Photoinduced EZ isomerization across the imine bond ...

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D. S. B. Campus, Kumaun University, Nainital-263 001 Uttarakhand, India .... bDepartment of Technology Management, The Open University of Kaohsiung, No.
J. Indian Chem. Soc., Vol. 94, February 2017, pp. 123-134

Photoinduced E-Z isomerization across the imine bond in a multi-responsive organogel affecting morphology and structure† Sanjoy Mondal and Arun K. Nandi* Polymer Science Unit, Indian Association for the Cultivation of Science, Jadavpur, Kolkata-700 032, India, E-mail : [email protected] Manuscript received 02 November 2016, accepted 30 December 2016 Abstract : A low molecular weight organogelator, (E)-N ′ -(anthracene-10-ylmethylene)-3,4,5tris(dodecyloxy)benzohydrazide (OG ) produces ther mo - and mechano-respon sive organogel in methyl cyclohexane. The organogel exhibits green fluorescent which is also retained in the xer ogel state. The gel exhibits fibrillar three dime nsional network morp hology with average diameter 45±8 nm. Rheological experi men ts reveal shear thinning and thixotropic properties of the gel. The fluorescence intensity of the gel is ~6 times higher than that of the solution with a 14 n m red shift indicating the J-type aggregate formation. On UV-irradiation at 365 nm E-iso mer of OG transforms into Z-iso mer in both gel and xerogel state and 1 H NMR spectra clearly points out the transforma tion. The kinetics of E-Z iso merization of OG in gel phase is carried out with d uration of photo-irradiation at different te mperatur es by fluorescence spectroscopy. The rate constant values of photo-isomerization of the gels are obtained from the intercepts of Avra mi plot and they are 0.16, 0.28, 0.31 and 0.49 mi n – 1 for 10, 20, 30 and 40 ºC, respectively. The increase of rate constants with te mperature indicates the process is Arrhenius type. The WAXS spectru m changes with UV-irradiation characterizing the formation of Z-isomer. On UV-irradiation for 24 h the fibers of OG gel transforms i nto microscopic crystals and the micro-crystallization occurs very fast in the xerogel state. The crystals are prominen t in 4.5 h of UV-irradiation as evident from the bright birefringence pattern of the crystals with mostly den dritic mor phology. Keywords : Self-asse mbly, organogels, supramolecular structure, morphology, photoisomerization.

J. Indian Chem. Soc., Vol. 94, February 2017, pp. 135-140

Synthesis and characterization of 1,2,4-triazole containing Schiff base ligands and their CuII complexes Arfa Parween and Subhendu Naskar* Department of Chemistry, Birla Institute of Technology, Mesra, Ranchi-835 215, Jharkhand, India E-mail : [email protected]

Fax : 91-651-2275401

Manuscript received online 24 March 2016, accepted 17 October 2016 Abstract : The condensati on of 4-amino-1,2,4-triazole with 4-(diethyla mino)salicylaldeyde, 5-Brsalicylaldeyde and 2-hydroxy-4-metho xybenzaldehyde in methanol to produce 1,2,4-triazole containing Schiff base ligands 2-((4H-1 ,2,4-triazole-4-ylimino)me thy l)-5-(diethyla mino)phe nol (L 1 H), 2-((4H-1,2,4triazole-4-ylimino)methyl)-4-bro mophenol (L 2 H ) an d 2-((4H-1,2,4-triazole-4-ylimino)methyl)-5metho xyphenol (L 3 H) respec tively. The ligands on reaction with Cu(ClO 4 ) 2 .6H 2 O in 2 : 1 molar ratio form Cu I I co mple xes (1-3) of general formula CuL 2 . The ligands and the co mple xes were characte-rized by means ele men tal analysis, FTIR, NMR, Mass, UV-Vis ible spectroscopy, luminesc ence spectroscopy. Electrochemical study on the ligands exhibit one oxidation pea k due to phenol to phenoxyl radical and

one or two reduction wave/s, while the Cu co mplexes show Cu I I / I I I oxidation an d one ligand based reduction. Cu I / I I oxidation is ma s ked inside the ligand based reduction processes. Keywords : 1,2,4-Triazole, Schiff base, UV-Vis spectra, cyclic voltammetry.

J. Indian Chem. Soc., Vol. 94, February 2017, pp. 141-149

Ethylenediaminetetraacetic acid catalyzed oxidative conversion of N-(2-hydroxyethyl)phthalimide to n-methylphthalimide by cerium(IV) in aqueous sulphuric acid medium : A kinetic and mechanistic approach M. D. Meti, M. Z. Pendari, S. A. Rayabag, N. S. Naik, M. B. Banimath, S. T. Nandibewoor and S. A. Chimatadar* P.G. Department of Studies in Chemistry, Karnatak University, Pavate Nagar, Dharwad-580 003, Karnataka, India, E-mail : [email protected] Fax : 91-836-2747884 Manuscript received online 25 March 2016, accepted 13 October 2016 Abstract : The reaction between cerium( I V ) and N-(2-hy droxyethyl)phthali mide (NH EP) is very slow in sulphuric acid mediu m at 25 ºC. However, the reaction is facile in presence of ethylenediammine tetraacetic acid (EDTA) in aqueous s ulphuric acid me diu m. The reaction between cerium( I V ) an d NHEP in pr esence of EDTA exhibits 1 : 1 (oxi dant : reduc tant) s toichiometry. The products are identified as ceriu m( I I I )-EDTA co mplex, n-methylph thali mide and for maldehyde. The order with respect to oxidant concentration is unity, whereas the order with respect to both subs trate and catalyst concentration is less than u nity. Increase in sulp huric acid concentration increases the rate of reaction. The order with respect to H + ion concentra tion is less than uni ty. The added product cerium( I I I ), did not have an y significant effect on the rate of reaction in presence of EDTA. The active species of oxidant is identified as CeSO 4 2 + . Based on the experi mental results a suitable mechanis m is proposed. The activation parame ters and ther mo dyna mic quantities are also determine d and discussed. Keywords : Ceriu m( I V ), oxid ation, N-(2-hydroxyethyl)phthalimide, EDTA catalyst, the r modyna mic para meters.

