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Formic acid hi liquid hydrogen hun rei tak chhunga dahkhawmna atana candidate beisei awm ber pakhat a ni. Hetah hian sumdawnna lama hmuh theih emaw, awlsam taka siam chhuah emaw xanthos-type tridentate POP clamp ligand hmanga general formula [RuHCl(POP)(PPh3)] nei ruthenium clamp complex thar series kan rawn tarlang a ni. Heng complex te hi formic acid dehydrogenate turin kan hmang a, ionic liquid BMIM OAc (1-butyl-3-methylimidazolium acetate) chu solvent atan hmangin mild, reflux-free condition hnuaiah CO2 leh H2 siam chhuah a ni. Turnover frequency sang ber atanga thlir chuan catalyst tha ber chu literature-a hriat lar [RuHCl(xantphos)(PPh3)]Ru-1 complex a ni a, 90 °C-ah 10 min chhung turnover frequency sang ber 4525 h-1 a nei a ni. Conversion hnua rate chu 74% a ni a, darkar 3 chhungin conversion a zo (>98%). A lehlamah chuan, overall performance tha ber catalyst, novel [RuHCl(iPr-dbfphos)(PPh3)]Ru-2 complex hian 1 h chhungin complete conversion a tichak a, chu chuan overall turnover rate 1009 h-1 a siam a ni. Hei bakah hian 60 °C thlenga temperature-ah pawh catalytic activity hmuh a ni bawk. Gas phase-ah chuan CO2 leh H2 chauh hmuh a ni a; CO hmuhchhuah a ni lo. High-resolution mass spectrometry hmangin reaction mixture-ah hian N-heterocyclic carbene complex a awm tih hmuhchhuah a ni.
Renewable energy market share sang zel leh a danglamna hian power, thermal, industrial leh transport sector-ah industrial-scale energy storage technology mamawhna a tipung a ni1,2. Hydrogen hi energy carrier tam ber zinga mi anga ngaih a ni ,5,6 a ni. An taksa dinhmun avang hian gasoline leh liquid fuel dangte phurh chhuahna infrastructure awmsa tam zawk chu LOHC7,8 phurh chhuahna atan hman theih a ni. Formic acid (FA) physical property avang hian hydrogen dahkhawmna atana candidate beisei awm tak a ni a, hydrogen weight content 4.4%9,10 a ni. Mahse, formic acid dehydrogenation atana catalytic system tihchhuah tawhah chuan volatile organic solvent, tui emaw formic acid thianghlim emaw hman a ngai tlangpui a,11,12,13,14 chu chuan solvent vapor separation technique condensation ang chi hman a ngai thei a, hei hian consumer application-ah harsatna a thlen thei a ni. application te, additional load te pawh a awm bawk. He harsatna hi vapor pressure tlemte nei solvent, ionic liquid ang chi hmanga hneh theih a ni. Tun hmain kan working group chuan ionic liquid butylmethylimidazolium acetate (BMIM OAc) chu he reaction-ah hian solvent tha tak a nih thu hi sumdawnna lama hmuh theih fixing complex Ru-PNP Ru-MACHO type 15 hmangin kan lo entir tawh a, entirnan, BMIM OAc hmangin continuous flow system-ah FA dehydrogenation kan entir a, TON of over 18,000,000 at 95°C a ni. System thenkhat chuan a hmain TON sang tak nei mahse, tam tak chuan volatile organic solvent (THF emaw DMF ang chi) emaw additive hman (base ang chi) emaw an ring tlat a ni. Chumi danglamna chu kan hnathawh hian a takah chuan non-volatile ionic liquids (ILs) a hmang a, additives a hmang lo.
