JP5371444B2 - テロメリゼーション混合物からの金属−錯体触媒の分離法 - Google Patents
テロメリゼーション混合物からの金属−錯体触媒の分離法 Download PDFInfo
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- JP5371444B2 JP5371444B2 JP2008551675A JP2008551675A JP5371444B2 JP 5371444 B2 JP5371444 B2 JP 5371444B2 JP 2008551675 A JP2008551675 A JP 2008551675A JP 2008551675 A JP2008551675 A JP 2008551675A JP 5371444 B2 JP5371444 B2 JP 5371444B2
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- telomerization
- membrane
- separation
- alkyl
- process according
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- 125000003367 polycyclic group Chemical group 0.000 description 5
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- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical class O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 125000005538 phosphinite group Chemical group 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005597 polymer membrane Polymers 0.000 description 1
- 229920012287 polyphenylene sulfone Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920000131 polyvinylidene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
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Description
とりわけ有利には、本発明による方法において、金属錯体触媒および/または遊離配位子(殊にカルベン配位子および/またはオルガノリン配位子)をテロメリゼーション生成物と比べて少なくとも60%の割合で保持する、その化学的または物理的な特性に基づき適している膜が使用される。
上で挙げられた材料の他に、膜はさらに他の材料を有してよい。殊に、膜は、分離活性層がその上に構成される支持材料または担体材料を有してよい。そのような複合膜の場合、本来の膜の他になお支持材料が存在する。支持材料の選択はEP0781166が記載しており、そこで明確に指摘される。さらに、本発明に従って使用可能な膜中には、殊に圧力変動または高い差圧に対して膜の安定性を高める補強材料、例えば無機酸化物または無機繊維の粒子、例えばセラミック繊維またはガラス繊維が存在していてよい。
しかし、本発明の方法に従って得られる透過液は、例えば従来技術に記載されるような抽出、沈殿または吸着に供給してもよい。
任意には、1,3−ブタジエン含有流からのアセチレン系化合物の分離は、例えば抽出剤としての1つ以上のイオン性液体の使用下で行われうる。
とりわけ有利には、ヘテロ原子によって安定化された少なくとも1つのカルベンを配位子として有する金属錯体触媒が触媒としてテロメリゼーションにおいて使用される。このような配位子の例は、なかでも文献DE10128144、DE10149348、DE10148722、DE10062577、EP1308157およびWO01/66248の中で記載される。これらの文献および殊にそこで記載された配位子は、本出願の開示内容に含まれる。そのうえ活性錯体はなお、さらに他の配位子を有してよい。カルベン配位子は、非環状配位子(offene Liganden)または環状配位子であってよい。
かつ/またはR2およびR‘‘および/またはR‘およびR3は同じかまたは異なっており、炭素原子2〜20個を有する炭素骨格および式VIIIに従う窒素原子を有する環系の一部であり、その際、R2およびR‘‘および/またはR‘およびR3の炭素原子は数えられず、かつその際、該環系の少なくとも1個の水素原子は官能基で置換されていてよく、かつ/または該環系の少なくとも1個の炭素原子はS、P、OおよびNからなる群から選択されるヘテロ原子で置換されていてよく、
