BE443658A - Acides sulfoniques ou éthers-sels de l'acide sulfurique et procédé de préparation de ces produits - Google Patents
Acides sulfoniques ou éthers-sels de l'acide sulfurique et procédé de préparation de ces produitsInfo
- Publication number
- BE443658A BE443658A BE443658A BE443658A BE443658A BE 443658 A BE443658 A BE 443658A BE 443658 A BE443658 A BE 443658A BE 443658 A BE443658 A BE 443658A BE 443658 A BE443658 A BE 443658A
- Authority
- BE
- Belgium
- Prior art keywords
- parts
- salts
- reaction
- acid
- hydrocarbons
- Prior art date
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title claims description 21
- 239000002253 acid Substances 0.000 title description 23
- 150000007513 acids Chemical class 0.000 title description 14
- -1 ethers salts Chemical class 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 229930195733 hydrocarbon Natural products 0.000 claims description 28
- 150000002430 hydrocarbons Chemical class 0.000 claims description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 14
- 230000005855 radiation Effects 0.000 claims description 12
- 150000003460 sulfonic acids Chemical class 0.000 claims description 12
- 150000001298 alcohols Chemical class 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 33
- 235000010269 sulphur dioxide Nutrition 0.000 description 21
- 239000000243 solution Substances 0.000 description 17
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 235000011152 sodium sulphate Nutrition 0.000 description 14
- 239000003921 oil Substances 0.000 description 13
- 159000000000 sodium salts Chemical class 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000010453 quartz Substances 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000007789 gas Substances 0.000 description 9
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 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 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 238000006386 neutralization reaction Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 235000019260 propionic acid Nutrition 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
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 159000000009 barium salts Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- ZHGASCUQXLPSDT-UHFFFAOYSA-N cyclohexanesulfonic acid Chemical compound OS(=O)(=O)C1CCCCC1 ZHGASCUQXLPSDT-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 239000011833 salt mixture Substances 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
- KMBRJVMBQNMRDM-UHFFFAOYSA-N 1-hydroxybutane-1-sulfonic acid Chemical class CCCC(O)S(O)(=O)=O KMBRJVMBQNMRDM-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- VZWGRQBCURJOMT-UHFFFAOYSA-N Dodecyl acetate Chemical compound CCCCCCCCCCCCOC(C)=O VZWGRQBCURJOMT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- GHDIHPNJQVDFBL-UHFFFAOYSA-N methoxycyclohexane Chemical compound COC1CCCCC1 GHDIHPNJQVDFBL-UHFFFAOYSA-N 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 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
- NQAWQSVOOHTLEY-UHFFFAOYSA-N 1-chlorobutane-1-sulfonic acid Chemical class CCCC(Cl)S(O)(=O)=O NQAWQSVOOHTLEY-UHFFFAOYSA-N 0.000 description 1
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
- LHLXUCFDVUOWFH-UHFFFAOYSA-N 1-chlorododecane;sodium Chemical compound [Na].CCCCCCCCCCCCCl LHLXUCFDVUOWFH-UHFFFAOYSA-N 0.000 description 1
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 1
- MRTWZIXSCCETHN-UHFFFAOYSA-N 2-sulfododecanoic acid Chemical compound CCCCCCCCCCC(C(O)=O)S(O)(=O)=O MRTWZIXSCCETHN-UHFFFAOYSA-N 0.000 description 1
