WO2005104774B1 - Method of preparing alkoxylation catalysts and their use in alkoxylation processes - Google Patents
Method of preparing alkoxylation catalysts and their use in alkoxylation processesInfo
- 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
- XKYICAQFSCFURC-UHFFFAOYSA-N isoamyl formate Chemical compound CC(C)CCOC=O XKYICAQFSCFURC-UHFFFAOYSA-N 0.000 claims 2
- RGFNRWTWDWVHDD-UHFFFAOYSA-N isobutyl butyrate Chemical compound CCCC(=O)OCC(C)C RGFNRWTWDWVHDD-UHFFFAOYSA-N 0.000 claims 2
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims 2
- 229940011051 isopropyl acetate Drugs 0.000 claims 2
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims 2
- OQAGVSWESNCJJT-UHFFFAOYSA-N methyl 3-methylbutanoate Chemical compound COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims 2
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical group [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 claims 2
- GQKZRWSUJHVIPE-UHFFFAOYSA-N pentan-2-yl acetate Chemical compound CCCC(C)OC(C)=O GQKZRWSUJHVIPE-UHFFFAOYSA-N 0.000 claims 2
- PBKYSIMDORTIEU-UHFFFAOYSA-N pentan-3-yl acetate Chemical compound CCC(CC)OC(C)=O PBKYSIMDORTIEU-UHFFFAOYSA-N 0.000 claims 2
- XRFWKHVQMACVTA-UHFFFAOYSA-N prop-2-enyl propanoate Chemical group CCC(=O)OCC=C XRFWKHVQMACVTA-UHFFFAOYSA-N 0.000 claims 2
- ZOIRKXLFEHOVER-UHFFFAOYSA-N propan-2-yl 3-methylbutanoate Chemical compound CC(C)CC(=O)OC(C)C ZOIRKXLFEHOVER-UHFFFAOYSA-N 0.000 claims 2
- FFOPEPMHKILNIT-UHFFFAOYSA-N propan-2-yl butanoate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 claims 2
- RMOUBSOVHSONPZ-UHFFFAOYSA-N propan-2-yl formate Chemical compound CC(C)OC=O RMOUBSOVHSONPZ-UHFFFAOYSA-N 0.000 claims 2
- IJMWOMHMDSDKGK-UHFFFAOYSA-N propan-2-yl propanoate Chemical compound CCC(=O)OC(C)C IJMWOMHMDSDKGK-UHFFFAOYSA-N 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims 2
- LSJMDWFAADPNAX-UHFFFAOYSA-N propyl 3-methylbutanoate Chemical compound CCCOC(=O)CC(C)C LSJMDWFAADPNAX-UHFFFAOYSA-N 0.000 claims 2
- 229940090181 propyl acetate Drugs 0.000 claims 2
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butanoate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 2
- QJHDFBAAFGELLO-UHFFFAOYSA-N sec-butyl butyrate Chemical group CCCC(=O)OC(C)CC QJHDFBAAFGELLO-UHFFFAOYSA-N 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N t-BuOH Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- SJSYJHLLBBSLIH-SDNWHVSQSA-N (E)-3-(2-methoxyphenyl)-2-phenylprop-2-enoic acid Chemical compound COC1=CC=CC=C1\C=C(\C(O)=O)C1=CC=CC=C1 SJSYJHLLBBSLIH-SDNWHVSQSA-N 0.000 claims 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N 1,2-ethanediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N 1,5-Pentanediol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims 1
- 229940043375 1,5-pentanediol Drugs 0.000 claims 1
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-Heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 1-Nonyl-4-phenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 claims 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims 1
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 claims 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-Butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims 1
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-Methyl-2,4-pentanediol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims 1
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-phenylpropan-1-ol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 claims 1
- KJWMCPYEODZESQ-UHFFFAOYSA-N 4-Dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C=C1 KJWMCPYEODZESQ-UHFFFAOYSA-N 0.000 claims 1
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-Ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 claims 1
- CGTLMVREWQIWEC-UHFFFAOYSA-N 4-decylphenol Chemical compound CCCCCCCCCCC1=CC=C(O)C=C1 CGTLMVREWQIWEC-UHFFFAOYSA-N 0.000 claims 1
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 claims 1
- KNDDEFBFJLKPFE-UHFFFAOYSA-N 4-n-Heptylphenol Chemical compound CCCCCCCC1=CC=C(O)C=C1 KNDDEFBFJLKPFE-UHFFFAOYSA-N 0.000 claims 1
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 claims 1
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N Cetyl alcohol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N Cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N Cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims 1
