JP5345202B2 - オレフィンの製造方法 - Google Patents
オレフィンの製造方法 Download PDFInfo
- Publication number
- JP5345202B2 JP5345202B2 JP2011504818A JP2011504818A JP5345202B2 JP 5345202 B2 JP5345202 B2 JP 5345202B2 JP 2011504818 A JP2011504818 A JP 2011504818A JP 2011504818 A JP2011504818 A JP 2011504818A JP 5345202 B2 JP5345202 B2 JP 5345202B2
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- JP
- Japan
- Prior art keywords
- catalyst
- producing
- reaction
- acetone
- olefin
- Prior art date
- 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.)
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- 238000004519 manufacturing process Methods 0.000 title claims description 45
- 150000001336 alkenes Chemical class 0.000 title claims description 41
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 35
- 239000003054 catalyst Substances 0.000 claims description 165
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 144
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 118
- 238000006243 chemical reaction Methods 0.000 claims description 73
- 229910052709 silver Inorganic materials 0.000 claims description 67
- 238000006297 dehydration reaction Methods 0.000 claims description 63
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 60
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 60
- 230000018044 dehydration Effects 0.000 claims description 60
- 239000004332 silver Substances 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 56
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- 150000002576 ketones Chemical class 0.000 claims description 36
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 36
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 35
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- 239000011964 heteropoly acid Substances 0.000 claims description 32
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- 239000010457 zeolite Substances 0.000 claims description 27
- 229910021536 Zeolite Inorganic materials 0.000 claims description 25
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 24
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
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- 150000001768 cations Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 10
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 claims description 9
- 229910044991 metal oxide Inorganic materials 0.000 claims description 7
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- 229910000476 molybdenum oxide Inorganic materials 0.000 claims description 4
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 claims description 4
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 claims description 4
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 claims description 4
- CGFYHILWFSGVJS-UHFFFAOYSA-N silicic acid;trioxotungsten Chemical compound O[Si](O)(O)O.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 CGFYHILWFSGVJS-UHFFFAOYSA-N 0.000 claims description 4
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- -1 alkali metal cation Chemical class 0.000 description 10