- POIDVYDKDFVASM-UHFFFAOYSA-N 3-methylheptane-1-sulfonic acid Chemical class CCCCC(C)CCS(O)(=O)=O POIDVYDKDFVASM-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- UPBLAVFWWWKVAJ-UHFFFAOYSA-N [Cl].CCC Chemical class [Cl].CCC UPBLAVFWWWKVAJ-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- VFGRALUHHHDIQI-UHFFFAOYSA-N butyl 2-hydroxyacetate Chemical compound CCCCOC(=O)CO VFGRALUHHHDIQI-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- GLYJVQDYLFAUFC-UHFFFAOYSA-N hexadecanoic acid butyl ester Natural products CCCCCCCCCCCCCCCC(=O)OCCCC GLYJVQDYLFAUFC-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- WVJVHUWVQNLPCR-UHFFFAOYSA-N octadecanoyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCC WVJVHUWVQNLPCR-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002943 palmitic acids Chemical class 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- IJOUABYAFSBQRU-UHFFFAOYSA-M sodium 2-sulfododecanoate Chemical compound [Na+].CCCCCCCCCCC(C([O-])=O)S(O)(=O)=O IJOUABYAFSBQRU-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- MKAXISKDFRQLBH-UHFFFAOYSA-M sodium;2-methylpropane-1-sulfonate Chemical compound [Na+].CC(C)CS([O-])(=O)=O MKAXISKDFRQLBH-UHFFFAOYSA-M 0.000 description 1
- NGDIAZZSCVVCEW-UHFFFAOYSA-M sodium;butyl sulfate Chemical compound [Na+].CCCCOS([O-])(=O)=O NGDIAZZSCVVCEW-UHFFFAOYSA-M 0.000 description 1
- DIIKAKPJAGLSOD-UHFFFAOYSA-M sodium;cyclohexanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1CCCCC1 DIIKAKPJAGLSOD-UHFFFAOYSA-M 0.000 description 1
- DZXBHDRHRFLQCJ-UHFFFAOYSA-M sodium;methyl sulfate Chemical compound [Na+].COS([O-])(=O)=O DZXBHDRHRFLQCJ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- AGGIJOLULBJGTQ-UHFFFAOYSA-N sulfoacetic acid Chemical compound OC(=O)CS(O)(=O)=O AGGIJOLULBJGTQ-UHFFFAOYSA-N 0.000 description 1
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical compound OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/14—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by sulfoxidation, i.e. by reaction with sulfur dioxide and oxygen with formation of sulfo or halosulfonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C14/00—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material
- C23C14/04—Coating on selected surface areas, e.g. using masks
-
- G—PHYSICS
- G04—HOROLOGY
- G04B—MECHANICALLY-DRIVEN CLOCKS OR WATCHES; MECHANICAL PARTS OF CLOCKS OR WATCHES IN GENERAL; TIME PIECES USING THE POSITION OF THE SUN, MOON OR STARS
- G04B37/00—Cases
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G4/00—Fixed capacitors; Processes of their manufacture
- H01G4/28—Tubular capacitors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G4/00—Fixed capacitors; Processes of their manufacture
- H01G4/30—Stacked capacitors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G5/00—Capacitors in which the capacitance is varied by mechanical means, e.g. by turning a shaft; Processes of their manufacture
- H01G5/38—Multiple capacitors, e.g. ganged
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
-
- H—ELECTRICITY
- H03—ELECTRONIC CIRCUITRY
- H03J—TUNING RESONANT CIRCUITS; SELECTING RESONANT CIRCUITS
- H03J3/00—Continuous tuning
- H03J3/20—Continuous tuning of single resonant circuit by varying inductance only or capacitance only
Landscapes
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing & Machinery (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI0068390 | 1940-12-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE443658A true BE443658A (fr) | 1942-01-31 |
Family
ID=7196871
Family Applications (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE443658A BE443658A (fr) | 1940-12-09 | 1941-12-09 | Acides sulfoniques ou éthers-sels de l'acide sulfurique et procédé de préparation de ces produits |
