Application of carbon nanotubes in extraction and chromatographic analysis: A review

Zeid Abdullah ALOthman; Saikh Mohammad Wabaidur

doi:10.1016/j.arabjc.2018.05.012

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Review article

12 (

); 633-651

doi:

10.1016/j.arabjc.2018.05.012

Application of carbon nanotubes in extraction and chromatographic analysis: A review

Zeid Abdullah ALOthman^{^a,^b,⁎}, Saikh Mohammad Wabaidur^{^a}

a Advanced Material Research Chair, Chemistry Department, College of Science, King Saud University, Riyadh 11451, Kingdom of Saudi Arabia

b Chemistry Department, College of Science, King Saud University, Riyadh 11451, Kingdom of Saudi Arabia

⁎Corresponding author at: Chemistry Department, College of Science, King Saud University, Riyadh 11451, Kingdom of Saudi Arabia. zaothman@ksu.edu.sa (Zeid Abdullah ALOthman)

Received: 2018-3-15, Accepted: 2018-5-31, Published: 2018-07-01

Disclaimer:
This article was originally published by Elsevier and was migrated to Scientific Scholar after the change of Publisher.

Peer review under responsibility of King Saud University.

Abstract

Carbon nanotube (CNT), a well-known carbon-based nanomaterial has drawn much attention in many application fields including chemistry in the last few decades. Many researchers and scientists have shown huge interest to improve the extraction methodologies and adopt their applications in combination with chromatography technique. With respect to this, the exceptional applications of CNTs have been introduced as extraction sorbent due to their excellent inborn physical and chemical properties. In particular, CNTs have consistently been used as adsorbents in various techniques including solid-phase micro-extraction, solid-phase extraction, micro dispersive slid phase extraction, magnetic dispersive solid phase extraction, analytes enrichment, sample fractionation and clean-up as well as support for many derivatization reactions. Many research papers have discussed the successful use of CNTs to overcome the limitations of the extraction techniques due to their excellent sorbent capacity. In addition, considering the clear need to make chromatographic technique more successful, the applications of CNTs have been reported in the literatures in details as stationary and pseudo-stationary phases for the separation and extraction of challenging compounds. Because of the higher thermal and chemical stability, CNTs have been anticipated as stationary phase modifier for chromatographic applications to avoid bleeding of the columns and enable the analysis even at very high temperature (1200 °C). In liquid chromatography CNTs have primarily been used in combination with other packing materials (silica) and sometimes incorporated in a porous polymeric monolith. Therefore, the recent utilizations of CNTs as extraction materials and stationary phases have been illustrated in the current review and a table listing the details applications of CNTs in aforementioned field is provided as well. We believe that the review will help researcher to gain vast knowledge about application of carbon nanotubes in the field of separation chemistry.

Keywords

Carbon nanotubes

Extraction

Stationary phase

Chromatography

Application

Show Related Articles from PubMed

CNT (s): carbon nanotube (s)
SWCNT (s): single-walled carbon nanotube (s)
MWCNT (s): multi-walled carbon nanotube (s)
SPE: solid-phase extraction
SPME: solid phase microextraction
GC: gas chromatography
LC: liquid chromatography
CEC: capillary electro-chromatography
CE: capillary electrophoresis
HPLC: high-performance liquid chromatography
PAHs: polycyclic aromatic hydrocarbons
SEM: scanning electron microscopy
TEM: transmission electron microscopy
(d-SPE): dispersive solid phase extraction
(t_R): retention time
OT-CEC: open-tubular capillary electro-chromatography
ACN: acetonitrile
APTS: 3-aminopropyl-triethoxysilane
CRM: certified referenced material
DCM: dichloromethane
DMSO: dimethyl sulfoxide
DAD: diode array detector
FAAS: flame atomic absorption spectroscopy
FD: fluorescence detector
HSPIMP: 3-hydroxy-4-((3-silylpropylimino) methyl) phenol
MeOH: methanol
MIP: molecularly imprinted polymer
ODA: octadecylamine
o-MWCNTs: oxidized multi-walled carbon nanotubes
PDPA: polydiphenylamine
PDDA: poly(dimethyldiallylammonium)
PVA: poly(vinyl alcohol)
RRLC: rapid resolution liquid chromatography
TCD: thermal conductivity detector
UPLC: ultra-performance liquid chromatography
ECD: electron capture detector
FPD: flame photometric detector
m-dSPE: magnetic dispersive solid phase extraction
µ-dSPE: micro-dispersive solid-phase extraction
MEKC: micellar electrokinetic chromatography
m-NPs: magnetic nanoparticles
NIP: non-imprinted polymer
NPD: nitrogen phosphorus detector
UHPLC: ultra-high performance liquid chromatography

1 Introduction

Carbon nanotubes (CNTs) are the cylindrical allotrope nanostructures of carbon compose by rolling-up graphite planes with the diameters in the nanometer scale (Iijima, 1991; Dresselhaus et al., 1995; Thostenson et al., 2001 ). Two types of CNTs are mainly available, first one is single-walled CNT (SWCNT) and second one is multiwalled CNT (MWCNT) (Dresselhaus et al., 1995; Thostenson et al., 2001; Yakobson and Avouris, 2001 ). The SWCNTs are formed by rolled up single graphene layer into a seamless cylinder, while to prepare MWCNT, two or more graphene sheets are coaxially arrange around a central hollow core by the help of Vander Waals forces (Dresselhaus et al., 1995; Thostenson et al., 2001; Yakobson and Avouris, 2001 ). Based on the rolling angle of the graphene sheets they are called as armchair, zigzag and chiral (Fig. 1) (Madani et al., 2013). The special structural arrangements of CNTs provide exceptionally good inborn properties and become potentially useful materials for an extensive range of applications in the field of analytical chemistry. CNTs of various types have vastly been used individually or in conjugation with polymer composites in the field of photovoltaic applications as well, such as in solar cells (Jeon et al., 2017; Jeon et al., 2018; Ahn et al., 2018; Bhattacharyya et al., 2014; Kymakis et al., 2006; Rowell et al., 2006; van de Lagemaat et al., 2006 ). The application MWCNT can be found in the field of electrochemistry to modify the surface of glassy carbon electrode (Alothman et al., 2010; Wang et al., 2017; Wei et al., 2017 ). Wei et al. (2017) in their research work were used two types of metallic foams modified either with graphene or CNTs, and were applied them to discriminate rice wines with excellent results. The sp² covalent bonds presents between the carbon atoms of CNTs makes the materials strongest and hardest, because the sp² covalent bonds help to rise the tensile strength and elastic modulus of the materials. In general, the unique thermal and mechanical properties support the materials to use in other fields as well, including drug delivery, gene-therapy, neuro-engineering, chemical and biological sensor technology, and biomedical and tissue engineering. All these applications make CNT probably one of the most intensively studied nanostructured materials of different types (Goenka et al., 2014; Mundra et al., 2014; Meyyappan, 2004 ). The surface of the CNTs including SWCNTs and MWCNTs can easily be modified via the covalent or non-covalent bonding to improve the sorption capacity, and as well as thermal and chemical stability of the materials.

