CA2226550C - Concentrated, stable fabric softening compositions including chelants - Google Patents

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Publication number

CA2226550C

CA2226550C CA002226550A CA2226550A CA2226550C CA 2226550 C CA2226550 C CA 2226550C CA 002226550 A CA002226550 A CA 002226550A CA 2226550 A CA2226550 A CA 2226550A CA 2226550 C CA2226550 C CA 2226550C

Authority

CA

Canada

Prior art keywords

methyl

dimethyl

hexanediol

pentanediol

diol

Prior art date

1995-07-11

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• 239000000203 mixture Substances 0.000 title claims abstract description 273
• 239000004744 fabric Substances 0.000 title claims abstract description 47
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 44
• 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 39
• 239000000194 fatty acid Substances 0.000 claims abstract description 39
• 229930195729 fatty acid Natural products 0.000 claims abstract description 39
• 150000004665 fatty acids Chemical class 0.000 claims abstract description 39
• 239000002253 acid Substances 0.000 claims abstract description 38
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 25
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 16
• 229910052740 iodine Inorganic materials 0.000 claims abstract description 16
• 239000011630 iodine Substances 0.000 claims abstract description 16
• 125000001424 substituent group Chemical group 0.000 claims abstract description 16
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
• 239000001257 hydrogen Substances 0.000 claims abstract description 13
• 238000004458 analytical method Methods 0.000 claims abstract description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 11
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 8
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims abstract description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
• 239000002904 solvent Substances 0.000 claims description 211
• YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 136
• 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 135
• DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 132
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 66
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 61
• 229910001868 water Inorganic materials 0.000 claims description 59
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
• 239000002979 fabric softener Substances 0.000 claims description 39
• 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 32
• 150000001875 compounds Chemical class 0.000 claims description 31
• 239000000463 material Substances 0.000 claims description 29
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
• QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 claims description 18
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 14
• 239000013522 chelant Substances 0.000 claims description 11
• 239000003021 water soluble solvent Substances 0.000 claims description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 229910002651 NO3 Inorganic materials 0.000 claims description 9
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 9
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 8
• KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 claims description 8
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 8
• JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 8
• 229960003330 pentetic acid Drugs 0.000 claims description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 6
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 5
• MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims description 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 3
• 229960001484 edetic acid Drugs 0.000 claims 2
• YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 claims 2
• -1 e.g. Chemical group 0.000 abstract description 102
• 239000002738 chelating agent Substances 0.000 abstract description 25
• 230000005540 biological transmission Effects 0.000 abstract description 7
• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 217
• 238000000034 method Methods 0.000 description 210
• WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 170
• UNVGBIALRHLALK-UHFFFAOYSA-N 1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 description 132
• AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 description 96
• GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 description 95
• RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 92
• PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 76
• QVTWBMUAJHVAIJ-UHFFFAOYSA-N hexane-1,4-diol Chemical compound CCC(O)CCCO QVTWBMUAJHVAIJ-UHFFFAOYSA-N 0.000 description 73
