ES2214650T3 - Composiciones de alcohol primario altamente ramificado, y detergentes biodegradables preparados a partir de ellos. - Google Patents
Composiciones de alcohol primario altamente ramificado, y detergentes biodegradables preparados a partir de ellos.Info
- Publication number
- ES2214650T3 ES2214650T3 ES97952830T ES97952830T ES2214650T3 ES 2214650 T3 ES2214650 T3 ES 2214650T3 ES 97952830 T ES97952830 T ES 97952830T ES 97952830 T ES97952830 T ES 97952830T ES 2214650 T3 ES2214650 T3 ES 2214650T3
- Authority
- ES
- Spain
- Prior art keywords
- branched
- composition
- alcohol
- olefin
- primary 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 179
- 150000003138 primary alcohols Chemical class 0.000 title claims abstract description 75
- 239000003599 detergent Substances 0.000 title claims abstract description 51
- 239000003054 catalyst Substances 0.000 claims abstract description 94
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 91
- -1 ISOPROPYL Chemical class 0.000 claims abstract description 62
- 239000010457 zeolite Substances 0.000 claims abstract description 44
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 39
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 39
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006471 dimerization reaction Methods 0.000 claims abstract description 31
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 26
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims abstract description 10
- 239000013522 chelant Substances 0.000 claims abstract description 7
- 150000001336 alkenes Chemical class 0.000 claims description 217
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 135
- 238000000034 method Methods 0.000 claims description 108
- 230000008569 process Effects 0.000 claims description 59
- 239000002253 acid Substances 0.000 claims description 49
- 150000001298 alcohols Chemical class 0.000 claims description 49
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 229910021536 Zeolite Inorganic materials 0.000 claims description 29
- 239000004094 surface-active agent Substances 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 229910052759 nickel Inorganic materials 0.000 claims description 23
- 229910052751 metal Inorganic materials 0.000 claims description 22
- 239000002184 metal Substances 0.000 claims description 22
- 238000007037 hydroformylation reaction Methods 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 150000007513 acids Chemical class 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 14
- 229910001657 ferrierite group Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000004703 alkoxides Chemical class 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 102000004190 Enzymes Human genes 0.000 claims description 5
- 108090000790 Enzymes Proteins 0.000 claims description 5
- 239000012190 activator Substances 0.000 claims description 5
- 125000005234 alkyl aluminium group Chemical group 0.000 claims description 5
- 239000006260 foam Substances 0.000 claims description 5
- 239000003752 hydrotrope Substances 0.000 claims description 5
- 239000000344 soap Substances 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 238000004061 bleaching Methods 0.000 claims description 4
- 239000007844 bleaching agent Substances 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 239000002808 molecular sieve Substances 0.000 claims description 3
- 229920005646 polycarboxylate Polymers 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 150000001860 citric acid derivatives Chemical class 0.000 claims description 2
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical class OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 2
- 239000002453 shampoo Substances 0.000 claims description 2
- 150000004760 silicates Chemical class 0.000 claims description 2
- 150000003890 succinate salts Chemical class 0.000 claims description 2
- 230000001180 sulfating effect Effects 0.000 claims description 2
- 150000008051 alkyl sulfates Chemical class 0.000 claims 4
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 159000000032 aromatic acids Chemical class 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 238000004851 dishwashing Methods 0.000 claims 1
- 229910001510 metal chloride Inorganic materials 0.000 claims 1
- 150000004967 organic peroxy acids Chemical class 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 45
- 238000004519 manufacturing process Methods 0.000 abstract description 21
- 229910052782 aluminium Inorganic materials 0.000 abstract description 15
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract description 11
- 150000004820 halides Chemical class 0.000 abstract description 6
- 150000007942 carboxylates Chemical class 0.000 abstract description 3
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 abstract 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 34
- 238000005481 NMR spectroscopy Methods 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 24
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 20
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000011230 binding agent Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 230000003647 oxidation Effects 0.000 description 11
- 238000007254 oxidation reaction Methods 0.000 description 11
- 229910000033 sodium borohydride Inorganic materials 0.000 description 11
- 239000012279 sodium borohydride Substances 0.000 description 11
- 239000004711 α-olefin Substances 0.000 description 11
