EP4045476A1 - Alcools alcoxylés et coiffés - Google Patents
Alcools alcoxylés et coiffésInfo
- Publication number
- EP4045476A1 EP4045476A1 EP20803629.3A EP20803629A EP4045476A1 EP 4045476 A1 EP4045476 A1 EP 4045476A1 EP 20803629 A EP20803629 A EP 20803629A EP 4045476 A1 EP4045476 A1 EP 4045476A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- octanol
- capped
- alcohol
- composition according
- chosen
- 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.)
- Pending
Links
- 150000001298 alcohols Chemical class 0.000 title claims description 20
- 239000000203 mixture Substances 0.000 claims abstract description 62
- 238000009826 distribution Methods 0.000 claims abstract description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 23
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 12
- 239000004094 surface-active agent Substances 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 238000005187 foaming Methods 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 3
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 claims description 107
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
- 239000003054 catalyst Substances 0.000 claims description 48
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 38
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 38
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 239000005968 1-Decanol Substances 0.000 claims description 19
- 150000003333 secondary alcohols Chemical class 0.000 claims description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 150000003138 primary alcohols Chemical class 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 claims description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 claims description 4
- 229920005862 polyol Polymers 0.000 claims description 4
- 150000003077 polyols Chemical class 0.000 claims description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims description 4
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 claims description 4
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 238000005260 corrosion Methods 0.000 claims description 3
- 230000007797 corrosion Effects 0.000 claims description 3
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 230000003165 hydrotropic effect Effects 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000006057 Non-nutritive feed additive Substances 0.000 claims description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical group OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 239000002216 antistatic agent Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims description 2
- 239000002761 deinking Substances 0.000 claims description 2
- 239000003792 electrolyte Substances 0.000 claims description 2
- 238000005188 flotation Methods 0.000 claims description 2
- 150000002334 glycols Chemical class 0.000 claims description 2
- 159000000011 group IA salts Chemical class 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 239000002480 mineral oil Substances 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000003973 paint Substances 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 238000005067 remediation Methods 0.000 claims description 2
- 239000002689 soil Substances 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
- 239000008158 vegetable oil Substances 0.000 claims description 2
- 239000012178 vegetable wax Substances 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- XDMBIDYMRMMSQN-UHFFFAOYSA-N 3-methyloxepane Chemical compound CC1CCCCOC1 XDMBIDYMRMMSQN-UHFFFAOYSA-N 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 76
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 75
- 229910052757 nitrogen Inorganic materials 0.000 description 38
- 238000006555 catalytic reaction Methods 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 32
- 239000012429 reaction media Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000003756 stirring Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 10
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000000977 initiatory effect Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 230000005587 bubbling Effects 0.000 description 4
- 238000007046 ethoxylation reaction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000010907 mechanical stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 125000000466 oxiranyl group Chemical group 0.000 description 3
- -1 oxybutylene Chemical group 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- 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
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 238000005555 metalworking Methods 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- GWMRZKNAZLBSPR-UHFFFAOYSA-N 1-phenylnonan-3-ol Chemical compound CCCCCCC(O)CCC1=CC=CC=C1 GWMRZKNAZLBSPR-UHFFFAOYSA-N 0.000 description 1
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 description 1
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 241000609240 Ambelania acida Species 0.000 description 1
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical compound OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 description 1
- FAYVLNWNMNHXGA-UHFFFAOYSA-N Cardanoldiene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1 FAYVLNWNMNHXGA-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- VGOBQSJWAVZUBY-UHFFFAOYSA-N [Na].[Na].CC(CCCCCC)O Chemical compound [Na].[Na].CC(CCCCCC)O VGOBQSJWAVZUBY-UHFFFAOYSA-N 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 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
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000010905 bagasse Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- PWZFXELTLAQOKC-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide;tetrahydrate Chemical compound O.O.O.O.[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O PWZFXELTLAQOKC-UHFFFAOYSA-A 0.000 description 1
- PKULCESNTQFEEL-UHFFFAOYSA-N diazanium;2-sulfobutanedioate Chemical class [NH4+].[NH4+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O PKULCESNTQFEEL-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000012978 lignocellulosic material Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- ZBJVLWIYKOAYQH-UHFFFAOYSA-N naphthalen-2-yl 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=C(C=CC=C2)C2=C1 ZBJVLWIYKOAYQH-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/20—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by addition of sulfurous acid or salts thereof to compounds having carbon-to-carbon multiple bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/38—Alcohols, e.g. oxidation products of paraffins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/17—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing carboxyl groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
-
- 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
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/08—Polyoxyalkylene derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2663—Metal cyanide catalysts, i.e. DMC's
-
- 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
- C11D1/721—End blocked ethers
Definitions
- the present invention relates to the general field of alkoxylated alcohols, and more particularly alkoxylated and capped alcohols (or “capped”), their preparation process and their uses as surfactants.
