Petroleum ChemistryPetroleum ChemistryНефтехимия0028-24213034-5626The Russian Academy of Sciences65557310.31857/S0028242123060023RSSHIAArticlesСтатьиResearch ArticleDvoynye metallotsianidnye (dmc) katalizatory: sintez, stroenie i mekhanizm deystviya (obzor)Двойные металлоцианидные (dmc) катализаторы: синтез, строение и механизм действия (обзор)PyatakovD. A.ПятаковД. А.dinamitry06@gmail.comNifant'evI. E.НифантьевИ. Э.Институт нефтехимического синтеза им. А.В. Топчиева РАНМосковский государственный университет имени М.В. Ломоносова15122023636NO6 (2023)№6 (2023)80983711022025Copyright ©; 2023, Russian Academy of SciencesCopyright ©; 2023, Российская академия наук2023Russian Academy of SciencesРоссийская академия наукhttps://journals.eco-vector.com/0028-2421/article/view/655573

Двойные металлоцианидные (double metal cyanide, DMC) катализаторы безальтернативны для использования в промышленном процессе полимеризации пропиленоксида (PO) с целью получения полипропиленоксида (PPO) со свойствами, необходимыми для специализированных применений: низкой степенью ненасыщенности, высокими молекулярными массами и гидроксильными числами. Современные промышленные образцы демонстрируют высокую эффективность, давая возможность проводить процесс с экстремально низкими загрузками - до 25 ppm, что не требует регенерации катализатора и не приводит к ухудшению свойств полимеров. Главными недостатками этих материалов являются относительно сложный синтез и чувствительность к влаге. Несмотря на то, что DMC-катализаторы известны еще с 1960-х гг., их гибридный характер и переменный состав до сих пор затрудняют исследование и выявление взаимосвязи между способом получения, составом и свойствами этих материалов. Данный литературный обзор призван систематизировать и проанализировать информацию по синтезу, строению и механизму действия DMC-катализаторов. Подробно рассмотрен как традиционный синтез, так и нетрадиционные методы получения DMC-катализаторов. Большое внимание уделено вопросам строения каталитического центра и механизма полимеризации, а также физико-химическим свойствам этих материалов, как гетерогенных катализаторов.

Двойные металлоцианидные (double metal cyanide, DMC) катализаторы безальтернативны для использования в промышленном процессе полимеризации пропиленоксида (PO) с целью получения полипропиленоксида (PPO) со свойствами, необходимыми для специализированных применений: низкой степенью ненасыщенности, высокими молекулярными массами и гидроксильными числами. Современные промышленные образцы демонстрируют высокую эффективность, давая возможность проводить процесс с экстремально низкими загрузками - до 25 ppm, что не требует регенерации катализатора и не приводит к ухудшению свойств полимеров. Главными недостатками этих материалов являются относительно сложный синтез и чувствительность к влаге. Несмотря на то, что DMC-катализаторы известны еще с 1960-х гг., их гибридный характер и переменный состав до сих пор затрудняют исследование и выявление взаимосвязи между способом получения, составом и свойствами этих материалов. Данный литературный обзор призван систематизировать и проанализировать информацию по синтезу, строению и механизму действия DMC-катализаторов. Подробно рассмотрен как традиционный синтез, так и нетрадиционные методы получения DMC-катализаторов. Большое внимание уделено вопросам строения каталитического центра и механизма полимеризации, а также физико-химическим свойствам этих материалов, как гетерогенных катализаторов.

