ࡱ> pro9 RObjbj2~'l&&&&&&&:4"t:.^$  &&&a&&v&& A To:w0  ::&&&&Progress of the carbonylation synthesis with Rhodium or Iridium catalysts Jiang Dazhi (Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080) Abstract Progress on the synthesis of acetic acid and acetic anhydride by the Rhodium or Iridium catalyzed carbonylation, particularly during the last fifteen years or so, and the comparison of the Rhodium- or Iridium-based catalysts in some relative aspects were summarized. Keywords Acetic acid, Acetic anhydride, Carbonylation, Rhodium, Iridium catalyst є0PSWTbb/gۏU\  HYPERLINK "mailto:jiangdz@iccas.ac.cn" 'Yzf (-NVyf[bSf[xvz@b,SN100080) WTb ]/fS_MRhQtxTP]Nv;NAmb/g0 NN~90t^NR(WbNv kQN ;esQR-N0cQO`bV]vb/gy{^10N(T/t^WTbxuN~vR_Y0RN)Y bVvx]Nb]~SuN9h,g'`vlSǑ(uWTbb/g^0_ۏT-NYTDP4Yv^ۏ (W10Yt^vȇ ObVvxNϑNV P؏Y ;`Nя200N(T/t^ (W*gegv2~3t^̑u󁁉0R300N(T/t^N N0(WP]Neb bVO`;NwƋNCgb/g]N2003t^5g(W_lς9N3_N^zNNagPWTbՋuN~ 2007t^-N sSSibN0R8-10N(T/t^0ُhfNbVvxTPvWTb]Nb/g s]PNNLuHQۏV[LR0я10Yt^eg @wxTPvWTb] zyvvv~/TR VQ(WُNWvxvzTb/g_S]\O_NfR;mÍweg0,gee(W[VQYє0PSWTbb/gۏU\NNi v^cbVxTPvWTbb/gvSU\R0 WTbluNxTPvPSBRSO|SvQv^]z ;`SOeg SNR:N$N'Y{|[1] sSx'`PSBRSO|vKochxckyP[SS^~Tg!eё^\WSTir/dS }PSBRSO|vReppe~TPSSS^~0є0PSWTb [E N/fcTNySS^~0(W~TPSWTb]z-N mvSO|є0PSBRvO(uHegg}Y0,ge;NN~є0PSBRmvlWTbb/gۏU\TSU\R0 10єPSWTbvS^:gt (WǑ(ug!eё^\WSTirNdS }bdS }STirPSBRSO|agN N 1u2u0x2uoTN2uI{2u'lWSTirTbxTPvWTb RYS^6k@b~Sv[hQ/f TN*NPS_sǏ z[2] CH3X + CO  INCLUDEPICTURE "http://www.chemistrymag.org/cji/2007/images/09401501.gif" \* MERGEFORMATINET CH3-CO-X XCl, Br, I 1 sSHQubYNpdSSir T/fxTPqQ TvMRSOSTir0\O:NRPSBRvdS }bdS }STir vQRPS\O(u gY Nz^ sSI>Br>Cl0 sNxTPvWTb]N-NnfMǑ(uvєWSTir/x2upPSBRSO|:NO egfُNPS_sǏ zTWTbS^:gt  INCLUDEPICTURE "http://www.chemistrymag.org/cji/2007/images/09401502.gif" \* MERGEFORMATINET  V1 є/xPSWTbS^:gt (WُNPS_sǏ z-N@bNuvYNpx N2ub4lS^ubx Nx2uobxvS^RubP0#I{N[3] Ǒ(uϑP[Sf[ gHe8hRяf]_0xvzSs CH3I[[Ir(CO)2I2]- v'lSRb k[ [Rh(CO)2I2]- v'lSRb_~150 P [c NegvyceQS^ [MeRh(CO)2I3]- tSk [MeIr(CO)2I3]- _105-106 P0ُ1\/f PS2uSvPS_s-N 'lSRb NQ/fbaS^ yceQS^Mb/fcek0PS_svyceQS^ S+T gN*NxyP[I- N [MeIr(CO)2I3]- -N㉻yQeg N*NCOۏeQMMO NS2uWy0ُ̑gbavS^ek/f-NSO a!'