DE2127175C2 - Verfahren zur Herstellung von in unpolaren Kohlenwasserstoffen löslichen gemischten Kupferseifen und ihr Verwendung - Google Patents
Verfahren zur Herstellung von in unpolaren Kohlenwasserstoffen löslichen gemischten Kupferseifen und ihr VerwendungInfo
- Publication number
- DE2127175C2 DE2127175C2 DE2127175A DE2127175A DE2127175C2 DE 2127175 C2 DE2127175 C2 DE 2127175C2 DE 2127175 A DE2127175 A DE 2127175A DE 2127175 A DE2127175 A DE 2127175A DE 2127175 C2 DE2127175 C2 DE 2127175C2
- Authority
- DE
- Germany
- Prior art keywords
- copper
- soaps
- acid
- soluble
- acids
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000010949 copper Substances 0.000 title claims description 152
- 229910052802 copper Inorganic materials 0.000 title claims description 150
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims description 149
- 239000000344 soap Substances 0.000 title claims description 118
- 238000000034 method Methods 0.000 title claims description 21
- 229930195733 hydrocarbon Natural products 0.000 title claims description 17
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims 8
- 239000002253 acid Substances 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 29
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 20
- 239000003921 oil Substances 0.000 claims description 20
- 150000007513 acids Chemical class 0.000 claims description 18
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 17
- 239000011707 mineral Substances 0.000 claims description 17
- 235000015096 spirit Nutrition 0.000 claims description 17
- 238000001556 precipitation Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 239000000446 fuel Substances 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000005749 Copper compound Substances 0.000 claims description 3
- 150000001880 copper compounds Chemical class 0.000 claims description 3
- 239000012454 non-polar solvent Substances 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000004071 soot Substances 0.000 claims description 2
- 239000001293 FEMA 3089 Substances 0.000 claims 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- 241000158728 Meliaceae Species 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 235000011037 adipic acid Nutrition 0.000 claims 1
- 239000001361 adipic acid Substances 0.000 claims 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000000417 fungicide Substances 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 230000003137 locomotive effect Effects 0.000 claims 1
- 230000014759 maintenance of location Effects 0.000 claims 1
- 125000005608 naphthenic acid group Chemical group 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 62
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 14
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 13
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 13
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 12
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- -1 ι - Chemical compound 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 6
- 150000002762 monocarboxylic acid derivatives Chemical group 0.000 description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 4
- MHPUGCYGQWGLJL-UHFFFAOYSA-N 5-methyl-hexanoic acid Chemical compound CC(C)CCCC(O)=O MHPUGCYGQWGLJL-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 239000005750 Copper hydroxide Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910001956 copper hydroxide Inorganic materials 0.000 description 3
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 3
- AEJIMXVJZFYIHN-UHFFFAOYSA-N copper;dihydrate Chemical compound O.O.[Cu] AEJIMXVJZFYIHN-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- WOWYPHJOHOCYII-VOTSOKGWSA-N (e)-2-ethylhex-2-enoic acid Chemical compound CCC\C=C(/CC)C(O)=O WOWYPHJOHOCYII-VOTSOKGWSA-N 0.000 description 2
