
3.根据权利要求1或2的水溶液，特征在于过氧丙酸以0.05-4.5mol/1浓度存在。
4.根据权利要求1或2的水溶液，其具有8.5-9.5的pH。
5.用于稳定包含过氧丙酸、吡啶二羧酸和碱化剂的并具有高于7且低于或等于9.5的pH的碱性水溶液的方法，特征在于它包含将羟基亚乙基二膦酸溶解在所述过氧丙酸溶液中的步骤。
6.羟基亚乙基二膦酸用于稳定包含过氧丙酸、吡啶二羧酸和碱化剂的并具有高于7且低于或等于9.5的pH的碱性水溶液的用途。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0852895 | 2008-04-29 | ||
| FR0852895A FR2930449B1 (fr) | 2008-04-29 | 2008-04-29 | Composition d'acide perpropionique stable en milieu basique |
| PCT/FR2009/050778 WO2009141547A2 (fr) | 2008-04-29 | 2009-04-28 | Composition d'acide perpropionique stable en milieu basique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102015648A CN102015648A (zh) | 2011-04-13 |
| CN102015648B true CN102015648B (zh) | 2014-01-29 |
Family
ID=40076797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980115133.0A Expired - Fee Related CN102015648B (zh) | 2008-04-29 | 2009-04-28 | 在碱性介质中稳定的过氧丙酸组合物 |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP2271623B1 (zh) |
| JP (1) | JP5391267B2 (zh) |
| CN (1) | CN102015648B (zh) |
| FR (1) | FR2930449B1 (zh) |
| IL (1) | IL208608A (zh) |
| WO (1) | WO2009141547A2 (zh) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991007375A1 (en) * | 1989-11-10 | 1991-05-30 | Eka Nobel Ab | Peracetic acid composition |
| WO1991013058A1 (en) * | 1990-02-23 | 1991-09-05 | Interox Chemicals Limited | Solutions of peracids |
| EP0864562A2 (en) * | 1997-03-15 | 1998-09-16 | Solvay Interox Limited | Stabilised peracid solutions |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2462425A1 (fr) | 1979-08-01 | 1981-02-13 | Air Liquide | Procede de fabrication de solutions diluees stables de peracides carboxyliques aliphatiques |
| FR2464947A1 (fr) | 1979-09-07 | 1981-03-20 | Ugine Kuhlmann | Procede de fabrication d'acides percarboxyliques |
| FR2519634B1 (fr) | 1982-01-13 | 1986-09-12 | Ugine Kuhlmann | Perfectionnement aux procedes de synthese des acides percaboxyliques |
| JPS63119457A (ja) * | 1986-11-05 | 1988-05-24 | Mitsui Toatsu Chem Inc | 過プロピオン酸の安定化方法 |
| FI111459B (fi) * | 2001-04-04 | 2003-07-31 | Kemira Chemicals Oy | Menetelmä stabiilin peretikkahappotuotteen valmistamiseksi |
-
2008
- 2008-04-29 FR FR0852895A patent/FR2930449B1/fr active Active
-
2009
- 2009-04-28 WO PCT/FR2009/050778 patent/WO2009141547A2/fr active Application Filing
- 2009-04-28 JP JP2011506754A patent/JP5391267B2/ja not_active Expired - Fee Related
- 2009-04-28 CN CN200980115133.0A patent/CN102015648B/zh not_active Expired - Fee Related
- 2009-04-28 EP EP09750028.4A patent/EP2271623B1/fr not_active Not-in-force
-
2010
- 2010-10-11 IL IL208608A patent/IL208608A/en not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991007375A1 (en) * | 1989-11-10 | 1991-05-30 | Eka Nobel Ab | Peracetic acid composition |
| WO1991013058A1 (en) * | 1990-02-23 | 1991-09-05 | Interox Chemicals Limited | Solutions of peracids |
| EP0864562A2 (en) * | 1997-03-15 | 1998-09-16 | Solvay Interox Limited | Stabilised peracid solutions |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2271623B1 (fr) | 2013-07-24 |
| IL208608A0 (en) | 2010-12-30 |
| FR2930449B1 (fr) | 2010-04-23 |
| JP5391267B2 (ja) | 2014-01-15 |
| JP2011522785A (ja) | 2011-08-04 |
| FR2930449A1 (fr) | 2009-10-30 |
| WO2009141547A3 (fr) | 2010-02-25 |
| CN102015648A (zh) | 2011-04-13 |
| WO2009141547A2 (fr) | 2009-11-26 |
| IL208608A (en) | 2014-11-30 |
| EP2271623A2 (fr) | 2011-01-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102015035B (zh) | 用于破坏有机磷和/或有机硫污染物的组合物和方法 | |
| US8802613B2 (en) | Stabilized hydrogen peroxide solutions | |
| CA2042348C (en) | Herbicidal solutions based on n-phosphonomethylglycine | |
| JPH02295907A (ja) | Ｎ―ホスホノメチルグリシンをベースとする液状濃縮組成物 | |
| CA2591052A1 (en) | Herbicidal composition comprising an aminophosphate or aminophosphonate salt and a betaine | |
| MX2011000928A (es) | Soluciones acuosas diluidas de peracido y metodo de estabilizacion. | |
| BR9814759A (pt) | Sistemas de tensìdios para preparados aquosos lìquidos | |
| AU2008243170A1 (en) | Herbicidal composition comprising an aminophosphate or aminophosphonate salt and a viscosity reducing agent | |
| IT9020701A1 (it) | Composizioni erbicide a base di n-fosfonometilglicina e loro impiego | |
| Rougier et al. | Reactivity of the Insecticide Fenitrothion toward O and N Nucleophiles | |
| FR2737390A1 (fr) | Composition phytosanitaire hydrosoluble comprenant au moins des amidoamines polyacoxylees | |
| CN102015648B (zh) | 在碱性介质中稳定的过氧丙酸组合物 | |
| CN103827282A (zh) | 用于制备消毒剂的多部分试剂盒体系 | |
| JPH04349109A (ja) | アルカリ性過酸化水素水溶液及びその安定化方法 | |
| CA2340022A1 (fr) | Formulations phytosanitaires a forte teneur en matiere active | |
| US20140005090A1 (en) | Stabilization of surfactants against oxidative attack | |
| JP2009144106A (ja) | α−スルホ脂肪酸アルキルエステル塩水性液の分離抑制方法及びアニオン界面活性剤組成物 | |
| WO2014041010A1 (en) | Stabilization of paint stripper formulations | |
| ITVA20110010A1 (it) | Composizione acquosa diserbante concentrata | |
| AU2015200357A1 (en) | Combinations of derivatized saccharide surfactants and amine oxide surfactants as herbicide adjuvants. | |
| BRPI0705739B1 (pt) | composição herbicida aquosa concentrada e seu processo para preparação, bem como método para controlar ervas daninhas e método para controlar ervas daninhas em uma safra | |
| MXPA01005970A (en) | Pesticide formulations containing alkoxylated tristyrylphenol hemi-sulfate ester neutralized alkoxylated amine surfactants | |
| IES970559A2 (en) | A method for producing herbicidal compositions of glyphosate and glyphosate derivatives and herbicidal compositions thus produced |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20140129 Termination date: 20180428 |