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Lauric acid is a saturated medium-chain fatty acid with a 12-carbon backbone. Lauric acid is found naturally in various plant and animal fats and oils, and is a major component of coconut oil and palm kernel oil.
Synonyms: Dodecanoic acid;Dodecylic acid;GT-08
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CAS No. : | 143-07-7 |
Formula : | C12H24O2 |
M.W : | 200.32 |
SMILES Code : | CCCCCCCCCCCC(O)=O |
Synonyms : |
Dodecanoic acid;Dodecylic acid;GT-08
|
MDL No. : | MFCD00002736 |
InChI Key : | POULHZVOKOAJMA-UHFFFAOYSA-N |
Pubchem ID : | 3893 |
GHS Pictogram: | ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H318-H410 |
Precautionary Statements: | P273-P280-P305+P351+P338+P310-P501 |
Class: | 9 |
UN#: | 3077 |
Packing Group: | Ⅲ |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With hydroxy-substituted sulfonic acid-functionalized silica (HO-SAS) In tetrahydrofuran at 110℃; Flow reactor | General procedure: Lauric acid (1a) (2.01 g, 10.0 mmol) was dissolved in methanol (10 mL) and then placed in a syringe, which wasthen attached to a syringe pump. The methanol solution was fedinto a stainless steel column (inner volume: 0.53 mL, 4.0 mm i.d. © 50 mm) filled in HO-SAS (334 mg) with a flow rate of0.177 mL.min-1. The column was immersed into an oil bath(110°C). A back-pressure regulator (75 psi) was connected.The reaction mixture was collected from the outlet. The reaction mixture eluted during the first 10 min was discarded. Thereaction mixture was collected during 3 min and added n-decane as an internal standard for GC analysis. The followingportion was collected for a 30 min period in a glass flask, andsolvent was evaporated. The crude mixture was purified byflash column chromatography on SiO2 (hexane/ethyl acetate =5/1) to give 3a (1.13 g, 99percent). |
72 %Chromat. | at 80℃; for 6 h; | 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. |
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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
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. |
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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.28% | 20.44 g of lauric acid (content of 98%) and 20.84 g of N,N'-dicyclohexylcarbodiimide (DCC) (content: 99%) were added to a ball mill and ground for 30 min. Add 14.86 g of glutamic acid (99%) and 8.42 g of sodium bicarbonate. After continuing to grind for 45 min, a white solid product was obtained which was the target collector product. After analysis and testing, The collector product 2-lauroamide glutaric acid content is 52.12%, The yield of 2-lauroyl glutaric acid based on lauric acid was 96.28%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94%; 100% | In toluene; | Example 11 Synthesis of lauroyl chloride To 93 g (0.55 mole) of <strong>[37091-73-9]2-chloro-1,3-dimethylimidazolinium chloride</strong>, 500 g of toluene and 100.2 g (0.5 mole) of lauric acid were added. The mixture was reacted at 110° C. for 4 hours. The reaction mass was analyzed by gas chromatography and liquid chromatography. The conversion ratio of lauric acid was 100percent, and the yield of lauroyl chloride was 100percent. Toluene was distilled from the reaction mass under reduced pressure and successively 56.5 g (0.495 mole) of 1,3-dimethylimidazolidine-2-one was recovered by distillation at 106°-108° C. under reduced pressure of 17 mmHg. Successively, 102.8 g (0.47 mole) of lauroyl chloride was obtained at 142°-144° C. under reduced pressure of 15 mmHg. The yield was 94percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In toluene; | Example 1 Synthesis of Lauroyl Chloride To 9.30 g (0.055 mole) of <strong>[37091-73-9]2-chloro-1,3-dimethylimidazolinium chloride</strong>, 50.1 g of toluene was added and successively 10.02 g (0.05 mole) of lauric acid was added. The mixture was reacted at 110° C. for 4 hours. The reaction mass was analyzed by gas chromatography and liquid chromatography. The conversion ratio of lauric acid was 100percent and the yield of lauroyl chloride was 100percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
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: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8.76 g | With benzotriazol-1-ol; diisopropyl-carbodiimide; In isopropyl alcohol; at 45℃; for 30h;Green chemistry; | 1) Weigh 11.08 g L-arginine ethyl ester hydrochloride,13.63 g lauric acid,17.26 g DIC and 0.7253 g HOBt were dissolved in 247.42 g of isopropanol,The reaction was heated and stirred at 45 C for 30 h.(2) After the reaction is complete, the solvent is removed by rotary evaporation.After washing the by-products, the filtrate is filtered to 240 ml.86.33 g of sodium chloride was added and allowed to stand overnight. The white solid was washed three times with cold water and dried to give 8.76 g of lauryl arginine ethyl ester hydrochloride. The purity was 96.35%. |
Tags: 143-07-7 synthesis path| 143-07-7 SDS| 143-07-7 COA| 143-07-7 purity| 143-07-7 application| 143-07-7 NMR| 143-07-7 COA| 143-07-7 structure
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