| BE444546A BE444546R (fr) | 1940-12-09 | 1942-02-09 | Acides sulfoniques ou éthers-sels de l'acide sulfurique et procédé de préparation de ces produits |
| BE445312A BE445312R (fr) | 1940-12-09 | 1942-04-23 | Acides sulfoniques ou éthers-sels de l'acide sulfurique et procédé de préparation de ces produits |
| BE445349A BE445349R (fr) | 1940-12-09 | 1942-04-27 | Acides sulfoniques ou éthers-sels de l'acide sulfurique et procédé de préparation de ces produits |
| BE450081A BE450081R (fr) | 1940-12-09 | 1943-04-09 | Acides sulfoniques ou éthers-sels de l'acide sulfurique et procédé de préparation de ces produits |
| BE457246A BE457246R (fr) | 1940-12-09 | 1944-08-17 | Acides sulfoniques ou éthers-sels de l'acide sulfurique et procédé de préparation de ces produits |
| BE457247A BE457247R (fr) | 1940-12-09 | 1944-08-17 | Acides sulfoniques ou éthers-sels de l'acide sulfurique et procédé de préparation de ces produits |
| BE457245A BE457245R (fr) | 1940-12-09 | 1959-03-28 | Acides sulfoniques ou éthers-sels de l'acide sulfurique et procédé de préparation de ces produits |
Family Applications After (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE444546A BE444546R (fr) | 1940-12-09 | 1942-02-09 | Acides sulfoniques ou éthers-sels de l'acide sulfurique et procédé de préparation de ces produits |
| BE445312A BE445312R (fr) | 1940-12-09 | 1942-04-23 | Acides sulfoniques ou éthers-sels de l'acide sulfurique et procédé de préparation de ces produits |
| BE445349A BE445349R (fr) | 1940-12-09 | 1942-04-27 | Acides sulfoniques ou éthers-sels de l'acide sulfurique et procédé de préparation de ces produits |
| BE450081A BE450081R (fr) | 1940-12-09 | 1943-04-09 | Acides sulfoniques ou éthers-sels de l'acide sulfurique et procédé de préparation de ces produits |
| BE457246A BE457246R (fr) | 1940-12-09 | 1944-08-17 | Acides sulfoniques ou éthers-sels de l'acide sulfurique et procédé de préparation de ces produits |
| BE457247A BE457247R (fr) | 1940-12-09 | 1944-08-17 | Acides sulfoniques ou éthers-sels de l'acide sulfurique et procédé de préparation de ces produits |
| BE457245A BE457245R (fr) | 1940-12-09 | 1959-03-28 | Acides sulfoniques ou éthers-sels de l'acide sulfurique et procédé de préparation de ces produits |
Country Status (4)
| Country | Link |
|---|---|
| BE (8) | BE443658A (de) |
| CH (1) | CH228209A (de) |
| DE (1) | DE735096C (de) |
| FR (1) | FR877672A (de) |
Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE910165C (de) * | 1943-01-15 | 1954-04-29 | Hoechst Ag | Verfahren zur Herstellung von Sulfonsaeuren |
| US2503280A (en) * | 1947-10-24 | 1950-04-11 | Du Pont | Azo catalysts in preparation of sulfonic acids |
| US2507088A (en) * | 1948-01-08 | 1950-05-09 | Du Pont | Sulfoxidation process |
| DE872942C (de) * | 1948-10-02 | 1953-04-09 | Krupp Kohlechemie G M B H | Verfahren zur Sulfoxydation von sauerstoffhaltigen Derivaten gesaettigter aliphatischer oder cycloaliphatischer Kohlenwasserstoffe |
| DE967238C (de) * | 1953-02-06 | 1957-10-24 | Basf Ag | Leicht emulgierbare oder kolloidal loesliche Wachsprodukte |
| DE1014067B (de) * | 1953-07-29 | 1957-08-22 | Basf Ag | Netzmittel fuer Merzerisier- und Laugierbaeder |
| DE1139116B (de) * | 1956-02-03 | 1962-11-08 | Exxon Research Engineering Co | Verfahren zur Herstellung von aliphatischen und cycloaliphatischen Sulfonsaeuren |
| US3507909A (en) * | 1968-01-22 | 1970-04-21 | Phillips Petroleum Co | Production of sulfonate salts of lighter color |
| DE3304017A1 (de) * | 1983-02-07 | 1984-08-09 | Hoechst Ag, 6230 Frankfurt | Verfahren zur isolierung von paraffinsulfonat aus dem bei der sulfoxydation von paraffinen erhaltenen reaktionsgemisch |
