JPS6129761B2 - - Google Patents
Info
- Publication number
- JPS6129761B2 JPS6129761B2 JP53149351A JP14935178A JPS6129761B2 JP S6129761 B2 JPS6129761 B2 JP S6129761B2 JP 53149351 A JP53149351 A JP 53149351A JP 14935178 A JP14935178 A JP 14935178A JP S6129761 B2 JPS6129761 B2 JP S6129761B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- salt
- higher fatty
- item
- oil
- 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
- 239000003921 oil Substances 0.000 claims description 144
- -1 amine salt Chemical class 0.000 claims description 76
- 238000000034 method Methods 0.000 claims description 62
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 53
- 229930195729 fatty acid Natural products 0.000 claims description 53
- 239000000194 fatty acid Substances 0.000 claims description 53
- 150000004665 fatty acids Chemical class 0.000 claims description 43
- 238000005555 metalworking Methods 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 27
- 229910052751 metal Inorganic materials 0.000 claims description 25
- 239000002184 metal Substances 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000002252 acyl group Chemical group 0.000 claims description 20
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 18
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 12
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 11
- 239000004472 Lysine Substances 0.000 claims description 11
- 235000001014 amino acid Nutrition 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 10
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 10
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 229960003104 ornithine Drugs 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 150000004982 aromatic amines Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 150000003335 secondary amines Chemical class 0.000 claims description 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- 150000001413 amino acids Chemical class 0.000 claims description 8
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 8
- 239000012535 impurity Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000003141 primary amines Chemical class 0.000 claims description 7
- JYZJYKOZGGEXSX-UHFFFAOYSA-N 2-hydroxymyristic acid Chemical compound CCCCCCCCCCCCC(O)C(O)=O JYZJYKOZGGEXSX-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical class CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 6
- 235000018977 lysine Nutrition 0.000 claims description 6
- AVBJHQDHVYGQLS-AWEZNQCLSA-N (2s)-2-(dodecanoylamino)pentanedioic acid Chemical compound CCCCCCCCCCCC(=O)N[C@H](C(O)=O)CCC(O)=O AVBJHQDHVYGQLS-AWEZNQCLSA-N 0.000 claims description 5
- SIPMISGYHBUSIB-QFIPXVFZSA-N N-Stearoyl valine Chemical compound CCCCCCCCCCCCCCCCCC(=O)N[C@@H](C(C)C)C(O)=O SIPMISGYHBUSIB-QFIPXVFZSA-N 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 239000007859 condensation product Substances 0.000 claims description 5
- 239000012530 fluid Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 150000005846 sugar alcohols Polymers 0.000 claims description 5
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 4
- WQHXCNGQDLRDMP-INIZCTEOSA-N (2s)-2-(dodecanoylamino)-3-methylbutanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@@H](C(C)C)C(O)=O WQHXCNGQDLRDMP-INIZCTEOSA-N 0.000 claims description 4
- UYTOHYBIBPDOKX-ZDUSSCGKSA-N (2s)-2-(dodecanoylamino)propanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@@H](C)C(O)=O UYTOHYBIBPDOKX-ZDUSSCGKSA-N 0.000 claims description 4
- ZYJZBFYRVKLOAA-KRWDZBQOSA-N (2s)-2-(hexadecanoylamino)butanedioic acid Chemical compound CCCCCCCCCCCCCCCC(=O)N[C@H](C(O)=O)CC(O)=O ZYJZBFYRVKLOAA-KRWDZBQOSA-N 0.000 claims description 4