DMC-катализаторыгибридные материалыгетерогенный катализполимеризация с раскрытием циклаполипропиленоксидIonescu M. Chemistry and Technology of Polyols for Polyurethanes. Shropshire: Rapra Technology, 2005.Brocas A.-L., Mantzaridis C., Tunc D., Carlotti S. Polyether synthesis: from activated or metal-free anionic ring-opening polymerization of epoxides to functionalization // Prog. Polym. Sci. 2013. V. 38. № 6. P. 845-873. https://doi.org/10.1016/j.progpolymsci.2012.09.007Herzberger J., Niederer K., Pohlit H., Seiwert J., Worm M., Wurm F.R., Frey H. Polymerization of ethylene oxide, propylene oxide, and other alkylene oxides: synthesis, novel polymer architectures, and bioconjugation // Chem. Rev. 2016. V. 116. № 4. P. 2170-2243. https://doi.org/10.1021/acs.chemrev.5b00441Valvekens P., De Vos D. Chapter 1. Double metal cyanides as heterogeneous catalysts for organic reactions. In: New Materials for Catalytic Applications / Eds. V.I. Parvulescu, E. Kemnitz. Amsterdam: Elsevier, 2016. P. 1-12.Ruiz-Bermejo M., Menor-Salván C., Osuna-Esteban S., Veintemillas-Verdaguer S. The effects of ferrous and other ions on the abiotic formation of biomolecules using aqueous aerosols and spark discharges // Orig. Life Ev. Biosph. 2007. V. 37. № 6. P. 507-521. https://doi.org/10.1007/s11084-007-9107-0Ruiz-Bermejo M., Rogero C., Menor-Salván C., Osuna-Esteban S., Martín-Gago J.Á., VeintemillasVerdaguer S. Thermal wet decomposition of Prussian blue: implications for prebiotic chemistry // Chem. Biodivers. 2009. V. 6. № 9. P. 1309-1322. https://doi.org/10.1002/cbdv.200900024Fu H., Liu C., Zhang C., Ma W., Wang K., Li Z., Lu X., Cao G. Enhanced storage of sodium ions in Prussian blue cathode material through nickel doping // J. Mater. Chem. A. 2017. V. 5. № 20. P. 9604-9610. https://doi.org/10.1039/C7TA00132KLiu S., Pan G.L., Li G.R., Gao X.P. Copper hexacyanoferrate nanoparticles as cathode material for aqueous Al-ion batteries // J. Mater. Chem. A. 2015. V. 3. № 3. P. 959-962. https://doi.org/10.1039/C4TA04644GLiu J., Li X., Rykov A.I., Fan Q., Xu W., Cong W., Jin C., Tang H., Zhu K., Ganeshraja A.S., Ge R., Wang X., Wang J. Zinc-modulated Fe-Co Prussian blue analogues with well-controlled morphologies for the efficient sorption of cesium // J. Mater. Chem. A. 2017. V. 5. № 7. P. 3284-3292. https://doi.org/10.1039/C6TA10016C.Takahashi A., Tanaka H., Parajuli D., Nakamura T., Minami K., Sugiyama Y., Hakuta Y., Ohkoshi S.-I., Kawamoto T. Historical pigment exhibiting ammonia gas capture beyond standard adsorbents with adsorption sites of two kinds // J. Am. Chem. Soc. 2016. V. 138. № 20. P. 6376-6379. https://doi.org/10.1021/jacs.6b02721Kaye S.S., Long J.R. Hydrogen storage in the dehydrated Prussian blue analogues M3[Co(CN)6]2 (M = Mn, Fe, Co, Ni, Cu, Zn) // J. Am. Chem. Soc. 2005. V. 127. № 18. P. 6506-6507. https://doi.org/10.1021/ja051168tFerlay S., Mallah T., Ouahès R., Veillet P., Verdaguer M. A room-temperature organometallic magnet based on Prussian blue // Nature. 1995. V. 378. № 6558. P. 701-703. https://doi.org/10.1038/378701a0Milgrom J. Method of making a polyether using a double metal cyanide complex compound // Patent US № 3278457. 1966.Le-Khac B., Wang W. Double-metal cyanide catalysts which can be used to prepare polyols and the processes related thereto // Patent US № 6696383. 