Journal "Chemistry and Technology of Organic Substances", N 3 (11) /2019
Section I
ORGANIC SYNTHESIS
Yakovenko Еu.А.1, Raskil’dina G.Z.1, Mryasova L.М.2, Zlotsky S.S.1
Synthesis and herbicidal activity of some esters and amides that include
saturated oxygencontaining heterocycles
Federal State Budgetary Educational Institution of Higher Education «Ufa State Petroleum
Technological University»,
450062, Ufa, str. Kosmonavtov, 1.
2
State Budgetary Institution «Scientific Research Technological Institute of Herbicides and Plant
Growth Regulators with Experimental Production»,
450112, Ufa, str. Ulyanov, 65.
1
Abstract
Monochloroacetic, salicylic and terephthalic acid derivatives containing a 1,3dioxacyclan fragment have been synthesized. The structures of the compounds
obtained were proved by NMR spectroscopy and chromatography-mass-spectrometry. The herbicidal activity of esters and amides based on monochloroacetic
acid, salicylic and terephthalic acid chlorides was studied. It was found that the
obtained compounds are able to successfully inhibit the length and mass of wheat
shoots and the length of the shoots of sunflower. Salicylic acid ester of 5-ethyl-5hydroxymethyl-1,3-dioxane exhibited maximum herbicidal activity.
Keywords: complex esters; chlorides; amides; 1,3-dioxacycloalkanes; herbicides.
References
1. Ganiullina E.R., Voronenko B.I., Kuznetsov V.M., Mazitov R.M., Zlotsky S.S.,
Dekhtyar T.F. Herbicidal and biological activity of gem-dichlorocyclopropanes
based on arylallyl ethers // Bashkir Chemical Journal. 2008. Vol. 15. N 3.
P. 53–56.
2. Raskil’dina G.Z., Borisova Yu.G., Valiev V.F., Mikhailova N.N., Zlotsky S.S.,
Zaikov G.E., Emelina O.Yu. Substituted ethers and acetals with biological activity // Bulletin of Kazan Technological University. 2014. Vol. 17. N 15.
P. 166–169.
3. Shavshukova S.Yu., Shvetsov S.V., Zlotsky S.S. Modern industrial herbicides.
Synthesis and application. Ufa: Monograph LLC. 2011. P. 64.
4. Raskil’dina G.Z., Yakovenko E.A., Mryasova L.M., Zlotsky S.S. Synthesis and
herbicidal activity of aryloxyacetic acid esters and amides containing a
cycloacetal fragment // University News. Chem. and chemical tech. 2019.
Vol. 62. N 1. P. 91–97.
5. Raskil’dina G.Z., Borisova Yu.G., Mikhailova N.N., Mryasova L.M.,
Kuznetsov V.M., Zlotsky S.S. Plant growth regulators based on cyclic ketals
and their derivatives // University News. Chem. and chemical tech. 2017.
Vol. 60. N 1. P. 95–101. DOI: 10.6060/tcct.2017601.5475.
6. Timofeeva S.A., Giniyatulina E.Kh., Kuznetsov V.M., Udalova E.A.,
Shavshukova S.Yu., Zlotsky S.S. Herbicidal activity of a number of substituted
cyclic acetals // Bashkir Chemical Journal. 2011. Vol. 18. N 3. P. 71–73.
1
7. Yakovenko E.A., Bayburtli A.V., Borisova Yu.G., Raskil’dina G.Z. O-acylation
of dioxane alcohols with acid chlorides // Bashkir Chemical Journal. 2017.
Vol. 24. N 2. P. 52–56.
8. Gafarova Yu.T., Vostrikova O.S., Zlotsky S.S., Dokichev V.A. Splitting of 1,3ioxacyclanes by organoaluminum compounds // Bashkir Chemical Journal.
2000. Vol. 7. N 6. P. 3–6.
9. Yakovenko E.A., Baymurzina Yu.L., Raskil’dina G.Z., Zlotsky S.S. Synthesis
and biological activity of a number of hetero- and carbocyclic derivatives of
monochloroacetic acid // Journal of Applied chemistry. 2019 (print article).
10. Yakovenko, E.A., Bulatova, Yu.I., Mirakyan, S.M., Valiev, V.F., Borisova,
Yu.G., Mikhailova, N.N., Raskil’dina, G.Z. Derivatives of alcohols and amines
containing cyclopropane and cycloacetal fragment // Bashkir Chemical Journal.
2016. Vol. 23. N 4. P. 94–98.
11. Kazakova A.N., Kuznetsov V.M., Musavirova L.R., Mikhailova N.N.,
Bogomazova A.A., Mudrik T.P., Zlotsky S.S. Herbicidal activity of substituted
gem-dichlorocyclopropanes // Bashkir Chemical Journal. 2013. Vol. 20. N 1.
