Removal of anionic azo dyes from aqueous solution by functional ionic liquid cross-linked polymer

Removal of anionic azo dyes from aqueous solution by functional ionic liquid cross-linked polymer
Removal of anionic azo dyes from aqueous solution by functional ionic liquid cross-linked polymer

Journal of Hazardous Materials 261 (2013) 83–90

Contents lists available at ScienceDirect

Journal of Hazardous

Materials

j o u r n a l h o m e p a g e :w w w.e l s e v i e r.c o m /l o c a t e /j h a z m a

t

Removal of anionic azo dyes from aqueous solution by functional ionic liquid cross-linked polymer

Hejun Gao a ,b ,Taotao Kan c ,Siyuan Zhao d ,Yixia Qian d ,Xiyuan Cheng d ,Wenli Wu d ,Xiaodong Wang e ,Liqiang Zheng a ,?

a

Key Laboratory of Colloid and Interface Chemistry,Shandong University,Ministry of Education,Jinan 250100,China

b

Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province,China West Normal University,Nanchong 637000,China c

CNOOC Energy Technology and Services-oil?eld Technology Services Co.,Tanggu,Tianjin 300452,China d

School of Chemistry and Chemical Engineering,Shandong University,Jinan 250100,China e

Shandong Provincial Analysis and Test Center,Jinan 250100,China

h i g h l i g h t s

?Equilibrium,kinetic and thermodynamic of adsorption of dyes onto PDVB-IL was investigated.?PDVB-IL has a high adsorption capacity to treat dyes solution.

?Higher adsorption capacity is due to the functional groups of PDVB-IL.?

Molecular structure of dyes in?uences the adsorption capacity.

a r t i c l e

i n f o

Article history:

Received 23March 2013

Received in revised form 1July 2013Accepted 2July 2013

Available online 10 July 2013

Keywords:Azo dye Adsorption Ionic liquid Polymers

a b s t r a c t

A novel functional ionic liquid based cross-linked polymer (PDVB-IL)was synthesized from 1-aminoethyl-3-vinylimidazolium chloride and divinylbenzene for use as an adsorbent.The physicochemical properties of PDVB-IL were investigated by Fourier transform infrared spectroscopy,scanning electron microscopy and thermogravimetric analysis.The adsorptive capacity was investigated using anionic azo dyes of orange II,sunset yellow FCF,and amaranth as adsorbates.The maximum adsorption capacity could reach 925.09,734.62,and 547.17mg/g for orange II,sunset yellow FCF and amaranth at 25?C,respectively,which are much better than most of the other adsorbents reported earlier.The effect of pH value was investigated in the range of 1–8.The result shows that a low pH value is found to favor the adsorption of those anionic azo dyes.The adsorption kinetics and isotherms are well ?tted by a pseudo second-order model and Langmuir model,respectively.The adsorption process is found to be dominated by physisorption.The introduction of functional ionic liquid moieties into cross-linked poly(divinylbenzene)polymer constitutes a new and ef?cient kind of adsorbent.

? 2013 Elsevier B.V. All rights reserved.

1.Introduction

As the largest and most versatile class of organic dyestuffs,azo dyes are widely used in textile,paper,and leather industry [1].With the development of the industries above,a huge amount of wastewater containing azo dyes is discharged to the environment above the level that the nature can eliminate.The azo dyes and their breakdown products can cause toxic effects in the aquatic environment and are mutagenic and carcinogenic to humans [2–4].The treatment of dye wastewater becomes more important than ever for the environment.Many technologies were applied to

?Corresponding author.Tel.:+8653188366062;fax:+8653188564750.E-mail address:lqzheng@https://www.360docs.net/doc/4315972247.html, (L.Zheng).

treat dye wastewater,such as biological treatment [5],coagula-tion/?occulation [6],chemical oxidation [7],membrane ?ltration [8],ion-exchange [9],photocatalytic degradation [10],and adsorp-tion [11].Among those technologies,the most common one is the adsorption technology due to its effectiveness,ef?ciency,economy and no secondary pollution.

Ionic liquids (ILs)are receiving much attention owing to their unique properties,such as high thermal stability and high ionic conductivity [12].Currently,many functionalized ILs have been used to protect water resource.Fuerhacker et al.[13]reported that the degree of removal of heavy metals (Cu,Ni and Zn)can reach 90%using quaternary ammonium and phosphonium ILs.Gharehbaghi and Shemirani [14]prepared an ionic liquid (1-hexyl-3-methylimmidazolium bis(tri?uormethylsulfonyl)imid).When it was injected into the Congo Red wastewater,most of the

0304-3894/$–see front matter ? 2013 Elsevier B.V. All rights reserved.https://www.360docs.net/doc/4315972247.html,/10.1016/j.jhazmat.2013.07.001

84H.Gao et al./Journal of Hazardous Materials261 (2013) 83–90

dye molecules were extracted into?ne IL droplets and removed from aqueous phase.Poursaberi and Hassanisadi[15]synthesized IL@Fe3O4nanoparticles from IL-COOH and Fe3O4and found it to be an effective adsorbent of Reactive Black5(maximum adsorption capacity161.29mg/g).