| US5075026A (en) * | 1986-05-21 | 1991-12-24 | Colgate-Palmolive Company | Microemulsion all purpose liquid cleaning composition |
| US5236614A (en) | 1990-09-25 | 1993-08-17 | Colgate-Palmolive Company | Stable microemulsion disinfecting detergent composition |
| US6669929B1 (en) | 2002-12-30 | 2003-12-30 | Colgate Palmolive Company | Dentifrice containing functional film flakes |
| PT1853689E (pt) | 2005-02-15 | 2012-10-15 | Colgate Palmolive Co | Composições de fragrancias que reduzem ou eliminam maus odores, os métodos e composições de limpeza relacionados com as mesmas |
| NZ560475A (en) | 2005-02-15 | 2010-12-24 | Colgate Palmolive Co | Cleaning compositions that provide grease removal and fragance delivery |
| PL2016164T3 (pl) | 2006-04-21 | 2012-03-30 | Colgate Palmolive Co | Kompozycja z widocznością i wpływem zawieszonych materiałów |
| US7749949B2 (en) | 2006-12-15 | 2010-07-06 | Colgate-Palmolive Company | Liquid detergent composition comprising an acrylic polymer/ propylene glycol ether of methyl glucose mixture |
| DE102007020697A1 (de) | 2007-05-03 | 2008-11-06 | Clariant International Ltd. | Verfahren zur Isolierung konzentrierter Paraffinsulfonsäuren |
| EP2014755B1 (de) | 2007-05-29 | 2012-03-21 | The Procter & Gamble Company | Verfahren zum Reinigen von Geschirr |
| ES2473615T3 (es) | 2007-12-18 | 2014-07-07 | Colgate-Palmolive Company | Composiciones y métodos de limpieza desengrasantes universales |
| WO2009078868A1 (en) | 2007-12-18 | 2009-06-25 | Colgate-Palmolive Company | Alkaline cleaning compositions |
| EP2083066A1 (de) | 2008-01-22 | 2009-07-29 | The Procter and Gamble Company | Flüssige Reinigungsmittelzusammensetzung |
| AR072859A1 (es) | 2008-05-23 | 2010-09-29 | Colgate Palmolive Co | Metodos y composiciones liquidas de limpieza |
| WO2009143091A1 (en) | 2008-05-23 | 2009-11-26 | Colgate-Palmolive Company | Liquid cleaning compositions and manufacture |
| DE102008032723A1 (de) | 2008-07-11 | 2010-01-14 | Clariant International Limited | Verfahren zur Isolierung von Paraffinsulfonsäuren |
| WO2010126742A1 (en) | 2009-05-01 | 2010-11-04 | Colgate-Palmolive Company | Liquid cleaning composition with films |
| ES2412684T3 (es) | 2009-06-19 | 2013-07-12 | The Procter & Gamble Company | Composición detergente de lavado de vajillas a mano líquida |
| EP2264138B2 (de) | 2009-06-19 | 2023-03-08 | The Procter & Gamble Company | Flüssige Handspülmittelzusammensetzung |
| US20110150817A1 (en) | 2009-12-17 | 2011-06-23 | Ricky Ah-Man Woo | Freshening compositions comprising malodor binding polymers and malodor control components |
| EP2338961A1 (de) | 2009-12-22 | 2011-06-29 | The Procter & Gamble Company | Alkalisches flüssiges Handgeschirrspülmittel |
| JP5727610B2 (ja) | 2010-08-17 | 2015-06-03 | ザ プロクター アンド ギャンブルカンパニー | 持続性の泡を有する、食器を手洗いする方法 |
| PL2420558T3 (pl) | 2010-08-17 | 2017-12-29 | The Procter And Gamble Company | Stabilne, trwałe detergenty do ręcznego zmywania naczyń |
| AU2010365414B2 (en) | 2010-12-13 | 2014-07-10 | Colgate-Palmolive Company | Dilutable concentrated cleaning composition |
| US9862913B2 (en) | 2010-12-13 | 2018-01-09 | Colgate-Palmolive Company | Dilutable concentrated cleaning composition |
| US20130150276A1 (en) | 2011-12-09 | 2013-06-13 | The Procter & Gamble Company | Method of providing fast drying and/or delivering shine on hard surfaces |
| US9750670B2 (en) | 2012-12-19 | 2017-09-05 | Colgate-Palmolive Company | Zinc amino acid complex with cysteine |
| AU2012397265B2 (en) | 2012-12-19 | 2016-02-25 | Colgate-Palmolive Company | Oral gel comprising zinc - amino acid complex |
| CN107308013A (zh) | 2012-12-19 | 2017-11-03 | 高露洁-棕榄公司 | 锌‑赖氨酸络合物 |