- alkoxylates of alcohols represent a family of compounds offering a wide range of properties, with multiple applications, such as solvents, hydrotropic agents or even surfactants.
- the alkoxylates of alcohols constitute a class of compounds of real industrial interest for a very large number of fields of application.
- the present invention relates to a composition comprising a mixture of alcohol alkoxylates, capped in the terminal part, composition in which:
- the alcohol comprises from 3 to 22, preferably from 5 to 22 carbon atoms, more preferably from 5 to 20, very particularly preferably from 5 to 18 carbon atoms,
- the weight distribution of the alkoxylates follows a monomodal distribution whose peak width value (2s) is less than 7, preferably less than 6, advantageously less than 5, more preferably less than 4, and
- the terminal part is capped by a group chosen from linear or branched alkyls comprising from 1 to 6 carbon atoms, the phenyl group, the group benzyl, hydrocarbon groups bearing a carboxy -COO- function, and groups bearing a sugar unit.
- the end cap of the alcohol alkoxylates is chosen from methyl, ethyl, propyl, butyl, benzyl and alkylcarboxyl-COOH groups and its salts.
- the possible salts of the carboxyl function there may be mentioned the salts well known to those skilled in the art and in particular the salts of metals, alkali metals, alkaline earth metals, ammonium, to name only the main of them.
- Particularly preferred salts are the sodium, potassium, calcium and ammonium salts.
- the end cap of the alcohol alkoxylates is chosen from alkylenecarboxyl and its salts, optionally functionalized.
- a typical and non-limiting example is represented by the sulfosuccinate group, and in particular sodium, potassium, calcium and ammonium sulfosuccinates.
- the end cap of the alcohol alkoxylates is chosen from groups carrying a sugar unit, such as for example glucose (case of monoglucosides), or two or more sugar units (the case of alkypolyglucosides, also called “APG”).
- a sugar unit such as for example glucose (case of monoglucosides), or two or more sugar units (the case of alkypolyglucosides, also called “APG”).
- the alcohol used as the starting substrate for the reaction (s) of alkoxylation comprises from 3 to 22, preferably from 5 to 22 carbon atoms, more preferably from 5 to 20 , very particularly preferably from 5 to 18 carbon atoms.
- the carbon atoms can be straight chain, branched or partly or totally cyclic.
- the alcohol has an average molar mass by weight ranging from 45 g mol 1 to 300 g mol 1 , preferably from 70 g mol 1 to 250 g mol 1 , more preferably from 80 g mol 1 at 200 g mol 1 .
- the alcohol used as the starting substrate can be of all types and of all origins.
- the alcohol is a primary alcohol or a secondary alcohol. It can be of petroleum origin, or of bio-sourced origin, for example of plant or animal origin. We prefer an alcohol of bio-sourced origin, for obvious reasons of environmental protection. It is also preferred to use a secondary alcohol for the purposes of the present invention.
- the alcohol when the alcohol is a primary alcohol, the latter can be chosen from linear or branched primary alcohols, for example from primary, linear or branched alcohols, comprising from 8 to 14 carbon atoms, for example 1 -octanol, 1-nonanol, 1-decanol, 1-undecanol, 1-dodecanol, 1-tridecanol, 1-tetradecanol, in particular alcohols with 10 carbon atoms, such as G Exxal TM 10, or alternatively alcohols with 13 carbon atoms, such as G Exxal TM 13, sold for example by Exxon Mobil.
- primary alcohols for example from primary, linear or branched alcohols, comprising from 8 to 14 carbon atoms, for example 1 -octanol, 1-nonanol, 1-decanol, 1-undecanol, 1-dodecanol, 1-tridecanol, 1-tetradecanol, in particular alcohols with 10 carbon atoms, such as G
- the alcohol when it is a secondary alcohol, it can be chosen from secondary alcohols comprising from 3 to 22 carbon atoms, linear or branched, and optionally comprising one or more aromatic group (s), of which the representatives may be phenolic alcohols, such as for example cardanol.
- the secondary alcohol contains from 3 to 22 carbon atoms, quite advantageously from 3 to 14 carbon atoms, more preferably from 6 to 12 carbon atoms. More preferably, the secondary alcohol is chosen from 2-octanol and 4-methyl2-pentanol, very particularly preferably, the secondary alcohol is 2-octanol.
- the alkoxylated repeating units are chosen from ethylene oxide, propylene oxide, butylene oxide and mixtures thereof.
- ethylene oxide unit is understood to mean a unit derived from ethylene oxide after opening of the oxirane ring.
