JPH09504011A - アルコキシル化の方法 - Google Patents

アルコキシル化の方法

Info

Publication number: JPH09504011A
Authority: JP; Japan
Prior art keywords: group; catalyst; alkoxylation; elements; hydrophobic
Prior art date: 1993-10-22
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP7511104A

Other languages

English (en)

Japanese (ja)

Inventor

レギナルドドイチャー，ケネス

ファーヌギアン，キアー

ウォルターパール，ロドニー

パリス，デビッド

エリザベスタスデレン，エセンナー

Original Assignee

アイシーアイオーストラリアオペレイションズプロプライアタリーリミティド

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.)

1993-10-22

Filing date

1994-10-21

Publication date

1997-04-22

1994-10-21 Application filed by アイシーアイオーストラリアオペレイションズプロプライアタリーリミティド filed Critical アイシーアイオーストラリアオペレイションズプロプライアタリーリミティド

1997-04-22 Publication of JPH09504011A publication Critical patent/JPH09504011A/ja

Status Pending legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 109
239000003054 catalyst Substances 0.000 claims abstract description 191
239000000203 mixture Substances 0.000 claims abstract description 52
150000002894 organic compounds Chemical class 0.000 claims abstract description 39
150000003839 salts Chemical class 0.000 claims abstract description 23
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
239000001257 hydrogen Substances 0.000 claims abstract description 22
125000001165 hydrophobic group Chemical group 0.000 claims abstract description 22
125000002947 alkylene group Chemical group 0.000 claims abstract description 20
229910052761 rare earth metal Inorganic materials 0.000 claims abstract description 18
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 72
229910052746 lanthanum Inorganic materials 0.000 claims description 71
FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 66
230000002209 hydrophobic effect Effects 0.000 claims description 40
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 39
-1 polyethylene Polymers 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 20
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
230000008569 process Effects 0.000 claims description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 15
229910052719 titanium Inorganic materials 0.000 claims description 15
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 13
239000002243 precursor Substances 0.000 claims description 12
125000000962 organic group Chemical group 0.000 claims description 11
229910052788 barium Inorganic materials 0.000 claims description 10
239000005909 Kieselgur Substances 0.000 claims description 8
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 8
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 8
JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical group [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 claims description 8
229910002113 barium titanate Inorganic materials 0.000 claims description 8
238000012545 processing Methods 0.000 claims description 8
229910052712 strontium Inorganic materials 0.000 claims description 8
150000001298 alcohols Chemical class 0.000 claims description 7
229910052727 yttrium Inorganic materials 0.000 claims description 7
238000010438 heat treatment Methods 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 5
229910052791 calcium Inorganic materials 0.000 claims description 5
239000011575 calcium Substances 0.000 claims description 5
229910052735 hafnium Inorganic materials 0.000 claims description 5
150000004679 hydroxides Chemical class 0.000 claims description 5
229910052750 molybdenum Inorganic materials 0.000 claims description 5
229910052758 niobium Inorganic materials 0.000 claims description 5
229910052700 potassium Inorganic materials 0.000 claims description 5
229910052726 zirconium Inorganic materials 0.000 claims description 5
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 4
229910021523 barium zirconate Inorganic materials 0.000 claims description 4
DQBAOWPVHRWLJC-UHFFFAOYSA-N barium(2+);dioxido(oxo)zirconium Chemical compound [Ba+2].[O-][Zr]([O-])=O DQBAOWPVHRWLJC-UHFFFAOYSA-N 0.000 claims description 4
150000002430 hydrocarbons Chemical group 0.000 claims description 4
VOPSYYWDGDGSQS-UHFFFAOYSA-N neodymium(3+);oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Ti+4].[Ti+4].[Nd+3].[Nd+3] VOPSYYWDGDGSQS-UHFFFAOYSA-N 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
229910052721 tungsten Inorganic materials 0.000 claims description 4
FFQALBCXGPYQGT-UHFFFAOYSA-N 2,4-difluoro-5-(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=C(F)C=C1F FFQALBCXGPYQGT-UHFFFAOYSA-N 0.000 claims description 3
229910052684 Cerium Inorganic materials 0.000 claims description 3
229910052779 Neodymium Inorganic materials 0.000 claims description 3
239000004743 Polypropylene Substances 0.000 claims description 3
HYXRNUXQERMPQH-UHFFFAOYSA-N [K].[La] Chemical compound [K].[La] HYXRNUXQERMPQH-UHFFFAOYSA-N 0.000 claims description 3
