JP2015536302A - C5アルデヒドを製造するための長時間安定した方法 - Google Patents
C5アルデヒドを製造するための長時間安定した方法 Download PDFInfo
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- JP2015536302A JP2015536302A JP2015536051A JP2015536051A JP2015536302A JP 2015536302 A JP2015536302 A JP 2015536302A JP 2015536051 A JP2015536051 A JP 2015536051A JP 2015536051 A JP2015536051 A JP 2015536051A JP 2015536302 A JP2015536302 A JP 2015536302A
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- reactor
- hydroformylation
- ligand
- formula
- bisphosphite
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- 238000000034 method Methods 0.000 claims abstract description 53
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- 0 C*1(Oc(c(*)cc(*)c2)c2-c(cc(*)cc2*)c2O*2Oc3c(*)cc(*)cc3-c3cc(C)cc(*)c3O2)Oc2c(*)cc(*)cc2-c2cc(*)cc(*)c2O1 Chemical compound C*1(Oc(c(*)cc(*)c2)c2-c(cc(*)cc2*)c2O*2Oc3c(*)cc(*)cc3-c3cc(C)cc(*)c3O2)Oc2c(*)cc(*)cc2-c2cc(*)cc(*)c2O1 0.000 description 2
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- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
-
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Abstract
Description
B.Cornils,W.A.Herrmann,“Applied Homogeneous Catalysis with Organometallic Compounds”,Vol.1 & 2,VCH,Weinheim,New York,1996中、
ならびに
R.Franke,D.Selent,A.Boerner,“Applied Hydroformylation”,Chem.Rey.,2012,DOI:10.1021/cr3001803中に見出せる。
Van Leeuwen,Piet W.N.M.およびClaver,Carmen(編):Rhodium Catalyzed Hydroformylation Catalysis by Metal Complexes,Volume 22,Kluwer,2000,第212頁以降中に見出せる。
Deen,N.G.,Mudde,R.F.,Kuipers,J.A.M.,Zehner,P.and Kraume,M.:Bubble Columns.
Ullmann’s Encyclopedia of Industrial Chemistry.オンラインでの刊行:2010年1月15日。DOI:10.1002/14356007.b04_275.pub2
これに関連して、“反応器”とは、数多くの直列接続または並列接続された反応容器であるとも解釈されうる。
例1:1200時間にわたり本発明によらない配位子(4)を用いるヒドロホルミル化
欧州特許第2280920号明細書B1から公知の、式(4)の本発明によらない配位子を、ブテン/ブタン混合物のヒドロホルミル化において使用した。
本試験は、例1中に記載された試験プラント中で実施された。本試験の準備および実施は、例1と同様に行なわれた。
次の処理量を調節した:使用混合物0.3kg/h、合成ガス(H2 50体積%およびCO 50体積%)75Nl/h。
本発明により使用された触媒系を製造するための一般的な反応式は、図4に図示されている。
VE水=脱塩水、
KPG=コアを備えた精密ガラス(KPG)攪拌機、
ACN=アセトニトリル、
EtOAc=エチルアセテート、
DMAB=ジメチルアミノブタン、
NMP=N−メチルピロリドン、
OEV=真空ポンプ用オイル、
acac=アセチルアセトネート、
NEt3=トリエチルアミン、
TIPB=1,2,4,5−テトライソプロピルベンゼン。
前駆体として使用されたビフェノール(7)を、次の合成規定により製造した。
例1と同じ試験プラントを使用した。例1と同じ使用混合物および例1と同じ合成ガスを使用した。しかし、配位子として、例3により製造された、2つのビスホスファイト配位子(1)と(2)との混合物を使用した。欧州特許第2280920号明細書B1から公知の、式(4)の配位子は、反応混合物中に含まれていなかった。比較例1と同じアミン(5)を安定剤として使用した。溶剤として、イソノニルベンゾエートを使用した。
相応する例を比較した場合、本発明により実施された例4は、次の特徴によって明らかに、技術水準を再現する例1および例2から際立って見える。
Claims (12)
- 5個の炭素原子を有するアルデヒドを製造する方法であって、直鎖状ブテン10質量%〜50質量%および1−ブテン5質量%未満を含有する使用混合物を、ロジウムならびに少なくとも1つのビスホスフィット配位子を含む触媒系の存在下に合成ガスでヒドロホルミル化し、その際に、このヒドロホルミル化は反応器中で行なわれ、この反応器から運転時間にわたって、生成物の少なくとも一部ならびにヒドロホルミル化の未反応の出発物質を含む循環ガスを連続的に取り出し、部分的に凝縮させ、かつ循環ガスの未凝縮分を前記反応器中に返送し、運転時間の経過後に、ヒドロホルミル化を中断し、前記反応器から反応残留物を取り除き、かつヒドロホルミル化を再び開始させる、前記方法において、
前記運転時間が少なくとも8000時間にわたって持続されること、
持続される運転時間中に反応器からの固体の反応残留物の分離が省略されること、
および前記触媒系が式(1)のビスホスファイト配位子および/または式(2)のビスホスファイト配位子:
- 前記触媒系が式(1)のビスホスファイト配位子ならびに式(2)のビスホスファイト配位子を含むことを特徴とする、請求項1記載の方法。
- 前記ヒドロホルミル化において、式(1)のビスホスファイト配位子対式(2)のビスホスファイト配位子のモル比率は、10〜30であることを特徴とする、請求項2記載の方法。
- 前記有機アミンは、少なくとも1個の2,2,6,6−テトラメチルピペリジン単位を有することを特徴とする、請求項4記載の方法。
- 前記有機アミンは、セバシン酸ジ−4−(2,2,6,6−テトラメチルピペリジニル)−エステルであることを特徴とする、請求項5記載の方法。
- 前記ヒドロホルミル化は、イソノニルベンゾエートの存在下に実施されることを特徴とする、請求項1から6までのいずれか1項に記載の方法。
- 循環ガスは、50℃〜90℃の凝縮温度で部分凝縮されること;好ましくは、凝縮温度が65℃〜75℃であること;殊に好ましくは、前記凝縮温度が70℃であることを特徴とする、請求項1から7までのいずれか1項に記載の方法。
- 前記運転時間は12000時間以上であることを特徴とする、請求項1から8までのいずれか1項に記載の方法。
- 前記使用混合物は、直鎖状ブテンを10〜50質量%、1−ブテンを2質量%未満およびブタンを少なくとも50質量%含有することを特徴とする、請求項1から9までのいずれか1項に記載の方法。
- 前記ヒドロホルミル化は、次の反応条件:
圧力:1MPa〜20MPa;
温度:70℃〜150℃;
ロジウム濃度:1質量ppm〜1000質量ppm;
配位子/ロジウム比率:1〜100
で実施されることを特徴とする、請求項1から10までのいずれか1項に記載の方法。 - ロジウムならびに少なくとも1つのビスホスファイト配位子を含む触媒系の存在下に直鎖状ブテンおよび合成ガスをヒドロホルミル化することによって、5個の炭素原子を有するアルデヒドを製造するための反応器を含み、さらに、生成物の少なくとも一部ならびにヒドロホルミル化の未反応の出発物質を含む循環ガスを前記反応器から取出すための手段を含み、さらに、前記循環ガスを部分凝縮するための手段、および循環ガスの未凝縮分を前記反応器中に返送するための手段を含む、請求項1から11までのいずれか1項に記載の方法を実施するためのプラントにおいて、
前記反応器が式(1)のビスホスファイト配位子および/または式(2)のビスホスファイト配位子を含むことを特徴とする、前記プラント。
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