Hazari leh Bernskoetter te chuan dioxane leh LiBF4 awmnaah Fe-PNP catalyst hmangin 80 °C-ah formic acid (FA) dehydrogenation an report a, turnover number (TON) hmuhnawm tak chu 1,000,00016 vel a ni. Laurenci hian Ru(II)- complex catalyst TPPPTS chu FA dehydrogenation system kal zelah a hmang a. Hetiang hmang hian FA dehydrogenation tluantling deuhthaw a awm a, 80 °C17-ah CO hnuhma tlemte chauh hmuhchhuah a ni. He field hi hmasawn zawk nan Pidko chuan DMF/DBU leh DMF/NHex3 mixture-a Ru-PNP clamp catalyst hmanga FA reversible dehydrogenation a entir a, 90 °C18-ah TON value 310,000 atanga 706,500 a nei thei a ni. Hull, Himeda leh Fujita te chuan binuclear Ir complex catalyst an zirchiang a, chutah chuan KHCO3 leh H2SO4 te chu an inthawi a, CO2 hydrogenation leh FA dehydrogenation te chu an inthlak danglam a ni. An system hian 30°C-a hydrogenation, CO2/H2 (1:1), 1 bar pressure leh 60 leh 90°C19 inkar dehydrogenation atan TON 3,500,000 leh 308,000 chuang an hmu thei a ni. Sponholz, Junge leh Beller te chuan 90 °C20-a reversible CO2 hydrogenation leh FA dehydrogenation atan Mn-PNP complex an siam a.
Hetah hian IL approach kan hmang a, mahse Ru-PNPs hmang lovin Ru-POP catalyst hman dan kan zirchiang a, chu chu kan hriat dan chuan hemi kawngah hian a hmain kan la lantir ngai lo.
An metal-ligand coupling (MLC) tha tak avang hian Noyori-type concepts hmanga siam amino-PNP clamp complex te chu secondary amino functional group 21 (Ru-MACHO-BH ang chi) inzawmkhawm te nen a tlangpuiin molecule tenau operation thenkhatah an lar chho zel a ni. Entirna lar tak takte chu CO22, alkenes leh carbonyls te hydrogenation, transfer hydrogenation23 leh alcohols te acceptorless dehydrogenation24 te hi a ni. PNP clamp ligand-a N-methylation hian catalyst activity chu a titawp vek thei tih report a ni Mahse, tun hnaiah Beller-a’n formic acid dehydrogenation-a a kalh zawnga thil thleng chu a hmuchhuak a, chutah chuan N-methylated Ru-PNP complex-te chuan an unmethylated counterpart-te aiin formic acid-a catalytic dehydrogenation tha zawk an lantir tak zet a ni Complex hmasa kha amino unit kaltlangin MLC-ah a tel thei lo a, hei hian MLC, chuta tang chuan amino unit hian a hmaa ngaihtuah aiin (de)hydrogenation transformation thenkhatah hmun pawimawh lo zawk a chang thei tih a tilang chiang hle.
POP clamp nena khaikhin chuan POP clamp-a ruthenium complex te hi he hmunah hian zirchian a la ni tawk lo. POP ligand hi a hmain hydroformylation atan an hmang ber a, chutah chuan clamping ligand atan characteristic bidentate bite angle 120° vel ai chuan chelating ligand angin an thawk a, hei hi linear leh branched product-te selectivity tihchangtlun nan an hmang thin27,28, Chumi hnuah chuan Ru-POP complex hi hydrogenation catalysis-ah hman a ni tlem hle a, mahse transfer hydrogenation-a an hnathawh dan entirnan a hmain an lo sawi tawh a ni30. Hetah hian Ru-POP complex hi formic acid dehydrogenation atana catalyst tha tak a nihzia kan lantir a, hei hian Beller-a’n classical Ru-PNP amine catalyst-a amino unit chu he reaction-ah hian a pawimawh lo zawk tih a hmuhchhuah chu a nemnghet a ni.
Kan zirchianna hi general formula [RuHCl(POP)(PPh3)] nei typical catalyst pahnih siam chhuah atanga tan a ni (Fig. 1a). Steric leh electronic structure siam danglam turin sumdawnna lama hmuh theih 4,6-bis(diisopropylphosphino) (Fig. 1b) 31. He hnathawhnaa catalyst zirchian te hi Whittlesey32-a siam general method hmanga siam a ni a, [RuHCl(PPh3)3]•toluene33 adduct chu precursor atan hmangin siam a ni. Metal precursor leh POP clamp ligand te chu THF ah strictly anhydrous leh anaerobic condition hnuaiah mix la. Reaction hi dark purple atanga yellow-a rawng inthlak danglamna nasa tak nen a inzawm a, darkar 4 reflux emaw darkar 72 reflux 40°C-ah product thianghlim a pe a ni. THF chu vacuum-a lakchhuah a, hexane emaw diethyl ether hmanga vawi hnih silfai hnuah triphenylphosphine chu lakchhuah a ni a, quantitative yield sang takah yellow powder angin product chu a lo chhuak ta a ni.