- FBPFZTCFMRRESA-KAZBKCHUSA-N D-Mannitol Natural products OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KAZBKCHUSA-N 0.000 claims 1
- UNXHWFMMPAWVPI-QWWZWVQMSA-N D-Threitol Natural products OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 claims 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N DETA Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N Diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N Dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims 1
- 239000004386 Erythritol Substances 0.000 claims 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N Erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims 1
- 229940009714 Erythritol Drugs 0.000 claims 1
- FBPFZTCFMRRESA-GUCUJZIJSA-N Galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 claims 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N Hexamethylenediamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims 1
- 239000005639 Lauric acid Substances 0.000 claims 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims 1
- CKFGINPQOCXMAZ-UHFFFAOYSA-N Methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 claims 1
- 235000021360 Myristic acid Nutrition 0.000 claims 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-Butylamine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N O-Toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims 1
- 239000005642 Oleic acid Substances 0.000 claims 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N P-Cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims 1
- 235000021314 Palmitic acid Nutrition 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N Phenylacetic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 1
- 229940067107 Phenylethyl Alcohol Drugs 0.000 claims 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N Phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 1
- 235000021355 Stearic acid Nutrition 0.000 claims 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N Stearyl alcohol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N Trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N Undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 235000019445 benzyl alcohol Nutrition 0.000 claims 1
- PUPZLCDOIYMWBV-UHFFFAOYSA-N butylene glycol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- QCRFMSUKWRQZEM-UHFFFAOYSA-N cycloheptanol Chemical compound OC1CCCCCC1 QCRFMSUKWRQZEM-UHFFFAOYSA-N 0.000 claims 1
- FHADSMKORVFYOS-UHFFFAOYSA-N cyclooctanol Chemical compound OC1CCCCCCC1 FHADSMKORVFYOS-UHFFFAOYSA-N 0.000 claims 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N decan-1-amine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 claims 1
- 229940097037 decylene glycol Drugs 0.000 claims 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecan-1-amine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims 1
- 235000019414 erythritol Nutrition 0.000 claims 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 1
- 235000019256 formaldehyde Nutrition 0.000 claims 1
- 125000005456 glyceride group Chemical group 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 1
- 235000011187 glycerol Nutrition 0.000 claims 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims 1
- 229940051250 hexylene glycol Drugs 0.000 claims 1
- 235000020778 linoleic acid Nutrition 0.000 claims 1
- 239000000594 mannitol Substances 0.000 claims 1
- 235000010355 mannitol Nutrition 0.000 claims 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 claims 1
- 235000021313 oleic acid Nutrition 0.000 claims 1
- REIUXOLGHVXAEO-UHFFFAOYSA-N pentadecan-1-ol Chemical compound CCCCCCCCCCCCCCCO REIUXOLGHVXAEO-UHFFFAOYSA-N 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 239000003279 phenylacetic acid Substances 0.000 claims 1
- 229960003424 phenylacetic acid Drugs 0.000 claims 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000600 sorbitol Substances 0.000 claims 1
- 235000010356 sorbitol Nutrition 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- TWBUVVYSQBFVGZ-UHFFFAOYSA-N tert-butyl butanoate Chemical compound CCCC(=O)OC(C)(C)C TWBUVVYSQBFVGZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 229940005605 valeric acid Drugs 0.000 claims 1
Abstract
A process for preparing an alkoxylation catalyst suitable for alkoxylating compounds that includes mixing a calcium-containing compound in a dispersing medium having a boiling point less that 160 °C with a carboxylic acid and an inorganic acid or anhydride.