The preparation of an effective adsorbent for removing anionic azo dyes from aqueous solution is expected to meet the demand of environmental protection.It is well known that the amine-functional groups on the surface of an adsorbent can greatly improve adsorption capacity[16,17].The adsorbent with multi-ple benzene rings can bring – stacking interaction between azo dye and the adsorbent,which further improves the adsorption capacity[18].The ILs with amine groups on cross-linked polymer containing multiple benzene rings may obtain a new kind of ef?-cient adsorbent.In this work,a cross-linked polymer is obtained by copolymerizing divinybenzene and imidazolium ILs with an amine group.The structure of the cross-linked polymer was characterized and the physicochemical properties were investigated in detail.The adsorption capacity of functional ionic liquid cross-linked polymer was investigated in anionic azo dyes solutions.

2.Experimental

2.1.Materials

Orange II(85%),sunset yellow FCF(95%),and amaranth (98%)were obtained from Aladdin Chemical Reagent Co.,Ltd. Those dye molecular structures are shown in Table1.1-Vinylimidazole(99%),2,2 -azobis(2-methylpropionitrile)(99%), dimethylformamide(99%)and2-chloroethylamine hydrochloride (99%)were purchased from Beijing Chemical Reagent Co.Divinyl-benzene(DVB)(80%)was provided by Aldrich.

2.2.Methods

2.2.1.Preparation of cross-linked polymer[19]

1-Vinylimidazole(0.1mol)and2-chloroethylamine hydrochlo-ride(0.1mol)were added into50ml acetonitrile.The mixture was stirred and re?uxed under a nitrogen atmosphere for48h.The resulting solid was washed several times with anhydrous ethanol. The solid with equimolar NaOH were dissolved in water and stirred at room temperature for24h.After evaporating,the crude product was extracted by methanol.Then,the product was dried for48h under vacuum and the functional ionic liquid was obtained.

DVB(0.02mol),1-aminoethyl-3-vinylimidazolium chloride (0.005mol)and an appropriate amount of2,2 -azobis(2-methylpropionitrile)were dissolved in50ml dimethylformamide under nitrogen.The mixture was stirred at80?C for24h,and a yellow solid was collected by?ltration and washed with acetone.The adsorbent of poly(divinylbenzene-co-1-aminoethyl-3-vinylimidazolium chloride)was obtained.

The synthetic process of PDVB-IL is shown in Fig.1.

2.2.2.Characterization of the adsorbent

The Fourier transform infrared(FT-IR)spectra of PDVB-IL,PDVB-IL-Orange II(after adsorption of orange II on PDVB-IL)and orange II were obtained on VERTEX-70FT-IR spectrometer using KBr pellet in the range of4000–400cm?1.The particle size and morphology of PDVB-IL were characterized using a scanning electron microscope (SEM,JSM-7600F,EOL,Ltd.,Japan).The N2adsorption–desorption isotherm for sample was measured at77k with a Quadrasorb Station2Analyzer(Quantachrome,USA).Thermogravimetric anal-ysis(TGA)was carried out using a Rheometric Scienti?c TGA1500 (Piscataway,NJ)to investigate the thermal properties of samples. Studies were conducted under inert atmosphere of nitrogen using Table1

Characteristics and structures of anionic azo dyes.

Generic name M.W. max(nm)Molecular structure

Orange II350.32484

Sunset yellow FCF452.38482

Amaranth604.47521

8–10mg samples at a heating rate of10?C/min in the range of ambient temperature to800?C.

2.2.

3.Batch adsorption procedure

Batch adsorption was carried out in order to evaluate the adsorption capacity.The three dye solutions were prepared by dilu-tion of the stock standard solution(dye solution200mg/L).All batch adsorption experiments were carried out as follows:20mL dye solutions and2mg PDVB-IL were poured into100mL conical beaker.The conical beaker was shaken by the oscillator(SHZ-82, Changzhou Shaipu Experimental Instrument Factory,China)at a speed of150rpm.After centrifugation,the solution absorbance was measured using UV–vis–NIR spectroscopy(Hitachi U-4100,Japan) with the max at484,482and520nm for orange II,sunset yel-low FCF and amaranth,respectively.The amount of adsorbed dye on PDVB-IL(q,mg/g)was calculated according to the following equation:

q=

C0?C f

m

V(1)

where C0is the initial concentration of dyes in solution(mg/L),C f is the dyes concentration at equilibrium(mg/L),m is the mass of adsorbent(g),and V is the volume of solution(L).

H.Gao et al./Journal of Hazardous Materials261 (2013) 83–90

85

Fig.1.Synthetic route of

PDVB-IL.