Ru-1 leh Ru-2 complex siam chhuah. a) Complex siam dan. b) Complex siam chhuah (Synthesized complex) awm dan (structure).
Ru-1 hi literature atang hian hriat a ni tawh32 a, characterization dang pawh Ru-2 hi a ngaih pawimawh ber a ni. Ru-2 1H NMR spectrum chuan hydride pair ligand-a phosphine atom cis configuration chu a nemnghet a ni. Peak dt plot (Fig. 2a)-ah hian 2JP-H coupling constant 28.6 leh 22.0 Hz a awm a, hei hi report hmasa beisei angin a awm a ni32. Hydrogen decoupled 31P{1H} spectrum (Fig. 2b)-ah chuan 2JP-P coupling constant 27.6 Hz vel hmuh a ni a, hei hian clamp ligand phosphines leh PPh3 te hi cis-cis an nih thu a nemnghet a ni. Hei bakah hian ATR-IR hian 2054 cm-1-ah ruthenium-hydrogen stretching band ziarang a lantir bawk. Structural elucidation dang neih belh zel nan Ru-2 complex chu room temperature-a vapor diffusion hmangin X-ray study atana quality tling tak hmangin crystallized a ni (Fig. 3, Supplementary Table 1). Space group P-1 triclinic system-ah unit cell khatah cocrystalline benzene unit pakhat hmangin a crystallize thin. P-Ru-P occlusal angle zau tak 153.94° a nei a, hei hi bidentate DBFphos34-a 130° occlusal angle aiin a zau zawk hle. 2.401 leh 2.382 Å-ah chuan Ru-PPOP bond sei zawng hi Ru to PPh3 bond sei zawng 2.232 Å aiin a sei zawk tih a chiang a, hei hi a central 5-ring avanga DBFphos-a wide backbone snack angle avanga lo awm a ni thei. Metal center geometry hi a bul berah chuan octahedral a ni a, O-Ru-PPh3 angle chu 179.5° a ni. H-Ru-Cl coordination hi linear vek a ni lo va, triphenylphosphine ligand atanga angle 175° vel a ni. Atomic distance leh bond sei zawng chu Table 1-ah hian tarlan a ni.
Ru-2 atanga NMR spectrum hmanga siam a ni. a) Ru-H dt signal tarlanna 1H NMR spectrum-a hydrode region. b) 31 P{ 1 H} NMR spectrum-a triphenylphosphine (blue) leh POP ligand (green) atanga signal lo chhuak.
Ru-2 awm dan (structure) a ni. Thermal ellipsoids te hi 70% probability nen a lantir a ni. Fiah zawka hriat theih nan carbon chunga cocrystalline benzene leh hydrogen atom te chu paih chhuah a ni.
Complex-te’n formic acid an dehydrogenate theih dan tehna atan, reaction condition thlan a ni a, chutah chuan a inmil PNP-clamp complex (eg, Ru-MACHO-BH) te chu an active hle a ni15. Formic acid 0.5 ml (13.25 mmol) chu ruthenium complex Ru-1 0.1 mol% (1000 ppm, 13 μmol) hmanga dehydrogenation emaw, Ru-2 1.0 ml (5.35 mmol) ionic liquid (IL) BMIM OAc hmanga dehydrogenation (table-figure) 2 Figure 4-ah hian a lang a;
Standard hmuh nan chuan precursor adduct [RuHCl(PPh3)3]·toluene hmangin reaction chu an ti hmasa ber a. Reaction hi 60 atanga 90 °C thlenga tih a ni. Visual observation awlsam tak atanga a lan dan chuan 90°C temperature-a rei tak hrual pawhin complex hi IL-ah a inthiar kim thei lo a, mahse formic acid dah luh hnuah a inthiar chhuak ta a ni. 90°C-ah chuan minute 10 hmasa berah 56% (TOF = 3424 h-1) conversion a awm a, darkar thum hnuah almost quantitative conversion (97%) a awm (entry 1). Temperature 80 °C-a tihhniam hian min 10 hnuah conversion chu a chanve aia tam atanga 24%-ah a tihhniam a (TOF = 1467 h-1, entry 2), 70 °C leh 60 °C-ah 18% leh 18%-ah a tihhniam belh leh a, 6% (entry 3 leh 4) a ni. A zawng zawngah hian induction period hmuhchhuah a ni lo a, hei hian catalyst chu reactive species a ni thei tih emaw, reactive species inthlak danglamna chu a rang lutuk a, he data set hmang hian hriat theih a ni lo tih a tilang.