J. Indian Chem. Soc., Vol. 94, February 2017, pp. 151-157

Acoustical and thermodynamical parameters nanoparticles dispersed in aqueous hexylene glycol

of

aluminium

oxide

Mukesh Kumar, Neha Sawhney, Sa mriti Sharma, Amit Kumar Sharma and Meena Sharma* Department of Chemistry, University of Jammu, Jammu-180 006, Jammu & Kashmir, India E-mail : [email protected] Manuscript received online 28 August 2016, accepted 02 October 2016 Abstract : I n the presen t i nvestigation alu miniu m oxi de (Al 2 O 3 ) nanoparticles were synthesised by precipitation me thod using AlCl 3 as a starting material. The synthesised nanoparticles were characterised by X-ray diffraction (XRD), trans mission electron microscopy (TEM), scanning electron microscopy (SEM) and energy dispersive X-ray spectroscopy (EDX). These nanoparticles have been dispersed in base

fluid, an aqueous solution of hexylene glycol. Density ( ρ ), ultrasonic velocity (u) and viscosity ( η ) for these nanofluids have been measured at different concentrations as a function of te mperatures (T = 303.15 K, 308.15 K and 313.15 K). Using their values vari ous acoustical and ther mody na mical parameters have been deter mi ned. Keywords : Al 2 O 3 nanoparticles, base fluid, nanofluid, ultrasonic velocity, density, viscosity, acoustical parameters.

J. Indian Chem. Soc., Vol. 94, February 2017, pp. 159-169

Green synthesis and catalytic activity of composite NiO-Ag nanoparticles for photocatalytic degradation of dyes Hena m Sylvia Devi a , Th. David Singh* a and N. Rajmuhon Singh b a Department

of Chemistry, National Institute of Technology Manipur, I mphal-795 004, Manipur

b Department

of Chemistry, Manipur University, Imphal-795 003, Manipur

E-mail : [email protected] Manuscript received online 16 September 2016, accepted 02 October 2016 Abstract : Preparation of co mposite NiO-Ag an d i ts in dividual mo no metallic nanoparticles is de mons trated by u tilizing non-toxic and ab undan tly available tannic acid at room te mperature through an eco-friendly green aqueous technique. These mono metallic and composite nanoparticles were characterized using TEM, SAED, EDAX, p hotolu minenc es, Zeta potential, IR and UV-Vis spectroscopy. Monome tallic and co mposite nanoparticles have a narrow size distribution with s ph erical morphology. Moreover, the average diame ters of all these three different nanoparticles are almos t i dentical and ranges from 7 n m to 10 n m as mea sured fro m H RTEM. Co mparative catalytic efficacy of the nanoparticulate ma terials were studied e mpl oying photo degradation of a cationic (methyl violet) and anionic (me thyl orange) dye at room te mpera ture. NiO-Ag co mposite nano particles exhibits higher catalytic potential and the rate constants for photo degradation reactions follow the order of the reaction condition : k N i O - A g c o m p o s i t e N P s > k N i O N P s > K A g N P s > k u n c a t . Higher catalytic performance of the composite sys te m is attributed to the co mposition effect which basically results due to synergistic electronic effect. Keywords : Co mposite nanoparticles, green aqueous synthesis, me thyl violet, methyl orange, nanocatalyst, synergistic effect.

J. Indian Chem. Soc., Vol. 94, February 2017, pp. 171-179

Synthesis and oil displacement experiment on sulfobetaine-type fluorocarbon surfactant system Pengcheng Liu* a , Qing Tian a , Jing Xia b , Mingqiang Hao b , Yuwei Jiao b and Chao Wang a a School

of Energy Resources, China University of Geosciences, Beijing 100083, China

E-mail : [email protected]

b Research

Institute of Petroleum Exploration and Development, PetroChina Beijing, 100083,

China Manuscript received online 02 October 2016, accepted 02 October 2016 Abstract : S ulfobetaine-type fluorocarbon surfactant (FS) was synthesized by reaction of N-[3(di me thyla mino)-propyl]-perfluoroal kyl sulfonami de (NFA) with 2-hydroxy-3-chloropropyl sodiu m in an al kaline environ men t. As in d icated by the foam performa nce tests, FS has the opti mal foaming and foam stability at the concen tration of 0.2 wt%. The oil displacemen t experi men ts in san d-pac ked tube and nu merical si mulation methods were conducted with the binary foam-co mplex flooding system inclu ding FS (0.2 wt%) + hydrolyzed polyacryamide (HP AM 1000 mg/L) and N 2 in alternating injection slugs. The results showed that the bina ry foam-co mplex flooding syste m could enhance oil recovery by 32.06% over the water flooding; the ultimate oil recovery was up to 76.58%. A mechanistic si mulati on study has been developed by the CM G-STARS si mulator with matching the oil recovery in comparis on with laboratory data. The simulation data fit well with tests data in sand-pac k tu be. HPAM can imp rove the mobility ratio of the surfactant to crude oil, thic ken the flooding mediu m and increase the sweep volu me. Meanwhile, FS can emulsify crude oil and increase the vi scosity of the flooding system which can in turn increase the washing oil efficiency. The binary foam-complex flooding syste m can greatly enhance oil recovery after water flooding. Therefore, FS and its comp lex syste m have great potenti al application and broad prospect to enhance oil recovery in oil fields. Keywords : Fluorocarbon surfactant, hydrolyzed polyacryamide (HP AM), syn thesis, foaming, oil displacement, nu merical si mulation.

J. Indian Chem. Soc., Vol. 94, February 2017, pp. 181-189

Comparative in vitro antioxidant activity, morphological and phytochemical profiling of traditional crops from Kumaun Himalaya P. S. Bungla a , G. Tewari* b , R. S. Rawal c , I. D. Bhatt c , L. M. Tewari a , A. K. R. Jugran c and B. Mohan a a Department

of Botany, b Department of Chemistry, D. S. B. Campus, Kumaun University, Nainital-263 001 Uttarakhand, India E-mail : [email protected]

Fax : 91-5942-235576

c G.

