CA1185992A - Alcoxylation d'alcanols - Google Patents

Alcoxylation d'alcanols

Info

Publication number: CA1185992A
Authority: CA; Canada
Prior art keywords: alkanol; process according; component; aluminium; ponent
Prior art date: 1981-12-23
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000416773A

Other languages

English (en)

Inventor

Charles L. Edwards

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell Canada Ltd

Original Assignee

Shell Canada Ltd

Priority date (The priority date 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 date listed.)

1981-12-23

Filing date

1982-12-01

Publication date

1985-04-23

1981-12-23 Priority claimed from US06/334,091 external-priority patent/US4375564A/en

1982-12-01 Application filed by Shell Canada Ltd filed Critical Shell Canada Ltd

1985-04-23 Application granted granted Critical

1985-04-23 Publication of CA1185992A publication Critical patent/CA1185992A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 45
238000002360 preparation method Methods 0.000 title claims abstract description 12
125000002947 alkylene group Chemical group 0.000 claims abstract description 37
238000006243 chemical reaction Methods 0.000 claims abstract description 36
239000003426 co-catalyst Substances 0.000 claims abstract description 30
150000001875 compounds Chemical class 0.000 claims abstract description 18
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 12
229910052749 magnesium Inorganic materials 0.000 claims abstract description 12
239000011777 magnesium Substances 0.000 claims abstract description 12
239000004411 aluminium Substances 0.000 claims abstract description 11
229910052782 aluminium Inorganic materials 0.000 claims abstract description 11
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 11
150000007514 bases Chemical class 0.000 claims abstract description 10
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052796 boron Inorganic materials 0.000 claims abstract description 8
229910052725 zinc Inorganic materials 0.000 claims abstract description 8
239000011701 zinc Substances 0.000 claims abstract description 8
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 7
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 7
229910052719 titanium Inorganic materials 0.000 claims abstract description 6
239000010936 titanium Substances 0.000 claims abstract description 6
229910052721 tungsten Inorganic materials 0.000 claims abstract description 5
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims abstract description 4
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052787 antimony Inorganic materials 0.000 claims abstract description 4
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052750 molybdenum Inorganic materials 0.000 claims abstract description 4
239000011733 molybdenum Substances 0.000 claims abstract description 4
229910052718 tin Inorganic materials 0.000 claims abstract description 4
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims abstract description 4
239000010937 tungsten Substances 0.000 claims abstract description 4
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims abstract description 3
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 3
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052797 bismuth Inorganic materials 0.000 claims abstract description 3
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052793 cadmium Inorganic materials 0.000 claims abstract description 3
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052733 gallium Inorganic materials 0.000 claims abstract description 3
229910052732 germanium Inorganic materials 0.000 claims abstract description 3
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052735 hafnium Inorganic materials 0.000 claims abstract description 3
VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052738 indium Inorganic materials 0.000 claims abstract description 3
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052758 niobium Inorganic materials 0.000 claims abstract description 3
239000010955 niobium Substances 0.000 claims abstract description 3
GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052710 silicon Inorganic materials 0.000 claims abstract description 3
239000010703 silicon Substances 0.000 claims abstract description 3
229910052715 tantalum Inorganic materials 0.000 claims abstract description 3
GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052716 thallium Inorganic materials 0.000 claims abstract description 3
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052720 vanadium Inorganic materials 0.000 claims abstract description 3
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052727 yttrium Inorganic materials 0.000 claims abstract description 3
VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052726 zirconium Inorganic materials 0.000 claims abstract description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 12
RVDLHGSZWAELAU-UHFFFAOYSA-N 5-tert-butylthiophene-2-carbonyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)S1 RVDLHGSZWAELAU-UHFFFAOYSA-N 0.000 claims description 9
150000004703 alkoxides Chemical class 0.000 claims description 7
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 4
150000007942 carboxylates Chemical class 0.000 claims description 3
150000003567 thiocyanates Chemical class 0.000 claims description 3
JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 claims description 2
ORPJQHHQRCLVIC-UHFFFAOYSA-N magnesium;propan-2-olate Chemical compound CC(C)O[Mg]OC(C)C ORPJQHHQRCLVIC-UHFFFAOYSA-N 0.000 claims description 2
150000007944 thiolates Chemical class 0.000 claims description 2
239000000306 component Substances 0.000 claims 17
150000004767 nitrides Chemical class 0.000 claims 1
LWRYDHOHXNQTSK-UHFFFAOYSA-N thiophene oxide Chemical class O=S1C=CC=C1 LWRYDHOHXNQTSK-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 19
239000003599 detergent Substances 0.000 abstract description 5
238000009472 formulation Methods 0.000 abstract description 4
239000002736 nonionic surfactant Substances 0.000 abstract 1
239000000047 product Substances 0.000 description 40
239000003054 catalyst Substances 0.000 description 25
239000000376 reactant Substances 0.000 description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
238000009826 distribution Methods 0.000 description 10
150000002500 ions Chemical class 0.000 description 8
239000007788 liquid Substances 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
-1 alkyl ether sulphates Chemical class 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
230000006698 induction Effects 0.000 description 5
150000002681 magnesium compounds Chemical class 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
239000003377 acid catalyst Substances 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
238000007046 ethoxylation reaction Methods 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
230000000737 periodic effect Effects 0.000 description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001447 alkali salts Chemical class 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
150000001342 alkaline earth metals Chemical class 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
229910052788 barium Inorganic materials 0.000 description 3
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
239000011575 calcium Substances 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000012071 phase Substances 0.000 description 3
229910052712 strontium Inorganic materials 0.000 description 3
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 3
229910052723 transition metal Inorganic materials 0.000 description 3
150000003624 transition metals Chemical class 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
150000001242 acetic acid derivatives Chemical class 0.000 description 2
238000007259 addition reaction Methods 0.000 description 2
239000012018 catalyst precursor Substances 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000004880 explosion Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
239000011135 tin Substances 0.000 description 2
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-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
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
238000006136 alcoholysis reaction Methods 0.000 description 1
150000001399 aluminium compounds Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229940077746 antacid containing aluminium compound Drugs 0.000 description 1
GYIWFHXWLCXGQO-UHFFFAOYSA-N barium(2+);ethanolate Chemical compound [Ba+2].CC[O-].CC[O-] GYIWFHXWLCXGQO-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
150000003842 bromide salts Chemical class 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
229940043430 calcium compound Drugs 0.000 description 1
150000001674 calcium compounds Chemical class 0.000 description 1
JHLCADGWXYCDQA-UHFFFAOYSA-N calcium;ethanolate Chemical compound [Ca+2].CC[O-].CC[O-] JHLCADGWXYCDQA-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
150000004673 fluoride salts Chemical class 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
235000011167 hydrochloric acid Nutrition 0.000 description 1
238000007037 hydroformylation reaction Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
229940070765 laurate Drugs 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
150000004704 methoxides Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
238000004457 water analysis Methods 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000416773A 1981-12-23 1982-12-01 Alcoxylation d'alcanols Expired CA1185992A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US33409281A	1981-12-23	1981-12-23
US334,091		1981-12-23
US334,092		1981-12-23
US06/334,091 US4375564A (en)	1981-12-23	1981-12-23	Alkoxylation process

