25727-93-9

Usage

Uses

Used in the Oil and Gas Industry:
4-tetradecylmorpholine is used as a corrosion inhibitor to protect metal surfaces from corrosion. It achieves this by forming a protective film on the surface, thereby extending the life of equipment and reducing maintenance costs.
Used in the Production of Surfactants:
4-tetradecylmorpholine is utilized as an intermediate in the synthesis of surfactants, which are essential in various industries such as cosmetics, pharmaceuticals, and cleaning products due to their ability to reduce surface tension and stabilize emulsions.
Used as a Lubricant Additive:
In the lubricant industry, 4-tetradecylmorpholine is employed as an additive to enhance the performance of lubricants. It contributes to improved lubrication properties, which can lead to reduced friction and wear in mechanical systems.
Safety Considerations:
It is important to handle 4-tetradecylmorpholine with care, as it can cause irritation to the skin and eyes upon contact. Proper safety measures should be taken during its use to minimize potential health risks.

InChI:InChI=1/C18H37NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-19-15-17-20-18-16-19/h2-18H2,1H3

Upstream product

• 110-91-8 morpholine 
• 112-71-0 1-Bromotetradecane 
• 5338-53-4 1-morpholino-1-oxotetradecane 

Downstream Products

• 139072-43-8 4-ethyl-4-tetradecyl-morpholinium; ethyl sulfate 

Relevant academic research and scientific papers

Evaluation of a novel morpholine-typed Gemini surfactant as the collector for the reverse flotation separation of halite from carnallite ore

In froth flotation separation process, the collector molecular design has a crucial effect on potash processing to ensure sustainable production of potassium fertilizer (KCl) that is important to secure food supply in human society. Carnallite is an important source of KCl fertilizer production in industry. Reverse flotation has been used to separate halite (NaCl) impurities from carnallite (KCl·MgCl2·6H2O) for carnallite resources. However, progress in the carnallite resource reverse froth flotation has been constrained by the inherent limitation of traditional collector molecules with a single hydrophilic head and single hydrophobic chain per molecule. Herein, a novel morpholine-based Gemini molecule with double hydrophilic heads and hydrophobic chains, butanediyl-α, ω-bis (morpholino tetradecylammonium bromide) (BMTB) was synthesized and applied as the flotation collector in the reverse flotation separation for carnallite mineral. The better flotation performance of Gemini BMTB was achieved, compared to the traditional monomeric surfactant N-(n-Tetradecyl) morpholine (TDM). The bench-scale froth flotation separation results revealed that BMTB exhibited outstanding affinity and selectivity for NaCl crystals from carnallite at natural pH, resulting in less collector dosages – only 1/3 of TDM molecules. In contrast with traditional monomeric surfactant TDM (120 g/t), less amount of Gemini BMTB (40 g/t) – only one third of TDM molecules, was needed to obtain higher KCl recovery (KCl recovery raised by 4.69%). Meanwhile, the grade of NaCl with 40 g/t BMTB collector (2.19%) was lower than that with 120 g/t TDM collector (3.91%), and the grade of KCl with BMTB collector (22.59%) was higher than that with TDM collector (22.12%). Therefore, this work demonstrated the next-generation of flotation collector for the reverse froth flotation separation of the carnallite resources.

Synthesis, surface adsorption, micellization behavior and antibacterial activity of novel gemini surfactants with morpholinium headgroup and benzene-based spacer

Two series of novel gemini surfactants with morpholinium headgroup and benzene-based rigid spacers (abbreviated as (Mor)m-P-m and (Mor)m-BP-m, where m represents the carbon numbers of hydrophobic chains) were synthesized and characterized by 1H NMR, ESI-MS, and FT-IR spectra. The effect of lengths of rigid spacer and hydrocarbon chain on their solution properties and antibacterial activities were systematically investigated. Due to the existence of morpholinium, they have a superior surface activity to the classic gemini surfactants. (Mor)m-BP-m possess lower CMC and γcmc than (Mor)m-P-m, which is assumed to be related to the conformation change of spacer. The possible arrangement models for the adsorptions of (Mor)m-P-m and (Mor)m-BP-m at the air-water interface were proposed by comparing their surface parameters with those of other similar surfactants. The pre-micellar associations occur in aqueous solutions of (Mor)16-P-16, (Mor)14-BP-14 and (Mor)16-BP-16. The thermodynamic parameters indicate the micellar processes are spontaneous, and (Mor)m-BP-m have stronger aggregation tendency than (Mor)m-P-m. Dynamic light scattering (DLS) and transmission electron microscopy (TEM) show they spontaneously self-assemble into vesicle, and the aggregate size of (Mor)m-BP-m is larger than (Mor)m-P-m. These surfactants showed excellent antibacterial properties against Bacillus subtilis and Escherichia coli. Compared with (Mor)m-P-m, (Mor)m-BP-m exhibit a higher activity.

Alkylated Piperazines and Piperazine-Azole Hybrids as Antifungal Agents

The extensive use of fluconazole (FLC) and other azole drugs has caused the emergence and rise of azole-resistant fungi. The fungistatic nature of FLC in combination with toxicity concerns have resulted in an increased demand for new azole antifungal agents. Herein, we report the synthesis and antifungal activity of novel alkylated piperazines and alkylated piperazine-azole hybrids, their time-kill studies, their hemolytic activity against murine erythrocytes, as well as their cytotoxicity against mammalian cells. Many of these molecules exhibited broad-spectrum activity against all tested fungal strains, with excellent minimum inhibitory concentration (MIC) values against non-albicans Candida and Aspergillus strains. The most promising compounds were found to be less hemolytic than the FDA-approved antifungal agent voriconazole (VOR). Finally, we demonstrate that the synthetic alkylated piperazine-azole hybrids do not function by fungal membrane disruption, but instead by disruption of the ergosterol biosynthetic pathway via inhibition of the 14α-demethylase enzyme present in fungal cells.

Nematocidal activity of long alkyl chain amides, amines and their derivatives on dog roundworm larvae

The nematocidal activity of amides and amines having a long alkyl chain against the second-stage larva of dog roundworm, Toxocara canis, was examined. Long chain acyl amides with smaller substituents on the nitrogen showed stronger activity and the activity of cyclic amine amides was stronger than that of acyclic ones. In a series of homologous amides, the activity was dependent on the alkyl chain length: it reached a maximum at an optimal chain length and decreased in both shorter and longer homologues. The relationship between the activity and hydrophobicity of the homologues was analysed by the use of the bilinear model. The hydrophobicity of a compound, which gives a maximal activity, was similar for all neutral amides, but amides which have an additional amine group in the molecule had different values. Tertiary amines and their salts having a long alkyl chain also showed nematocidal activities comparable to those of the corresponding amides. The salts killed the larva at concentrations lower than their critical micell concentration, suggesting that they behave as a single molecule for the nematocidal action.