KR100593766B1 - 불포화 산 또는 그의 에스테르의 제조 및 그를 위한 촉매 - Google Patents
불포화 산 또는 그의 에스테르의 제조 및 그를 위한 촉매 Download PDFInfo
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- KR100593766B1 KR100593766B1 KR1020007011182A KR20007011182A KR100593766B1 KR 100593766 B1 KR100593766 B1 KR 100593766B1 KR 1020007011182 A KR1020007011182 A KR 1020007011182A KR 20007011182 A KR20007011182 A KR 20007011182A KR 100593766 B1 KR100593766 B1 KR 100593766B1
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- catalyst
- silica
- surface area
- compound
- modifier element
- Prior art date
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- Expired - Lifetime
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- 239000003054 catalyst Substances 0.000 title claims abstract description 113
- 239000002253 acid Substances 0.000 title claims abstract description 23
- 150000002148 esters Chemical class 0.000 title claims abstract description 22
- 150000007513 acids Chemical class 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 176
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 86
- 239000003607 modifier Substances 0.000 claims abstract description 49
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000011148 porous material Substances 0.000 claims abstract description 27
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 27
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 22
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 22
- 229910052792 caesium Inorganic materials 0.000 claims abstract description 21
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052735 hafnium Inorganic materials 0.000 claims abstract description 9
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229940017219 methyl propionate Drugs 0.000 claims abstract description 9
- 229910052751 metal Inorganic materials 0.000 claims abstract description 8
- 239000002184 metal Substances 0.000 claims abstract description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 6
- 239000011777 magnesium Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 73
- 238000000034 method Methods 0.000 claims description 30
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 16
- 238000001035 drying Methods 0.000 claims description 13
- 239000002245 particle Substances 0.000 claims description 11
- 238000005470 impregnation Methods 0.000 claims description 10
- -1 silicon halide Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000011800 void material Substances 0.000 claims description 2
- 150000003755 zirconium compounds Chemical class 0.000 claims 2
- 150000004679 hydroxides Chemical class 0.000 claims 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052796 boron Inorganic materials 0.000 abstract description 8
- 238000006555 catalytic reaction Methods 0.000 abstract description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract description 4
- 150000002739 metals Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 description 28
- 230000000052 comparative effect Effects 0.000 description 27
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 26
- 238000012360 testing method Methods 0.000 description 23
- 230000000694 effects Effects 0.000 description 18
- OERNJTNJEZOPIA-UHFFFAOYSA-N zirconium nitrate Chemical compound [Zr+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O OERNJTNJEZOPIA-UHFFFAOYSA-N 0.000 description 18
- 235000019256 formaldehyde Nutrition 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 12
- 230000014759 maintenance of location Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229910021485 fumed silica Inorganic materials 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- NLSCHDZTHVNDCP-UHFFFAOYSA-N caesium nitrate Chemical compound [Cs+].[O-][N+]([O-])=O NLSCHDZTHVNDCP-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 238000005245 sintering Methods 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 238000001354 calcination Methods 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229910052746 lanthanum Inorganic materials 0.000 description 3