Fig.2.FT-IR spectra of PDVB-IL,PDVB-IL-Orange II(i.e.after adsorption of Cr(VI) onto PDVB-IL)and orange II.

2.2.4.Models for adsorption kinetics,isotherm and thermodynamics

To investigate the amount of anionic azo dyes adsorbed on the surface of the PDVB-IL at any time and the amount adsorbed at equi-librium,the pseudo-?rst-order and pseudo-second-order models were adopted to elucidate the adsorption kinetic process,which could be expressed as Eqs.(2)and(3),respectively,

log(q e?q t)=log q e?k1t(2)

t q t =1

k2q2e

+

t

q e(3)

where k1(/h)and k2(mg/g h)are the rate constant of the pseudo ?rst-order and the pseudo-second-order kinetics,respectively.q t (mg/g)and q e(mg/g)represent the adsorption capacity at any time t(h)and at equilibrium,respectively.t(h)is the contact time.

The dyes adsorption isotherm data were correlated with the theoretical models of Langmuir and Freundlich.

The Langmuir isotherm model is obtained by

C e q e =1

q m K L

+

C e

q m(4)

where C e is the equilibrium liquid concentration(mg/L),q e is

the amount adsorbed on solid at equilibrium(mg/g),q m is the

maximum theoretical adsorption capacity(mg/g),and K L is the

adsorption equilibrium constant(L/mg).The constants q m and K L

can be calculated from the intercepts and the slopes of a linear plots

of C e/q e versus C e.

The Freundlich isotherm is the most important multilayer

adsorption isotherm for rough surfaces.The linear form of the

Freundlich isotherm model can be represented as

log q e=

1

n log C e

+log K F(5)

where K F and1/n are characteristic constants representing the

adsorption capacity and adsorption intensity of the system,respec-

tively.The values of K F and1/n are obtained from linear plots of

log q e versus log C e.

For the Langmuir-type adsorption process,the essential char-

acteristics can be explained by dimensionless constant separation

factor(R L),which is considered as a more reliable indicator of the

adsorption capacity.The value of R L can be obtained by the follow-

ing equation:

R L=1

1+K L0

(6)

The effect of temperature on the adsorption of anionic azo dyes

was studied in order to obtain the relevant thermodynamic param-

eters.The standard free energy change( G?)for adsorption can be

calculated from the following equation:

G?=?2.303RT log K e(7)

where R is the universal gas constant(8.314J/mol K)and T is the

absolute temperature(K).

The thermodynamic parameters of standard enthalpy change

( H?)and entropy change( S?)for the process can be determined

from the following equations:

log K e=

S?

2.303R

?

H?

2.303RT

(8)

K e=

q e

C e(9)

The values of H?and S?can be calculated from the slope and

the intercept,respectively,of a linear plot of log K e against1/T.

86H.Gao et al./Journal of Hazardous Materials261 (2013) 83–

90

Fig.3.The interaction between dye molecules and PDVB-IL.

The activation energy(E a)and sticking probability(S*)for the adsorption of anionic azo dyes onto the surface of the PDVB-IL are calculated by

S?=(1??)e?(E a/RT)(10) The sticking probability(S*)is a function of the adsor-bate/adsorbent system under investigation but must lie in the range 0

?=1?C e

C0(11)

3.Results and discussion

3.1.Characterization of PDVB-IL

The FTIR spectra of PDVB-IL,PDVB-IL-Orange II(i.e.after adsorp-tion of Cr(VI)onto PDVB-IL),and orange II are shown in Fig.2.In the spectrum of PDVB-IL,the peak at3440cm?1is attributed to the stretching mode of the N H groups.The bands at2926and 2867cm?1are assigned to the C H stretching vibrations[20].The bands at1630and1603cm?1are due to C C stretching vibrations of imidazole ring and N H inplane bending vibrations,respectively [21].A strong band at1448cm?1is assigned to C C stretching of the benzenoid rings[22].The peak at1162cm?1is C N stretching vibrations.In addition,the spectrum shows the presence of aro-matic(900–600cm?1)groups[23].The above results indicate that the cross-linked polymer containing the functional groups of amine and benzene ring was successfully prepared.The peak at3441cm?1 (PDVB-IL)is shifted to3454cm?1in the spectrum of PDVB-IL-Orange II,which can be due to the hydrogen bonding interactions between PDVB-IL and orange https://www.360docs.net/doc/4315972247.html,parison of the FT-IR spectra of orange II and PDVB-IL-Orange II could reveal that absorption peaks of PDVB-IL-Orange II in the bands of4000–3000,1700–1400,and 900–600cm?1shifted to longer wavelengths,indicating that – interactions exist.The bands at1035–1204cm?1of–SO3?(Orange II)and1162cm?1of C N(PDVB-IL)are reduced after adsorption of orange II onto PDVB-IL,which re?ects the effect of electrostatic interaction on the binding of orange II.The interaction between orange II and PDVB-IL is shown in Fig.3.

