PL197319B1 - Kompozycja rozgałęzionych pierwszorzędowych alkoholi, sposób jej wytwarzania oraz kompozycja detergentowa - Google Patents
Kompozycja rozgałęzionych pierwszorzędowych alkoholi, sposób jej wytwarzania oraz kompozycja detergentowaInfo
- Publication number
- PL197319B1 PL197319B1 PL333503A PL33350397A PL197319B1 PL 197319 B1 PL197319 B1 PL 197319B1 PL 333503 A PL333503 A PL 333503A PL 33350397 A PL33350397 A PL 33350397A PL 197319 B1 PL197319 B1 PL 197319B1
- Authority
- PL
- Poland
- Prior art keywords
- branches
- branched
- alcohol
- olefins
- alcohols
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 163
- 150000003138 primary alcohols Chemical class 0.000 title claims abstract description 72
- 239000003599 detergent Substances 0.000 title claims abstract description 44
- 150000001298 alcohols Chemical class 0.000 title description 62
- 238000006065 biodegradation reaction Methods 0.000 title description 8
- 238000000034 method Methods 0.000 claims abstract description 112
- -1 alkoxylates Chemical class 0.000 claims abstract description 93
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 92
- 230000008569 process Effects 0.000 claims abstract description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 47
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 29
- 239000004094 surface-active agent Substances 0.000 claims abstract description 25
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 29
- 238000005406 washing Methods 0.000 claims description 22
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000007844 bleaching agent Substances 0.000 claims description 7
- 239000000344 soap Substances 0.000 claims description 7
- 239000012190 activator Substances 0.000 claims description 6
- 102000004190 Enzymes Human genes 0.000 claims description 5
- 108090000790 Enzymes Proteins 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 5
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 238000001514 detection method Methods 0.000 claims description 4
- 239000006260 foam Substances 0.000 claims description 4
- 229920005646 polycarboxylate Polymers 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 239000012459 cleaning agent Substances 0.000 claims description 3
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical class OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 150000004967 organic peroxy acids Chemical class 0.000 claims description 3
- 239000002453 shampoo Substances 0.000 claims description 3
- 150000004760 silicates Chemical class 0.000 claims description 3
- 159000000032 aromatic acids Chemical class 0.000 claims description 2
- 238000004061 bleaching Methods 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 150000001860 citric acid derivatives Chemical class 0.000 claims description 2
- 238000004851 dishwashing Methods 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
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims 2
- 241000254173 Coleoptera Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 235000012459 muffins Nutrition 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 abstract description 194
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 104
- 239000003054 catalyst Substances 0.000 abstract description 93
- 239000010457 zeolite Substances 0.000 abstract description 46
- 238000006243 chemical reaction Methods 0.000 abstract description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 42
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract description 39
- 238000006317 isomerization reaction Methods 0.000 abstract description 36
- 229910052759 nickel Inorganic materials 0.000 abstract description 21
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 17
- 238000007037 hydroformylation reaction Methods 0.000 abstract description 16
- 238000004519 manufacturing process Methods 0.000 abstract description 14
- 230000019635 sulfation Effects 0.000 abstract description 6
- 238000005670 sulfation reaction Methods 0.000 abstract description 6
- 239000013522 chelant Substances 0.000 abstract description 5
- 125000004429 atom Chemical group 0.000 abstract description 4
- 125000005234 alkyl aluminium group Chemical group 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 37
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 34
- 238000005481 NMR spectroscopy Methods 0.000 description 32
- 229910021536 Zeolite Inorganic materials 0.000 description 29
- 238000006471 dimerization reaction Methods 0.000 description 29
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 26
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 25
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000009835 boiling Methods 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 20
- 229910052751 metal Inorganic materials 0.000 description 17
- 239000002184 metal Substances 0.000 description 17
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 229910052782 aluminium Inorganic materials 0.000 description 14