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- 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 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 241000588731 Hafnia Species 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- 229910052810 boron oxide Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- CJNBYAVZURUTKZ-UHFFFAOYSA-N hafnium(IV) oxide Inorganic materials O=[Hf]=O CJNBYAVZURUTKZ-UHFFFAOYSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- DUFCMRCMPHIFTR-UHFFFAOYSA-N 5-(dimethylsulfamoyl)-2-methylfuran-3-carboxylic acid Chemical compound CN(C)S(=O)(=O)C1=CC(C(O)=O)=C(C)O1 DUFCMRCMPHIFTR-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000605112 Scapanulus oweni Species 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000012615 aggregate Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002506 iron compounds Chemical class 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 238000002459 porosimetry Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
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- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/12—Silica and alumina
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/08—Silica
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- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/14—Silica and magnesia
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- 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
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
- B01J23/04—Alkali metals
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/28—Molybdenum
-
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/88—Molybdenum
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
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- 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
- B01J37/0207—Pretreatment of the support
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/613—10-100 m2/g
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- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/615—100-500 m2/g
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/64—Pore diameter
- B01J35/647—2-50 nm
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/64—Pore diameter
- B01J35/651—50-500 nm
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020067001265A KR100592857B1 (ko) | 1998-04-08 | 1999-04-01 | 불포화 산 또는 그의 에스테르의 제조 및 그를 위한 촉매 |
| KR1020067001266A KR100651106B1 (ko) | 1998-04-08 | 1999-04-01 | 불포화 산 또는 그의 에스테르의 제조 및 그를 위한 촉매 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9807498.2A GB9807498D0 (en) | 1998-04-08 | 1998-04-08 | Production of unsaturated acids therfore and catalysts therfor |
| GB9807498.2 | 1998-04-08 | ||
| PCT/GB1999/001029 WO1999052628A1 (en) | 1998-04-08 | 1999-04-01 | Production of unsaturated acids or esters thereof and catalysts therefor |
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| KR1020067001266A Division KR100651106B1 (ko) | 1998-04-08 | 1999-04-01 | 불포화 산 또는 그의 에스테르의 제조 및 그를 위한 촉매 |
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| KR1020067001265A Expired - Lifetime KR100592857B1 (ko) | 1998-04-08 | 1999-04-01 | 불포화 산 또는 그의 에스테르의 제조 및 그를 위한 촉매 |
| KR1020067001266A Expired - Lifetime KR100651106B1 (ko) | 1998-04-08 | 1999-04-01 | 불포화 산 또는 그의 에스테르의 제조 및 그를 위한 촉매 |
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| KR1020067001265A Expired - Lifetime KR100592857B1 (ko) | 1998-04-08 | 1999-04-01 | 불포화 산 또는 그의 에스테르의 제조 및 그를 위한 촉매 |
| KR1020067001266A Expired - Lifetime KR100651106B1 (ko) | 1998-04-08 | 1999-04-01 | 불포화 산 또는 그의 에스테르의 제조 및 그를 위한 촉매 |
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| EP (3) | EP1073517B1 (enExample) |
| JP (2) | JP2002511336A (enExample) |
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| CA (1) | CA2326778C (enExample) |
| CZ (2) | CZ302025B6 (enExample) |
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| RU (1) | RU2203731C2 (enExample) |
| TW (1) | TW408032B (enExample) |
| WO (1) | WO1999052628A1 (enExample) |
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| EP1240943A1 (en) * | 2000-10-21 | 2002-09-18 | Degussa AG | Catalyst support |
| US6887822B2 (en) | 2001-09-25 | 2005-05-03 | Pq Corporation | Method for making silica supported, crush-resistant catalysts |
| US20040006244A1 (en) * | 2002-05-22 | 2004-01-08 | Manzer Leo Ernest | Process for making ethyencially unsaturated acids and acids |
| US7094730B2 (en) * | 2002-10-31 | 2006-08-22 | Delphi Technologies, Inc. | Gas treatment device, methods for making and using the same, and a vehicle exhaust system |
