JP6867758B2 - アクリロニトリルの生産に関連する組成物及び方法 - Google Patents
アクリロニトリルの生産に関連する組成物及び方法 Download PDFInfo
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- JP6867758B2 JP6867758B2 JP2016120422A JP2016120422A JP6867758B2 JP 6867758 B2 JP6867758 B2 JP 6867758B2 JP 2016120422 A JP2016120422 A JP 2016120422A JP 2016120422 A JP2016120422 A JP 2016120422A JP 6867758 B2 JP6867758 B2 JP 6867758B2
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- catalyst
- acrolein
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- propylene glycol
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Images
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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
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- 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
- B01J23/888—Tungsten
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- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
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- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/892—Nickel and noble metals
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- 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
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8926—Copper and noble metals
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
- C07C253/26—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons containing carbon-to-carbon multiple bonds, e.g. unsaturated aldehydes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/06—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and unsaturated carbon skeleton
- C07C255/07—Mononitriles
- C07C255/08—Acrylonitrile; Methacrylonitrile
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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Description
本出願は、2015年6月19に提出された米国特許仮出願第62/182,092の利益を主張し、その全体が参照により本明細書に援用される。
本発明は、エネルギー省のエネルギー効率・再生可能エネルギー局(DOE−EERE)によって授与されたDE−EE0006781の下、政府の支援によってなされた。米国政府は本発明に特定の権利を有する。
本明細書に開示される組成物、物品及び方法は、アクリロニトリル及び他の有用な化学物質の生産に関する。
M1M2xM3yOz
M1は、脱水素及びC−O開裂を促す金属であり、
M2は、脱水を促す酸部位を有する金属であり、
M3は、M1と結合して脱水と脱水素の両方を促す酸部位及び塩基部位を有する両性触媒担体であり、
xは、約0.25〜約4のモル比であり、
yは、約0.25〜約4のモル比であり、
zは、M1、M2、及びM3に結合された酸素の総量であり、M1、M2、及びM3の酸化状態の合計に対応する、触媒組成物を開示している。
1.定義
2.アクリロニトリルを生産するための中間体の生産
a.触媒組成物
M1M2xM3yOz
M1は、脱水素及びC−O開裂を促す金属であり、
M2は、脱水を促す酸部位を有する金属であり、
M3は、M1と関連して脱水と脱水素の両方を促す酸部位及び塩基部位を有する両性触媒担体であり、
xは、約0.25〜約4のモル比であり、
yは、約0.25〜約4のモル比であり、
zは、M1、M2、及びM3に結合された酸素の総量であり、M1、M2、及びM3の酸化状態の合計に対応する、触媒組成物を開示している。
b.方法
I.エチレングリコール、プロピレングリコール、及びグリセロールの生産
II.アクロレイン及びアセトアルデヒドの生産