かつ/またはR2および/またはR‘‘および/またはR‘および/またはR3は、炭素原子1〜20個からの橋によって配位子Lと結合しており、その際、基R2、R‘‘、R‘およびR3の炭素原子は一緒に数えられず、
およびLは、中性の二電子供与体、環系の一部および/またはアニオン性配位子であるさらに他の配位子であり、その際、官能基は、例えば:−CN、−COOH、−COO−アルキル−、−COO−アリール−、−OCO−アルキル−、−OCO−アリール−、−OCOO−アルキル−、−OCOO−アリール−、−CHO、−CO−アルキル−、−CO−アリール−、−O−アルキル−、−O−アリール−、−NH2、−NH(アルキル)−、−N(アルキル)2−、−NH(アリール)−、−N(アルキル)2−、−F、−Cl、−Br、−I、−OH、−CF3、−NO2、−フェロセニル、−SO3Hおよび−PO3H2の群から選択されていてよく、その際、アルキル基は、例えば炭素原子1〜24個を含み、かつアリール基は、例えば炭素原子5〜24個を含んでよい]のカルベン配位子を有するパラジウムカルベン錯体が使用される。そのような配位子の製造は、例えばDE10148722から引き出されうる。
R2;R3;は同じかまたは異なっており、炭素原子1〜24個を有する直鎖状、分枝鎖状、置換または非置換の環状または非環状アルキル基、または炭素原子6〜24個を有する置換または非置換の単環状または多環状アリール基または
炭素原子4〜24個およびN、O、Sの群からの少なくとも1個のヘテロ原子を有する単環状または多環状の、置換または非置換の複素環であり、
R‘、R‘‘:は同じかまたは異なっており、
水素、アルキル、アリール、ヘテロアリール、−CN、−COOH、−COO−アルキル−、−COO−アリール−、−OCO−アルキル−、−OCO−アリール−、−OCOO−アルキル−、−OCOO−アリール、−CHO、−CO−アルキル−、−CO−アリール−、−O−アルキル−、−O−アリール−、−NH2、−NH(アルキル)−、−N(アルキル)2−、−NH(アリール)−、−N(アルキル)2−、−F、−Cl、−Br、−I、−OH、−CF3、−NO2、−フェロセニル、−SO3H、−PO3H2であり、その際、アルキル基は炭素原子1〜24個を含み、かつアリール−およびヘテロアリール基は炭素原子5〜24個を含み、かつ基R‘およびR‘‘は、架橋する脂肪族環または芳香族環の一部であってもよい、カルベン配位子を有するパラジウムカルベン錯体が使用される。
炭素原子1〜24個を有する直鎖状、分枝鎖状、置換または非置換の環状または非環状アルキル基、または
炭素原子6〜24個を有する置換または非置換の、単環状または多環状アリール基または
炭素原子4〜24個およびN、O、Sの群からの少なくとも1個のヘテロ原子を有する単環状または多環状の、置換または非置換の複素環であり、
R4、R5、R6、R7:は同じかまたは異なっており、
水素、アルキル、アリール、ヘテロアリール、−CN、−COOH、−COO−アルキル−、−COO−アリール−、−OCO−アルキル−、−OCO−アリール−、−OCOO−アルキル−、−OCOO−アリール、−CHO、−CO−アルキル−、−CO−アリール−、−O−アルキル−、−O−アリール−、−NH2、−NH(アルキル)−、−N(アルキル)2−、−NH(アリール)−、−N(アルキル)2−、−F、−Cl、−Br、−I、−OH、−CF3、−NO2、−フェロセニル、−SO3H、−PO3H2であり、その際、アルキル基は炭素原子1〜24個を含み、かつアリール−およびヘテロアリール基は炭素原子5〜24個を含み、かつ基R‘およびR‘‘は、架橋する脂肪族環または芳香族環の一部であってもよい]のものが使用される。一般式IXまたはXに相当するカルベン配位子、およびこのような配位子を含有する錯体の例は、専門文献の中ですでに記載されている(W.A.Hermann,C.Koecher,Angew.Chem.1997,109,2257;Angew.Chem.Int.Ed.Engl.1997,36,2162;V.P.W.Boehm.C.W.K.Gstoettmayr,T.Weskamp,W.A.Hermann,J.Organomet.Chem.2000,595,186;DE4447066)。
基R2およびR3は、とりわけ有利には、5−および6員環のヘテロアルカン、ヘテロアルケンおよびヘテロ芳香族化合物、例えば1,4−ジオキサン、モルホリン、γ−ピラン、ピリジン、ピリミジン、ピラジン、ピロール、フラン、チオフェン、ピラゾール、イミダゾール、チアゾールおよびオキサゾールから誘導される基であってよい。以下の表の中で、このような基R2およびR3の具体的な例が示されている。この表において、〜は、そのつど5員複素環への結合点を示す。