- propylene oxide unit means a unit derived from propylene oxide after opening of the oxirane ring.
- butylene oxide unit means a unit derived from butylene oxide after opening of the oxirane ring.
- the capped alcohol alkoxylates comprise a sequence comprising one or more units chosen from the unit ethylene oxide, propylene oxide, butylene oxide and mixtures thereof, said units being distributed randomly, alternately or in blocks.
- the capped alcohol alkoxylates comprise ethylene oxide units, and a sequence comprising one or more units chosen from the unit ethylene oxide, propylene oxide, oxide of butylene and mixtures thereof, said units possibly being distributed randomly, alternately or in blocks, at least one propylene oxide or butylene oxide unit being present in said sequence.
- the capped alcohol alkoxylates comprise at least one ethylene oxide unit and at least one propylene oxide unit, distributed alternately, randomly or in blocks.
- the capped alcohol alkoxylates comprise at least one ethylene oxide unit and at least one butylene oxide unit, distributed alternately, randomly or in blocks.
- Another embodiment of the invention relates to capped alcohol alkoxylates comprising at least one propylene oxide unit and at least one butylene oxide unit, distributed alternately, randomly or in blocks.
- the number of repeating units is generally between, limits included, 1 and 100, preferably between 2 and 100, more preferably between 3 and 100, particularly between 3 and 80, more particularly between 3 and 75, preferably between 3 and 50, terminals included.
- the number of repeating units is between, limits included, 1 and 75, preferably between 2 and 75, more preferably between 3 and 75, particularly between 4 and 75 , more particularly between 5 and 75, preferably between 6 and 75, more preferably between 7 and 75, preferably between 8 and 75, even more preferably between 9 and 75 and very preferably between 10 and 75.
- the number of repeating units is between, limits included, 1 and 50, preferably between 2 and 50, more preferably between 3 and 50, particularly between 4 and 50, more particularly between 5 and 50, preferably between 6 and 50, more preferably between 7 and 50, preferably between 8 and 50, even more preferably between 9 and 50 and very preferably between 10 and 50.
- the number of repeating units is between, limits included, 1 and 30, preferably between 2 and 20, more preferably between 3 and 20, advantageously between 3 and 15.
- the capped alcohol alkoxylates are present in a monomodal weight distribution according to a normal law of statistical distribution.
- the composition of secondary alcohol alkoxylates exhibits a narrow monomodal weight distribution.
- the weight distribution is determined by analysis by gas chromatography on a standard column and flame ionization detection (FID) well known to those skilled in the art, where the various components of the compositions analyzed are separated by increasing boiling point and therefore by increasing molar mass by addition each time of an alkylene oxide unit.
- the weight distributions correspond to surface percentages assimilated to weight percentages, assuming that the products have the same response coefficient, because of the same chemical nature.
- compositions with a very wide weight distribution it is known that the substrate alkoxylation reactions, and in particular when the substrate is an alcohol, and more particularly when the alcohol is a secondary alcohol, by conventional routes (basic catalysis), leads to a very significant residual unreacted substrate.
- the capping reaction carried out on such compositions with wide distribution and significant residual can present difficulties of realization (reaction media which can be viscous making their handling difficult, insufficient yields, and others) and thus lead, in certain cases, to to capped alkoxylate compositions with application properties that are not very acceptable, or even mediocre. This is moreover very probably what explains why until now such capped alkoxylates have not developed industrially at the present time.
- the capped alcohol alkoxylates, and most particularly the capped secondary alcohol alkoxylates, described here have a narrow distribution, and in a very unexpectedly, greatly improved application performance.
- the compositions according to the present invention are used as surfactants, a less foaming effect and better detergent performance can be observed, compared to the compositions known and available on the market today.
- compositions according to the present invention by carrying out the styling reaction described above directly on “narrow range” alkoxylates already available commercially.
- These alkoxylates "narrow range” include for example those of the range Berol ®, marketed by the company Nouryon.
- Some of the capped alcohol alkoxylates described in this disclosure are new, and as such form part of the present invention.
- the invention relates to a composition
- a composition comprising a mixture of 2-octanol alkoxylates capped with narrow weight distribution, with a peak width value (2s) less than 7, preferably less than 6, more preferably less than 5, very preferably less than 4.
- the invention relates to a composition
- a composition comprising 2-octanol alkoxylates capped by a group chosen from linear or branched alkyls comprising from 1 to 6 carbon atoms, the phenyl group, the benzyl group, hydrocarbon groups carrying a carboxy -COO- function, and groups carrying a sugar unit, as defined above.
