* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
A mixture of a 38percent aqueous solution of dimethylamine (12.5 mL, 93.8 mmol) and dodecyl bromide (11.7 g, 46.9 mmol) in benzene (15 mL) was stirred at 20—25 °C for 20 h. Then, a 50percent aqueous solution of NaOH (1.9 g, 46.9 mmol) was added to the reaction mixture, and the resulting mixture was evaporated in vacuo. The residue was dissolved in CHCl3 (20 mL), the formed precipitate was filtered off, and the filtrate was evaporated in vacuo. According to the 1H NMR spectral data, the isolated mixture contained amine 6a (4.1 g, 40percent), N,N-didodecyl-N,N-dimethylammonium bromide (4.9 g, 46percent), and unreacted dodecyl bromide (1.7 g, 14percent).
Reference:
[1] Russian Chemical Bulletin, 2014, vol. 63, # 11, p. 2445 - 2454[2] Izv. Akad. Nauk, Ser. Khim., 2014, # 11, p. 2445 - 2454
2
[ 112-18-5 ]
[ 143-15-7 ]
[ 3282-73-3 ]
Reference:
[1] Chemical Communications, 2006, # 44, p. 4575 - 4577
[2] Journal of Organic Chemistry, 1984, vol. 49, # 20, p. 3774 - 3778
[3] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1987, p. 541 - 546
[4] Journal of Physical Chemistry, 1983, vol. 87, # 4, p. 538 - 540
[5] Bulletin of the Chemical Society of Japan, 2003, vol. 76, # 10, p. 1903 - 1910
[6] Patent: WO2005/97729, 2005, A2, . Location in patent: Page/Page column 49-50; 56-57
3
[ 4536-30-5 ]
[ 3282-73-3 ]
Reference:
[1] Russian Chemical Bulletin, 2014, vol. 63, # 11, p. 2445 - 2454[2] Izv. Akad. Nauk, Ser. Khim., 2014, # 11, p. 2445 - 2454
4
[ 74-83-9 ]
[ 2915-90-4 ]
[ 3282-73-3 ]
Reference:
[1] Molecular Crystals and Liquid Crystals (1969-1991), 1987, vol. 146, p. 121 - 136
5
[ 23381-53-5 ]
[ 3282-73-3 ]
Reference:
[1] Journal of Physical Chemistry, 1987, vol. 91, # 3, p. 674 - 685
In methanol; at 65 - 142℃;Conversion of starting material;
A 1-liter, creased, 4-necked round bottom Pyrex flask equipped with mechanical stirrer, 250-milliliter (ml) addition funnel, temperature probe, heating mantle, and water-cooled total reflux condenser was used. The flask was initially charged with 200 grams (1.08 mole) of ADMA-10 (decyldimethylamine, available from Albemarle Corporation, Baton Rouge, LA), and 239 grams (1.08 mole) decyl bromide was placed in the addition funnel. The stirrer was turned on and the reactor was heated to 65C. The decyl bromide was added dropwise to the ADMA-10 as the temperature of the reactor was allowed to rise from 65C to 142C. The addition funnel was then charged with 110 grams of methanol, and the methanol was added dropwise to the solution as the temperature of the reactor was allowed to fall to 90C. After the entire volume of the methanol was added to the reaction mixture, the heat and stirring were ceased and the intermediate quaternary ammonium (quat-Br) solution was allowed to cool.
EXAMPLE 10 Finsolv 116/Didodecyldimethylammonium bromide Microcapsules Microcapsules were prepared as in Example 1, except using the following materials and reaction conditions: Didodecyldimethylammonium bromide 75 grams Finsolv 116 150 grams Pre-mixing temperature 76 C. Reactor temperature 52 C. FC-77 fluid 800 ml/Cab-O-Sil TS-720 1.5 grams at 11 C.
hydroxygallium naphthalocyaninetetrasulfonic acid[ No CAS ]
[ 3282-73-3 ]
4C26H56N(1+)*C48H21GaN8O13S4(4-)[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
39%
In water; for 0.08333330000000001h;Product distribution / selectivity;
A mixture of hydroxygallium(III) naphthalocyaninetetrasulfonic acid 4 (849 mg, 0.758 mmol) and didodecyldimethylammonium bromide (1.61 g, 3.49 mmol) in water (100 mL) was stirred for 5 min. The reaction mixture was diluted with water (100 mL) and extracted with chloroform/methanol (50:50, 2×200 mL). The combined organic layers were evaporated and the residue was suspended in warm water (200 mL), filtered, and washed with warm water and cold water/acetone (50:50) and dried to give the product 6 as a dark-green powder (777 mg, 39%).
A mixture of tetrakis(tributylammonium) hydroxygallium(III) naphthalocyaninetetrasulfonate (5.74 g, 3.08 mmol) and didodecyldimethylammonium bromide (5.71 g, 0.012 mol) in methanol (200 mL) was evaporated to half volume with heating under a stream of nitrogen and diluted with water (100 mL). The solid was filtered off and washed with hot water (3×250 mL) and hot acetone/water (50:50, 3×250 mL) and allowed to dry. The solid was then washed further with toluene (2×250 mL) and boiling hexane (250 mL) and dried to give the product as a green powder (7.32 g, 90%).1H NMR (d6-DMSO) delta 0.86 (24H, t, J=6.6 Hz); 1.25 (144H, m); 1.62 (16H, m); 3.20 (16H, m); 4.25 (24H, s); 7.9-11.1 (20H, m).1H NMR (d6-DMSO): delta -0.46 (1H, s); 0.83 (24H, t, J=6.6 Hz); 1.25 (144H, m); 1.60 (16H, m); 3.20 (16H, m); 4.25 (24H, s); 7.9-11.1 (20H, m).UV-Vis-NIR (DMSO): lambdamax 790, 704, 342 nm.
A mixture of a 38% aqueous solution of dimethylamine (12.5 mL, 93.8 mmol) and dodecyl bromide (11.7 g, 46.9 mmol) in benzene (15 mL) was stirred at 20-25 C for 20 h. Then, a 50% aqueous solution of NaOH (1.9 g, 46.9 mmol) was added to the reaction mixture, and the resulting mixture was evaporated in vacuo. The residue was dissolved in CHCl3 (20 mL), the formed precipitate was filtered off, and the filtrate was evaporated in vacuo. According to the 1H NMR spectral data, the isolated mixture contained amine 6a (4.1 g, 40%), N,N-didodecyl-N,N-dimethylammonium bromide (4.9 g, 46%), and unreacted dodecyl bromide (1.7 g, 14%).