P. 8–10.
12. Raskil’dina G.Z., Valiev V.F., Sultanova R.M., Zlotsky S.S. Production,
structure and transformations of cyclic formalites of glycyrin // Russian
Chemical Bulletin. 2015. N 9. P. 2095–2099.
__________________________________________________________________
Section II
TECHNOLOGY OF ORGANIC SUBSTANCES
Komissarova G.M., Belyaev E.L, Smirnov M.K., Sokhadze L.A., Turygin V.V.,
Khrustalev R.A., Kondrat’yev V.B.
A method for preparing 4,4′-diaminodiphenyl ether and 4,4′-diaminodiphenyl
ether of resorcinol in the conditions of small-scale production
Federal state unitary enterprise «State scientific-research Institute of organic chemistry and technology»
State Scientific Center of Russian Federation, 111024, Moscow, Shosse Entuziastov, 23,
e-mail: [email protected], tеl.: +7 (495) 673-78-26
Abstract
A cost saving and easily realizable method for preparing 4,4′-diaminodiphenyl
ether and 4,4′-diaminodiphenyl ether of resorcinol based on domestic raw materials
is developed. The process is conducted at moderate temperatures and atmospheric
pressure and does not envisage the use of costly catalysts. Optimum synthesis conditions are determined, a block diagram of the technological process is proposed.
Keywords: catalytic reduction; hydrazine hydrate; 4,4′-diaminodiphenyl ether;
4,4′-diaminodiphenyl ether of resorcinol.
References
1. Patent US4400538A, C07C209/36. Fixed bed catalyst for MNB and DNT
hydrogenation / Chadwick D.H., Boyd T.E.; Mobay Chemical Corp, а corp. of
N.J. (Mobay Corp); pub. 23.08.1983.
2. Patent US4185036, C07C209/36. Hydrogenation of mixed aromatic nitrobodies
/ Cossaboon K. F.; E I du Pont de Nemours and Co; pub. 22.01.1980.
2
3. Patent US3032586, С07C209/36. Hydrogenation of dinitrotoluene to toluylene
diamine / Dierichs H., Holzrichter H.; Bayer AG, Mobay Corp; pub.
01/05/1962.
4. Patent US3213141, B01J23/40. Catalytic reduction of aromatic dinitro
compounds / Graham D. E., Freyermuth H. B., Hort E.V.; GAF Chemicals
Corp; pub. 19.10.1965.
5. Berkman B.E. Promyshlennyj sintez aromaticheskih nitrosoedinenij i aminov.
M.: Himiya, 1964. 344 s.
6. Sovremennye metody organicheskogo sinteza. L.: Izd-vo LGU, 1980. S. 137–
179.
7. Patent CN101429132. Synthesis of 1,3-di(4-aminophenoxy)benzene. pub. 13.05.
2009.
8. Patent US 4692554A, C07C1/00. Process for producing 1,3-bis(3aminophenoxy)benzene / Keizaburo Yamaguchi, Yukihiro Yoshikawa,
Yoshimitsu Tanabe, Kenichi Sugimoto, Akihiro Yamaguchi; Mitsui Toatsu
Chemicals Inc, а corp. of Japan (Mitsui Chemicals Inc); pub. 08.09.1987.
9. Vorozhcov N.N. Osnovy sinteza promezhutochnyh produktov i krasitelej. M.:
Goskhimizdat, 1950. S. 240–243.
10. Porter H.K. The Zinin reduction of nitroarens //Organic Reactions. 1973. Vol.
20. P. 455–481.
11. Masaru Hojoy, Asuot Akagi, Yoshiro Ogata. Kinetics of the reduction of
nitrobenzenes by sodium disulfide // J. Amer. Chem. Soc. 1960. Vol. 82. N 10.
P. 2459–2462.
12. Hlavaty J., Volke J., Bakos V . Electrochemical reduction of 2,2’-dinitrophenyl
ether and 2,2’-dinitrodiphenylamine at mercury cathodes // Collection Czech.
Chem. Commun. 1983. Vol. 48. N 2. P. 379–380.
13. Bogoslovskij B.M., Kazakova Z.S. Skeletnye katalizatory, ih primenenie v
organicheskoj himii. M.: Goskhimizdat, 1957. 144 s.
14. Milto V.I. Sintez poliyadernykh aromaticheskikh soedinenii, soderzhashchikh
oksidnye i karbonilnye mostikovye zvenya: diss. ... dokt. khim. nauk.
Yaroslavskii gosudarstvennyi universitet im. P.G.Demidova, 2007.