Models of single-walled and multi-walled CNTs and the various forms of SWCNTs (Madani et al., 2013).

In the last decades, plenty of methodologies based on pre-concentration and chromatographic separations have been established to improve the adsorption and retention efficiency of the sorbent materials. Regarding this, few research approaches have tried to incorporate a trivial quantity of carbonaceous nanomaterials into the porous stationary structure (Chambers et al., 2011a, 2011b; Aqel et al., 2012a; Mayadunne and El Rassi, 2014; Tong et al., 2013 ). Most commonly used material among them is CNT (Aqel et al., 2012b). Considering the large surface area and higher mechanical and thermal stability, CNTs have been used to produce sufficient interaction sites inside the sorbent and CNT has become an auspicious adsorbent material (Mayter and Elimelech, 2008). The earlier reports already have described the excellent adsorption capacity of CNTs and their application for the preparation of new stationary and pseudo-stationary phases (Speltini et al., 2013a, 2012, 2013b, 2014; Zhang and Qiu, 2015; Herrera-Herrera et al., 2012 ). The combination of the CNTs with other stationary phase was provided outstanding advantages to the separation techniques in terms of efficient separations. The potential applications of CNTs as stationary phases can be found substantially in the field of chromatography, including gas chromatography (GC), capillary electrochromatography (CEC), liquid chromatography (LC), etc. They have also been used as pseudo-stationary phases in capillary electrophoresis (CE) technique (Trojanowicz, 2006; Valcárcel et al., 2008; Scida et al., 2011; Peng et al., 2017; Herrero Latorre et al., 2012; Hemasa et al., 2017; Castillo-García et al., 2016; Pérez-López and Merkoci, 2012 ). Additionally, due to their good sorption capacity and capability to form a large numbers of interactions with foreign molecules, they have been very useful in many analytical fields, such as solid phase extraction (SPE) and solid phase microextraction (SPME) (Herrero Latorre et al., 2012; Ravelo-Pérez et al., 2010). In this review, a detailed outline for the latest applications of CNTs in liquid chromatography, gas chromatography, capillary electro-chromatography and for sample preparation has been discussed which are relevant to the chromatographers.

2 CNTs in separation techniques

In the recent years, countless efforts has been made to increase, modify and improve the separation efficiency of various stationary phases utilized in separation methods and especially in chromatographic techniques (Urban and Jandera, 2008; Zhang et al., 2006; Svec, 2010; Brett and Nesterenko, 2005 ). Carbon nanomaterials have received much attention to the improvements of chromatography technology and their applications mainly focus on the development of new stationary phases. In this regard, number of nanoparticles including gold (Lu and Chen, 2011; Xu et al., 2010; Yang et al., 2010a; Li et al., 2009a ), silica (Lu and Chen, 2011; Dong et al., 2008; Wang et al., 2006 ), zirconia (Duan et al., 2004) and fullerenes (Kartsova and Makarov, 2004; Moliner-Martinez et al., 2008) have been used earlier as stationary phases to attained improve selectivity and efficient separation in the high-performance liquid chromatography (HPLC), GC, capillary electro-chromatography (CEC) and capillary electrophoresis analysis. In addition, due to the versatile behaviors of carbon nanomaterials, they have been used as modifiers and stabilizers and it was reported that the introduction of CNTs have improved the chemical stability, selectivity and separation efficiency of chromatography technique (Pedrosa et al., 2010; Yang et al., 2010a; Chambers et al., 2011a ). The major applications of CNTs in the field of analytical chemistry are shown in Fig. 2.

Principal applications of CNTs in analytical chemistry.

However, the main challenges for the application of CNTs in analytical chemistry is to earn highly pure and well-characterized CNT materials (Hou et al., 2008). On addition, the commercially accessible CNTs are made of different diameters and lengths depending on the manufacturer, which undoubtedly disturbs their performances. Therefore, it is demanding to carefully chosen the type, dimensions and producer of CNTs to ensure their successful application in the laboratories.

2.1

2.1 CNTs in liquid chromatographic and electro-chromatographic applications

The use of CNTs as stationary phases in LC has explored in various research papers (Duan et al., 2011). The CNTs have mainly been used in combination with another silica based packing material or merged in a porous polymeric monolith (Peng et al., 2017). It has reported that the performances of the both SWCNTs and MWCNTs incorporated monolithic columns were improved due to the hydrophobic interactions between CNTs and the target compounds. The incorporation of MWCNTs in reversed-phase liquid chromatography has also found in the literature (Kwon and Park, 2006) and the combination of SWCNT with cellulose trisphenylcarbamate has reported to increase the enantio-selectivity of chiral column (Chang et al., 2007a). The bonding of SWCNT and functionalized SWCNT with 3-aminopropyl silica gel for the preparation of stationary phases were reported by many researchers, and were used such phases to separate various compounds including, polycyclic aromatic hydrocarbons (PAHs), terpenic compounds and polychlorinated biphenyl isomers (Chang et al., 2007b; Andre et al., 2009).

For example, Aqel et al. (2012c) of our group has published a paper reporting the effect of MWCNTs assimilation into benzyl methacrylate monolithic columns in capillary liquid chromatography. The work describes in details the preparation of polymer based monolithic materials and their application as stationary phases in preparation of capillary column. For this purpose, MWCNTs were incorporated into a mixture of co-monomers benzyl methacrylate and ethylene dimethacrylate. The cross-section and bulk region scanning electron microscopy (SEM) images, Optical micrograph (with a 100 × magnification) and Transmission electron microscopy (TEM) images of various columns are illustrated in Fig. 3. The efficiencies of the columns and the mobile phase flow rates tested by them at room temperature. The results for the separation of acetophenone, acetone, aminophenol, butyrophenone, chlorophenol and nitrophenol using the prepared columns are shown in Fig. 4. All the obtained results have been represented in terms of retention time (t_R), theoretical plate height (H) and resolution of the peaks (Table 1).