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 2
- XTCNGAJYWUIFFB-UHFFFAOYSA-N 2-ethyl-4-methylpentanoic acid Chemical compound CCC(C(O)=O)CC(C)C XTCNGAJYWUIFFB-UHFFFAOYSA-N 0.000 description 2
- KUSYIGBGHPOWEL-UHFFFAOYSA-N 2-methyl nonaoic acid Chemical compound CCCCCCCC(C)C(O)=O KUSYIGBGHPOWEL-UHFFFAOYSA-N 0.000 description 2
- OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 2
- JOTRMYCCALXLNJ-UHFFFAOYSA-N 3-ethyl-4-methylpentanoic acid Chemical compound CCC(C(C)C)CC(O)=O JOTRMYCCALXLNJ-UHFFFAOYSA-N 0.000 description 2
- ATUUSOSLBXVJKL-UHFFFAOYSA-N 3-ethylpentanoic acid Chemical compound CCC(CC)CC(O)=O ATUUSOSLBXVJKL-UHFFFAOYSA-N 0.000 description 2
- LRWDNFIBQNGKFJ-UHFFFAOYSA-N 4-ethyl-5,5-dimethylhexanoic acid Chemical compound CCC(C(C)(C)C)CCC(O)=O LRWDNFIBQNGKFJ-UHFFFAOYSA-N 0.000 description 2
- DIVCBWJKVSFZKJ-UHFFFAOYSA-N 4-methyl-hexanoic acid Chemical compound CCC(C)CCC(O)=O DIVCBWJKVSFZKJ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000005643 Pelargonic acid Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- ZRYCZAWRXHAAPZ-UHFFFAOYSA-N alpha,alpha-dimethyl valeric acid Chemical compound CCCC(C)(C)C(O)=O ZRYCZAWRXHAAPZ-UHFFFAOYSA-N 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- KLKMXKACEROVRH-UHFFFAOYSA-L copper;3,5,5-trimethylhexanoate Chemical compound [Cu+2].[O-]C(=O)CC(C)CC(C)(C)C.[O-]C(=O)CC(C)CC(C)(C)C KLKMXKACEROVRH-UHFFFAOYSA-L 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000006069 physical mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 239000008149 soap solution Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- 229960002703 undecylenic acid Drugs 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 239000001602 (E)-hex-3-enoic acid Substances 0.000 description 1
- UDILKAAYNUPREE-UHFFFAOYSA-N 2,2,4,4-tetramethylpentanoic acid Chemical compound CC(C)(C)CC(C)(C)C(O)=O UDILKAAYNUPREE-UHFFFAOYSA-N 0.000 description 1
- VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical compound CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-UHFFFAOYSA-N 0.000 description 1
- QRMMMWOSHHVOCJ-UHFFFAOYSA-N 2,2-dimethylheptanoic acid Chemical compound CCCCCC(C)(C)C(O)=O QRMMMWOSHHVOCJ-UHFFFAOYSA-N 0.000 description 1
- OWEMTCOXFULTNW-UHFFFAOYSA-N 2,3-dimethyl-2-propan-2-ylbutanoic acid Chemical compound CC(C)C(C)(C(C)C)C(O)=O OWEMTCOXFULTNW-UHFFFAOYSA-N 0.000 description 1
- LBUDVZDSWKZABS-UHFFFAOYSA-N 2,3-dimethylpentanoic acid Chemical compound CCC(C)C(C)C(O)=O LBUDVZDSWKZABS-UHFFFAOYSA-N 0.000 description 1
- ASAHZDPKCCONIV-UHFFFAOYSA-N 2,5-dimethylhexanoic acid Chemical compound CC(C)CCC(C)C(O)=O ASAHZDPKCCONIV-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-BYPYZUCNSA-N 2-Methylbutanoic acid Natural products CC[C@H](C)C(O)=O WLAMNBDJUVNPJU-BYPYZUCNSA-N 0.000 description 1
- MAQIPNRKAZZHBJ-UHFFFAOYSA-N 2-ethyl-5-methylhexanoic acid Chemical compound CCC(C(O)=O)CCC(C)C MAQIPNRKAZZHBJ-UHFFFAOYSA-N 0.000 description 1
- DMUXSGAKEXSNGN-UHFFFAOYSA-N 2-ethyloctanoic acid Chemical compound CCCCCCC(CC)C(O)=O DMUXSGAKEXSNGN-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- RXGPYPPCEXISOV-UHFFFAOYSA-N 2-propylheptanoic acid Chemical compound CCCCCC(C(O)=O)CCC RXGPYPPCEXISOV-UHFFFAOYSA-N 0.000 description 1
- HWXRWNDOEKHFTL-UHFFFAOYSA-N 2-propylhexanoic acid Chemical compound CCCCC(C(O)=O)CCC HWXRWNDOEKHFTL-UHFFFAOYSA-N 0.000 description 1
- MLMQPDHYNJCQAO-UHFFFAOYSA-N 3,3-dimethylbutyric acid Chemical compound CC(C)(C)CC(O)=O MLMQPDHYNJCQAO-UHFFFAOYSA-N 0.000 description 1
