CA1049046A - Vinylidene alcohol compositions - Google Patents
Vinylidene alcohol compositionsInfo
- Publication number
- CA1049046A CA1049046A CA73170589A CA170589A CA1049046A CA 1049046 A CA1049046 A CA 1049046A CA 73170589 A CA73170589 A CA 73170589A CA 170589 A CA170589 A CA 170589A CA 1049046 A CA1049046 A CA 1049046A
- Authority
- CA
- Canada
- Prior art keywords
- vinylidene
- range
- alcohols
- integer
- alcohol
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 138
- -1 Vinylidene alcohol Chemical compound 0.000 title claims abstract description 120
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 150000003138 primary alcohols Chemical class 0.000 claims description 18
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 abstract description 67
- 239000004094 surface-active agent Substances 0.000 abstract description 38
- 238000009736 wetting Methods 0.000 abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 19
- 230000002195 synergetic effect Effects 0.000 abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 83
- 235000013350 formula milk Nutrition 0.000 description 41
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 33
- 238000000034 method Methods 0.000 description 31
- 239000003054 catalyst Substances 0.000 description 24
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 20
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 18
- 229910017052 cobalt Inorganic materials 0.000 description 17
- 239000010941 cobalt Substances 0.000 description 17
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000007037 hydroformylation reaction Methods 0.000 description 12
- 150000001336 alkenes Chemical class 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229960004279 formaldehyde Drugs 0.000 description 10
- 235000019256 formaldehyde Nutrition 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 8
- 229910002091 carbon monoxide Inorganic materials 0.000 description 8
- 239000004711 α-olefin Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical class C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000004435 Oxo alcohol Substances 0.000 description 5
- 229930040373 Paraformaldehyde Natural products 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229960005419 nitrogen Drugs 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- XRBURMNBUVEAKD-UHFFFAOYSA-N chromium copper nickel Chemical compound [Cr].[Ni].[Cu] XRBURMNBUVEAKD-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229940093470 ethylene Drugs 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000003333 secondary alcohols Chemical class 0.000 description 4
- 239000010865 sewage Substances 0.000 description 4
- MEUHELKJCGXSBF-UHFFFAOYSA-N 5-methylideneundecane Chemical compound CCCCCCC(=C)CCCC MEUHELKJCGXSBF-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 125000006353 oxyethylene group Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 2
- ICTOQBVCUDARKR-UHFFFAOYSA-N 3-butylnonan-1-ol Chemical compound CCCCCCC(CCO)CCCC ICTOQBVCUDARKR-UHFFFAOYSA-N 0.000 description 2
- XZJZVNABSFJYOK-UHFFFAOYSA-N 3-methylidenenonane Chemical compound CCCCCCC(=C)CC XZJZVNABSFJYOK-UHFFFAOYSA-N 0.000 description 2