SEM images of the surface of PDVB-IL are depicted in Fig.4.The surface of PDVB-IL is rough.The speci?c surface area BET value is 655.051m2/g(Fig.5A)and the pore diameter of PDVB-IL is2.583nm (Fig.5B).The large,rough and porous surface provides a good adsorption site for dyes to be trapped and adsorbed.

The thermal stability of prepared PDVB-IL was characterized by thermogravimetric analysis.TGA plots of PDVB-IL is shown in Fig.6.The PDVB-IL shows three weight losses,which appears at ~300–410?C,~410–500?C and above500?C.The weight loss of PDVB-IL at~300–410?C is due to the part of ILs on the polymer [24].The main weight loss occurring between430and500?C is attributed to degradation of PDVB[19].The amount of ILs in the PDVB-IL is about6.9wt%.The weight loss of PDVB-IL is negligible below300?C,indicating that the PDVB-IL can be applied to treat high temperature wastewater.

3.2.Effect of pH on adsorption

The pH of initial solution has signi?cant effect on the adsorption process,since it determines the surface charge of the adsorbent and the degree of ionization and speciation of the adsorbates[16,25]. The functional group of amine(–NH2)on PDVB-IL can be proton-ated to ammonium cation with decreasing pH value of solution [26].The adsorption capacities of dyes on PDVB-IL are plotted as a function of pH value in Fig.7.The results show that the adsorption capacity of anionic azo dyes gradually increases with decreasing pH from8to1.This may be due to the increase of strong electrostatic attractions induced by ammonium cationic group with decreasing pH,which leads to the increase of adsorption capacity[27,28].The number of negative charge per dye molecule(orange II,

sunset Fig.4.SEM images of PDVB-IL.

H.Gao et al./Journal of Hazardous Materials 261 (2013) 83–90

87

Fig.5.(A)N 2sorption isotherms and (B)pore size distributions for

PDVB-IL.

Fig.6.TGA of PDVB-IL under nitrogen.

yellow FCF,and amaranth)is different.One SO 3?(orange II)needs one cationic site,while one molecule of sunset yellow FCF and ama-ranth need two and three cationic sites,respectively.Therefore,the capacity of different dyes adsorption is different at the same pH value.The following experiments were carried out at natural pH

(5.6).

Fig.7.In?uence of pH on the adsorption capacity of PDVB-IL toward anionic azo dyes.(C 0=120mg/L,T =25?C,contact time =6

h).

Fig.8.Adsorbed amount of anionic azo dyes by PDVB-IL as a function of contact time.(C 0=100mg/L,T =25?C).

3.3.Adsorption kinetics

The adsorption kinetics of orange II,sunset yellow FCF and ama-ranth on PDVB-IL were studied to investigate the adsorption rate at which contaminates were removed from aqueous solutions.Fig.8shows the effect of contact time on the amount of adsorbed anionic azo dyes at 25?C.

Fig.8showed that the three anionic azo dyes were adsorbed rapidly at the initial 1h.After 5h,the adsorption capacity did not change with the contact time,indicating the adsorption equilib-rium was approached.The adsorption capacity of anionic azo dyes on PDVB-IL at equilibrium are 868.41,760.52,and 490.51mg/g for orange II,sunset yellow FCF and amaranth at 25?C,respectively.The pseudo-?rst-order and pseudo-second-order kinetic parameters are given in Table 2.The coef?cient of determination (R 2)values of pseudo ?rst-order kinetic curve can reach up to 0.97.However,the experimental q e values do not agree with that calculated ones (Table 2),indicating that the adsorption of anionic azo dyes onto PDVB-IL adsorbent does not conform to the pseudo-?rst-order model.The R 2values of pseudo second-order kinetic curve are greater than 0.99.Moreover,the values of calculated q e are closer to the experimental q e values for pseudo-second order kinetics,indicating that the adsorption kinetics is well ?tted by a pseudo second-order model [29].Ranking of these anionic azo dyes in terms of k 2order:

Orange II >Sunset yellow FCF >Amaranth

88H.Gao et al./Journal of Hazardous Materials261 (2013) 83–90

Table2

Pseudo-?rst-order and pseudo-second-order kinetic parameters for adsorption rate of anionic azo dyes on PDVB-IL.

Component Pseudo-?rst-order Pseudo-second-order Experimental qe qe(mg/g)K1×10?1(/h)R2qe(mg/g)K2×10?3(mg/g h)R2

Orange II251.49±18.14 2.00±0.170.9649892.91±7.12 4.83±0.750.9991868.41±23.04 Sunset yellow FCF321.73±20.60 2.05±0.150.9736800.10±8.76 3.21±0.410.9984760.25±41.32 Amaranth433.58±43.56 2.85±0.240.9663558.79±8.47 1.95±0.150.9969490.51±28.32

Table3

Langmuir and Freundlich constants for the adsorption of orange II,sunset yellow FCF(SY)and amaranth on PDVB-IL.