- XWECHXDFKBPXQY-IBGZPJMESA-N (2s)-2-(octadecanoylamino)butanedioic acid Chemical compound CCCCCCCCCCCCCCCCCC(=O)N[C@H](C(O)=O)CC(O)=O XWECHXDFKBPXQY-IBGZPJMESA-N 0.000 claims description 4
- JCQLZKNHLVROBO-JTQLQIEISA-N (2s)-2-(octanoylamino)pentanedioic acid Chemical compound CCCCCCCC(=O)N[C@H](C(O)=O)CCC(O)=O JCQLZKNHLVROBO-JTQLQIEISA-N 0.000 claims description 4
- XDOBXTLSTUFRRP-HNNXBMFYSA-N (2s)-2-(tetradecanoylamino)propanoic acid Chemical compound CCCCCCCCCCCCCC(=O)N[C@@H](C)C(O)=O XDOBXTLSTUFRRP-HNNXBMFYSA-N 0.000 claims description 4
- CLXADVHCSCRADU-KRWDZBQOSA-N (2s)-4-methylsulfanyl-2-(tetradecanoylamino)butanoic acid Chemical compound CCCCCCCCCCCCCC(=O)N[C@H](C(O)=O)CCSC CLXADVHCSCRADU-KRWDZBQOSA-N 0.000 claims description 4
- RKQUHHNIJVGMIG-UHFFFAOYSA-N 2-(dodecanoylamino)-3-phenylpropanoic acid Chemical compound CCCCCCCCCCCC(=O)NC(C(O)=O)CC1=CC=CC=C1 RKQUHHNIJVGMIG-UHFFFAOYSA-N 0.000 claims description 4
- VCRXMSMANOGRCM-UHFFFAOYSA-N 2-(dodecanoylamino)butanedioic acid Chemical compound CCCCCCCCCCCC(=O)NC(C(O)=O)CC(O)=O VCRXMSMANOGRCM-UHFFFAOYSA-N 0.000 claims description 4
- YDZIJQXINJLRLL-UHFFFAOYSA-N 2-hydroxydodecanoic acid Chemical compound CCCCCCCCCCC(O)C(O)=O YDZIJQXINJLRLL-UHFFFAOYSA-N 0.000 claims description 4
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-hydroxyoctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 claims description 4
- PNOPPKWUFKUHSX-UHFFFAOYSA-N 3-hydroxy-2-(tetradecanoylamino)propanoic acid Chemical compound CCCCCCCCCCCCCC(=O)NC(CO)C(O)=O PNOPPKWUFKUHSX-UHFFFAOYSA-N 0.000 claims description 4
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims description 4
- 239000004475 Arginine Substances 0.000 claims description 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004471 Glycine Substances 0.000 claims description 4
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 4
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 4
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 4
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 4
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 4
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 4
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 4
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 4
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 4
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 4
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 4
- UEWVQOCQZFYTBW-FQEVSTJZSA-N N-Palmitoyl leucine Chemical compound CCCCCCCCCCCCCCCC(=O)N[C@H](C(O)=O)CC(C)C UEWVQOCQZFYTBW-FQEVSTJZSA-N 0.000 claims description 4
- OGLNTVZUARMGNY-FQEVSTJZSA-N N-Palmitoyl valine Chemical compound CCCCCCCCCCCCCCCC(=O)N[C@@H](C(C)C)C(O)=O OGLNTVZUARMGNY-FQEVSTJZSA-N 0.000 claims description 4
- PHZQULSGYVCYNC-VWLOTQADSA-N N-Stearoyl phenylalanine Chemical compound CCCCCCCCCCCCCCCCCC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 PHZQULSGYVCYNC-VWLOTQADSA-N 0.000 claims description 4
- CLHUCXCVFSEJRR-IBGZPJMESA-N N-Stearoyl serine Chemical compound CCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)C(O)=O CLHUCXCVFSEJRR-IBGZPJMESA-N 0.000 claims description 4
- 235000021314 Palmitic acid Nutrition 0.000 claims description 4
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 4
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims description 4
- 239000004473 Threonine Substances 0.000 claims description 4
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 4
- 229960002684 aminocaproic acid Drugs 0.000 claims description 4
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 4
- 235000003704 aspartic acid Nutrition 0.000 claims description 4