- the present invention relates to a composition
- a composition comprising
- alkyl group in particular chosen from methyl, ethyl, propyl, butyl or even with a benzyl group
- n is an integer between 1 and 5, limits included, optionally in the form of an alkali or alkaline salt earth, or ammonium, preferably Na + , K + , NH 4 + ).
- the present invention relates to a composition
- a composition comprising:
- a subject of the present invention is also a process for preparing the compositions according to the present invention as defined above, and comprising the following successive steps: a) reacting an alcohol with one or more alkylene oxides chosen from ethylene oxide, propylene oxide, butylene oxide and mixtures thereof, in the presence of at least one alkoxylation catalyst of “narrow range” type, preferably of the DMC type; b) reacting the product resulting from step (a) with one or more compounds capable of carrying out end-capping (“end-capping”).
- step a) The alkoxylation of step a) can be carried out with one or more alkylene oxides, simultaneously, sequentially, or alternately, depending on the order of the alkoxylated units desired in the final composition.
- the alkylene oxides used in the process of the present invention can be of various origins, and in particular "mass balance” alkylene oxides, in particular "mass balance” ethylene oxide.
- alkylene oxides of bio-sourced origin alkylene oxides of bio-sourced origin.
- the ethylene oxide used is of bio-sourced origin, for example ethylene oxide can be obtained by oxidation of bio-sourced ethylene originating from the dehydration of bio-ethanol, itself originating from corn starch, lignocellulosic materials, agricultural residues such as, for example, sugar cane bagasse, and the like.
- the alkoxylation reaction is carried out in the presence of a catalyst resulting in a narrow weight distribution of the alkoxylates obtained, and preferably with the lowest possible alcohol residual.
- a very suitable catalyst belongs to the family of catalysts of the dimetallic cyanide type (“DiMetallic Cyanide” or “DMC”).
- the product from step (a) can be isolated, although this is not necessary, in particular due to the fact that the residual starting alcohol content is quite minimal and negligible.
- the alcohol used in step a) of the process of the invention can be any alcohol known to those skilled in the art, and in particular, as described above, the alcohol is chosen from alcohols primary and secondary, preferably from secondary alcohols and preferably from 2-octanol and methyl isobutylcarbinol, the preferred alcohol being 2-octanol.
- 2-octanol is in fact of particular interest in several ways, in particular because it comes from a bio-sourced product and which does not compete with human or animal food.
- 2-octanol which has a high boiling point, is biodegradable and has a good ecotoxicological profile.
- the alcohol is used in step a) after drying, according to conventional techniques and well known to those skilled in the art, to such that the water content in said secondary alcohol is less than or equal to 200 ppm, preferably less than or equal to 100 ppm.
- the catalyst which can be used for the alkoxylation reaction of step a) of the process of the present invention can be any so-called “narrow range” catalyst known to those skilled in the art and in particular a catalyst of dimetallic cyanide type (DMC).
- DMC dimetallic cyanide type
- the catalyst used comprises zinc hexacyanocobaltate, and one or more ligands, such as the catalyst marketed by the Company under the name Covestro Arcol ® or the catalyst marketed by the company under the name Mexeo MEO-DMC ®.
- the content of catalyst of dimetallic cyanide type ranges from 1 ppm to 1000 ppm relative to the starting alcohol content, preferably from 1 ppm to 500 ppm, preferably from 2 ppm to 300 ppm, more preferably from 5 ppm to 200 ppm.
- the reaction can be carried out under all temperature and pressure conditions, as is well known to those skilled in the art, and according to a preferred embodiment, the reaction temperature during step (a) d
- the alkoxylation is generally between 80 ° C and 200 ° C, preferably between 00 ° C and 180 ° C.
- the reaction pressure during step (a) can range from 0.01 MPa to 3 MPa, preferably from 0.02 MPa to 2 MPa.
- the method according to the invention comprises a step of removing the residual oxides used in the alkoxylation and / or capping step, more particularly the oxides of ethylene, propylene, butylene and their. mixtures used during the process according to the invention.
- this step can take place after step (a) and / or after step (b), preferably after step a).
- residual oxide is understood to mean an oxide which has not reacted.
- said step of removing the residual oxide is carried out by cooking, that is to say by maintaining a temperature ranging from 70 ° C to 170 ° C, preferably from 100 ° C to 160 ° C, to consume the residual oxide, and / or by a stripping step under a stream of inert gas.
- said stripping step can be carried out under reduced pressure.
- the mass content of residual oxide is generally less than or equal to 0.05% relative to the total weight of alkoxylates, capped or not, depending on whether this removal step is carried out before or after step b), preferably less than or equal to 0.01%, more preferably less than or equal to 0.001%.
- the "end-capping" or capping reaction (step b) is carried out in a conventional manner, according to any method known to those skilled in the art, with or without a catalyst, and as for example described in documents EP2205711 and WO2004037960 , cited above.