| MX353216B (es) | 2012-12-19 | 2018-01-08 | Colgate Palmolive Co | Productos antitranspirantes con proteinas y sales antitranspirantes. |
| WO2014098826A1 (en) | 2012-12-19 | 2014-06-26 | Colgate-Palmolive Company | Oral care compositions comprising zinc amino acid halides |
| US9901523B2 (en) | 2012-12-19 | 2018-02-27 | Colgate-Palmolive Company | Oral care products comprising zinc oxide and trimethylglycine |
| KR20150097494A (ko) | 2012-12-19 | 2015-08-26 | 콜게이트-파아므올리브캄파니 | 4 염기성 아연 아미노산 할로겐화물 착물을 포함하는 구강 관리 제품 |
| EP2934444B1 (de) | 2012-12-19 | 2016-11-30 | Colgate-Palmolive Company | Mundpflegeprodukte mit tetrabasischem zinkchlorid und trimethylglycin |
| US9675823B2 (en) | 2012-12-19 | 2017-06-13 | Colgate-Palmolive Company | Two component compositions containing zinc amino acid halide complexes and cysteine |
| US10188112B2 (en) | 2012-12-19 | 2019-01-29 | Colgate-Palmolive Company | Personal cleansing compositions containing zinc amino acid/trimethylglycine halide |
| WO2014098828A1 (en) | 2012-12-19 | 2014-06-26 | Colgate-Palmolive Company | Teeth whitening methods, visually perceptible signals and compositions therefor|comprising zinc amino acid halides |
| EP2934696B1 (de) | 2012-12-19 | 2017-07-26 | Colgate-Palmolive Company | Zink-aminosäure-halogenidkomplex mit cystein |
| US9504858B2 (en) | 2012-12-19 | 2016-11-29 | Colgate-Palmolive Company | Zinc amino acid halide complex with cysteine |
| RU2648513C2 (ru) | 2012-12-19 | 2018-03-26 | Колгейт-Палмолив Компани | Ополаскиватель для полости рта с галогенидом цинка-аминокислоты |
| US9925130B2 (en) | 2012-12-19 | 2018-03-27 | Colgate-Palmolive Company | Composition with zinc amino acid/trimethylglycine halide precursors |
| US9498421B2 (en) | 2012-12-19 | 2016-11-22 | Colgate-Palmolive Company | Two component compositions containing tetrabasic zinc-amino acid halide complexes and cysteine |
| EP2934438B1 (de) | 2012-12-19 | 2017-02-15 | Colgate-Palmolive Company | Zinkaminosäure-/trimethylglycinhalide |
| US10196589B2 (en) | 2016-02-15 | 2019-02-05 | Hercules Llc | Home care composition comprising a mixed hydrophobically modified cationic polysaccharide |
| EP3487971A1 (de) | 2016-07-22 | 2019-05-29 | The Procter and Gamble Company | Geschirrspülmittelzusammensetzung |
| WO2020139337A1 (en) | 2018-12-27 | 2020-07-02 | Colgate-Palmolive Company | Home care compositions |
| CN113646479B (zh) | 2019-01-17 | 2023-06-13 | 埃斯普投资有限公司 | 强化非角蛋白纤维的方法及其用途 |
| EP4074812A1 (de) | 2021-04-15 | 2022-10-19 | Henkel AG & Co. KGaA | Beutel mit einer handgeschirrspülzusammensetzung |
-
1940
- 1940-12-10 DE DEI68390D patent/DE735096C/de not_active Expired
-
1941
- 1941-11-15 CH CH228209D patent/CH228209A/de unknown
- 1941-12-09 BE BE443658A patent/BE443658A/fr unknown
- 1941-12-11 FR FR877672D patent/FR877672A/fr not_active Expired
-
1942
- 1942-02-09 BE BE444546A patent/BE444546R/xx active
- 1942-04-23 BE BE445312A patent/BE445312R/fr active
- 1942-04-27 BE BE445349A patent/BE445349R/fr active
-
1943
- 1943-04-09 BE BE450081A patent/BE450081R/fr active
-
1944
- 1944-08-17 BE BE457246A patent/BE457246R/fr active
- 1944-08-17 BE BE457247A patent/BE457247R/fr active
-
1959
- 1959-03-28 BE BE457245A patent/BE457245R/fr active
Also Published As
| Publication number | Publication date |
|---|---|
| DE735096C (de) | 1943-05-06 |
| BE444546R (fr) | 1942-03-31 |
| BE457247R (fr) | 1944-09-30 |
| CH228209A (de) | 1943-08-15 |
| BE450081R (fr) | 1943-05-31 |
| FR877672A (fr) | 1942-12-14 |
| BE445349R (fr) | 1942-05-30 |
| BE457246R (fr) | 1944-09-30 |
| BE445312R (fr) | 1942-05-30 |
| BE457245R (fr) | 1944-09-30 |
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