WO2005104774B1 - Procede de fabrication de catalyseurs d'alkoxylation et utilisation dans le cadre de processus d'alkoxylation - Google Patents
Procede de fabrication de catalyseurs d'alkoxylation et utilisation dans le cadre de processus d'alkoxylationInfo
- Publication number
- WO2005104774B1 WO2005104774B1 PCT/US2005/014562 US2005014562W WO2005104774B1 WO 2005104774 B1 WO2005104774 B1 WO 2005104774B1 US 2005014562 W US2005014562 W US 2005014562W WO 2005104774 B1 WO2005104774 B1 WO 2005104774B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methyl
- pentanol
- butanol
- acid
- dimethyl
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims abstract 9
- 238000000034 method Methods 0.000 title claims 54
- 239000011575 calcium Substances 0.000 claims abstract 17
- 229910052791 calcium Inorganic materials 0.000 claims abstract 17
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract 15
- 238000009835 boiling Methods 0.000 claims abstract 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract 9
- 150000001875 compounds Chemical class 0.000 claims abstract 7
- 150000008064 anhydrides Chemical class 0.000 claims abstract 5
- 150000007522 mineralic acids Chemical class 0.000 claims abstract 5
- 238000004519 manufacturing process Methods 0.000 claims abstract 3
- 150000002148 esters Chemical class 0.000 claims 18
- 229960005069 Calcium Drugs 0.000 claims 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 14
- 239000000203 mixture Substances 0.000 claims 12
- 239000000376 reactant Substances 0.000 claims 11
- BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-Butanol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 10
- JYVLIDXNZAXMDK-UHFFFAOYSA-N 2-Pentanol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims 10
- 150000001298 alcohols Chemical class 0.000 claims 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 9
- AMQJEAYHLZJPGS-UHFFFAOYSA-N n-pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 9
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 9
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 claims 8
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-Methyl-1-butanol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 claims 8
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-Methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 claims 8
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-Methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 claims 8
- 150000001299 aldehydes Chemical class 0.000 claims 7
- 150000002576 ketones Chemical class 0.000 claims 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butanoic acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N Isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 6
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N 1-Hexanol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 5
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims 5
- AQIXEPGDORPWBJ-UHFFFAOYSA-N 3-Pentanol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 claims 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 5
- 150000002170 ethers Chemical class 0.000 claims 5
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 claims 5
- HMSVXZJWPVIVIV-UHFFFAOYSA-N 2,2-dimethylpentan-3-ol Chemical compound CCC(O)C(C)(C)C HMSVXZJWPVIVIV-UHFFFAOYSA-N 0.000 claims 4
- SXSWMAUXEHKFGX-UHFFFAOYSA-N 2,3-dimethylbutan-1-ol Chemical compound CC(C)C(C)CO SXSWMAUXEHKFGX-UHFFFAOYSA-N 0.000 claims 4
- BAYAKMPRFGNNFW-UHFFFAOYSA-N 2,4-dimethylpentan-3-ol Chemical compound CC(C)C(O)C(C)C BAYAKMPRFGNNFW-UHFFFAOYSA-N 0.000 claims 4
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-Ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 claims 4
- ISTJMQSHILQAEC-UHFFFAOYSA-N 2-Methyl-3-pentanol Chemical compound CCC(O)C(C)C ISTJMQSHILQAEC-UHFFFAOYSA-N 0.000 claims 4