a)金属(パラジウム)が、有利には酸化状態(II)または(0)で存在する金属−カルベン錯体(パラジウム−カルベン錯体)としてかまたは
b)現場で触媒が形成される金属化合物(前駆物質としてのパラジウム化合物)の形で
テロメリゼーションの工程中に導入されうる。
例は、パラジウム(0)カルベン−オレフィン−錯体、パラジウム(0)ジカルベン錯体およびパラジウム(II)ジカルベン錯体、パラジウム(0)カルベン−1,6−ジエン−錯体である。1,6−ジエンとして、例えばジアリルアミン、1,1′−ジビニルテトラメチルジシロキサン、2,7−オクタジエニルエーテルまたは2,7−オクタジエニルアミンが機能しうる。例は、以下の式I−a〜I−eを示す。
パラジウム前駆物質として、例えば:酢酸パラジウム(II)、塩化パラジウム(II)、臭化パラジウム(II)、テトラクロロパラジウム酸リチウム、アセチルアセトネートパラジウム(II)、パラジウム(0)−ジベンジリデンアセトン−錯体、プロピオン酸パラジウム(II)、塩化ビスアセトニトリルパラジウム(II)、二塩化ビストリフェニルホスファンパラジウム(II)、塩化ビスベンゾニトリルパラジウム(II)、ビス(トリ−o−トリルホスフィン)パラジウム(0)およびさらに他のパラジウム(0)−およびパラジウム(II)錯体が使用されうる。
R1a−O−H (VIIa)、または(R1a)(R1b)N−H (VIIb)またはR1a−COOH (VIIc)
[式中、R1aおよびR1bは互いに無関係に、水素、直鎖状、分枝鎖状または環状のC1〜C22−アルキル基、アルケニル基、アルキニル基、C5〜C18アリール基または−CO−アルキル−(C1〜C8)−基またはCO−アリール−(C5〜C10)−基から選択されており、その際、これらの基は、−CN、−COOH、−COO−アルキル−(C1〜C8)、−CO−アルキル−(C1〜C8)、−アリール−(C5〜C10)、−COO−アリール−(C6〜C10)、−CO−アリール−(C6〜C10)、−O−アルキル−(C1〜C8)、−O−CO−アルキル−(C1〜C8)、−N−アルキル2−(C1〜C8)、−CHO、−SO3H、−NH2、−F、−Cl、−OH、−CF3、−NO2の群から選択される置換基を含有してよく、かつその際、基R1aおよびR1bは共有結合を介して互いに結合していてよい]の化合物が使用される。有利には、求核剤として、基R1aおよび場合によりR1bが水素、メチル、エチル、n−プロピル、イソプロピル、t−ブチル、n−ブチル、s−ブチル、ペンチル、ヘキシル、ヘプチル、オクチル、オクテニル、オクタジエニル、イソノニル、2−エチルヘキシル、n−ノニル、フェニル、m−、o−、またはp−メチルフェニル、ナフチル、2,4−ジ−t−ブチルフェニル、2,6−ジ−t−ブチルメチルフェニル、水素カルボニル、メチルカルボニル、エチルカルボニル、プロピルカルボニルまたはフェニルカルボニルである化合物が使用される。
−水、アンモニア、
−モノアルコールおよびフェノール、例えばメタノール、エタノール、n−プロパノール、イソプロパノール、アリルアルコール、n−ブタノール、i−ブタノール、オクタノール、2−エチルヘキサノール、イソノナノール、ベンジルアルコール、シクロヘキサノール、シクロペンタノールまたは2,7−オクタジエン−1−オール、フェノール、
−ジアルコール、例えばエチレングリコール、1,2−プロパンジオール、1,3−プロパンジオール、1,4−ブタンジオール、1,2−ブタンジオール、2,3−ブタンジオールおよび1,3−ブタンジオール、
−ヒドロキシ化合物、例えばα−ヒドロキシ酢酸エステル、
−第一級アミン、例えばメチルアミン、エチルアミン、プロピルアミン、ブチルアミン、オクチルアミン、2,7−オクタジエニルアミン、ドデシルアミン、エチレンジアミンまたはヘキサメチレンジアミン、
−第二級アミン、例えばジメチルアミン、ジエチルアミン、N−メチルアニリン、ビス(2,7−オクタジエニル)アミン、ジシクロヘキシルアミン、メチルシクロヘキシルアミン、ピロリジン、ピペリジン、モルホリン、ピペラジンまたはヘキサメチレンイミンまたは
−カルボン酸、例えばギ酸、酢酸、プロパン酸、ブテン酸、イソブテン酸、安息香酸、1,2−ベンゾールジカルボン酸(フタル酸)である。
IV V VI
Me=一価の金属または一価の金属等価物で、RおよびR1は、上でR1aに関して示された意味を有し、かつR2は、上でR1bに関して示された意味を有する。