| JP4497457B2 (ja) * | 2003-06-03 | 2010-07-07 | 三菱レイヨン株式会社 | メタクリル酸エステル製造用触媒の製造方法 |
| US7139226B2 (en) * | 2004-02-25 | 2006-11-21 | Brady Worldwide, Inc. | Long term rapid color changing time indicator |
| US7983896B2 (en) | 2004-03-05 | 2011-07-19 | SDL Language Technology | In-context exact (ICE) matching |
| JP4497459B2 (ja) * | 2004-06-08 | 2010-07-07 | 三菱レイヨン株式会社 | メタクリル酸エステルの製造方法 |
| US7141682B2 (en) | 2004-07-27 | 2006-11-28 | E. I. Du Pont De Nemours And Company | Liquid phase synthesis of methylene lactones using oxnitride catalyst |
| US7151185B2 (en) | 2004-07-27 | 2006-12-19 | E. I. Du Pont De Nemours And Company | Gas phase synthesis of methylene lactones using oxynitride catalyst |
| US7153981B2 (en) | 2004-07-27 | 2006-12-26 | E. I. Du Pont De Nemours And Company | Supercritical fluid phase synthesis of methylene lactones using oxynitride catalyst |
| US10352484B2 (en) * | 2004-08-05 | 2019-07-16 | Faurecia Emissions Control Technologies Germany Gmbh | Exhaust system |
| US7348442B2 (en) | 2004-10-18 | 2008-03-25 | E. I. Du Pont De Nemours And Company | Gas phase synthesis of methylene lactones using catalysts derived from hydrotalcite precursors |
| JP4895251B2 (ja) * | 2005-06-15 | 2012-03-14 | 三菱レイヨン株式会社 | メタクリル酸エステル製造用触媒の製造方法 |
| DE102007025223A1 (de) | 2007-05-31 | 2008-12-04 | Süd-Chemie AG | Zirkoniumoxid-dotierter VAM-Schalenkatalysator, Verfahren zu dessen Herstellung sowie dessen Verwendung |
| DE102007025442B4 (de) | 2007-05-31 | 2023-03-02 | Clariant International Ltd. | Verwendung einer Vorrichtung zur Herstellung eines Schalenkatalysators und Schalenkatalysator |
| DE102007025443A1 (de) * | 2007-05-31 | 2008-12-04 | Süd-Chemie AG | Pd/Au-Schalenkatalysator enthaltend HfO2, Verfahren zu dessen Herstellung sowie dessen Verwendung |
| DE102007025362A1 (de) | 2007-05-31 | 2008-12-11 | Süd-Chemie AG | Dotierter Pd/Au-Schalenkatalysator, Verfahren zu dessen Herstellung sowie dessen Verwendung |
| RU2010103800A (ru) * | 2007-07-05 | 2011-08-10 | Грейс Гмбх Унд Ко. Кг (De) | Способ приготовления катализаторов на носителях из неорганических оксидов |
| GB0809332D0 (en) * | 2008-05-22 | 2008-07-02 | Lucite Int Uk Ltd | Production of ethylenically unsaturated acids or esters thereof |
| DE102008059341A1 (de) | 2008-11-30 | 2010-06-10 | Süd-Chemie AG | Katalysatorträger, Verfahren zu seiner Herstellung sowie Verwendung |
| ES2790897T3 (es) | 2008-12-18 | 2020-10-29 | Lucite Int Uk Ltd | Un procedimiento de purificación de metacrilato de metilo |
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| CN101829558B (zh) * | 2010-04-27 | 2012-02-22 | 中国科学院过程工程研究所 | 一种由丙酸甲酯与甲醛反应直接制取甲基丙烯酸甲酯的催化剂及其制备方法 |
| GB201011091D0 (en) * | 2010-07-01 | 2010-08-18 | Lucite Int Uk Ltd | A catalyst and a process for the production of ethylenically unsaturated carboxylic acids or esters |
| US8652988B2 (en) | 2011-04-27 | 2014-02-18 | Celanese International Corporation | Catalyst for producing acrylic acids and acrylates |
| US8658822B2 (en) * | 2011-10-03 | 2014-02-25 | Celanese International Corporation | Processes for producing acrylic acids and acrylates |
| US8729299B2 (en) | 2011-10-03 | 2014-05-20 | Celanese International Corporation | Processes for the production of acrylic acids and acrylates |
| GB201200551D0 (en) * | 2012-01-13 | 2012-02-29 | Lucite Int Uk Ltd | A process for the production of ethylenically unsaturated carboxylic acids or esters and a catalyst therefor |
| EP2825307A1 (en) | 2012-03-13 | 2015-01-21 | Celanese International Corporation | Catalyst for producing acrylic acids and acrylates comprising vanadium, titanium and tungsten |
| CN104271236B (zh) | 2012-03-13 | 2018-01-26 | 国际人造丝公司 | 用于产生丙烯酸和丙烯酸类的包含钒、铋和钨的催化剂 |
| WO2013137934A1 (en) | 2012-03-13 | 2013-09-19 | Celanese International Corporation | Catalyst for producing acrylic acids and acrylates |
| KR101402957B1 (ko) * | 2012-05-21 | 2014-06-02 | 서울대학교산학협력단 | 균일한 중형 기공을 갖는 복합 산화물 촉매, 그 제조 방법 및 상기 촉매를 이용하여 에스테르 화합물을 제조하는 방법 |
| US9199910B2 (en) | 2012-06-04 | 2015-12-01 | Rohm And Haas Company | Process for production of methacrylic acid esters |
| CN102775302B (zh) * | 2012-08-03 | 2015-09-02 | 旭阳化学技术研究院有限公司 | 一种由丙酸甲酯和甲醛制备甲基丙烯酸甲酯的方法 |