- this capping reaction is carried out after formation of the alcoholate, in a basic medium (KOH, NaOH, for example), or else in the presence of a catalyst of the “narrow range” type, as described above, and in particular a DMC type catalyst, in particular when the capping is carried out using an alkylene oxide.
- the alkoxylate, or mixtures of alkoxylates are reacted in the form of an alkoxide with a halide (eg alkyl, benzyl, w-halogenated carboxylic acid, and the like) or else with an alkylene oxide. .
- the reaction medium is then neutralized, the salt formed is filtered, the expected product is recovered.
- a catalyst of the “narrow range” type and in particular a catalyst of the DMC type
- the process according to the present invention can be implemented in batch, semi-continuously or continuously.
- a person skilled in the art will know how to adapt the process for manufacturing the compositions according to the invention according to the random, alternating or block distribution of the desired chains of alkoxylates.
- the process according to the invention has the advantage of synthesizing the capped alcohol alkoxylates under good safety conditions, so that it can be carried out on an industrial scale.
- the operating conditions in terms of temperature and pressure are controlled by the method according to the invention.
- the exothermicity of the reaction can be controlled very easily.
- the capped alcohol alkoxylate compositions can most often be used as such, at the outlet of the reactor, without it being necessary to provide other purification, distillation or other steps. If necessary, conventional operations of filtration, drying, purification, and the like, can be carried out.
- a subject of the present invention is the use of a composition of capped alcohol alkoxylates according to the present invention, as a surfactant, and in particular as a low surfactant. foaming power ("low-foaming surfactant" in English).
- the compositions of the present invention which are characterized in particular by a narrow weight distribution, exhibit very advantageous application properties in terms of performance.
- the compositions of the present invention exhibit quite advantageous biodegradability profiles, in particular for low levels of alkoxylation ( ⁇ 8 units).
- the capped alcohol alkoxylates make them quite suitable compositions in a very large number of fields of application, such as for example, and in a nonlimiting manner, for detergency, for cosmetic products, for the flotation of ores, as a lubricant, in particular for metal working fluids ("Metal Working Fluids"), as an emulsifier, as an adjuvant for bituminous applications, as as a wetting agent, as a solvent, as a coalescing agent, as a processing aid, for deinking, as an anti-caking agent for hydrates gas, in enhanced gas and oil recovery applications, in corrosion protection, in hydraulic fracturing, in soil remediation, in agrochemicals (e.g.
- coatings of granular products especially fertilizers and products phytosanitary
- hydrotropic agent especially antistatic agent, paint adjuvant, textile adjuvant, for polyols, for the production of electrodes and electrolytes for batteries, to name only the main fields of application.
- a subject of the present invention is also a formulation comprising at least one composition of capped alcohol alkoxylates as defined above, and one or more aqueous, organic, hydro-organic solvents, chosen from water, alcohols, glycols. , polyols, mineral oils, vegetable oils, waxes, and others, alone or in mixtures of two or more of them, in all proportions.
- the formulation according to the invention can also contain one or more additives and fillers well known to those skilled in the art, such as for example, and without limitation, anionic, cationic, amphoteric or nonionic surfactants. , rheology modifiers, de-emulsifiers, anti-deposit agents, anti-foam agents, dispersants, pH control agents, colorants, anti-oxidants, preservatives, corrosion inhibitors, biocides, and other additives such as for example sulfur products , borates, nitrogen, phosphorus, and others.
- additives and fillers can vary widely depending on the nature of the application envisaged and can easily be adapted by those skilled in the art. The invention is now illustrated by the following examples which are in no way limiting.
- the 2-octanol (CAS RN 123-96-6) used is 2-octanol Oleris ® grade "Refined"(purity> 99%), marketed by Arkema France.
- Example A Comparison between KOH catalysis and DMC catalysis To illustrate the narrow distribution effect obtained by DMC catalysis, in comparison with a basic potassium hydroxide catalysis, an alkoxylation test of 2-octanol, at a rate of 1 mole of 2-octanol per 2 moles of propylene oxide, is carried out under the same operating conditions, on the one hand with a KOH catalyst and on the other hand with a DMC catalyst.
- the 2-octanol is dried beforehand (at less than 1000 ppm for KOH and less than 200 ppm for DMC).
- the amount of catalyst is equal to 2500 ppm KOH on the one hand, and 100 ppm DMC on the other hand.
- the reaction is carried out in an autoclave under a pressure of between 0.15 MPa and 0.6 MPa, at a temperature of between 130 ° C and 170 ° C.