15. A. s. SSSR, 1694201, 1991. MPK S07S209/38. Katalizator dlya gidrirovaniya
dinitrodifenilovogo efira Sokol’skij D. V., Popov N.I., Zhubanov K.A. i dr.
Zayavl. 27.11.84; opubl. 30.11.91. Byul. N 44.
16. Balcom D., Furst A. Reductions with hydrazine hydrate catalyzed by Raney
Nickel. I. Aromatic nitro compounds to amines // J. Amer. Chem. Soc. 1953.
Vol. 75. N 17. P. 4334. DOI: 10.1021/ja01113a502.
17. Patent CN1485315(А) Process for preparing 3,4-diaminodiphenyl ether; pub.
31.04.2004.
18. Han B.H., Shin D.H. Organic Sonochemistry. Ultrasonic fcceleration of the
reduction of aromatic nitro compounds with hydrazine-iron in the presence of
activated carbon // Bull. Korean Chem. Soc. 1985. Vol. 6. N 5. P. 320.
19. Patent HUT52755A. New process for producing substituted anilines / Gergely
Helya, Endre Palosi, Dezsoe Korbonits et al.; Chinoin gyogyszer es Vegyeszet;
pub. 28.11.1991.
3
20. Clive D.L., Angoh A.G., Sharon B.M. Radical spirocyclization: synthesis of an
appropriately oxygenated spiro compound related to the antitumor antibiotic
fredericamycin A // J. Org. Chem. 1987. 52. N 7. P. 1339-1342. DOI:
10.1021/jo00383a032.
21. Miyata T., Ishino Y., Hirashima T. Novel synthesis of 4,5-bis(arylthio)-2,3,4,5tetrahydro-1-benzothiepins: Noteworthy cyclization by the reaction of 2butynediol with arenethiols in the presence of zinc iodide // Synthesis. 1987. N
9. P. 827-828. DOI: 10.1055/s-1987-28090.
22. Lauwiner M., Roth R., Rys P. Reduction of aromatic nitro compounds with
hydrazine hydrate in the presence of an iron oxide/hydroxide catalyst. III. The
selective reduction of nitro groups in aromatic azo compounds // Appl. Catal.
A: Gen. 1999. Vol. 177. N 1. P. 9-14. DOI: 10.1016/S0926-860X(98)00247-6.
23. Kumbhar P.S., Valente J.S., Millet J.M.M., Figueras F. Mg–Fe hydrotalcite as
a catalyst for the reduction of aromatic nitro compounds with hydrazine
hydrate // J. Catal. 2000. Vol. 191. N 2. P. 467-473. DOI: 10.1006/
jcat.2000.2827.
24. Larsen J.W., Freund M., Kim K.Y., Sidovar M., Stuart J.L. Mechanism of the
carbon catalyzed reduction of nitrobenzene by hydrazine // Carbon. 2000. Vol.
38. N 5. 655-561. DOI: 10.1016/S0008-6223(99)00155-4.
25. Electron ionization (EI) mass-spectral library NIST–14, 2014.
------------------------------------------------------------------------------------------------Koshelev A.V., Golovkov V.F, Derevyagina I.D., Kaabak L.V., Smirnova Zh.V.,
Epifanova O.A., Mamontov S.P., Eleev Yu.A.
Research of humic preparations obtained from lignite
Federal state unitary enterprise «State scientific-research Institute of organic chemistry and technology»
State Scientific Center of Russian Federation, 111024, Moscow, Shosse Entuziastov, 23,
e-mail: [email protected], tеl.: +7 (495) 673-78-91
Abstract
Chemical composition research results of humic preparations obtained from lignite
are presented. Humic preparations were obtained according to the classical industrial technology of alkaline hydrolysis at elevated temperatures and cavitation technology with processing of coal-alkaline pulp in an ultrasonic field. The size of dispersed phase was determined and low molecular weight organic substances included in the composition of humic preparations were also established. The main
differences between humic preparations obtained from lignite and preparations
obtained from peat are considered. Drill sludge disposal technology by humic
preparations and recommendations for possible use of received ameliorators
aiming technogenic lands recultivation are presented.
Keywords: humic preparations; humic acids; lignite; alkaline hydrolysis; ultrasonic
cavitation; recultivation of technogenic territories; drill sludge.
References
1. GOST 54221–2010 Guminovye preparaty iz burykh i okislennykh kamennykh
uglejj. Metody ispytanijj. M.: Standartinform. 2012. 21 s.
2. Purygin P.P., Potapova I.A., Vorob’ev D.V. Guminovye kisloty: ikh vydelenie,
struktura i primenenie v biologii, khimii i medicine // Samarskijj
gosudarstvennyjj universitet, centr medicinskikh innovacijj doktora Vorob’eva
4
D.V. URL: https://www.sworld. com.ua/simpoz3/92.pdf (data obrashhenija
23.12.2018).