Claims
1. A process for preparing an alkoxylation catalyst comprising: admixing a volatile dispersing medium consisting essentially of media having a boiling point less than 160 °C and comprised of one or more branched or straight chain alcohols, volatile esters, volatile ethers selected from the group consisting of dimethyl ether, diethyl ether, dimethoxy ethane, diethoxymethane, dibutylether, and isopropyl ether, or volatile aldehydes and ketones, a calcium-containing compound that is at least partially dispersible in said dispersing medium and a carboxylic acid or anhydride having from about 4 to about 15 carbon atoms, with the mole ratio of calcium to said carboxylic acid or anhydride being from about 15:1 to 1:1, to produce a calcium-containing composition.
2. The process according to claim 1, further comprising the step of adding an amount of an inorganic acid or anhydride to produce a partially neutralized calcium-containing catalyst.
3. The process of claim 2, wherein said inorganic acid or anhydride is selected from the group consisting of sulfuric acid, phosphoric acid, oleum, sulfur trioxide, and phosphorous pentoxide, or mixtures thereof.
4. The process according to claim 2, further comprising the step of adding an aluminum alkoxide to the calcium-containing composition.
5. The process of claim 2, including heating said partially neutralized composition at a temperature of from about 25 °C to about 160 0C under reflux conditions.
6. The process of claim 5, wherein said heating is conducted for a period of 1 to 5 hours.
7. The process of claim 1 , wherein said calcium-containing compound is selected from the group consisting of calcium hydride, calcium acetate, calcium oxalate, calcium oxide, calcium hydroxide, calcium lactate, calcium alkoxide, and mixtures thereof.
8. The process of claim 1, wherein said carboxylic acid is selected from the group consisting of octanoic acid, 2-methyl hexanoic acid, heptanoic acid, 3 -methyl octanoic acid, 4- ethyl nonanoic acid, 2-ethyl hexanoic acid, or mixtures thereof.
9. The process of claim 1, wherein said dispersing medium consists essentially of one or more branched or straight chain alcohols.
10. The process of claim 9, wherein said branched or straight chain alcohols are selected from the group consisting of methanol, ethanol, 1-propanol, 2-propanol, 2-methyl-l-propanol, 2-methyl-2-propanol, 1-butanol, 2,3 -dimethyl- 1-butanol, 3, 3 -dimethyl- 1-butanol, 2-ethyl-l- butanol, 2-methyl- 1-butanol, 3 -methyl- 1-butanol, 2-butanol, 2-methyl-2-butanol, 2,3-dimethyl- 2-butanol, 3,3-dimethyl-2-butanol, 3-methyl-2-butanol, 2-methyl- 1-pentanol, 3-methyl-l- pentanol, 4-methyl- 1-pentanol, 2-pentanol, 2,4-dimethyl-2-pentanol, 2-methyl-2-pentanol, 3- methyl-2-pentanol, 4-methyl-2-pentanol, 3-pentanol, 2,4,4-trimethyl-2-pentanol, 2,2-dimethyl- 3-pentanol, 2,3-dimethyl-3-pentanol, 2,4-dimethyl-3-pentanol, 3-ethyl-3-pentanol, 3-ethyl-2- methyl-3-pentanol, 2-methyl-3-pentanol, 2,3,4-trimethyl-3-pentanol, 1-pentanol, 1-hexanol, 2- hexanol, 2-methyl-2-hexanol, 5-methyl-2-hexanol, 3-hexanol, and 3-methyl-3-hexanol.
11. The process of claim 9, wherein said branched or straight chain alcohols are selected from the group consisting of ethanol, 1-propanol, 2-propanol, 2-methyl-l-propanol, 1-butanol, 2,3 -dimethyl- 1-butanol, 3, 3 -dimethyl- 1-butanol, 2-ethyl- 1-butanol, 2-methyl- 1-butanol, 3- methyl- 1-butanol, 2-butanol, 3,3-dimethyl-2-butanol, 3-methyl-2-butanol, 2-methyl- 1- pentanol, 3 -methyl- 1-pentanol, 4-methyl- 1-pentanol, 2-pentanol, 3-methyl-2-pentanol, 4- methyl-2-pentanol, 3-pentanol, 2,2-dimethyl-3-pentanol, 2,4-dimethyl-3-pentanol, 2-methyl-3- pentanol, 1-pentanol, 1-hexanol, 2-hexanol, 5-methyl-2-hexanol, and 3-hexanol.