- Table 1 The results, in terms of weight distribution of the alkoxylation compounds determined by gas chromatography, and expressed in% of peak area of each of the alkoxylates, are presented in Table 1 below:
- Example 1 Synthesis of 2-octanol 6 OE 4 OP in DMC catalysis
- 750 g (5.76 M) of 2-octanol dried at less than 200 ppm of water and 0.11 g (150 ppm) of DMC Arcol catalyst are charged ® .
- the reactor is closed, purged with nitrogen and the tightness under pressure is checked.
- the reactor is pressurized with nitrogen.
- the reaction medium is first brought to 90 ° C. with stirring. At a temperature of 120 ° C, 30 g of ethylene oxide are introduced.
- Example 2 Synthesis of 2-octanol 6 EO - 4 OB by DMC catalysis
- 500 g (3.84 M) of 2-octanol dried at less than 200 ppm are charged. of water and 0.075 g (150 ppm) of DMC Arcol ® catalyst.
- the reactor is closed, purged with nitrogen and the tightness under pressure is checked.
- the reactor is pressurized with nitrogen.
- the reaction medium is first brought to 90 ° C. with stirring. At a temperature of 120 ° C, 25 g of ethylene oxide are introduced.
- the balance of ethylene oxide is introduced, ie in all 2200 g (50 M) for a period of 3 h, at a temperature of approximately 140 ° C. At the end of the addition, the temperature is maintained for 30 min and then the residual ethylene oxide is stripped with nitrogen.
- the reactor is cooled to 80 ° C. and 2700 g of 13 EO 2-octanol product (IOH: 78 mg KOH / g and coloring at 20 Hz) are withdrawn.
- the product is a white solid at room temperature.
- reaction medium is then brought to 70 ° C., 342 g (2.7 M) of benzyl chloride are then added in approximately 60 min. The temperature is maintained for 5 hours at 120 ° C. After returning to 70 ° C, the reaction medium is neutralized with 37% hydrochloric acid until a pH of 7. Water is distilled off under reduced pressure to precipitate the sodium chloride formed. The latter is filtered and 2300 g of 13 EO capped benzyl 2-octanol are recovered.
- Example 5 Synthesis of 5 EO 1-Decanol by Basic KOH Catalysis
- the reactor is closed, purged with nitrogen and the pressure tightness is checked.
- the reactor is pressurized with nitrogen.
- the reaction medium is first brought to 90 ° C. with stirring. At a temperature of 120 ° C, 30 g of ethylene oxide are introduced.
- Example 6 Synthesis of 5 EO 1-decanol by DMC Catalysis
- the reactor is closed, purged with nitrogen and the tightness under pressure is checked.
- the reactor is pressurized with nitrogen.
- the reaction medium is first brought to 90 ° C. with stirring. At a temperature of 120 ° C, 35 g of ethylene oxide are introduced.
- Table 2 Weight distribution 1-decanol 5 EO - The 2s value calculated with the values resulting from the basic catalysis is 7.3, while this 2s value calculated with the values resulting from the DMC catalysis is 3.7.
- 500 g (3.16 M) of bio-sourced 1-decanol (marketed by Ecogreen) are charged, dried at less than 100 ppm of water. and 1.5 g (3000 ppm) of solid KOH.
- the reactor is closed, purged with nitrogen and the pressure tightness is checked.
- the reactor is pressurized with nitrogen.
- the reaction medium is first brought to 90 ° C. with stirring. At a temperature of 120 ° C, 30 g of ethylene oxide are introduced. When the reaction has started, the balance of ethylene oxide, a total of 1807 g (41 M), is introduced over 2 hours and 40 minutes at a temperature of about 140 ° C.
- the temperature is maintained for 30 min and then the residual ethylene oxide is stripped with nitrogen.
- the reactor is cooled to 80 ° C. and 2281 g of 13 EO 1-decanol product are withdrawn. (IOH: 77 mg KOH / g and 480 Hz staining on the molten product).
- the product is a white solid at room temperature.
- the reaction medium is brought to 90 ° C. under bubbling with azde in order to deoxygenate the medium. Nitrogen is then placed in the reactor chamber and then 120 g (3 M) of sodium hydroxide in beads are added.
- the medium is then brought to 100 ° C.-105 ° C. under reduced pressure to approximately 30 kPa so as to distill off the water.
- the stop criterion is a water content of less than 1.5%.
- the reaction medium is then brought to 70 ° C.
- the temperature is maintained for 30 min and then the residual ethylene oxide is stripped with nitrogen.
- the reactor is cooled to 80 ° C. and 2290 g of 13 EO 1-decanol product are withdrawn. (IOH: 75 mg KOH / g and 30 Hz staining on the molten product).
- the product is a white solid at room temperature.
- a nitrogen inerting system 2190 is charged.
- g (3M) of 13 EO 1-decanol obtained previously as well as 10 g of water.