! b!'vlS vQ-NSbxyP[I- v㉻yTCOۏeQMMO2uWTz_MOvCOMSOy /fgvQŏv0N/f /xPSWTbvS^RRf[e zO/f r = k . [Ir] . [CO] / [I-] sSSS^^rNPSBRSm^TCOSm^bckk NxyP[Sm^bSk0 h2 є0PS_ssQ.S^Ǐ z;mSSpe S^Ǐ z;mSpqDH`" kJ/mol;mSqDS`" J/(mol.K)'lSRbRh-AcOH60-50 [9,10]-120- -165 [9,10]Rh-AcOAc46 [9]-180 [9]Ir-AcOH54[11]-113[11]yceQRh-AcOH63[10]-59[10]Ir-AcOH33[12]-197[12] h2 RQN1u!jWS^Km[vє0PS_s-NsQ.S^Ǐ zv;mSSpe0ُNpenchfN(WєPSWTbxRh-AcOH bPRh-AcOAc -N 'lSRbv;mSMOWkPSWTbxIr-AcOH vؚvY є/xPSagN Nv'lSRb/fte*NPSSS^v^Q[ek (WPSagN NyceQv;mSMOW vS kєPSvؚvY Q[N/xPSagN NvyceQS^/fte*NPSSS^vbaek0MRbc0Rvegv/xPS1u2uSTbxKm[vDG`" 1uN N/f(WgOSagN NۏLv[ ~gO g@bOPؚ FONPSWTbxǏ z-NbaS^v;mSMOWN N1YvQSk'`0 N/xPSWTbvS^RRf[e zr = k . [Ir] . [CO] / [I-] SN Y(W-NSO a!'! b!'lSُNekOSRdSxSirviry 1\SN\O:NOۏBRbRPSBRO(u0xvzcQ k}YvOۏBRbRPSBR g$N{|ё^\STirN{|/f 0I0^l0STߔvUS~vxSir SN{|/f00TvW-xMTir0 h3RQNRmRBR[2uWTbS^svq_T0[hf ReQ^ё^\STirmRBRn-Bu4NI S gvPS;m'`S S0R%N͑vQ1_(Wё^\STirmRBR-N Ru(CO)4I2\O:N/xPSBRSO|vOۏBR vQHegg}Y0 h3 TymRBR[2uWTbS^svq_T SmRBR[ [Ir] id\kSTY mol/L/h1zz}v[kՋ 0:18.22n-Bu4NI1:12.73LiI1:14.3.4Ru (CO)4I25:121.65Os (CO)4I25:118.66CdI25:114.77InI35:114.88InI3 / Ru (CO)4I25:1:119.49Ru (CO)4I21:0e 0 xvz:N Ru(CO)4I2I{ё^\OۏBRvcSN0RPS_sS^KN-N b_bN*NRPS!k~_s[7]  INCLUDEPICTURE "http://www.chemistrymag.org/cji/2007/images/09401504.gif" \* MERGEFORMATINET  V3 PSSSO|-Nё^\OۏBRvRPS:gtnBR:N4lb2u sSnBRSvё^\OۏBRM(CO)xIy(solv) gRNMNOyceQS^v;mSMOW O[MeIr(CO)2I3]- f[f㉻yQI- v^ObCOۏeQfeNKNMMO N OPSWTbvte*NPS_sǏ z^_Ncؚ0[cQ (WPS2uSTbxS^SO|-N mRx2uoS>fW0WRS^ NmRϑSN_ؚ0(WV3@b:yvRPS!k~_s-N OyP[`vё^\OۏBR [M(CO)xIy+1]-[H]+ b` Y0RvQRY` [M(CO)xIy(solv)] Ǒ(ux2uokO(u2uf:N g)R ُ7h NOV:NmdxyP[0 ~SO| bǏYv4l+Tϑ0Q0Rx2uoSNv g:gS^s^a PSWTbvS^RRf[e z1\Sb r = k . [Ir] . [CO] . [MeOAc] sSSS^^rNPSBRSm^0COSm^Tx2uoSm^bckk0penchf Ǒ(uPSWTbx@b0Rvg}YvPSS^s:N2.0103 mol AcOH/(mol