- DUXCSEISVMREAX-UHFFFAOYSA-N 3,3-dimethylbutan-1-ol Chemical compound CC(C)(C)CCO DUXCSEISVMREAX-UHFFFAOYSA-N 0.000 claims 4
- IWTBVKIGCDZRPL-UHFFFAOYSA-N 3-Methyl-1-pentanol Chemical compound CCC(C)CCO IWTBVKIGCDZRPL-UHFFFAOYSA-N 0.000 claims 4
- ZXNBBWHRUSXUFZ-UHFFFAOYSA-N 3-Methyl-2-pentanol Chemical compound CCC(C)C(C)O ZXNBBWHRUSXUFZ-UHFFFAOYSA-N 0.000 claims 4
- PCWGTDULNUVNBN-UHFFFAOYSA-N 4-Methyl-1-pentanol Chemical compound CC(C)CCCO PCWGTDULNUVNBN-UHFFFAOYSA-N 0.000 claims 4
- ZDVJGWXFXGJSIU-UHFFFAOYSA-N 5-methylhexan-2-ol Chemical compound CC(C)CCC(C)O ZDVJGWXFXGJSIU-UHFFFAOYSA-N 0.000 claims 4
- RGCZULIFYUPTAR-UHFFFAOYSA-N 5-methylhexan-3-ol Chemical compound CCC(O)CC(C)C RGCZULIFYUPTAR-UHFFFAOYSA-N 0.000 claims 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 4
- HCRBXQFHJMCTLF-ZCFIWIBFSA-N Ethyl 2-methyl butyrate Natural products CCOC(=O)[C@H](C)CC HCRBXQFHJMCTLF-ZCFIWIBFSA-N 0.000 claims 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N Ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims 4
- JARKCYVAAOWBJS-UHFFFAOYSA-N Hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 claims 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N Hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N Isoamyl alcohol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N Methyl acetate Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 4
- DFOXKPDFWGNLJU-UHFFFAOYSA-N Pinacolyl alcohol Chemical compound CC(O)C(C)(C)C DFOXKPDFWGNLJU-UHFFFAOYSA-N 0.000 claims 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N Sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N Tert-Amyl alcohol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 4
- -1 aluminum alkoxide Chemical class 0.000 claims 4
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium monoxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 4
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-Methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 claims 3
- 235000011054 acetic acid Nutrition 0.000 claims 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atoms Chemical group C* 0.000 claims 3
- 235000019253 formic acid Nutrition 0.000 claims 3
- 229960002446 octanoic acid Drugs 0.000 claims 3
- 235000019260 propionic acid Nutrition 0.000 claims 3
- 239000001618 (3R)-3-methylpentan-1-ol Substances 0.000 claims 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-Propanediol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N 1-Decanol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N 1-Nonanol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 claims 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N 1-Tetradecanol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 1-butanal Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims 2
- PLSMHHUFDLYURK-UHFFFAOYSA-N 2,3,4-Trimethyl-3-pentanol Chemical compound CC(C)C(C)(O)C(C)C PLSMHHUFDLYURK-UHFFFAOYSA-N 0.000 claims 2
- IKECULIHBUCAKR-UHFFFAOYSA-N 2,3-dimethylbutan-2-ol Chemical compound CC(C)C(C)(C)O IKECULIHBUCAKR-UHFFFAOYSA-N 0.000 claims 2
- RFZHJHSNHYIRNE-UHFFFAOYSA-N 2,3-dimethylpentan-3-ol Chemical compound CCC(C)(O)C(C)C RFZHJHSNHYIRNE-UHFFFAOYSA-N 0.000 claims 2
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 claims 2
- FMLSQAUAAGVTJO-UHFFFAOYSA-N 2,4-dimethylpentan-2-ol Chemical compound CC(C)CC(C)(C)O FMLSQAUAAGVTJO-UHFFFAOYSA-N 0.000 claims 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-Ethylhexanol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N 2-Heptanone Chemical class CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Hexanone Chemical class CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims 2
- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-Methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 claims 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N 2-Pentanone Chemical class CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 2
- JCCIFDCPHCKATH-UHFFFAOYSA-N 2-methylbutan-2-yl acetate Chemical compound CCC(C)(C)OC(C)=O JCCIFDCPHCKATH-UHFFFAOYSA-N 0.000 claims 2
- KRIMXCDMVRMCTC-UHFFFAOYSA-N 2-methylhexan-2-ol Chemical compound CCCCC(C)(C)O KRIMXCDMVRMCTC-UHFFFAOYSA-N 0.000 claims 2
- CVKMFSAVYPAZTQ-UHFFFAOYSA-N 2-methylhexanoic acid Chemical compound CCCCC(C)C(O)=O CVKMFSAVYPAZTQ-UHFFFAOYSA-N 0.000 claims 2
- GLESBSXIWORDRL-UHFFFAOYSA-N 2-methylpentan-3-yl acetate Chemical compound CCC(C(C)C)OC(C)=O GLESBSXIWORDRL-UHFFFAOYSA-N 0.000 claims 2
- FZXRXKLUIMKDEL-UHFFFAOYSA-N 2-methylpropyl propanoate Chemical compound CCC(=O)OCC(C)C FZXRXKLUIMKDEL-UHFFFAOYSA-N 0.000 claims 2
- MAYGVGMOSXYCRX-UHFFFAOYSA-N 3,3-dimethylbutan-2-yl acetate Chemical compound CC(C)(C)C(C)OC(C)=O MAYGVGMOSXYCRX-UHFFFAOYSA-N 0.000 claims 2
- XKIRHOWVQWCYBT-UHFFFAOYSA-N 3-Ethylpentan-3-ol Chemical compound CCC(O)(CC)CC XKIRHOWVQWCYBT-UHFFFAOYSA-N 0.000 claims 2
- DMHIJUVUPKCGLJ-UHFFFAOYSA-N 3-ethyl-2-methylpentan-3-ol Chemical compound CCC(O)(CC)C(C)C DMHIJUVUPKCGLJ-UHFFFAOYSA-N 0.000 claims 2
- KYWJZCSJMOILIZ-UHFFFAOYSA-N 3-methylhexan-3-ol Chemical compound CCCC(C)(O)CC KYWJZCSJMOILIZ-UHFFFAOYSA-N 0.000 claims 2
- YKSWLQPMYFCNBG-UHFFFAOYSA-N 3-methyloctanoic acid Chemical compound CCCCCC(C)CC(O)=O YKSWLQPMYFCNBG-UHFFFAOYSA-N 0.000 claims 2
- DDQMXZFITHIRCN-UHFFFAOYSA-N 3-methylpentan-3-yl acetate Chemical compound CCC(C)(CC)OC(C)=O DDQMXZFITHIRCN-UHFFFAOYSA-N 0.000 claims 2
- CNQGBTJIGDAYTK-UHFFFAOYSA-N 4-ethylnonanoic acid Chemical compound CCCCCC(CC)CCC(O)=O CNQGBTJIGDAYTK-UHFFFAOYSA-N 0.000 claims 2
- CPIVYSAVIPTCCX-UHFFFAOYSA-N 4-methylpentan-2-yl acetate Chemical compound CC(C)CC(C)OC(C)=O CPIVYSAVIPTCCX-UHFFFAOYSA-N 0.000 claims 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N Amyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 229940010415 CALCIUM HYDRIDE Drugs 0.000 claims 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L Calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 claims 2
- UUGAXJGDKREHIO-UHFFFAOYSA-N Calcium hydride Chemical compound [H-].[H-].[Ca+2] UUGAXJGDKREHIO-UHFFFAOYSA-N 0.000 claims 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L Calcium hydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims 2
- MKJXYGKVIBWPFZ-UHFFFAOYSA-L Calcium lactate Chemical compound [Ca+2].CC(O)C([O-])=O.CC(O)C([O-])=O MKJXYGKVIBWPFZ-UHFFFAOYSA-L 0.000 claims 2
- QXDMQSPYEZFLGF-UHFFFAOYSA-L Calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 claims 2
- 229940087373 Calcium oxide Drugs 0.000 claims 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N Diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N Dodecanol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims 2
- 229940090910 ETHYL 2-METHYLBUTYRATE Drugs 0.000 claims 2
- OBNCKNCVKJNDBV-UHFFFAOYSA-N Ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims 2
- FXHGMKSSBGDXIY-UHFFFAOYSA-N Heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 claims 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N Heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N Isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 claims 2
- AVMSWPWPYJVYKY-UHFFFAOYSA-N Isobutyl formate Chemical compound CC(C)COC=O AVMSWPWPYJVYKY-UHFFFAOYSA-N 0.000 claims 2
- POULHZVOKOAJMA-UHFFFAOYSA-N Lauric acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N Linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims 2
- 229940017219 METHYL PROPIONATE Drugs 0.000 claims 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N Methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims 2