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 5
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- 238000007086 side reaction Methods 0.000 description 5
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- 241000588724 Escherichia coli Species 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
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- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
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- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- 240000008042 Zea mays Species 0.000 description 2
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- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
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- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
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- XURCIPRUUASYLR-UHFFFAOYSA-N Omeprazole sulfide Chemical compound N=1C2=CC(OC)=CC=C2NC=1SCC1=NC=C(C)C(OC)=C1C XURCIPRUUASYLR-UHFFFAOYSA-N 0.000 description 1
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/22—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by reduction
-
- 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
- B01J35/19—Catalysts containing parts with different compositions
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Description
本発明には、少なくとも1種の6族(VIB族)の元素を含む金属酸化物触媒、ゼオライト、アルミナ、およびヘテロポリ酸が有するプロトンの一部若しくは全部を金属カチオンで交換したヘテロポリ酸塩から選択される少なくとも1種の脱水触媒が用いられる。本発明において、脱水触媒は、1種単独でも、2種以上を用いてもよい。
本発明に用いる銀元素を含む触媒としては、触媒中に銀元素を含み、水添触媒として作用するものであれば特に制限なく用いることができる。
300mlのナスフラスコにシリカゲル(和光純薬製ワコーゲルC−100)50.0g、乳酸銀(0.5水和物)4.77g、イオン交換水100mlを加えロータリーエバポレータを用い、室温で1時間混合した。20mmHgの減圧下40〜50℃で水を留去し、銀をシリカゲルに担持した。得られた銀が担持されたシリカゲルに、水素気流下で、100℃から5時間をかけて段階的に300℃まで温度を上げる還元処理を行った。その結果、黒色の5%Ag/シリカ触媒52.5gを得た。5%Ag/シリカ触媒を、ふるいを用いて250〜500μに分級した。
高圧用フィードポンプ、高圧用水素マスフロー、高圧用窒素マスフロー、電気炉、触媒充填部分を有する反応器、背圧弁を設置した固定床反応装置を用い、ダウンフローによる加圧液相流通反応を行った。
300mlのナスフラスコに製造例1で調製した5%Ag/シリカ触媒29.1g、硝酸インジウム3水和物0.43g、イオン交換水100mlを加えロータリーエバポレータを用い、室温で1時間混合した。20mmHgの減圧下40〜50℃で水を留去し、硝酸インジウムを5%Ag/シリカ触媒に担持した。得られたインジウムが担持された5%Ag/シリカ触媒に、水素気流下で、100℃から3時間をかけて段階的に300℃まで温度を上げる還元処理を行った。その結果、黒色の5%Ag−0.5%In/シリカ触媒29.2gを得た。5%Ag−0.5%In/シリカ触媒を、ふるいを用いて250〜500μに分級した。
5%Ag/シリカ触媒の代わりに製造例2で調製した5%Ag−0.5%In/シリカ触媒を用い、水素の流量を12ml/分から22ml/分へ増大させた以外は、実施例1と同様に反応を行った。
反応温度を180℃から240℃に上げた以外は、実施例2と同様に反応を行った。
反応温度を180℃から280℃に上げた以外は、実施例2と同様に反応を行った。
β−ゼオライト0.6gをγ−アルミナ(日揮化学製N611N、20MPaで圧縮成型後、250〜500μへ分級したもの)1.0gに変えた以外は、実施例4と同様に反応を行った。
高圧用フィードポンプ、高圧用水素マスフロー、高圧用窒素マスフロー、電気炉、触媒充填部分を有する反応器、背圧弁を設置した固定床反応装置を用い、ダウンフローによる加圧液相流通反応を行った。
(脱水触媒の調製)
H0.5K2.5PW12O40(リンタングステン酸のHを部分的にKに交換したリンタングステン酸カリウム塩)2.0gをエタノール15ml中に入れ、40℃で1時間攪拌した。次いでテトラエトキシシラン6.9gを滴下して加え40℃で1時間攪拌した。これに3.0gの水を加え80℃で24時間攪拌した。生成したゾルを蒸発乾固し、回収した固体を80℃の水に加えて15時間攪拌した後、濾別し、水洗、乾燥後、300℃で焼成し、H0.5K2.5PW12O40がシリカに重量比1:1で担持された脱水触媒を得た。
タングステン酸化物(WO3)の代わりに、上記調製により得られた脱水触媒(H0.5K2.5PW12O40をシリカに担持した触媒)1.0gを用いた以外は、実施例6と同様に反応を行った。反応結果を表2に示す。表2に示したように選択性良くプロピレンを生成した。
(脱水触媒の調製)