AOWKSNWVBZGMTJ-UHFFFAOYSA-N calcium titanate Chemical compound [Ca+2].[O-][Ti]([O-])=O AOWKSNWVBZGMTJ-UHFFFAOYSA-N 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
229910052749 magnesium Inorganic materials 0.000 claims description 3
MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 claims description 3
229920001155 polypropylene Polymers 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims description 3
239000004698 Polyethylene Substances 0.000 claims description 2
239000004642 Polyimide Substances 0.000 claims description 2
239000000395 magnesium oxide Substances 0.000 claims description 2
229920000573 polyethylene Polymers 0.000 claims description 2
229920001223 polyethylene glycol Polymers 0.000 claims description 2
229920001721 polyimide Polymers 0.000 claims description 2
239000000377 silicon dioxide Substances 0.000 claims description 2
150000005846 sugar alcohols Polymers 0.000 claims description 2
VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 claims 4
150000002431 hydrogen Chemical class 0.000 claims 3
229910052454 barium strontium titanate Inorganic materials 0.000 claims 2
229920006395 saturated elastomer Polymers 0.000 claims 2
239000004793 Polystyrene Substances 0.000 claims 1
150000002334 glycols Chemical class 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
229920001451 polypropylene glycol Polymers 0.000 claims 1
229920002223 polystyrene Polymers 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
239000000047 product Substances 0.000 description 58
238000006243 chemical reaction Methods 0.000 description 44
238000009826 distribution Methods 0.000 description 31
239000010936 titanium Substances 0.000 description 30
239000000243 solution Substances 0.000 description 29
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
239000007787 solid Substances 0.000 description 17
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 11
230000000694 effects Effects 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000000969 carrier Substances 0.000 description 9
239000008367 deionised water Substances 0.000 description 9
229910021641 deionized water Inorganic materials 0.000 description 9
238000007429 general method Methods 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
230000000052 comparative effect Effects 0.000 description 8
FYDKNKUEBJQCCN-UHFFFAOYSA-N lanthanum(3+);trinitrate Chemical compound [La+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O FYDKNKUEBJQCCN-UHFFFAOYSA-N 0.000 description 8
239000012876 carrier material Substances 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
235000011114 ammonium hydroxide Nutrition 0.000 description 6
150000002989 phenols Chemical class 0.000 description 6
239000011148 porous material Substances 0.000 description 6
239000000376 reactant Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
239000005977 Ethylene Substances 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
238000007046 ethoxylation reaction Methods 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
FVDRFBGMOWJEOR-UHFFFAOYSA-N hexadecan-2-ol Chemical compound CCCCCCCCCCCCCCC(C)O FVDRFBGMOWJEOR-UHFFFAOYSA-N 0.000 description 4
239000002245 particle Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 3
230000008570 general process Effects 0.000 description 3
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150000002924 oxiranes Chemical class 0.000 description 3
238000005453 pelletization Methods 0.000 description 3
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KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
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AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
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229920002253 Tannate Polymers 0.000 description 2
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230000002378 acidificating effect Effects 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
150000004703 alkoxides Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
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230000015572 biosynthetic process Effects 0.000 description 2
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125000004432 carbon atom Chemical group C* 0.000 description 2
SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 2
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238000007796 conventional method Methods 0.000 description 2
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XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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238000001035 drying Methods 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
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238000005470 impregnation Methods 0.000 description 2
238000002955 isolation Methods 0.000 description 2
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235000021313 oleic acid Nutrition 0.000 description 2
