Name: heterogeneous removal of water-soluble ruthenium olefin metathesis catalyst from aqueous media via host-guest interaction
Uploaded: 2018-08-23T14:00:00
Description: Watch this Scientific Journal Video about Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction Video at JoVE.com

Dette arbeidet ble støttet av Florida State University energi og materialer ansette initiativ og FSU avdeling av kjemiske og biomedisinsk Engineering.

Merk: Vi presentert syntese av 4-(97-(adamantan-1-yloxy)-2,5,8,11,14,17,20,23,26,29,32,35,38,41,44,47,50,53,56,59,62,65,68,71,74,77,80,83,86,89,92,95-dotriacontaoxaheptanonacontyl)-1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium tetrafluoroborate (imidazolium salt A) og vert komplekse, podet β-CD silika, i vår forrige papir38. I protokollen beskriver vi en syntese av våre vannløselige Ru olefiner metathesis katalysator og metathesis reaksjoner (Vedlikeholdsstyring og BOLTRE).
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Vi beskrev syntesen av flyttbare homogen Ru olefiner metathesis katalysator og fjerning fra både vann- og økologiske løsninger. Homogen katalyse gir mange fordeler sammenlignet med heterogene katalysatorer, som høy reaktivitet og rask reaksjon rate; fjerning av brukt katalysator fra produktet er imidlertid vanskeligere enn heterogene katalysator3. Nøkkelen ansiktstrekk av syntetisk katalysator er NHC ligand, som bærer adamantyl bundet vann løselig oligo(ethylene glycol). Presentert katalysa...

Fjerning av homogen organometalliske katalyse fra produktet er en viktig sak i moderne kjemi1,2. Rester av katalysator forårsaker ikke bare et toksisitet problem fra det heavy metal-elementet, men også en uønsket endring av produktet fra sine potensielle reaktivitet. Homogen katalysator gir mange fordeler, for eksempel høy aktivitet og rask reaksjon hastighet chemoselectivity3, men fjerning fra produktet er mye vanskeligere enn heterogene katalysator som fjernes bare ved filtrering eller decantation. Kombinasjonen av fordelene av homogen og heterogen katalysator, dvs, homogen reaksjon og heterogene fjerning, representerer viktig begrep for svært reaktive og lett tas organometalliske katalysator. Figur 1 illustrert the Arbeidsprinsipp for homogen reaksjon og heterogene fjerning av katalysator via host-gjest interaksjon.
Host-gjest kjemi er noncovalent bonding molekylær anerkjennelse mellom verten molekyler og gjest molekylene i supramolecular kjemi,4,,5,,6,,7,,8. Syklodekstriner (CD), syklisk oligosaccharides, er representativt vert molekyler9,10,11,12, og de er brukt i brede områder av vitenskap som polymer vitenskap 13 , 14, katalyse15,16, biomedisinsk programmer6,10og analytisk kjemi17. En gjest molekyl, adamatane, binder sterkt hydrofobe hulrommet av β-CD (vert, 7 medlemmer syklisk monosakkarid (sukker)) med høy association konstant, Ken (logge Ken = 5,04)18. Denne supramolecular forpliktende tilhørighet er sterk nok til å fjerne rester av katalysator komplekse fra vandig reaksjon løsning med solide støttes β-CD.
Blant mange katalysatorer som er kvalifisert for vert-gjest fjerning, ble Ru olefiner metathesis katalysator studert høy praktiske verktøy og høy stabilitet mot luft og fuktighet. Olefiner metathesis reaksjonen er viktig for syntetiske kjemi å danne et karbon-karbon dobbelt bånd i nærvær av et transisjonsmetall katalysator19,20,21,22. Utviklingen av stabil Ru olefiner metathesis katalysator trigged metathesis som store felt syntetiske kjemi (f.eks, Vedlikeholdsstyring og tvers metathesis (CM)) og polymer vitenskap (f.eks, TUMLE og den asykliske diene metathesis (ADMET)). Spesielt syntetiserer Vedlikeholdsstyring macrocycles og mellomstore ringer som er vanskelig å bygge23.
Til tross for syntetiske verktøy av Ru katalysert olefiner metathesis er fullstendig fjerning av brukt Ru katalysator fra det ønskede produktet en stor utfordring for mange praktiske anvendelser24. For eksempel ble 1912 ppm Ru rester observert i ring-avsluttende metathesis produkt etter silica gel kolonnen kromatografi25. Gjenværende Ru kan forårsake problemer som olefiner isomerization, nedbryting, fargelegging og toksisitet av legemidler26. Internasjonal konferanse om harmonisering (ICH) publisert en retningslinje gjenværende metall reagenser i legemidler. Maksimalt Ru nivå i farmasøytisk produkt er 10 ppm27. For disse grunner, var ulike tilnærminger prøvde å fjerne Ru rester produkt løsning28,29,30,31,32,33. Også har utviklingen av flyttbare Ru katalysatorer vært studert for rensing uten spesiell behandling etter reaksjon. Blant ulike metoder for rensing, ble katalysator ligand modifikasjoner prøvde å forbedre effektiviteten av silica gel filtrering og flytende utvinning. For eksempel kan høyeffektive silica gel filtrering oppnås ved introdusert ion kode på benzylidene34 eller ryggraden i NHC ligand35,36. Katalysator betydning poly(ethylene glycol)37 eller ion tag35 en NHC ligand kan forbedre effektiviteten i vandig utvinning Ru katalysator fjerning.
Nylig rapportert vi en svært vannløselige Ru olefiner metathesis katalysator, som viste ikke bare høy reaktivitet, men også høy katalysator fjerning rate. Videre oppstod metathesis og katalysator fjerning i både vann og diklormetan34,35,36,37. Nøkkelen ansiktstrekk av nye katalysatoren er at nye NHC bærer adamantyl bundet oligo(ethylene glycol). Oligo(ethylene glycol) gir høy vannløselighet av hele katalysator komplekse. I tillegg besitter til oligo(ethylene glycol) adamantyl slutten gruppe som kan brukes i vert-gjest interaksjon med eksterne β-CD.
Her, beskrev vi protokollene for katalysator syntese, metathesis reaksjoner og katalysator fjerning både vann og diklormetan.