- 229940000635 beta-alanine Drugs 0.000 claims description 4
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 4
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 claims description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 4
- 235000013922 glutamic acid Nutrition 0.000 claims description 4
- 239000004220 glutamic acid Substances 0.000 claims description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 4
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 4
- 229930182817 methionine Natural products 0.000 claims description 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 4
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 238000002203 pretreatment Methods 0.000 claims description 4
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004474 valine Substances 0.000 claims description 4
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 claims description 3
- JGHSBPIZNUXPLA-UHFFFAOYSA-N 2-hydroxyhexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(O)C(O)=O JGHSBPIZNUXPLA-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 claims description 3
- 229940063655 aluminum stearate Drugs 0.000 claims description 3
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 3
- WXLGETGSPUTYNT-UHFFFAOYSA-N n-butyl-12-hydroxyoctadecanamide Chemical group CCCCCCC(O)CCCCCCCCCCC(=O)NCCCC WXLGETGSPUTYNT-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- FMZUHGYZWYNSOA-VVBFYGJXSA-N (1r)-1-[(4r,4ar,8as)-2,6-diphenyl-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl]ethane-1,2-diol Chemical group C([C@@H]1OC(O[C@@H]([C@@H]1O1)[C@H](O)CO)C=2C=CC=CC=2)OC1C1=CC=CC=C1 FMZUHGYZWYNSOA-VVBFYGJXSA-N 0.000 claims description 2
- YVGLHNLETGOHCA-PMERELPUSA-N (4s)-5-(dioctylamino)-4-(dodecanoylamino)-5-oxopentanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@@H](CCC(O)=O)C(=O)N(CCCCCCCC)CCCCCCCC YVGLHNLETGOHCA-PMERELPUSA-N 0.000 claims description 2
- QISWVRFBORWSEN-UHFFFAOYSA-N 12-hydroxy-N-octyloctadecanamide Chemical compound C(CCCCCCC)NC(CCCCCCCCCCC(CCCCCC)O)=O QISWVRFBORWSEN-UHFFFAOYSA-N 0.000 claims description 2
- IPNCVYSFLZZUIP-NTISSMGPSA-N C(CCC)(=O)N.C(CCCCCCCCCCC)(=O)N[C@@H](C(C)C)C(=O)O Chemical compound C(CCC)(=O)N.C(CCCCCCCCCCC)(=O)N[C@@H](C(C)C)C(=O)O IPNCVYSFLZZUIP-NTISSMGPSA-N 0.000 claims description 2
- CPZGZCUYIZKLLW-UHFFFAOYSA-N CCCCCCCCCCCCCCN.CCCCCCCCCCCCCCCCCC(O)=O Chemical compound CCCCCCCCCCCCCCN.CCCCCCCCCCCCCCCCCC(O)=O CPZGZCUYIZKLLW-UHFFFAOYSA-N 0.000 claims description 2
- XKQHEYNSCLAFNH-UHFFFAOYSA-N CCCCCC[NH3+].CCCCCCCCCCCCCCCCCC([O-])=O Chemical compound CCCCCC[NH3+].CCCCCCCCCCCCCCCCCC([O-])=O XKQHEYNSCLAFNH-UHFFFAOYSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- 239000005639 Lauric acid Substances 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- ROADCTMRUVIXLV-UHFFFAOYSA-K aluminum;12-hydroxyoctadecanoate Chemical compound [Al+3].CCCCCCC(O)CCCCCCCCCCC([O-])=O.CCCCCCC(O)CCCCCCCCCCC([O-])=O.CCCCCCC(O)CCCCCCCCCCC([O-])=O ROADCTMRUVIXLV-UHFFFAOYSA-K 0.000 claims description 2
- 235000015278 beef Nutrition 0.000 claims description 2
- RXPKHKBYUIHIGL-UHFFFAOYSA-L calcium;12-hydroxyoctadecanoate Chemical compound [Ca+2].CCCCCCC(O)CCCCCCCCCCC([O-])=O.CCCCCCC(O)CCCCCCCCCCC([O-])=O RXPKHKBYUIHIGL-UHFFFAOYSA-L 0.000 claims description 2
- HRBZRZSCMANEHQ-UHFFFAOYSA-L calcium;hexadecanoate Chemical compound [Ca+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O HRBZRZSCMANEHQ-UHFFFAOYSA-L 0.000 claims description 2
- 229960000541 cetyl alcohol Drugs 0.000 claims description 2
- 229940087101 dibenzylidene sorbitol Drugs 0.000 claims description 2
