US3839216A - Process for the production of organic solutions of percarboxylic acids - Google Patents
Process for the production of organic solutions of percarboxylic acids Download PDFInfo
- Publication number
- US3839216A US3839216A US00274965A US27496572A US3839216A US 3839216 A US3839216 A US 3839216A US 00274965 A US00274965 A US 00274965A US 27496572 A US27496572 A US 27496572A US 3839216 A US3839216 A US 3839216A
- Authority
- US
- United States
- Prior art keywords
- process according
- acetate
- percarboxylic acid
- ethyl
- carbon atoms
- 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 - Lifetime
Links
- 239000002253 acid Substances 0.000 title claims abstract description 26
- 150000007513 acids Chemical class 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims description 43
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000002904 solvent Substances 0.000 claims abstract description 23
- 239000000243 solution Substances 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 238000009835 boiling Methods 0.000 claims abstract description 11
- 238000010533 azeotropic distillation Methods 0.000 claims abstract description 6
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- -1 PHOSPHATE ESTER Chemical group 0.000 claims description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- 229910019142 PO4 Inorganic materials 0.000 claims description 13
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 12
- 239000010452 phosphate Substances 0.000 claims description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000003795 desorption Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical group CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 6
- NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 claims description 6
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 claims description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 4
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 claims description 4
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 claims description 4
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 claims description 3
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 claims description 3
- VUAXHMVRKOTJKP-UHFFFAOYSA-M 2,2-dimethylbutanoate Chemical compound CCC(C)(C)C([O-])=O VUAXHMVRKOTJKP-UHFFFAOYSA-M 0.000 claims description 3
- 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 claims description 3
- ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 2-(6-amino-1h-indol-3-yl)acetonitrile Chemical compound NC1=CC=C2C(CC#N)=CNC2=C1 ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 0.000 claims description 3
- ZKZHWAJZNZJAKV-UHFFFAOYSA-N 2-bromo-3-methylquinoline Chemical compound C1=CC=C2N=C(Br)C(C)=CC2=C1 ZKZHWAJZNZJAKV-UHFFFAOYSA-N 0.000 claims description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 3
- ICMAFTSLXCXHRK-UHFFFAOYSA-N Ethyl pentanoate Chemical compound CCCCC(=O)OCC ICMAFTSLXCXHRK-UHFFFAOYSA-N 0.000 claims description 3
- LSJMDWFAADPNAX-UHFFFAOYSA-N Isovaleriansaeure-propylester Natural products CCCOC(=O)CC(C)C LSJMDWFAADPNAX-UHFFFAOYSA-N 0.000 claims description 3
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 3
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims description 3
- FCDMDSDHBVPGGE-UHFFFAOYSA-N butyl 2,2-dimethylpropanoate Chemical compound CCCCOC(=O)C(C)(C)C FCDMDSDHBVPGGE-UHFFFAOYSA-N 0.000 claims description 3
- HHEIMYAXCOIQCJ-UHFFFAOYSA-N ethyl 2,2-dimethylpropanoate Chemical compound CCOC(=O)C(C)(C)C HHEIMYAXCOIQCJ-UHFFFAOYSA-N 0.000 claims description 3
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 claims description 3
- 229940017219 methyl propionate Drugs 0.000 claims description 3
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 claims description 3
- IOTAYCLTDJEUCF-UHFFFAOYSA-N pentyl 2,2-dimethylpropanoate Chemical compound CCCCCOC(=O)C(C)(C)C IOTAYCLTDJEUCF-UHFFFAOYSA-N 0.000 claims description 3
- TWSRVQVEYJNFKQ-UHFFFAOYSA-N pentyl propanoate Chemical compound CCCCCOC(=O)CC TWSRVQVEYJNFKQ-UHFFFAOYSA-N 0.000 claims description 3
- PMFKTHJAJBPRNM-UHFFFAOYSA-N propan-2-yl 2,2-dimethylpropanoate Chemical compound CC(C)OC(=O)C(C)(C)C PMFKTHJAJBPRNM-UHFFFAOYSA-N 0.000 claims description 3
- QMKUYPGVVVLYSR-UHFFFAOYSA-N propyl 2,2-dimethylpropanoate Chemical compound CCCOC(=O)C(C)(C)C QMKUYPGVVVLYSR-UHFFFAOYSA-N 0.000 claims description 3
- 229960002415 trichloroethylene Drugs 0.000 claims description 3
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical group COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 claims description 2
- WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-UHFFFAOYSA-N 0.000 claims description 2
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 claims description 2
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 229940072049 amyl acetate Drugs 0.000 claims description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 229940043232 butyl acetate Drugs 0.000 claims description 2
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 229940093499 ethyl acetate Drugs 0.000 claims description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 229940117955 isoamyl acetate Drugs 0.000 claims description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 claims description 2
- 229940090181 propyl acetate Drugs 0.000 claims description 2
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract description 3
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 abstract 1
- 238000000605 extraction Methods 0.000 description 11
- 235000021317 phosphate Nutrition 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 7
- 150000001733 carboxylic acid esters Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 230000010349 pulsation Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- VGONMECBFMCKBS-UHFFFAOYSA-N 2-[[3-(4-methoxyphenyl)-4-oxo-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl]sulfanyl]acetonitrile Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(C=2CCCCC=2S2)=C2N=C1SCC#N VGONMECBFMCKBS-UHFFFAOYSA-N 0.000 description 1
- CPIVYSAVIPTCCX-UHFFFAOYSA-N 4-methylpentan-2-yl acetate Chemical compound CC(C)CC(C)OC(C)=O CPIVYSAVIPTCCX-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- HRKAMJBPFPHCSD-UHFFFAOYSA-N Tri-isobutylphosphate Chemical compound CC(C)COP(=O)(OCC(C)C)OCC(C)C HRKAMJBPFPHCSD-UHFFFAOYSA-N 0.000 description 1
- IZQZNLBFNMTRMF-UHFFFAOYSA-N acetic acid;phosphoric acid Chemical compound CC(O)=O.OP(O)(O)=O IZQZNLBFNMTRMF-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- LBAYFEDWGHXMSM-UHFFFAOYSA-N butaneperoxoic acid Chemical compound CCCC(=O)OO LBAYFEDWGHXMSM-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- QHGRPTNUHWYCEN-UHFFFAOYSA-N dioctyl phenyl phosphate Chemical compound CCCCCCCCOP(=O)(OCCCCCCCC)OC1=CC=CC=C1 QHGRPTNUHWYCEN-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- WVPGXJOLGGFBCR-UHFFFAOYSA-N trioctyl phosphate Chemical class CCCCCCCCOP(=O)(OCCCCCCCC)OCCCCCCCC WVPGXJOLGGFBCR-UHFFFAOYSA-N 0.000 description 1
- QJAVUVZBMMXBRO-UHFFFAOYSA-N tripentyl phosphate Chemical compound CCCCCOP(=O)(OCCCCC)OCCCCC QJAVUVZBMMXBRO-UHFFFAOYSA-N 0.000 description 1
- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Definitions
- the present invention is concerned with a process for the production of water free solutions of percarboxylic acids having two to four carbon atoms.
- organic percarboxylic acid solutions can be produced safely if aqueous solutions of percarboxylic acids having two to four carbon atoms, specifically the peralkanoic acids, 'peracetic acids, perpropionic acid, perisobutyric acid and perbutyric acid, are extracted with organic phosphates having three to 30 carbon atoms whereupon the extract is desorbed with an organic solvent, preferably an ester of a carboxylic acid having four to carbon atoms, e.g., an alkyl alkanoate, and the desorbate of percarboxylic acid and solvent dehydrated, in a given case by azeotropic distillation, if necessary after addition of a carboxylic acid ester boiling below the percarboxylic acid.
- an organic solvent preferably an ester of a carboxylic acid having four to carbon atoms, e.g., an alkyl alkanoate, and the desorbate of percarboxylic acid and solvent dehydrated, in a given case by
- aqueous solutions of percarboxylic acids there are preferably employed those prepared by German Pat. Nos. 1,165,576 and 1,170,926. The entire disclosure of these two German patents is hereby incorporated by reference.
- the concentration of the aqueous percarboxylic acid can be between 10 and percent, preferably 20 to 60 percent.
- phosphate esters there can be employed tertiary phosphates of the formula where R R and R are the same or different and are alkyl, aryl or aralkyl and have a total of three to 30 carbon atoms.
- Suitable extraction agents are trimethyl phosphate, tributyl phosphate, trioctyl phosphates, dioctylphenyl phosphate, triethyl phosphate, tripropyl phosphate, triisobutyl phosphate, triamyl phosphate,
- esters employed to aid in the dehydration can be the same as those set forth above so long as they boil below the percarboxylic acid.