(a–c). Cross-section SEM images of C1, C2 and C3 columns respectively. (d–i) Bulk region SEM images of C1, C2 and C3 columns respectively. (j) Optical micrograph (with a 100× magnification) of C1 column. (k and l) TEM images showing the MWCNT structure for C3 column monolith. Adapted from reference (Aqel et al., 2012a) with permission from Royal Society of Chemistry.

Chromatograms on columns C1 (left) and C3 (right) of: (A) ketones with a binary acetonitrile/water (50:50, v/v) with 1% formic acid mobile phase at 1 mL min_1, where: (a) acetone, (b) acetophenone and (c) butyrophenone, (B) phenols using acetonitrile/water (50:50, v/v) with 1% formic acid mobile phase at 1.5 mL min_1, where: (a) aminophenol, (b) nitrophenol and (c) chlorophenol. Adapted from reference (Aqel et al., 2012a) with permission from Royal Society of Chemistry.

Table 1 Columns with and without CNTs, their efficiency and separation parameters in terms of retention time (t_R), plate height (H) and Resolutions of peaks (R_S) with flow rates 1 µL/min. Adapted from Ref. [63] with permission from Royal Society of Chemistry.

Components	Flow rate (µl/min)	Performances of columns
		Stationary phase without CNTs (C₁)			Stationary phase with CNTs (C₃)			H_c1/H_c3
		t_R/min	H/mm	R_s	t_R/min	H/mm	R_s	H_c1/H_c3
Acetone	1.0	15.36	0.716	–	15.41	0.092	–	7.78
Acetophenone	1.0	22.04	0.804	1.25	22.25	0.092	3.67	8.74
Butyrophenone	1.0	33.60	0.862	1.39	33.99	0.103	4.07	8.37
Aminophenol	1.0	10.32	0.366	–	14.12	0.136	–	2.69
Nitrophenol	1.0	13.97	0.448	1.44	19.42	0.140	2.61	3.20
Chlorophenol	1.0	17.91	0.485	1.10	24.75	0.143	1.96	3.39
Acetone	1.5	11.37	0.604	–	10.28	0.092	–	6.57
Acetophenone	1.5	16.30	0.636	1.39	14.70	0.101	3.48	6.30
Butyrophenone	1.5	24.90	0.733	1.54	23.33	0.112	4.24	6.54
Aminophenol	1.5	8.33	0.323	–	9.45	0.148	–	2.18
Nitrophenol	1.5	10.38	0.642	1.01	14.25	0.147	3.24	4.37
Chlorophenol	1.5	14.25	0.587	1.23	16.69	0.140	1.28	4019
Acetone	2.0	8.91	0.575	–	7.75	0.091	–	6.32
Acetophenone	2.0	12.99	0.641	1.46	11.27	0.090	3.77	7.12
Butyrophenone	2.0	19.30	0.653	1.49	16.95	0.114	3.83	5.73
Aminophenol	2.0	6.88	0.322	–	7.02	0.137	–	2.35
Nitrophenol	2	9.47	0.590	1.43	10.92	0.145	3.53	4.07
Chlorophenol	2	11.96	0.613	0.92	12.63	0.137	1.19	4.47

The incorporation of non-functionalized pure CNTs prevents the column bleeding and enables the column to operate at higher temperatures compared to other conventional columns (Valcárcel et al., 2005). Such type of modified columns was produced by deposit a thin layer of nanotubes on the surface of stationary phase through Chemical vapor deposition technique (Valcárcel et al, 2008). It has been claimed that the modification allows a better peak separation and shape and warned to consider the thermal stability carefully during the modification, because it has direct adverse effect on the column performance and reliability (Speltini et al., 2010). The number of literature in this field that concerns mainly the separation of standard mixtures of various compounds can be found in the literature. An example of separation of eleven acidic, neutral and alkaline organic components (sulphadimidine, resorcinol, aniline, p-toluidine, benzylalcohol, p-methoxybenzaldehyde, 2-naphthol, N,N-dimethylaniline, anisole, 1,3,5-trimethylbenzene and 2-methoxynaphthalene) on different PS-DVB columns containing 0%, 1% and 5% MWCNTs is provided in Fig. 5 (Zhong et al., 2010).

Separation of 11 organic compounds on (a) PS-DVB column, (b) PS-DVB-CNT columns (1% MWCNTs) and (c) PS-DVB-CNT column (5% MWCNTs). Column: PS-DVB and PS-DVB-CNT particles packed in 4.6 mm × 150 mm stainless-steel column. Mobile phase: methanol/water (90:10, v/v). Detection: UV detector with 254 nm. Flow rate: 1.0 mL/min. Peak identification: (1) resorcinol; (2) sulphadimidine; (3) benzylalcohol; (4) aniline; (5) p-toluidine; (6) 2-naphthol; (7) p-methoxybenzaldehyde; (8) anisole; (9) N,N-dimethylaniline; (10) 1,3,5-trimethylbenzene; (11) 2-methoxynaphthalene. Adapted from reference (Zhong et al., 2010) with permission from Elsevier.

CNTs easily immobilized onto the walls of silica capillaries through non-covalently or covalently bonding and those modified capillaries used to perform open-tubular CEC (OT-CEC) for the determination of different target compounds (Peng et al., 2017). Regarding this, various research paper reports the development of CNTs incorporated porous polymer monolithic capillary columns to achieve the enhanced separation of various small molecules (Chambers et al., 2011a; Hou et al., 2008). Among them, Chambers and his coworkers have described that the monolith column without CNTs modifications exhibited very low efficiency of only 1800 plates/m compared to modified column (Chambers et al., 2011a). The addition of a small quantity of MWCNTs was increased the efficiency of the column to greater than 15,000 plates/m at flow rates of 1 µL/min, and more than 35,000 plates/m when the flow set at 0.15 µL/min. The incorporation of small quantity of MWCNTs within porous silica beads helps to increase the affinity of the stationary phase towards aromatic compounds and provide better selectivity and retention to the column. There have found few applications of CNTs in chips to perform chip-CEC for the determination of thioamides, alkanes, colorings, and DNA fragments (Peng et al., 2017). In general, so far less works using CNTs have been reported in the chromatographic and electro-chromatographic fields, but the number of published papers likely to be more increase in future because of the interesting results of CNTs.

