JP2022553799A - チタン化触媒、チタン化触媒を調製する方法、及びエポキシ化の方法 - Google Patents
チタン化触媒、チタン化触媒を調製する方法、及びエポキシ化の方法 Download PDFInfo
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- 239000000377 silicon dioxide Substances 0.000 claims abstract description 198
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 42
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- KZCYIWWNWWRLBQ-UHFFFAOYSA-P diazanium 3-methanidylbutan-2-one titanium(2+) dihydrate Chemical compound [NH4+].[NH4+].O.O.[Ti++].CC([CH2-])C([CH2-])=O.CC([CH2-])C([CH2-])=O KZCYIWWNWWRLBQ-UHFFFAOYSA-P 0.000 claims description 21
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
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- 239000012298 atmosphere Substances 0.000 description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 description 2
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- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 2
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- 238000001179 sorption measurement Methods 0.000 description 2
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- 238000004846 x-ray emission Methods 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 description 1
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- 102220500397 Neutral and basic amino acid transport protein rBAT_M41T_mutation Human genes 0.000 description 1
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- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
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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
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/063—Titanium; Oxides or hydroxides thereof
-
- 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
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/08—Silica
-
- 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
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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
- B01J37/0203—Impregnation the impregnation liquid containing organic compounds
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
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- 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
- B01J37/08—Heat treatment
- B01J37/082—Decomposition and pyrolysis
- B01J37/088—Decomposition of a metal salt
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/19—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic hydroperoxides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
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- C08F8/00—Chemical modification by after-treatment
- C08F8/08—Epoxidation
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Abstract
Description
本出願は、特許協力条約に基づいて出願され、2019年11月4日に出願された米国仮出願第62/930,281号に対する優先権の利益を主張し、その全文は参考として本明細書に組み込まれる。
チタン化シリカ触媒を調製する方法
R3SiNHSiR’3
(式中、各R及びR’は独立に、C1~C6ヒドロカルビルから選択される)のオルガノジシラザンである。いくつかの実施形態では、シリル化剤はヘキサメチルジシラザンを含む。
シリカ担体
チタン(IV)ビス(アンモニウムラクタト)ジヒドロキシド
水溶性有機化合物
エポキシ化の方法
実施例1-チタン化シリカ触媒のエポキシ化性能
Claims (20)
- チタン化シリカ触媒を調製する方法であって、
(i)水溶性有機化合物と(ii)水溶性チタン化合物とを含む液体を用意すること;及び
シリカ担体を前記液体に接触させて前記水溶性チタン化合物の少なくとも一部分を前記シリカ担体上に沈着させて、チタン処理済みシリカ担体を形成することを含む、方法。 - 前記水溶性有機化合物が、C1~C4ヒドロカルビルと、ヒドロキシル、アミン、カルボン酸、エステル、エーテル、ケトン、及びアルデヒドからなる群から選択される少なくとも1種の官能基とを含む、請求項1に記載の方法。
- 前記水溶性チタン化合物がチタン(IV)ビス(アンモニウムラクタト)ジヒドロキシドである、請求項1に記載の方法。
- 前記水溶性有機化合物が、一価アルコール又はポリヒドロキシアルコールである、請求項1に記載の方法。
- 前記水溶性有機化合物が、エチレングリコール又はプロピレングリコールを含む、請求項2に記載の方法。
- 前記水溶性有機化合物が、メタノール、エタノール、又はそれらの組み合わせを含む、請求項2に記載の方法。
- 前記チタン(IV)ビス(アンモニウムラクタト)ジヒドロキシドが、前記液体の重量に基づいて約5重量%~約70重量%の量で前記液体中に存在する、請求項3に記載の方法。
- 前記チタン(IV)ビス(アンモニウムラクタト)ジヒドロキシドが、前記液体の重量に基づいて約40重量%~約60重量%の量で前記液体中に存在する、請求項3に記載の方法。
- 前記シリカ担体を前記液体に前記接触させることが、前記シリカ担体に前記液体を含浸させることを含む、請求項1に記載の方法。
- 前記シリカ担体に前記含浸させることが、前記シリカ担体をインシピエントウェットネス含浸法に供することを含む、請求項9に記載の方法。
- 前記チタン処理済みシリカ担体をか焼すること;及び
前記チタン処理済みシリカ担体をシリル化して前記チタン化シリカ触媒を形成することをさらに含む、請求項1に記載の方法。 - 前記チタン処理済みシリカ担体を前記か焼することが、前記チタン処理済みシリカ担体を空気中で約300℃~約800℃の温度に約1時間~約3時間加熱することを含む、請求項11に記載の方法。
- 前記か焼されたチタン処理済みシリカ担体を前記シリル化することが、前記か焼されたチタン処理済みシリカ担体を次式:
R3SiNHSiR’3
(式中、各R及びR’は独立に、一価C1~C6ヒドロカルビルから選択される)のオルガノジシラザンに接触させることを含む、請求項11に記載の方法。 - 前記シリル化剤がヘキサメチルジシラザンを含む、請求項13に記載の方法。
- オレフィンエポキシ化の方法であって、
請求項11に記載の方法によって調製されるチタン化シリカ触媒を用意すること;及び
オキシダントの存在下及びオレフィンをエポキシ化してエポキシ化オレフィンを形成するのに有効な条件下で前記オレフィンを前記チタン化シリカ触媒に接触させることを含む。 - 前記オレフィンがプロピレンを含む、請求項15に記載の方法。
- 前記オキシダントがヒドロペルオキシドを含む、請求項15に記載の方法。
- 前記オキシダントが、1-エチルブチルヒドロペルオキシド(EBHP)、t-ブチルヒドロペルオキシド(TBHP)、又はクメン過酸化水素(CHP)を含む、請求項17に記載の方法。
- 前記オレフィンの約20mol%~100mol%が前記エポキシ化オレフィンに転化される、請求項15に記載の方法。
- 前記オレフィンの約85mol%~100mol%が前記エポキシ化オレフィンに転化される、請求項15に記載の方法。
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US5733840A (en) * | 1996-06-06 | 1998-03-31 | Norton Chemical Process Products Corporation | Catalyst carrier |
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US5759945A (en) * | 1997-03-26 | 1998-06-02 | Arco Chemical Technology, L.P. | Preparation of titanium-containing catalysts using titanosiloxane polymers |
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