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238000006884 silylation reaction Methods 0.000 description 2
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CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical group [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
TYWMIZZBOVGFOV-UHFFFAOYSA-N tetracosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCO TYWMIZZBOVGFOV-UHFFFAOYSA-N 0.000 description 2
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240000007124 Brassica oleracea Species 0.000 description 1
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241000196324 Embryophyta Species 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
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235000021353 Lignoceric acid Nutrition 0.000 description 1
CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 1
TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
229910052776 Thorium Inorganic materials 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000012190 activator Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
235000012501 ammonium carbonate Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001553 barium compounds Chemical class 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
WAKZZMMCDILMEF-UHFFFAOYSA-H barium(2+);diphosphate Chemical compound [Ba+2].[Ba+2].[Ba+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O WAKZZMMCDILMEF-UHFFFAOYSA-H 0.000 description 1
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
150000004652 butanoic acids Chemical class 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
239000001175 calcium sulphate Substances 0.000 description 1
235000011132 calcium sulphate Nutrition 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
235000013351 cheese Nutrition 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000004020 conductor Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
229910052747 lanthanoid Inorganic materials 0.000 description 1
150000002602 lanthanoids Chemical class 0.000 description 1
VQEHIYWBGOJJDM-UHFFFAOYSA-H lanthanum(3+);trisulfate Chemical compound [La+3].[La+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VQEHIYWBGOJJDM-UHFFFAOYSA-H 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
229910001641 magnesium iodide Inorganic materials 0.000 description 1
125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910003455 mixed metal oxide Inorganic materials 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
XGFDHKJUZCCPKQ-UHFFFAOYSA-N n-nonadecyl alcohol Natural products CCCCCCCCCCCCCCCCCCCO XGFDHKJUZCCPKQ-UHFFFAOYSA-N 0.000 description 1
FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
KHLCTMQBMINUNT-UHFFFAOYSA-N octadecane-1,12-diol Chemical compound CCCCCCC(O)CCCCCCCCCCCO KHLCTMQBMINUNT-UHFFFAOYSA-N 0.000 description 1
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
ALSTYHKOOCGGFT-MDZDMXLPSA-N oleyl alcohol Chemical compound CCCCCCCC\C=C\CCCCCCCCO ALSTYHKOOCGGFT-MDZDMXLPSA-N 0.000 description 1
239000011368 organic material Substances 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000005702 oxyalkylene group Chemical group 0.000 description 1
239000008188 pellet Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
229940100684 pentylamine Drugs 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
PJPOCNJHYFUPCE-UHFFFAOYSA-N picen-1-ol Chemical compound C1=CC=CC2=C(C=CC=3C4=CC=C5C=CC=C(C=35)O)C4=CC=C21 PJPOCNJHYFUPCE-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000036632 reaction speed Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 1
229910052706 scandium Inorganic materials 0.000 description 1
SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
241000894007 species Species 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
QZZGJDVWLFXDLK-UHFFFAOYSA-N tetracosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(O)=O QZZGJDVWLFXDLK-UHFFFAOYSA-N 0.000 description 1
150000003567 thiocyanates Chemical class 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
LKOVPWSSZFDYPG-WUKNDPDISA-N trans-octadec-2-enoic acid Chemical compound CCCCCCCCCCCCCCC\C=C\C(O)=O LKOVPWSSZFDYPG-WUKNDPDISA-N 0.000 description 1
ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
RUDFQVOCFDJEEF-UHFFFAOYSA-N yttrium(III) oxide Inorganic materials [O-2].[O-2].[O-2].[Y+3].[Y+3] RUDFQVOCFDJEEF-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of rare earths
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- B01J37/0203—Impregnation the impregnation liquid containing organic compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP7511104A 1993-10-22 1994-10-21 アルコキシル化の方法 Pending JPH09504011A (ja)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
AU1954		1988-12-14
AUPM195593		1993-10-22
AUPM195493		1993-10-22
PCT/AU1994/000645 WO1995011212A1 (en)	1993-10-22	1994-10-21	Alkoxylation process
AU1955		1998-04-16