• 150000002009 diols Chemical class 0.000 description 69
• ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 65
• OGRCRHSHBFQRKO-UHFFFAOYSA-N heptane-1,4-diol Chemical compound CCCC(O)CCCO OGRCRHSHBFQRKO-UHFFFAOYSA-N 0.000 description 64
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 61
• TXGJTWACJNYNOJ-UHFFFAOYSA-N hexane-2,4-diol Chemical compound CCC(O)CC(C)O TXGJTWACJNYNOJ-UHFFFAOYSA-N 0.000 description 61
• 235000013772 propylene glycol Nutrition 0.000 description 56
• 238000006243 chemical reaction Methods 0.000 description 47
• XLMFDCKSFJWJTP-UHFFFAOYSA-N pentane-2,3-diol Chemical compound CCC(O)C(C)O XLMFDCKSFJWJTP-UHFFFAOYSA-N 0.000 description 45
• BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 41
• ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 36
• XVEOUOTUJBYHNL-UHFFFAOYSA-N heptane-2,4-diol Chemical compound CCCC(O)CC(C)O XVEOUOTUJBYHNL-UHFFFAOYSA-N 0.000 description 36
• GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 description 36
• OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 35
• 229940083957 1,2-butanediol Drugs 0.000 description 34
• XTVHTJKQKUOEQA-UHFFFAOYSA-N heptane-2,5-diol Chemical compound CCC(O)CCC(C)O XTVHTJKQKUOEQA-UHFFFAOYSA-N 0.000 description 34
• HTXVEEVTGGCUNC-UHFFFAOYSA-N heptane-1,3-diol Chemical compound CCCCC(O)CCO HTXVEEVTGGCUNC-UHFFFAOYSA-N 0.000 description 30
• 238000002360 preparation method Methods 0.000 description 30
• 229940015975 1,2-hexanediol Drugs 0.000 description 29
• UQGLNXPQGUMNRU-UHFFFAOYSA-N heptane-1,6-diol Chemical compound CC(O)CCCCCO UQGLNXPQGUMNRU-UHFFFAOYSA-N 0.000 description 29
• FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 29
• WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 29
• NNYOSLMHXUVJJH-UHFFFAOYSA-N heptane-1,5-diol Chemical compound CCC(O)CCCCO NNYOSLMHXUVJJH-UHFFFAOYSA-N 0.000 description 28
• 239000000047 product Substances 0.000 description 28
• XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 27
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 26
• 239000011541 reaction mixture Substances 0.000 description 26
• 239000007788 liquid Substances 0.000 description 24
• 238000009833 condensation Methods 0.000 description 22
• 230000005494 condensation Effects 0.000 description 22
• OZIMXLFSRSPFAS-UHFFFAOYSA-N heptane-2,6-diol Chemical compound CC(O)CCCC(C)O OZIMXLFSRSPFAS-UHFFFAOYSA-N 0.000 description 22
• 229920006395 saturated elastomer Polymers 0.000 description 22
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 21
• BQWORYKVVNTRAW-UHFFFAOYSA-N heptane-3,5-diol Chemical compound CCC(O)CC(O)CC BQWORYKVVNTRAW-UHFFFAOYSA-N 0.000 description 20
• 239000000243 solution Substances 0.000 description 20
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
• AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
• 239000000126 substance Substances 0.000 description 17
• HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 17
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
• 150000001299 aldehydes Chemical class 0.000 description 16
• 125000003118 aryl group Chemical group 0.000 description 16
• 238000003756 stirring Methods 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 14
• WYNVIVRXHYGNRT-UHFFFAOYSA-N octane-3,5-diol Chemical compound CCCC(O)CC(O)CC WYNVIVRXHYGNRT-UHFFFAOYSA-N 0.000 description 14
• 230000002829 reductive effect Effects 0.000 description 14
• MZQZXSHFWDHNOW-UHFFFAOYSA-N 1-phenylpropane-1,2-diol Chemical compound CC(O)C(O)C1=CC=CC=C1 MZQZXSHFWDHNOW-UHFFFAOYSA-N 0.000 description 13
• JHWQMXKQJVAWKI-UHFFFAOYSA-N 3-phenylpropane-1,2-diol Chemical compound OCC(O)CC1=CC=CC=C1 JHWQMXKQJVAWKI-UHFFFAOYSA-N 0.000 description 13
• 229940123150 Chelating agent Drugs 0.000 description 13
• 238000010438 heat treatment Methods 0.000 description 13
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• QCIYAEYRVFUFAP-UHFFFAOYSA-N hexane-2,3-diol Chemical compound CCCC(O)C(C)O QCIYAEYRVFUFAP-UHFFFAOYSA-N 0.000 description 12
• 238000010992 reflux Methods 0.000 description 12
• RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 11
• 239000002585 base Substances 0.000 description 11
• 150000005690 diesters Chemical class 0.000 description 11
• 150000002170 ethers Chemical class 0.000 description 11
• 239000010410 layer Substances 0.000 description 11
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• 239000003795 chemical substances by application Substances 0.000 description 10
• 238000004821 distillation Methods 0.000 description 10
• 150000003839 salts Chemical class 0.000 description 10
• 150000007513 acids Chemical class 0.000 description 9