Publications (1)

Publication Number	Publication Date
CA1185992A true CA1185992A (fr)	1985-04-23

Family

ID=26989044

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000416773A Expired CA1185992A (fr)	1981-12-23	1982-12-01	Alcoxylation d'alcanols

Country Status (2)

Country	Link
AU (1)	AU551793B2 (fr)
CA (1)	CA1185992A (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4727199A (en) *	1985-07-10	1988-02-23	Union Carbide Corporation	Heterogeneous alkoxylation using anion-bound metal oxides
US4873017A (en) *	1985-07-10	1989-10-10	Union Carbide Corporation	Heterogeneous alkoxylation using anion-bound metal oxides
US4892977A (en) *	1988-06-13	1990-01-09	Texaco Chemical Company	Preparation of nonionic surfactants by oxyalkylation with a magnesium catalyst
US5012012A (en) *	1987-09-29	1991-04-30	Lion Corporation	Alkoxylation catalyst
US5025094A (en) *	1985-07-10	1991-06-18	Union Carbide Chemicals And Plastics Technology Corporation	Heterogeneous alkoxylation using anion-bound metal oxides
US5068456A (en) *	1988-06-13	1991-11-26	Texaco Chemical Company	Preparation of nonionic surfactants by oxyalkylation with a phenolic activated magnesium catalyst
US5136106A (en) *	1985-07-10	1992-08-04	Union Carbide Chemicals & Plastics Technology Corporation	Heterogeneous alkoxylation using anion-bound metal oxides