<table border="0" cellpadding="0" cellspacing="0" style="width:767px;" width="767">
	<tbody>
		<tr height="21">
			<td height="21" style="height:21px;width:283px;">Hoveyda-Grubbs Catalyst 1st Generation</td>
			<td style="width:160px;">Sigma-Aldrich</td>
			<td style="width:157px;">577944</td>
			<td style="width:167px;">Air sensitivie. Light sensitivie.</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:283px;">Diethyl diallylmalonate</td>
			<td style="width:160px;">Sigma-Aldrich</td>
			<td style="width:157px;">283479</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:283px;">Ethyl vinyl ether</td>
			<td style="width:160px;">Sigma-Aldrich</td>
			<td style="width:157px;">422177</td>
			<td>Air sensitive.</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:283px;">Aluminum oxide</td>
			<td style="width:160px;">Sigma-Aldrich</td>
			<td style="width:157px;">06300</td>
			<td>Activated, neutral, Brockmann Activity I</td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:283px;">Potassium bis(trimethylsilyl)amide solution (0.5 M in toluene)</td>
			<td style="width:160px;">Sigma-Aldrich</td>
			<td style="width:157px;">277304</td>
			<td>Moisture sensitive.</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:283px;">Etyhl acetate</td>
			<td style="width:160px;">VWR</td>
			<td style="width:157px;">BDH1123</td>
			<td>Flammable liquid.</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:283px;">Methanol</td>
			<td style="width:160px;">VWR</td>
			<td style="width:157px;">BDH1135</td>
			<td>Flammable liquid. Toxic.</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:283px;">Deuterium Oxide 99.8%D</td>
			<td style="width:160px;">TCI</td>
			<td style="width:157px;">W0002</td>
			<td></td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:283px;">Methylene Chloride-D2 (D, 99.8%)</td>
			<td style="width:160px;">Cambridge Isotope Laboratories, Inc.</td>
			<td style="width:157px;">DLM-23</td>
			<td>Flammable liquid. Toxic.</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:283px;">Activated carbon</td>
			<td style="width:160px;">Sigma-Aldrich</td>
			<td style="width:157px;">242276</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:283px;">Magnesium sulfate</td>
			<td style="width:160px;">EMD Millipore</td>
			<td style="width:157px;">MX0075</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:283px;">Ethyl ether</td>
			<td style="width:160px;">EMD Millipore</td>
			<td style="width:157px;">EX0190</td>
			<td>Flammable liquid.</td>
		</tr>
	</tbody>
</table>