- the extraction is preferably carried out continuously, best by countercurrent operation, namely in conventional extraction apparatus such as for example extraction columns with plates or packing with or without pulsation.
- conventional extraction apparatus such as for example extraction columns with plates or packing with or without pulsation.
- packing there can suitably be added rings, saddles or helices.
- plates there can be used perforated plates, tunnel plates or bubble trays.
- the aqueous percarboxylic acid is fed below the top of the column and the phosphate ester at the lower end of the column.
- a largely water free solution of percarboxylic acid is drawn off at the top of the column while the raffinate which contains negligibly small amounts of active oxygen is withdrawn from the lower end.
- the amount of ester used is determined by special solvent loading curve and by the required coucentration of percarboxylic acid.
- the extract is fed to a thin film evaporator, preferably with moving inner zene, toluene, xylene, and ethyl benzene or mixtures of such solvents.
- a thin film evaporator preferably with moving inner zene, toluene, xylene, and ethyl benzene or mixtures of such solvents.
- carboxylic acid esters containing four to 10 carbon atoms or mixtures containing them.
- ylic acid solution on the lower side is determined by mwherein a portion of the solvent is fed to the lower end dustrial considerations and on the upper side by the of the evaporator in vapor form.
- the solutions therefore can contain a is determined likewise by the required concentration of concentration of to 60 percent, preferably to 50 percarboxylic acid. 10 percent of the percarboxylic acid.
- condensation of the desorbate water containing The extraction can be operated at normal pressure at percarboxylic acid solutions in organic solvents are obtemperatures of 5 to 50C., preferably at 10 to C. tained.
- the water content of the so- The azeotropic dehydration and desorption are carried lution, e.g., does not play a disturbing role so that the Out n a Vacuum a! 20 I0 400 TOIT, p a y 5010 250 organic percarboxylic acid solution is usable directly 15 To he sump temperature is to 100C, preferawithout a previous azeotropic distillation. bly to C.
- the invention is further eXPlaihed y the following the desorbate is preferably fed to a continuously operexamples.
- W ating distillation plant which is provided at the top with V EXAMPLES a separator for the water taken off while the percarbox- 20
- a Apparatus Employed The extraction unit wit the y acid Solution is drawn f l he 59mg necessary equipment consisted of a tube 2 meters long If a carboxylic acid ester having ahigher boiling point d having a diameter of 2.8 cm in which the e Were than the percarboxylic acid is used for the desorption located 40 screens having a hole diamete o 1 then there must be added to the desorbate a carboxylic: The column was pulsated with a pulsation pump and acid ester having a lower boiling point than the percar- 25 operated in countercurrent manner.
- the amount of lower boiling ester can be determined by one skilled in the art by a simple preliminary test.
- organic solvents which are lower boiling than the phosphate esters for example carboxylic acid esters such as those set forth above, chlorinated hydrocarbons, e.g., carbon tetrachloride, chloroform, ethylene dichloride, acety-
- chlorinated hydrocarbons e.g., carbon tetrachloride, chloroform, ethylene dichloride, acety-
- peracids e.g., perpropionic acid and perisobutyric acid can be extracted with equally good success.
- the yield of active oxygen and the purity of the product in such cases corresponds to that with peracetic acid.
- Example C Pressure 250 Torr; Head Temperature: about 42C.
- a process forv the production of water free solutions of percarboxylic acids having two to four carbon atoms comprising extracting the aqueous solution of the percarboxylic acid with a tertiary phosphate ester having three to carbon atoms and desorbing the extract with a solvent for said percarboxylic acid selected from the group consisting of hydrocarbyl alkanoates having four to 10 carbon atoms, chlorinated aliphatic hydrocarbons and aromatic hydrocarbons, said solvent boiling lower than said phosphate ester.
- R R and R are alkyl, aryl or aralkyl.
- a process according to claim 2 including the additional step of removing the final amount of water from the desorbate by azeotropic distillation with a hydro- 4.
- phosphate ester is trimethyl phosphate, tributyl phosphate or trioctyl phosphate.
- hydrocarbyl alkanoate is an alkyl alkanoate.
- hydrocarbyl alkanoate is an alkyl alkanoate or cyclohexyl alkanoate.