- SEFXBCYTMUNYFC-UHFFFAOYSA-N 5-methylidenenonane Chemical compound CCCCC(=C)CCCC SEFXBCYTMUNYFC-UHFFFAOYSA-N 0.000 description 2
- RMTSLZJISCPGBT-UHFFFAOYSA-N 5-methylidenetridecane Chemical compound CCCCCCCCC(=C)CCCC RMTSLZJISCPGBT-UHFFFAOYSA-N 0.000 description 2
- XGXGKWMBNLXJOI-UHFFFAOYSA-N 7-methylideneheptadecane Chemical compound CCCCCCCCCCC(=C)CCCCCC XGXGKWMBNLXJOI-UHFFFAOYSA-N 0.000 description 2
- ALLHOOZJEFGTPW-UHFFFAOYSA-N 7-methylidenepentadecane Chemical compound CCCCCCCCC(=C)CCCCCC ALLHOOZJEFGTPW-UHFFFAOYSA-N 0.000 description 2
- QDOYJBSJTHIWKH-UHFFFAOYSA-N 7-methylidenetridecane Chemical compound CCCCCCC(=C)CCCCCC QDOYJBSJTHIWKH-UHFFFAOYSA-N 0.000 description 2
- WSUZLUMBCPVHKX-UHFFFAOYSA-N 9-methylideneheptadecane Chemical compound CCCCCCCCC(=C)CCCCCCCC WSUZLUMBCPVHKX-UHFFFAOYSA-N 0.000 description 2
- NEAFLGWVOVUKRO-UHFFFAOYSA-N 9-methylidenenonadecane Chemical compound CCCCCCCCCCC(=C)CCCCCCCC NEAFLGWVOVUKRO-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- REIUXOLGHVXAEO-UHFFFAOYSA-N pentadecan-1-ol Chemical compound CCCCCCCCCCCCCCCO REIUXOLGHVXAEO-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 229940087291 tridecyl alcohol Drugs 0.000 description 2
- OOZBTDPWFHJVEK-UHFFFAOYSA-N tris(2-nonylphenyl) phosphate Chemical compound CCCCCCCCCC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC OOZBTDPWFHJVEK-UHFFFAOYSA-N 0.000 description 2
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- FOEPUSOAVBJQMF-UHFFFAOYSA-N 3-butylhept-3-en-1-ol Chemical compound CCCCC(CCO)=CCCC FOEPUSOAVBJQMF-UHFFFAOYSA-N 0.000 description 1
- JVZDVHQHXNGWRQ-UHFFFAOYSA-N 3-butylheptan-1-ol Chemical compound CCCCC(CCO)CCCC JVZDVHQHXNGWRQ-UHFFFAOYSA-N 0.000 description 1
- VHSZFRCHZPYBRR-UHFFFAOYSA-N 3-butylideneundecan-1-ol Chemical compound CCCCCCCCC(CCO)=CCCC VHSZFRCHZPYBRR-UHFFFAOYSA-N 0.000 description 1
- SMLCBLWLCMLEGQ-UHFFFAOYSA-N 3-butylnon-3-en-1-ol Chemical compound CCCCCC=C(CCO)CCCC SMLCBLWLCMLEGQ-UHFFFAOYSA-N 0.000 description 1
- MTLPJVNDUUSBCR-UHFFFAOYSA-N 3-butylundec-3-en-1-ol Chemical compound CCCCCCCC=C(CCO)CCCC MTLPJVNDUUSBCR-UHFFFAOYSA-N 0.000 description 1
- VMLWZTNSQDTBRE-UHFFFAOYSA-N 3-butylundecan-1-ol Chemical compound CCCCCCCCC(CCO)CCCC VMLWZTNSQDTBRE-UHFFFAOYSA-N 0.000 description 1
- DTCFZDHOKKJHSN-UHFFFAOYSA-N 3-ethylidenenonan-1-ol Chemical compound CCCCCCC(=CC)CCO DTCFZDHOKKJHSN-UHFFFAOYSA-N 0.000 description 1
- PMXHOXHCIWJUBQ-UHFFFAOYSA-N 3-ethylnon-3-en-1-ol Chemical compound CCCCCC=C(CC)CCO PMXHOXHCIWJUBQ-UHFFFAOYSA-N 0.000 description 1
- QTJURDURBMIUFX-UHFFFAOYSA-N 3-ethylnonan-1-ol Chemical compound CCCCCCC(CC)CCO QTJURDURBMIUFX-UHFFFAOYSA-N 0.000 description 1
- JRCWSSFGFOJRCV-UHFFFAOYSA-N 3-hexylidenetridecan-1-ol Chemical compound CCCCCCCCCCC(CCO)=CCCCCC JRCWSSFGFOJRCV-UHFFFAOYSA-N 0.000 description 1
- VSIPOOCYARPLRK-UHFFFAOYSA-N 3-hexylideneundecan-1-ol Chemical compound CCCCCCCCC(CCO)=CCCCCC VSIPOOCYARPLRK-UHFFFAOYSA-N 0.000 description 1
- RFHHLESTVBMLKX-UHFFFAOYSA-N 3-hexylnon-3-en-1-ol Chemical compound CCCCCCC(CCO)=CCCCCC RFHHLESTVBMLKX-UHFFFAOYSA-N 0.000 description 1
