Brine amine

Several methods have received considerable research attention as alternatives to salt curing. These include use of sodium bisulfite as a disinfectant to allow preservation with or without decreased salt in a brine cure use of disinfectants such as quatenary amines for temporary preservation in direct shipping to the taimery from the packing plant (see Disinfectants and antiseptics) preservation of hides by radiation sterilization (see Sterilization techniques) and substitution of materials such as potassium chloride for sodium chloride. These methods have found only limited commercial success. 

Scrubbing andDesliming. Sylvinite ores in North America contain 1—6 wt % water-insoluble clays. A significant portion of these clays is less than 0.002 mm in diameter. If not removed or controUed in some manner, clay bodies that are dispersed in the flotation solution, ie, brine saturated with KCl and NaCl, absorb the amine coUector, which is added to effect flotation separation, and the coUector is rendered ineffective. Clay is the most troublesome impurity encountered in the processing of sylvinite ore. 

Longer-chain amines, ie, arachidyl—behenyl (C2Q to C22) amines, are used ia special cases ia which brine temperatures exceed 35°C. At temperatures higher than ambient, normal tallow amine tends to dissolve and therefore is unavailable to coat the surfaces of the potassium chloride crystals. Amine consumption is from 50 g/1 (ca 40 wt % KCl) of high grade ore, to 150 g/1 (ca 20 wt % KCl) of low grade ore. 

Production of KCl at the Wendover, Utah operation employs a large 7000 acre complex of solar ponds. Both shallow brine wells and deeper wells are used to pump brine into the pond complex. In the preconcentration ponds water is evaporated and sodium chloride is crystallized. Later the brine is transferred to production ponds where sylvinite is deposited. Brine is then transferred to other ponds where camaUite is crystallized. Sylvinite is removed from drained ponds with self-loading scrapers and taken to the plant were KCl is separated by flotation with an amine oil collector. The camaUite,... 

The classic method for the determination of corrosion inhibitors in oil field brines is the dye transfer method. This method is basically sensitive to amines. Within this method, there are many variations that the analyst may use to determine the amount of corrosion inhibitor in either water or crude oil. Unfortunately these methods detect all amines present as corrosion inhibitors [1174]. 

Improved high-pressure liquid chromatography (HPLC) methods have been developed for the analysis of quaternary salt type corrosion inhibitors in brine waters [400]. However, these methods are not suitable for imidazolines and amido-amines. A method based on fluorescence detection has been described for the quantitative analysis of the imidazoline- and amido-amine-type corrosion inhibitors in both oil field water and crude oil samples by HPLC [1174]. 

Furthermore, an a,P-ethylenically unsaturated aldehyde together with organic amines will form intermediate products, which are further reacted with a carboxylic acid, an organic halide, or an epoxide-containing compound [ 1760]. The final products are suitable corrosion inhibitors for preventing corrosion of steel in contact with corrosive brine and oil and gas well fluids. 

Similarly, a high-density brine, useful as a drilling fluid for deep wells, is made corrosion resistant by adding an aliphatic or aromatic aldehyde and thiocyanates [817]. The aldehyde can be reacted with a primary amine before use. 

A methanogenic bacterium was isolated from oil reservoir brines by enrichment with trimethylamine. Methane production occurred only with trimethyl-amine compounds or methanol as substrates. Sodium ions, magnesium ions, and potassium ions were all required for growth. This organism appears to be a member of the genus Methanohalophilus based on substrate utilization and general growth characteristics [695]. 

R. M. Matherly, J. Jiao, J. S. Ryman, and D. J. Blumer. Determination of imidazoline and amido-amine type corrosion inhibitors in both crude oil and produced brine from oilfield production. In Proceedings Volume. 50th Annu NACE Int Corrosion Conf (Corrosion 95) (Orlando, FL, 3/26-3/31), 1995. 

Method A CHCI, (24 g, 0.2 mol) is added with stirring to the amine (0.2 mol) and TEBA-Cl (0.5 g, 2.2 mol) in a two-phase system of CH2Cl2 (50 ml) and aqueous NaOH or KOH (50%, 60 ml). The exothermic reaction begins to reflux after ca. 10 min and is stirred until the temperature subsides (ca. 1 h). H20 (200 ml) is then added and the organic phase is separated, washed well with dilute HC1, H20 and brine, dried (K2CO,), and fractionally distilled. 

The acidic aqueous layer from the aqueous acetic acid/sodium acetate/pentane hydrolysis of 2-alkylcyclo-hexanonc imines is neutralized with solid potassium hydroxide to pH 14, and then saturated with sodium chloride. This aqueous solution is extracted with four portions of diethyl ether, and the combined ethereal layer is washed with brine. Drying over potassium carbonate and concentration gives an oil which is distilled 85% recovery bp 57-59 °C/0.02 Torr [x]D — 13.75 (c = 5.8, benzene). If the rotation of the distilled amine is lower than 13.40, it is purified via its hydrochloride. Thus, a solution of the amine in ice-cold diethyl ether is treated with dry hydrogen chloride by bubbling through a fritted disk. The amine hydrochloride is collected by filtration and recrystallized from ethanol mp 151-152°C. 

Ethyl bromoacetate (5.54 mL, 50 mmol) in THF (25 mL) was added dropwise to a cooled (ice bath) soln of amine 29 (llOmmol) in THF (25 mL). After stirring for 2.5 h at rt, the mixture was taken to dryness and the residue resuspended in E O. The predpitate was removed by filtration and washed with E O. The combined organic phase was taken to dryness and the residue purified by column chromatography (silica gel, Et20). 4M NaOH (2.5 mL) was added to the soln of /V-alkyl-Gly-OEt (10 mmol) in dioxane (35 mL) and MeOH (12.5 mL). After stirring for 30 min at rt, the mixture was taken to dryness. The residue was dissolved in H20 and the pH adjusted to 9-9.5 with coned HC1. To this mixture a soln of Fmoc-OSu (10 mmol) in MeCN (20 mL) was added in one portion and the pH maintained at 8.5-9.0 with TEA. The MeCN was removed and the residue added to 20% citric acid soln (60 mL). The soln was extracted with EtOAc (3 x 75 mL) and the combined organic layers were washed with H20 and brine, dried (Na2S04), and taken to dryness. The residual oil was recrystallized (EtOAc/hexane). 

A soln of the diphenyl [l-(benzyloxycarbonylamino)alkyl]phosphonate 4 in 45% HBr/AcOH (150 mL per 0.1 mol) was kept at rt for 1 h. Removal of the solvent and volatile products in vacuo yielded the oily hydrobromide, which crystallized upon addition of anhyd Et20. The free amine was obtained by suspending the hydrobromide in CHC13 and shaking in a separatory funnel with an equal volume of 2M NaOH until all the solid dissolved. The CHC13 layer was separated, washed with brine, dried (MgS04), and concentrated to yield 19 in >90% yield mp (R1 = Me) 36-39°C mp (R = iPr) 60-63°C mp (R1 = iBu) 57-58 °C mp (R = Ph) 63-65 °C mp (R = Bzl) 65-67 °C. 

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