B. Pant National Institute of Himalayan Environment and Sustainable Development, KosiKatarmal, Almora-263 643, Uttarakhand, India Manuscript received online 17 October 2014, accepted 06 October 2016 Abstract : The phytoche mical attributes inclu ding proteins, carbohydrates and phenolic content of paddy landraces, millets, pulses, spi ce and oil yielding crop have been investigated along with the morphological properties of nineteen paddy landraces. In vitro antioxidant activity was assessed by ABTS, DPPH radical scavenging method an d FRAP assay. The morp hological characters varied significantly. Hordeum vulgare, Panicum glaucum , Setaria italic and Panicum m iliaceum were having much higher protein and carbohydrate contents as compared to most of the studied landraces of paddy. ABTS activity ranged between 0.24 and 354.06 mM/ 100 AAE while DPPH from 9. 00 to 107.90 mM/100 AAE. FRAP assay ranged between 0.016 to 383.20 mM /100 AAE. Badpas rice had the highest ABTS (354.06), DPPH (107.90) and FRAP (383.20) activity. Among millets, Hordeum vulgare had the highest an tioxidant activity whereas lowest activity was observed for Panicum m iliaceum and Setaria italic. Antioxidant activity of paddy

landraces, pulses and oil yielding crop were positively and significantly correlated to the total phenolic content. Keywords : Phytoche mical, phenolics, morphological, Kuloor watershed, antioxidant activity, traditional crops.

J. Indian Chem. Soc., Vol. 94, February 2017, pp. 191-194

Terpenoid composition and antimicrobial activity of essential oil from Torilis japonica (Houtt.) DC. G. C. Kharkwal a , C. Pande a , G. Tewari* a , A. Panwar b and V. Pande b a Department

of Chemistry, Kumaun University, Nainital-263 002, Uttarakhand, India

b Department

of Biotechnology, Bhimtal Campus, Kumaun University, Nainital, Uttarakhand, India

E-mail : [email protected] Manuscript received online 04 March 2015, accepted 06 October 2016 Abstract : Che mical composi tion of Torilis japonica (Houtt.) DC. growing wild in the central Himalayan region, was analyzed by capillary GC and GC-MS. The oil was found to be rich in sesquiterpine hydrocarbons (59.47%). A total of 44 compoun ds were identified representing 9 4.28% of the oil. Ger macrene D (25.86%), α -hu mulene (14.64%), β -caryophyllene (11.33%), nootkato ne (10.80%) and caryophyllene oxide (5.07%) were found to be the pr incipal constituents. T. japonica essential oil de mons trated bactericidal and fungicidial activity against six bacterial strains and two fungal strains respectively by agar well diffusion method. Keywords : Torilis japonica, Apiaceae, terpenoid co mposition, α -hu mulene, ger macrene D, anti microbial activity.

J. Indian Chem. Soc., Vol. 94, February 2017, pp. 195-200

In vitro anti-inflammatory activity of a new triterpenoid saponin from the stems of Glirisidia sepium Jacq. R. N. Yadava* and Nidhi Asati Natural Products Laboratory, Department of Chemistry, Dr. H. S. Gour Central University, Sagar470 003, Madhya Pradesh, India, E-mail : [email protected] Manuscript received online 15 March 2016, accepted 06 October 2016 Abstract : A new triterpenoi d saponin (1) has been isolated from the methanolic extr act of the ste ms of the Glirisidia sepium Jacq. along with a known compoun d 3-O-[ α - L -arabinopyranosyl-(1 → 3)- α - L rha mnopyranosyl-(1 → 2)- α - L -arabinopyranosyl]-28-O-[β β - D -glucopyranosyl-(1 → 2)-{β β - D -glucopyranosyl(1 → 6)}-β β - D -glucopyranosyl]-29-hydroxyhederagenin (2). A new compound 1 has m.p . 272–274 ºC, m.f. C 4 6 H 7 4 O 1 7 , [M] + m /z 898 was characterized as 3-O-[ β - D -xylopyranosyl-(1 → 4)]- α - L -arabinopyranosyl echinocystic acid 28-O-β β - D -galactopyranosyl ester by various colour reactions, chemica l degradations and spectral analysis. In vitro anti-infla mma tory activity of compoun d 1 showed significant effect against hu man red blood cell (HRBC) me mbrane stabilization.

Keywords : Glirisidia sepium Jacq., Fabaceae, ste ms, triterpenoid saponin, bides mosidic, anti-inflammatory activity.

J. Indian Chem. Soc., Vol. 94, February 2017, pp. 201-203

Chemical composition of leaf essential oil of Hyptis suaveolens (L.) Poit Vineet Kandpal, Prasoon K. Joshi and Neeta Joshi* Department of Chemistry, M. B. G. P.G. College, Haldwani (Nainital)-263 139, Uttarakhand, India, E-mail : [email protected] Manuscript received online 09 January 2016, accepted 06 October 2016 Abstract : Essen tial oil of leaves of Hyptis suaveolens (L.) Poit collected from Ku maon region of Uttara khand state of In dia was obtained by stea m distil lation using clevenger apparatus. The oil were analyzed by GC and GC-MS . 27 Compounds consti tuting 87.70% of total oil have been identified, the ma jor ones being 1,8-cineole (17.61%), E-caryophyllene (15.23%), sabinene (9.42%), terpinolene (8.87%) and bicyclogermacrene (5.52%). Keywords : Hyptis suaveolens (L.) Poit, es sential oil, 1,8-cineole, E-caryophyllene, sabinene, terpinolene, bicyclogermacrene.