以下の実施例は、完全な開示及び本明細書で請求の化合物、組成物、物品、装置及び/または方法がいかにして作製され、評価されるのかの記載により当業者に提供され、単に例示を意図したものであり、本開示を限定することを意図したものではない。数値(例えば、量、温度等)に関して確実な精度を期しているが、多少の誤差及び偏差は考慮されるべきである。特に指示がない限り、部は質量部であり、温度は℃または周囲温度であり、圧力は大気圧または大気圧近傍である。実施例は本発明を例示するために本明細書中に提供され、決して本発明を限定するものとして解釈されるべきではない。
1.触媒の実験パラメータ及び試験
表1
2.触媒の実験パラメータ及び試験
本発明のまた別の態様は、以下のとおりであってもよい。
〔1〕プロピレングリコール及びグリセロールをアクロレインに変換する触媒組成物であって、以下の式:
M1M2 x M3 y O z
を有する触媒を含み、
M1は、脱水素及びC−O開裂を促す金属であり、
M2は、脱水を促す酸部位を有する金属であり、
M3は、M1と関連して脱水と脱水素の両方を促す酸部位及び塩基部位を有する両性触媒担体であり、
xは、約0.25〜約4のモル比であり、
yは、約0.25〜約4のモル比であり、
zは、M1、M2及びM3と結合された酸素の総量であり、M1、M2及びM3の酸化状態の合計に対応することを特徴とする、触媒組成物。
〔2〕M1は、Cu、Zn及びSnから成る群から選択される、前記〔1〕に記載の触媒組成物。
〔3〕M2は、W、Fe、P及びゼオライトから成る群から選択される、前記〔1〕または〔2〕に記載の触媒組成物。
〔4〕M3は、Zr、Al、Si、Mg、Ti、La及びCeから成る群から選択される、前記〔1〕〜〔3〕のいずれか1項に記載の触媒組成物。
〔5〕xは、約0.8〜約2.2である、前記〔1〕〜〔4〕のいずれか1項に記載の触媒組成物。
〔6〕yは、約0.8〜約2.2である、前記〔1〕〜〔5〕のいずれか1項に記載の触媒組成物。
〔7〕M1は、Cuである、前記〔1〕〜〔6〕のいずれか1項に記載の触媒組成物。
〔8〕M2は、Wである、前記〔1〕〜〔7〕のいずれか1項に記載の触媒組成物。
〔9〕M3は、Zrである、前記〔1〕〜〔8〕のいずれか1項に記載の触媒組成物。
〔10〕前記触媒が、式CuOWO 3 ZrO 2 またはCuOWO 3 TiO 2 またはCuOWO 3 SiO 2 を有する、前記〔1〕〜〔9〕のいずれか1項に記載の触媒組成物。
〔11〕以下の工程、
a)エチレングリコール、プロピレングリコール及びグリセロールを含む第一産物を、前記〔1〕〜〔10〕のいずれか1項に記載の触媒組成物と接触させ、それによりアクロレイン及びアセトアルデヒドを含む第二産物を生産する工程、
を含むことを特徴とする方法。
〔12〕以下の工程、
b)前記アセトアルデヒドの少なくとも一部分を前記第二産物から分離する工程、及び c)工程b)の後に前記第二産物中のアクロレインの少なくとも一部分をアクリロニトリルに変換する工程、
をさらに含む、前記〔11〕に記載の方法。
〔13〕前記第一産物が、多機能触媒を使用する単一の工程で、C5及び/またはC6糖類から生産される、前記〔11〕または〔12〕に記載の方法。
〔14〕前記C5及び/またはC6糖類が、C5及び/またはC6ヘミセルロースおよびセルロース由来の糖類である、前記〔13〕に記載の方法。
〔15〕前記第一産物中の約10質量%〜約90質量%の前記プロピレングリコール及びグリセロールが、アクロレインに変換される、前記〔11〕〜〔14〕のいずれか1項に記載の方法。
〔16〕前記第二産物が、約20質量%〜約75質量%のアクロレインを含む、前記〔11〕〜〔15〕のいずれか1項に記載の方法。
〔17〕前記多機能触媒が、Cu、Zn、Sn、Ni、Pt、Pd、Ru及びReから成る群から選択される1つ以上の金属と、担体とを含む、前記〔13〕〜〔16〕のいずれか1項に記載の方法。
〔18〕前記担体が、Al 2 O 3 、SiO 2 、炭素、TiO 2 及びMgOから成る群から選択される、前記〔17〕に記載の方法。
〔19〕工程a)が、大気圧で実施される、前記〔11〕〜〔16〕のいずれか1項に記載の方法。
〔20〕以下の工程、
a)単一の工程で、多機能触媒の存在下でC5及び/またはC6糖類をエチレングリコール、プロピレングリコール及びグリセロールを含む第一産物に変換する工程、
を含むことを特徴とする方法。
〔21〕前記多機能触媒が、Cu、Zn、Sn、Ni、Pt、Pd、Ru及びReから成る群から選択される1つ以上の金属と、担体とを含む、前記〔20〕に記載の方法。
〔22〕前記担体が、Al 2 O 3 、SiO 2 、炭素、TiO 2 及びMgOから成る群から選択される、前記〔21〕に記載の方法。
〔23〕前記方法が、水を前記第一産物から分離する工程をさらに含む、前記〔20〕〜〔22〕のいずれか1項に記載の方法。
〔24〕前記方法が、エチレングリコール、プロピレングリコール及びグリセロールを含む前記第一産物を、前記〔1〕〜〔10〕のいずれか1項に記載の触媒組成物と接触させ、それによりアクロレイン及びアセトアルデヒドを含む第二産物を生産する工程をさらに含む、前記〔20〕〜〔23〕のいずれか1項に記載の方法。
〔25〕前記方法が、前記アセトアルデヒドの少なくとも一部分を前記第二産物から分離する工程、及び、前記第二産物中の前記アクロレインの少なくとも一部分をアクリロニトリルに変換する工程をさらに含む、前記〔24〕に記載の方法。
〔26〕前記C5及び/またはC6糖類が、C5及び/またはC6ヘミセルロースおよびセルロース由来の糖類である、前記〔20〕〜〔25〕のいずれか1項に記載の方法。