It has been noted that the resolution of chromatographic peaks and the plate number both reduced with the incorporation of MWCNTs (Zhong et al., 2010), but the applications of such materials increases day by day in chromatography field. Most of the reported works are only investigated for the text mixtures of analytes and the complex methodologies have not been established for the analysis of real samples. Another important issue regarding the application of CNTs as stationary phase that has not been considered in most of the research paper is the mechanical stability of the CNTs loaded stationary phase under different mobile phase flow environments. It can certainly be anticipated that the diameter, the length-to-diameter ratio and the number of CNTs will have a big impact with respect to the mechanical stability of the column. In this regard, it has been reported that the hydrodynamically driven flow systems required higher mechanical stability, as very high pressure applied in this systems (Mogensen and Kutter, 2012). Therefore, so much experimental evidences are still required in order to prepare CNTs incorporated stationary phase for the application in chromatographic separation with better understanding. In addition, further research is also demanded to understand the mechanism to achieve better electroosmotic flow on CNT-loaded stationary phases. Because, the oxidative state and/or the surface charge of the CNTs directly influence the retention properties of the column, which might makes the separation more challenging on such an electroosmotic flow system, compared to hydrodynamical flows based system.

The price of CNTs are also very important parameter, which can limits their applications in chromatography and separation science. Both CNTs powder and suspension are commercially available in a wide variety in terms of tube length, diameter and purity. Obviously, the application of CNTs is less expensive and very easy in the sense that the modification steps does not required any special equipment. The immobilization or deposition of CNTs on the stationary phases are easily performed by using their suspensions. Also according to various reported paper the regeneration of the CNTs and their reuses have been efficiently achieved once they used as extraction sorbent materials. However, the protocols needed for the purification and to prepare suspensions without the aggregation of the CNTs is quite labor intensive, challenging, and makes their applications limited.

2.2

2.2 CNTs applications in GC

The CNTs have anticipated preparing the stationary phases for GC because of their excellent adsorbent ability, intrinsic properties, and thermal and chemical stability. In very earlier literature, the application of both MWCNTs and SWCNTs can found in a GC packed column to separate halogenated and aromatic hydrocarbons, alkanes, ketones, alcohols, esters, ethers, etc. (Li and Yuan, 2003). The GC columns of various dimensions fabricated by self-assembly of a CNT film onto the capillary surface to prepare stable stationary phase and it was reported that the MWCNT modified column shown better selectivity and separation efficiency than SWCNT toward alkanes (Karwa and Mitra, 2006; Hussain et al., 2010). The use of SWCNTs as microfabricated stationary phase of GC capillary column has also reported in the literature (Stadermann et al., 2006). In other researches, SWCNTs were embedded to the inner surface of the capillary tubing to enhance the separation of alcohols, alkanes, ketones, aromatic compounds and racemate mixtures (Yuan et al., 2006; Zhao et al., 2011).

The application of homemade packed glass column using derivatized MWCNT found for the separation of alkanes and aromatic hydrocarbons (Speltini et al., 2010). Li et al. (2005) were combined SWCNT with an organic polymer and used them as monolithic stationary phase and better performance in terms of chromatographic retention of neutral molecules was achieved compared to a monolithic column without incorporated SWCNT. Detail lists of the applications of CNTs in sample preparations and chromatographic analyses listed in Table 2.

Table 2 Recent applications of CNTs in sample preparation and chromatographic analysis.