J. Indian Chem. Soc., Vol. 94, February 2017, pp. 205-212

Design, synthesis and molecular recognition properties of pyridine-based hetero bis amide receptors Kumaresh Ghosh* a and Suman Adhikari a,b a Department

of Chemistry, University of Kalyani, Kalyani-741 235, West Bengal, India

b Department

of Chemistry, Government Degree College, Dharmanagar-799 253, Tripura, India

E-mail : [email protected] Manuscript received online 22 December 2015, accepted 21 October 2016 Abstract : Two new pyridine-based hetero bis amide receptors 1 and 2 has been designed and synthesized. The recognition properties of these newly formed receptors were investigated by 1 H NMR, UV-Vis spectroscopy and fluorescence methods. They are found to be effective in hosting α -hyd roxy and α -a mino acid derivatives into the open clefts. Keywords : Hetero bis amide receptors, α -hydroxy acids, α -a mino acids, hydrogen bonding.

J. Indian Chem. Soc., Vol. 94, February 2017, pp. 213-220

Protective effect of black rice extract on the functional status of liver and hepatic stellate cell against toxicity induced by ethanol Suhailah S. Al-Jameel* a and Mashal M. Al-Na mshan b a Department

of Chemistry, b Department of Biology,

College of Science, University of Dammam, Saudi Arabia E-mail : [email protected] Manuscript received online 05 February 2016, accepted 21 October 2016 Abstract : The present stud y was performed to investig ate the protective effect of blac k rice ethanolic extract (B REE) on liver in jur y induced by e thyl alcohol in male rats. The s tudy was con ducted on 40 male Wistar rats weighing (190–200 g), the animals were divided into 4 equal groups. The first group was received basal diet and used as a normal control group (NC). The second group were ad ministered ethyl alcohol (6 g/kg bw) orally and used as positi ve control (PC). The other groups of rats were administered ethyl alcohol (6 mg/ kg bw) + BREE (125 and 250 mg/ kg b w/day). Blood and tissue samples were collected after 2 wee ks. The results revealed that the rats treated with ethyl alcohol showed a significant (p ≤ 0.05) increase in levels of TC, TL, TG, ALT and AST. E thyl alcohol intoxication induces so me pathological alterations in the liver as de generation of cytoplasm and nuclei manifest clear sympto ms of py knosis and karyorrhexis. The rise in seru m hepatic enzy mes, TC, TL, TG, histopathological and i mmunohistoche mical changes were significantly attenuated by BREE. The current results clearly investigate the beneficial effects of BREE in controlling ethyl alcohol disorders induced an d the protection of liver against ethyl alcohol intoxication. Keywords : Antioxidan ts, bla c k rice extract, ethanol, i mmunohistoche mical, free radicals, rats.

J. Indian Chem. Soc., Vol. 94, February 2017, pp. 221-228

The application of multivariate statistical analysis to the analysis of characteristics and assessment methods of heavy metal soil contamination in Taiwan Wu-Chou Yu a , Shu-Lung Kuo* b and Yi-Ching Fu a a Department

of Environ. Engineering & Science, National Pingtung University of Science and Technology, 1, Xuefu Road, Neipu Township, Pingtung County 912, Taiwan E-mail : [email protected] b Department

of Technology Management, The Open University of Kaohsiung, No. 436, Dar-Ye North Road, Kaohsiung City 812, Taiwan, E-mail : [email protected] Manuscript received online 29 August 2016, accepted 02 October 2016 Abstract : This research use s data from heavy me tal soil monitoring collected in 23 countries and cities across Taiwan by the Envir on mental Protection Ad mini stration (EPA), Taiwan. Multivariate statistical analysis methods are applied to investigate the relationships a mong the variables of the eight major heavy metals, hoping to find the principal factors that a ffect soil contamination and the conta mi nation tendency in Taiwan. The discussion of relationships a mong the eight heavy metals (i.e. chromiu m (Cr ), Ni (nic kel), Cu (copper ), Zn (zin c), Hg (mercury), Cd (cad mi u m), As (arsenic), and P b (le ad)) can reflect the difference in the conta minati ons in affected areas and conta mination level assess ment mo dels. The results of the factor analysis show that the principal factors affecting the conta mination mec hanis m of the eight

heavy me tals can be simplified into two : (1) Highly oxidizing pollutants comprised of Cr, Ni, Cu, and Zn. The loading capacity order from high to low is Cr, Ni, Cu , and Zn, which corresponds to several rules on the periodic table. (2 ) The s e miconductor poten tial pollutant factor co mprised of Cd, As, an d Pb. The factors, either the transition me tal Cd or the typical elements, As and Pb, all have some thing to do with the formation of a compoun d se miconductor. The major mechanis m for semiconduc tor formation is the metallic bond. As for the cluster analysis, five clusters are first divided according to the contamination characteristics. Discriminant analysis is used to classify the type of a new sample with an accuracy as high as 96.87%. This mean s that the clu stering for th e cluster analysis is acceptable. The research findings can serve as reference ma terial for relevant entities in the planning and application of soil reme diation strategies. Keywords : Soil me tal, multi variate statistical analysis, factor analysis, discriminan t analysis, soil pollution.

J. Indian Chem. Soc., Vol. 94, February 2017, pp. 171-179

Synthesis and oil displacement experiment on sulfobetaine-type fluorocarbon surfactant system Pengcheng Liu* a ,Qing Tian a, Jing Xia b, Mingqiang Hao b, Yuwei Jiaob and Chao Wanga aSchool

of Energy Resources, China University of Geosciences, Beijing, 100083, China

E-mail : [email protected] bResearch

Institute of Petroleum Exploration and Development, PetroChina, Beijing, 100083, China