H0.5K2.5PW12O40(リンタングステン酸のHを部分的にKに交換したリンタングステン酸カリウム塩)の代わりに、K3PW12O40(リンタングステン酸のHを、全てにKに交換したリンタングステン酸カリウム塩)を用いた以外は、実施例7の脱水触媒の調製と同様に行い、K3PW12O40がシリカに重量比1:1で担持された脱水触媒を得た。
タングステン酸化物(WO3)の代わりに、上記調製により得られた脱水触媒(K3PW12O40をシリカに担持した触媒)1.0gを用いた以外は、実施例6と同様に反応を行った。反応結果を表2に示す。表2に示したように選択性良くプロピレンを生成した。
(イソプロピルアルコールおよびアセトンの製造)
WO2009/008377の実施例4に記載のイソプロピルアルコール生産大腸菌(エシェリヒア・コリpGAP-Iaaa/B株)を用いてイソプロピルアルコールを生産した。本実施例では、WO2009/008377号パンフレット図1に示される生産装置10を用いて処理を行った。培養槽及びトラップ槽には3リットル容のものを使用した。培養槽、トラップ槽、注入管、連結管、排出管は、すべてガラス製のものとした。トラップ槽には、トラップ液としての水(トラップ水)が1.8Lの量で注入されている。更にトラップ水は10℃に冷却して使用した。
コーンスティープリカー(日本食品化工製):20g/L
Fe2SO4・7H2O:0.09g/L
K2HPO4:2g/L
KH2PO4:2g/L
MgSO4・7H2O:2g/L
(NH4)2SO4:2g/L
アデカノールLG126(旭電化工業):0.6g/L
残部:水
(プロピレンの製造)
上記イソプロピルアルコールおよびアセトンを含む水溶液(培養開始130時間後のトラップ水)から蒸留により、イソプロピルアルコール、アセトンを高濃度化し取り出した。
Claims (9)
- 少なくとも1種の6族(VIB族)の元素を含む金属酸化物触媒、ゼオライト、アルミナ、およびヘテロポリ酸が有するプロトンの一部若しくは全部を金属カチオンで交換したヘテロポリ酸塩から選択される少なくとも1種の脱水触媒と、銀元素を含む触媒との存在下で、ケトンと水素とを反応させるオレフィンの製造方法。
- 前記銀元素を含む触媒が、さらに少なくとも1種の13族(IIIA族)の元素を含む請求項1に記載のオレフィンの製造方法。
- 前記脱水触媒が、ゼオライト、γ−アルミナ、タングステン酸化物、モリブデン酸化物、およびヘテロポリ酸が有するプロトンの一部若しくは全部を金属カチオンで交換したヘテロポリ酸塩から選択される少なくとも1種の脱水触媒である請求項1に記載のオレフィンの製造方法。
- 前記ケトンがアセトンであり、前記オレフィンがプロピレンである請求項1〜3のいずれか一項に記載のオレフィンの製造方法。
- 前記ヘテロポリ酸が、リンタングステン酸、ケイタングステン酸、リンモリブデン酸およびケイモリブデン酸から選択される少なくとも1種のヘテロポリ酸である請求項1に記載のオレフィンの製造方法。
- 前記ヘテロポリ酸塩が、シリカに担持されていることを特徴とする請求項1に記載のオレフィンの製造方法。
- 前記反応における反応温度が、50〜500℃である請求項1に記載のオレフィンの製造方法。
- 前記脱水触媒と、銀元素を含む触媒とが、混合された状態で反応を行う請求項1に記載のオレフィンの製造方法。
- 前記ケトンが、植物由来原料からイソプロピルアルコールおよびアセトンを生成しうるイソプロピルアルコール生成細菌より得られたアセトンであり、前記オレフィンが、プロピレンである請求項1に記載のオレフィンの製造方法。
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010241790A (ja) * | 2008-12-01 | 2010-10-28 | Mitsui Chemicals Inc | オレフィンの製造方法 |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5831925B2 (ja) * | 2011-05-13 | 2015-12-09 | 国立大学法人東京工業大学 | プロピレンの製造方法 |
MY168428A (en) | 2012-01-20 | 2018-11-09 | Mitsui Chemicals Inc | Olefin production method |
US20140275688A1 (en) * | 2013-03-14 | 2014-09-18 | Exxonmobil Research And Engineering Company | Methods for producing basestocks from renewable sources using dewaxing catalyst |
US9764313B2 (en) | 2014-06-18 | 2017-09-19 | Basf Corporation | Molecular sieve catalyst compositions, catalyst composites, systems, and methods |
US10850265B2 (en) * | 2014-06-18 | 2020-12-01 | Basf Corporation | Molecular sieve catalyst compositions, catalytic composites, systems, and methods |
US9889437B2 (en) * | 2015-04-15 | 2018-02-13 | Basf Corporation | Isomorphously substituted catalyst |
RU2605427C1 (ru) * | 2015-10-20 | 2016-12-20 | Акционерное общество "Газпромнефть-Московский НПЗ" (АО "Газпромнефть-МНПЗ") | Способ восстановления разветвленных кетонов |
EP3398679A1 (en) | 2015-12-28 | 2018-11-07 | Toyota Jidosha Kabushiki Kaisha | Cluster supported catalyst and production method therefor |
US20170335216A1 (en) * | 2016-05-19 | 2017-11-23 | Chevron U.S.A. Inc. | Base oil having high viscosity index from alkylation of dimer ketone-derived olefin |
JP6683656B2 (ja) * | 2017-06-27 | 2020-04-22 | トヨタ自動車株式会社 | クラスター担持触媒及びその製造方法 |