2004.Le-Khac B. Highly active double metal cyanide catalysts // Patent US № 5693584. 1997.Chen X., Kumbhalkar M., Fisk J., Murdoch B. In situ monitoring of double metal cyanide (DMC) catalyst synthesis by raman spectroscopy // Raman Technology for Today's Spectroscopists. 2023. V. 38. № S6. P. 5-10. 18. https://doi.org/10.56530/spectroscopy.nq1471w5An N., Li Q., Yin N., Kang M., Wang J. Effects of addition mode on Zn-Co double metal cyanide catalyst for synthesis of oligo(propylene-carbonate) diols // Appl. Organomet. Chem. 2018. V. 32. № 11. P. e4509. https://doi.org/10.1002/aoc.4509Le-Khac B., Bowman P.T., Hinney H.R. Highly active double metal cyanide complex catalysts // Patent US № 5712216. 1998.Sebastian J., Srinivas D. Effects of method of preparation on catalytic activity of Co-Zn double-metal cyanide catalysts for copolymerization of CO2 and epoxide // Appl. Catal. A: Gen. 2014. V. 482. P. 300-308. https://doi.org/10.1016/j.apcata.2014.06.007Huang Y.J., Qi G.R., Chen L.S. Effects of morphology and composition on catalytic performance of double metal cyanide complex catalyst // Appl. Catal. A: Gen. 2003. V. 240. № 1. P. 263-271. https://doi.org/10.1016/S0926-860X(02)00452-0Zhang W., Lin Q., Cheng Y., Lu L., Lin B., Pan L., Xu N. Double metal cyanide complexes synthesized by solvent-free grinding method for copolymerization of CO2 and propylene oxide // J. Appl. Polym. Sci. 2012. V. 123. № 2. P. 977-985. https://doi.org/10.1002/aP.34544Peeters A., Valvekens P., Ameloot R., Sankar G., Kirschhock C.E.A., De Vos D.E. Zn-Co double metal cyanides as heterogeneous catalysts for hydroamination: a structure-activity relationship // ACS Catal. 2013. V. 3. № 4. P. 597-607. https://doi.org/10.1021/cs300805zPeeters A., Valvekens P., Vermoortele F., Ameloot R., Kirschhock C., De Vos D. Lewis acid double metal cyanide catalysts for hydroamination of phenylacetylene // Chem. Commun. 2011. V. 47. № 14. P. 4114-4116. https://doi.org/10.1039/C0CC05335JDharman M.M., Ahn J.-Y., Lee M.-K., Shim H.-L., Kim K.-H., Kim I., Park D.-W. Moderate route for the utilization of CO2-microwave induced copolymerization with cyclohexene oxide using highly efficient double metal cyanide complex catalysts based on Zn3[Co(CN)6]2 // Green Chem. 2008. V. 10. № 6. P. 678-684. https://doi.org/10.1039/B801132JKim I., Byun S.H., Ha C.-S. Ring-opening polymerizations of propylene oxide by double metal cyanide catalysts prepared with ZnX2 (X = F, Cl, Br, or I) // J. Polym. Sci., Part A: Polym. Chem. 2005. V. 43. № 19. P. 4393-4404. https://doi.org/10.1002/pola.20914Kim I., Yi, M.J., Lee K.J., Park D.-W., Kim B.U., Ha C.-S. Aliphatic polycarbonate synthesis by copolymerization of carbon dioxide with epoxides over double metal cyanide catalysts prepared by using ZnX2 (X = F, Cl, Br, I) // Catal. Today. 2006. V. 111. № 3. P. 292-296. https://doi.org/10.1016/j.cattod.2005.10.039Chen S., Zhang X., Lin F., Qi G. Preparation of double metal cyanide compleces from water-insoluble zinc compounds and their catalytic performance for copolymerization of epoxide and CO2 // React. Kinet. Catal. Lett. 2007. V. 91. № 1. P. 69-75. https://doi.org/10.1007/s11144-007-4891-0Zhang X.H., Chen S., Wu X.M., Sun X.K., Liu F., Qi G.R. Highly active double metal cyanide complexes: effect of central metal and ligand on reaction of epoxide/CO2 // Chin. Chem. Lett. 2007. V. 18. № 7. P. 887-890. https://doi.org/10.1016/j.cclet.2007.05.017Combs G. Double metal cyanide complex catalysts modified with group IIA compounds // Patent WO № 1999/048607. 