〔27〕工程a)における約70質量%〜約100質量%の前記C5及び/またはC6糖類が、前記第一産物に変換される、前記〔20〕〜〔26〕のいずれか1項に記載の方法。
〔28〕工程a)が、約130℃〜約200℃の温度で、かつ、水素存在下で約400psig〜約1000psigの圧力で実施される、前記〔20〕〜〔27〕のいずれか1項に記載の方法。
〔29〕以下の工程、
a)プロピレングリコールを触媒組成物と接触させ、それによりアクロレインを生産する工程、
を含むことを特徴とする方法。
〔30〕前記触媒組成物が、前記〔1〕に記載の触媒組成物である、前記〔29〕に記載の方法。
〔31〕M1が、Cu、Zn及びSnから成る群から選択され、M2が、W、Fe、P及びゼオライトから成る群から選択され、M3が、Zr、Al、Si、Mg、Ti、La及びCeから成る群から選択される、前記〔30〕に記載の方法。
〔32〕前記触媒が、式CuOWO 3 ZrO 2 またはCuOWO 3 TiO 2 またはCuOWO 3 SiO 2 を有する、前記〔30〕に記載の方法。
〔33〕工程a)が、大気圧で実施される、前記〔29〕〜〔32〕のいずれか1項に記載の方法。
〔34〕約10質量%〜約90質量%の前記プロピレングリコールが、アクロレインに変換される、前記〔29〕〜〔33〕のいずれか1項に記載の方法。
〔35〕M1が、Cu、Zn及びSnから成る群から選択され、M2が、W、Fe、P及びゼオライトから成る群から選択され、M3が、Zr、Al、Si、Mg、Ti、La及びCeから成る群から選択される、前記〔11〕に記載の方法。
〔36〕前記触媒が、式CuOWO 3 ZrO 2 またはCuOWO 3 TiO 2 またはCuOWO 3 SiO 2 を有する、前記〔11〕〜〔19〕のいずれか1項に記載の方法。
Claims (25)
- プロピレングリコール及びグリセロールをアクロレインに変換する触媒組成物であって、以下の式:
M1M2xM3yOz
で表される触媒を含み、
M1は、脱水素及びC−O開裂を促す金属であり、Cu、Zn及びSnから成る群から選択され、
M2は、脱水を促す酸部位を有する金属であり、W及びFeから成る群から選択され、
M3は、M1と関連して脱水と脱水素の両方を促す酸部位及び塩基部位を有する両性触媒担体であり、Zr、Al、Si、Mg、Ti、La及びCeから成る群から選択され、
xは、0.25〜4のモル比であり、
yは、0.25〜4のモル比であり、
zは、M1、M2及びM3と結合された酸素の総量であり、M1、M2及びM3の酸化状態の合計に対応することを特徴とする、触媒組成物。 - xは、0.8〜2.2である、請求項1に記載の触媒組成物。
- yは、0.8〜2.2である、請求項1又は2に記載の触媒組成物。
- M1は、Cuである、請求項1〜3のいずれか1項に記載の触媒組成物。
- M2は、Wである、請求項1〜4のいずれか1項に記載の触媒組成物。
- M3は、Zrである、請求項1〜5のいずれか1項に記載の触媒組成物。
- 前記触媒が、式CuOWO3ZrO2で表される、請求項1〜6のいずれか1項に記載の触媒組成物。
- 前記触媒が、式CuOWO3TiO2で表される、請求項1〜5のいずれか1項に記載の触媒組成物。
- 前記触媒が、式CuOWO3SiO2で表される、請求項1〜5のいずれか1項に記載の触媒組成物。
- 以下の工程、
a)エチレングリコール、プロピレングリコール及びグリセロールを含む第一産物を、請求項1〜9のいずれか1項に記載の触媒組成物と接触させ、それによりアクロレイン及びアセトアルデヒドを含む第二産物を生産する工程、
を含むことを特徴とする方法。 - 以下の工程、
b)前記アセトアルデヒドの少なくとも一部分を前記第二産物から分離する工程、及び
c)工程b)の後に前記第二産物中のアクロレインの少なくとも一部分をアクリロニトリルに変換する工程、
をさらに含む、請求項10に記載の方法。 - 前記第一産物が、多機能触媒を使用する単一の工程で、C5及び/またはC6糖類から生産される、請求項10または11に記載の方法。
- 前記C5及び/またはC6糖類が、C5及び/またはC6ヘミセルロースおよびセルロース由来の糖類である、請求項12に記載の方法。
- 前記第一産物中の10質量%〜90質量%の前記プロピレングリコール及びグリセロールが、アクロレインに変換される、請求項10〜13のいずれか1項に記載の方法。
- 前記第二産物が、20質量%〜75質量%のアクロレインを含む、請求項10〜14のいずれか1項に記載の方法。
- 前記多機能触媒が、Cu、Zn、Sn、Ni、Pt、Pd、Ru及びReから成る群から選択される1つ以上の金属と、担体とを含む、請求項12または13に記載の方法。
- 前記担体が、Al2O3、SiO2、炭素、TiO2及びMgOから成る群から選択される、請求項16に記載の方法。
- 工程a)が、大気圧で実施される、請求項10〜15のいずれか1項に記載の方法。
- 以下の工程、
a)プロピレングリコールを触媒組成物と接触させ、それによりアクロレインを生産する工程、
を含む方法であって、前記触媒組成物が、請求項1に記載の触媒組成物であることを特徴とする方法。 - 前記触媒が、式CuOWO3ZrO2で表される、請求項19に記載の方法。
- 前記触媒が、式CuOWO3TiO2で表される、請求項19に記載の方法。
- 前記触媒が、式CuOWO3SiO2で表される、請求項19に記載の方法。
- 工程a)が、大気圧で実施される、請求項19〜22のいずれか1項に記載の方法。
- 10質量%〜90質量%の前記プロピレングリコールが、アクロレインに変換される、請求項19〜23のいずれか1項に記載の方法。
- 前記触媒が、式CuOWO3ZrO2またはCuOWO3TiO2またはCuOWO3SiO2で表される、請求項10〜18のいずれか1項に記載の方法。