- the reaction medium is brought to 90 ° C. under bubbling with nitrogen in order to deoxygenate the medium.
- Nitrogen is then placed in the reactor chamber and then 132 g (3.3 M) of sodium hydroxide in beads are added.
- the medium is then brought to 100 ° C-105 ° C and under reduced pressure up to about 30 kPa so as to distill the water.
- the stop criterion is a water content of less than 1.5%.
- reaction medium is then brought to 70 ° C., 366 g (2.9 M) of benzyl chloride are added in approximately 60 min. The temperature is maintained for 5 hours at 120 ° C. After returning to 70 ° C., the reaction medium is neutralized with 37% hydrochloric acid until a pH of 7. Water is distilled off under reduced pressure to precipitate the sodium chloride formed. The latter is filtered and 2390 g of 13 EO 1-decanol capped benzyl are recovered.
- the reaction medium is brought to a temperature between 60 ° C and 70 ° C, then 154 g (1.57 M) of maleic anhydride are gradually introduced with stirring while maintaining the temperature. After addition, the temperature is maintained at 70 ° C. for one hour. Then the esterification rate is checked by assay. Then poured, with stirring, 816 g of a 20% aqueous solution of sodium bisulfite (ie 1.57 M) at a temperature between 75 ° C and 90 ° C. After addition, the reaction medium is maiitient at 90 ° C. When the reaction is complete, the reaction medium is cooled, the pH is adjusted by adding sodium hydroxide solution and the reactor is emptied.
- the medium is brought with stirring and an inert atmosphere to 115 ° C. Then the assembly is gradually placed under reduced pressure to a value of 30 mm Hg (ie 4 kPa). The water formed is distilled and collected in a cold trap. The reaction is continued for about 7 hours, so as to convert all of the glucose.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Wood Science & Technology (AREA)
- Toxicology (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyethers (AREA)
- Cosmetics (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1911676A FR3102177B1 (fr) | 2019-10-18 | 2019-10-18 | Alcools alcoxylés et coiffés |
PCT/FR2020/051856 WO2021074544A1 (fr) | 2019-10-18 | 2020-10-16 | Alcools alcoxylés et coiffés |
Publications (1)
Publication Number | Publication Date |
---|---|
EP4045476A1 true EP4045476A1 (fr) | 2022-08-24 |
Family
ID=69810960
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP20803629.3A Pending EP4045476A1 (fr) | 2019-10-18 | 2020-10-16 | Alcools alcoxylés et coiffés |
Country Status (8)
Country | Link |
---|---|
US (1) | US20240059973A1 (fr) |
EP (1) | EP4045476A1 (fr) |
JP (1) | JP2022552997A (fr) |
CN (1) | CN114585717A (fr) |
BR (1) | BR112022004725A2 (fr) |
FR (1) | FR3102177B1 (fr) |
MX (1) | MX2022004227A (fr) |
WO (1) | WO2021074544A1 (fr) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114702661B (zh) * | 2022-03-29 | 2023-07-14 | 浙江皇马科技股份有限公司 | 一种清洗剂用的聚醚的制备方法 |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3359331A (en) | 1965-11-10 | 1967-12-19 | Exxon Research Engineering Co | Secondary alcohol ethoxylation |
AU5923400A (en) | 1999-07-09 | 2001-01-30 | Dow Chemical Company, The | Polymerization of ethylene oxide using metal cyanide catalysts |
US6462014B1 (en) * | 2001-04-09 | 2002-10-08 | Akzo Nobel N.V. | Low foaming/defoaming compositions containing alkoxylated quaternary ammonium compounds |
US6977236B2 (en) | 2002-06-14 | 2005-12-20 | Shell Oil Company | Preparation of a double metal cyanide catalyst |
DE10243366A1 (de) * | 2002-09-18 | 2004-04-01 | Basf Ag | Herstellung von Alkoxylaten bei optimierten Reaktionsdrücken |
ES2206052B1 (es) | 2002-10-24 | 2005-05-01 | Kao Corporation, S.A. | Uso de etercarboxilatos como lubricantes. |
DE10341724A1 (de) * | 2003-09-10 | 2005-04-21 | Basf Ag | In Alkalien stabile Alkoxylate |
US7189685B2 (en) * | 2004-07-23 | 2007-03-13 | Ecclab Inc. | Method and composition for removing hydrophobic soil |
DE102005006982A1 (de) * | 2005-02-15 | 2006-08-17 | Basf Ag | Verwendung nichtionischer Tenside bei der Metallgewinnung durch Elektrolyse |