- KTWWTCBUJPAASC-UHFFFAOYSA-N 3,5-dimethylhexanoic acid Chemical compound CC(C)CC(C)CC(O)=O KTWWTCBUJPAASC-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- XYDYODCWVCBIOQ-UHFFFAOYSA-N 3-ethyl-2,2-dimethylhexane Chemical compound CCCC(CC)C(C)(C)C XYDYODCWVCBIOQ-UHFFFAOYSA-N 0.000 description 1
- KOWGPBWKHLXKDZ-UHFFFAOYSA-N 3-ethylnonanoic acid Chemical compound CCCCCCC(CC)CC(O)=O KOWGPBWKHLXKDZ-UHFFFAOYSA-N 0.000 description 1
- YKSWLQPMYFCNBG-UHFFFAOYSA-N 3-methyl-octanoic acid Chemical compound CCCCCC(C)CC(O)=O YKSWLQPMYFCNBG-UHFFFAOYSA-N 0.000 description 1
- VSWVHHCWUCZFBB-UHFFFAOYSA-N 3-propylhexanoic acid Chemical compound CCCC(CCC)CC(O)=O VSWVHHCWUCZFBB-UHFFFAOYSA-N 0.000 description 1
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3MC7 Natural products CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 1
- VZPIUNDOWLDCTC-UHFFFAOYSA-N 4,8-dimethylnonanoic acid Chemical compound CC(C)CCCC(C)CCC(O)=O VZPIUNDOWLDCTC-UHFFFAOYSA-N 0.000 description 1
- PWKJMPFEQOHBAC-UHFFFAOYSA-N 4-Ethyloctanoic acid Chemical compound CCCCC(CC)CCC(O)=O PWKJMPFEQOHBAC-UHFFFAOYSA-N 0.000 description 1
- CYNQKJPFHUKKSF-UHFFFAOYSA-N 4-methyl-2-propylpentanoic acid Chemical compound CCCC(C(O)=O)CC(C)C CYNQKJPFHUKKSF-UHFFFAOYSA-N 0.000 description 1
- NODQTVSOELONGZ-UHFFFAOYSA-N 4-methyl-decanoic acid Chemical compound CCCCCCC(C)CCC(O)=O NODQTVSOELONGZ-UHFFFAOYSA-N 0.000 description 1
- TXHYZZFKHAHBEZ-UHFFFAOYSA-N 5-ethyl-6-methylheptanoic acid Chemical compound CCC(C(C)C)CCCC(O)=O TXHYZZFKHAHBEZ-UHFFFAOYSA-N 0.000 description 1
- DHODJQDPMFRMDA-UHFFFAOYSA-N 5-methyl-2-propylhexanoic acid Chemical compound CCCC(C(O)=O)CCC(C)C DHODJQDPMFRMDA-UHFFFAOYSA-N 0.000 description 1
- OJTHHBCWUMTZEY-UHFFFAOYSA-N 5-methyl-heptanoic acid Chemical compound CCC(C)CCCC(O)=O OJTHHBCWUMTZEY-UHFFFAOYSA-N 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XXHDAWYDNSXJQM-UHFFFAOYSA-N Chloride-3-Hexenoic acid Natural products CCC=CCC(O)=O XXHDAWYDNSXJQM-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- UPURPFNAFBQPON-UHFFFAOYSA-N beta,beta-dimethyl valeric acid Chemical compound CCC(C)(C)CC(O)=O UPURPFNAFBQPON-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940116318 copper carbonate Drugs 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- SEKCXMNFUDONGJ-UHFFFAOYSA-L copper;2-ethylhexanoate Chemical compound [Cu+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O SEKCXMNFUDONGJ-UHFFFAOYSA-L 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- 229920001887 crystalline plastic Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ACXGEQOZKSSXKV-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O.CCCCCCCC(O)=O ACXGEQOZKSSXKV-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 239000004535 oil miscible liquid Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
- ZHVCSGCGBCHVLW-UHFFFAOYSA-M sodium;3,5,5-trimethylhexanoate Chemical compound [Na+].[O-]C(=O)CC(C)CC(C)(C)C ZHVCSGCGBCHVLW-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- XXHDAWYDNSXJQM-ONEGZZNKSA-N trans-hex-3-enoic acid Chemical compound CC\C=C\CC(O)=O XXHDAWYDNSXJQM-ONEGZZNKSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/188—Carboxylic acids; metal salts thereof
- C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
- C07C53/128—Acids containing more than four carbon atoms the carboxylic group being bound to a carbon atom bound to at least two other carbon atoms, e.g. neo-acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)
- Lubricants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4253670A | 1970-06-01 | 1970-06-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2127175A1 DE2127175A1 (de) | 1971-12-09 |
| DE2127175C2 true DE2127175C2 (de) | 1982-04-01 |
Family