Component T(?C)Langmuir constants Freundlich constants

q m(mg/g)K L(L/mg)R2R L K F(mg/g)n R2

Orange II 10840.68±17.230.59±0.230.99740.011–0.043526.86±23.568.88±1.280.9149 25943.45±7.10 1.29±0.310.99970.005–0.017614.89±8.817.78±0.390.9889 40970.91±6.41 1.69±0.440.99970.004–0.013652.38±10.048.06±0.480.9846

SY 10724.65±3.21 1.25±0.280.99980.005–0.017547.09±6.3314.14±0.790.9861 25746.35±7.82 1.72±1.040.99950.004–0.022631.57±10.7729.42±4.900.8888 40787.45±5.91 2.89±1.860.99970.003–0.013688.19±10.3134.27±4.860.9168

Amaranth 10523.61±5.160.23±0.030.99940.027–0.077302.32±9.558.57±0.630.9764 25610.29±17.990.11±0.020.99480.056–0.143249.29±22.94 5.54±0.770.9196 40690.50±24.180.10±0.020.99270.061–0.156237.37±22.93 4.53±0.560.9363

Table4

Comparison of PDVB-IL adsorption capacity among different adsorbents.

Anionic azo dyes Adsorbents Adsorption capacities(mg/g)References

Orange II Bottom ash12.50[30]

Sludge adsorbent350[31] Activated carbon404[32]

PDVB-IL1000Present work

Sunset yellow FCF Mangrove barks12.72[33]

LDH-MAN4142.86[34]

CaAl-LDH-NO3398.41[27]

PDVB-IL769.23Present work

Amaranth Alumina reinforced polystyrene16.86[29] Citrullus lanatus rind23.0[35]

Fe3O4/ZrO2/chitosan99.6[36]

PDVB-IL666.67Present work

In the dyes solution,the anionic dye molecules are trapped by PDVB-IL.The electrostatic repulsion could be formed by the nega-tive charges of dye molecules on the surface of adsorbent,which may decrease the speed of adsorption.One amaranth molecule has three negative charges.The k2value of amaranth should be the smallest one.In other words,the k2value of orange II is the biggest one,because it is only one negative charge per molecule.

3.4.Adsorption isotherms

Adsorption process is usually studied through adsorption isotherm.The adsorption isotherm describes the equilibrium rela-tionship between the adsorbate,adsorbent,and the equilibrium concentration of adsorbate in solution.Two well-known adsorp-tion isotherms,Langmuir and Freundlich models,are applied to describe the adsorption isotherms.These isotherms relate the equi-librium adsorption capacity to the equilibrium concentration in the solution(Fig.9).

The Langmuir and Freundlich constants can be obtained by linear regression analysis.Table3presents the results and the coef?cient of determination(R2).It can be seen that the R2val-ues of Langmuir isotherm are greater than those for Freundlich isotherm,indicating that Langmuir model is better?tted the experimental data than Freundlich model at investigated tem-peratures.The results suggest the monolayer coverage of dye on the surface of PDVB-IL.The q m can reach925.09,734.62,and 547.17mg/g for orange II,sunset yellow FCF and amaranth at25?C,respectively.Adsorption capacities of different adsorbents toward the three anionic azo dyes are compared with PDVB-IL in Table4. It is obvious that the adsorption capacity of PDVB-IL is much higher than most of the other adsorbents reported earlier.The large adsorption capacity could belong to the strong adsorption af?nity of PDVB-IL toward the three anionic azo dyes,which is caused by the high speci?c surface area coupled with unusual surface morpholo-gies,as well as – stacking,hydrogen-bonding and electrostatic interaction between dye and functional group of PDVB-IL[37,38]

. Fig.9.Adsorption isotherms for anionic azo dyes at25?C.(contact time=6h).

H.Gao et al./Journal of Hazardous Materials261 (2013) 83–9089 Table5

Thermodynamic parameters for adsorption of anionic azo dyes on PDVB-IL.

Compound Temperature(K) G?(kJ/mol) H?(kJ/mol) S?(kJ/mol K)E a(kJ/mol)S*

Orange II 283?7.197±0.05414.537±3.4500.077±0.01210.742±2.4220.479±0.401 298?8.712±0.050

313?9.488±0.051

Sunset yellow FCF 283?6.314±0.111 5.720±1.1190.042±0.004 3.556±0.7280.011±0.003 298?6.835±0.114

313?7.595±0.113

Amaranth 283?4.589±0.1109.106±0.4660.048±0.002 4.137±0.3120.010±0.001 298?5.266±0.105

313?6.043±0.099

The different maximum adsorption capacities are attributed to the molecular structures of anionic azo dye molecules.When the dye molecules were adsorbed onto PDVB-IL,the negative charges of dye molecules induced electrostatic repulsion on the surface of PDVB-IL.With increasing negative charge of dye molecules(Table1),the electrostatic repulsion became strong and many positive charges on the surface of PDVB-IL were consumed.As a result,the adsorption capacity decreased sharply with the increasing of negative charges per molecule.