Manuscript received online 02 October 2016, accepted 02 October 2016 Abstract : Sulfobetaine-type fluorocarbon surfactant (FS) was synthesized by reaction of N-[3-(dimethylamino)-propyl]perfluoroalkyl sulfonamide (NFA) with 2-hydroxy-3-chloropropyl sodium in an alkaline environment. As indicated by the foam performance tests, FS has the optimal foaming and foam stability at the concentration of 0.2 wt%. The oil displacement experiments in sand-packed tube and numerical simulation methods were conducted with the binary foamcomplex flooding system including FS (0.2 wt%) + hydrolyzed polyacryamide (HPAM 1000 mg/L) and N 2 in alternating injection slugs. The results showed that the binary foam-complex flooding system could enhance o il recovery by 32.06% over the water flooding; the ultimate oil recovery was up to 76.58%. A mechanistic simulation study has been developed by the CMG-STARS simulator with matching the oil recovery in comparison with laboratory data. The simulation data fit well with tests data in sand-pack tube. HPAM can improve the mobility ratio of the surfactant to crude oil, thicken the flooding medium and increase the sweep volume. Meanwhile, FS can emulsify crude oil and increase the viscosity of the flooding system which can in turn increase the washing oil efficiency. The bina ry foam-complex flooding system can greatly enhance oil recovery after water flooding. Therefore, FS and its complex system have great potential application and broad prospect to enhance oil recovery in oil fields. Keywords : Fluorocarbon surfactant, hydrolyzed polyacryamide (HPAM), synthesis, foaming, oil displacement, numerical simulation.

Introduction Surfactant, even at the extremely low concentration, can apparently reduce the surface tension of the solvent. As an important special surfactant, fluorocarbon surfactant (FS) has currently the highest surface activity, which is better in the temperature resistance and has the chemical stability than other surfactants1. FS, entitled the “Industrial Monosodium Glutamate”, has a wide range of applications in a lot of technical and economic fields, such as petroleum, firefighting, chemistry, and rubber manufacturing1,2. The mixtures of the surfactants with the high-molecular water-soluble polymer would have much better effects than before2,3. In the chemical flooding of the oil fields, it’s essential to use surfactant for surfactant flooding, complex flooding and foam flooding. The mixed system of FS has abilities of higher temperature resis-

tance, higher salinity and higher acidity, as well as the better foam properties than others4. The surfactant plays an important role in enhancing oil recovery (EOR)1,3–5. Therefore, FS has great potential application potential and broad prospect in EOR area1,6. In recent years, many experts have made a lot of researches in the development and the synthesis of FS and also have achieved great progress after the first occurrence of FS in 1951. Abe et al.7 researched the surface activity of the C6H5CF(CF3)O[CF2CF(CF3)O]mC3F7 with different ether linkages, which showed it is particularly effective in reducing the surface tension. Sawada et al.8,9 prepared the perfluorinated propyl- and fluoroalkylated 4-vi nylpyr idinium chlori de oli gome rs, and the fluoroalkylated allyl- and diallylammonium chloride oligomers, which can reduce the surface tension by 10 mN/ m. Guittard et al.10 synthesized the nonionic surfactants 171

J. Indian Chem. Soc., Vol. 94, February 2017 of the type polyoxyethylated monomethylated and con-

mers (e.g. hydrolyzed polyacryamide (HPAM), polyvi-

taining a fluorinated tail from 2-(F-alkyl) ethylamines.

nyl pyrrolidone (PVP), and hydroxyethyl cellulose (HEC))

These compounds are also effective to reduce the surface

can not only achieve much higher surface activity, but

al.11

also can reduce the cost in applications. The complex

synthesized two fluorine alkyl con-

flooding in EOR processes refers to the chemical flood-

taining sulfonic acid group fluorocarbon surfactants with

ing combining two or more chemical components19,20.

the material of perfluorinated alkyl alcohols, oxalic acid

The polymer-assisted surfactants are defined as the thick-

anhydride and so on, which can reduce the critical micelle concentration (CMC). Stoilov discovered that the

ness of surfactant flooding or the surfactant reinforced

volatile vapors of fluorocarbon substances such as C6F14,

lot of useful work in the aspect of mixture to research the

tension as nonionic fluorinated surfactants. Mao et and Kondo et

al.12

C8F18 and C10F18 have surface active

properties13. Mean-

while, many liquids could change their surface tensions at the range of 10–30% by contacting with C8F18 vapor at room temperature. Zhao and He introduced non-surface active organic ammonium salts into the sodium perfluorooctanoate to synthesize the sodium perfluorooctanoate-trimethylamine hydrochloride, which showed that the surface activity can greatly increase by adding non-surface active organic ammonium salts. The more the amount of the organic ammonium salts are, the more the surface activity increases, which is suitable for practical applications14. Rodríguez et al. developed the phosphocholine-based fluorinated surfactants which showed that the novel fluorinated surfactants perform high surface activity not only in water but also in organic solvents such as m-xylene and methanol, especially at low pH values15. Eastoe et al. synthesized four kinds of

polymer flooding21–23. In recent years, there has been a mixed system done by surfactants experts24–29. Binary foam-complex flooding technology (e.g. polymer and surfactant) is a mature flooding technology in EOR. Combining the foam system with the advantage of “emphasize” and the binary complex system with the asset of “strong washing oil” can form the property of “emphasize the strong washing oil” when mixing the surfactants with the high-molecular polymers, especially with the soluble polymers (e.g. HPAM)30. Binary foam-complex flooding technology can not only control the oilwater mobility ratio and greatly increase oil recovery, but also reduce the damage to the environment. Meanwhile, the technology can be made full use for other fields in the reservoir development such as well drilling, profile control, water plugging, fracturing and acidizing, and so on31,32. Recently, many oil fields have entered the middle and

non-ionic surfactants in order to research their surface adsorption and micellization properties16. A strong struc-

extra-high water cut period in the world. It is essential to

ture-activity relationship was observed, and the surface

develop these oil fields under the severe conditions, such

tension could be reduced by 9 mN/m. Ngo et al. synthe-

as extra-high water cut, high salt, high temperature, low

sized a series of perfluorinated cationic surfactants in order to research their aggregation and surface activity. They

permeability, and so on. Therefore, there are more and

discovered that FS can create layered spherical oil and

However, to the best of our knowledge, aimed at sur-

gas accumulation zone, and their CMC and oil/water in-

factants, previous research mainly focused on the lab

terfacial tension are lower than those of the hydrocarbon surfactants17.

evaluation for special properties, failing to consider it as

Although FS has an excellent surface activity, it is

recovery. In addition, the current existing surfactants have

much more expensive, which restricts its applications in

many kinds of disadvantages, such as salt sensitive, poor

EOR area18. However, mixing FS and hydrocarbon surfactants (e.g. A-olefin sulfonate (AOS)) or other poly-

stability to temperature, instability of foam properties,

172

more high demands and standards to the surfactants.

a good oil displacement system to further enhance oil

etc.33. Fluorine-containing surfactants have good proper-

Liu et al. : Synthesis and oil displacement experiment on sulfobetaine-type fluorocarbon surfactant system

fields34,35.