Target compounds	Real Sample	Types of CNTs used^a	Elution components	Method used	%age Recovery	LODs	Remarks	Ref.
3 sulfonamides	Milk	SWCNTs/C₁₈ and MWCNTs/C₁₈ (d.: 110–170 nm)	MeOH (0.1 mL)	CE-DAD	99–103	103 µg/L	[HMIm][PF₆] composite was used for sorbent preparation and MWCNTs/C₁₈ provided the better results than SWCNTs/C₁₈	Polo-Luque et al. (2013)
3 sulfonamide antibiotics	Sewage, Lake, and river water	MWCNTs (–)	5% NH3 in MeOH (1 mL)	HPLC-FD	80–90	–	µ-SPE; comparison with graphene, HLB, C₁₈, PCX, SCX sorbents	Sun et al. (2014)
Macrolides	Fish tissues	MWCNTs (–)	MeOH (3 mL)	UPLC–MS/MS	78–92	–	Comparison with C₁₈ and graphene	Wu et al. (2013)
Rhodamine B	Chili powder	MWCNTs-COOH (–)/MIPs	MeOH (5 mL)	UV	99	99–992570 µg/kg	Rhodamine B was used as template and the selectivity of sorbent was confirmed using: amaranth, carmine, sunset yellow and tartrazine	Liu et al. (2013)
5 aromatic hydrocarbons	Tap, bank filtrate, and wastewater	MWCNTs (–)	He (0.5 mL)	GC–MS	85	0.002–0.011 µg/L	HS-needle- µ-SPE
5 pharmaceuticals	Water	MWCNTs, MWCNTs-ODA, MWCNTs-COOH (–)	ACN (–)	HPLC-UV	–	0.08–4.5 µg/L	Comparison with C₁₈; needle- µ-SPE	Bhadra et al. (2011)
7 marine toxins	Shellfish muscle	MWCNTs (–)	5% NH4OH (v/v) in ACN (200 _L)	UPLC–MS/MS	70–90	–	Comparison with GP, HLB, Strata-X and C₁₈ sorbents; µ-SPE	Shen et al. (2013)
14 multiclass pesticides	Distilled and river water	MWCNTs (–)/PDPA	ACN (0.2 mL)	GC–MS	–	0.01–0.2 µg/L	_-SPE; sorbent packed in a syringe	Bagheri et al. (2012)
Rhein	Root of kiwi	MWCNTs (d.: 30–50 nm)/MIPs	MeOH:acetic acid 9:1 (v/v) (10 mL)	HPLC-UV–vis	80–92	–	Rhein as template	Chen et al. (2012a)
Oleanolic acid	Roots of kiwi	MWCNTs (–)/MIPs	10% acetic acid (v/v) (3 mL)	HPLC-UV	84–93	2.56 µg/L	Oleanolic acid as template	Chen et al. (2012b)
4 VOCs	Air	SWCNT/silica composite	–	GC–MS	–	0.001–0.01 µg/L	Comparison with PDMS and SPME CAR/PDMS cartridge	Heidari et al. (2012)
4 cobalamins	Pig liver (CRM), seafood	MWCNTs (d.: 9.5 nm)	DMSO (0.4 mL)	HPLC-DAD	76–102	0.35–30.0 µg/L	µ-SPE	Viñas et al. (2011)
5 polycyclic aromatic hydrocarbons	Water	CNTs (–)/Silica composite	–	GC–MS	74–114	0.001–0.01 µg/L	HS-needle- µ-SPE	Bagheri et al. (2011)
16 polycyclic aromatic hydrocarbons	River water 20 mL	MWCNTs (–)	ACN (0.1 mL)	GC–MS	72–99	4.2 × 10⁻³–46.5 × 10⁻³ µg/L	µ-SPE	Guo and Lee (2011)
16 polycyclic aromatic hydrocarbons	Surface water	MWCNTs (o.d.: 60–100 nm)	MeOH (0.4 mL)	GC–MS	72–93	0.001–0.15 _g/L	On line-SPE; µ-SPE	Wu et al. (2010)
16 PAHs	River water, tap and seawater	MWCNTs (i.d.: 60–100 nm)	n-hexane (15 mL)	GC–MS	70–127	0.002–0.0085 _g/L	Comparison with C₁₈	Ma et al. (2010)
3 PAHs Reservoir,	well and wastewater	MWCNTs (i.d.: 60–100 nm)/PVA	Hexane (15 mL)	HPLC-FD	89–98	0.005–0.008 _g/L	Comparison with C₁₈ sorbent	Kueseng et al. (2010)
Chloramphenicol	Egg, honey and milk	MWCNTs (d.: 40–60 nm)	ACN (5 mL)	HPLC–MS –	96–102	0.003–0.004 µg/L, 0.003 µg/kg	–	Lu et al. (2010)
7 sulfonylurea herbicides	Tap, spring, ground and well water	MWCNTs (d.: 60–100 nm)	1% acetic acid (v/v) in ACN (12 mL)	HPLC–MS/MS	82–111	1 × 10⁻⁵–2 × 10⁻⁴ µg/L	Comparison with C₁₈ sorbent	Fang et al. (2010)
Octane	Clean air	SWCNTs film/sealed Pyrex glass (–)	He (–)	GC-FID	–	–	_-SPE. On-line SPE	Takada et al. (2010)
Trans and cis-resveratrol	Red wine	MWCNTs (–)	0.1% formic acid:ACN 8:2 (v/v) (–)	HPLC–MS/MS	77–109	2 × 10⁻⁵ µg/L	On line-SPE	Lu et al. (2011)
11 triazine herbicides	River water	MWCNTs (i.d.: 40–60 nm)	ACN:H2O 9:1 (v/v) (5 mL)	RRLC–MS/MS	73–98	<1 × 10⁻⁴ _g/L	–	Yu et al. (2010a)
3 triazine herbicides	Water	MWCNTs (–)	Butyl acetate (0.22 mL)	GC–MS	–	–	µ-SPE; aniline-ortho-phenylene diamine, C₁₈, polypyrrole, charcoal sorbents; sorbent content in the PP membrane and the performance were checked	Bagheri et al. (2010)
2 sulfonylureas	Lake, creek, reservoir and underground water	MWCNTs (o.d.: 13–16 nm)	MeOH:ACN:H2O 50:2:48 (v/v/v) (0.250 mL)	CE-UV	86–108	0.40, 0.36 _g/L	On line-SPE; µ-SPE	Springer and Lista (2010)
Methane	–	MWCNTs (–)	N2	GC-TCD	–	–	On-line SPE; comparison was performed with other carbon based sorbents such as (CarbosieveTM, CarboxeneTM, CarbopackTM)	Saridara et al. (2010)
CO2	Flue gases	MWCNTs-APTS (–)	Thermal/vacuum desorption	GC-TCD	–	–	A comparison with the MWCNTs was tested; sorption studies (isotherms)	Hsu et al. (2010)
Mefenacet, hydroxybenzothiazole, N-methylaniline, 2-benzothiazoloxyacetic acid	River water	o-MWCNTs (i.d.: 40–60 nm)	Ethyl acetate (5 mL)	RRLC-UV-MS	86–101	0.02–0.04 µg/L	–	Yu et al. (2010b)