1999.Huang Y.-J., Zhang X.-H., Hua Z.-J., Chen S.-L., Qi G.-R. Ring-opening polymerization of propylene oxide catalyzed by a calcium-chloride-modified zinc-cobalt double metal-cyanide complex // Macromol. Chem. Phys. 2010. V. 211. № 11. P. 1229-1237. https://doi.org/10.1002/macp.200900666Dexheimer E.M., Wildeson J., Hinz W. Method of synthesizing a double metal cyanide catalyst // Patent US № 6921737. 2005.Shaobo Z., Hui J., Zhihua Z. Polymetallic cyanide complex catalyst and preparation method and application thereof // Patent CN № 110684187. 2020.Jin H., Wang R., Zhang H., Tu J. Multi-metal cyanide complex catalyst // Patent CN № 101302286. 2010.Shaobo Z., Hui J., Zhihua Z. Supported metal cyanide complex catalyst as well as preparation method and application thereof // Patent CN № 113881032. 2022.Hofmann J., Ooms P., Gupta P., Schaefer W. Improved double metal cyanide catalysts for producing polyether polyols // Patent WO № 1999/046042. 1999.Le-Khac B. Highly active double metal cyanide catalysts // Patent US № 5482908. 1996.Le-Khac B. Polyether-containing double metal cyanide catalysts // Patent US № 5545601. 1996.Lee I.K., Ha J.Y., Cao C., Park D.-W., Ha C.-S., Kim I. Effect of complexing agents of double metal cyanide catalyst on the copolymerizations of cyclohexene oxide and carbon dioxide // Catal. Today. 2009. V. 148. № 3. P. 389-397. https://doi.org/10.1016/j.cattod.2009.07.073Kim I., Ahn J.-T., Ha C.S., Yang C.S., Park I. Polymerization of propylene oxide by using double metal cyanide catalysts and the application to polyurethane elastomer // Polymer. 2003. V. 44. № 11. P. 3417-3428. https://doi.org/10.1016/S0032-3861(03)00226-XYoon J.H., Lee I.K., Choi H.Y., Choi E.J., Yoon J.H., Shim S.E., Kim I. Double metal cyanide catalysts bearing lactate esters as eco-friendly complexing agents for the synthesis of highly pure polyols // Green Chem. 2011. V. 13. № 3. P. 631-639. https://doi.org/10.1039/C0GC00554AWei R.-J., Zhang X.-H., Du B.-Y., Fan Z.-Q., Qi G.-R. Highly active and selective binary catalyst system for the coupling reaction of CO2 and hydrous epoxides // J. Mol. Catal. A: Chem. 2013. V. 379. №. P. 38-45. https://doi.org/10.1016/j.molcata.2013.07.014Tran C.H., Pham L.T.T., Lee Y., Jang H.B., Kim S., Kim I. Mechanistic insights on Zn(II)-Co(III) double metal cyanide-catalyzed ring-opening polymerization of epoxides // J. Catal. 2019. V. 372. P. 86-102. https://doi.org/10.1016/j.jcat.2019.02.028Schaefer W., Hofmann J., Ooms P. Double metal cyanide catalysts for producing polyether polyols // WO Patent № 2003/020796. 2003.Mellado M.M., Gonzalez M.D.B. Double metal cyanide (DMC) catalysts with crown ethers, process to produce them and applications // Patent US № 2007/0135298. 2007.Zhang M., Yang Y., Chen L. Preparation of crown ether complexing highly active double metal cyanide catalysts and copolymerization of CO2 and propylene oxide // Chinese J. Catal. 2015. V. 36. № 8. P. 1304-1311. https://doi.org/10.1016/S1872-2067(15)60868-3Lili Y., Shaobo Z., Hui J., Wang W. Preparation method of aliphatic polycarbonate catalyzed by DMC catalyst // Patent CN № 104927040. 2015.Liu H., Wang X., Gu Y., Guo W. Preparation and characterization of double metal cyanide complex catalysts // Molecules. 