The conventional surfactant is made up by one nonpolar part RF (the oil-wet part of the fluorocarbon chain) and one polar part “X” (hydrophilic part). There are four kinds of fluorocarbon surfactants according to the differences of the “X” as same as the conventional hydrocar-

For its potential use in EOR area, we synthesized the sulfobetaine-type fluorocarbon surfactant by reaction of

bon surfactants, which are anionic, cationic, nonionic and amphoteric types of fluorocarbon surfactants. Moreover,

N-[3-(dimethylamino)-propyl]-perfluoroalkyl sulfonamide

based on the different structures of the anionic, there are some kinds of RFCOO–M+, RFSO3–M+, RFOSO3–M+,

ties of high surface activity, thermal resistance, salt tolerance, acid/alkali resistance, chemical stability and good foam performance, etc., which can meet the needs under the harsh conditions to enhance oil recovery in oil

(NFA) with 2-hydroxy-3-chloropropyl sodium in an alkaline environment. It also has good thermal resistance, salt tolerance, and acid/alkali resistance properties36,37. Moreover, its foaming properties and stabling foam properties were measured by Ross-Miles method. The oil dis-

RFOP(O)O22–M2+, etc, where, RF is fluorocarbon hydrophobic group (hydrophilic group), and “M” is inorganic or organic cation. Instruments and materials :

placement experiments in sand-pack tube and simulation methods by CMG-STARS simulator were conducted with

Instruments : Thermostatic drying oven and electricheated thermostatic water bath.

the binary foam-complex flooding system including FS

Materials : Twice-distilled water; perfluorooctane sulfonyl fluor ide (98 wt %), N,N-di me thyl -1,3propanediamine (organic amine); isopropyl ether (chemically pure), methanol (analytically pure); epoxy chloropropane (analytically pure); isopropanol (analytically pure) and anhydrous sodium carbonate (analytically pure).

(0.2 wt%) + hydrolyzed polyacryamide (HPAM 1000 mg/L) and nitrogen (N2) in alternating injection slugs. The oil displacement mechanism of the binary foam-complex flooding system was discussed based upon the incremental oil recovery. The results showed that the binary foam-complex flooding system can greatly enhance oil recovery after water flooding. Therefore, FS and its complex system have great potential prospects in EOR, and the binary foam-complex flooding technology is suitable for application after the conventional water or polymer flooding in oil fields. Experimental Synthesis of “FS” : Structure of “FS” : FS refers to one surfactant of containing the fluorocarbon chain hydrophobic groups, whose hydrogen atoms of the hydrocarbon chains have been displaced by the fluorine in whole or in part. The structure of FS is shown in Fig. 1.

Fig. 1. Structure of the fluorocarbon surfactant.

Synthesis procedures : (1) The synthetic of intermediate product of N-[3(dimethylamino)-propyl]-perfluorinated sulfonamide :  A ce rt ai n volume of N,N-di me thyl -1,3propanediamine was measured and dissolved in certain volume of isopropyl ether; the mixtures were poured into a three-neck flask surrounded by the ice-water bath at the temperature of 10 ºC.  A certain volume of perfluorooctane sulfonyl fluoride was measured and dissolved in a proper volume of isopropyl ether; the mixtures were poured slowly into a three-neck flask at the temperature of 10 ºC.  The mixtures were dropped by the dropping funnel. The temperature was adjusted to 60 ºC and the mixtures were poured into beakers open for one day after reacting for about 6 h.  The suction filtration was operated with absolute 173

J. Indian Chem. Soc., Vol. 94, February 2017 ethyl alcohol and the absolute ethyl alcohol was removed by heating and drying.  The product was obtained and named as N-[3(dimethylamino)-propyl]-perfluorinated sulfonamide (NFA). The chemical equation is as follows :

 The reactants were cooled to 50 ºC and a certain amount of NaHSO3 was added. Heating reaction was made for 6 h at the temperature of 85 ºC.  The reactants were poured into the beaker and the liquid was dried and evaporated, which was extracted by using with the acetone. The product was obtained and named as the sulfobetaine-type fluorocarbon surfactant (FS). The chemical equation is as follows :

(2) The synthetic of intermediate product of 2-hydroxy3-chloropropyl sulfonate :  A certain quality of NaHSO3 was poured into appropriate solvents (The solvents were mixed by methanol and water, and the ratio of methanol to water = 3 : 7).  NaHSO3 was fully dissolved into the solvents with stirring at the temperature of 70 ºC.  Epoxy chloropropane was added and the temperature was adjusted to 85 ºC for reacting for about 3 h. And then the product was cooled crystallization and extracted by the solvents (methanol : water = 3 : 7).  The product was obtained and named as 2-hydroxy3-chloropropyl sulfonate. The chemical equation is as follows :

Oil displacement experiment of binary foam-complex flooding system : Materials and conditions : (1) Dewatered crude oil (its viscosity is 920 mPa·s at 50 ºC and 2060 mPa·s at room temperature, respectively) was from Daqing oil field, China. (2) Water was distilled water. (3) Binary foam-complex flooding system was composed by FS (0.2 wt%) +1000 mg/L HPAM (molecular weight 10 million). (4) Experimental gas was high-pressure N2 (nitrogen).