テロメリゼーションは連続的にまたは不連続的に運転されえ、かつ特定の反応器タイプの使用に制限されない。その中で反応が実施されうる反応器の例は、撹拌槽反応器、撹拌槽カスケード、流管およびループ型反応器である。種々の反応器の組み合わせ、例えば後接続された流管を有する撹拌槽反応器も可能である。
R1a−O−H VIIa (R1a)(R1b)N−H VIIb R1a−COOH VIIc
その際、R1aおよびR1bは上で挙げられた意味を有する、に従う求核剤(VII)の反応によって得られるテロメリゼーション混合物の後処理のために使用されうる。
R1aは、H、メチル、エチル、n−プロピル、イソプロピル、t−ブチル、n−ブチル、s−ブチル、ペンチル、ヘキシル、ヘプチル、オクチル、オクテニル、オクタジエニル、イソノニル、2−エチルヘキシル、n−ノニル、フェニル、m−、o−、またはp−メチルフェニル、ナフチル、2,4−ジ−t−ブチルフェニル、2,6−ジ−t−ブチルメチルフェニル、水素カルボニル、メチルカルボニル、エチルカルボニル、プロピルカルボニルまたはフェニルカルボニルであり、かつ/または
R1bは、H、メチル、エチル、n−プロピル、イソプロピル、t−ブチル、n−ブチル、s−ブチル、ペンチル、ヘキシル、ヘプチル、オクチル、オクテニル、オクタジエニル、イソノニル、2−エチルヘキシル、n−ノニル、フェニル、m−、o−、またはp−メチルフェニル、ナフチル、2,4−ジ−t−ブチルフェニル、2,6−ジ−t−ブチルメチルフェニル、水素カルボニル、メチルカルボニル、エチルカルボニル、プロピルカルボニルまたはフェニルカルボニルである。極めて有利には、本発明による方法により、式IIIaに従うR1a=水素、メチル、エチル、フェニルまたはメチルカルボニルの化合物が製造される。式IIIaおよびIIIbの化合物は、シス形でもトランス形でも存在してよい。
図2では、実施例1に従う試験装置中での工程の実施が概略的に示される。該工程は、取り付けられた攪拌機およびナノフィルターNを有する反応器Rの中での反応からなる。装置全体はアルゴンARにより洗浄されえ、かつ酸素不含に調整されうる。反応のために、パラジウム化合物および配位子を含有する出発材料混合物Eが反応器Rの中に装入されかつ反応させられる。反応生成物はナノフィルターNに移送される。ナノフィルターから、膜により主に反応生成物からなる透過液Pが得られる。ナノろ過に際して生ずる、触媒ならびに配位子を含有する保持液RTは反応器中に返送される。それによって、分離された触媒−配位子混合物が濃縮される。
例えば図2の中で示される試験装置中に、テロメリゼーション反応のために出発材料(E)を、酸素排除下でアルゴン(Ar)により事前に洗浄することによって以下の組成で装入した:
・メタノール331.4g
・分解C4 1170g(そのうち1,3−ブタジエン511.2g)(Oxeno Olefinchemie GmbH)
・パラジウムアセチルアセテート0.1040g(Umicore)
・1,3−ジメシチルイミダゾリウムクロリド0.7658g(Degussa AG)
・ナトリウムメチレート7.6g(Aldrich)
・o−クレゾール13.42g(Aldrich)
・トリプロピレングリコール200.8g(Aldrich)
全ての出発材料が80℃で反応器中に装入された後、最後に、配位子(1,3−ジメシチルイミダゾリウムクロリド)を有するPd−触媒をメタノールの残留量(100g)とともに添加し、かつそれにより反応を開始させた。反応器にて1時間ごとにサンプル採取を行うことによって、反応挙動をGCにより調査した。
Claims (18)
- テロメリゼーションから得られた反応混合物からのパラジウムカルベン錯体触媒の分離法において、テロメリゼーション反応を、塩基の存在下で実施し、かつパラジウムカルベン錯体触媒を、分離活性層としてポリイミド(PI)、芳香族ポリアミド(PA)、ポリアミドイミド(PAI)、ポリベンズイミダゾール、アクリロニトリル/グリシジルメタクリレート(PANGMA)、ポリベンズイミダゾロン、ポリアクリルニトリル(PAN)、ポリアリールエーテルスルホン、ポリエステル、ポリエーテルエーテルケトン(PEEK)、ポリカーボネート(PC)、ポリテトラフルオロエチレン、ポリベンズイミダゾール(PBI)、ポリビニリデンフルオリド(PVDF)、ポリプロピレン(PP)、ポリジメチルシロキサン(PDMS)からのアルカリ安定性および溶媒安定性のナノフィルターポリマー層を有するか、またはその分離活性層が固有の微小孔構造(PIM)を有するポリマーから構成されているか、またはその分離活性層が疎水化されたセラミック膜を介して構成されている膜から選択される少なくとも1つの膜により分離することを特徴とする、分離法。
- 2つ以上の膜を使用することを特徴とする、請求項1記載の方法。