2003. V. 8. № 1. P. 67-73. https://doi.org/10.3390/80100067Ooms P., Hofmann J., Gupta P., Groenendaal L. Double metal cyanide catalysts for preparing poly-etherpolyols // Patent US № 6204357. 2001.Hsu Y.-C., Tsai H.-C. High-activity double-metal-cyanide catalyst // Patent US № 2021/0205799. 2021.Ooms P., Hofmann J., Gupta P., Schaefer W. Double-metal-cyanide catalysts used for preparing polyether polyols // Patent US № 6391820. 2002.Hofmann J., Gupta P., Kumpf R.-J., Ooms P., Schaefer W., Schneider M. Crystalline double metal cyanide catalysts for producing polyether polyols // Patent WO № 1999/019063. 1999.Schaefer W., Hofmann J., Ooms P. Double metal cyanide catalysts for the production of polyetherpolyols // Patent WO № 2003/020422. 2003.Ooms P., Hofmann J., Dobler M. Double metal cyanide catalysts for the preparation of polyether polyols // Patent US № 2004/0092389. 2004.Le-Khac B. Double-metal cyanide catalysts for preparing polyether polyols // Patent US № 2003/0211935. 2003.Hofmann J., Ooms P., Gupta P., Schaefer W., Lohrenz J. Double metal cyanide catalysts for producing polyether polyols // Patent WO № 2000/047649. 2000.Chruściel A., Hreczuch W., Janik J., Czaja K., Dziubek K., Flisak Z., Swinarew A. Characterization of a double metal cyanide (DMC)-type catalyst in the polyoxypropylation process: effects of catalyst concentration // Ind. Eng. Chem. Res. 2014. V. 53. № 16. P. 6636-6646. https://doi.org/10.1021/ie500031jLe-Khac B. Double metal cyanide catalysts containing functionalized polymers // Patent WO № 1998/016310. 1998.Ooms P., Hofmann J., Gupta P. Bimetallic cyanide catalysts for producing polyether polyols // Patent WO № 2000/015337. 2000.Lee S.H., Lee I.K., Ha J.Y., Jo J.K., Park I., Ha C.-S., Suh H., Kim I. Tuning of the activity and induction period of the polymerization of propylene oxide catalyzed by double metal cyanide complexes bearing β-alkoxy alcohols as complexing agents // Ind. Eng. Chem. Res. 2010. V. 49. № 9. P. 4107-4116. https://doi.org/10.1021/ie1000967O'Connor J.M., Grieve R.L. Double metal cyanide catalysts containing polyglycol ether complexing agents // Patent US № 2001/0046940. 2001.Lim J., Yun S.H., Kim M.-R., Kim I. Synthesis of polycarbonate polyols by double-metal cyanide catalyzed copolymerization of epoxide with carbon dioxide // J. Nanosci. Nanotechnol. 2017. V. 17. № 10. P. 7507-7514. https://doi.org/10.1166/jnn.2017.14796Jang J.H., Ha J.H., Kim I., Baik J.H., Hong S.C. Facile room-temperature preparation of flexible polyurethane foams from carbon dioxide based poly(ether carbonate) polyols with a reduced generation of acetaldehyde // ACS Omega. 2019. V. 4. № 5. P. 7944-7952. https://doi.org/10.1021/acsomega.9b00808Lee D.H., Ha J.H., Kim I., Baik J.H., Hong S.C. Carbon dioxide based poly(ether carbonate) polyol in bi-polyol mixtures for rigid polyurethane foams // J. Polym. Environ. 2020. V. 28. № 4. P. 1160-1168. https://doi.org/10.1007/s10924-020-01668-0Jang E.H., Kim S.A., Kim H., Tran C.H., Song H.Y., Hyun K., Seo W.J., Kim I. Access to ultra-high molecular weight poly(propylene glycol)-based polyols using double metal cyanide catalyst // Macromol. Res. 2020. V. 28. № 1. P. 82-85. https://doi.org/10.1007/s13233-020-8008-1Tran C.-H., Lee, M.-W., Lee S.-J., Choi J.-H., Lee E.-G., Choi H.