120-40-1

Usage

Uses

N,N-Bis(2-hydroxyethyl)dodecanamide is used in preparation method of water-absorbent resin for improving anti-caking performance.

General Description

Off-white waxy solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

An alcohol and amide. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Fire Hazard

Flash point data for LAURIC ACID DIETHANOLAMIDE are unavailable, however, LAURIC ACID DIETHANOLAMIDE is probably combustible.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C16H33NO3/c1-4-5-6-7-8-9-10-11-12-13-16(20)17(14(2)18)15(3)19/h14-15,18-19H,4-13H2,1-3H3

Synthetic route

methyl n-dodecanoate (111-82-0) + 2,2'-iminobis[ethanol] (111-42-2) → N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1)

Conditions	Yield
at 110℃; for 1h; Catalytic behavior; Reagent/catalyst;	99%
at 110℃;	99%
With sodium hydroxide at 100℃; for 5h;	85%
With sodium hydroxide at 110℃; for 5h;	84.24%
With Candida antarctica lipase In acetonitrile at 50℃; for 24h;	56.5%

lauric acid (143-07-7) + 2,2'-iminobis[ethanol] (111-42-2) → N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1)

Conditions	Yield
at 50 - 190℃; under 760.051 - 7500.75 Torr; Microwave irradiation;	97%
With Candida antarctica lipase; calcium chloride In acetonitrile at 50℃; for 24h;	76%
With Candida antarctica lipase In acetonitrile at 50℃; for 24h; Kinetics;	49.5%
Stage #1: lauric acid; 2,2'-iminobis[ethanol] With benzotriazol-1-ol; triethylamine In dichloromethane for 0.25h; Cooling with ice; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Cooling with ice;

n-dodecanoyl chloride (112-16-3) + 2,2'-iminobis[ethanol] (111-42-2) → N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1)

Conditions	Yield
In methanol; diethyl ether	88%
With chloroform at 15 - 20℃;
With tert.-butylhydroperoxide; ammonia In dichloromethane at -2℃; pH=9;

lauric anhydride (645-66-9) + 2,2'-iminobis[ethanol] (111-42-2) → N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1)

Conditions	Yield
With Candida antarctica lipase In acetonitrile at 50℃; for 24h;	35.8%

tridodecanoylglycerol (538-24-9) + 2,2'-iminobis[ethanol] (111-42-2) → N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1)

Conditions	Yield
With Candida antarctica lipase In acetonitrile at 50℃; for 24h;	31.1%

2-(2-lauroyloxy-ethylamino)-ethanol (25859-09-0) → N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1)

Conditions	Yield
at 56℃; Geschwindigkeit der Isomerisierung;

ethyl laurate (106-33-2) + 2,2'-iminobis[ethanol] (111-42-2) → N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1)

2,2'-iminobis[ethanol] (111-42-2) → N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1)

Conditions	Yield
Magnesol; sodium methylate In methanol at 70℃; for 1h; Kinetics;

methyl ester of Industrene 325 + 2,2'-iminobis[ethanol] (111-42-2) → N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1)

Conditions	Yield
sodium methylate In methanol at 50 - 70℃; for 6h;

lauric acid (143-07-7) → N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: caprolactam; thionyl chloride / ethanol / -2 °C 2: ammonia; tert.-butylhydroperoxide / dichloromethane / -2 °C / pH 9 View Scheme

1,3-propanesultone (1120-71-4) + N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1) → sodium 3-(2-{N-[2-(3-sulfonatopropoxy)ethyl]dodecanamido}ethoxy)propane-1-sulfonate

Conditions	Yield
With sodium hydroxide at 80℃; for 24h;	88%
With sodium hydroxide In tetrahydrofuran for 16h; Reflux;	54.25%

N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1) + pivaloyl chloride (3282-30-2) → N,n-bis(2-trimethylacetoxyethyl)lauramide (63056-92-8)

N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1) + benzoyl chloride (98-88-4) → N,n-bis(2-benzoyloxyethyl)lauramide (63056-90-6)

Conditions	Yield
With pyridine In benzene

oxirane (75-21-8) + N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1) → lauryl monoglycerin ester10EO

Conditions	Yield
Stage #1: N,N-bis-(2-hydroxy-ethyl)-lauramide; sodium hydroxide at 80 - 90℃; under 15.0015 Torr; for 1h; dehydration; Stage #2: oxirane at 80 - 90℃; for 20h; Product distribution / selectivity;
Stage #1: N,N-bis-(2-hydroxy-ethyl)-lauramide; tetramethyl ammoniumhydroxide In water at 80 - 90℃; under 15.0015 Torr; for 1h; dehydration; Stage #2: oxirane at 80 - 90℃; for 20h; Product distribution / selectivity;

oxirane (75-21-8) + N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1) → lauryl diethanolamide8EO adduct

