JP5530437B2 - 二重反応区域プロセスを用いる酢酸からのエチレンの製造 - Google Patents
二重反応区域プロセスを用いる酢酸からのエチレンの製造 Download PDFInfo
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Description
[1]第1の反応区域において、酢酸及び水素を含む供給流を、昇温温度において、好適な水素化触媒を含む第1の触媒組成物と接触させて中間体水素化混合物を生成させ;そして、第2の反応区域において、かかる中間体混合物を、好適な脱水触媒及び場合によっては分解触媒を含む第2の触媒組成物上で反応させてエチレンを生成させる;ことを含む、酢酸からエチレンを選択的に生成する方法。
[2]第1及び第2の反応区域が、それぞれ、固定床内の第1の触媒組成物の第1の層、及び第2の触媒組成物の第2の層を含む、[1]に記載の方法。
[3]第1及び第2の反応区域が別々の容器内である、[1]に記載の方法。
[4]消費された酢酸を基準とするエチレンへの選択率が少なくとも20%である、[1]に記載の方法。
[5]消費された酢酸を基準とするエチレンへの選択率が少なくとも40%である、[1]に記載の方法。
[6]消費された酢酸を基準とするエチレンへの選択率が少なくとも60%である、[1]に記載の方法。
[7]消費された酢酸を基準とするエチレンへの選択率が少なくとも80%である、[1]に記載の方法。
[8]第1の反応区域における水素化を担体上の水素化触媒上で行い、触媒が、銅、ニッケル、アルミニウム、クロム、亜鉛、パラジウム、又はこれらの混合物からなる群から選択される、[1]に記載の方法。
[9]担体が、酸化鉄、シリカ、アルミナ、チタニア、ジルコニア、酸化マグネシウム、ケイ酸カルシウム、炭素、黒鉛、及びこれらの混合物からなる群から選択される、[8]に記載の方法。
[10]水素化触媒が、酸化鉄上に担持されている銅、銅−アルミニウム触媒、銅−亜鉛触媒、銅−クロム触媒、及びニッケル触媒からなる群から選択される、[8]に記載の方法。
[11]水素化触媒が、酸化鉄上に担持されている銅、又は銅−アルミニウム触媒から選択される、[8]に記載の方法。
[12]第2の触媒組成物が、H−モルデナイト、ZSM−5、ゼオライト−X、及びゼオライト−Yからなる群から選択されるゼオライト触媒を含む、[1]に記載の方法。
[13]ゼオライトが約10〜60の範囲のシリカ/アルミナ比(SiO2/Al2O3)を有する、[12]に記載の方法。
[14]中間体混合物がエタノール及び酢酸エチルを含み、第2の触媒組成物が分解触媒を含む、[1]に記載の方法。
[15]水素化触媒が酸化鉄上の銅であり、脱水触媒がH−モルデナイトである、[1]に記載の方法。
[16]酸化鉄上の銅の装填量が約3重量%〜約10重量%の範囲である、[15]に記載の方法。
[17]酸化鉄上の銅の装填量が約4重量%〜約6重量%の範囲である、[15]に記載の方法。
[18]水素化触媒が銅−アルミニウム触媒であり、脱水触媒がH−モルデナイトである、[1]に記載の方法。
[19]銅−アルミニウム触媒に関する銅の装填量が約3重量%〜約10重量%の範囲である、[18]に記載の方法。
[20]銅−アルミニウム触媒に関する銅の装填量が約4重量%〜約6重量%の範囲である、[18]に記載の方法。
[21]水素化及びエチレンへの転化を、気相中、約200℃〜375℃の範囲の温度において行う、[1]に記載の方法。
[22]水素化及びエチレンへの転化を、気相中、約250℃〜350℃の範囲の温度において行う、[21]に記載の方法。
[23]供給流が不活性キャリアガスを含む、[21]に記載の方法。
[24]反応物質が約100:1〜1:100の範囲のモル比の酢酸及び水素から構成され、反応区域の温度が約250℃〜350℃の範囲であり、反応区域の圧力が約1〜30絶対気圧の範囲である、[21]に記載の方法。
[25]反応物質が約1:20〜1:2の範囲のモル比の酢酸及び水素から構成され、反応区域の温度が約300℃〜350℃の範囲であり、反応区域の圧力が約1〜30絶対気圧の範囲である、[21]に記載の方法。
以下において、図1を参照して本発明を詳細に記載する。
「転化率」は、供給流中の酢酸を基準とするモル%として表す。
理論に縛られることは意図しないが、本発明による酢酸のエチレンへの転化は、次の化学式:
本発明方法は、当業者が容易に認めるように固定床反応器又は流動床反応器を用いて種々の形態で実施することができる。断熱反応器を用いることができ、或いは熱伝達媒体を備えたシェルアンドチューブ反応器を用いることができる。いずれの場合においても、2つの反応区域は固定床反応器内に異なる層を有する単一の容器内に収容することができ、或いは2つの反応区域は2つの別々の区域を与えるバッフル及び分離器を有する単一容器の流動床システム内に収容することができる。或いは、異なる反応区域を収容するために2つの容器を用いることができる。いずれの場合においても、2つの区域を有する複式反応器を平行して運転することができ、例えば都合がよければ、平行に配列されている層状の固定床を有する複式管状反応器を用いることができる。
区域20においては、酢酸エチル及びエタノールのような水素化された酢酸の中間体を脱水及び/又は分解してエチレンを生成させ、生成物をスペーサー区域22に送り、最終的には容器12への導入圧よりも低い圧力で生成物流26として床10から排出する。
種々のゼオライト及びゼオライトタイプの材料が、化学反応を触媒することに関して当該技術において公知である。例えば、Argauerの米国特許第3,702,886号においては、種々の炭化水素転化プロセスを触媒するのに有効である「ゼオライトZSM−5」として特徴づけられる合成ゼオライトの種類が開示されている。
「H−ZSM−5」又は「H−モルデナイト」ゼオライトとして特徴づけられる本発明方法における活性触媒は、対応する「ZSM−5」ゼオライト又は「モルデナイト」ゼオライトから、当該技術において周知の技術を用いてこのゼオライトのカチオンの殆ど、一般には少なくとも約80%を水素イオンで置換することによって製造される。これらのゼオライト触媒は、実質的に結晶質のアルミノシリケートであるか、或いは中性形態で明確な結晶構造のシリカ及びアルミナの組み合わせである。本発明の目的のために特に好ましい種類のゼオライト触媒においては、これらのゼオライトにおけるAl2O3に対するSiO2のモル比は、約10〜60の比の範囲内である。
本発明方法の他の形態においては、水素化及び脱水は、触媒床を横切る圧力損失を克服するのに丁度十分な圧力において行う。
実施例A
酸化鉄上5重量%銅の製造:
約0.2mmの均一な粒径分布の粉末化し篩別した酸化鉄(100g)を、オーブン内、窒素雰囲気下で120℃において一晩乾燥し、次に室温に冷却した。これに、蒸留水(100mL)中の硝酸銅(17g)の溶液を加えた。得られたスラリーを、オーブン内で110℃に徐々に加熱(>2時間、10℃/分)して乾燥した。次に、含浸した触媒混合物を500℃においてカ焼した(6時間、1℃/分)。
H−モルデナイトゼオライトの製造:
アンモニウム形態のモルデナイトを500〜550℃において4〜8時間カ焼することによって、H−モルデナイトゼオライトを製造した。ナトリウム形態のモルデナイトを前駆体として用いる場合には、カ焼の前にナトリウムモルデナイトをアンモニウム形態にイオン交換した。
オンラインGCによって生成物の分析を行った。1つの炎イオン化検出器(FID)及び2つの熱伝導度型検出器(TCD)を備えた3チャンネルの小型GCを用いて、反応物質及び生成物を分析した。フロントチャンネルには、FID及びCP-Sil 5(20m)+WaxFFap(5m)カラムを取り付け、これを用いて
アセトアルデヒド;
エタノール;
アセトン;
酢酸メチル;
酢酸ビニル;
酢酸エチル;
酢酸;
エチレングリコールジアセテート;
エチレングリコール;
エチリデンジアセテート;
パラアルデヒド;
を定量した。
CO2;
エチレン;
エタン;
を定量した。
ヘリウム;
水素;
窒素;
メタン;
一酸化炭素;
を定量した。
用いた触媒は、酸化鉄上銅触媒、Sud Chemieから購入したT-4489、及び米国特許第4,018,514号にしたがって製造したナトリウムアルミノシリケートモルデナイト触媒中のゼオライトの重量を基準として500ppm以外のナトリウムイオンを水素イオンで置換することによって製造したH−モルデナイトゼオライト、或いはシリカとアルミナとの比が好ましくは約15:1〜約100:1の範囲である同等物であった。好適な触媒は、約20:1のシリカとアルミナとの比を有するZeolyst Internationalから入手できるCBV21Aである。