Bovine serum albumin	Bovine calf serum	Fe³O⁴/o-MWCNTs (–)/MIP	NaCl 5 mM (–)	HPLC-UV	92–97	–	Efficiencies of Fe₃O₄/o-MWCNTs (–)/MIP materials were compared with Fe₃O₄/o-MWCNTs (–)/NIP material; MIP-MWCNTs delivered better results; ovalbumin, bovine hemoglobin, human serum albumin and lysozyme were used to investigate the sorbent selectivity	Zhang et al. (2011a)
Methylene blue	Distilled	MWCNTs-COOH (o.d.: 10–20 nm)/biochar	–	UV–vis spectrometry	–	–	Sorption studies were performed and isotherm studies and mechanism were also discussed	Inyang et al. (2014)
9 triazine herbicides	River, well, tap water	MWCNTs (o.d.: 6–9 nm)	MeOH (2.5 mL)	UHPLC-UV	–	–	µ-dSPE; dispersion aided by effervescence precursors (NaH₂PO₄, Na₂CO₃) was checked	Lasarte-Aragonés et al. (2013)
Tetracycline	Water 25	MWCNTs, MWCNTs-OH and MWCNTs-COOH	AlCl3 3 M (10 mL)	HPLC-DAD	>80	–	µ-dSPE; CNTs of 2 different dimensions were tried for each sorbent and the MWCNTs of longest length showed the highest adsorption capacity	Zhang et al. (2011b)
40 multiclass pesticides	Apple, cabbage and potato	MWCNTs (o.d.: 10–20 nm)	–	LC–MS/MS	7–117	1–15 µg/kg	dSPE used as clean-up; MWCNTs were used in combine with 150 mg PSA and 750 mg of MgSO₄	Zhao et al. (2013)
6 perfluorinated compounds	Water	SWCNTs (o.d.: 2.1 nm), MWCNTs (o.d.: 6.7 nm, 23.2 nm, 30.2 nm, 56.1 nm), MWCNTs-OH (o.d.: 61.8 nm), MWCNTs-COOH (o.d.: 63.9)	–	HPLC–MS/MS	98–102	–	µ-dSPE; sorption studies (isotherm and mechanism); non retained analyte determined	Deng et al. (2012)
6 chemical warfare agents	Distilled, tap and muddy water	Fe₃O₄/o-MWCNTs (o.d.: 7–15 nm)	MeOH (800 µL) and chloroform (3 mL)	GC-FPD	56–96	0.05–1.0 µg/L	Results were compared with MWCNTs and C₁₈ in classical SPE; MWCNTs in classical SPE showed slightly higher recoveries; C₁₈ showed worse results	Pardasani et al. (2011)
78 multiclass pesticides	Tea	MWCNTs (o.d.: 20–30 nm)	–	GC–MS/MS	65–116	–	dSPE was used as clean-up in QuEChERS; MWCNTs were used in combination with 150 mg PSA and 750 mg of MgSO₄ with excellent results	Hou et al. (2014)
12 multiclass pesticides	Milli-Q water	MWCNTs (o.d.: 10–15 nm)	DCM (35 mL)	Nano LC-UV	36–102	0.02–0.87 µg/L	MWCNTs was regenerated and could be reused after washing	Asensio-Ramos et al. (2011)
Gatifloxacin	Serum	Fe₃O₄/o-CNTs (o.d.: 10–20 nm)/MIP	MeOH:acetic acid 6:4 (v/v) (5 mL)	HPLC-DAD	79–89	6 µg/L	m-dSPE; the obtained results were compared with other composite, e.g. m-NPs/MIP, Fe₃O₄/o-CNTs/NIP and m-NPs/NIP	Xiao et al. (2013a, 2013b)
6 polychlorinated biphenyls	Tap and river water 500 mL	Fe₃O₄/MWCNTs-COOH (o.d.: <5 nm)/PDDA	DCM:n-hexane was taken in the ratio 1:1 (15 mL)	GC–MS	71–99	0.027–0.059 µg/L	m-dSPE; the results obtained by proposed composite were compared with MWCNTs, MWCNTs-COOH/PDDA and C₁₈-NH2 and the results were similar in all cases	Zeng et al. (2012)
15 organophos-phorus pesticides	Run-off, mineral and tap water	MWCNTs (o.d.: 6–13 nm)	DCM (25 mL for run-off and tap water and 30 mL for mineral water)	GC-NPD	67–107	1.16 –93.6 ng/L	–	González-Curbelo et al. (2013)
8 Organochlorine pesticides (α-HCH, β-HCH, γ-HCH, heptachlor, aldrin, heptachlor epoxide, α-endosulfan and dieldrin)	Honey and tea	CoFe₂O₄/oMWCNTs (o.d.: 30–60 nm)	Ethyl acetate (200 _L)	GC-ECD	73–129	1.3–3.6 ng/L	µ-dSPE; m-dSPE	Du et al. (2013)
Bisphenol A, bisphenol F and their diglycidyl ethers	Tap, river and snow water	Fe₃O₄/o-MWCNTs (i.d.: 60–10 nm)	MeOH (5 mL)	GC–MS/MS	89–115	0.001–0.06 µg/L	m-dSPE	Jiao et al. (2012)
Triclosan	River and lake water	MWCNTs (o.d.: 60–100 nm)-MIP MWCNTs (o.d.: 60–100 nm)-NIP	Ethanol:HCl 6 M 1:1 (v/v)	HPLC-UV	91–95	–	Extraction efficiency and selectivity of CNTs-NIPs are much lower than those of CNTs-MIPs; several sorption studies were also developed	Gao et al. (2010)
11 sulfonamides	Milli-Q, low mineral content and very low mineral content water 250 mL	MWCNTs (o.d.: 6–9 nm) Fe₃O₄/MWCNTs (1:1, w/w), (1:2, w/w) and (1:3, w/w)	MeOH (25 mL)	UHPLC-DAD	40–110 for MWCNTs 46–77 for Fe₃O₄/MWCNTs (1:2, w/w)	7.00–32.0 ng/L	Different proportions of m-NPs and MWCNTs were combined (1:1, 1:2, 1:3) and tested; different amounts of sorbents were selected in order to maintain constant the mass of MWCNTs; results demonstrated the need of a drying step for m-CNTs	Herrera-Herrera et al. (2013)
3 estrogens	Honey, tap and mineral water 1.0 g (honey)	Fe₃O₄/MWCNTs-OH (o.d.: <8 nm)	MeOH (2 mL)	Sweeping- MEKC-UV	90–100	0.9–1.7 µg/L	m-dSPE	Guan et al. (2010)