Ir.h)[7]0 30є0PSWTb]zk є0PSWTb]z 1uNPS_sTS^RRf[v]_ [(W_Yeb g N TKNY0MonsantolQSxvzNXT[13]e(WNNSfєPSBRg 1\[є0ُ$NyPSBR(uNxvWTbvyr'`ZPNk0яt^eg ѐObI{[14][PSBRvCativa]zNєPSBRvMonsanto]zvNNq_TV }_NۏLN[k0,geb~Tُ$NyPSBR(uNxTPvWTbя10Yt^egvSU\ 1\WTbSO|-NNN͑~Rvq_T0~є0PSBRv N Ths NS1udk bvُ$NyWTb]zvO:p0 1 SSO|+T4lϑ ;`SOeg 1uNє0PSBRSvQ;m'`iry/fv{|ir( S^SO|-N g4lX[(W [Ncؚ[Nvn'`/f g)Rv0FOSS^kz/fY(W_ YBgvsXKN-N S^SO|-N gN~Rv^ NU"k4l OYubvP1\ NG0R4l &TR1\SV0RxN0 (WPvWTbSO|-N SR N N g4l0FO\(WSS^6k Yg g\ϑ4lX[(W N,0W ]zd\O'`1\O g'Yv9eU0NNُNpeg xTPTN]zf g@b9eU[16,17]0Ǒ(ubNvYc[vBg.TWєMTirPSBRvWTb]z[18,19] Tbxe[S^SO|v+T4lϑBlSNM0R5~6 wt.% S^sSN0R6.6103 mol AcOH/(mol Rh.h) SNir b'`Oc(W99%N N0 ُ{|єPSBR(uNx2uobN2uSTbPe SSO|-Ne4l PSS^sSN0R2.8103 mol AcOAc/(mol Rh.h) SNir b'`cя100%0 2 x2uoSm^vq_T (WSS^SO|-N ReQx2uoT/bN2u N,0W /f:NNTbP0FOSO|-N g4lb[fNu4lvire0Y2u02uxb2ux2uoI{X[(W 1\ NO gPub[15]0 Ǒ(uєPSBRۏLWTbe YgTbv/fP x2uoeu/f;NvS^ire YgTbv/fx SN NRx2uo0x2uoSm^(W1 wt.%N Ne NOq_TPSS^s01udk weg x2uoRYNev V:NُeSO|-Nv2uSm^1\Ov^MNO Oq_T0RxvezzNs0SNeb SO|-Nx2uoǏY єPSBRvn'` N}Y O gRєPSBRlmub0 (WPSvWTbxSO|-N NS^RRf[e zr = k . [Ir] . [CO] . [MeOAc]eg w x2uoRYN S^^_0[hf (WPSvWTbxSO|-N x2uoSm^SNkєPSWTbSO|-NvؚQ_Y0x2uo(WPSWTbxSO|-Nv;N\O(u/f NHIS^ OSRё^\OۏBR[sRPS!k~_s0PSBR(Wx2uo-Nvn'`kєPSBRv}YvY0(WPSvWTbmSOS^ire-N dNx2uoKNY ؏ g2u04lTx2upI{0YgS^irȇl gN4lT2u _N1\ NS gxub0HN ُeO NOb_bPbTT{Hh/f _ b _\ V:NPS_sNuvYNpxNx2uovcS^v;mSMOW_ؚ :\xv{|SN Pvub^O/f^8^bav0 3 x2upSm^vq_T Ǒ(u~TPSWTb]z~TbxTP x2up/f_ NS\vg;NvRPSBR /fSS^PS_sv;N҉0 ُsSO(WPSWTbx-N_N NOY0S/f(WPSSO|-N x2up(uϑ_\ N,(W6 wt.%N Ne PSS^^NvQSm^MbHTckvsQ0 [NєPSSO| S^RRf[e z]cQ PSS^^/fx2upSm^ NGSv0(WPSSO|-N x2up(uYN NFOev S g[0FO(WєPSSO|-N `QRvS0u gN)RcQ[20] Sbx2up(WQvxSm^ؚN gRNcؚєPSBRSO|vp'` O gSubvp N3z[v[Rh(CO)I4]- lSbp3z[v[Rh(CO)I5]2-0ُ{N)R^ (WєPSSO|-N ^OcI/Rhid\k:N20bfY0 4 N'lSxRSvq_T NS^RRf[e z w CO[NPSSO|v͑'` k[єPSBRSO|v'YvY0(WєPSBRSO|-N z gN[vCORST PSS^sONCORSesQ0 (WPSBRSO|-N PSS^sCORSHT~'` NGSR0CORSGS0R0.8 MPaN Ne