JP2012526787A - カルボニル化プロセス - Google Patents
カルボニル化プロセス Download PDFInfo
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- JP2012526787A JP2012526787A JP2012510355A JP2012510355A JP2012526787A JP 2012526787 A JP2012526787 A JP 2012526787A JP 2012510355 A JP2012510355 A JP 2012510355A JP 2012510355 A JP2012510355 A JP 2012510355A JP 2012526787 A JP2012526787 A JP 2012526787A
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- mordenite
- catalyst
- ammonium hydroxide
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- silica
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- 238000000034 method Methods 0.000 title claims abstract description 70
- 238000005810 carbonylation reaction Methods 0.000 title claims abstract description 39
- 230000006315 carbonylation Effects 0.000 title claims abstract description 28
- 229910052680 mordenite Inorganic materials 0.000 claims abstract description 89
- 239000003054 catalyst Substances 0.000 claims abstract description 76
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 49
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 39
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 34
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000000908 ammonium hydroxide Substances 0.000 claims abstract description 32
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims abstract description 24
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000000376 reactant Substances 0.000 claims abstract description 19
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 19
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 36
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 21
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 21
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 21
- 239000011230 binding agent Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 230000003197 catalytic effect Effects 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052809 inorganic oxide Inorganic materials 0.000 claims description 11
- 229910021529 ammonia Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000391 magnesium silicate Substances 0.000 claims description 2
- 229910052919 magnesium silicate Inorganic materials 0.000 claims description 2
- 235000019792 magnesium silicate Nutrition 0.000 claims description 2
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 235000011114 ammonium hydroxide Nutrition 0.000 description 28
- 239000000243 solution Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000007789 gas Substances 0.000 description 13
- 239000010457 zeolite Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 229910021536 Zeolite Inorganic materials 0.000 description 9
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000001354 calcination Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 229910052593 corundum Inorganic materials 0.000 description 6
- 239000010431 corundum Substances 0.000 description 6