Precursor evaluation hnuah Ru-POP clamp complex Ru-1 leh Ru-2 te chu condition inangah hman a ni. 90°C-ah chuan conversion sang tak hmuh a ni nghal. Ru-1 hian experiment hmasa minute 10 chhungin 74% conversion a nei thei a (TOFmax = 4525 h-1, entry 5). Ru-2 hian activity a nei tlem hle a, mahse a inmil zawk a, min 10 chhungin 60% conversion a tipung (TOFmax = 3669 h-1) leh min 60 chhungin full conversion a tipung bawk (>99%) (entry 9). Hriat tur chu Ru-2 hi precursor metal aiin a sang zawk tih a chiang a, full conversion-ah Ru-1 a sang zawk bawk. Chuvangin, metal precursor leh Ru-1 te hian reaction zawh hunah TOFoverall value inang (330 h-1 leh 333 h-1, a hnuaia mi ang hian) an neih laiin, Ru-2 hian TOFoverall chu 1009 h-1 a nei a ni.
Chumi hnuah Ru-1 leh Ru-2 te chu temperature change an nei a, chutah chuan temperature chu 10 °C increment-in a tlahniam zauh zauh a, a tlem berah 60 °C thlengin an tlahniam ta a ni (Fig. 3). 90°C-ah complex chuan activity a lantir nghal a nih chuan darkar khat chhungin conversion tluantling deuhthaw a thleng a, chutah chuan temperature hniam zawkah chuan activity chu nasa takin a tlahniam a ni. Py-1 hi 80°C leh 70°C-a min 10 hnuah 14% leh 23% a ni a, min 30 hnuah 79% leh 73%-ah a pung (entries 6 leh 7). Experiment pahnihah hian darkar hnih chhungin conversion rate ≥90% a awm tih hmuhchhuah a ni. Ru-2 (entry 10 leh 11)-ah pawh hetiang bawk hian thil tih a ni. Ngaihven awm tak chu Ru-1 hi 70 °C-a reaction tawp lamah a dominant deuh a, a total TOF chu 315 h-1 a ni a, Ru-2 tan 292 h-1 leh metal precursor tan 299 h-1 a ni thung.
60 °C-a temperature tlahniam leh chuan experiment minute 30 hmasa berah conversion hmuh tur a awm lo. Ru-1 hi experiment tan tirh khan temperature hniam ber ah a inactive tih a chiang a, chumi hnuah chuan activity a tisang a, hei hian Ru-1 precatalyst chu catalytically active species ah a chantir theihna tur activation period mamawh a nih thu a tarlang. Hei hi temperature zawng zawngah tih theih ni mahse, experiment tan tirh atanga minute 10 chhung chu temperature sang zawka activation period hmuhchhuah nan a tawk lo. Ru-2 tan pawh hetiang bawk hian nungchang hi hmuh a ni. 70 leh 60 °C-ah chuan experiment hmasa min 10 chhung khan conversion hmuh tur a awm lo. Experiment pahnihah hian kan instrument detection limit (<300 ppm) chhungah carbon monoxide siam a ni lo tih hriat a pawimawh a, H2 leh CO2 chauh hi product hmuhchhuah a ni.