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N Palmitic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N Phenethyl alcohol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N Phosphorus pentoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N Propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims 2
- MCSINKKTEDDPNK-UHFFFAOYSA-N Propyl propanoate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 claims 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N Sec-Butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 2
- WMOVHXAZOJBABW-UHFFFAOYSA-N Tert-Butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 claims 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 2
- PVEOYINWKBTPIZ-UHFFFAOYSA-M but-3-enoate Chemical group [O-]C(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-M 0.000 claims 2
- OAEQYDZVVPONKW-UHFFFAOYSA-N butan-2-yl formate Chemical compound CCC(C)OC=O OAEQYDZVVPONKW-UHFFFAOYSA-N 0.000 claims 2
- VPSLGSSVPWVZFG-UHFFFAOYSA-N butan-2-yl propanoate Chemical compound CCC(C)OC(=O)CC VPSLGSSVPWVZFG-UHFFFAOYSA-N 0.000 claims 2
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 claims 2
- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propanoate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 2
- 239000001639 calcium acetate Substances 0.000 claims 2
- 235000011092 calcium acetate Nutrition 0.000 claims 2
- 229960005147 calcium acetate Drugs 0.000 claims 2
- 239000000920 calcium hydroxide Substances 0.000 claims 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims 2
- 229940095643 calcium hydroxide Drugs 0.000 claims 2
- 239000001527 calcium lactate Substances 0.000 claims 2
- 229960002401 calcium lactate Drugs 0.000 claims 2
- 235000011086 calcium lactate Nutrition 0.000 claims 2
- 239000000292 calcium oxide Substances 0.000 claims 2
- 239000001813 ethyl (2R)-2-methylbutanoate Substances 0.000 claims 2
- PPXUHEORWJQRHJ-UHFFFAOYSA-N ethyl isovalerate Chemical compound CCOC(=O)CC(C)C PPXUHEORWJQRHJ-UHFFFAOYSA-N 0.000 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- OUGPMNMLWKSBRI-UHFFFAOYSA-N hexyl formate Chemical compound CCCCCCOC=O OUGPMNMLWKSBRI-UHFFFAOYSA-N 0.000 claims 2
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Abstract
Procédé de fabrication de catalyseurs d'alkoxylation convenant pour des composés d'alkoxylation, consistant à mélanger un composé qui contient du calcium dans un milieu dispersant dont le point d'ébullition est inférieur à 160 °C avec un acide carboxylique et un acide ou un anhydride inorganiques.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200580021529.0A CN1976887B (zh) | 2004-04-27 | 2005-04-27 | 烷氧基化催化剂的制备方法及其在烷氧基化方法中的应用 |
| PL05740203T PL1747183T3 (pl) | 2004-04-27 | 2005-04-27 | Sposób wytwarzania katalizatorów alkoksylowania oraz ich zastosowanie w procesach alkoksylowania |
| EP05740203.4A EP1747183B1 (fr) | 2004-04-27 | 2005-04-27 | Procede de fabrication de catalyseurs d'alkoxylation et utilisation dans le cadre de processus d'alkoxylation |
Applications Claiming Priority (2)
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|---|---|---|---|
| US10/832,613 US7119236B2 (en) | 2004-04-27 | 2004-04-27 | Method of preparing alkoxylation catalysts and their use in alkoxylation processes |
| US10/832,613 | 2004-04-27 |
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| WO2005104774A2 WO2005104774A2 (fr) | 2005-11-10 |
| WO2005104774A3 WO2005104774A3 (fr) | 2006-02-16 |
| WO2005104774B1 true WO2005104774B1 (fr) | 2006-04-20 |
Family
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| PCT/US2005/014562 WO2005104774A2 (fr) | 2004-04-27 | 2005-04-27 | Procede de fabrication de catalyseurs d'alkoxylation et utilisation dans le cadre de processus d'alkoxylation |
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| US (1) | US7119236B2 (fr) |
| EP (1) | EP1747183B1 (fr) |
| CN (1) | CN1976887B (fr) |