- -1 alkyl aromatic hydrocarbons Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000010304 firing Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- ZZBAGJPKGRJIJH-UHFFFAOYSA-N 7h-purine-2-carbaldehyde Chemical compound O=CC1=NC=C2NC=NC2=N1 ZZBAGJPKGRJIJH-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004517 catalytic hydrocracking Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000005269 aluminizing Methods 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000011959 amorphous silica alumina Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 229910001593 boehmite Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- ZADYMNAVLSWLEQ-UHFFFAOYSA-N magnesium;oxygen(2-);silicon(4+) Chemical compound [O-2].[O-2].[O-2].[Mg+2].[Si+4] ZADYMNAVLSWLEQ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000010334 sieve classification Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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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
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/18—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type
-
- 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
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
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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
- B01J35/61—Surface area
- B01J35/615—100-500 m2/g
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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
- B01J35/63—Pore volume
- B01J35/633—Pore volume less than 0.5 ml/g
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- B01J35/635—0.5-1.0 ml/g
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- C07C67/37—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by reaction of ethers with carbon monoxide
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Abstract
【選択図】図1
Description
触媒A
触媒Aは、BASF社製のシリカ:アルミナ比が40.5のH−モルデナイトである。
アルカリ溶液(1.5LのNaOH水溶液、0.2M)を激しく撹拌しながら65℃に加熱した。系が平衡に達した後、50gの触媒Aを添加し、30分間連続撹拌した。30分後、撹拌しながら氷冷した水中で懸濁液を冷却した。次いで、混合物を減圧下でろ過し、3リットルの脱イオン水で洗浄し、空気乾燥器中で110℃にて一晩乾燥させた。この塩基処理されたモルデナイトを、NH4NO3水溶液(モルデナイト1g当たり10ml、1M)を用いて80℃で1時間交換した。交換は3回行った。各交換ステップ後に、NH4−モルデナイトを脱イオン水で洗浄した。湿潤NH4−モルデナイトを110℃で乾燥させ、その後、以下の焼成法Iを用いてH型のモルデナイトに変換した。
100mlのステンレス鋼オートクレーブ中で5gの担持触媒Aにアンモニア溶液(90mlのNH3水溶液、25wt%、pH13.5)を添加した。次いで、オートクレーブを密封し、ロータリーオーブン中で温度85℃に8時間維持した。氷冷した水中でオートクレーブを冷却し、懸濁液を減圧下でろ過し、0.5Lの脱イオン水で洗浄し、110℃で乾燥させた。得られたNH4−モルデナイトを焼成法Iを用いて焼成してH型のモルデナイトを得た。
焼成は、静止空気下で、モルデナイトを3℃/分で90℃に加熱して2時間維持し、1℃/分で110℃に加熱して2時間維持し、3℃/分で500℃に加熱して3時間維持した後、室温に冷却することにより行った。
触媒A〜Cの特定の物理化学的特性を表1に示す。
触媒A〜Cのそれぞれを用いて一連のカルボニル化反応を行った。
以下のように触媒Aをアルミナバインダーと組み合わせることで触媒Dを調製した。30gの触媒A及び15gのアルミナ(サソール社(Sasol)製、Pural SCF)をビュッヒ社製の粉末乾燥フラスコ中で一緒に穏やかにミリングして自由流動粉末(free flowing powder)を生成した。周囲温度、周囲圧力でローターエバポレーターを用いて速度100rpmにて1時間粉末をブレンドし、その後、静止空気雰囲気下で500℃にて3時間焼成した。
上記の触媒Dに記載した方法に従って、20gの触媒Cを10gのアルミナバインダー(サソール社製、Pural SCF)と組み合わせることで触媒Eを調製した。
触媒D及び触媒Eを用いて、一酸化炭素によるジメチルエーテルのカルボニル化反応を行った。
Claims (15)
- 酢酸及び酢酸メチルから選択される少なくとも1つのカルボニル化生成物を製造するプロセスであって、メタノール及びその反応性誘導体から選択される少なくとも1つのカルボニル化可能な反応物質を触媒存在下で一酸化炭素を用いてカルボニル化することを含み、前記触媒が、水酸化アンモニウム水溶液で処理されたシリカ:アルミナのモル比が少なくとも10:1のモルデナイトである、プロセス。
- 前記触媒のシリカ:アルミナのモル比が25〜60:1である、請求項1に記載のプロセス。