- 2つ以上の膜モジュールを使用することを特徴とする、請求項1または2記載の方法。
- 分離を、圧力をかけた工程として行うことを特徴とする、請求項1から3までのいずれか1項記載の方法。
- 膜分離を、保持液側対透過液側の圧力差が少なくとも0.5MPaで存在するように実施することを特徴とする、請求項1から4までのいずれか1項記載の方法。
- 該方法を0.1〜15m/秒の膜での膜面流速で実施することを特徴とする、請求項1から5までのいずれか1項記載の方法。
- クロスフローにおいて膜に送られる流(返送された保持液を含む新鮮な供給流)対透過液流の体積流比が100〜10000:1であることを特徴とする、請求項1から6までのいずれか1項記載の方法。
- 分離されたパラジウムカルベン錯体触媒をテロメリゼーションに返送することを特徴とする、請求項1から7までのいずれか1項記載の方法。
- カルベン配位子から選択される遊離配位子を膜により分離し、かつテロメリゼーションに返送することを特徴とする、請求項1から8までのいずれか1項記載の方法。
- 遊離配位子が反応混合物中に存在することを特徴とする、請求項9記載の方法。
- テロメリゼーション生成物に対するカルベン配位子の分子−体積比が≧1.5であることを特徴とする、請求項9または10記載の方法。
- テロメリゼーション混合物を、圧力および温度(℃)に関して最大0〜50%、テロメリゼーションの反応条件と異なる条件下で膜に送ることを特徴とする、請求項1から11までのいずれか1項記載の方法。
- テロメリゼーション混合物を、テロメリゼーションの反応条件下より0〜30%小さい圧力および/または温度で膜に送ることを特徴とする、請求項12記載の方法。
- テロメリゼーションからの反応混合物として、パラジウムカルベン錯体触媒の使用下で、少なくとも2つの共役二重結合を有する非環状オレフィンと少なくとも1つの求核剤のテロメリゼーションによって得られるテロメリゼーション混合物を使用することを特徴とする、請求項1から13までのいずれか1項記載の方法。
- テロメリゼーションにおいて、カルベン配位子対金属[モル/モル]の比が0.01対1〜250対1であることを特徴とする、請求項9から11までのいずれか1項記載の方法。
- テロメリゼーションにおいて、求核剤(VII)として、水、アルコール、フェノール、ポリオール、カルボン酸、アンモニアおよび/または第一級または第二級アミンを使用することを特徴とする、請求項1から15までのいずれか1項記載の方法。
- 分離を80〜100℃の温度で実施することを特徴とする、請求項1から16までのいずれか1項記載の方法。
- 分離を0.5〜5MPaの差圧で実施することを特徴とする、請求項1から17までのいずれか1項記載の方法。
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CN114160205A (zh) * | 2021-12-13 | 2022-03-11 | 浙江迪萧科技有限公司 | 一种有机料液中络合物催化剂的浓缩回收方法 |
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DE3842819A1 (de) * | 1988-12-20 | 1990-06-21 | Hoechst Ag | Verfahren zur abtrennung von metallorganischen verbindungen und/oder metallcarbonylen aus ihren loesungen in organischen medien |
US5243099A (en) * | 1991-12-06 | 1993-09-07 | Union Carbide Chemicals & Plastics Technology Corporation | Synthesis of alpha-substituted alkadienes |
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KR970703805A (ko) * | 1995-05-01 | 1997-08-09 | 유니온 카바이드 케미칼즈 앤드 플라스틱스 테크놀러지 코포레이션 | 막 분리방법(Membrane Separation) |
EP1103303A1 (en) * | 1999-11-23 | 2001-05-30 | Dsm N.V. | Process to separate a rhodium/phosphite ligand complex and free phosphite ligand complex from a hydroformylation mixture |