| PL (1) | PL1747183T3 (fr) |
| WO (1) | WO2005104774A2 (fr) |
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| KR101208742B1 (ko) * | 2004-08-26 | 2012-12-05 | 헌츠만 페트로케미칼 엘엘씨 | 알칼리토류-기재 알콕실화 촉매 |
| CA2581342A1 (fr) | 2004-09-23 | 2006-03-30 | Akzo Nobel N.V. | Alkylamines alkoxylees/alkyletheramines alkoxylees presentant une distribution gaussienne |
| WO2007109791A2 (fr) * | 2006-03-23 | 2007-09-27 | Akzo Nobel N.V. | Alkyle ether amines/alkylamines alcoxyles avec repartition en crete |
| US20070282079A1 (en) * | 2006-05-31 | 2007-12-06 | Baker Hughes Incorporated | Alkoxylations in ketone solvents |
| US20100121111A1 (en) * | 2006-05-31 | 2010-05-13 | Baker Hughes Incorporated | Alkoxylations of High Melting Point Substrates in Ketone Solvents |
| WO2008006058A2 (fr) * | 2006-07-06 | 2008-01-10 | Stepan Company | Compositions de solvants d'alkyl lactyl lactate |
| EP2349974A1 (fr) * | 2008-10-29 | 2011-08-03 | Shell Internationale Research Maatschappij B.V. | Procédé de préparation d'alcoxylates d'alcools secondaires acylés et alcoxylates d'alcools secondaires |
| EP2181763B1 (fr) * | 2008-10-29 | 2012-06-20 | Shell Internationale Research Maatschappij B.V. | Catalyseur et procédé d'alcoxylation |
| US9266821B2 (en) * | 2009-10-16 | 2016-02-23 | Harcros Chemicals Inc. | Process for making fatty amides |
| CN104387247A (zh) * | 2014-11-19 | 2015-03-04 | 浙江绿科安化学有限公司 | 一种双羟乙基双酚a醚的制备方法 |
| EP3277415A1 (fr) | 2015-04-01 | 2018-02-07 | Valspar Sourcing, Inc. | Dispersion de pigment |
| WO2022129374A1 (fr) * | 2020-12-18 | 2022-06-23 | Unilever Ip Holdings B.V. | Composition détergente |
| EP4015497A1 (fr) * | 2020-12-18 | 2022-06-22 | Clariant International Ltd | Alkoxylates préparés par catalyseur de calcium |
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| CN116212962B (zh) * | 2023-02-24 | 2024-11-01 | 上海润和科华工程设计有限公司 | 一种油溶性异辛酸钼催化剂及其制备方法 |
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|---|---|---|---|---|
| US4239917A (en) | 1979-07-02 | 1980-12-16 | Conoco, Inc. | Barium oxide catalyzed ethoxylation |
| WO1985000365A1 (fr) | 1983-07-05 | 1985-01-31 | Union Carbide Corporation | Alcoxylation utilisant des catalyseurs au calcium et produits derives |
| US4775653A (en) | 1987-04-28 | 1988-10-04 | Vista Chemical Company | Alkoxylation process using calcium based catalysts |
| US4835321A (en) | 1987-04-28 | 1989-05-30 | Vista Chemical Company | Alkoxylaton process using calcium based catalysts |
| US5120697A (en) | 1988-09-30 | 1992-06-09 | Union Carbide Chemicals & Plastics Technology Corporation | Alkoxylation using modified calcium-containing catalysts |
| US5114900A (en) | 1988-09-30 | 1992-05-19 | Union Carbide Chemicals & Plastics Technology Corporation | Alkoxylation using modified calcium-containing bimetallic or polymetallic catalysts |
| US5386045A (en) | 1991-08-22 | 1995-01-31 | Vista Chemical Company | Process for alkoxylation of esters and products produced therefrom |
| US5220046A (en) | 1991-08-22 | 1993-06-15 | Vista Chemical Company | Process for alkoxylation of esters and products produced therefrom |
| US5627121A (en) | 1995-06-15 | 1997-05-06 | Condea Vista Company | Process for preparing alkoxylation catalysts and alkoxylation process |
| US6147246A (en) | 1999-12-23 | 2000-11-14 | Condea Vista Company | Process for preparing alkoxylated dialkyl carbonate compounds |
-
2004
- 2004-04-27 US US10/832,613 patent/US7119236B2/en not_active Expired - Lifetime
-
2005
- 2005-04-27 CN CN200580021529.0A patent/CN1976887B/zh active Active
- 2005-04-27 EP EP05740203.4A patent/EP1747183B1/fr active Active
- 2005-04-27 PL PL05740203T patent/PL1747183T3/pl unknown
- 2005-04-27 WO PCT/US2005/014562 patent/WO2005104774A2/fr active Application Filing
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