Higher n-acyl-n, n1-triphenylaminoisobutyrate chlorides having the ability to inhibit chemical metal corrosion in hydrogen sulfide-containing saline environments

 

(57) Abstract:

Usage: in metallurgy, as a corrosion inhibitor metal in hydrogen sulfide-containing environments. The inventive product of the highest N-acyl-N N1N2-triphenyl--aminoisobutyrate f-crystals PhN(CnH2n+1C=O)CH2C(CH3)H-C-NHPh[(+)NHPh)Cl-where n =8,10,17. BF C31H40ClN30. So pl. 159-160C. a Yield of 92%. BF C33H44ClN30. So pl. 166-168C. the Yield 95% CF C40H58ClN30. So pl. 148-150C. the Yield 89%. Reagent 1: acylchlorides. Reagent 2: N, N1N2-triphenyl--aminoisobutyrate. Reaction conditions: anhydrous sulphuric ether. table 2.

The invention relates to the field of organic chemistry, specifically to derived-aminoadamantane acid - higher N-acyl-N,N1N2- triphenyl- -aminoisobutyrate chlorides (hydrochloridum higher N-acyl-N, N1N2-triphenyl- -aminoisobutyrate) of General formula (I) having the ability to inhibit chemical (corrosive environment) corrosion of metals in saline environments containing hydrogen sulfide, i.e., under conditions typical of oilfield equipment and pipelines in needoba is, what some of which have high antiviral activity [1]. Among the derivatives of aminoamides closest structural analogue of the claimed compounds (I) is a-amino-N-stearoylethanolamine (II) [2].

The main difference of structure (II) of the inventive compounds (I) is the lack of phenyl substituents at the nitrogen atoms amidnogo portion and an acylated amino group. Such substituents are present in the structures of N-acetyl-N,N1N2triacylglycerides (III) [5], is also able to provide structural analogues of the claimed compounds.

About any practically useful properties of substances (II) and (III) is unknown.

The claimed structure (I) are bifunctional and can be considered as a combination of the amide fragment (specifically, anilide) higher saturated carboxylic acid (A), N1N2-disubstituted ameeneemagu fragment (B) and connecting the hydrocarbon level (S).

CC

C17HNHCHH2< / BR>
H2r

Information about the ability amidaniel salts (fragment B) or free amidino to inhibit the corrosion of metals in the literature is missing. At the same time there is information about high efficiency amides vissible similar in structure to the claimed substances (I), having the ability to inhibit the corrosion of metal (the prototype) is stearylamine (IV).

However, in terms of this hydrogen-sulfide corrosion inhibitor insufficiently active (see below).

Object of the invention is the identification of new derivatives of amides of higher carboxylic acids, showing an increased ability to inhibit metal corrosion in hydrogen sulfide-containing saline environments.

This object is achieved by the claimed compounds of General formula (I) having the ability to inhibit chemical metal corrosion in hydrogen sulfide-containing saline environments. The ability to inhibit corrosion of the metal of the proposed connection is superior to known structural analogues.

These compounds are obtained by acylation of N1N2-diphenyl - N - phenylaminopyrimidine anhydrides of higher carboxylic acids.

P R I m e R 1. N1N2-diphenyl - N-phenylamino-N-palagonitization (I, n=8).

To a solution of 2.0 g (0,006 mol) of N1N2-diphenyl - N - phenylaminopyrimidine in 30 ml of anhydrous sulphuric ether under stirring was added 1.07 g (0,006 mol) of pearsonville 20 LASS="ptx2">

CH2C(CH3) C (I)

C17HNHPh(VI)< / BR>
P R I m m e R 2. N1N2-diphenyl - N-phenylamino-N - underinvestigation (I, n=10) are obtained analogously to example 1 from 2.1 g (0,0063 mol) of N1N2-diphenyl - N - phenylaminopyrimidine and 1.3 g (0,0063 mol) of undegenerated.

P R I m e R 3. N1N2-diphenyl - N-phenylamino-N - stearoylethanolamine chloride (I, n= 17) are obtained analogously to example 1 from 2.1 g (0,0063 mol) of N1N2-diphenyl - N - phenylisopropylamine and of 1.93 g (0,0063 mol) of staurolite.

The compounds are slightly soluble in water, soluble in alcohols, dipolar aprotic solvents, chloroform.

The claimed compounds are presented in table. 1. Their structure proved elemental analysis data of IR-, UV - and PMR spectra.

In the IR spectra of the products (vaseline oil) recorded the absorption band of skeletal vibrations of aromatic cycles at 1495-1500 and 1595-1600 cm-1, (N+(H) when 1570-1575 cm-1, (N N) around 1615 cm-1the most intense absorption band (C=0) around 1660 cm-1and a series of absorption bands (N+(H) in the interval 2400-2800 cm-1with highs of about 2695 and 2735 cm-1. In the UV spectra (in methanol is s absorption in the region of 260 nm in the UV spectra, as well as the position of the peak (S=0) at 1660 cm-1and not at 1690 cm-1as in the N1N2-diphenyl-N1-acetylcytidine, the presence in the PMR spectra (DCl3) broadened singlet (N+-H) diphenylsilane ameeneemagu fragment in the field 12,15 memorial plaques indicate that the acyl substituent in the products (I) is located at the amino group, and not attached to medinova fragment [5].

Test inhibitors of corrosion of metals in serovodorodsoderzhashchij mineralized environment spend on steel 3 for 6 h according OST 39-099-79 [9] in a standard solution with a density of 1.12 g/cm3containing, g/l: sodium chloride 144; calcium chloride 23, magnesium chloride 22; calcium sulfate 1,4, white spirit of 0.7, the sulfide of 0.10.

The results of the tests of the claimed compounds and the corresponding data for the prototype (stearylamine) and used in the oil industry inhibitor API-2 on THE other 6-02-1076-76 representing hydrochloride a mixture of aminopropanol [10] are given in table.2.

The examination table. 2 shows that the proposed connections provide practical protection against chemical corrosion (Z 90% and above at a concentration of 50 mg/l), whereas ANP-2 shows the same activity that prototip) at a concentration of 50 mg/l 2.25 times less active, than the worst of the inventive sample (example 3) and 5 times than the best (example 2). The best of the inventive samples (example 2) inhibits corrosion in fluids containing hydrogen sulfide mineralized environment 20 times that provides almost complete protection against corrosion.

The properties possessed by the inventive compounds (I), may be able to find a use for them in the oil industry for corrosion protection systems for maintaining reservoir pressure and pipelines.

Higher N-acyl-N, N1N2-triphenyl- -aminoisobutyrate chlorides of General formula

CHCCl-,

where n = 8, 10, 17,

having the ability to inhibit chemical metal corrosion in hydrogen sulfide-containing saline environments.

 

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