12. The process of claim 1, wherein said dispersing medium consists essentially of one or more volatile esters.
13. The process according to claim 12, wherein said ester is an ester of formic acid, acetic acid, propionic acid, or butyric acid.
14. The process according to claim 12, wherein said ester is selected from the group consisting of allyl formate, butyl formate, isobutyl formate, sec-butyl formate, ethyl formate, hexyl formate, methyl formate, pentyl formate, isopentyl formate, propyl formate, and isopropyl formate.
15. The process according to claim 12, wherein said ester is selected from the group consisting of allyl acetate, butyl acetate, iso-butyl acetate, sec-butyl acetate, tert-butyl acetate, ethyl acetate, methyl acetate, tert-amyl acetate, isopentyl acetate, 2-methyl-3-pentyl acetate, 3- methyl-3 -pentyl acetate, 4-methyl-2 -pentyl acetate, pentyl acetate, 2-pentyl acetate, 3-pentyl acetate, propyl acetate, isopropyl acetate, and 1,2,2-trimethyl propyl acetate. 27
16. The process according to claim 12, wherein said ester is selected from the group consisting of allyl propionate, butyl propionate, isobutyl propionate, sec-butyl propionate, ethyl propionate, propyl propionate, isopropyl propionate, and methyl propionate.
17. The process according to claim 12, wherein said ester is selected from the group consisting of sec-butyl butyrate, iso-butyl butyrate, tert-butyl butyrate, ethylbutyrate, ethyl-2- methyl butyrate, isopropyl-3 -methyl butyrate, ethyl iso valerate, methyl iso valerate, propyl isovalerate, propyl butyrate, and iso-propyl butyrate.
18. The process of claim 1 , wherein said dispersing medium consists essentially of one or more volatile ethers.
19. The process of claim 18, wherein said ether is selected from the group consisting of dimethyl ether, diethyl ether, dimethoxy ethane, diethoxymethane, dibutylether, and isopropyl ether.
20. The process of claim 1, wherein said dispersing medium consists essentially of one or more volatile aldehydes and ketones.
21. The process of claim 20, wherein said aldehydes and ketones are selected from the group consisting of acetaldehyde, propionaldehyde, butyraldehyde, hexanal, heptanal, acetone, butanone, pentanones, hexanones, and heptanones.
22. The process of claim 1, wherein said dispersing medium consists essentially of media having a boiling point less than 120 °C.
23. The process of claim 1 , wherein said dispersing medium consists essentially of media having a boiling point between about 80 0C and 140 0C.
24. The process of claim 3, further comprising the step of removing the volatile dispersing medium to generate an active catalyst in a solid form.
25. A process for preparing an alkoxylation catalyst comprising: admixing a volatile dispersing medium consisting of media having a boiling point less than 160 °C and comprised of one or more branched or straight chain alcohols, volatile esters, volatile ethers selected from the group consisting of dimethyl ether, diethyl ether, dimethoxy ethane, diethoxymethane, dibutylether, and isopropyl ether, or volatile aldehydes and ketones, a calcium-containing compound that is at least partially dispersible in said dispersing medium 28
and a carboxylic acid or anhydride having from about 4 to about 15 carbon atoms, the mole ratio of calcium to said carboxylic acid or anhydride being from about 15:1 to 1 :1, to produce a calcium-containing composition.