- 229910001657 ferrierite group Inorganic materials 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 13
- 238000004821 distillation Methods 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- 239000004711 α-olefin Substances 0.000 description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- 238000002156 mixing Methods 0.000 description 12
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 11
- 239000011230 binding agent Substances 0.000 description 11
- 229910002091 carbon monoxide Inorganic materials 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 229910000033 sodium borohydride Inorganic materials 0.000 description 11
- 239000012279 sodium borohydride 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
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 10
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 238000006384 oligomerization reaction Methods 0.000 description 10
- 230000003647 oxidation Effects 0.000 description 10
- 238000007254 oxidation reaction Methods 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 239000000571 coke Substances 0.000 description 9
- 239000003446 ligand Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000005755 formation reaction Methods 0.000 description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 235000015165 citric acid Nutrition 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- UVPKUTPZWFHAHY-UHFFFAOYSA-L 2-ethylhexanoate;nickel(2+) Chemical compound [Ni+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O UVPKUTPZWFHAHY-UHFFFAOYSA-L 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003945 anionic surfactant Substances 0.000 description 6
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 150000005673 monoalkenes Chemical class 0.000 description 6
- 125000006353 oxyethylene group Chemical group 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 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 5
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 5
- 230000001737 promoting effect Effects 0.000 description 5
- 229940066528 trichloroacetate Drugs 0.000 description 5
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 239000004435 Oxo alcohol Substances 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-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
- 125000000129 anionic group Chemical group 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 230000003197 catalytic effect Effects 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
- 239000000539 dimer Substances 0.000 description 4
- 230000000694 effects Effects 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
- 150000002367 halogens Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000002808 molecular sieve Substances 0.000 description 4
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 4
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- 229910052697 platinum Inorganic materials 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 230000028327 secretion Effects 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 4
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- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
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- OYVHPJZBCZOMHZ-UHFFFAOYSA-L heptanoate;nickel(2+) Chemical compound [Ni+2].CCCCCCC([O-])=O.CCCCCCC([O-])=O OYVHPJZBCZOMHZ-UHFFFAOYSA-L 0.000 description 3
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- NWIRKPZFTCQKFA-UHFFFAOYSA-L 2-ethylbutanoate;nickel(2+) Chemical compound [Ni+2].CCC(CC)C([O-])=O.CCC(CC)C([O-])=O NWIRKPZFTCQKFA-UHFFFAOYSA-L 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
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 239000008237 rinsing water Substances 0.000 description 1
- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 description 1
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- 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
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- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
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- ODBLHEXUDAPZAU-UHFFFAOYSA-N threo-D-isocitric acid Natural products OC(=O)C(O)C(C(O)=O)CC(O)=O ODBLHEXUDAPZAU-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/755,827 US5780694A (en) | 1996-11-26 | 1996-11-26 | Dimerized alcohol compositions and biodegradible surfactants made therefrom having cold water detergency |
| US08/755,843 US5849960A (en) | 1996-11-26 | 1996-11-26 | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| PCT/EP1997/006694 WO1998023566A1 (en) | 1996-11-26 | 1997-11-25 | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL333503A1 PL333503A1 (en) | 1999-12-20 |
| PL197319B1 true PL197319B1 (pl) | 2008-03-31 |
Family
ID=27116135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL333503A PL197319B1 (pl) | 1996-11-26 | 1997-11-25 | Kompozycja rozgałęzionych pierwszorzędowych alkoholi, sposób jej wytwarzania oraz kompozycja detergentowa |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0958267B1 (OSRAM) |