US20080255378A1 (en) * | 2007-04-16 | 2008-10-16 | Bayer Materialscience Llc | High productivity process for non-phenolic ethoxylates |
US20090057608A1 (en) | 2007-06-27 | 2009-03-05 | Michiel Barend Eleveld | Alkoxylate composition and a process for preparing the same |
EP2178366A2 (fr) * | 2007-07-20 | 2010-04-28 | Basf Se | Substances contenant des alcoxylates d'alcool et utilisation des alcoxylates d'alcool en tant qu'adjuvants en agrochimie |
DE102007000501A1 (de) | 2007-10-15 | 2009-04-16 | Chemetall Gmbh | Reinigerzusammensetzung für metallische Oberflächen |
US20110319669A1 (en) | 2010-06-29 | 2011-12-29 | Wanglin Yu | Branched secondary alcohol alkoxylate surfactants and process to make them |
PL398518A1 (pl) | 2012-03-19 | 2013-09-30 | Hreczuch Wieslaw Mexeo | Sklad i sposób otrzymywania katalizatora oksyalkilenowania |
FR3073519A1 (fr) | 2017-11-10 | 2019-05-17 | Arkema France | Alcool secondaire alcoxyle |
FR3073517A1 (fr) * | 2017-11-10 | 2019-05-17 | Arkema France | Sulfates d'alcools secondaires alcoxyles |
-
2019
- 2019-10-18 FR FR1911676A patent/FR3102177B1/fr active Active
-
2020
- 2020-10-16 WO PCT/FR2020/051856 patent/WO2021074544A1/fr active Application Filing
- 2020-10-16 US US17/766,647 patent/US20240059973A1/en active Pending
- 2020-10-16 CN CN202080072935.4A patent/CN114585717A/zh active Pending
- 2020-10-16 MX MX2022004227A patent/MX2022004227A/es unknown
- 2020-10-16 EP EP20803629.3A patent/EP4045476A1/fr active Pending
- 2020-10-16 BR BR112022004725A patent/BR112022004725A2/pt active IP Right Grant
- 2020-10-16 JP JP2022522884A patent/JP2022552997A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
JP2022552997A (ja) | 2022-12-21 |
FR3102177A1 (fr) | 2021-04-23 |
MX2022004227A (es) | 2022-05-03 |
WO2021074544A1 (fr) | 2021-04-22 |
FR3102177B1 (fr) | 2023-05-19 |
US20240059973A1 (en) | 2024-02-22 |
BR112022004725A2 (pt) | 2022-06-14 |
CN114585717A (zh) | 2022-06-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP3706902B1 (fr) | Alcool secondaire alcoxylé | |
EP3347339B1 (fr) | Composés étheramines et leur utilisation en tant que collecteur de flottation | |
EP3668652B1 (fr) | Polyesteramines et polyesterquats | |
CA3079986C (fr) | Sulfates d'alcools secondaires alcoxyles | |
EP0950043A1 (fr) | Composes terpeniques polyalcoxyles, leur procede de preparation et leur utilisation comme agents demoussants | |
EP4045476A1 (fr) | Alcools alcoxylés et coiffés | |
WO2021074547A1 (fr) | Alcoxylats à pouvoir hydrotrope amélioré | |
EP2414434B1 (fr) | Procédé de préparation de superplastifiants | |
EP3707146B1 (fr) | Ester de phosphate d'alcool secondaire | |
US20100288167A1 (en) | Low diol content monofunctional alkoxypolyalkylene glycols and process for producing them | |
CN111253278A (zh) | 一种超高含量烷基醇酰胺、合成工艺及应用 | |
FR3056985A1 (fr) | Procede de fabrication de polyphenols alcoxyles | |
FR2972191A1 (fr) | Procede de preparation d'une composition tensioactive a base de bio-tensioactifs non-ioniques d'origine naturelle | |
EP3110783A1 (fr) | Procede de preparation a hauts rendements de p-(r)calix[9-20]arenes | |
FR3065218A1 (fr) | Procede de greffage de polyphenols | |
FR3102173A1 (fr) | Tensio-actifs à faible pouvoir moussant | |
EP4172237A1 (fr) | Procédé d'alcoxylation amélioré | |
EP0628531B1 (fr) | Procédé d'éthérification sélective d'un mono ou d'un polyalcool primaire ou secondaire | |
FR2575745A1 (fr) | Savons de cobalt oleosolubles | |
FR2512029A1 (fr) | Procede de preparation de sels d'acides dithiophosphoriques |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: UNKNOWN |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE |
|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE |
|
17P | Request for examination filed |
Effective date: 20220325 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
DAV | Request for validation of the european patent (deleted) | ||
DAX | Request for extension of the european patent (deleted) | ||
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: EXAMINATION IS IN PROGRESS |
|
17Q | First examination report despatched |
Effective date: 20231103 |