26. An alkoxylation process comprising: forming an alkoxylation catalyst by admixing a volatile dispersing medium having a boiling point below about 160 0C and comprised of one or more branched or straight chain alcohols, volatile esters, volatile ethers selected from the group consisting of dimethyl ether, diethyl ether, dimethoxy ethane, diethoxymethane, dibutylether, and isopropyl ether, or volatile aldehydes and ketones, a calcium-containing compound that is at least partially dispersible in said volatile dispersing medium, and a carboxylic acid or anhydride having from about 4 to about 15 carbon atoms, with the mole ratio of calcium to said carboxylic acid or anhydride being from about 15 : 1 to 1 : 1 , to produce a calcium-containing composition having titratable alkalinity; and adding an amount of inorganic acid or anhydride to produce a partially neutralized calcium-containing alkoxylation catalyst; and reacting, in the presence of said alkoxylation catalyst, a reactant selected from the group consisting of alcohols, phenols, esters, glycerides, carboxylic acids, amides, and amines and mixtures thereof and an alkylene oxide under alkoxylation conditions to produce an alkoxylated derivative of said reactant.
27. The process of claim 26, wherein said reaction occurs at a temperature greater than about 160 0C.
28. The process of claim 26, wherein said reactant is selected from the group consisting of methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol; octadecanol, isopropyl alcohol, sec-butanol, isobutanol, 2-pentanol, 3-pentanol, 2-ethylhexanol, isodecanol, cyclopentanol, cyclohexanol, cycloheptanol, cyclooctanol, benzyl alcohol, phenylethyl alcohol, phenylpropyl alcohol, and 2-butoxy ethanol.
29. The process of claim 26, wherein said reactant is selected from the group consisting of p-methylphenol, p-ethylphenol, p-butylphenol, p-heptylphenol, p-octylphenol, p-nonylphenol, dinonylphenol, p-decylphenol, and p-dodecylphenol. 29
30. The process of claim 26, wherein said reactant is selected from the group consisting of ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, neopentylene glycol, decylene glycol, diethylene glycol, Methylene glycol, and dipropylene glycol.
31. The process of claim 26, wherein said reactant is selected from the group consisting of glycerin, 1,3-propanediol, pentaerythritol, galactitol, sorbitol, mannitol, erythritol, trimethylolethane and trimethylolpropane.
32. The process of claim 26, wherein said reactant is selected from the group consisting of formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, benzoic acid, phenylacetic acid, toluic acid, and phthalic acid.
33. The process of claim 26, wherein said reactant is selected from the group consisting of N,N-diethylamine, N-ethylamine, N-butylamine, N-octylamine, N-decylamine, N- dodecylamine, diethanolamine, hexamethylenediamine, ethylenediamine, diethylenetriamine, and trietheylenetetraamine.
34. The process of claim 26, wherein said volatile dispersing media is the same as said reactant.
35. The process of claim 26, wherein said volatile dispersing media is removed prior to said reacting step.
36. The process of claim 26, wherein said reactant has a boiling point greater than the boiling point of said dispersing medium.
37. The process of claim 26, wherein the reactant has boiling point about 20 °C or more higher than the boiling point of said dispersing medium.
38. The process of claim 26, wherein said calcium-containing compound is selected from the group consisting of calcium hydride, calcium acetate, calcium oxalate, calcium oxide, calcium hydroxide, calcium lactate, calcium alkoxide, and mixtures thereof.
39. The process of claim 26, wherein said carboxylic acid is selected from the group consisting of octanoic acid, 2-methyl hexanoic acid, heptanoic acid, 3-methyl octanoic acid, 4- ethyl nonanoic acid, 2-ethyl hexanoic acid, or mixtures thereof. 30
40. The process of claim 26, wherein said inorganic acid or anhydride is selected from the group consisting of sulfuric acid, phosphoric acid, oleum, sulfur trioxide, and phosphorous pentoxide, or mixtures thereof.
41. The process of claim 26, wherein said dispersing medium consists essentially of one or more branched or straight chain alcohols.