• 230000015572 biosynthetic process Effects 0.000 description 9
• 150000002081 enamines Chemical class 0.000 description 9
• POFSNPPXJUQANW-UHFFFAOYSA-N hexane-3,4-diol Chemical compound CCC(O)C(O)CC POFSNPPXJUQANW-UHFFFAOYSA-N 0.000 description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
• 238000003786 synthesis reaction Methods 0.000 description 9
• 238000005292 vacuum distillation Methods 0.000 description 9
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
• 229910052786 argon Inorganic materials 0.000 description 8
• BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 8
• 238000009472 formulation Methods 0.000 description 8
• SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 8
• 239000004615 ingredient Substances 0.000 description 8
• 235000019645 odor Nutrition 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• VKZRWSNIWNFCIQ-WDSKDSINSA-N (2s)-2-[2-[[(1s)-1,2-dicarboxyethyl]amino]ethylamino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NCCN[C@H](C(O)=O)CC(O)=O VKZRWSNIWNFCIQ-WDSKDSINSA-N 0.000 description 7
• LNCZPZFNQQFXPT-UHFFFAOYSA-N 2-phenyl-1,2-propanediol Chemical compound OCC(O)(C)C1=CC=CC=C1 LNCZPZFNQQFXPT-UHFFFAOYSA-N 0.000 description 7
• 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 7
• 150000001298 alcohols Chemical class 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 230000000052 comparative effect Effects 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 238000001914 filtration Methods 0.000 description 7
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 7
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
• 229910052708 sodium Inorganic materials 0.000 description 7
• 238000003860 storage Methods 0.000 description 7
• DCTMXCOHGKSXIZ-UHFFFAOYSA-N (R)-1,3-Octanediol Chemical compound CCCCCC(O)CCO DCTMXCOHGKSXIZ-UHFFFAOYSA-N 0.000 description 6
• 150000000185 1,3-diols Chemical class 0.000 description 6
• 150000000190 1,4-diols Chemical class 0.000 description 6
• JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
• 150000001728 carbonyl compounds Chemical class 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
• 238000006460 hydrolysis reaction Methods 0.000 description 6
• 230000000670 limiting effect Effects 0.000 description 6
• 229940098779 methanesulfonic acid Drugs 0.000 description 6
• CFVJOJZVNRYDDJ-UHFFFAOYSA-N oct-6-ene-3,5-diol Chemical compound CCC(O)CC(O)C=CC CFVJOJZVNRYDDJ-UHFFFAOYSA-N 0.000 description 6
• LWNYCVKZZKMXJZ-UHFFFAOYSA-N octa-2,5-diene-1,7-diol Chemical compound CC(O)C=CCC=CCO LWNYCVKZZKMXJZ-UHFFFAOYSA-N 0.000 description 6
• XFVAWWPVJMMDGC-UHFFFAOYSA-N octa-2,7-diene-1,6-diol Chemical compound OCC=CCCC(O)C=C XFVAWWPVJMMDGC-UHFFFAOYSA-N 0.000 description 6
• XOHPJWXAFXEPJQ-UHFFFAOYSA-N pent-4-ene-1,3-diol Chemical compound OCCC(O)C=C XOHPJWXAFXEPJQ-UHFFFAOYSA-N 0.000 description 6
• 239000002304 perfume Substances 0.000 description 6
• 238000000746 purification Methods 0.000 description 6
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
• 239000007787 solid Substances 0.000 description 6
• 239000007858 starting material Substances 0.000 description 6
• MZQZXSHFWDHNOW-IONNQARKSA-N (1S,2S)-1-phenyl-1,2-dihydroxypropane Natural products C[C@H](O)[C@@H](O)C1=CC=CC=C1 MZQZXSHFWDHNOW-IONNQARKSA-N 0.000 description 5
• PTCYLOJKSMVJTR-RMKNXTFCSA-N (2e)-3,7-dimethylocta-2,6-diene-1,4-diol Chemical compound CC(C)=CCC(O)C(\C)=C\CO PTCYLOJKSMVJTR-RMKNXTFCSA-N 0.000 description 5
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 5
• VKWZWOKLRQWMPC-UHFFFAOYSA-N 1-(2-hydroxybutoxy)butan-2-ol Chemical compound CCC(O)COCC(O)CC VKWZWOKLRQWMPC-UHFFFAOYSA-N 0.000 description 5
• PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 5
• OKWLUBCSBVYYTC-UHFFFAOYSA-N 1-phenylbutane-1,4-diol Chemical compound OCCCC(O)C1=CC=CC=C1 OKWLUBCSBVYYTC-UHFFFAOYSA-N 0.000 description 5
• ALVVFCGEWCJMES-UHFFFAOYSA-N 2-ethyl-3-methylpentane-1,3-diol Chemical compound CCC(CO)C(C)(O)CC ALVVFCGEWCJMES-UHFFFAOYSA-N 0.000 description 5
• SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 5
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• DOLAPPHNYLNDJM-UHFFFAOYSA-N octa-3,7-diene-2,6-diol Chemical compound CC(O)C=CCC(O)C=C DOLAPPHNYLNDJM-UHFFFAOYSA-N 0.000 description 1
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• SUGFEDFXNPOSRF-UHFFFAOYSA-N octa-4,7-diene-2,3-diol Chemical compound CC(O)C(O)C=CCC=C SUGFEDFXNPOSRF-UHFFFAOYSA-N 0.000 description 1
• IAOVDWDWNRCRCA-UHFFFAOYSA-N octa-4,7-diene-2,6-diol Chemical compound CC(O)CC=CC(O)C=C IAOVDWDWNRCRCA-UHFFFAOYSA-N 0.000 description 1
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