Conditions	Yield
Stage #1: N,N-bis-(2-hydroxy-ethyl)-lauramide; sodium hydroxide; tetramethyl ammoniumhydroxide In water at 80 - 90℃; under 15.0015 Torr; for 1h; dehydration; Stage #2: oxirane In water at 80 - 90℃; for 3h;

oxirane (75-21-8) + N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1) → lauryl diethanolamide10EO adduct

Conditions	Yield
Stage #1: N,N-bis-(2-hydroxy-ethyl)-lauramide; sodium hydroxide; tetramethyl ammoniumhydroxide In water at 80 - 90℃; under 15.0015 Torr; for 1h; dehydration; Stage #2: oxirane In water at 80 - 90℃; for 3h; Product distribution / selectivity;
Stage #1: N,N-bis-(2-hydroxy-ethyl)-lauramide; sodium hydroxide at 80 - 90℃; under 15.0015 Torr; for 1h; dehydration; Stage #2: oxirane at 80 - 90℃; for 3h; Product distribution / selectivity;

N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1) + epichlorohydrin (106-89-8) → C22H41NO5 (212916-06-8)

Conditions	Yield
With tetrabutyl-ammonium chloride; sodium hydroxide In water at 0 - 20℃; for 12.5h;

N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1) + molybdenum(VI) oxide + methyl salicylate (119-36-8) → 2C16H31NO3(2-)*2C8H7O3(1-)*Mo(6+)

Conditions	Yield
In water at 95℃; for 1h; Inert atmosphere;

N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1) + 3,5-diisopropylsalicylic acid (2215-21-6) + molybdenum(VI) oxide → 2C16H31NO3(2-)*2C13H17O3(1-)*Mo(6+)

Conditions	Yield
In water at 95℃; for 1h; Inert atmosphere;

N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1) + salicylic acid (69-72-7) + molybdenum(VI) oxide → 2C16H31NO3(2-)*Mo(6+)*2C7H5O3(1-)

Conditions	Yield
Stage #1: salicylic acid; molybdenum(VI) oxide In water at 95℃; for 0.5h; Inert atmosphere; Stage #2: N,N-bis-(2-hydroxy-ethyl)-lauramide In water at 95℃; for 1h; Inert atmosphere;

N-lauroyl-N-methyl-beta-alanine + N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1) → lauric acid diethanolamide-O,O'-bis(N-lauroyl-N-methyl-β-alanine)ester

Conditions	Yield
at 120℃; under 15.0015 Torr; for 7h;	822 g

N-lauroyl-N-methyl-beta-alanine + N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1) + N-acyl sarcosinate (97-78-9) → lauric acid diethanolamide-O-(N-lauroyl-N-methyl-beta-alanine)-O'-(N-lauroyl-N-methyl-glycine)ester

Conditions	Yield
at 120℃; under 15.0015 Torr; for 7h;	807 g

N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1) + N-acyl sarcosinate (97-78-9) → lauric acid diethanolamide-O,O'-bis(N-lauroyl-N-methyl-glycine)ester

Conditions	Yield
at 120℃; under 15.0015 Torr; for 7h;	793 g
at 130℃; under 15.0015 Torr; for 10h;	68.54 g
at 130℃; under 15.0015 Torr; for 10h;	68.54 g
at 130℃; under 15.0015 Torr; for 10h;	68.54 g
at 130℃; under 15.0015 Torr; for 10h;	68.54 g

N,N-bis-(2-hydroxy-ethyl)-lauramide (120-40-1) + molybdenum(VI) oxide → C16H31MoNO5

Conditions	Yield
In toluene at 105℃; Inert atmosphere;

Upstream product

• 112-16-3 n-dodecanoyl chloride 
• 111-42-2 2,2'-iminobis[ethanol] 
• 106-33-2 ethyl laurate 
• 143-07-7 lauric acid 
• 645-66-9 lauric anhydride 
• 111-82-0 methyl n-dodecanoate 
• 538-24-9 tridodecanoylglycerol 
• 25859-09-0 2-(2-lauroyloxy-ethylamino)-ethanol 

Downstream Products

• 63056-90-6 N,n-bis(2-benzoyloxyethyl)lauramide 
• 63056-92-8 N,n-bis(2-trimethylacetoxyethyl)lauramide 
• 143-07-7 lauric acid 
• 111-42-2 2,2'-iminobis[ethanol] 
• 25859-09-0 2-(2-lauroyloxy-ethylamino)-ethanol 
• 2512-14-3 N,N-Bis-(2-lauroyloxyethyl)-lauramid 

Relevant academic research and scientific papers

One step synthesis of fatty acid diethanolamides and methyl esters from triglycerides using sodium doped calcium hydroxide as a nanocrystalline heterogeneous catalyst

Here, we report the preparation of a series of Na+-doped Ca(OH)2 in nanocrystalline form using a very simple method, and investigation of their catalytic activities towards one step aminolysis and transesterification of used cottonseed oil. The catalyst prepared by doping 3.5 wt% Na in Ca(OH)2 was found to exist in nanocrystalline form (particle size = 25-30 nm) as suggested by TEM and DLS studies and found to have the basic strength of 15.0 2 was used as a solid catalyst towards the aminolysis and transesterification of used cotton seed oil with diethanolamine and methanol, respectively. The catalyst was found to complete the aminolysis and transesterification of a variety of feedstocks even at room temperature and shows excellent reusability.