3. Orlov D.S., Grishina L.A. Praktikum po khimii gumusa. M.: Izd-vo MGU, 1981.
S. 272.
4. Swift R.S. Organic matter characterization (chap 35) Methods of soil analysis.
Madison, WI: Soil Science Society of America, 1996. P. 3. P. 1018-1020.
5. Koshelev A.V., Derevjagina I.D., Golovkov V.F., Kaabak L.V., Epifanova O.A.,
Mamontov S.P., Eleev Ju.A., Glukhan E.N. Khimicheskijj sostav guminovykh
preparatov, poluchennykh iz torfa // Chemistry and Technology of Organic
Substances, 2019, N 1. S. 25-37.
6. Perminova I.V., Zhilin D.M. Guminovye veshhestva v kontekste zelenojj khimii
// Zelenaja khimija v Rossii. Sbornik statejj. Pod red. V.L. Lunina, P. Tundo,
E.S. Loktevoj. M.: MGU, 2004. S. 146-162.
7. Perminova I.V. Analiz, klassifikacija i prognoz svojjstv gumusovykh kislot:
diss. ... dokt. khim. nauk. Moskva, 2000. 359 s.
8. Grechishheva N.Ju. Razrabotka nauchnykh osnov primenenija guminovykh
veshhestv dlja likvidacii posledstvijj neftezagrjaznenija pochvennykh i
vodnykh sred: diss. ... dokt. khim. nauk. Moskva, 2016. 326 s.
9. Cherdakova A.S. Ehkologicheskaja ocenka vlijanija razlichnykh guminovykh
preparatov na sostojanie tekhnogenno-izmenennykh serykh lesnykh pochv:
diss ... kand. biol. nauk. Rjazan’, 2016. 161 s.
10. OOO
«NPF
«Progressivnye
Tekhnologii».
URL:
https://www.
rusprofile.ru/id/2876649 (data obrashhenija 03.01.2019).
11. GOST 256543–2013. Ugli burye, kamennye i antracity. Klassifikacija po
geneticheskim i tekhnologicheskim parametram. M.:Standartinform. 2016. 20 s.
12. GOST R 54249–2010 Udobrenija zhidkie guminovye na osnove torfa.
Tekhnicheskie uslovija. M.: Standartinform, 2012. 14 s.
13. Inzhenernyjj spravochnik DPVA. Klassifikacija laboratornykh bumazhnykh
fil’trov. URL: https://www.dpva.ru/Guide/ GuideEquipment/ FiltrationAnd
Separation/PaperFiltration/ (data obrashhenija 03.01.2019).
14. Koshelev A.V., Tikhomirova E.I., Aleksashin A.V. Issledovanie sostava i
fiziko-khimicheskikh svojjstv burovogo shlama iz shlamovykh ambarov
dlitel’nogo sroka khranenija // Fundamental’nye i prikladnye issledovanija:
problemy i rezul’taty. Materialy I Mezhdunarodnojj nauchno-prakticheskojj
konferencii, posvjashhennojj 100-letiju FGBOU VO «GGNTU im. akad.
M.D.Millionshhikova», 02–04 nojabrja 2017 g. Rossija, Chechenskaja
Respublika, g. Groznyjj. V 2-kh tomakh. T.1. – Groznyjj: FGBOU VO
«GGNTU», 2017. S. 681-685.
15. Golubev E.V., Soromotin A.V., Veprenceva N.A., Mikushina N.B. Sostav i
svojjstva burovykh otkhodov Zapadnojj Sibiri // Mir nauki, kul’tury,
obrazovanija. 2010. N 6 (25). S. 319-320.
16. MU 2.1.7.730–99. Gigienicheskaja ocenka kachestva pochvy naselennykh
mest. Metodicheskie ukazanija. M.: Minzdrav Rossii, 1999. 43 s.
17. GN 2.1.7.2041–06. Predel’no dopustimye koncentracii (PDK) khimicheskikh
veshhestv v pochve. M.: Minzdrav Rossii, 2006.
5
18. O rekul’tivacii zemel’, snjatii, sokhranenii i racional’nom ispol’zovanii
plodorodnogo sloja pochvy. Postanovlenie Pravitel’stva RF ot 23.02.1994
N 140.
19. GOST 13038–84 Semena sel’skokhozjajjstvennykh kul’tur. Metod
opredelenija vskhozhesti. M.:Standartinform, 2011. 64 s.
