경막형용융결정화에의한파라디옥사논과디에틸렌글리콜혼합물로부터파라디옥사논의정제. Purification of p-dioxanone from p-dioxanone and Diethylene Glycol Mixture by a Layer Melt Crystallization
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1 Korean Chem. Eng. Res., Vol. 43, No. 5, October, 2005, pp 경막형용융결정화에의한파라디옥사논과디에틸렌글리콜혼합물로부터파라디옥사논의정제 m zk s * l o r l re o q 100 * re o 220 (2005 6o 15p r, o 6p }ˆ) Purification of p-dioxanone from p-dioxanone and Diethylene Glycol Mixture by a Layer Melt Crystallization Sung-Il Kim, Chul-Ung Kim and So-Jin Park * Chemical Process and Engineering Center, Korea Research Institute of Chemical Technology, 100, Jang-dong, Yuseong-gu, Daejeon , Korea *Department of Chemical Engineering, Chungnam National University, 220, Gung-dong, Yuseong-gu, Daejeon , Korea (Received 15 June 2005; accepted 6 September 2005) k Ž m l tn p lž p r o, Ž m lž p p k p r mp, s(seed)p pn np r e p m. llv 2 k p m, nrp Ž m p 0.08 l 246 Km., p p ρ l =k 1 +k 2 x+k 3 T+k 4 xt e q l lp, Ž ˆp k 1, k 2, k 3 k 4 p p 0.405, 1.361, 0.002, 0.004pl. np r e l r q (G) Ž m p v p ˆ lp, r q ep m p 1.5dl m., p r r ˆ o (K eff ) PDX v v p ˆ lp, o Wintermantel l p K eff = Z l. srp llv PDX r sq r l 99Í p p sr ppp k pl. h Abstract In order to purify diethylene glycol as main impurity included in p-dioxanone, SLE (solid-liquid equilibria) and mixture density on two components system of p-dioxanone and diethylene glycol were measured and a layered melt crystallization with seed has been applied. The SLE of p-dioxanone and diethylene glycol were a simple eutectic system and the temperature and PDX concentration at eutectic point were 0.08 and 246 K, respectively. Densities of their binary mixtures were well fitted by the best correlation equation, ρ l = x+0.002T 0.004xT. In the melt crystallization, the growth rate (G) was proportional to the 1.5th power of the subcooling degree. The effective distribution coefficient (K eff ) as the degree of impurity removal was observed to increase with increasing the growth rate and initial p-dioxanone concentration. And also, K eff was correlated with Z function using Wintermantel s model such as K eef = Z. Finally, PDX purity through the optimization of this process can be obtained over 99. Keywords: Layer Melt Crystallization, Purification, p-dioxanone, Diethylene Glycol, Growth Rate, Effective Distribution Coefficient, Wintermantel s Model 1. -Ž m p n, ~ l m k q p ov p vp v pl, p, d To whom correspondence should be addressed. cukim@krict.re.kr p,,,, p r q, n ˆp l n p [1]. l rp ep s p p n n r p l p lv p, p p nl o p lž (diethylene glycol, DEG)p o n qrp p [2, 3]. Fig. 1l DEGp 595
2 596 p ~o v Fig. 1. Synthetic route for the preparation of poly(p-dioxanone), PPDX via PDX from DEG. ˆ o pp Ž m (p-dioxanone, 1,4-dioxan-2- one, PDX)p rs rr ~, p rs ˆ l., DEGp ˆ o pp llv PDXp p p DEG l k, lž, lž k p l pp, 95Í r p llv. PDX p r p l vrrp m p p k rp, p r o k rr p k r. p rp r l p v m pr n pl p r p rn p. rq lrp d r p qrp pv, l p PDXm p nl ld s v p p ll kr v k d m v l rr e r k pp, pr l r l l v pp rl rp v p., q t n n q r p k r p, p p ˆrp p r l q n p rsl rn pv, r rp n p n l r p l n rp rp l p p n p rsl vr rn l p rrp p. p rl l n r n v k np ˆ l p rr p np r p l p [2-8]. v, p p p m l np ˆ p r p l rp l tn ~r t pp, sl tl p v p o}rp lr p, q v, sl l rœq m tp p rp p. p np r o