42. The process of claim 41 , wherein said branched or straight chain alcohols are selected from the group consisting of methanol, ethanol, 1-propanol, 2-propanol, 2-methyl-l-propanol, 2-methyl-2-propanol, 1-butanol, 2,3-dimethyl-l-butanol, 3,3-dimethyl-l-butanol, 2-ethyl-l- butanol, 2-methyl- 1-butanol, 3 -methyl- 1-butanol, 2-butanol, 2-methyl-2-butanol, 2,3-dimethyl- 2-butanol, 3,3-dimethyl-2-butanol, 3-methyl-2-butanol, 2-methyl- 1-pentanol, 3-methyl-l- pentanol, 4-methyl- 1-pentanol, 2-pentanol, 2,4-dimethyl-2-pentanol, 2-methyl-2-pentanol, 3- methyl-2-pentanol, 4-methyl-2-pentanol, 3-pentanol, 2,4,4-trimethyl-2-pentanol, 2,2-dimethyl- 3-pentanol, 2,3-dimethyl-3-pentanol, 2,4-dimethyl-3-pentanol, 3-ethyl-3-pentanol, 3-ethyl-2- methyl-3-pentanol, 2-methyl-3-pentanol, 2,3,4-trimethyl-3-pentanol, 1-pentanol, 1-hexanol, 2- hexanol, 2-methyl-2-hexanol, 5-methyl-2-hexanol, 3-hexanol, and 3-methyl-3-hexanol.
43. The process of claim 41, wherein said branched or straight chain alcohols are selected from the group consisting of ethanol, 1-propanol, 2-propanol, 2-methyl-l-propanol, 1-butanol, 2,3-dimethyl-l-butanol, 3,3-dimethyl-l-butanol, 2-ethyl- 1-butanol, 2-methyl- 1-butanol, 3- methyl- 1-butanol, 2-butanol, 3,3-dimethyl-2-butanol, 3-methyl-2-butanol, 2-methyl- 1- pentanol, 3 -methyl- 1-pentanol, 4-methyl- 1-pentanol, 2-pentanol, 3-methyl-2-pentanol, A- methyl-2-pentanol, 3-pentanol, 2,2-dimethyl-3-pentanol, 2,4-dimethyl-3-pentanol, 2-methyl-3- pentanol, 1-pentanol, 1-hexanol, 2-hexanol, 5-methyl-2-hexanol, and 3-hexanol.
44. The process of claim 26, wherein said dispersing medium consists essentially of one or more volatile esters.
45. The process according to claim 44, wherein said ester is an ester of formic acid, acetic acid, propionic acid, or butyric acid. 31
46. The process according to claim 45, wherein said ester is selected from the group consisting of allyl formate, butyl formate, isobutyl formate, sec-butyl formate, ethyl formate, hexyl formate, methyl formate, pentyl formate, isopentyl formate, propyl formate, and isopropyl formate.
47. The process according to claim 45, wherein said ester is selected from the group consisting of allyl acetate, butyl acetate, iso-butyl acetate, sec-butyl acetate, tert-butyl acetate, ethyl acetate, methyl acetate, tert-amyl acetate, isopentyl acetate, 2-methyl-3 -pentyl acetate, 3- methyl-3 -pentyl acetate, 4-methyl-2 -pentyl acetate, pentyl acetate, 2-pentyl acetate, 3 -pentyl acetate, propyl acetate, isopropyl acetate, and 1,2,2-trimethyl propyl acetate.
48. The process according to claim 45, wherein said ester is selected from the group consisting of allyl propionate, butyl propionate, isobutyl propionate, sec-butyl propionate, ethyl propionate, propyl propionate, isopropyl propionate, and methyl propionate.
49. The process according to claim 45, wherein said ester is selected from the group consisting of sec-butyl butyrate, iso-butyl butyrate, tert-butyl butryate, ethylbutyrate, ethyl-2- methyl butyrate, isopropyl-3 -methyl butyrate, ethyl iso valerate, methyl iso valerate, propyl isovalerate, propyl butyrate, and iso-propyl butyrate.
50. The process of claim 26, wherein said dispersing medium consists essentially of one or more volatile ethers.
51. The process of claim 50, wherein said ether is selected from the group consisting of dimethyl ether, diethyl ether, dimethoxy ethane, diethoxymethane, dibutylether, and isopropyl ether.
52. The process of claim 26, wherein said dispersing medium consists essentially of one or more volatile aldehydes and ketones.
53. The process of claim 52, wherein said aldehydes and ketones are selected from the group consisting of acetaldehyde, propionaldehyde, butyraldehyde, hexanal, heptanal, acetone, butanone, pentanones, hexanones, and heptanones.
