Sterically hindered phenols

Ершов, В. В.; Володькин, А. А.; Никифоров, Г. А.; Dyumaev, K. M.

doi:10.1007/bf00920272

Cited by 23 publications

(8 citation statements)

References 2 publications

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“…In the spectra of compounds Ie, Ve, Vh, Vm-r, Vu, VIc, VIIc and VIIId containing 4-hydroxy-3,5-di-tert-butylphenyl groups, the signals of hydroxyl group protons are in the form of singlets in the region of 5.05-5.15 ppm, which is characteristic of shielded phenols [16].…”

Section: A-c III Vi A-i Vii A-dmentioning

confidence: 99%

Oxazolidine derivatives from natural C2-C5 mercaptans. Synthesis and use

Келарев

Кошелев

Latyuk

et al. 2006

Chem Technol Fuels Oils

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RESEARCHOXAZOLIDINE DERIVATIVES FROM NATURAL C 2 -C 5 MERCAPTANS. SYNTHESIS AND USE V. I. Kelarev, V. N. Koshelev, V. I. Latyuk, and K. D. Korenev UDC 542.953:547.729.7:547.841 ____________________________________________________________________________________________________ I. M. Gubkin Russian State University of Oil and Gas.of N-substituted β-amino alcohols with βand γ-alkylthioketones. They were tested as oxidation inhibitors for blended diesel fuels. Some of these compounds, added in small amounts to OMI industrial inhibitor, can significantly increase its effectiveness in thermal stabilization of this fuel.In continuing the research on synthesis of alkylthioalkyl derivatives of five-and six-member heterocycles using the C 2 -C 5 natural mercaptan fraction as key compounds [1-4], we obtained di-, tri-, and tetra-substituted oxazolidines containing alkylsulfide groups in the α-, β-, or γ-position to the ring. Compounds of this type could be interesting as stabilizers and additives to hydrocarbon fuels and lube oils [5], corrosion inhibitors, fungicides, plant growth regulators, and inhibitors of biodegradation of organic materials.Cyclocondensation of N-substituted b-amino alcohols with carbonyl compounds is the most convenient method of obtaining N-substituted oxazolidines [6,7]. N-substituted 1-amino-3-alkylthio-2-propanols (Ia-f), β-alkylthioketones (IIa-c), and 5-alkylthio-2-pentanones (III), synthesized from C 2 -C 5 mercaptan fractions, were used as the initial compounds in the present study [8,9]. This fraction was separated from Orenburg Gas Processing Plant odorant and contains 94.5 vol. % C 2 -C 5 mercaptans, where 1-propanethiol (20.5 vol. %), 2-propanethiol (38.5 vol. %), and 2-methyl-1-propanethiol (23 vol. %) predominate. The initial N-substituted b-amino alcohols (Ia-f) were synthesized with 72-84% yields (Table 1) by reacting a mixture of 1-alkylthio-3-chloro-2-propanols (IV) [8] with primary aliphatic and aromatic amines in 2-propanol at 50-60°C for 6-7 h using an aqueous solution of the base as an acceptor for the hydrogen chloride separated. As a result of condensation of equimolecular quantities of β-amino alcohols Ia-f and paraform (or the corresponding

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Section: A-c III Vi A-i Vii A-dmentioning

confidence: 99%

Oxazolidine derivatives from natural C2-C5 mercaptans. Synthesis and use

Келарев

Кошелев

Latyuk

et al. 2006

Chem Technol Fuels Oils

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“…All the compounds under consideration also show absorption due to the residue of sterically hindered phenol: a fairly narrow band at 3655-3635 cm -1 characteristic of screened phenol hydroxyl [14]; two bands of medium intensity in the interval 1260-1220 cm -1 due to vibrations of At-OH bonds in screened phenols [15], and two groups of bands in the regions 885-870 cm-1 and 835-820 era-1 (extraplanar deformation vibrations of tetrasubstituted benzene ring).…”

Section: Chzch"conhnh2 + R1--xmentioning

confidence: 99%

“…In the ESR spectra of the synthesized compounds (Table 2), the proton signals of the hydroxyl groups are representgxl as singlets in the interval 4.84-5.21 ppm, which is characteristic of sterically hindered phenols [14,16] The initial hydrochlorides of ethyl iminoesters Ia-e [17], IVa [18], IVb [19], IVc [20], and IVd [21]; hydrazides of /~-[4-hydroxy-3,5-di(tert-butyl)phenyl]propionic (IIc) [22] and indolyl-3-acetic (IIf) [23] acids; 4-hydroxy-3,5-di(tertbutyl)benzoic acid (Via) [24] and its chloride [25], as well as 2-chloromethyl-l,3,4-oxadiazoles VIIa [26] and VIIb [27] were prepared by well-known methods, references to which are given below.…”

Section: Chzch"conhnh2 + R1--xmentioning

confidence: 99%

Synthesis of 2,5-disubstituted 1,3,4-oxadiazoles containing a sterically hindered 4-hydroxy-3,5-di(tert-butyl)phenyl group

Келарев¹,

Кошелев²,

Silin³

1997

Chem Heterocycl Compd

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Continuing our studies of the synthesis of azoles containing groups of screened phenol [1][2][3][4], this paper presents data on the preparation of 2,5-disubstituted 1,3,4-oxadiazoles containing 4-hydroxy-3,5-di(tert-butyl)phenyl (HDBP) substituents.Data presented in the literature pertain only to the preparation and properties of 1,3,4-oxadiazoles containing groups of sterically hindered phenol [3,[5][6][7], although compounds of this type may be of interest as potential biologically active substances, and also as stabilizers and additives to polymeric materials, hydrocarbon fuels, and lubricating oils.

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“…The content of SHP fragments was calculated as 144 described in (Arefjev et al, 1999). The molar extinction for the model compound 4-145 methyloxymethyl-2,6-di-tert-butylphenol (3a-model) (Ershov et al, 1972) and 2b were ε 146 =1700±30 L·mol -1 ·cm -1 at λ max = 276 nm; for ethyl 2-benzamido-3-(3,5-di-tert-butyl-4-147 hydroxyphenyl)acrylate (3c-model) ( The two-dimensional isotropic scattering spectra were azimuthally averaged, converted to an 193 absolute scale, and corrected for detector efficiency by dividing by the incoherent scattering 194 spectrum of pure water, which was measured with a 1 mm path length quartz cell. 195 196…”

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confidence: 99%