20. Ob utverzhdenii kriteriev otnesenija otkhodov k I – V klassam opasnosti po
stepeni negativnogo vozdejjstvija na okruzhajushhuju sredu. Prikaz № 536 ot
4.12.2014 g. Ministerstva prirodnykh resursov i ehkologii RF.
21. MVI Biologicheskie metody kontrolja. Metodika opredelenija toksichnosti
vody i vodnykh vytjazhek iz pochv, osadkov stochnykh vod, otkhodov po
smertnosti i izmeneniju plodovitosti dafnijj. Federal’nyjj reestr
FR.1.39.2007.03222. M.:Akvaros, 2007. 71 s.
22. MVI Biologicheskie metody kontrolja. Metodika opredelenija toksichnosti
vod, vodnykh vytjazhek iz pochv, osadkov stochnykh vod i otkhodov po
izmeneniju urovnja fluorescencii khlorofilla i chislennosti kletok vodoroslejj.
Federal’nyjj reestr FR.1.39.2007.03223. M.:Akvaros, 2007. 64 s.
__________________________________________________________________
Section III
TEST METHODS FOR SUBSTANCES AND MATERIALS
Korneeva O.I, Semenova Z.V., Struzhkova N.G., Zamulaeva E.V.,
Sakovich M.V., Kostikova N.A.
Development of titrimetric method for determination of the basic substance
mass fraction in 4,4´-bis(maleinimidodiphenyl) methane
Federal state unitary enterprise «State scientific-research Institute of organic chemistry and technology»
State Scientific Center of Russian Federation, 111024, Moscow, Shosse Entuziastov, 23,
e-mail: [email protected], tеl.: +7 (495) 673-78-91
Abstract
The determination of basic substance mass fraction in 4,4´-bis(maleinimidodiphenyl)methane by means of the back acid-base titration method is
proposed. Optimal conditions for carrying out the reaction (type and method of
titration, solvent, temperature and time of interaction of imide with alkali, titrant
concentration, indicator) were selected. The metrological characteristics of the
method are calculated.
Keywords: 4,4´-bis(maleinimidodiphenil)methane; analysis; titrimetric method;
back acid-base titration; equivalence point; mass fraction.
References
1. Osnovy analiticheskoj himii: ucheb. dlya vuzov: v 2-h kn., kn. 1, izd. 3-e
pererab. i dop. / pod red. Yu.A. Zolotova. M.: Vysshaya shkola, 2004. 361 s.
2. Vasil’ev V.P. Analiticheskaya himiya: ucheb. dlya vuzov: v 2-h ch., ch. 1.
[Gravimetricheskij i titrimetricheskij metody analiza] M.: Vysshaya shkola,
1989. 320 s.
3. Reutov O.A., Kurc A.L., Butin K.P. Organicheskaya himiya. V 4-h chastyah.
M.: Izd-vo MGU, 1999, 2336 s.
4. GOST R 55878–2013 Rectified hydrolytic technical ethyl alcohol. Specifications. Vveden s 01.09.2014. М.: Standartinform, 2014. 20 s.
6
5. GOST 9805–84 Isopropyl alcohol. Specifications. Vveden s 01.01.1986. М.:
IPK Iz-vo Standartov, 1998. 16 s.
6. GOST 25794.1–83 Reagents. Methods of preparation of standard volumetric
solutions for acid-base titration. Vveden s 01.07.1984. М.: Standartinform,
2008. 12 s.
7. Andreev I.Е., Prihod’ko V.V., Shekina M.P., Kostikova N.A. The method of
obtaining 4,4´-bis(maleinimidodiphenyl)metane, suitable for realization as of
low-tonnage production // Chemistry and Technology of Organic Substances.
2018. N 2 (6). S. 26-35.
8. GOST 53228–2008 Non-automatic weighing instruments. Part 1. Metrological
and technical requirements. Tests. Vveden s 01.01.2010. М.: Standartinform,
2010. 137 s.
9. Lur’e Yu.Yu. Spravochnik po analiticheskoj himii: Sprav. izd. 6-e izd., pererab.
i dop. M.: Himiya, 1989. 448 s.
10. RMG 61–2010 Gosudarstvennaya sistema obespecheniya edinstva izmerenij.
Pokazateli tochnosti, pravil’nosti, precizionnosti metodik kolichestvennogo
himicheskogo analiza. Metody ocenki. M. Standartinform, 2013, 62 s.
------------------------------------------------------------------------------------------------Novikova I.V., Smirnova Zh.V., Petrunin V.A., Novikov R.I., Kurygina L.P.