heterogeneous removal of water-soluble ruthenium olefin metathesis catalyst from aqueous media via host-guest interaction

En svært effektiv transisjonsmetall katalysator fjerning metoden er utviklet. Vannløselige katalysator inneholder en nydesignede NHC ligand katalysator fjerning via host-gjest interaksjoner. Nye NHC ligand har et adamantyl (gjest) bundet lineær etylenglykol enheter for hydrofobe inkludering i hulrommet mengden β-cyclodextrin (β-CD) sammensatte. Nye NHC ligand ble brukt til en Ru-baserte olefiner metathesis katalysator. Ru katalysator vist gode aktivitet i representant ring-avsluttende metathesis (Vedlikeholdsstyring) og ring-åpning metathesis polymerisasjon (BOLTRE) reaksjoner i vandige media samt organisk løsemiddel, lm2Cl2. Etter reaksjonen var ferdig, langvarig Ru rester ble fjernet fra vandig løsning med effektiviteten av mer enn 99% (53 ppm Ru rester) av enkle filtrering bruker en vert-gjest samhandling mellom uløselig silika-podet β-CD (vert) og adamantyl moiety (gjest) på katalysator. Den nye Ru katalysatoren viste også høy renseeffekt via utvinning når reaksjonen kjøres i organiske løsemidler ved deling rå reaksjonsblandingen mellom lag av diethyl Eter og vann. På denne måten forblir katalysator i vandig lag. I organisk lag var gjenværende Ru mengden bare 0,14 ppm i Vedlikeholdsstyring reaksjonene av diallyl forbindelser.

Figur 2 beskriver ligand exchange reaksjonen for våre katalysator 1. 1H-NMR spekteret er vist i Figur 3.
Figur 4 viser Vedlikeholdsstyring i vandig løsning og påfølgende fjerning av brukt katalysator fra reaksjonsblandingen via host-gjest samhandling, og tabell 1 oppsummerer Vedlikeholdsstyri...

Watch this Scientific Journal Video about Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction Video at JoVE.com

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction Video (Video) | JoVE

En flyttbar vannløselige N-hetrosyklisk carbene (NHC) ligand i vandige media via host-gjest samhandling er utviklet. Vi viste representant olefiner metathesis reaksjoner i vann også som diklormetan. Enten via host-gjest interaksjon eller utvinning var gjenværende ruthenium (Ru) katalysator så lavt som 0,14 ppm etter reaksjon.

Heterogen fjerning av vannløselige Ruthenium olefiner Metathesis Catalyst vandige Media Via Host-gjest interaksjon

A highly efficient transition metal catalyst removal method is developed. The water-soluble catalyst contains a newly-designed NHC ligand for the catalyst ...

Research

JoVE Journal

Chemistry

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia

Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia Video (Video) | JoVE

Utarbeidelse av hydrofobe Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Nedfall av Perfluoroalkanes for fjerning av ammoniakk

Plasma enhanced chemical vapor deposition (PECVD) of perfluoroalkanes has long been studied for tuning the wetting properties of surfaces. For high ...