DE10128144A1 (de) * | 2001-06-09 | 2002-12-12 | Oxeno Olefinchemie Gmbh | Verfahren zur Telomerisation von nicht cyclischen Olefinen |
DE10149348A1 (de) * | 2001-10-06 | 2003-04-10 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von 1-Olefin mit Palladiumcarbenverbindungen |
DE10163347A1 (de) * | 2001-12-21 | 2003-07-10 | Basf Ag | Verfahren zur Hydroformylierung in Gegenwart eines polymeren Liganden mit Phosphacyclohexan-Strukturelementen |
DE10312829A1 (de) * | 2002-06-29 | 2004-01-22 | Oxeno Olefinchemie Gmbh | Verfahren zur Telomerisation von nicht cyclischen Olefinen |
JP4421310B2 (ja) * | 2003-01-21 | 2010-02-24 | 株式会社クラレ | エーテル類の製造方法 |
DE10308111A1 (de) * | 2003-02-26 | 2004-09-09 | Bayer Technology Services Gmbh | Verfahren zum Abtrennen von gelösten oder kolloidalen Feststoffen aus nicht wässrigen Lösungen |
DE102005036038A1 (de) * | 2004-08-28 | 2006-03-02 | Oxeno Olefinchemie Gmbh | Verfahren zur Telomerisation von nicht cyclischen Olefinen |
DE102005036039A1 (de) * | 2004-08-28 | 2006-03-02 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von 2,7-Octadienylderivaten |
DE102005036040A1 (de) * | 2004-08-28 | 2006-03-02 | Oxeno Olefinchemie Gmbh | Verfahren zur Telomerisation von nicht cyclischen Olefinen |
DE102005046250B4 (de) * | 2005-09-27 | 2020-10-08 | Evonik Operations Gmbh | Anlage zur Abtrennung von organischen Übergangsmetallkomplexkatalysatoren |
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US20090032465A1 (en) | 2009-02-05 |
ES2380937T3 (es) | 2012-05-21 |
ATE544506T1 (de) | 2012-02-15 |
DE102006003618A1 (de) | 2007-08-02 |
WO2007085321A1 (de) | 2007-08-02 |
KR101409786B1 (ko) | 2014-07-03 |
CA2640338A1 (en) | 2007-08-02 |
BRPI0621289A2 (pt) | 2011-12-06 |
EP1976619B1 (de) | 2012-02-08 |
JP2009524511A (ja) | 2009-07-02 |
PL1976619T3 (pl) | 2012-07-31 |
EP1976619A1 (de) | 2008-10-08 |
CN101360549A (zh) | 2009-02-04 |
KR20080089455A (ko) | 2008-10-06 |
TWI409282B (zh) | 2013-09-21 |
TW200740864A (en) | 2007-11-01 |
MY150775A (en) | 2014-02-28 |
CN101360549B (zh) | 2012-09-26 |
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