Perfluoroacylation of β-aminoalcohols for their analysis by gas
chromatography mass spectrometry
Federal state unitary enterprise «State scientific-research Institute of organic chemistry and technology»
State Scientific Center of Russian Federation, 111024, Moscow, Shosse Entuziastov, 23,
e-mail: [email protected], tеl.: +7 (495) 673-78-91
Abstract
N-methyl-bis-(trifluoroacetamide) and some N-perfluoroacetylimidazoles are considered for chemical modification of β-aminoalcohols – degradation products of
toxic chemicals. It is shown that most effective acylation reagents are N-pentafluoropropionylimidazole and N-heptafluorobutyrylimidazole, as a result the stable
derivatives are formed. Electron ionization mass spectra of trifluoroacetyl,
pentafluoropropionyl and heptafluorobutyryl derivatives β-aminoalcohols are
studied. The results can be used for β-aminoalcohols identification and quantitation
by gas chromatography/mass spectrometry.
Keywords: β-aminoalcohols; derivatization; perfluoroacylation; N-methyl-bis(trifluoroacetamide); N-perfluoroacetylimidazole; gas chromatography mass spectrometry.
References
1. Konvencija o zapreshhenii razrabotki, proizvodstva, nakoplenija i primenenija
himicheskogo oruzhija i o ego unichtozhenii. OON. Zheneva, 1993.
2. Black R. M., Muir B. Derivatisation reactions in the chromatographic analysis
of chemical warfare agents and their degradation products // Journal of Chromatography A. 2003. Vol. 1000. P. 253–281. DOI: 10.1016/s00219673(03)00183-3.
3. Blau K., Halket J. Handbook of derivatives for chromatography. John Wiley &
Sons Ltd, 1993. 369 p. DOI: 10.1007/BF02916441.
7
4. Recommended operating procedures for analysis in the verification of chemical
disarmament / Editor: P. Vanninen. The Ministry for foreign affairs of Finland,
University of Helsinki, 2017. 809 p.
5. Zaikin V.G., Mikaya A.I. Himicheskie metody v mass-spektrometrii
organicheskih soedinenij. M.: Nauka, 1987. 200 s.
6. Donike M. Acylierung mit bis(acylamiden) N-methyl-bis(trifluoracetamid) und
bis(trifluoracetamid), zwei neue reagenzien zur trifluoracetylierung // Journal of
chromatography. 1973. Vol. 78. P. 273–279.
7. Knapp D.R. Handbook of analytical derivatization reactions. A Wiley
Interscience Publication. New York, 1979. 741 p.
8. Garg P., Purohit A., Tak V.K., Dubey D.K. Enhanced detectability of fluorinated derivatives of N,N-dialkylamino alcohols and precursors of nitrogen
mustards by gas chromatography coupled to Fourier transform infrared spectroscopy analysis for verification of chemical weapons convention // Journal of
Chromatography
A.
2009.
Vol.
1216.
P.
7906–7914.
DOI:
10.1016/j.chroma.2009.09.032.
9. Pardasani D., Palit M., Gupta A.K., Kanaujia P.K., Dubey D.K. Gas chromatography–mass spectrometry analysis of trifluoroacetyl derivatives of precursors
of nitrogen and sulfur mustards for verification of chemical weapons convention
// Journal of Chromatography A. 2004. Vol. 1059. P. 157–164. DOI:
10.1016/j.chroma.2004.10.039.
10. Dubey D.K., Pardasani D., Palit M., Gupta A.K., Jain R. On-matrix
derivatisation-extraction of precursors of nitrogen- and sulfur-mustards for
verification of chemical weapons convention // Journal of Chromatography A.
2005. Vol. 1076. P. 27–33. DOI: 10.1016/j.chroma.2005.04.066.
11. Palit M., Mallard G. Dispersive derivatization liquid–liquid extraction of degradation products/precursors of mustards and V-agents from aqueous samples //
Journal of Chromatography A. 2011. Vol. 1218. P. 5393–5400. DOI:
10.1016/j.chroma.2011.06.008.
12. NIST/EPA/NIH. NIST Mass Spectral Library. National Institute of Standards
and Technology, US Secretary of Commerce: USA, 2017.
13. OPCW Central Analytical Database, e-OCAD v.21, Technical Secretariat of
the Organization for the Prohibition of Chemical Weapons, 2019.
14. OPCW Validation Group Working Database, VGWD-2018, Technical Secretariat of Organisation for the Prohibition of Chemical Weapons, 2018.
15. Kondrat’ev V.А., Yudina I.А., Kutkin А.V., Novikova I.V., Novikov R.I.,
Smirnova Zh.V. Preparative method of synthesis of 1-(halomethyl)-(±)-3quinuclidinol halides// Journal of General Chemistry. 2016. Vol. 86. N. 9.
P. 1573–1575. DOI: 10.1134/S1070363216090280.
__________________________________________________________________
8
Section IV.