The value of R L can show that the adsorption dye on PDVB-IL is unfavorable(R L>1),linear(R L=1),favorable(0

3.5.Thermodynamics of adsorption

Table5presents the resulting G?, H?,and S?values for adsorption of anionic azo dyes on PDVB-IL.A negative change in adsorption standard free energy( G?)indicates that the adsorp-tion behavior is a spontaneous process[40].With an increase in temperature,the absolute value of G?gradually increases,imply-ing that the adsorption process is more spontaneous at higher temperature.The positive values of H?con?rms the endothermic nature of the adsorption process,and the positive values of S?imply that the adsorbed anionic azo dyes present a certain amount of freedom in the solid/solution interface[41].This phenomenon is due to the physisorption,which takes place through electrostatic interactions.This interaction is attributed to the amine functional groups on the surface of PDVB-IL.

In order to further con?rm that the physisorption is the predom-inant mechanism,the E a and S*are calculated from the slopes and the intercepts of a linear plots of ln(1??)versus1/T,and are shown in Table5.The value of E a is small,indicating that the physisorption is the dominating role in the adsorption process[42].

4.Conclusions

The functional ionic liquid cross-linked polymer,PDVB-IL, was successfully prepared by polymerization of1-aminoethyl-3-vinylimidazolium chloride and divinylbenzene.The adsorptive capacity of PDVB-IL was measured in three kinds of anionic azo dyes solutions(orange II,sunset yellow FCF,and amaranth).With the increase of pH,the adsorption capacity gradually decreases. The maximum values of orange II,sunset yellow FCF,and ama-ranth are925.09,734.62,and547.17mg/g at25?C,respectively. The adsorption thermodynamics show that physisorption plays the dominating role in the adsorption process.It is hoped that this work may provide a novel kinds of adsorbent with important practical applications.Acknowledgments

The authors are grateful to the National Basic Research Pro-gram(2009CB930101),the National Natural Science Foundation of China(No.91127017),Specialized Research Fund for the Doc-toral Program of Higher Education of China(No.20120131130003) and the Shandong Provincial Natural Science Foundation,China (ZR2012BZ001).

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The way常见用法

The way 的用法 Ⅰ常见用法: 1)the way+ that 2)the way + in which(最为正式的用法) 3)the way + 省略(最为自然的用法) 举例:I like the way in which he talks. I like the way that he talks. I like the way he talks. Ⅱ习惯用法: 在当代美国英语中,the way用作为副词的对格,“the way+ 从句”实际上相当于一个状语从句来修饰整个句子。 1)The way =as I am talking to you just the way I’d talk to my own child. He did not do it the way his friends did. Most fruits are naturally sweet and we can eat them just the way they are—all we have to do is to clean and peel them. 2)The way= according to the way/ judging from the way The way you answer the question, you are an excellent student. The way most people look at you, you’d think trash man is a monster. 3)The way =how/ how much No one can imagine the way he missed her. 4)The way =because