54. The process of claim 26, wherein said dispersing medium consists essentially of media having a boiling point less than 120 0C. 32
55. The process of claim 26, wherein said dispersing medium consists essentially of media having a boiling point between about 80 0C and 140 °C.
Priority Applications (3)
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EP05740203.4A EP1747183B1 (en) | 2004-04-27 | 2005-04-27 | Method of preparing alkoxylation catalysts and their use in alkoxylation processes |
CN200580021529.0A CN1976887B (en) | 2004-04-27 | 2005-04-27 | Method of preparing alkoxylation catalysts and their use in alkoxylation processes |
PL05740203T PL1747183T3 (en) | 2004-04-27 | 2005-04-27 | Method of preparing alkoxylation catalysts and their use in alkoxylation processes |
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US10/832,613 | 2004-04-27 | ||
US10/832,613 US7119236B2 (en) | 2004-04-27 | 2004-04-27 | Method of preparing alkoxylation catalysts and their use in alkoxylation processes |
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US (1) | US7119236B2 (en) |
EP (1) | EP1747183B1 (en) |
CN (1) | CN1976887B (en) |
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CN101374599B (en) * | 2004-08-26 | 2013-01-09 | 亨斯迈石油化学有限责任公司 | Alkaline earth-based alkoxylation catalysts |
MX2007003478A (en) * | 2004-09-23 | 2007-08-17 | Akzo Nobel Nv | Alkoxylated alkylamines / alkyl ether amines with peaked distribution. |
JP2009531329A (en) * | 2006-03-23 | 2009-09-03 | アクゾ・ノベル・エヌ・ベー | Alkoxylated alkyl amine / alkyl ether amine with peak distribution |
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 (en) * | 2006-07-06 | 2008-01-10 | Stepan Company | Alkyl lactyllactate solvent compositions |
KR20110077028A (en) * | 2008-10-29 | 2011-07-06 | 쉘 인터내셔날 리써취 마트샤피지 비.브이. | Process for the preparation of acylated secondary alcohol alkoxylates and secondary alcohol alkoxylates |
PL2181763T3 (en) * | 2008-10-29 | 2012-11-30 | Shell Int Research | Catalyst and process for alkoxylation |
US9266821B2 (en) * | 2009-10-16 | 2016-02-23 | Harcros Chemicals Inc. | Process for making fatty amides |
CN104387247A (en) * | 2014-11-19 | 2015-03-04 | 浙江绿科安化学有限公司 | Method for preparing bis(hydroxyethyl) bisphenol A ether |
WO2016161387A1 (en) | 2015-04-01 | 2016-10-06 | Valspar Sourcing, Inc. | Pigment dispersion |
WO2022129374A1 (en) * | 2020-12-18 | 2022-06-23 | Unilever Ip Holdings B.V. | Detergent composition |
EP4015497A1 (en) * | 2020-12-18 | 2022-06-22 | Clariant International Ltd | Alkoxylates prepared by calcium catalyst |
WO2023067074A1 (en) | 2021-10-21 | 2023-04-27 | Unilever Ip Holdings B.V. | Detergent compositions |
EP4349946A1 (en) | 2022-10-05 | 2024-04-10 | Unilever IP Holdings B.V. | Unit dose fabric treatment product |
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WO2024088706A1 (en) | 2022-10-25 | 2024-05-02 | Unilever Ip Holdings B.V. | Composition |
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WO2024088716A1 (en) | 2022-10-25 | 2024-05-02 | Unilever Ip Holdings B.V. | Composition |
WO2024115106A1 (en) | 2022-11-29 | 2024-06-06 | Unilever Ip Holdings B.V. | Composition |
CN116212962A (en) * | 2023-02-24 | 2023-06-06 | 润和科华催化剂(上海)有限公司 | Oil-soluble molybdenum isooctanoate catalyst and preparation method thereof |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4239917A (en) | 1979-07-02 | 1980-12-16 | Conoco, Inc. | Barium oxide catalyzed ethoxylation |
WO1985000365A1 (en) | 1983-07-05 | 1985-01-31 | Union Carbide Corporation | Alkoxylation using calcium catalysts and products therefrom |
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 |
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