ُy~'` NGSRMbOS0ѐObI{v[[21]؏cQ (WPSS^SO|-N XRCORS g)RNQ\ubN2uI{oRS^ cؚNirxv b'`0 5 PSBRSm^ (WSS^SO|-N OcєPSBRYNo}Yvn㉶r` vQSm^g}Yc6R(W400~800 ppmVQ gY NQ1000 ppm [PSBReg vQSm^SN0R3000~4000 ppm,u6000 ppm0єPSBR(WS^SO|-NvSm^0R600 ppmN Ne NezzNsSTY vPSS^s[PSBRSm^v~'`XsQ|1\>fW0W vQS0RvSTYg'Yfv N'YOp t$ PSBR@b(uv5ё^\:NTI{ Ny,SN,1995:143-177. [3] #,Qeg,ݐc I{,-NVyf[B ,2001,31(5):462-467. [4] Dekleva T W, Forster D, Adv.Catal.,1986,34:81. [5] Polichnowski S W, J.Chem.Educ.,1986,63:204;Agreda V H,Chem.Technol.,1988:250. [6] Brodzki B D, Pannetier G, J.Mol.Catal.,1977,2:149. [7] Jones J H, Platinum Metals Rev.,2000,4(3):94-105. [8] Maitlis P M,Haynes A,Sunley G J,Howard M J, J.Chem.Soc.,Dalton Trans.,1996:2187. [9] Fulford A, Hickey C E, Maitlis P M, J.Organomet.Chem.,1990,398:311. [10] Haynes B E, Maitlis P M, et al., J.Am.Chem.Soc.,1993,115:4093. [11] Ellis P R, Pearson J M, et al., Organometallics,1994,13:3215. [12] Pearson J M, Maitlis P M, et al., J.Chem.Soc.,Chem.Commun.,1995:1045. [13] Paulik F E, Roth J F, J.Chem.Soc.,Chem.Commun.,1968:1578. [14] ѐOb _[l Ğ/Us^ I{ g:gSf[ 2003,23613-618. [15] 'Yzf, 0YNxSvQMuir 0,2005,58-11. [16] Smith B L, J.Mol.Catal.,1987,39:115-136. [17] Smith B L, Torrence G P, Aguilo A et al., US 5 026 908,1991. [18] 'Yzf, Ng\[, si`eg I{. CN 95 108 227.2,1995. [19] 'Yzf, Ng\[, si`eg I{. CN 95 104 298.X,1995. [20] 7]ZSN CN 94 103 447.X,1994. [21] ѐOb _[l Ğ/Us^ I{ 5ё^\ 2003,24(1)10-14. [22] Francis G M, Georgios R, et al.,0EP 752 406,1996; EP 749 948,1996. [23] Thiebaut D,Marchand D,Kalck Ph.,et al., US 20040044245 A1,2004. IJ "rtz|, 2 T p z " ( : < J L     FH  .0246:df :<>@XZ\^ԼOJQJ0J j`UH*5\5OJPJ\H*0J jU5CJ$OJPJ\aJ$ 0JOJQJOJQJCJ5CJOJQJ\aJ$GJ T F .(2Rv $$Ifa$O^npvx "(8>@BDF^dntvxz&(*,  (0t|&, flB jU jU5\5OJPJ\OJQJCJaJCJaJH*Tvxulll $$Ifa$$$IfF06    34ab DFVfvxwnnnwdnnnwlll $$Ifa$$$IfF06    34ab  * T ^ | j$$IfF xx06    34ab  $$Ifa$ BDVXZ\^` 68* . f h j l !!&!.!0!2!4!H!P!Z!b!d!f!!!!!!!!!!!!! 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