He working group-a a hmaa formic acid dehydrogenation result hmuh tawhte khaikhin chuan, state of the art aiawhtu leh Ru-PNP clamp complex hmanga siam thar hian Ru-POP clamp siam thar hian a PNP counterpart 15 nen activity inang a nei tih hmuhchhuah a ni. While clamp The PNP achieved RPMs of 500-1260 h-1 in batch experiments, the new POP clamp achieved a similar TOFovertal value of 326 h-1, leh Ru-1 leh 1590 h-1 te TOFmax value te hmuh a ni. an ni a, 1988 h-1 leh 1590 h-1 te an ni. Ru-2 chu 80 °C-ah 1 a ni a, Ru-1 chu 4525 h-1 a ni a, Ru-1 chu 90 °C-ah 3669 h-1 a ni.
Ru-1 leh Ru-2 catalyst hmanga formic acid dehydrogenation temperature screening neih a ni. Thil awm dan: Catalyst 13 μmol, formic acid 0.5 ml (13.25 mmol), BMIM OAc 1.0 ml (5.35 mmol) te a ni.
NMR hi reaction mechanism hriatthiam nan hman a ni. Hydrade leh phosphine ligand inkara 2JH-P hi a danglamna nasa tak a awm avangin he zirchianna hian a ngaih pawimawh ber chu hydride peak a ni. Ru-1 tan chuan hydrogenation unit-a dt pattern pangngai chu dehydrogenation minute 60 hmasa berah hmuh a ni. Downfield shift nasa tak awm mahse −16.29 atanga −13.35 ppm thlenga inthlak danglamna nasa tak awm mahse, phosphine nena a coupling constant chu 27.2 leh 18.4 Hz a ni (Figure 5, Peak A). Hei hi hydrogen ligand cis configuration-a awm phosphine pathumte nen a inmil vek a, optimized reaction condition hnuaiah darkar khat vel IL-ah hian ligand configuration chu a stable deuh tih a tilang. Downfield shift chak tak hi chlorinated ligand tihbo leh a inmil acetyl-formic acid complex siam vang te, NMR tube-a d3-MeCN complex in situ a lo awm vang te, a inmil N-heterocycle siam vang te pawh a ni thei. tiin a hrilhfiah a. Carbene (NHC) hmanga siam a ni. Dehydrogenation reaction lai hian he signal chakna hi a tlahniam zel a, minute 180 hnuah pawh signal hi hmuh tur a awm tawh lo. Chu ai chuan signal thar pahnih an hmuchhuak ta zawk a ni. A hmasa ber hian -6.4 ppm (peak B)-a thleng dd pattern chiang tak a tarlang. Doublet hian coupling constant lian tak 130.4 Hz vel a nei a, hei hian phosphine unit pakhat chu hydrogen nena khaikhin chuan a kal tih a tilang a ni. Hei hian POP clamp chu κ2-P,P configuration-ah a insiam thar tihna a ni thei. Catalysis hnu lama he complex lo lang hian he chi hian hun kal zelah deactivation pathways a thlen a, catalyst sink a siam tih a tilang thei. A lehlamah chuan chemical shift hniam tak hian dihydrogenous species a ni thei tih a tilang15. Peak thar pahnihna chu -17.5 ppm-ah a awm a ni. A fold hi hriat ni lo mah se, triplet a nih kan ring a, coupling constant tlem 17.3 Hz a nei a, hei hian hydrogen ligand hian POP clamp-a phosphine ligand chauh a binding tih a tilang a, hei hian triphenylphosphine (peak C) chhuahna a tilang bawk. Ligand dang, acetyl group emaw, ionic liquid atanga in situ-a siam NHC emaw hmanga thlak theih a ni. PPh3 dissociation chu -5.9 ppm-a singlet chak tak hian a tilang lehzual a ni. 90 °C-a minute 180 hnuah Ru-1 31P{1H} spectrum-ah (thu belhchian dawl zawk en rawh).