- VUXOZPGHRNYEFX-UHFFFAOYSA-N 3-hexylnonan-1-ol Chemical compound CCCCCCC(CCO)CCCCCC VUXOZPGHRNYEFX-UHFFFAOYSA-N 0.000 description 1
- WUFIXFRQYMQBPX-UHFFFAOYSA-N 3-hexyltridec-3-en-1-ol Chemical compound CCCCCCCCCC=C(CCO)CCCCCC WUFIXFRQYMQBPX-UHFFFAOYSA-N 0.000 description 1
- DQAVXBYHGUFYEA-UHFFFAOYSA-N 3-hexyltridecan-1-ol Chemical compound CCCCCCCCCCC(CCO)CCCCCC DQAVXBYHGUFYEA-UHFFFAOYSA-N 0.000 description 1
- HLKOQCCBCXFDMM-UHFFFAOYSA-N 3-hexylundec-3-en-1-ol Chemical compound CCCCCCCC=C(CCO)CCCCCC HLKOQCCBCXFDMM-UHFFFAOYSA-N 0.000 description 1
- WGDHJACBNBATDD-UHFFFAOYSA-N 3-hexylundecan-1-ol Chemical compound CCCCCCCCC(CCO)CCCCCC WGDHJACBNBATDD-UHFFFAOYSA-N 0.000 description 1
- XGZQFQBTSAQPKG-UHFFFAOYSA-N 3-octylundec-3-en-1-ol Chemical compound CCCCCCCCC(CCO)=CCCCCCCC XGZQFQBTSAQPKG-UHFFFAOYSA-N 0.000 description 1
- DDSFVTGXVOEBNX-UHFFFAOYSA-N 3-octylundecan-1-ol Chemical compound CCCCCCCCC(CCO)CCCCCCCC DDSFVTGXVOEBNX-UHFFFAOYSA-N 0.000 description 1
- FZWJUHDIYQWSPE-UHFFFAOYSA-N 3-pentyloct-3-en-1-ol Chemical compound CCCCCC(CCO)=CCCCC FZWJUHDIYQWSPE-UHFFFAOYSA-N 0.000 description 1
- 102100038916 Caspase-5 Human genes 0.000 description 1
- 241000004297 Draba Species 0.000 description 1
- 101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 1
- 101100273286 Mus musculus Casp4 gene Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
- 229910020667 PBr3 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 238000009835 boiling Methods 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
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000447 dimerizing effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- ZEQFUZSHIZUQTP-UHFFFAOYSA-K heptanoate rhodium(3+) Chemical compound C(CCCCCC)(=O)[O-].[Rh+3].C(CCCCCC)(=O)[O-].C(CCCCCC)(=O)[O-] ZEQFUZSHIZUQTP-UHFFFAOYSA-K 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 235000007686 potassium Nutrition 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000015227 regulation of liquid surface tension Effects 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US260545A US3887624A (en) | 1972-06-07 | 1972-06-07 | Vinylidene alcohol compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1049046A true CA1049046A (en) | 1979-02-20 |
Family
ID=22989598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA73170589A Expired CA1049046A (en) | 1972-06-07 | 1973-05-07 | Vinylidene alcohol compositions |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5136244B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1049046A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0944699A2 (en) * | 1996-11-26 | 1999-09-29 | The Procter & Gamble Company | Polyoxyalkylene surfactants |
| JP2005298443A (ja) * | 2004-04-15 | 2005-10-27 | Idemitsu Kosan Co Ltd | 長鎖分岐アルコールとその製造方法 |
-
1973
- 1973-05-07 CA CA73170589A patent/CA1049046A/en not_active Expired
- 1973-06-07 JP JP6430873A patent/JPS5136244B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5136244B2 (enrdf_load_stackoverflow) | 1976-10-07 |
| JPS4954308A (enrdf_load_stackoverflow) | 1974-05-27 |
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