a The amount of CNTs including SWCNTs and MWCNTs were taken in the range of 0.003–1000 mg.

2.3

2.3 Application of CNTs in extraction technique

The unique surface chemistry of CNTs such as p-conjugative structure with extremely hydrophobic surface and excellent porosity makes them highly efficient sorption materials compared to other conventional solid phase adsorbent materials. Number of articles have stated the usage of CNT for the extraction and quantitative detection of different target analytes using separation techniques (Hadjmohammadi et al., 2010; Li and Chi, 2009; Dong et al., 2009a, 2009b; Liu et al., 2009; Zhou et al., 2009 ). A recent study by Hadjmohammadi et al. (2010) reports the comparison of the extraction efficiencies of two components (chlorpyrifos and phosalone) using MWCNT and C-18 silica as the solid phase extraction adsorbents. It was shown by them that cartridges made of MWCNT tolerated much higher flow rates and in the same time used smaller quantities of dichloromethane for preconditioning. Also the limits of detection obtained with the MWCNT were almost 3 folds lower than that using C-18 silica. Another study by Li et al. (2009b) disclosed that oxidized CNTs are well suited for the extraction of a number of compounds from aqueous samples and was efficient as conventional Oasis HLB solid phase cartridges.

Our group was also used the MWCNTs as extraction adsorbent for the high-performance liquid chromatography analysis of polyphenol contents in different natural Yemeni honeys of various floral sources with excellent extraction recovery and regeneration properties (Badjah Hadj Ahmed et al., 2014). We have reported another ultra-high performance liquid chromatography coupled to mass spectrometry method for the simultaneous separation, identification and determination of many phenolic constituents in honey from various floral origin using MWCNTs as solid-phase extraction sorbents (Wabaidur et al., 2015). In this case, also the regeneration of solid phase adsorbent to be reused and recovery results were found to be excellent. The application of CNTs was further elongated by surface functionalization that generally revise their hydrophobic nature and was found their applications as hybrid silica monolith (Zheng et al., 2009; Mendoza et al., 2012; Huang et al., 2012; Wang et al., 2011 ) for the determination of sulfonamides in egg or other food samples.

2.3.1

2.3.1 CNTs as sorbent supports

Few unique characteristics of CNTs are responsible to make them ideal supports to deposit various coating materials such as polymers and MIPs on their surfaces. The depositions of MIPs onto CNTs were carried out for the preparation of highly selective extraction procedures (Turiel and Martín-Esteban, 2010). The MIPs linkage provides many additional advantages over conventional MIPs used in extraction procedures, such as greater mechanical power and chemical stability (Socas-Rodrígueza et al., 2014). All these properties greatly improves the accessibility of the template molecule and in the same time enhance the extraction efficacy. Also with non-supported MIPs or immune sorbents it was obvious that the high specificity hampers multi residue analysis, but the methodologies that use CNTs/MIPs can overcome these limitations and devoted to the analysis of closely related analytes. Therefore, to determine those organic (Xiao et al., 2013a, 2013b; Madrakian et al., 2013; Yang et al., 2014, 2013; Prasad et al., 2013, 2014 ) and inorganic (Ebrahimzadeh et al., 2013; Zhang et al., 2010a, 2010b ) compounds, which cannot be separated with traditional sorbents material was easily separated by using the CNTs/MIPs extraction sorbents.

2.3.2

2.3.2 CNTs in solid phase extraction (SPE)

In the last decade, SPE has become the very popular and traditional sample enrichment techniques and it has largely been used in the field of separation science. Compared to other different types of SPE adsorbents, CNTs are well reputed because of its π-conjugative structure, porosity and heterogeneity that dramatically facilitate the diffusion and extraction of solid materials (Yan et al., 2005).

Now from the detailed review of the aforementioned literature it can deduce that CNTs has the adequate sorption capacity to be used for the extraction of both inorganic and organic components. Furthermore, the changeable selectivity due to the introduction of non-covalent or covalent functionalization onto their surface has preferred their widespread usage in the field of extraction (Peng et al., 2017; Herrero Latorre et al., 2012; Ravelo-Pérez et al., 2010; Sitko et al., 2012 ).

However, there is a drawback of covalent functionalization, since it leads to the distortion of graphitic structure of CNTs and results significant changes in their physical properties. Even the whole graphitic structure can be destroyed if the amount of functionalization is too high. Regarding this in a recent work of Yang et al. (2010b) the influence of different concentrations of NaOCl on the oxidation of MWCNTs has been discussed. They have proved that when the tested percentages of NaOCl was highest, the CNTs structure destroyed and carbon found as larger agglomerated particles (Fig. 6).

FE-SEM images for (a) raw CNTs, (b) 1%, (c) 3%, (d) 5% and (e) 7% of o-CNTs. Reprinted from (Yang et al., 2010b) with permission of the Society of Chemical Industry.

The chemical interaction between CNTs and metal ions also occurs during the functionalization of the CNT surface and consequently the metal ions removal capability of CNTs increase due to the presence of large number of active sites on the inner cavities, surface, and inter-nanotube space (Pyrzynska, 2010). Additionally, the effect of pH is crucial for the adsorption studies and it was carefully been considered by the researcher during their experiment. Because, at the “point of zero charge” or “isoelectric point”, the electrical charge density on the CNTs surface is zero and the surface become negatively charged at a pH higher than that and vice versa (Boem, 2002). Thus, when the surface is negatively charged the adsorptions of cationic species are improved. On the other hand, when the pH is lower than “isoelectric point”, the protons might compete with metal cations to be adsorbed in the same sites on the surface of CNTs. Due to this phenomenon solutions having acidic additives are normally used to encourage the elution of metal ions. There are number of methodologies have been reported for metal ion extraction using oxidized CNTs (o-MWCNTs and/or o-SWCNTs). The oxidized CNTs were obtained by placing CNTs to a strong acid media at very high temperatures. Due to this, the introduction of —COOH, —OH and —CO— groups occur on the CNTs surfaces. Similarly, the immobilizations of organic molecules or biomolecules on CNTs surfaces have also been reported, and this further extend their applications (Sitko et al., 2012). Also there are enormous works have been developed to extract inorganic compounds from aqueous samples, while only a few reports have dealt with semi-solid or solid matrices (Peng et al., 2017; Ravelo-Pérez et al., 2010; Sitko et al., 2012 ).

The strong adsorptive capacity of CNTs for organic analytes has been attributed due to π-π electron donor-acceptor interaction between the aromatic system of organic molecules that work as electron acceptors and the highly-polarizable graphene sheets of CNTs which act as electron donors (Trojanowicz, 2006). Considering this fact, many authors have worked with as synthesized CNTs mainly for the extraction of pesticides (Ravelo-Pérez et al., 2010; Pyrzynska, 2011), pharmaceuticals, parabens, PAHs, phthalate esters, antioxidants, phenolic and so many biological compounds (Peng et al., 2017; Ravelo-Pérez et al., 2010).

On contrary, the functionalized or modified CNTs used more efficiently for the retention of polar organic analytes due to the more selective interaction of the functionalized CNTs (Trojanowicz, 2006; Zhao et al., 2012; Deng et al., 2005 ). The SEM images of pristine MWCNTs and composites of Fe/MWCNTs where the initial mass ratios of ferrocene with CNTs were (b) 1:1, (c) 2:1 and (d) 3:1 are shown in Fig. 7 (Zhao et al., 2012).

SEM images of (a) pristine MWCNTs and Fe/MWCNTs composites with an initial mass ratio of ferrocene to CNTs of (b) 1:1, (c) 2:1 and (d) 3:1. Adapted from reference (Zhao et al., 2012) with permission from Elsevier.