- ZHOZSFBYLLOWOP-UHFFFAOYSA-N dodecan-1-amine;hexadecanoic acid Chemical group CCCCCCCCCCCCN.CCCCCCCCCCCCCCCC(O)=O ZHOZSFBYLLOWOP-UHFFFAOYSA-N 0.000 claims description 2
- FLJAJLOHHVNRHU-UHFFFAOYSA-K dodecanoate;iron(3+) Chemical compound [Fe+3].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O FLJAJLOHHVNRHU-UHFFFAOYSA-K 0.000 claims description 2
- ODAZTBLTCXOAGO-UHFFFAOYSA-N dodecanoate;octylazanium Chemical compound CCCCCCCCN.CCCCCCCCCCCC(O)=O ODAZTBLTCXOAGO-UHFFFAOYSA-N 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 229940116335 lauramide Drugs 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 229940063002 magnesium palmitate Drugs 0.000 claims description 2
- 235000019359 magnesium stearate Nutrition 0.000 claims description 2
- ABSWXCXMXIZDSN-UHFFFAOYSA-L magnesium;hexadecanoate Chemical compound [Mg+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O ABSWXCXMXIZDSN-UHFFFAOYSA-L 0.000 claims description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 2
- 229940043348 myristyl alcohol Drugs 0.000 claims description 2
- GISPPWDLKMGGSY-UHFFFAOYSA-N n-butylhexadecanamide Chemical compound CCCCCCCCCCCCCCCC(=O)NCCCC GISPPWDLKMGGSY-UHFFFAOYSA-N 0.000 claims description 2
- OHOPIZUOANPWQS-UHFFFAOYSA-N n-butyloctadecanamide Chemical group CCCCCCCCCCCCCCCCCC(=O)NCCCC OHOPIZUOANPWQS-UHFFFAOYSA-N 0.000 claims description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims description 2
- ULTFKCDPRAWOOU-UHFFFAOYSA-N n-octadecyldecanamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)CCCCCCCCC ULTFKCDPRAWOOU-UHFFFAOYSA-N 0.000 claims description 2
- NBEJBMSIQHPHDT-UHFFFAOYSA-N n-octyldodecanamide Chemical compound CCCCCCCCCCCC(=O)NCCCCCCCC NBEJBMSIQHPHDT-UHFFFAOYSA-N 0.000 claims description 2
- GKPRDEDBUSFKBH-UHFFFAOYSA-N octadecan-1-amine;octanoic acid Chemical compound CCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCCN GKPRDEDBUSFKBH-UHFFFAOYSA-N 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000600 sorbitol Substances 0.000 claims description 2
- 239000008117 stearic acid Substances 0.000 claims description 2
- 239000003760 tallow Substances 0.000 claims description 2
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 2
- 239000000811 xylitol Substances 0.000 claims description 2
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 2
- 229960002675 xylitol Drugs 0.000 claims description 2
- 235000010447 xylitol Nutrition 0.000 claims description 2
- PKGIJUSIJXTQFL-QFIPXVFZSA-N (4s)-5-(dibutylamino)-4-(dodecanoylamino)-5-oxopentanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@@H](CCC(O)=O)C(=O)N(CCCC)CCCC PKGIJUSIJXTQFL-QFIPXVFZSA-N 0.000 claims 1
- 229940114072 12-hydroxystearic acid Drugs 0.000 claims 1
- 229960003121 arginine Drugs 0.000 claims 1
- 230000001112 coagulating effect Effects 0.000 claims 1
- GMGONJRHVPHAPD-UCLFVTEUSA-H dialuminum;(2s)-2-(dodecanoylamino)pentanedioate Chemical compound [Al+3].[Al+3].CCCCCCCCCCCC(=O)N[C@H](C([O-])=O)CCC([O-])=O.CCCCCCCCCCCC(=O)N[C@H](C([O-])=O)CCC([O-])=O.CCCCCCCCCCCC(=O)N[C@H](C([O-])=O)CCC([O-])=O GMGONJRHVPHAPD-UCLFVTEUSA-H 0.000 claims 1
- 229960002885 histidine Drugs 0.000 claims 1
- 235000019198 oils Nutrition 0.000 description 137
- 239000003795 chemical substances by application Substances 0.000 description 14
- 239000010779 crude oil Substances 0.000 description 14
- 238000012545 processing Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 239000010730 cutting oil Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000010687 lubricating oil Substances 0.000 description 5
- 238000000691 measurement method Methods 0.000 description 5