(3) Synthetic of the sulfobetaine-type fluorocarbon surfactant :

(5) The property parameters of the sand-pack tube are as follows : radius is 3.0 cm, length is 60 cm, permeability is 370.6×10–3 um2 and porosity is 24.5%.

 The intermediate product of N-[3-(dimethylamino)propyl]-perfluorinated sulfonamide (NFA) was dissolved into appropriate isopropanol.

(6) The experimental pressure and temperature were 0.1 MPa and 50 ºC, respectively.

 The mixture was poured into a three-neck flask and dissolved by heating at the temperature of 60 ºC.  A certain volume of 2-hydroxy-3-chloropropyl sulfonate was dissolved into distilled water and poured into the same three-neck flask to heat and to condensate reflux for 6 h at the temperature of 85 ºC. 174

Experimental device : The key instruments are composed of HT- automatic mixing device, thermostat water bath, analytical balance and oven. Fig. 2 shows a schematic drawing of the foam complex flooding experimental device38. Experimental procedures : The test procedures were described as follows. (1) The formation sand was filled into the sand-pack

Liu et al. : Synthesis and oil displacement experiment on sulfobetaine-type fluorocarbon surfactant system

(I) oil

(II)

water

(III)

flooding system

(1) Water-storage tank; (2) Booster pump; (3) Pressure-test equipment; (4) Core holder; (5) Collector; (6) Thermostat; (7) Back-pressure value Fig. 2. The device of oil displacement experiment.

tube and the sand-pack tube was weighed. (2) The distilled water was injected at speed of 2 ml/ min in order to make the sand-pack tube saturating the water for 4 h. Meanwhile, the permeability was calculated by measuring the pressure across sand-pack tube. The sand-pack tube was weighed and the porosity was calculated. (3) The saturated-water core was displaced by crude oil at speed of 1 ml/min until there was no water to run; the irreducible water saturation was measured. (4) Then the core was aged for 24 h at the temperature of 45 ºC. (5) The water flooding experiment was conducted at speed of 0.2 ml/min until the water cut was up to 98% and the oil recovery was calculated. (6) A certain PV (pore volume) numbers of flooding system (0.3 PV) and nitrogen (0.3 PV) were injected in alternating slugs at a speed of 0.2 ml/min and followed by water flooding until the water cut was up to 98%. Then, the enhanced oil recovery was calculated by the flooding system. Numerical simulation of binary foam-complex flooding system : The numerical simulation was performed by injecting the binary foam-complex flooding system in sand-packed tube. CMG-STARS simulator is a compositional reservoir simulator developed by Computer Modeling Group (Canada) which is very useful to model the chemical flooding processes. In this work, a lab procedure is described to build a predictive reservoir model using CMG-STARS

Fig. 3. The grid blocks arranged of 1D core model for the binary foam-complex flooding.

to assist the binary foam-complex flooding system. Fig. 3 shows the grid blocks arranged of 1D core model for the binary foam-complex flooding displacement39. Some of these assumptions such as well spacing, simulation conditions and other simulation parameters were based on the sand-packed tube as follows. (1) A basic numerical simulation model was developed first and used in the water flooding. Changes were then made to this model and used in modeling alternating injection FS/HPAM + N2 flooding after the water flooding. Then following water flooding were carried out. (2) The fluid data was described with 3 phases and 5 chemical components : water, FS and polymer (HPAM) defined in the aqueous phase, dead oil defined in the oleic phase, and N2 defined in the gaseous phase. (3) The sand-packed tube model (60×1×1 grids) (length : 30 cm; diameter : 3.84 cm) was designed to match the sand-packed tube caused by binary foam-complex flooding system. (4) A 2-spot well spacing was used with one producer and one injector placed on opposite of the core. The injector and the producer were placed in the grid (1, 1, 1) and (60, 1, 1), respectively. Both wells were penetrated in the grid blocks in vertical (Z) direction. (5) The sand-packed tube was homogeneous, horizontal and equal thickness. (6) The inner boundary condition of the injector had constant injecting rate and the outer boundary condition of the producer had constant bottomhole flow pressure (0.1 Mpa). The initial condition had the constant pressure (0.1 Mpa) according to the experimental core flooding tests condition. 175

J. Indian Chem. Soc., Vol. 94, February 2017 (7) The PVT analysis, the formation volume factor, the fluid compressibility, the relative permeability for oil-water systems (intermediate wettability rocks) and other relative parameters referred to the actual data in Daqing Oilfield, China. (8) When the water cut (fw) of the production liquid went to 98%, the simulator was terminated just like core flooding tests becoming stable as steady state conditions.

0.05, 0.1, 0.2, 0.3 and 0.4 wt% of FS, respectively. After FS was poured into 1000 ml-cylinder, the different foaming volumes (ml) were respectively recorded at 0, 3, 5, 30 min with Ross-Miles method in order to evaluate the foaming properties and stabling foam properties. Fig. 5 shows the effect of FS concentration on the foam properties.

Results and discussion Analysis of infrared spectroscopy : The IR (infrared) spectroscopy of FS is shown in Fig. 4.

Fig. 5. Effect of FS concentration on the foam properties.

From Fig. 5, the foaming properties of the FS were much poorer at lower concentrations. It could produce a relative larger foam volume at the concentration of 0.2 wt%. The foaming volume of FS also increased with Fig. 4. IR spectrum of FS.

There were the symmetric stretching vibration bands of the -CF2 near 558 cm–1, asymmetric stretching vibration bands of the -CF2- near 1150 cm–1 and 1240 cm–1, stretching vibration bands of the -SO32– near 1060 cm–1, absorption bands of the C-C near the 1515 cm–1and stretching vibration absorption bands of the -O-H near 3490 cm–1. The IR spectrum result shows that the reactions occurred between the 2-hydroxy-3-chloropropyl sulfonate and the intermediate product of NFA. As a result, the sulfonic root was introduced.

the increase of the concentration which illustrated that it had the good foaming properties. The foam life of the foaming agent increased with the increase of the concentration and the foaming volume kept for a long time. When the foaming volume was up to a certain value, it maintained the stability for a long period of time which explained the foam stability was better. When the concentration exceeded 0.2%, the foaming properties and the foam stability properties could not increase by a large margin with the increase of the concentration, which illustrated that the molecule of FS in the solution surface was close to saturation state and the surface activity was close to the maximum. As indicated by the tests, FS has

Foam performance :

the optimal foaming and foam stability at the mass frac-

The different concentrations were prepared with 0.01,

tion of 0.2 wt%.