np r m np r, rq qˆ p m p ˆp r l l p r p, q l 2t o ˆp p e r q p p p r p. p rp rqp o p qp l m p l rpv, r l oe p r p n [6-9]. l p PDX r p s m kl q r k r p l p k rv [2-5], rrl np p k vv k p. l l llv PDX n np r l p rr o l m. rp PDX q p p p p DEG r l, PDXm 2 l k (SLE, solid-liquid equlibria) o43 o k r mp, np r ee m. r e tn m e o K/min, r ( T) 5-40 K, PDX-DEG kp 96Í, 97Í, 98Ípl p, pl r q m rr l o p p l m h DEG Aldrich r p 99Í p p v p e k p rr lp n m., PDX DEG p ˆ o pl p e e (mini-plant)l vr r s mp, l Žl rr p r l p 99.99Í p p GC rr l n m [3]. Table 1 l PDX p o GC s p re m m PDX-DEG p -k PDX-DEGp 2 -k rp v l p ee m, e t l q (TA instruments DSC 2910, USA)l p l t v qˆp n okp rp v m r (static method)p rn m [10-13]. r l p pr s p e k 5mgp n l DSC q l q, v o l 10 K/minp dm m m e p m r p. p m o 50 o C-50 o C pl., okp SLE rp o Fig. 2m p r q n m. r n pyrex qvp t v qˆ(ò, triple vacuum jacket, : 50 mm, p: 120 mm) ˆ r rp o n qˆp v p l p ˆp, tp kp (magnetic stirrer bar)l p p m. m rn p l K-type p lr m (Ò) n l r m. SLE rp pr s p o t, 0.01 K/minp m l rp mr v r rp m kp s l m r p. rp p e l 3 mp, ±0.1 Kp m ol pl PDX-DEG p r PDX-DEG p rp rqe rq (Mettler Toledo, Density Measurement Package: No No ) n m. r, PDX-DEGp kp 96Í, 97Í 98Íp PDX t, ms n l m pr eˆ r m. r rp o, v n l (calibration) mp, r e m o ± gcm 3 pl. Table 1. GC conditions for PDX analysis Column 25 m 0.53 mm ID, BP UM (SGE) Carrier gas 6 cc-he/min Injector temperature 200 o C Detector, temperature FID, 250 o C Column temperature 60 o C-250 o C (10 K/min)
3 Fig. 2. Schematic diagram for apparatus of SLE measurement. 1. Circulator 5. Triple vacuum jacket 2. PID controller 6. Temperature probe 3. Magnetic stirrer 7. Thermometer 4. Magnetic bar 8. Personal computer np r e Fig. 3l r e p o np r q p ˆ l, pyrexqvp 2t o p r (Ò, =4 cm, p=18.5 cm)p. r p m m q (Ò, rpm, HTRC-20 )m r l p K-typep lr (Ò) m PID rl (Ò)l p ±0.1 Cp m o o rl m., ~ lž (ethylene glycol)p kp n m. e p r PDXl pr p DEG l o rs, r l tp, r p m PDXp p np r l p Ž m p rr 597 r(28) k p m p 30 Cl np ˆ o ov. pl l p rp eˆ o pr e ˆ, p v p v r qp o o 26 Cp m vrl o 0.1 gp PDX rp seed ~ l p p tep rp e. pl r p m e s l rr m v l r tv, r p qlkp m. v, r p l v p k l r p r p qlkp mr r m. pl r p rp r m e PDXp prp p m p, GC l p p m. 3. y 3-1. PDX-DEG h Fig. 4l PDX-DEGp 2 k ˆ l. p k ll rp (thermodynamic impurity)p s q v kp p (simple eutectic system) m, static DSC p r p p p p ˆ pl. nrp PDX (x) 0.08l 246 Kpl. v, PDXl p lž p ~ l p 1 qkr p prp p k pl. pr pnp l vrl m l r ee, p rp v s p p lvp p, np r rr ppp k pl. Fig. 5 PDX-DEG p PDX p m m l r, pr PDX-DEG p p(x)p 96, 97, 98Íl r m (T)l p ˆ l. e m m PDXp o C, 96-98Ím. p l k p p, p m Fig. 3. Schematic diagram for apparatus of a layer melt crystallization. 1. Circulator 6. Temperature probe in inlet of coolant 2. PID controller 7. Temperature probe in outlet of coolant 3. Layer crystallizer 8. Thermometer 4. Residue flask 9. Personal computer 5. Temperature probe in crystallizer Fig. 4. Solid-liquid phase diagram for PDX-DEG mixture. Korean Chem. Eng. Res., Vol. 43, No. 5, October, 2005