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes Video (Video) | JoVE

The Synthesis, Characterization og reaktivitet av en serie av Ruthenium<em&gt; N</em&gt; -triphos<sup&gt; Ph</sup&gt; Komplekser

Herein we report the synthesis of a tridentate phosphine ligand N(CH2PPh2)3 (N-triphosPh) (1) via a phosphorus based Mannich reaction of the ...

Water in Oil Emulsions: A New System for Assembling Water-soluble Chlorophyll-binding Proteins with Hydrophobic Pigments

Water in Oil Emulsions: A New System for Assembling Water-soluble Chlorophyll-binding Proteins with Hydrophobic Pigments Video (Video) | JoVE

Vann i olje emulsjoner: Et nytt system for Montering Vannløselige Klorofyll bindende proteiner med Hydrofobe Pigmenter

Chlorophylls (Chls) and bacteriochlorophylls (BChls) are the primary cofactors that carry out photosynthetic light harvesting and electron transport. ...

HKUST-1 as a Heterogeneous Catalyst for the Synthesis of Vanillin

HKUST-1 as a Heterogeneous Catalyst for the Synthesis of Vanillin Video (Video) | JoVE

HKUST-en som en heterogen katalysator for syntese av Vanillin

Vanillin (4-hydoxy-3-methoxybenzaldehyde) is the main component of the extract of vanilla bean. The natural vanilla scent is a mixture of approximately ...

Synthesis of a Water-soluble Metal&#8211;Organic Complex Array

Synthesis of a Water-soluble Metalâ€“Organic Complex Array Video (Video) | JoVE

Syntese av en vann-løselig metall-organisk kompleks rekke

We demonstrate a method for the synthesis of a water-soluble multimetallic peptidic array containing a predetermined sequence of metal centers such as ...

Synthesis and Evaluation of a Ruthenium-based Mitochondrial Calcium Uptake Inhibitor

Synthesis and Evaluation of a Ruthenium-based Mitochondrial Calcium Uptake Inhibitor Video (Video) | JoVE

Syntese og evaluering av en Ruthenium-baserte mitokondrie kalsium opptak hemmer

We detail the synthesis and purification of a mitochondrial calcium uptake inhibitor, [(OH2)(NH3)4Ru(&#181;-O)Ru(NH3)4(OH2)]5+. The optimized synthesis of ...

Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction

Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction Video (Video) | JoVE

Syntese og ytelse karakteristikkene av transisjonsmetall enkelt Atom katalysator elektrokjemiske CO2 reduksjon

This protocol presents both the synthesis method of the Ni single atom catalyst, and the electrochemical testing of its catalytic activity and selectivity ...

Preparation of Polyoxometalate-based Photo-responsive Membranes for the Photo-activation of Manganese Oxide Catalysts

Preparation of Polyoxometalate-based Photo-responsive Membranes for the Photo-activation of Manganese Oxide Catalysts Video (Video) | JoVE

Utarbeidelse av Polyoxometalate-baserte Foto-responsive membraner for foto-aktivering av mangan oksid katalysatorer

This paper presents a method to prepare charge-transfer chromophores using polyoxotungstate (PW12O403-), transition metal ions (Ce3+ or Co2+), and organic ...

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization Video (Video) | JoVE

Photogeneration av N-hetrosyklisk Carbenes: programmet i Photoinduced Ring-åpning Metathesis polymerisering

We report a method to generate the N-heterocyclic carbene (NHC) 1,3-dimesitylimidazol-2-ylidene (IMes) under UV-irradiation at 365 nm to characterize IMes ...

Multiscale Sampling of a Heterogeneous Water/Metal Catalyst Interface using Density Functional Theory and Force-Field Molecular Dynamics

Multiscale Sampling of a Heterogeneous Water/Metal Catalyst Interface using Density Functional Theory and Force-Field Molecular Dynamics Video (Video) | JoVE

Multiscale utvalg av en heterogen vann/Metal katalysator grensesnitt ved hjelp av tetthet funksjonelle teori og Force-feltet molekylære dynamikk

A significant number of heterogeneously-catalyzed chemical processes occur under liquid conditions, but simulating catalyst function under such conditions ...