176

Liu et al. : Synthesis and oil displacement experiment on sulfobetaine-type fluorocarbon surfactant system Effect of oil displacement : Results of oil displacement experiment : HPAM is a very common flooding oil polymer. It is used extensively in the oil field. By the binary surfactantpolymer complex flooding, the polymer can change the mobility ratio, thicken the viscosity, reduce the injected rate of the surfactant and its consumption, and increase the stability of oil-in-water emulsion, which will result in largely increasing the sweep efficiency and washing oil capacity. Based on earlier optimized results, the experimental injected binary foam-complex flooding system was replicated by FS (0.2 wt%) +1000 mg/L HPAM (molecular weight 10 million) + N2 (frother agent), which has the maximum foaming volume and exhibits a relatively better performance in oil displacement.

Fig. 6. The relationship between the oil recovery and injection volume.

The oil displacement FS/HPAM system (0.35 PV) and nitrogen (0.35 PV) were injected in alternating slugs. Table 1 lists the comparative results by the binary foamcomplex flooding system and water flooding. From Table 1, the oil recovery was only 44.53% by water flooding. While, it was increased by 32.06% after FS/HPAM system (0.35 PV) and nitrogen (0.35 PV) were injected in alternating slugs. The ultimate oil recovery was up to 76.58%. Table 1. Comparative results of oil displacement experiment in sand-pack tube Water

Complex

flooding

Binary foam-complex flooding system

effects EOR

EOR

FS/HPAM

N2

EOR

(%)

(PV)

(PV)

(%)

(%)

44.53

0.35

0.35

32.06

76.58

The black dots of Fig. 6 and Fig. 7 represent respectively the relationships between the oil recovery and injection pressure gradient with different injection volume numbers. From Fig. 6, the water flooding oil recovery was only 44.53%. The oil recovery increased to 76.58% and the complex recovery increased by 32.06% after injecting the slug of 0.35 PV flooding system and 0.35 PV N2. From the different oil recovery curves, we can see the

Fig. 7. The relationship between injection pressure gradient and injection volume.

complex recovery has obvious rising trend in the basic of the water flooding. There is a non-smooth wave during the rising. This is because there are different flooding systems with different flooding mechanisms. The complex oil recovery curve has obvious advancement at the switched injection point over the water flooding. From Fig. 7, when the sand-filled pipe saturated oil was conducted by water flooding, the injection-production pressure difference immediately decreased. As a result, the residual oil was hardly moved by water. After the system was switched to inject the slug of the binary foam-complex flooding system and N2, the injection-production pressure difference immediately increased and recovered to the original pressure difference to make the residual oil to flow. When the binary foam-complex flood177

J. Indian Chem. Soc., Vol. 94, February 2017 ing finished and was switched the conventional water flooding, the injection-production pressure difference decreased again. The further conventional water flooding had the residual pressure difference, which can continue to flood the residual oil in the sand-filled pipe. Results of numerical simulation : The solid lines of Fig. 6 and Fig. 7 represent respectively the relationships between the oil recovery and injection pressure gradient with different injection volume numbers by numerical simulation methods. From Fig. 6 and Fig. 7, the comparison shows that there is a better agreement between the experimental flooding tests data and the simulation data. Different flooding systems have the different flooding mechanisms. The good synergistic effect, which resulted from the electrostatic force and hydrogen-bond action as well as the ion-dipole interaction between the surfactant polar head and the polymer polar part between the HPAM (strong hydrolysis) and amphoteric fluorocarbon surfactant, can remarkably enhance oil recovery. Meanwhile, FS/HPAM system can form the stabile foam after N2 injection. On the one hand, HPAM can improve the mobility ratio, thicken the flooding system, reduce the spread and consumption of the surfactant, and thereby increase the sweep volume. On the other hand, FS can emulsify crude oil, increase the viscosity of flooding system, decrease the surface tension between the polymers and crude oil, and thereby increase the washing oil efficiency21,22. FS and its binary foam-complex flooding system have great potential prospect in the tertiary oil recovery in oil fields. Conclusions Based on the present work, the following conclusions can be drawn : (1) The sulfobetaine-type fluorocarbon surfactant (FS) was synthesized in the laboratory by reaction of NFA with 2-hydroxy-3-chloropropyl sodium in an alkaline environment. (2) As indicated by the tests, FS has the optimal foaming and foam stability at the concentration of 0.2 178

wt%. (3) The oil displacement experiments and numerical simulation methods were conducted with the binary foam-complex flooding system including FS (0.2 wt%), HPAM (1000 mg/L) and N2 in alternating slugs injected, which could enhance oil recovery by 32.06% over the water flooding, and the ultimate oil recovery is up to 76.58%. (4) HPAM can improve the mobility ratio, thicken the viscosity, and increase the sweep volume. FS can emulsify crude oil and increase the viscosity of the flooding system, which in turn increases the washing oil efficiency. (5) The binary foam-complex flooding system could greatly enhance oil recovery after water flooding. Results have shown that FS and its binary foam-complex flooding system have great prospect in EOR processes in the future. Acknowledgement This research is financially supported by the National Oil & Gas Key Special Project of China for 2016ZX05015002 and 2016ZX05016-006 the contribution of which and the permission for publication are gratefully acknowledged. The authors would like to thank the State Key Laboratory of Enhanced Oil Recovery Research, Institute of Exploration and Development (CNPC). The authors would also like to thank Professor Y. L. Wang, Petroleum University of China (Qing Dao) for her advice on this research and grammar correction and clarity. References 1.

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