Publications (1)

Publication Number	Publication Date
JPH09504011A true JPH09504011A (ja)	1997-04-22

Family

ID=25644560

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP7511104A Pending JPH09504011A (ja)	1993-10-22	1994-10-21	アルコキシル化の方法

Country Status (6)

Country	Link
EP (1)	EP0733032A4 (de)
JP (1)	JPH09504011A (de)
BR (1)	BR9407875A (de)
CA (1)	CA2174238A1 (de)
WO (1)	WO1995011212A1 (de)
ZA (1)	ZA948255B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SA111320500B1 (ar)	2010-06-04	2015-06-17	داو جلوبال تكنولوجيز ال ال سي	معلقات لاستعادة محسنة للزيت
CA3228918A1 (en)	2021-08-10	2023-02-16	Nippon Shokubai Co., Ltd.	Polyalkylene-oxide-containing compound
CN117244566B (zh) *	2023-11-16	2024-02-09	内蒙古工业大学	一种光催化剂1T/2H MoSe2/ZIS及其制备方法

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1246617A (en) *	1982-09-30	1988-12-13	John H. Robson	Process for the production of alkylene glycols
US4665236A (en) *	1984-10-29	1987-05-12	Shell Oil Company	Alkoxylation process using bimetallic oxo catalyst
US5114900A (en) *	1988-09-30	1992-05-19	Union Carbide Chemicals & Plastics Technology Corporation	Alkoxylation using modified calcium-containing bimetallic or polymetallic catalysts
US5112788A (en) *	1988-09-30	1992-05-12	Union Carbide Chemicals & Plastics Technology Corporation	Alkoxylation using modified group iia metal-containing bimetallic or polymetallic catalysts
US5120697A (en) *	1988-09-30	1992-06-09	Union Carbide Chemicals & Plastics Technology Corporation	Alkoxylation using modified calcium-containing catalysts
US5112789A (en) *	1988-09-30	1992-05-12	Union Carbide Chemicals & Plastics Technology Corporation	Alkoxylation catalysis
US5118650A (en) *	1988-09-30	1992-06-02	Union Carbide Chemicals & Plastics Technology Corporation	Alkoxylation using modified group iiib metal-containing bimetallic or polymetallic catalysts
CA2008717A1 (en) *	1989-02-10	1990-08-10	Herman R. Jackson	Solid fumaric acid-solid barium chromate catalyst for removing impurities and residual moisture and method for its use
US5104987A (en) *	1990-09-20	1992-04-14	Union Carbide Chemicals & Plastics Technology Corporation	Alkoxylation of active hydrogen-containing compounds
US5164497A (en) *	1990-09-20	1992-11-17	Union Carbide Chemicals & Plastics Technology Corporation	Decarboxylation processes using mixed metal oxide catalysts
WO1993022266A1 (en) *	1992-04-24	1993-11-11	Ici Australia Operations Proprietary Limited	Alkoxylation process

1994
- 1994-10-20 ZA ZA948255A patent/ZA948255B/xx unknown
- 1994-10-21 WO PCT/AU1994/000645 patent/WO1995011212A1/en not_active Ceased
- 1994-10-21 CA CA002174238A patent/CA2174238A1/en not_active Abandoned
- 1994-10-21 BR BR9407875A patent/BR9407875A/pt not_active Application Discontinuation
- 1994-10-21 JP JP7511104A patent/JPH09504011A/ja active Pending
- 1994-10-21 EP EP94930870A patent/EP0733032A4/de not_active Withdrawn

Also Published As

Publication number	Publication date
CA2174238A1 (en)	1995-04-27
EP0733032A4 (de)	1998-01-21
EP0733032A1 (de)	1996-09-25
WO1995011212A1 (en)	1995-04-27
ZA948255B (en)	1995-06-19
BR9407875A (pt)	1996-10-29

Publication	Publication Date	Title
US5104987A (en)	1992-04-14	Alkoxylation of active hydrogen-containing compounds
US4665236A (en)	1987-05-12	Alkoxylation process using bimetallic oxo catalyst
CN88102512A (zh)	1988-11-23	使用钙基催化剂的烷氧基化法
CN1976887A (zh)	2007-06-06	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
CA1260018A (en)	1989-09-26	Alkoxylation process using bimetallic oxo catalyst
KR20090110917A (ko)	2009-10-23	혼합 산화금속 촉매를 사용한 프로판 및 이소부탄의 가암모니아 산화 방법
CN101489973A (zh)	2009-07-22	制备α-羟基羧酸的方法
KR0133654B1 (ko)	1998-04-21	아미노에테르의 제조방법
US5844115A (en)	1998-12-01	Alkoxylation process
JP2753883B2 (ja)	1998-05-20	燐酸バリウムを触媒とするアルコキシル化方法
JPH09504011A (ja)	1997-04-22	アルコキシル化の方法
JP2003300926A (ja)	2003-10-21	α−ヒドロキシカルボン酸又はα−オキソカルボン酸の製造方法
CN101535230B (zh)	2012-05-30	环氧烷烃加成物的制造方法
CN1289192C (zh)	2006-12-13	制备流体稀土烷氧基化催化剂的方法
AU700707B2 (en)	1999-01-14	Alkoxylation process
US6953766B2 (en)	2005-10-11	Preparation of efficient REPO and LAPO catalysts
JPH06279396A (ja)	1994-10-04	チオール基含有カルボン酸エステル類の製造方法
RU2451548C2 (ru)	2012-05-27	Способ окислительного аммонолиза пропана и изобутана в присутствии смешанных металлоксидных катализаторов
CN101193700B (zh)	2011-12-14	通过选择性醚分解制备醇的方法
AU662980B2 (en)	1995-09-21	Alkoxylation process
JP2890322B2 (ja)	1999-05-10	改質した▲ｉｉｉ▼ｂ族金属含有バイメタル又はポリメタル触媒を使用するアルコキシル化方法
JPH02160624A (ja)	1990-06-20	モリブデンの炭化水素可溶塩
JPH11319556A (ja)	1999-11-24	アルキレンオキサイド付加触媒
JPH03229643A (ja)	1991-10-11	改質した２ａ族金属含有バイメタルまたはポリメタル触媒を使用するアルコキシル化方法