WO2019004318A1 (ja) | 2017-06-27 | 2019-01-03 | トヨタ自動車株式会社 | クラスター担持多孔質担体及びその製造方法 |
CN112898110B (zh) * | 2019-12-03 | 2022-06-24 | 中国科学院大连化学物理研究所 | 高碳醇脱水制α-高碳烯烃的方法 |
CN114436730B (zh) * | 2020-10-31 | 2023-07-04 | 中国石油化工股份有限公司 | 异丙醇脱水制丙烯的工艺***和工艺方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02174737A (ja) * | 1988-09-30 | 1990-07-06 | Mitsui Petrochem Ind Ltd | フェノールの製造方法およびその製造時の副生アセトンからプロピレンを得る方法 |
JP2008513449A (ja) * | 2004-09-21 | 2008-05-01 | ユーオーピー エルエルシー | 重質オレフィン再循環ストリームの選択的水素化処理によるオキシジェネートのプロピレンへの転化方法 |
WO2009008377A1 (ja) * | 2007-07-11 | 2009-01-15 | Mitsui Chemicals, Inc. | イソプロピルアルコール生産細菌及びこれを用いたイソプロピルアルコール生産方法 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD84378A (ja) | ||||
US4554260A (en) | 1984-07-13 | 1985-11-19 | Exxon Research & Engineering Co. | Two stage process for improving the catalyst life of zeolites in the synthesis of lower olefins from alcohols and their ether derivatives |
JPS6167493A (ja) | 1984-09-10 | 1986-04-07 | Res Assoc Petroleum Alternat Dev<Rapad> | イソプロピルアルコ−ルの製造法 |
US5017729A (en) * | 1988-09-30 | 1991-05-21 | Mitsui Petrochemical Industries, Ltd. | Phenol preparation process and propylene recovery therefrom |
CN1043956A (zh) | 1988-12-31 | 1990-07-18 | 孙书敏 | 用植物废料生产有机溶剂的工艺方法 |
JP2723621B2 (ja) | 1989-07-10 | 1998-03-09 | 三井東圧化学株式会社 | イソプロピルアルコールの製造方法 |
JP2764058B2 (ja) | 1989-07-10 | 1998-06-11 | 三井化学株式会社 | プロピレンの製造方法 |
JPH0691171A (ja) | 1992-09-10 | 1994-04-05 | Tokuyama Soda Co Ltd | ヘテロポリ酸塩担持触媒 |
JPH06167493A (ja) | 1992-11-30 | 1994-06-14 | Kyowa Medex Co Ltd | 免疫測定方法 |
US6046373A (en) * | 1998-04-29 | 2000-04-04 | Exxon Chemical Patents Inc. | Catalytic conversion of oxygenates to olefins |
KR100852565B1 (ko) | 2000-09-25 | 2008-08-18 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 페놀 생산에서 분해 유출물의 수소화 방법 |
US6518475B2 (en) | 2001-02-16 | 2003-02-11 | Exxonmobil Chemical Patents Inc. | Process for making ethylene and propylene |
US7214843B2 (en) * | 2002-11-26 | 2007-05-08 | Exxon Mobil Chemical Patents Inc. | Treating oxygenate containing feedstreams in the conversion of oxygenates to olefins |
US6984761B2 (en) * | 2002-12-16 | 2006-01-10 | Exxonmobil Chemical Patents Inc. | Co-production of phenol, acetone, α-methylstyrene and propylene oxide, and catalyst therefor |
JPWO2007083684A1 (ja) | 2006-01-21 | 2009-06-11 | 国立大学法人東京工業大学 | 触媒およびそれを用いるオレフィンの製造方法 |
WO2010064500A1 (ja) * | 2008-12-01 | 2010-06-10 | 三井化学株式会社 | オレフィンの製造方法 |
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02174737A (ja) * | 1988-09-30 | 1990-07-06 | Mitsui Petrochem Ind Ltd | フェノールの製造方法およびその製造時の副生アセトンからプロピレンを得る方法 |
JP2008513449A (ja) * | 2004-09-21 | 2008-05-01 | ユーオーピー エルエルシー | 重質オレフィン再循環ストリームの選択的水素化処理によるオキシジェネートのプロピレンへの転化方法 |
WO2009008377A1 (ja) * | 2007-07-11 | 2009-01-15 | Mitsui Chemicals, Inc. | イソプロピルアルコール生産細菌及びこれを用いたイソプロピルアルコール生産方法 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010241790A (ja) * | 2008-12-01 | 2010-10-28 | Mitsui Chemicals Inc | オレフィンの製造方法 |
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