用いた触媒は、実施例Aの手順にしたがって製造した酸化鉄上5重量%銅、及び実施例1において上述したようにナトリウムアルミノシリケートモルデナイト触媒中のゼオライトの重量を基準として500ppm以外のナトリウムイオンを水素イオンで置換することによって製造したH−モルデナイトゼオライトであった。
これらの例は、エチレンが生成されなかったか及び/又は非常に低いレベルのエチレンが検出された種々の触媒上での酢酸と水素の反応を示す。
Claims (14)
- 第1の反応区域において、蒸気形態の酢酸及び水素を含む供給流を、200℃〜375℃の温度において、担体上の銅、ニッケル、アルミニウム、クロム、亜鉛、パラジウム、又はこれらの混合物からなる群から選択される金属からなる水素化触媒を含む第1の触媒組成物と接触させて中間体水素化混合物を生成し;そして、
第2の反応区域において、かかる中間体水素化混合物を、H−モルデナイト、ZSM−5、ゼオライトX、及びゼオライトYからなる群から選択されるゼオライト触媒を含む脱水触媒を含む第2の触媒組成物上で反応させてエチレンを生成する;
ことを含む、酢酸からエチレンを選択的に生成する方法であって、
ここで、消費された酢酸を基準とするエチレンへの選択率が10%より大きく、
ゼオライトが10〜60の範囲のシリカ/アルミナ比(SiO 2 /Al 2 O 3 )を有する、
上記方法。 - 第1及び第2の反応区域が、それぞれ、固定床内の第1の触媒組成物の第1の層、及び第2の触媒組成物の第2の層を含む、請求項1に記載の方法。
- 第1及び第2の反応区域が別々の容器内である、請求項1又は2に記載の方法。
- 消費された酢酸を基準とするエチレンへの選択率が少なくとも20%である、請求項1〜3のいずれか1項に記載の方法。
- 消費された酢酸を基準とするエチレンへの選択率が少なくとも40%である、請求項1〜4のいずれか1項に記載の方法。
- 消費された酢酸を基準とするエチレンへの選択率が少なくとも60%である、請求項1〜5のいずれか1項に記載の方法。
- 担体が、酸化鉄、シリカ、アルミナ、チタニア、ジルコニア、酸化マグネシウム、ケイ酸カルシウム、炭素、黒鉛、及びこれらの混合物からなる群から選択される、請求項1〜6のいずれか1項に記載の方法。
- 中間体水素化混合物がエタノール及び酢酸エチルを含む、請求項1〜7のいずれか1項記載の方法。
- 水素化触媒が酸化鉄上の銅であり、脱水触媒がH−モルデナイトである、請求項1〜8のいずれか1項に記載の方法。
- 水素化触媒が銅−アルミニウム触媒であり、脱水触媒がH−モルデナイトである、請求項1〜8のいずれか1項に記載の方法。
- 水素化及びエチレンへの転化を250℃〜350℃の範囲の温度において行う、請求項1〜9のいずれか1項に記載の方法。
- 反応物質が100:1〜1:100の範囲のモル比の酢酸及び水素から構成され、第1の反応区域の圧力が1〜30絶対気圧の範囲である、請求項1〜11のいずれか1項に記載の方法。
- 反応物質が1:20〜1:2の範囲のモル比の酢酸及び水素から構成され、第1の反応区域の温度が300℃〜350℃の範囲である、請求項1〜12のいずれか1項に記載の方法。
- 第1の反応区域において、蒸気形態の酢酸及び水素を含む供給流を、250℃〜350℃の温度において、酸化鉄担体上の銅又は担体上の銅−アルミニウム触媒からなる群から選択される水素化触媒を含む第1の触媒組成物と接触させて、酢酸、エタノール、及び酢酸エチルを含む中間体水素化混合物を生成し;そして
同時に、第2の反応区域において、中間体水素化混合物を、H−モルデナイト及びナトリウムゼオライトYからなる群から選択されるゼオライト触媒を含む脱水触媒を含む第2の触媒組成物上で反応させてエチレンを生成する;
ことを含む、酢酸からエチレンを選択的に生成する方法であって、
ここで、消費された酢酸を基準とするエチレンへの選択率が10%より大きく、
ゼオライトが10〜60の範囲のシリカ/アルミナ比(SiO 2 /Al 2 O 3 )を有する、
上記方法。
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US12/221,138 US20100030002A1 (en) | 2008-07-31 | 2008-07-31 | Ethylene production from acetic acid utilizing dual reaction zone process |