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 10
- 239000003446 ligand Substances 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 238000006384 oligomerization reaction Methods 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 9
- 238000006065 biodegradation reaction Methods 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 150000002739 metals Chemical class 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 235000015165 citric acid Nutrition 0.000 description 8
- 239000000571 coke Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 7
- 230000036961 partial effect Effects 0.000 description 7
- 239000008188 pellet Substances 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 6
- 230000019635 sulfation Effects 0.000 description 6
- 238000005670 sulfation reaction Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000005755 formation reaction Methods 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 5
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 5
- 150000005673 monoalkenes Chemical class 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000003158 alcohol group Chemical group 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 4
- 238000001125 extrusion Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 3
- 229920003091 Methocel™ Polymers 0.000 description 3
- 239000004435 Oxo alcohol Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 238000007046 ethoxylation reaction Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- 230000000670 limiting effect Effects 0.000 description 3
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 3
- 150000003003 phosphines Chemical class 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000700 radioactive tracer Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 3
- BCAUVGPOEXLTJD-UHFFFAOYSA-N (2-cyclohexyl-4,6-dinitrophenyl) acetate Chemical compound C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(OC(=O)C)=C1C1CCCCC1 BCAUVGPOEXLTJD-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- SYLMLKKURPTCSO-UHFFFAOYSA-N 1-phosphanylethylphosphane Chemical compound CC(P)P SYLMLKKURPTCSO-UHFFFAOYSA-N 0.000 description 2
- KCYVXJFCVWQVRN-UHFFFAOYSA-L 2-ethylhexanoate;nickel(2+);2,2,2-trifluoroacetate Chemical compound [Ni+2].[O-]C(=O)C(F)(F)F.CCCCC(CC)C([O-])=O KCYVXJFCVWQVRN-UHFFFAOYSA-L 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 235000017060 Arachis glabrata Nutrition 0.000 description 2
- 241001553178 Arachis glabrata Species 0.000 description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 description 2
- 235000018262 Arachis monticola Nutrition 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- KRIOVPPHQSLHCZ-UHFFFAOYSA-N phenyl propionaldehyde Natural products CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
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- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
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- 239000001205 polyphosphate Substances 0.000 description 1
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- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
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- 229910052703 rhodium Inorganic materials 0.000 description 1
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- 238000002390 rotary evaporation Methods 0.000 description 1
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- 210000002374 sebum Anatomy 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
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- 229910052709 silver Inorganic materials 0.000 description 1
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- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- FRPJTGXMTIIFIT-UHFFFAOYSA-N tetraacetylethylenediamine Chemical compound CC(=O)C(N)(C(C)=O)C(N)(C(C)=O)C(C)=O FRPJTGXMTIIFIT-UHFFFAOYSA-N 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
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- 229910052723 transition metal Inorganic materials 0.000 description 1
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- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/10—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/06—Hydrogenosulfates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/10—Saturated ethers of polyhydroxy compounds
- C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/146—Sulfuric acid esters
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/29—Sulfates of polyoxyalkylene ethers
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US755843 | 1991-09-06 | ||
| US08/755,843 US5849960A (en) | 1996-11-26 | 1996-11-26 | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| US08/755,827 US5780694A (en) | 1996-11-26 | 1996-11-26 | Dimerized alcohol compositions and biodegradible surfactants made therefrom having cold water detergency |
| US755827 | 1996-11-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2214650T3 true ES2214650T3 (es) | 2004-09-16 |
Family
ID=27116135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES97952830T Expired - Lifetime ES2214650T3 (es) | 1996-11-26 | 1997-11-25 | Composiciones de alcohol primario altamente ramificado, y detergentes biodegradables preparados a partir de ellos. |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0958267B1 (enExample) |
| JP (1) | JP4118960B2 (enExample) |
| KR (1) | KR100641537B1 (enExample) |
| CN (1) | CN1090599C (enExample) |
| AU (1) | AU725968B2 (enExample) |
| BG (1) | BG64047B1 (enExample) |
| BR (1) | BR9713144B1 (enExample) |