1982
- 1982-12-01 CA CA000416773A patent/CA1185992A/fr not_active Expired
- 1982-12-22 AU AU91790/82A patent/AU551793B2/en not_active Ceased

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4727199A (en) *	1985-07-10	1988-02-23	Union Carbide Corporation	Heterogeneous alkoxylation using anion-bound metal oxides
US4873017A (en) *	1985-07-10	1989-10-10	Union Carbide Corporation	Heterogeneous alkoxylation using anion-bound metal oxides
US5025094A (en) *	1985-07-10	1991-06-18	Union Carbide Chemicals And Plastics Technology Corporation	Heterogeneous alkoxylation using anion-bound metal oxides
US5136106A (en) *	1985-07-10	1992-08-04	Union Carbide Chemicals & Plastics Technology Corporation	Heterogeneous alkoxylation using anion-bound metal oxides
US5012012A (en) *	1987-09-29	1991-04-30	Lion Corporation	Alkoxylation catalyst
US4892977A (en) *	1988-06-13	1990-01-09	Texaco Chemical Company	Preparation of nonionic surfactants by oxyalkylation with a magnesium catalyst
US5068456A (en) *	1988-06-13	1991-11-26	Texaco Chemical Company	Preparation of nonionic surfactants by oxyalkylation with a phenolic activated magnesium catalyst

Also Published As

Publication number	Publication date
AU9179082A (en)	1983-06-30
AU551793B2 (en)	1986-05-08

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Date	Code	Title	Description
2002-04-24	MKEC	Expiry (correction)
2002-12-01	MKEX	Expiry

Publication	Publication Date	Title
EP0082554B1 (fr)	1985-03-20	Procédé pour la préparation d'alcanols alcoxylés
US4665236A (en)	1987-05-12	Alkoxylation process using bimetallic oxo catalyst
EP0082569B1 (fr)	1985-04-10	Procédé pour la préparation d'alcanols alcoxylés
US4721816A (en)	1988-01-26	Preparation of nonionic surfactants
EP0091146B1 (fr)	1986-01-15	Procédé de préparation d'alcoxylates d'alcanol
CA1157052A (fr)	1983-11-15	Catalyseur mineral pour l'alcoxylation des alcools
US4721817A (en)	1988-01-26	Preparation of nonionic surfactants
US4210764A (en)	1980-07-01	Barium oxide/cresylic acid catalyzed ethoxylation
JPS6332055B2 (fr)	1988-06-28
US5059719A (en)	1991-10-22	Alkoxylation process using catalyst of the lanthanum series
US4465877A (en)	1984-08-14	Magnesium catalyzed alkoxylation of alkanols in the presence of alkoxylate reaction activators
US4306093A (en)	1981-12-15	Strontium catalyzed alkoxylations
EP0538826B1 (fr)	1996-01-17	Procédé de production de l'acétate d'éthyle
CA1260018A (fr)	1989-09-26	Methode d'alcoxylation utilisant un catalyseur oxo bimetallique
CA1260017A (fr)	1989-09-26	Methode d'alcoxylation utilisant un catalyseur oxo bimetallique
US4575569A (en)	1986-03-11	Alkoxylation of thiols in the presence of a reaction promoter
US4689435A (en)	1987-08-25	Alkoxylation process using bimetallic oxo catalyst
JPS6029370B2 (ja)	1985-07-10	アルキレンオキシド付加物の製造方法
US4933502A (en)	1990-06-12	Process for the preparation of nonionic surfactants
US4825009A (en)	1989-04-25	Preparation of nonionic surfactants
EP1341607A1 (fr)	2003-09-10	Nouvelles compositions catalytiques a base d'antimoine
AU2001247096A1 (en)	2002-08-15	Novel antimony catalyst compositions
JPS63280036A (ja)	1988-11-17	アルコキシレ−トの製造方法
JPH0329769B2 (fr)	1991-04-25

CA1185992A - Alcoxylation d'alcanols - Google Patents

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Cited By (7)

Cited By (7)

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