- 239000000693 micelle Substances 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 239000007769 metal material Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- 238000007112 amidation reaction Methods 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
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- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([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 3
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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 3
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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 3
- 239000004094 surface-active agent Substances 0.000 description 3
- WTHCRRXOPUNKAA-UHFFFAOYSA-N 16-methylheptadecan-1-amine Chemical compound CC(C)CCCCCCCCCCCCCCCN WTHCRRXOPUNKAA-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000002173 cutting fluid Substances 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000003311 flocculating effect Effects 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005491 wire drawing Methods 0.000 description 2
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical class CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- NIDRASOKXCQPKX-DFWYDOINSA-L calcium;(2s)-2-aminopentanedioate Chemical compound [Ca+2].[O-]C(=O)[C@@H](N)CCC([O-])=O NIDRASOKXCQPKX-DFWYDOINSA-L 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- HWGUOODPQIXVKG-UHFFFAOYSA-N dodecan-1-amine;octadecanoic acid Chemical compound CCCCCCCCCCCC[NH3+].CCCCCCCCCCCCCCCCCC([O-])=O HWGUOODPQIXVKG-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229940071085 lauroyl glutamate Drugs 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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
- 239000002245 particle Substances 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 238000007781 pre-processing Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007430 reference method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Landscapes
- Sampling And Sample Adjustment (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14935178A JPS5575633A (en) | 1978-12-01 | 1978-12-01 | Preparatory processing method for concentration measurement for water-soluble metal machining oil agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14935178A JPS5575633A (en) | 1978-12-01 | 1978-12-01 | Preparatory processing method for concentration measurement for water-soluble metal machining oil agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5575633A JPS5575633A (en) | 1980-06-07 |
| JPS6129761B2 true JPS6129761B2 (uk) | 1986-07-09 |
Family
ID=15473215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14935178A Granted JPS5575633A (en) | 1978-12-01 | 1978-12-01 | Preparatory processing method for concentration measurement for water-soluble metal machining oil agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5575633A (uk) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0263873U (uk) * | 1988-10-31 | 1990-05-14 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100286008A1 (en) * | 2007-05-09 | 2010-11-11 | Kyowa Hakko Chemical Co., Ltd. | Additive for oils and lubricant containing the same |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS499484A (uk) * | 1972-05-27 | 1974-01-28 | ||
| JPS49135269A (uk) * | 1973-05-04 | 1974-12-26 |
-
1978
- 1978-12-01 JP JP14935178A patent/JPS5575633A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS499484A (uk) * | 1972-05-27 | 1974-01-28 | ||
| JPS49135269A (uk) * | 1973-05-04 | 1974-12-26 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0263873U (uk) * | 1988-10-31 | 1990-05-14 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5575633A (en) | 1980-06-07 |
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