Investigation on interfacial/surface properties of bio-based surfactant N-aliphatic amide-N,N-diethoxypropylsulfonate sodium as an oil displacement agent regenerated from waste cooking oil

To regenerate the non-edible waste cooking oil and significantly reduce the negative effect on human being and the environment, a bio-based nonionic-anionic amphoteric sulfonate type surfactant with excellent interfacial and surface properties was synthesized. The interfacial tensions between crude oil and water can reach up to an ultralow value as 0.0040?mN·m??1 without additives. With dynamic light scattering and surface tension, micelles formed by N-aliphatic amide-N,N-diethoxypropylsulfonate bio-based surfactant were studied. This work also systematically investigated the surface activity, adsorption behavior, and thermodynamic parameters (ΔGm0, ΔGads0, ΔHm0, ΔSm0, ΔHmA, ΔCp,m0) of micellization. According to the experimental results, it can be seen that the bio-based surfactant has an excellent surface activity, besides, the micelle formation is entropy and enthalpy co-driven at 25–45?°C. Dynamic light scattering also illustrated the micelle formation. Through this research work, we expect to gain some insights into the phase behaviors of this bio-based surfactant and broaden its great potential oilfield application in enhanced oil recovery.

Oil soluble molybdenum amine complex and preparation method thereof

The invention discloses an oil soluble molybdenum amine complex and a preparation method of the oil soluble molybdenum amine complex. The method adopts long-chain saturated fatty acid as the starting material, acylchlorination reaction is carried out on the long-chain saturated fatty acid and thionyl chloride to obtain 1-chloro saturated fatty acid, then amidation reaction is carried out on the 1-chloro saturated fatty acid and diethanol amine to obtain saturated fatty acid amide, and finally complexation is carried out on the saturated fatty acid amide and a molybdenum trioxide solution so as to obtain the oil soluble molybdenum amine complex. The prepared molybdenum amine complex has good oil solubility, solves the poor oil solubility, corrosion resistance, wear resistance and friction reduction and other problems difficult to overcome in existing products, at the same time significantly reduces the adding amount of high sulfur and phosphorus components, and has enormous boosting effect on organic molybdenum series lubricating products currently under research in China, thus promoting nationalization of high-end lubricating oil and efficient utilization and high added value of molybdenum resources.

Solvent-free one step aminolysis and alcoholysis of low-quality triglycerides using sodium modified CaO nanoparticles as a solid catalyst

Here, we report the solvent-free one step preparation of fatty acid amides and fatty acid alkyl esters from low quality triglycerides using a solid catalyst. A series of Na+ modified CaO has been prepared in the form of nanoparticles by a modified incipient-wetness impregnation method, and used as a solid catalyst for aminolysis and alcoholysis of triglycerides. The prepared catalyst 3-NaC/CaO-450 (3 wt% Na impregnated in CaO) was found to exist in nanoparticle form (particle size = 25 nm) as suggested by TEM, DLS and powder XRD studies, have a surface area of 10.9 m2 g-1 (BET method) and found to have the basic strength of 15.0 H- 18.4 as supported by the Hammett indicator test. The catalyst was found to complete the aminolysis (5 wt% catalyst; 6:1 molar ratio of diethanolamine/oil; 110 °C) with excellent recyclability and is also equally efficient for the alcoholysis (5 wt% catalyst; 12:1 molar ratio of methanol/oil; 65 °C) of used cotton seed oil.

Sulfonate type biomass surface active agent and synthetic method

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Low molecular weight PEI-based biodegradable lipopolymers as gene delivery vectors

Non-viral gene vectors play an important role in the development of gene therapy. In this report, different hydrophobic chains were introduced into low molecular weight (LMW) PEI-based biodegradable oligomers to form a series of lipopolymers (LPs), and their structure-activity relationships were studied. Results revealed that the nine polymers can condense plasmid DNA well to form nanoparticles with appropriate sizes (120-250 nm) and positive zeta-potentials (+25-40 V). In vitro experiments were carried out and it was found that LP2 showed much higher transfection efficiency both in the presence and in the absence of serum under the polymer/DNA weight ratio of 0.8 in A549 cells.

Method For Producing Fatty Acid Alkanol Amides

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Lipase-catalyzed synthesis of fatty acid diethanolamides.

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