930
FARZALIEV et al.
1
Hg; nD20 =1.4522. H NMR spectrum, δ, ppm: 0.9 t
(CH3), 1.130–1.150 m (CH2CH2CH2CH2CH2), 3.05 t
(NCH2CH2N), 3.30 t (OCH2), 3.95 s (NCH2O). Found,
%: N 8.41. C20H42N2O2. Calculated, %: N 8.19.
N,N'-Bis(ethyloxymethyl)piperazine (Ib). In a sim-ilar
way, 20 g (0.6 mole) of paraformaldehyde, 60 ml of ethanol,
1/2 granule of KOH, and 17 g (0.2 mole) of piperazine in
20 ml of ethanol after vacuum distillation of the reaction
mixture yielded 19.3 g (48%) of a liquid product,
N,N'-Bis(decyloxymethyl)piperazine (Ih).
In a similar way, 20 g (0.6 mole) of paraformaldehyde,
100 ml of n-decyl alcohol, and 17 g (0.2 mole) of
piperazine yielded 64.4 g (75.5%) of a liquid product, bp
173°C/1 mm Hg; nD20 =1.4568. 1H NMR spectrum, δ, ppm:
0.85 t (CH3), 1.33–1.68 [(CH2)8], 3.10 t (NCH2CH2N),
3.38 t (OCH2), 3.95 s (NCH2O). Found, %: N 6.95.
C26H54N2O2. Calculated, %: N 6.57.
1
bp 130–132°C/1.5 mm Hg; nD20 =1.4488. H NMR
spectrum, δ, ppm: 1.2 t (CH3), 2.96 t (NCH2CH2N),
3.30 m (OCH2), 4.08 s (NCH2O). Found, %: N 14.06.
C10H22N2O2. Calculated, %: N 13.86.
N,N'-Bis(propyloxymethyl)piperazine (Ic). In a sim-
ilar way, 20 g (0.6 mole) of paraformaldehyde,
80 ml of n-propanol, 1/2 granule of KOH, and 17 g
(0.2 mole) of piperazine in 20 ml of propanol yielded
23.9 g (52%) of a liquid product, bp 137–140°C/1
CONCLUSIONS
1
mm Hg; nD20 =1.4525. H NMR spectrum, δ, ppm:
(1) Three-component condensation of piperazine
with formaldehyde and aliphatic alcohols yielded N,N'-
bis(alkyloxymethyl)piperazines.
0.9 t (CH3), 1.3–1.5 m (CH2CH2), 2.95 t (NCH2CH2N),
3.30 t (OCH2), 4.06 s (NCH2O). Found, %: N 12.50.
C12H26N2O2. Calculated, %: N 12.17.
(2) The yield of the target product tends to increase
with lengthening of the hydrocarbon radical in the initial
alcohol.
N,N'-Bis(isopropyloxymethyl)piperazine (Id). In
a similar way, 20 g (0.6 mole) of paraformaldehyde,
80 ml of isopropanol, 1/2 granule of KOH, and 17 g
(0.2 mole) of piperazine in 20 ml of isopropanol yielded
22.5 g (49%) of a liquid product, bp 142–143°C/1 mm
(3) The compounds synthesized exhibit antimicrobial
properties with respect to microorganisms that infect
cooling lubricants and lubricant oils, but are superseded
in performance characteristics by similar derivatives of
1,3-diazacycloalkanes (imidazolidines).
1
Hg; nD20 =1.4474. H NMR spectrum, δ, ppm: 0.95 d
(2CH3), 3.1 t (NCH2CH2N), 3.38 t (OCH), 3.95 s
(NCH2O). Found, %: N 12.30. C12H26N2O2. Calculated,
%: N 12.17.
N,N'-Bis(butyloxymethyl)piperazine (Ie). In a sim-
ilar way, 20 g (0.6 mole) of paraformaldehyde, 80 ml of
n-butanol, 1/2 granule of KOH, and 17 g (0.2 mole) of
piperazine yielded 31.0 g (60%) of a liquid product, bp
148–152°C/1 mm Hg; nD20 =1.4522. 1H NMR spectrum,
δ, ppm: 0.83 t (CH3), 1.33–1.66 (CH2CH2), 3.15 t
(NCH2CH2N), 3.38 t (OCH2), 4.95 s (NCH2O). Found, %:
N 10.97. C14H30N2O2. Calculated, %: N 10.85.
REFERENCES
1. Bennet, E.O., Int. Biodeter. Bull., 1978, vol. 104, no. 23,
pp. 551–554.
2. Paulus, W., Erdöl Kohle Erdgas Petrochem., 1984, vol. 37,
no. 7, pp. 303–307.
3. Rapoport, I.A., Dokl. Akad. Nauk SSSR, 1946, vol. 54,
no. 5, pp. 65–68.
N,N'-Bis(isobutyloxymethyl)piperazine (If). In a sim-
ilar way, 20 g (0.6 mole) of paraformaldehyde, 80 ml of
isobutanol, 1/2 granule of KOH, and 17 g (0.2 mole) of
piperazine yielded 29.8 g (58 %) of a liquid product, bp
143–147°C/1 mm Hg; nD20 =1.4482. 1H NMR spectrum,
δ, ppm: 0.9 d (2CH3), 1.5 m (CH), 3.1 t (NCH2CH2N),
3.27 t (OCH), 4.15 s (NCH2O). Found, %: N 11.20.
C14H30N2O2. Calculated, %: N 10.85.
4. Farzaliev, V.M., Abbasova, M.T., Soltanova, Z.K., et al.,
Nauch. Izv. Sumgait Gos. Univ., Razd. Estestv. Tekh. Nauk,
2007, vol. 7, no. 2, pp. 41–48.
5. Farzaliev, V.M., Abbasova, M.T., Babaeva, G.B., and
Soltanova, Z.K., Az. Khim. Zh., 2007, no. 2, pp. 15–17.
6. GOST (State Standard) 9.085–78. Cooling Lubricants:
Bioresistance Test Methods.
7. GOST (State Standard) 9.052–75. Oils and Lubricants:
Laboratory Test Methods for Resistance to Fungi.
N,N'-Bis(heptyloxymethyl)piperazine (Ig). In a sim-
ilar way, 20 g (0.6 mole) of paraformaldehyde, 100 ml
of n-heptane, and 17 g (0.2 mole) of piperazine yielded
44.5 g (65%) of a liquid product, bp 157–160°C/1 mm
8. GOST (State Standard) 9.082–87. Oils and Lubricants:
Laboratory Test Methods for Resistance to Bacteria.
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 82 No. 5 2009