| CA (1) | CA2271200C (enExample) |
| CZ (1) | CZ297436B6 (enExample) |
| DE (1) | DE69728429T2 (enExample) |
| ES (1) | ES2214650T3 (enExample) |
| NZ (1) | NZ334834A (enExample) |
| PL (1) | PL197319B1 (enExample) |
| PT (1) | PT958267E (enExample) |
| RO (1) | RO120404B1 (enExample) |
| RU (1) | RU2198159C2 (enExample) |
| SK (1) | SK285235B6 (enExample) |
| TR (1) | TR199901169T2 (enExample) |
| WO (1) | WO1998023566A1 (enExample) |
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| DK0898607T3 (da) * | 1996-04-16 | 2002-09-02 | Procter & Gamble | Væskeformige rensesammensætninger, der indeholder udvalgte midtkædeforgrenede, overfladeaktive midler |
| EG22088A (en) * | 1996-04-16 | 2002-07-31 | Procter & Gamble | Alkoxylated sulfates |
| PH11997056158B1 (en) * | 1996-04-16 | 2001-10-15 | Procter & Gamble | Mid-chain branched primary alkyl sulphates as surfactants |
| US6093856A (en) * | 1996-11-26 | 2000-07-25 | The Procter & Gamble Company | Polyoxyalkylene surfactants |
| ZA989155B (en) | 1997-10-10 | 1999-04-12 | Procter & Gamble | Mixed surfactant system |
| CN1281499A (zh) | 1997-10-14 | 2001-01-24 | 普罗格特-甘布尔公司 | 含有中链支链表面活性剂的颗粒洗涤剂组合物 |
| WO1999018928A1 (en) | 1997-10-14 | 1999-04-22 | The Procter & Gamble Company | Personal cleansing compositions comprising mid-chain branched surfactants |
| DE69828989T2 (de) | 1997-10-14 | 2006-03-30 | The Procter & Gamble Co., Cincinnati | Flüssige oder gelförmige spülmittelzusammensetzungen enthaltend in der mitte der kette verzweigte tenside |
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| DE19910370A1 (de) | 1999-03-09 | 2000-09-14 | Basf Ag | Verfahren zur Herstellung von Tensidalkoholen und Tensidalkoholethern, die hergestellten Produkte und ihre Verwendung |
| DE19912418A1 (de) | 1999-03-19 | 2000-09-21 | Basf Ag | Verfahren zur Herstellung von Tensidalkoholen und Tensidalkoholethern, die hergestellten Produkte und ihre Verwendung |
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| WO2003091190A1 (de) | 2002-04-26 | 2003-11-06 | Basf Aktiengesellschaft | Alkoxylatgemische und diese enthaltende waschmittel |
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| RU2247705C2 (ru) * | 2003-05-19 | 2005-03-10 | ГУ Институт нефтехимии и катализа Академии наук Республики Башкортостан и УНЦ РАН | Способ получения транс-3,4-диалкилциклопентан-1-олов |
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| GB798541A (en) | 1955-06-15 | 1958-07-23 | Ici Ltd | New primary alcohols |
| FR1151630A (fr) * | 1955-06-15 | 1958-02-03 | Ici Ltd | Nouveaux alcools saturés et leur procédé de fabrication |
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| GB8420945D0 (en) * | 1984-08-17 | 1984-09-19 | Unilever Plc | Detergents compositions |
| ATE66668T1 (de) * | 1986-07-01 | 1991-09-15 | Davy Mckee London | Verfahren zur herstellung von aldehyden durch hydroformylierung. |
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-
1997
- 1997-11-25 TR TR1999/01169T patent/TR199901169T2/xx unknown
- 1997-11-25 PL PL333503A patent/PL197319B1/pl not_active IP Right Cessation
- 1997-11-25 CN CN97199966A patent/CN1090599C/zh not_active Expired - Lifetime
- 1997-11-25 JP JP52430198A patent/JP4118960B2/ja not_active Expired - Lifetime
- 1997-11-25 KR KR1019997004593A patent/KR100641537B1/ko not_active Expired - Fee Related
- 1997-11-25 RO RO99-00592A patent/RO120404B1/ro unknown
- 1997-11-25 DE DE69728429T patent/DE69728429T2/de not_active Revoked
- 1997-11-25 CZ CZ0184899A patent/CZ297436B6/cs not_active IP Right Cessation
- 1997-11-25 EP EP97952830A patent/EP0958267B1/en not_active Revoked
- 1997-11-25 RU RU99113994/04A patent/RU2198159C2/ru active
- 1997-11-25 NZ NZ334834A patent/NZ334834A/xx unknown
- 1997-11-25 CA CA002271200A patent/CA2271200C/en not_active Expired - Lifetime
- 1997-11-25 AU AU56569/98A patent/AU725968B2/en not_active Ceased
- 1997-11-25 SK SK686-99A patent/SK285235B6/sk not_active IP Right Cessation
- 1997-11-25 WO PCT/EP1997/006694 patent/WO1998023566A1/en not_active Ceased
- 1997-11-25 PT PT97952830T patent/PT958267E/pt unknown
- 1997-11-25 BR BRPI9713144-0A patent/BR9713144B1/pt not_active IP Right Cessation
- 1997-11-25 ES ES97952830T patent/ES2214650T3/es not_active Expired - Lifetime
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1999
- 1999-05-28 BG BG103445A patent/BG64047B1/bg unknown
Also Published As
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|---|---|
| BG103445A (en) | 2000-05-31 |
| CZ184899A3 (cs) | 1999-11-17 |
| PL333503A1 (en) | 1999-12-20 |
| CA2271200C (en) | 2009-02-03 |
| BG64047B1 (bg) | 2003-11-28 |
| BR9713144B1 (pt) | 2009-01-13 |
| SK285235B6 (sk) | 2006-09-07 |
| WO1998023566A1 (en) | 1998-06-04 |
| AU5656998A (en) | 1998-06-22 |
| TR199901169T2 (xx) | 1999-08-23 |
| EP0958267B1 (en) | 2004-03-31 |
| DE69728429T2 (de) | 2005-03-03 |
| KR100641537B1 (ko) | 2006-10-31 |
| SK68699A3 (en) | 1999-11-08 |
| CA2271200A1 (en) | 1998-06-04 |
| AU725968B2 (en) | 2000-10-26 |
| PL197319B1 (pl) | 2008-03-31 |
| PT958267E (pt) | 2004-08-31 |
| EP0958267A1 (en) | 1999-11-24 |
| RO120404B1 (ro) | 2006-01-30 |
| JP4118960B2 (ja) | 2008-07-16 |
| CN1090599C (zh) | 2002-09-11 |
| RU2198159C2 (ru) | 2003-02-10 |
| CZ297436B6 (cs) | 2006-12-13 |
| KR20000069117A (ko) | 2000-11-25 |
| CN1238749A (zh) | 1999-12-15 |
| JP2001506597A (ja) | 2001-05-22 |
| DE69728429D1 (de) | 2004-05-06 |
| BR9713144A (pt) | 2000-02-08 |
| NZ334834A (en) | 2000-07-28 |
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