里根柏林墙英文演讲稿

篇一:追忆柏林墙 追忆柏林墙 肯尼迪在柏林墙边的演说: kennedy 二千年以前,最自豪的夸耀是civitas romanus sum,今天,自由世界最自豪的夸耀是ich bin ein berliner。 世界上有许多人确实不懂,或者说他们不明白什么是自由世界和共产主义世界的根本分歧。让他们来柏林吧。有些人说,共产主义是未来的潮流。让他们来柏林吧。有些人说,我们能在欧洲或其他地方与共产党人合作。让他们来柏林吧。甚至有那么几个人说,共产主义确是一种邪恶的制度,但它可以使我们取得经济发展。“lasst sie nach berlin kommen.” 自由有许多困难,民主亦非完美,然而我们从未建造一堵墙把我们的人民关在里面,不准他们离开我们。我愿意我的同胞们——他们与你们远隔千里住在大西洋彼岸——说,他们为能在远方与你们共有过去十八年的经历感到莫大的骄傲。我不知道还有哪一个城镇或都市被围困十八年仍葆有西柏林的这种生机、力量、希望和决心。全世界都看到,柏林墙最生动最明显地表现出一种失败。但我们对此并不感到称心如意,因为柏林墙既是对历史也是对人性的冒犯,它拆散家庭,造成妻离子散骨肉分离,把希冀统一的一个民族分成两半。 这个城市的事实也用于整个德国——只要四个德国人中有一个被剥夺了自由人的基本权利,即自由选择的权利,那么欧洲真正持久的和平便绝无可能实现。经过保持和平与善意的十八年,这一代德国人终于赢得自由的权利,包括在持久和平中善所有的人民,实现家庭团聚和民族统一的权利。你们住在受到保护的一座自由之岛上,但你们的生活是大海的一部分。因此让我在结束讲话时请求你们抬起目光,超越今日的危险看到明天的希望;超越这道墙看到正义的生平来临的一天;超越你们自己和我们自己看到全人类。自由是不可分割的,只要一人被奴役,所有的人都不自由。当所有的人都自由了,那时我们便能期待这一天的到来:在和平与希望的光辉中这座城市获得统一,这个国家获得统一,欧洲大陆获得统一。当这一天最终来临——它必将来临——时,西柏林人民将能对这一点感到欣慰:几乎二十年时间里他们站在第一线。 一切自由人,不论他们住在何方,皆是柏林市民,所以作为一个自由人,我为“ich bin ein berliner”这句话感到自豪。 历史见证:越过柏林墙,寻求自由 柏林墙由12公里长的水泥墙和137公里长的铁丝网组成,包括有116个观望台,随后经过了四次改建和加固。柏林墙一共截断了192条街道(97条在柏林内,95条为柏林通向东德的道路),32条铁路线,8条轻轨和4条地铁以及3条高速公路。边界上的河流、湖泊也被禁止通航,并加以监视。西柏林变成了一座孤岛。谁想在西柏林与西德之间旅行,则必须通过边境的严格检查。 第二次世界大战结束后,德国被分为4个区域,分别由法国、英国、美国和苏联接管,后来前三方合并,而苏联接管的地区变得更加孤立。这条1953年拉起的钢丝围栏把很多德国朋友分开了。 随着苏联和西方国家紧张局势的加剧,不同地区间的通道逐渐缩小。1961年,这条边界被正式化地变成了一堵砖墙,照片中东德士兵和工人正在给柏林墙增加高度。柏林墙把千千万万的德国家庭分隔开来,许多居住在东部的德国人无法再去西部上班。沿墙而行的街道也都被割裂开来,许多交通工具无法再在那里行驶。 多年来很多东德人试图逃到西边去。图为1961年一名17岁的东德男孩翻越柏林墙,两名西德警察正在帮助他安全地下来。 柏林墙建成后,西柏林变成了一片孤独的、被敌视和被包围的土地。

The way的用法及其含义(二)

The way的用法及其含义(二) 二、the way在句中的语法作用 the way在句中可以作主语、宾语或表语: 1.作主语 The way you are doing it is completely crazy.你这个干法简直发疯。 The way she puts on that accent really irritates me. 她故意操那种口音的样子实在令我恼火。The way she behaved towards him was utterly ruthless. 她对待他真是无情至极。 Words are important, but the way a person stands, folds his or her arms or moves his or her hands can also give us information about his or her feelings. 言语固然重要,但人的站姿,抱臂的方式和手势也回告诉我们他(她)的情感。 2.作宾语 I hate the way she stared at me.我讨厌她盯我看的样子。 We like the way that her hair hangs down.我们喜欢她的头发笔直地垂下来。 You could tell she was foreign by the way she was dressed. 从她的穿著就可以看出她是外国人。 She could not hide her amusement at the way he was dancing. 她见他跳舞的姿势,忍俊不禁。 3.作表语 This is the way the accident happened.这就是事故如何发生的。 Believe it or not, that's the way it is. 信不信由你, 反正事情就是这样。 That's the way I look at it, too. 我也是这么想。 That was the way minority nationalities were treated in old China. 那就是少数民族在旧中