Formic acid dehydrogenation laiin Ru-1 1H NMR spectrum a hydrode region a awm a. A rilru a hah lutuk chuan a rilru a buai em em a, a rilru a hah lutuk chuan a rilru a buai em em bawk a. 0.5 ml formic acid, 1.0 ml BMIM OAc, 13.0 μmol catalyst, 90 °C. NMR chu MeCN-d 3 atanga lak a ni a, deuterated solvent 500 μl, reaction mixture 10 μl vel a ni.
Catalytic system-a active species awm leh awm loh finfiah lehzual nan Ru-1 chu 90 °C-a formic acid injection hnuah high resolution mass spectrometry (HRMS) analysis an nei a. Hei hian reaction mixture-ah hian chlorine ligand precatalyst nei lo chi hrang hrang a awm tih a tilang a ni. tin, NHC complex pahnih, an putative structures chu Figure 6-ah hian tarlan a ni a, a inmil HRMS spectrum chu Supplementary Figure 7-ah hian kan hmu thei bawk.
Heng data atang hian Beller-a rawtna ang chiah intrasphere reaction mechanism kan rawt a, chutah chuan N-methylated PNP clamps te chuan reaction inang chu an catalyze a ni. Ionic liquids tel lovin experiment dang pawh a awm lo va, chuvangin a direct involvement a ngai niin a lang. Ru-1 leh Ru-2 activation hi chloride dissociation hmanga thleng a ni tih kan hypothesis a, chu chu NHC addition awm thei leh triphenylphosphine dissociation hmangin a thleng a ni (Scheme 1a). Hetiang activation hi species zawng zawngah hian a hmain HRMS hmangin hmuhchhuah a ni tawh. IL-acetate hi formic acid aiin Bronsted base a chak zawk a, a hnuhnung zawk hi nasa takin a deprotonate thei a ni35. Kan hypothesis chu catalytic cycle (Scheme 1b) chhung hian active species A bearing NHC emaw PPh3 emaw chu formate hmangin coordinate in species B an siam a, he complex hi C-ah reconfiguration a nih chuan a tawpah chuan CO2 a chhuak a, trans-dihydrogen complex D chu a hnu lama acid chu a hmaa acetic acid siam tawh nen dihydro complex-a protonation-a dihydro complex E siam a ni Beller-a’n N-methylated PNP clamp homologues hmanga key step a rawt nen a inang. Chu bakah, a hmain complex EL = PPh3 analogue chu sodium salt hmanga chloride lakchhuah hnuah hydrogen atmosphere-a Ru-1 hmanga stoichiometric reaction hmangin an lo siam tawh bawk. Hydrogen lakchhuah leh formate coordination hian A a pe a, cycle chu a zo ta a ni.
Fixing complex Ru-POP Ru-1 hmanga formic acid dehydrogenation intrasphere reaction atana mechanism siam a ni.
Complex thar [RuHCl(iPr-dbfphos)(PPh3)] siam chhuah a ni. He complex hi NMR, ATRIR, EA leh X-ray diffraction analysis hmangin single crystals te chu an zirchiang a ni. Formic acid chu CO2 leh H2-a dehydrogenation-a Ru-POP pincer complex hman hlawhtling hmasa ber kan report bawk. Metal precursor hian activity inang (3424 h-1 thleng) nei mahse, complex hian 90 °C-ah turnover frequency sang ber 4525 h-1 thleng a thleng a ni. Chubakah, 90 °C-ah chuan complex thar [RuHCl(iPr-dbfphos)(PPh3)] hian a thlawh hun zawng zawng (1009 h-1) a ti thei a, formic acid dehydrogenation a ti zo a, hei hi metal precursor (330 h-1) aiin a sang zawk hle. leh a hmaa an lo report tawh complex [RuHCl(xantphos)(PPh3)] (333 h-1) te an ni. Hetiang dinhmunah hian catalytic efficiency hi Ru-PNP clamp complex nen tehkhin theih a ni. HRMS data chuan reaction mixture-ah hian carbene complex a awm tih a tarlang a, a tlem hle nachungin. Tunah hian carbene complex te hian catalytic effect an neih dan kan zirchiang mek a ni.
He zirchianna chhunga data hmuh emaw, zirchian emaw zawng zawng hi he thuziak chhuah tawhah hian [leh a thlawptu information file-ah] dah vek a ni.
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