RESEARCH IN THE FIELD OF CHEMICAL AND BIOLOGICAL
SAFETY
Golovkov V.F, Koshelev A.V., Glukhan E.N., Eleev Yu.A., Afanasyev V.V.,
Bogoyavlenskaya Yu.S.
Methodical approach for survey of obsolete pesticides storages and
abandoned toxic chemicals burial sites
Federal state unitary enterprise «State scientific-research Institute of organic chemistry and technology»
State Scientific Center of Russian Federation, 111024, Moscow, Shosse Entuziastov, 23,
e-mail: [email protected], tеl.: +7 (495) 673-78-91
Abstract
Based on the previous experience of the Federal State Unitary Enterprise
«GosNIIOKhT» a methodical approach for survey of obsolete pesticides storages
(Biysk, Altai region) and abandoned pesticides burial sites («Bolshie Izbishchi»,
Lipetsk region) is proposed, including: consideration of existing suitable survey
methods; planning and sampling procedures development; obtainment of reliable
data, regarding to the composition of pesticides and contamination grade; planning
of further storage (site) elimination or conservation procedures.
Keywords: obsolete pesticides; pesticides storage; landfill; burial site; survey
methodology; sampling; lindane; granozan.
References
1. Monitoring pesticidov v ob’ektax prirodnoj sredy Rossijskoj Federacii:
Ezhegodnik. Kn1/2. Obninsk: NPO «Tajfun», 1992. 425 s.
2. Volgina T.N., Novikov V.T., Reguzova D.V. Sovremennye metody
obezvrezhivaniya nekondicionnyh pesticidov // Polzunovskij vestnik. 2010. N 3.
S. 166–170.
3. Pesticidy: ugroza real’na. Obzor deyatel’nosti nepravitel’stvennyh organizacij
regiona Vostochnoj Evropy, Kavkaza i Central’noj Azii po vyyavleniyu
nesankcionirovannyx zapasov ustarevshih i zapreshhennyh pesticidov.
Redaktor–sostavitel’: Speranskaya O.A. M.: «E’ko-Soglasie», 2004. 71 s.
4. Stojkie organicheskie zagryazniteli: obzor situacii v Rossii. Sostaviteli:
Speranskaya O.A., Citcer O. Mezhdunarodnyj proekt po likvidacii SOZ. URL:
http://www.ipen.org (data obrashheniya: 5.02.2018).
5. Banshhikov B.P. Ugroza e’kologii dolzhna byt’ otvedena // Zashhita i karantin
rastenij. 2007. N 5. S. 7–8.
6. SNiP 2.01.28–85. Poligony po obezvrezhivaniyu i zaxoroneniyu toksichnyh
promyshlennyx othodov. Osnovnye polozheniya po proektirovaniyu. M.: CITP
Gosstroya SSSR, 1985. 20 s.
7. Federal’nyj zakon ot 19.07.1997 g. N 109-FZ «O bezopasnom obrashhenii s
pesticidami i agroximikatami» (v red. ot 13.07.2015 g.). Spravochno-pravovaya
sistema «Garant». URL: http://base.garant.ru (data obrashheniya: 5.02.2018).
8. SanPiN 1.2.2584–10 Gigienicheskie trebovaniya k bezopasnosti processov
ispytanij, hraneniya, perevozki, realizacii, primeneniya, obezvrezhivaniya i
utilizacii pesticidov i agrokhimikatov. Utverzhdeny Postanovleniem Glavnogo
9
gosudarstvennogo sanitarnogo vracha RF ot 02.03.2010 g. N 17. URL:
http://base.garant.ru (data obrashheniya: 5.02.2018).
9. Koshelev A.V., Golovkov V.F., Eleev Yu.A., Afanas’ev V.V., Surovcev V.V.
Osobennosti obsledovaniya proizvodstvennyx ob’ektov nakoplennogo
e’kologicheskogo ushherba / Materialy III Rossijskoj konferencii: «Aktual’nye
nauchnye i nauchnotexnicheskie problemy obespecheniya ximicheskoj
bezopasnosti Rossii», 8-9 iyunya 2016 g. Moskva, 2016. S.124.
10. Oficial’nyj sajt Upravleniya Rossel’xoznadzora po Altajskomu krayu i
respublike Altaj. URL: http: // www.rshn-alt.ru (data obrashheniya: 5.02.2018).
11. Stokgol’mskaya konvenciya o stojkih organicheskih zagryaznitelyah. Tekst i
prilozheniya. Shvejcariya, Zheneva, 2001. 53 s.
