Removal of polyethylene glycol mono‐p‐nonylphenyl ether and dodecylbenzenesulfonate by chloromethylated polystyrene–polyethylenepolyamines and –polyethyleneimines

Abstract

SynopsisThe reactions of chloromethylated divinylbenzene crosslinked polystyrene (CMPS) with polyethylenepolyamines (PEPA), polyethyleneimines (PEI), 2-methyl-20xazoline (MeOZO), and the hydrolysis of CMPS-MeOZO reaction products were carried out. The abilities of these products for removing a nonionic surfactant, polyethylene glycol mono-p-nonylphenyl ether (NP, n = lo), solutes in water were investigated. Removal rates of NP by and the amounts of NP removed by CMPS-PEPA, -PEI, -MeOZO, and hydrolyzate of CMPS-MeOZO were compared. The adaptability of removal behavior of the products to the Freundlich's adsorption isotherm and the amounts of NP removed by unit masses of the products were investigated. The products also removed a n anionic surfactant, sodium dodecylbenzene sulfonate (DBS), solutes in water. The mechanisms for removing NP and DBS were discussed. INTRODUCTIONThe author reported previously that polystyrene-polyeoxyethylene block copolymers supported on activated alumina' and the reaction products of chloromethylated divinylbenzene crosslinked polystyrene (CMPS) with polyethylene glycol2 have the ability to remove NP. The author further studied the reaction products of CMPS with polyethylenepolyamines (PE-PAS) and polyethyleneimines (PEIs) as well as the reaction products of CMPS with 2-methyl-2-oxazoline (MeOZO) and their hydrolyzates. These products were found to remove NP and also an anionic surfactant, sodium dodecylbenzenesulfonate (DBS), solutes in water. This study deals with the preparation of these products and the removal behavior of the surfactants in water. EXPERIMENTAL MaterialsCMPS [Polysciences Inc., 200-400 mesh beads, Lot No. 34126, C1 content; 2.63 meq/g (9.32%), divinylbenzene; 2.00 mol %], tetraethylenepentamine (TEP), pentaethylenehexamine (PEH) (Tokyo Kasei Co., technical grade), 2-methyl-2-oxazoline (MeOZO) (Aldrich Co., bp 109.5-110.5"C, 98%), NP, and DBS (Tokyo Kasei Co., extra pure) were commercially obtained. PO- Reactions of CMPS with PEPA and PEIThe reactions were carried out as follows: 2 g of CMPS beads (-CH,Cl groups 0.00526 moll were placed in a three-necked flask of 50 mL. Into this flask were put 10 mL of dioxane; the flask was stoppered and allowed to stand overnight to allow the beads to swell. After 9.5 g of PEH (0.0409 mol) and 10 mL of dioxane were added into the flask, the mixture was stirred for 113 h at 100°C.When the reaction was completed, boiling water was added to the flask and the mixture was stirred for about 10 min at 100°C. The mixture was then filtered using a no. 2 glass filter, the reaction product was washed on the filter with boiling water, 1N HCl, 1N NaOH, and boiling water until excess alkali was removed, and finally with methyl alcohol. Furthermore, the product was extracted with tetrahydrofuran (THF) for 72 h, and dried in U~C U O at 80°C [the yield and the elementary analysis values are shown at the line of CMPS-PEH(2) in Table I]. Reactions of CMPS with MeOZO and Hydrolyses of the Products3Two grams of CMPS and 20 g of MeOZO (0.235 mol) wer...