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-
2008
- 2008-07-31 US US12/221,138 patent/US20100030002A1/en not_active Abandoned
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2009
- 2009-07-20 NZ NZ591033A patent/NZ591033A/xx not_active IP Right Cessation
- 2009-07-20 KR KR1020117004662A patent/KR20110069773A/ko not_active Application Discontinuation
- 2009-07-20 EP EP09788948.9A patent/EP2318334B1/en not_active Not-in-force
- 2009-07-20 CN CN200980136279.3A patent/CN102159521B/zh not_active Expired - Fee Related
- 2009-07-20 RU RU2011107272/04A patent/RU2011107272A/ru not_active Application Discontinuation
- 2009-07-20 JP JP2011521094A patent/JP5530437B2/ja not_active Expired - Fee Related
- 2009-07-20 WO PCT/US2009/004191 patent/WO2010014148A2/en active Application Filing
- 2009-07-20 CA CA2732500A patent/CA2732500A1/en not_active Abandoned
- 2009-07-20 AU AU2009277186A patent/AU2009277186A1/en not_active Abandoned
- 2009-07-31 TW TW098125970A patent/TW201022183A/zh unknown
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Also Published As
Publication number | Publication date |
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US20100030002A1 (en) | 2010-02-04 |
KR20110069773A (ko) | 2011-06-23 |
AU2009277186A2 (en) | 2011-03-10 |
ZA201100794B (en) | 2012-05-01 |
EP2318334B1 (en) | 2013-07-17 |
JP2011529495A (ja) | 2011-12-08 |
NZ591033A (en) | 2012-11-30 |
TW201022183A (en) | 2010-06-16 |
CN102159521B (zh) | 2014-07-09 |
EP2318334A2 (en) | 2011-05-11 |
HK1159076A1 (en) | 2012-07-27 |
AR074715A1 (es) | 2011-02-09 |
AU2009277186A1 (en) | 2010-02-04 |
CN102159521A (zh) | 2011-08-17 |
WO2010014148A2 (en) | 2010-02-04 |
CA2732500A1 (en) | 2010-02-04 |
WO2010014148A3 (en) | 2010-05-20 |
RU2011107272A (ru) | 2012-09-10 |
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