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US15/096,839 US20160368861A1 (en) | 2015-06-19 | 2016-04-12 | Compositions and methods related to the production of acrylonitrile |
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US1916743A (en) * | 1929-06-15 | 1933-07-04 | Schering Kahlbaum Ag | Production of acrolein |
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US4430253A (en) * | 1982-02-11 | 1984-02-07 | Ethyl Corporation | Sulfide-modified ruthenium catalyst |
US5977013A (en) | 1996-12-19 | 1999-11-02 | Battelle Memorial Institute | Catalyst and method for aqueous phase reactions |
GB9820745D0 (en) * | 1998-09-23 | 1998-11-18 | Capteur Sensors & Analysers | Solid state gas sensors and compounds therefor |
US6841085B2 (en) | 2001-10-23 | 2005-01-11 | Battelle Memorial Institute | Hydrogenolysis of 6-carbon sugars and other organic compounds |
DE102007004351A1 (de) * | 2007-01-29 | 2008-07-31 | Evonik Degussa Gmbh | Neue Katalysatoren und Verfahren zur Dehydratisierung von Glycerin |
DE102007004350A1 (de) | 2007-01-29 | 2008-07-31 | Evonik Degussa Gmbh | Verfahren zur Regenerierung eines Katalysators |
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FR2920767B1 (fr) | 2007-09-06 | 2009-12-18 | Arkema France | Procede de vaporisation reactive de glycerol |
US8461380B2 (en) | 2007-12-28 | 2013-06-11 | Showa Denko K.K. | Method for production of acrylic acid |
WO2009127889A1 (en) | 2008-04-16 | 2009-10-22 | Arkema France | Process for manufacturing acrolein from glycerol |
JP5588341B2 (ja) * | 2008-06-05 | 2014-09-10 | 昭和電工株式会社 | アクロレインの製造方法及びアクリル酸の製造方法 |
FR2932804B1 (fr) | 2008-06-19 | 2010-07-30 | Arkema France | Polymere d'acroleine derive de matiere premiere renouvelable, son procede d'obtention et ses utilisations |
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US20130066100A1 (en) * | 2009-10-15 | 2013-03-14 | Nippon Kayaku Kabushiki Kaisha | Process for preparing catalyst used in production of unsaturated aldehyde and/or unsaturated carboxylic acid by dehydration reaction of glycerin, and catalyst obtained |
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US9422377B2 (en) * | 2011-09-29 | 2016-08-23 | Nippon Shokubai Co., Ltd. | Process for producing acrolein, acrylic acid and derivatives thereof |
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US9708249B1 (en) | 2016-08-24 | 2017-07-18 | Southern Research Institute | Compositions and methods related to the production of acrylonitrile |
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