Some of our Applications: CO 2 to chemicals via reversible CO 2 capture, biomass pretreatment, biomass fractionation etc
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1 Let the show begin
2 Some of our Applications: CO 2 to chemicals via reversible CO 2 capture, biomass pretreatment, biomass fractionation etc Professor Jyri-Pekka Mikkola Modified from knowyourmeme.com
3 Case PEA penta-amine Properties pka = 9.7 and 11 (in water) Superbase Soluble in water and organic solvents Colorless/yellowish viscous liquid with an odor of ammonia Melting point: -35 o C Boiling point: 380 o C Density: 0.95 g/ml Stability: Incompatible with strong oxidizing agents, acids, acid gases (e.g. CO 2 ) Price: 750 SEK/liter (Technical grade, Sigma Aldrich) Reversible CO 2 capture CO 2 capture and utilization in chemical synthesis Biomass pre-treatment As a solvent or catalysts in organic transformations...
4 Ongoing research with PEA in our Lab Synthesis of various commodities/solvents from PEA PEA Aqueous PEA solution (mix of PEA with water) on-aqueous PEA system (mix PEA with other solvent such as EtO, MeO ) Blended PEA system (PEA + other amine(s) + solvent).. Ionic liquids (ILs) With various acids (e.g. Cl, AcO etc.) Deep eutectic solvents (DESs) With various hydrogen bond donors such as ILs (ILs such as imidazolium, cholinium, pyridinium halides etc.).
5 Current success: Switchable aqueous PEA solvent system for reversible carbon dioxide capture Possible reactions of CO 2 with neat/aqueous PEA (amines) Carbamate synthesis (2 mol amine : 1 mol CO 2 ) 2 4 PEA 2 2 CO 2 PEA 2 4 Carbamic acid COO Carbamate COO - 3 (Bi)-carbonate (1 mol amine : 1 mol CO 2 ) 2 4 PEA 2 CO 2 RO/ 2 O R'OCOO (bi)-carbonate, R'= R or 2 O J. Kothandaraman et al., Green Chem., 2016, 18,
6 Current success: Switchable aqueous PEA solvent system for reversible carbon dioxide capture CO 2 absorption capacity neat or aqueous PEA solution Experimental eat PEA and aqueous PEA solutions with different PEA concentrations (Wt.%) 2 g PEA used in all experiments CO 2 flow rate = 30 ml/min Ambient conditions Observations CO 2 absorption rate as well as CO 2 capacity is dependent on amount of water in reaction mixture Optimum concentration = 56 wt. % PEA in WATER
7 Current success: Switchable aqueous PEA solvent system for reversible carbon dioxide capture Kamlet-Taft parameters: Correaltion with CO 2 absoprtion capacity of PEA system Kamlet-Taft parameters (polarity of the solvent) ydrogen-bond donor acidity parameter (α) represents ability of the solvent to donate a proton to the solute to establish solventsolute hydrogen-bond interaction ydrogen-bond acceptor basicity parameter (β) Di-polarity/polarizability parameter (π*) represents the ability of the solvent to induce a dipole in the probe molecule Parameters measured with solvatochromic dyes or probe molecules such as Reichardt s dye,,-diethyl-4-nitroaniline and 4-nitroaniline Observations Kamlet-Taft parameters were dependent on both amount of PEA and water in the solution CO 2 absorption capacity gradually increased with increase in polarity of solvent, however with diluted systems or after optimum PEA concentration (here < 56wt. %) it did not show the proportional trend with polarity of the solution
8 Current success: Switchable aqueous PEA solvent system for reversible carbon dioxide capture 13 C MR analysis of reaction mixture after CO 2 bubbling Chemical shift for Carbamate = ppm, Chemical shift for (bi)-carbonate = ppm
9 Current success: Switchable aqueous PEA solvent system for reversible carbon dioxide capture Thermally induced regeneration of PEA Experimental CO 2 saturated 56 wt. % PEA solution heated at 100 and 120 o C for 1 and 3h Observed changes controlled by 13 C MR analysis Observations It is possible to regenerate PEA from PEA carbamate and (bi)-carbonate PEA carbamate was found more thermally stable than its (bi)-carbonate analogue Independent on amount of water in the solution, it is possible to regenerate PEA from PEA carbamate and (bi)-carbonate under thermal treatment
10 Correlation of polarity parameters with CO 2 capture in deep-eutectic solvents (DESs) ydrogen bond acceptor ydrogen bond donor R 1-Alkylimidazolium chloride 1 Cl - O n 3 Cl - Alkanolammonium chloride 2 2 Alkylenediamine 1', 2', 3', 5' n = 1, 2, 3, 5 * n Scheme of DES synthesis R 2 R= 1, 2, 3, 4 -Cl protonation/ quaternization Cl K R Protic ionic liquid complexation 2 BD n * R Cl - * n Deep-eutectic solvent (DES)
11 CO 2 absorption kinetics and polarity parameters of DESs Solvatochromic method π* α β DESs wt % CO 2 Mole CO 2 / E T 30 / mole DESs kcal.mol -1 [11 ] (1:1) [11 ] (1:2) [11 ] (1:3) [11 ] (1:4) O Reichardt's dye O 2 4-nitroaniline (A) O 2,-diethyl-4-nitroaniline (DEA) [12 ] (1:4) [13 ] (1:4) Empirical polarity equations 1. Electronic transition Energy E T 30 (kcal.mol -1 ) = 28591/λ max 2. Dipolarity/polarizability ν max(dea) = π* 3. ydrogen bond acidity α = E T π* ydrogen bond basicity ν max(a) = 1.035ν max(dea) 2.8β [14 ] (1:4) [21 ] (1:4) [22 ] (1:4) [23 ] (1:4) [24 ] (1:4)
12 Polarity parameters and biomass dissolution Biomass dissolution in a medium depends on untangling of -bond network and is facilitated by the basicity of the solvent. Ionic liquids having hydrogen bond donor basicity (β) > 0.8 are efficient in wood pretreatment & dissolution processes. Alkanolammonium chloride-based DESs can be promising candidates in biomass dissolution because of their high β value. Brandt, A. et al. Green Chem., 2010, 12,
13 A Short Commercial Brake...! Scientific Reports & ature Communications also biological applications
14 Another Short Commercial Brake...!
15 See the talk by the director of the Royal Swedish Academy of Engineering Sciences (IVA), Björn O. ilsson (screen capture below) Thai Bui Quoc (PhD student) Dr. Santosh Khokarale Dr. Shashi Kant Shukla
16 Tack Thank You ope to see U in Future too! Chemical Engineering Research thinglink.com
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