* 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.
General procedure: Equimolar amounts of quaternary ammonium salt (1.5 mmol) and p-toluenesulfonic acid monohydrate (Sigma-Aldrich, 98,5+percent used as received) were mixed in a screw-capped 3 ml vial. The mixture was magnetically stirred and heated to 60 °C until a clear colourless liquid was obtained (about 10 min). DES was used right after its preparation. Equimolar amounts (4.5 mmol) of acid and alcohol were added, and the resulting mixture, was heated to 60 °C (or 80 °C if specified) and magnetically stirred for the specified amount of time. Initially the reaction mixture is homogeneous and fluid, and then a heterogeneous system formed as reaction proceeded, due to insolubility of the esters produced in the DES. For the g.c. analysis further elaboration was as follows. At the end of the reaction, tbutylbenzene was added, as the internal standard, to the mixture, which was then extracted with diethyl ether. Organic layer was washed with NaHCO3, dried over Na2SO4 and analyzed by g.c.
Reference：
[1] Chemistry Letters, 1997, # 1, p. 55 - 56
[2] Chemical and Pharmaceutical Bulletin, 2009, vol. 57, # 7, p. 680 - 684
[3] Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 5, p. 607 - 612
[4] Medicinal Chemistry Research, 2011, vol. 20, # 6, p. 769 - 781
[5] Organic Preparations and Procedures International, 2005, vol. 37, # 1, p. 87 - 92
[6] Patent: US6350896, 2002, B1, . Location in patent: Example 6
[7] Agricultural and Biological Chemistry, 1987, vol. 51, # 8, p. 2153 - 2160
[8] Journal of Organic Chemistry, 1959, vol. 24, p. 160,164
[9] Synthetic Communications, 1979, vol. 9, p. 539 - 543
[10] Tetrahedron Letters, 2012, vol. 53, # 38, p. 5151 - 5155
2
[ 143-07-7 ]
[ 111-42-2 ]
[ 120-40-1 ]
Yield
Reaction Conditions
Operation in experiment
97%
at 50 - 190℃; Microwave irradiation
At 50° C., 2.5 g of diethanolamine were admixed slowly with 4.6 g of molten lauric acid with stirring. After the exothermicity had abated, the ammonium salt thus obtained was exposed to microwave irradiation of 200 W in a closed cuvette with maximum cooling performance for 10 minutes. A temperature of 190° C. measured by means of an IR sensor was attained, and the pressure rose to 10 bar.The crude product contained 78percent lauric acid diethanolamide as the main component, 4.5percent water and unconverted reactants. After the reaction mixture had been dried over MgSO4 and irradiated with 200 W microwaves for another five minutes, and water of reaction and excess diethanolamine had been removed by distillation under reduced pressure, a yield of lauric acid diethanolamide of more than 97percent was obtained. The resulting coconut fatty acid diethanolamide contained about 1 molpercent of amino ester and ester amide. The Hazen color number was 120 (undiluted molten product).
Reference：
[1] Patent: US2010/10244, 2010, A1, . Location in patent: Page/Page column 6
[2] Journal of agricultural and food chemistry, 2001, vol. 49, # 12, p. 5761 - 5764
[3] Journal of agricultural and food chemistry, 2001, vol. 49, # 12, p. 5761 - 5764
[4] Organic and Biomolecular Chemistry, 2013, vol. 11, # 7, p. 1242 - 1250
3
[ 143-07-7 ]
[ 120-40-1 ]
Reference：
[1] Patent: CN106167506, 2016, A,
4
[ 143-07-7 ]
[ 56-87-1 ]
[ 59409-41-5 ]
[ 52315-75-0 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2006, vol. 54, # 1, p. 72 - 78
With acidic cation exchange resin Amberlyst 70; at 50 - 145℃;Flow reactor; Green chemistry;
General procedure: Acetic acid and ethanol at a weight ratio of 1:2 or 1:3 were mixed at 30° C., and then introduced into the lower part of the vertical reactor at a liquid hourly space velocity (LHSV) of 3 hour?1. The reaction was performed at 115° C. The esterized mixture was output from the upper part of the vertical reactor, and collected to be analyzed by gas photography. The acid value of the product was determined by titration, and the conversion rate and the selectivity were analyzed. The results were shown in Table 1.
1-dimethylamino-2,3-bis-dodecanoyloxypropane[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
l g of N,N-dimethylamino-l ,2-propanediol (8.3 mmoles) and 2.2 molar equivalent of alkyl acid chain were dissolved in methylene chloride while stirring at room temperature. Then, 0.1 g DMAP and 2.2 molar equivalent of DCC were added and the solution was stirred for 3-4 hours or until complete by TLC. Additional small portions of DCC were added if necessary to drive the reaction to completion. The solution was then filtered to remove the precipitated DCU and washed 2X with 1M HCl. The organic layer was collected and dried with sodium sulfate and solvent was removed by rotary evaporation. The di-substituted dimethylaminoglycerol product (1) was moved forward with no further purification.
With sodium hydroxide; triethylamine; In water; 1,2-dichloro-ethane; acetone;
EXAMPLE 1 Lauric acid 20 g was dissolved in 80 ml 1.2-dichloroethane and then 10 g triethylamine was added. The resulting solution was held at -2 - 5C and 8 g sulfuric anhydride was added dropwise with stirring. The reaction mixture was stirred at that temperature for 50 minutes and a solution of lauric acid-sulfuric acid mixed acid anhydride was prepared and employed in the following acylation. Sodium hydroxide 8 g was added to a suspension of 14.7 g L-glutamic acid in 72 ml water and 48 ml acetone. The resulting solution of disodium L-glutamate was cooled to 0C and 10 ml of 10 N aqueous sodium hydroxide solution and the mixed acid anhydride prepared in the above was added drop by drop under stirring while the pH was controlled to 12 - 13. This reaction solution was stirred for 1 hour at 0C. Thereafter, the reaction mixture was concentrated under reduced pressure to distill off the solvent. The residue was adjusted to a pH 1 with 6 N sulfuric acid. The crude crystals of N-lauroyl-L-glutamic acid precipitated, and were filtered and dried (25.7 g). They were washed with petroleum benzine and 23.2 g of the purified acid were recovered by filtration (70.3% yield) M.P. 102 - 105C. After recrystallization from ethanol-petroleum benzine, the elemental analysis was as follows:
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