4 598 p ~o v Fig. 5. Density of PDX-DEG mixtures as a function of temperature and initial PDX concentration. v l rp, pr m l p v v p k p. p e m m l p mp p [10], e p el rn l Ž ˆp k 1, k 2, k 3 k 4p p 0.405, 1.361, 0.002, 0.004plp, t (relative standard deviation, RSD)m r (average absolute deviation, AAD) 4m pl. ρ l = k 1 + k 2 x+ k 3 T+ k 4 xt (1) l, T r m p, x l PDXp p. p nkp p k p e (5)p Z e r p qlkp nk p l rn l o m Fig. 6p 2 PDX-DEG p np r e l r e l r ˆ p. r p r l sp Œp p sp tep, m l n yp t p q m. r p er e p r l, e (2) n pr e s (PDX s, m, e )l rp (W) r ( r v p, PDX rp )p tp m [14]. X 2 s D o X s W = 0 π H ρ c l, X s r p, D o r p (4 cm), H r p(18.5 cm), ρ c rp (PDX r=1.39 g/cm 3 ), W rp p. Fig. 6l k p p, r e l r p o43 o k (2) Fig. 6. Variation of the thickness of crystalline layer with crystallization time in layered melt crystallization of PDX-DEG mixtures. l rp p p lv, l e p l p pr v p ˆ l. v, r e l r p Sq ˆ 5-11 mm ol q v pl. Fig. 6(a) pr PDXp p 97Íl m e l r p ˆ l, e l r p p p ˆ l., Fig. 6(b) pr p 0.1 K/minl p m r e l r p ˆ l, e l r p PDX s p
5 np r l p Ž m p rr 599 Fig. 8. Variation of crystalline growth rate against subcooling degree. p ˆ l (Fig. 7(a), 7(b)). p rp np r l r q l rp ps p ˆ [12], l l p p r q rl tn n ppp k pl. Fig. 8p r ( T)l r q (G)p - (log-log) ˆ ˆ f, G T v l rp v p ˆ l., Gm Tp ep e (3)p ˆ p [11, 12]. G = k G T g (3) Fig. 7. Variation of crystalline growth rate (G) with crystallization time in layered melt crystallization of PDX-DEG mixtures. p p k pl. p, p l r p l m p pp k pl. Fig. 7p e l r q (G)p ˆ p. l, r q Fig. 6p o e l o r q m. ~ G p r e l ˆ rp mp, e p r l vrl p ˆ l. p G p vrp pr p (97Í)l, p r (0.1 K/min)l p p kv l, k G r q p, g r q p, T=T * -T, Tm T * pp e l npk ˆp m p. e p r q p 1.5dl m, r q m/s p p lp pl l r l pp e (4)m p o (effective distribution coefficient, K eff ) ˆ p [15-16]. K eff = X ic X il l, X ic r p p v pp, X il p r qlnkp p v pp. v, K eff 1p nl rp p r v kp np, K eff 0p l rp p mr r np. p o ˆp p p k, evrp sql llv p. p r p p l l v rp (4) Korean Chem. Eng. Res., Vol. 43, No. 5, October, 2005
6 600 p ~o v Fig. 9. Variation of PDX purity with crystalline layer thickness. p k r p, Wintermantel[10, 17]p p p o e (5)m p K eff Zp ˆ l. v, Z kinetic m l p r l l p p ˆ (G, k d, C ρ im,l ) p pv ep. 1 K eff = fz ( ) (5) C im, l Z = ρ l C im, l G ρ c exp k d ρ l l, C im,lp npk p p, ρp nkp, ρ c rp, k d vr p. Fig. 10p np r l r p l o (K eff )p ˆ l. v Fig. 10(a) pr PDX s (97Í)l p ( K/min)l p, Fig. 10(b) pr (0.1 K/min)l PDX p (96, 97, 98Í)l p. k p, r l K eff p l pp p, Fig. 9p s l e e (2)m e (4)l rn l l lr. v, K eff pr s (, )l r e p, r l r np ˆ p rp r qlkp p e (4)l r n l m., rp er rp q l r l, rp llv kp tp e (2) rn l m. Fig. 10l k p m p, p r sql K eff 0.1 r p p l e q l rp 5-11 mm r p l p v, rp v K eff e p ˆ l., K eff p p rp p pr PDX (97Í)l v v p ˆ lp, pr (0.1 K/min)l v o43 o k Fig. 10. Variation of effective distribution coefficient with crystalline layer thickness. v p ˆ l. p po r sq e seedp Œpl p m r q r l m p. v, r q 5-11 mm p r l q, p n p p l., K eff PDX v v p ˆ l. Fig. 11p K eff l r q, vr, s ql p p m p o, Wintermantel rk e (5) rn l Zp e ˆ l. p Z K eff l m p tn l pp, np r p rp p ˆ l t, qlkp r e (1)l p p n m. p ep