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| CN102941113B (zh) * | 2012-11-28 | 2014-12-10 | 西南化工研究设计院有限公司 | 醋酸甲酯与甲缩醛合成丙烯酸甲酯的催化剂及其制备方法 |
| CN102962052B (zh) * | 2012-11-30 | 2014-10-29 | 西南化工研究设计院有限公司 | 一种醋酸和多聚甲醛合成丙烯酸的催化剂及其制备和应用 |
| US9073846B2 (en) | 2013-06-05 | 2015-07-07 | Celanese International Corporation | Integrated process for the production of acrylic acids and acrylates |
| BR112015031389B1 (pt) * | 2013-06-26 | 2021-01-26 | Rohm And Haas Company | processo para produzir ésteres de ácido metacrílico |
| US9120743B2 (en) | 2013-06-27 | 2015-09-01 | Celanese International Corporation | Integrated process for the production of acrylic acids and acrylates |
| CN104525176B (zh) * | 2014-12-16 | 2017-05-17 | 旭阳化学技术研究院有限公司 | Cs基催化剂微球的制备方法、由其制备的微球和用该微球合成（甲基）丙烯酸甲酯的方法 |
| WO2016127054A2 (en) * | 2015-02-06 | 2016-08-11 | Wisconsin Alumni Research Foundation | Enhanced dispersion of two-dimensional metal oxide surface species on silica using an alkali promoter |
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| CN108101770B (zh) * | 2016-11-25 | 2020-05-05 | 中国科学院大连化学物理研究所 | 一种再生制备不饱和酸或不饱和酸酯的催化剂的方法 |
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| WO2020226905A1 (en) * | 2019-05-06 | 2020-11-12 | W. R. Grace & Co.-Conn. | Using silica-zirconia catalysts in processes to reduce glycidol, glycidyl esters, or both glycidol and glycidyl esters |
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| US11806694B2 (en) | 2020-03-12 | 2023-11-07 | Mitsubishi Chemical UK Limited | Catalyst and a process for the production of ethylenically unsaturated carboxylic acids or esters |
| CN112844356A (zh) * | 2021-02-02 | 2021-05-28 | 中国科学院过程工程研究所 | 一种合成甲基丙烯酸甲酯的催化剂及其应用方法 |
| CN112774658A (zh) * | 2021-02-02 | 2021-05-11 | 中国科学院过程工程研究所 | 一种由乙酸甲酯和甲醛合成丙烯酸甲酯的酸碱双功能催化剂及制备方法 |
| BR112023024810A2 (pt) | 2021-06-01 | 2024-02-15 | Mitsubishi Chem Corp | Catalisador, método para produção de catalisador, e método para produção de ácido carboxílico insaturado e/ou éster de ácido carboxílico insaturado |
| CN119793495B (zh) * | 2023-10-09 | 2025-10-31 | 中国石油化工股份有限公司 | 醋酸甲酯与甲醛缩合制备丙烯酸甲酯用催化剂及其制备方法以及丙烯酸甲酯的制备方法 |
| CN117654466B (zh) * | 2024-02-01 | 2024-04-23 | 浙江新和成股份有限公司 | 催化剂及其制备方法、烯属不饱和酸或其酯的制备方法 |
| CN118324635B (zh) * | 2024-06-13 | 2024-08-13 | 深圳市普利凯新材料股份有限公司 | 一种3-乙氧基丙烯酸乙酯的合成方法 |
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- 1998-04-08 GB GBGB9807498.2A patent/GB9807498D0/en not_active Ceased
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1999
- 1999-04-01 KR KR1020007011182A patent/KR100593766B1/ko not_active Expired - Lifetime
- 1999-04-01 EP EP19990913512 patent/EP1073517B1/en not_active Expired - Lifetime
- 1999-04-01 JP JP2000543233A patent/JP2002511336A/ja not_active Withdrawn
- 1999-04-01 DE DE69912113T patent/DE69912113T2/de not_active Expired - Lifetime
- 1999-04-01 WO PCT/GB1999/001029 patent/WO1999052628A1/en not_active Ceased
- 1999-04-01 PL PL343349A patent/PL212115B1/pl unknown
- 1999-04-01 ES ES01119422T patent/ES2250276T3/es not_active Expired - Lifetime
- 1999-04-01 KR KR1020067001265A patent/KR100592857B1/ko not_active Expired - Lifetime
- 1999-04-01 CN CNB99805643XA patent/CN1154537C/zh not_active Expired - Lifetime
- 1999-04-01 AU AU31623/99A patent/AU750405C/en not_active Expired
- 1999-04-01 CA CA002326778A patent/CA2326778C/en not_active Expired - Lifetime
- 1999-04-01 US US09/647,876 patent/US6544924B1/en not_active Expired - Lifetime
- 1999-04-01 DE DE69927853T patent/DE69927853T2/de not_active Expired - Lifetime
- 1999-04-01 ES ES99913512T patent/ES2209416T3/es not_active Expired - Lifetime
- 1999-04-01 DE DE69927857T patent/DE69927857T2/de not_active Expired - Lifetime
- 1999-04-01 PL PL383560A patent/PL206387B1/pl unknown
- 1999-04-01 CZ CZ20003639A patent/CZ302025B6/cs not_active IP Right Cessation
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3933888A (en) * | 1972-10-06 | 1976-01-20 | Rohm And Haas Company | Production of unsaturated acids, esters and nitriles, and catalyst therefor |
| US4845070A (en) * | 1984-07-18 | 1989-07-04 | Amoco Corporation | Catalyst for producing alpha, beta-ethylenically unsaturated aliphatic monocarboxylic acid and method of making said catalyst |
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