12. Amirova Z.K., Speranskaya O.A. Novye stojkie organicheskie supertoksikanty
i ix vliyanie na zdorov’e cheloveka. M.: «E’ko-Soglasie», 2016. 169 s.
13. Chapaevsk. 100 let. Istoriko-publicisticheskie ocherki. Samara: OOO «Ofort»,
2011. 312 s.
14. GOST 7854–55 Geksaxloran texnicheskij. M.: Gosstandart SSSR, 1955. URL:
http://docs.cntd.ru/document/437086719 (data obrashheniya 5.02.2018).
15. Spravochnik po yadoximikatam. Sost. Popov P.V. M.: Gosximizdat, 1956. 623 s.
16. Mel’nikov N.N. Pesticidy. Himiya, texnologiya i primenenie. M.: Ximiya,
1987. 712 s.
17. Promyshlennye xlororganicheskie produkty. Spravochnik. Pod red. L.A. Oshina.
M.: Ximiya, 1978. 656 s.
18. Himizaciya sel’skogo xozyajstva. Nauchno-texnicheskij slovar’-spravochnik.
Pod obshhej redakciej prof. L. L. Balasheva i akad. S. I. Vol’fkovicha. M.:
Nauka, 1964. 399 s.
19. GOST 6218–76 Geksaxloran dust. Texnicheskie usloviya. Gosstandart SSSR,
1976. URL: http://www.normacs.com/doc/d106409/ (data obrashheniya:
5.02.2018).
20. TU MXP N OSh–261–54. Kujbyshevskij sovnarxoz, 1954. URL:
http://agronomius.livejournal.com/tag/ (data obrashheniya: 5.02.2018).
21. TU
113-04–254–87
Geksaxloran
dust.
URL:
http://www.nwnormativ.ru/search_result/ (data obrashheniya: 5.02.2018).
22. Smol’yakova V.M., Podgornaya M.E Ocenka bezopasnosti pesticidov v
yuzhnom sadovodstve Rossii // Sadovodstvo i vinogradarstvo XXI veka. Ch. 5.
Krasnodar, 1999. S. 72–73.
23. Doklad Komiteta po rassmotreniyu stojkih organicheskih zagryaznitelej o
rabote ego vtorogo soveshhaniya. Dobavlenie. Harakteristiki riskov lindana.
Shvejcariya, Zheneva. 2006. 28 s.
24. Golovkov V.F., Koshelev A.V., Eleev Yu.A. i dr. Issledovanie soderzhaniya
e’tilmerkurkhlorida v ustarevshih pesticidah // Khimiya i tekhnologiya
organicheskih veshhestv. 2018. N 2 (6). S. 49-54.
25. Gosudarstvennyj katalog pesticidov i agrokhimikatov, razreshennyh k
primeneniyu na territorii Rossijskoj Federacii. URL:
http://mcx.ru/documents/document/v7_show/22770.133.htm (data obrashheniya:
5.02.2018).
10
26. Capok M.V. Razrabotka i issledovanie metodov texnicheskogo monitoringa
himicheski opasnyx ob’ektov na peresechennoj mestnosti. Diss. kand. tekhn.
nauk. Izhevsk: IzhGTU. 2008, 202 s.
27. GOST R 22.1.10–2002. Bezopasnost’ v chrezvychajnyh situaciyah. Monitoring
himicheski opasnyx ob’ektov. Obshhie trebovaniya. M.: IPK Izdatel’stvo
standartov, 2000, 6 s.
28. GOST 14189–81 Pesticidy. Pravila priyomki, metody otbora prob, upakovka,
markirovka, transportirovanie i xranenie. Spravochno-pravovaya sistema
«Garant». URL: http://base.garant.ru (data obrashheniya: 5.02.2018).
29. GOST R 53123–2008. Kachestvo pochvy. Otbor prob. Chast’ 5. Rukovodstvo
po izucheniyu gorodskih i promyshlennyh uchastkov na predmet zagryazneniya
pochvy. Spravochno-pravovaya sistema «Garant». URL: http://base.garant.ru
(data obrashheniya: 5.02.2018).
30. Sokolov V.P., Pavlov M.V., Sadovnikov S.V., Afanas’ev V.V. Safe destruction
of the content of unorganized pesticide landfills // Chemistry and Technology of
Organic Substances. 2017. N 2(2). S. 70-77 (in Rus.).
31. Kaabak L.V., Koshelev A.V., Belikov V.A., Eleev Yu.A., Strukov O.G.,
Morozova O.T., Vlasova Z.V., Afanas’ev V.V. Conformational transformations
of the γ-isomer of hexachlorocyclohexane during prolonged storage // Chemistry
and Technology of Organic Substances. 2018. N 1 (5). S. 75-81 (in Rus.).
11