7 np r l p Ž m p rr , 4m 0.002, 0.004pmp, t m r pl. (3) r p e l r p m r q p e p 1/2 mlp e l p rp, PDXp s p v r q m., r q PDXp 1.5p v p ˆ lp, G= T ˆ l. (4) r r ˆ o (K eff )p PDX v v p ˆ l., e Wintermantel l q rn lp, K eff = Z ˆ pl. srp, r q vr p p PDX plp PDX 99Í p p rr m. y Fig. 11. Plot of effective distribution coefficient versus Z. r q p nl r l p q l pp, vr r p rp kvp k p. l p e rn l e Fig. 11l k p p, p p tp, l lp Wintermantel l p k pl. K eff p Z p v l l ˆ ˆ pv, ~ e (6) p ˆ pl. p ep p r r rp sl m l eˆ ˆ, r q p n r l p q, vr r p p rp kvp k p., rp q nl r l p kp v, vr nl rp v(compact) kp r p p. rp p PDXp rrl n t n l p ppp k pl. K eff = Z 4. PDX-DEGp 2 l PDX rp p DEGp r o, k l ll r e p mp, np r l l p p v lp pl. (1) PDX-DEGp 2 k ll rp p sq v kp p m, nrp PDX (x)=0.08l 246 Km. (2) PDX-DEG p r ρ l = e q l lp, Ž ˆp k 1, k 2, k 3 (6) k 1 + k 2 x+ k 3 T+ k 4 xt k 4p p 0.405, 1. Yang, K. K., Wang, X. L. and Wang, Y. Z., Poly(p-Dioxanone) and its Copolymers, Journal of Macromolecular Science, C42(3), (2002). 2. Kim, C. U., Kim, K. J. and Cheon, Y. H., Separation of High Purity p-dioxanone from p-dioxanone Reaction Mixtures, Korean Patent No (2004). 3. Kim, C. U., Kim, S. I., Nam, S. Y., Ko, J. C., Seo, Y. J. and Choi, B. Y., Purification Method and Apparatus of High Purity p-dioxanone from Raw p-dioxanone, Korean Patent No (2005). 4. Ying, J. and Conn, N. H., Process for the Production of Dioxanone, U.S. Patent No. 5,391,707(1995). 5. Moyers, C. G., Charleston, W. V., Farr, M. P. and Somerville, N. J., Recovery of Dioxanone by Melt Crystallization, U.S. Patent No. 5,675,022(1997). 6. Riddick, J. A., Bunger, W. B. and Sakano, T. K., Techniques of Chemistry, Organic Solvents, 4 th ed, John Wiley and Sons, New York(1986). 7. Sloan, G. J. and McGhie, A. R., Techniques of Melt Crystallization, New York, John Wiley and Sons(1998). 8. Nicholas, P. W., Separate Organics by Melt Crystallization, Chem. Eng. Progress, 88(3), 52-60(1992). 9. Matsuoka, M., Fukuda, T., Takagi, Y. and Takiyama, H., Purification of Organic Solid Solutions by Melt Crystallization: Comparison Between Layer and Suspension Crystallization, J. of Crystal Growth, 166(1-4), (1996). 10. Cheon, Y. H., Kim, K. J., Kim, J. W. and Kim, S. H., Solid-Liquid Phase Equlibria of Binary and Ternary Mixtures for 2,6-Dimethylnaphthalene and 2,7-Dimethylnaphthalene with Ethanol or Methanol, J. of Chem. Eng. Data, 50(3), (2005). 11. Kim, K. J., Lee, J. M. and Ryu, S. K., Crystallization of Benzene from Benzene-Cyclohexane Mixtures by Layer Melt Crystallization-Phenomena of Impurity Inclusion in Crystal, J. of Korean Ind. & Eng. Chemistry, 8(3), (1997). 12. Kim, K. J., Kim, J. W., Kim, J. K. and Cheon, Y. H., Separation of Naphthalene from Solid Solution Mixture by Melt Crystallization, J. of Korean Ind. & Eng. Chemistry, 13(1), 63-68(2002). 13. Park, S. J. and Park, S. K., A Study on the Solid-Liquid Equi- Korean Chem. Eng. Res., Vol. 43, No. 5, October, 2005
8 602 p ~o v libria for Benzene+Aniline, Benzene+Nitrobenzene, p-xylene+ Cyclohexane, J. of Korean Ind. & Eng. Chemistry, 9(6), (1998). 14. Kim, K. J., Lee, J. M. and Ryu, S. K., Layer Growth Rate of Benzene Layer from Benzene-Cyclohexane Mixtures in Layer Crystallizer, J. of Korean Ind. & Eng. Chemistry, 7(2), (1996). 15. Sloan, G. J. and McGhie, A. R., Techniques of Melt Crystallization, New York, John Wiley and Sons(1998). 16. Ossipov, P., Continuous Fractional Crystallization on a Moving Cooled Belt, Int. J. Heat. Mass Transfer, 41(4-5), (1998). 17. Mersmann, A., Crystallization Technology of Handbook, Mercel Dekker(1994). o43 o k
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