| JP (1) | JP4118960B2 (OSRAM) |
| KR (1) | KR100641537B1 (OSRAM) |
| CN (1) | CN1090599C (OSRAM) |
| AU (1) | AU725968B2 (OSRAM) |
| BG (1) | BG64047B1 (OSRAM) |
| BR (1) | BR9713144B1 (OSRAM) |
| CA (1) | CA2271200C (OSRAM) |
| CZ (1) | CZ297436B6 (OSRAM) |
| DE (1) | DE69728429T2 (OSRAM) |
| ES (1) | ES2214650T3 (OSRAM) |
| NZ (1) | NZ334834A (OSRAM) |
| PL (1) | PL197319B1 (OSRAM) |
| PT (1) | PT958267E (OSRAM) |
| RO (1) | RO120404B1 (OSRAM) |
| RU (1) | RU2198159C2 (OSRAM) |
| SK (1) | SK285235B6 (OSRAM) |
| TR (1) | TR199901169T2 (OSRAM) |
| WO (1) | WO1998023566A1 (OSRAM) |
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| EG21174A (en) * | 1996-04-16 | 2000-12-31 | Procter & Gamble | Surfactant manufacture |
| MA24137A1 (fr) | 1996-04-16 | 1997-12-31 | Procter & Gamble | Fabrication d'agents de surface ramifies . |
| EG22088A (en) * | 1996-04-16 | 2002-07-31 | Procter & Gamble | Alkoxylated sulfates |
| DK0898607T3 (da) * | 1996-04-16 | 2002-09-02 | Procter & Gamble | Væskeformige rensesammensætninger, der indeholder udvalgte midtkædeforgrenede, overfladeaktive midler |
| 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 |
| JP2001520261A (ja) | 1997-10-14 | 2001-10-30 | ザ、プロクター、エンド、ギャンブル、カンパニー | 中鎖分岐界面活性剤を含む顆粒洗剤組成物 |
| EP1023042A1 (en) | 1997-10-14 | 2000-08-02 | 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 |
| DE19859911A1 (de) * | 1998-12-23 | 2000-06-29 | Basf Ag | Verfahren zur Herstellung von Tensidalkoholen und Tensidalkoholethern, die hergestellten Produkte und ihre Verwendung |
| 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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| US6765106B2 (en) * | 2001-02-15 | 2004-07-20 | Shell Oil Company | Process for preparing a branched olefin, a method of using the branched olefin for making a surfactant, and a surfactant |
| EP1241112A3 (en) | 2001-03-15 | 2003-02-26 | The Procter & Gamble Company | Flexible multiple compartment pouch |
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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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| DE102015207291A1 (de) | 2014-04-24 | 2016-03-10 | Basf Se | Weichmacher-Zusammensetzung, die Furanderivate und 1,2-Cyclohexandicarbonsäureester enthält |
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1997
- 1997-11-25 WO PCT/EP1997/006694 patent/WO1998023566A1/en not_active Ceased
- 1997-11-25 TR TR1999/01169T patent/TR199901169T2/xx unknown
- 1997-11-25 JP JP52430198A patent/JP4118960B2/ja not_active Expired - Lifetime
- 1997-11-25 AU AU56569/98A patent/AU725968B2/en not_active Ceased
- 1997-11-25 RO RO99-00592A patent/RO120404B1/ro unknown
- 1997-11-25 ES ES97952830T patent/ES2214650T3/es not_active Expired - Lifetime
- 1997-11-25 SK SK686-99A patent/SK285235B6/sk not_active IP Right Cessation
- 1997-11-25 DE DE69728429T patent/DE69728429T2/de not_active Revoked
- 1997-11-25 PL PL333503A patent/PL197319B1/pl not_active IP Right Cessation
- 1997-11-25 KR KR1019997004593A patent/KR100641537B1/ko not_active Expired - Fee Related
- 1997-11-25 RU RU99113994/04A patent/RU2198159C2/ru active
- 1997-11-25 CA CA002271200A patent/CA2271200C/en not_active Expired - Lifetime
- 1997-11-25 PT PT97952830T patent/PT958267E/pt unknown
- 1997-11-25 CZ CZ0184899A patent/CZ297436B6/cs not_active IP Right Cessation
- 1997-11-25 CN CN97199966A patent/CN1090599C/zh not_active Expired - Lifetime
- 1997-11-25 EP EP97952830A patent/EP0958267B1/en not_active Revoked
- 1997-11-25 NZ NZ334834A patent/NZ334834A/xx unknown
- 1997-11-25 BR BRPI9713144-0A patent/BR9713144B1/pt not_active IP Right Cessation
-
1999
- 1999-05-28 BG BG103445A patent/BG64047B1/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TR199901169T2 (xx) | 1999-08-23 |
| DE69728429D1 (de) | 2004-05-06 |
| WO1998023566A1 (en) | 1998-06-04 |
| SK285235B6 (sk) | 2006-09-07 |
| PL333503A1 (en) | 1999-12-20 |
| CZ297436B6 (cs) | 2006-12-13 |
| KR20000069117A (ko) | 2000-11-25 |
| ES2214650T3 (es) | 2004-09-16 |
| BG64047B1 (bg) | 2003-11-28 |
| AU5656998A (en) | 1998-06-22 |
| JP2001506597A (ja) | 2001-05-22 |
| BG103445A (en) | 2000-05-31 |
| EP0958267B1 (en) | 2004-03-31 |
| BR9713144B1 (pt) | 2009-01-13 |
| EP0958267A1 (en) | 1999-11-24 |
| KR100641537B1 (ko) | 2006-10-31 |
| PT958267E (pt) | 2004-08-31 |
| CA2271200A1 (en) | 1998-06-04 |
| SK68699A3 (en) | 1999-11-08 |
| BR9713144A (pt) | 2000-02-08 |
| CZ184899A3 (cs) | 1999-11-17 |
| CN1090599C (zh) | 2002-09-11 |
| CN1238749A (zh) | 1999-12-15 |
| AU725968B2 (en) | 2000-10-26 |
| RO120404B1 (ro) | 2006-01-30 |
| CA2271200C (en) | 2009-02-03 |
| JP4118960B2 (ja) | 2008-07-16 |
| NZ334834A (en) | 2000-07-28 |
| RU2198159C2 (ru) | 2003-02-10 |
| DE69728429T2 (de) | 2005-03-03 |
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