美国总统竞选演讲稿

美国总统竞选演讲稿 美国总统竞选演讲稿为了重塑美国中产阶级,我将给予95%的工人及其家庭税收减免待遇。如果你工作,就交税;如果年收入不足20万美元,你会获得减税;即使你的年收入超过了25万美元,你所负担的税率也比上世纪九十年代要低──资本利得税和股息税要比里根总统时期低三分之一。通过重建日益破败的基础设施、在美国的各个角落接通宽带,我们将创造200万个就业岗位。未来的十年中,我将每年在可再生能源领域投资150亿美元,进而新增500万个岗位;这些工作环保、薪酬丰厚、不能外包,而且能帮助我们摆脱对中东石油的依赖。在医疗问题上,我们不必在政府运营的体系和目前这种我们难以负担的体系之间进行选择。我的竞选对手提出的方案会令美国人有史以来首次为自己获得的医疗福利纳税。我的计划则会让医疗保健成为每个美国人都负担得起、享受得到的服务。根据我的计划,如果你已经有了医疗保险,你将看到的唯一一个变化是保费降低;如果你还没有医疗保险,你将能与国会议员们享受到同样的医疗福利。为了让每个孩子享受到世界级的教育,让他们能在全球经济中竞争21世纪的工作岗位,我将投资早期教育,并且增加师资力量。不过,我同时也会要求更高的标准和更多的责任。我们向每个美国年轻人作出承诺:如果你致力于服务你的社区或是你的国家,我们将确保你能负担得起自己的学费。在国防安全问题上,我将负责任地结束伊拉克战争,这样我们就不必在这个国家享有巨额财政盈余的情况下每月却要在那里花费100亿美元。为了美国的经济、美国的军队和伊拉克的长期稳定,现在是伊拉克人站出来的时候了。我将最终完成对本拉登(BinLaden)和基地组织恐怖分子的打击,正是这些人制造了9/11恐怖袭击,同时我还会建立新的合作关系、击退21世纪出现的威胁,恢复我们的道德威望,让美国仍然是地球上最后也是最好的希望。这些事情没有一件是轻而易举能办到的,也不是一朝一夕能完成的。但是,我坚信我们能成功,因为我对美国深信不疑。是美国使我们的父辈相信,即使他们自己无法上大学,也可以每周积攒下一些钱来,让他们的孩子接受好的教育;即使他们不能拥有自己的企业,也可以通过努力工作让自己的孩子创办企业。在美国历史的每个时刻,我们都勇敢地站起来面对挑战,因为我们从来没有忘记过这样一个基本真理:在美国,我们的命运并非天定,而是掌握在我们自己的手中。所以,明天,我恳请你们书写美国下一个伟大的篇章。我恳请你们不只相信我带来变革的能力,还有你们自己的能力。明天,你们可以选择这样一种政策──向美国中产阶级进行投入、创造新的就业岗位、实现经济增长让人人都有成功的机会。你们可以选择希望而非恐惧、选择团结而非***、选择变革的希望而非墨守成规。如果你们投我的票,我们将不仅赢得此次竞选,还将一起改变这个国家、改变这个世界。 感谢您的阅读,欢迎下载使用

(完整版)the的用法

定冠词the的用法: 定冠词the与指示代词this ,that同源,有“那(这)个”的意思,但较弱,可以和一个名词连用,来表示某个或某些特定的人或东西. (1)特指双方都明白的人或物 Take the medicine.把药吃了. (2)上文提到过的人或事 He bought a house.他买了幢房子. I've been to the house.我去过那幢房子. (3)指世界上独一无二的事物 the sun ,the sky ,the moon, the earth (4)单数名词连用表示一类事物 the dollar 美元 the fox 狐狸 或与形容词或分词连用,表示一类人 the rich 富人 the living 生者 (5)用在序数词和形容词最高级,及形容词等前面 Where do you live?你住在哪? I live on the second floor.我住在二楼. That's the very thing I've been looking for.那正是我要找的东西. (6)与复数名词连用,指整个群体 They are the teachers of this school.(指全体教师) They are teachers of this school.(指部分教师) (7)表示所有,相当于物主代词,用在表示身体部位的名词前 She caught me by the arm.她抓住了我的手臂. (8)用在某些有普通名词构成的国家名称,机关团体,阶级等专有名词前 the People's Republic of China 中华人民共和国 the United States 美国 (9)用在表示乐器的名词前 She plays the piano.她会弹钢琴. (10)用在姓氏的复数名词之前,表示一家人 the Greens 格林一家人(或格林夫妇) (11)用在惯用语中 in the day, in the morning... the day before yesterday, the next morning... in the sky... in the dark... in the end... on the whole, by the way...

“the way+从句”结构的意义及用法

“theway+从句”结构的意义及用法 首先让我们来看下面这个句子: Read the followingpassageand talkabout it wi th your classmates.Try totell whatyou think of Tom and ofthe way the childrentreated him. 在这个句子中,the way是先行词,后面是省略了关系副词that或in which的定语从句。 下面我们将叙述“the way+从句”结构的用法。 1.the way之后,引导定语从句的关系词是that而不是how,因此,<<现代英语惯用法词典>>中所给出的下面两个句子是错误的:This is thewayhowithappened. This is the way how he always treats me. 2.在正式语体中,that可被in which所代替;在非正式语体中,that则往往省略。由此我们得到theway后接定语从句时的三种模式:1) the way+that-从句2)the way +in which-从句3) the way +从句 例如:The way(in which ,that) thesecomrade slookatproblems is wrong.这些同志看问题的方法

不对。 Theway(that ,in which)you’re doingit is comple tely crazy.你这么个干法,简直发疯。 Weadmired him for theway inwhich he facesdifficulties. Wallace and Darwingreed on the way inwhi ch different forms of life had begun.华莱士和达尔文对不同类型的生物是如何起源的持相同的观点。 This is the way(that) hedid it. I likedthe way(that) sheorganized the meeting. 3.theway(that)有时可以与how(作“如何”解)通用。例如: That’s the way(that) shespoke. = That’s how shespoke.

里根就职演讲稿

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way 用法

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The way的用法及其含义(一)

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way 的用法

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