- a process according to claim 2 including the ad- 14.
- a process according to claim 13 wherein the alkyl acetate is ethyl acetate.
- the solvent is selected from the group consisting of ethyl acetate, propyl acetate, butyl acetate, amyl acetate, 2- ethyl-hexyl acetate, cyclohexyl acetate, t-butyl acetate, isoamyl acetate, propyl formate, butyl formate, methyl propionate, ethyl propionate, methyl butyrate, ethyl butyrate, methyl valerate, sec.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2145604A DE2145604A1 (de) | 1971-09-13 | 1971-09-13 | Verfahren zur herstellung von organischen loesungen von percarbonsaeuren (v) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3839216A true US3839216A (en) | 1974-10-01 |
Family
ID=5819349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00274965A Expired - Lifetime US3839216A (en) | 1971-09-13 | 1972-07-25 | Process for the production of organic solutions of percarboxylic acids |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3839216A (enrdf_load_stackoverflow) |
| JP (1) | JPS5317576B2 (enrdf_load_stackoverflow) |
| BE (1) | BE788729A (enrdf_load_stackoverflow) |
| CA (1) | CA966857A (enrdf_load_stackoverflow) |
| DE (1) | DE2145604A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2152923B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1358333A (enrdf_load_stackoverflow) |
| NL (1) | NL7208670A (enrdf_load_stackoverflow) |
| SU (1) | SU593661A3 (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3956159A (en) * | 1974-11-25 | 1976-05-11 | The Procter & Gamble Company | Stable concentrated liquid peroxygen bleach composition |
| US4376218A (en) * | 1980-04-26 | 1983-03-08 | Interox Chemicals Limited | Organic peroxide compositions |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5328393A (en) * | 1976-08-27 | 1978-03-16 | Matsushita Electric Ind Co Ltd | Direction finder using color television receiver |
| ES2644056T3 (es) * | 2009-12-22 | 2017-11-27 | Shell Internationale Research Maatschappij B.V. | Procedimiento para recuperar monoalquilbenceno |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3169986A (en) * | 1960-03-22 | 1965-02-16 | Ciba Ltd | Peracid production by ester-h2o2 reaction |
| CA731188A (en) * | 1966-03-29 | Weiberg Otto | Process for the preparation of solutions of pure peracetic acid |
-
1971
- 1971-09-13 DE DE2145604A patent/DE2145604A1/de active Pending
-
1972
- 1972-06-23 NL NL7208670A patent/NL7208670A/xx not_active Application Discontinuation
- 1972-07-25 US US00274965A patent/US3839216A/en not_active Expired - Lifetime
- 1972-09-07 GB GB4155072A patent/GB1358333A/en not_active Expired
- 1972-09-08 SU SU721827028A patent/SU593661A3/ru active
- 1972-09-12 BE BE788729D patent/BE788729A/xx unknown
- 1972-09-13 FR FR7232464A patent/FR2152923B1/fr not_active Expired
- 1972-09-13 CA CA151,625A patent/CA966857A/en not_active Expired
- 1972-09-13 JP JP9220472A patent/JPS5317576B2/ja not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA731188A (en) * | 1966-03-29 | Weiberg Otto | Process for the preparation of solutions of pure peracetic acid | |
| US3169986A (en) * | 1960-03-22 | 1965-02-16 | Ciba Ltd | Peracid production by ester-h2o2 reaction |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3956159A (en) * | 1974-11-25 | 1976-05-11 | The Procter & Gamble Company | Stable concentrated liquid peroxygen bleach composition |
| US4376218A (en) * | 1980-04-26 | 1983-03-08 | Interox Chemicals Limited | Organic peroxide compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2152923B1 (enrdf_load_stackoverflow) | 1975-01-03 |
| BE788729A (fr) | 1973-01-02 |
| GB1358333A (en) | 1974-07-03 |
| NL7208670A (enrdf_load_stackoverflow) | 1973-03-15 |
| SU593661A3 (ru) | 1978-02-15 |
| JPS4836115A (enrdf_load_stackoverflow) | 1973-05-28 |
| FR2152923A1 (enrdf_load_stackoverflow) | 1973-04-27 |
| JPS5317576B2 (enrdf_load_stackoverflow) | 1978-06-09 |
| CA966857A (en) | 1975-04-29 |
| DE2145604A1 (de) | 1973-03-29 |
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