2.3.3

2.3.3 CNTs in solid phase microextraction (SPME)

The coating procedure is the most important task for performing CNTs modified SPME technique. A number of methods can be found in the literature to deposit CNTs in SPME fibers. The reported familiar techniques are chemical bonding, sol-gel method, electrophoretic deposition method, physical agglutinate, electrochemical polymerization technique, magnetron sputtering and atom transfer radical polymerization method (Samanidou and Karageorgou, 2012; Mehdinia and Aziz-Zanjani, 2013). Habitually, fused silica has normally been utilized as an appropriate SPME fiber material due the presence of silanol groups on the silica surface but they are fragile. Thus, the fragile fused-silica fibers were replaced by stainless steel wires to overcome such important limitation. The sol-gel technique has also been used vastly for preparing SPME fiber but it has shown inadequate reproducibility and make way for other optional technique, such as chemical bonding methods (Mehdinia and Aziz-Zanjani, 2013) where an electrochemical polymerization is occurred. The lack of bonding between the coating materials and the substrate generates low thermal stability fibers that can swell easily in organic solvents. Another method reported was Physical agglutination with adhesives to prepare fibers but it also showed low stability and resistance and the glues has the tendency to block the coating pores of the fibers or even can change the extraction selectivity. Similarly, electrophoretic deposition technique was emerged as an alternative SPME fiber preparing methodology to prepare stronger and more stable CNT-SPME fibers and was largely utilized for SPME technique (Peng et al., 2017; Ravelo-Pérez et al., 2010; Mehdinia and Aziz-Zanjani, 2013 ).

2.3.4

2.3.4 CNTs in dispersive solid phase extraction

It has been well reported that the extraction methods are surface-dependent as their kinetic directly relies on the contact area between the extracting sample and the sorbent phase. The better dispersion of the extractant directly enhances the contact area between the sample and stationary phase improving the extraction efficiency of the method. In this regard, Lasarte-Aragonés et al. (2013) have described in their research the effectiveness of CNTs dispersion in the micro-solid-phase extraction (µ-SPE) of certain herbicides from environmental waters samples (104). They were used methanol to eluted retained compounds from the analyte enriched MWCNTs. They optimized the µ-SPE technique for the determination of number of herbicides as model analytical problem in waters and determine them using ultra performance liquid chromatography (UPLC) combined with ultraviolet detection (UV) technique. Hou et al. (2014) were reported a multi-residue technique for the quantitation of pesticides in tea samples using MWCNTs as a dispersive solid phase extraction sorbent. Using their methods, it was possible to analyzed 78 pesticide residues in tea (Hou et al., 2014). The MWCNTs modified dispersive solid phase extraction (d-SPE) technique is easy, quick, cheap, effective, rugged and safe and was validated using gas chromatography in combination with tandem mass spectrometry (GC–MS/MS). The MWCNTs were reported to be a promising d-SPE sorbent material with excellent cleanup efficiency and suitable for the wide application of pesticide residues analysis. Many other applications of CNTs as d-SPE have been listed in Table 2.

2.3.5

2.3.5 CNTs in magnetic dispersive solid phase extraction (m-dSPE)

Xiao et al. (2013a, 2013b) have described a method for the preparation of molecularly imprinted magnetic dispersive SPE materials (m-dSPE) using magnetic CNTs as extraction sorbent and applied for the determination of gatifloxacin antibiotic in biological samples using HPLC technique. They have found that the adsorption using the magnetic CNTs imprinted polymers are rapid and possessed a high adsorption capacity toward gatifloxacin. The developed imprinted polymer was collected and separated them very fast using external magnetic field and shown exceptional mechanical properties with high surface-to-volume ratio. In addition, such type of MWCNTs incorporated polymer was re-generable and has shown negligible loss of recoveries after their uses for few cycles. In another research, Du et al. (2013) reported the synthesis of a novel magnetic SPE technique using MWCNTs in combination with cobalt ferrite and applied for the screening of pesticides mainly organochlorine pesticides in honey and tea samples with GC analysis. The developed MWCNTs modified SPE technique was used for the extraction of eight organochlorine pesticides with the enrichment factors ranging 52–68. In this research methodology, the MWCNTs were used as efficient components to extract both nonpolar and less polar target analytes from a complex matrix. A number of other applications of various CNTs in combination with other materials have been enlisted in Table 2 as well.

3 Conclusions

From the detailed studies mentioned above, it is obvious that the combination of unique structures, dimensions and surface morphologies make CNT an interesting sorption material, and so far, it has widely been used in research in the field of separation science. Although, applications of CNTs in GC and LC as stationary phases and in CE as pseudo-stationary phases are gaining much more attention. In the same time, their progressive applications in sample preparation techniques, mainly in SPE, has substantially increased and huge number of paper published in this area and few of them have been listed above in the tabular form. The unique properties of CNTs towards functionalization, binding of complex foreign molecules and solubilization makes them very exciting and powerful materials and rapidly expands their application in the field of separation chemistry. The CNTs are found to be a promising SPE sorbent material with excellent cleanup efficiency for the wide application for multi residues analysis. However, the relatively high cost of highly pure CNTs due to low yields during their synthesis steps make it difficult for their use in sample preparation. Therefore, a reduction in their prices will leads to the uses of these materials more common, particularly in sample preparation it will add lot of potential for the future applications. Although, the application of CNTs is less expensive in the sense that it does not need any special equipment for the modification purposes. Because, the immobiliztion of CNTs on various stationary phases can be performed easily by using their suspensions.

Acknowledgements

The authors are grateful to the Deanship of Scientific Research, King Saud University for funding through Vice Deanship of Scientific Research Chairs.

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Introduction

CNTs in separation techniques

CNTs in liquid chromatographic and electro-chromatographic applications
CNTs applications in GC
Application of CNTs in extraction technique

Conclusions

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Application of carbon nanotubes in extraction and chromatographic analysis: A review

Abstract

Keywords

Carbon nanotubes

Extraction

Stationary phase

Chromatography

Application

Abbreviations

1 Introduction

2 CNTs in separation techniques

2.1 CNTs in liquid chromatographic and electro-chromatographic applications

2.2 CNTs applications in GC

2.3 Application of CNTs in extraction technique

2.3.1 CNTs as sorbent supports

2.3.2 CNTs in solid phase extraction (SPE)

2.3.3 CNTs in solid phase microextraction (SPME)

2.3.4 CNTs in dispersive solid phase extraction

2.3.5 CNTs in magnetic dispersive solid phase extraction (m-dSPE)

3 Conclusions

Acknowledgements

References

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