- 前記触媒が、水酸化アンモニウム水溶液を用いた処理前に脱アルミニウムされたモルデナイトである、請求項1又は2に記載のプロセス。
- 前記触媒が、アンモニア濃度が15〜25重量%の水酸化アンモニウム水溶液で処理されたモルデナイトである、請求項1〜3のいずれか一項に記載のプロセス。
- 前記触媒が、温度70〜100℃で水酸化アンモニウム水溶液を用いて処理されたモルデナイトである、請求項1〜4のいずれか一項に記載のプロセス。
- 前記触媒がH−モルデナイトである、請求項1〜5のいずれか一項に記載のプロセス。
- 前記触媒がバインダーと組み合わされている、請求項1〜6のいずれか一項に記載のプロセス。
- 前記バインダーが耐熱無機酸化物である、請求項6に記載のプロセス。
- 前記耐熱無機酸化物が、シリカ、アルミナ、シリカ−アルミナ、ケイ酸マグネシウム、及びケイ酸マグネシウムアルミニウムの少なくとも1つからなる群から選択される、請求項8に記載のプロセス。
- 前記バインダーのメソ多孔度が1〜500m2/gである、請求項7〜9のいずれか一項に記載のプロセス。
- 前記カルボニル化可能な反応物質が、ジメチルエーテルである反応性誘導体である、請求項1〜10のいずれか一項に記載のプロセス。
- 前記カルボニル化可能な反応物質のフィード中に、前記フィード中のジメチルエーテルの量に対して2.5wt%未満の量で水が存在する、請求項12に記載のプロセス。
- 前記プロセスが水素存在下で行われる、請求項1〜12のいずれか一項に記載のプロセス。
- 前記カルボニル化生成物が酢酸メチルであり、前記酢酸メチルの少なくとも一部が酢酸へと加水分解される、請求項1〜13のいずれか一項に記載のプロセス。
- 酢酸及び酢酸メチルから選択される少なくとも1つのカルボニル化生成物を製造するプロセスにおける触媒活性を向上させるために水酸化アンモニウム水溶液で処理されたシリカ:アルミナ比が少なくとも10:1のモルデナイトである触媒の使用であって、前記プロセスが、メタノール及びその反応性誘導体から選択される少なくとも1つのカルボニル化可能な反応物質を一酸化炭素でカルボニル化することを含む、使用。
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EP09251310A EP2251082A1 (en) | 2009-05-14 | 2009-05-14 | Carbonylation catalyst and process |
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PCT/GB2010/000917 WO2010130973A2 (en) | 2009-05-14 | 2010-05-06 | Carbonylation process |
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KR20150102973A (ko) * | 2014-01-28 | 2015-09-09 | 달리안 인스티튜트 오브 케미컬 피직스, 차이니즈 아카데미 오브 사이언시즈 | 메틸아세테이트의 제조 방법 |
JP2016515039A (ja) * | 2013-03-08 | 2016-05-26 | ビーピー ケミカルズ リミテッドBp Chemicals Limited | カルボニル化触媒およびプロセス |
JP2020532480A (ja) * | 2017-07-28 | 2020-11-12 | サウジ アラビアン オイル カンパニーSaudi Arabian Oil Company | 階層的メソ細孔性ゼオライトベータの生成方法 |
WO2023063244A1 (ja) * | 2021-10-11 | 2023-04-20 | 株式会社レゾナック | 固体触媒、固体触媒の製造方法、モノメチルアミンの製造方法 |
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EP2251314A1 (en) * | 2009-05-14 | 2010-11-17 | BP Chemicals Limited | Carbonylation process |
KR20140127263A (ko) * | 2012-02-23 | 2014-11-03 | 비피 케미칼즈 리미티드 | 아세트산 및 디메틸 에테르의 제조를 위한 촉매 및 방법 |
CN106518657B (zh) * | 2015-09-11 | 2019-03-29 | 中国科学院大连化学物理研究所 | 一种通过甲醇羰基化制备乙酸的方法 |
GB201705882D0 (en) | 2017-04-12 | 2017-05-24 | Bp Chem Int Ltd | Process |
CN109092348B (zh) * | 2017-06-20 | 2020-12-25 | 天津大学 | 丝光沸石分子筛催化剂及其制备方法与其在羰基化合成醋酸甲酯中的应用 |
CN111790452B (zh) * | 2019-04-09 | 2021-11-23 | 中国科学院大连化学物理研究所 | 一种甲醇羰基化催化剂及其制备方法、应用 |
CN113244952A (zh) * | 2021-04-27 | 2021-08-13 | 中国矿业大学 | 一种同时提高二甲醚羰基化的hmor分子筛催化剂活性和寿命的改性方法 |
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WO2010130973A3 (en) | 2011-03-31 |
BRPI1012134A2 (pt) | 2016-03-29 |
RU2011150626A (ru) | 2013-06-20 |
JP5676573B2 (ja) | 2015-02-25 |
CA2760654A1 (en) | 2010-11-18 |
ES2445528T3 (es) | 2014-03-03 |
EP2429703B1 (en) | 2013-11-06 |
US8692015B2 (en) | 2014-04-08 |
EP2251082A1 (en) | 2010-11-17 |
SG175444A1 (en) | 2011-12-29 |
WO2010130973A2 (en) | 2010-11-18 |
KR20120020120A (ko) | 2012-03-07 |
UA103243C2 (uk) | 2013-09-25 |
US20120053360A1 (en) | 2012-03-01 |
RU2528339C2 (ru) | 2014-09-10 |
CN102438747B (zh) | 2014-05-28 |
EP2429703A2 (en) | 2012-03-21 |
CN102438747A (zh) | 2012-05-02 |
MY155691A (en) | 2015-11-13 |
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