Synthesis of Solvents for Water Desalination: Amines and Ethers.

Host-guest complexation. 8. Macrocyclic polyethers shaped by two rigid substituted dinaphthyl or ditetralyl units

“…Caled for C25H23O3N: C, 77.90; , 6.01. Found: C,77.84;H,5.99. 3,3'-Bis(dimethylaminomethyl)-2,2'-dihydroxy-l,l'-dinaphthyl (6). Application of the same procedure to 42.9 g (0.15 mol) of 2,2'-dihydroxy-t,l'-dinaphthyl and 131 g (1 mol) of dimethylami-noisobutoxymethane7 in 400 mL of isobutyl alcohol gave after 9 days at 160 °C 19.8 g (33%) of diamine 6, mp 256-258 °C, M+ 400.…”

“…The mixture was filtered, the acetic acid was evaporated under reduced pressure, and the residue was distributed between CH2C12 and aqueous NaCH03. The organic layer was washed with water, dried, and evaporated under vacuum to give after drying under vacuum 10 g (98%) of (+)-(S)-25 as a white glass: XH NMR (CDClg) b 1.67 (m, CCH2CH2C), 2.20 (m, ArCH2,4 H), 2.27 (s, ArCH3, 6 ), 2.70 (m, ArCH2,4 H), 3.93 (m, OCH2,16 H), 6.85 (s, ArH, 2 H); Similarly 17.0 g of (-)-(fi)-19 (see above) was reduced to give 20.0 g (98%) of (-)-(fi)-25: [a]25589 -24.0°(c 1.0, CHC13); NMR (CDClg)…”

“…Anal. Caled for C22HuBr402: C. 41.94: H, 2.24 Found: C. 41.69; H, 2.47. (E,R),(S,S) 3,4,14,15,16di( 1,6,9,12,17,4,13,tetraene [<«,«),(S.Sl-29], (R,S),(S,R)-29, (-)-(fi,S)-29, ( + )-(R.R1-29, and (-)-(S,S)-29. To a solution of 0.570 g of 3 in 15 mL of dry DMF stirred at 25 °C under N2 was added 0.22 gof NaH (57% dispersion in mineral oil), followed by 1.6 g of two-armed dimethyl ditosvlate.…”

“…Procedure II. A mixture of 100 mL of THF, 1.0 g of optically pure binaphthol, (-)-(S)-3 (0.0032 mol, [a]25589 -34.3°, c 1.0, CHCI3), and 0.40 g (0.0064 mol) of KOH (85%) was stirred for 1 h and then 2.54 g (0.0032 mol) of optically pure (+)-(S)-20 (dimethyl two-armed ditosylate, [a]25578 + 70.0°, c 1.0, CHCI3) in 100 mL of THF was added; the mixture was refluxed under N2 for 175 h. The crude product (2.62 g) was isolated as before and purified by gel permeation chromatography to give 1.50 g (64%) of (-)-(S,S)-29 as a white foam; M+ 740, M2+ 370, gel permeation retention volume 152 mL of CH2C12; [ ]25436 -380°, [«]2S546 -171°, [a]25578 -152°(c 1.0, CHC13); NMR (CDC13) 7.80-6.90 (m. ArH, 22 H), 4.2-2.85 (m, CHA), 16 H), 2.35 (R,IZ),(S,S) 3,4,6,9,12,17,4,13,IZ),<S,S)-30], (R,S),(S,R)-30, and ( + )-(R,R)~30. A solution of 23 g of tetrol 9 in 2 L of THF, 5.4 g of NaOH in 60 mL of H20, and 56 g of 2,2'-di(5-tosyloxy-3-oxa-l-pentyloxy)--l,l'-dinaphthyl (21)4 was stirred under N2 at reflux for 100 h. The crude product was isolated as in procedure I and chromatographed on 1.5 kg of alumina.…”

Solvo-Surfactant Properties of Dialkyl Glycerol Ethers: Application as Eco-Friendly Extractants of Plant Material through a Novel Hydrotropic Cloud Point Extraction (HCPE) Process

“…Some nonionic hydrotropes with low boiling points may be referred to as solvo-surfactants, emphasizing their solubilizing properties and volatility. As part of our ongoing efforts to develop biosourced hydrotropes, − we focused on short chain dialkyl glycerol ethers, a neglected class of compounds in the literature (Table ), especially with regard to their physicochemical properties , and to their expected low toxicity . Actually, they should exhibit higher hydrophilicity than trialkyl glycerol ethers, which behave as ordinary solvents, but also stronger lipophilicity than monoalkyl glycerol ethers, that should confer improved solubilizing power upon them.…”