ID=21922460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2127175A Expired DE2127175C2 (de) | 1970-06-01 | 1971-06-01 | Verfahren zur Herstellung von in unpolaren Kohlenwasserstoffen löslichen gemischten Kupferseifen und ihr Verwendung |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3701729A (fr) |
| JP (1) | JPS5327724B1 (fr) |
| BE (1) | BE767235A (fr) |
| CA (1) | CA965429A (fr) |
| DE (1) | DE2127175C2 (fr) |
| ES (1) | ES391456A1 (fr) |
| FR (1) | FR2095682A5 (fr) |
| GB (1) | GB1335257A (fr) |
| NL (1) | NL7107496A (fr) |
| NO (1) | NO136093C (fr) |
| SE (1) | SE397673B (fr) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4162986A (en) * | 1977-06-20 | 1979-07-31 | Mooney Chemicals, Inc. | Oil-soluble high metal content transitional metal organic oxy, hydroxy, complexes |
| GB2056482A (en) * | 1979-08-13 | 1981-03-18 | Exxon Research Engineering Co | Lubricating oil compositions |
| FR2514643B1 (fr) * | 1981-10-20 | 1986-07-04 | Oreal | Lanolate de cuivre et compositions cosmetiques anti-acneiques le contenant |
| WO1985001513A1 (fr) * | 1983-10-05 | 1985-04-11 | The Lubrizol Corporation | Compositions contenant du manganese et du cuivre |
| AU581691B2 (en) * | 1985-10-14 | 1989-03-02 | Balfour Manufacturing Company Limited | Process for the production of feedstuffs |
| US5275630A (en) * | 1986-11-06 | 1994-01-04 | The Lubrizol Corporation | Metal salt fuel additive stabilized with a thiadiazole |
| DK0632008T3 (da) * | 1993-06-01 | 1998-09-23 | Ono Pharmaceutical Co | Pentansyrederivater |
| US5672746A (en) | 1994-08-30 | 1997-09-30 | American Biogenetic Sciences, Inc. | Antiproliferative and neurotrophic molecules |
| US6300373B1 (en) | 1993-09-10 | 2001-10-09 | American Biogenetic Sciences, Inc. | Antiproliferative and neurotrophic molecules |
| WO1999066920A1 (fr) | 1998-06-22 | 1999-12-29 | American Biogenetic Sciences, Inc. | Utilisation d'un analogue d'acide valproique dans le traitement et la prevention de migraine et de maladies affectives |
| CN1839111B (zh) | 2003-07-25 | 2010-04-21 | 普罗米蒂克生物科学公司 | 中链脂肪酸金属盐的制备方法 |
| CN109503358A (zh) * | 2019-01-07 | 2019-03-22 | 宁波赜军医药科技有限公司 | 一种异辛酸铜的制备方法 |
-
1970
- 1970-06-01 US US42536A patent/US3701729A/en not_active Expired - Lifetime
-
1971
- 1971-05-14 BE BE767235A patent/BE767235A/fr not_active IP Right Cessation
- 1971-05-17 GB GB1521771*[A patent/GB1335257A/en not_active Expired
- 1971-05-22 ES ES391456A patent/ES391456A1/es not_active Expired
- 1971-05-26 SE SE7106813A patent/SE397673B/xx unknown
- 1971-05-28 NO NO2027/71A patent/NO136093C/no unknown
- 1971-05-28 FR FR7119485A patent/FR2095682A5/fr not_active Expired
- 1971-05-31 JP JP3709371A patent/JPS5327724B1/ja active Pending
- 1971-06-01 NL NL7107496A patent/NL7107496A/xx not_active Application Discontinuation
- 1971-06-01 CA CA114,552A patent/CA965429A/en not_active Expired
- 1971-06-01 DE DE2127175A patent/DE2127175C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NO136093B (fr) | 1977-04-12 |
| BE767235A (fr) | 1971-10-01 |
| FR2095682A5 (fr) | 1972-02-11 |
| NO136093C (no) | 1977-07-20 |
| ES391456A1 (es) | 1973-06-16 |
| SE397673B (sv) | 1977-11-14 |
| JPS5327724B1 (fr) | 1978-08-10 |
| CA965429A (en) | 1975-04-01 |
| DE2127175A1 (de) | 1971-12-09 |
| US3701729A (en) | 1972-10-31 |
| GB1335257A (en) | 1973-10-24 |
| NL7107496A (fr) | 1971-12-03 |
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| OD | Request for examination | ||
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| 8327 | Change in the person/name/address of the patent owner |
Owner name: NUODEX INC., PISCATAWAY, N.J., US |
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Free format text: JUNG, E., DIPL.-CHEM. DR.PHIL. SCHIRDEWAHN, J., DIPL.-PHYS. DR.RER.NAT. GERNHARDT, C., DIPL.-ING., PAT.-ANW., 8000 MUENCHEN |