-K. Kim I. Highly active heterogeneous double metal cyanide catalysts for ring-opening polymerization of cyclic monomers // Polymers. 2022. V. 14. № 12. P. 2507. https://doi.org/10.3390/polym14122507He Z., Yu S., Cai Z., Cao X., Zhang L., Huang K. Modification of ZnCoPBA by different organic ligands and its application in the cycloaddition of CO2 and epoxides // J. Chem. Sci. 2022. V. 134. № 1. P. 35. https://doi.org/10.1007/s12039-022-02034-4Tran C.H., Kim S.A., Moon Y., Lee Y., Ryu H.M., Baik J.H., Hong S.C., Kim I. Effect of dicarbonyl complexing agents on double metal cyanide catalysts toward copolymerization of CO2 and propylene oxide // Catal. Today. 2021. V. 375, P. 335-342. https://doi.org/10.1016/j.cattod.2020.01.008Tran C.H., Pham L.T.T., Jang H.B., Kim S.A., Kim I. Effect of α-, β-, γ-, and δ-dicarbonyl complexing agents on the double metal cyanide-catalyzed ring-opening polymerization of propylene oxide // Catal. Today. 2021. V. 375, P. 429-440. https://doi.org/10.1016/j.cattod.2020.01.001Verma A., Saini S., Sharma B., Verma V., Behera B., Singh R., Ganguly S.K., Ray A., Vorontsov A., Kumar U. EDTA incorporated Fe-Zn double metal cyanide catalyst for the controlled synthesis of polyoxypropylene glycol // J. Polym. Res., 2023. V. 30. № 2. P. 62. https://doi.org/10.1007/s10965-022-03407-6Verma A., Sharma B., Saini S., Behera B., Saran S., Ganguly S.K., Kumar U. Oligomeric heterogeneous double metal cyanide catalyst for one-pot ring-opening polymerization // ChemistrySelect. 2023. V. 8. № 6. P. e202204760. https://doi.org/10.1002/slct.202204760Tran C.-H., Lee M.-W., Park S.-W., Jeong J.-E., Lee S.-J., Song W., Huh P., Kim I. Heterogeneous double metal cyanide catalyzed synthesis of poly(ε-caprolactone) polyols for the preparation of thermoplastic elastomers // Catalysts. 2021. V. 11. № 9. P. 1033. https://doi.org/10.3390/catal11091033Tran C.H., Lee S.J., Moon B.-r., Lee E.-g., Choi H.-k., Kim I. Organonitriles as complexing agents for the double metal cyanide-catalyzed synthesis of polyether, polyester, and polycarbonate polyols // Catal. Today. 2023. V. 418. P. 114125. https://doi.org/10.1016/j.cattod.2023.114125Tran C.H., Choi H.-K., Lee E.-G., Moon B.-R., Song W., Kim I. Prussian blue analogs as catalysts for the fixation of CO2 to glycidol to produce glycerol carbonate and multibranched polycarbonate polyols // J. CO2 Util. 2023. V. 74. P. 102530. https://doi.org/10.1016/j.jcou.2023.102530Kim I., Kim S.A. Double metal cyanide catalyst, preparation method therefor, and method for preparing polyol // Patent WO № 2021/137632. 2021.Luinstra G.A., Nörnberg B. Process for preparing double metal cyanide catalysts and their use in polymerization reactions // Patent WO № 2016/202838. 2016.Chen S., Qi G.-R., Hua Z.-J., Yan H.-Q. Double metal cyanide complex based on Zn3[Co(CN)6]2 as highly active catalyst for copolymerization of carbon dioxide and cyclohexene oxide // J. Polym. Sci., Part A: Polym. Chem. 2004. V. 42. № 20. P. 5284-5291. https://doi.org/10.1002/pola.20334Pinilla-de Dios M., Andrés-Iglesias C., Fernández A., Salmi T., Galdámez J.R., García-Serna J. Effect of Zn/Co initial preparation ratio in the activity of double metal cyanide catalysts for propylene oxide and CO2 copolymerization // Eur. Polym. J. 2017. V. 88. P. 280-291. https://doi.org/10.1016/j.eurpolymj.2017.01.028Ahmad S.-A., Le-Khac B., Bullano G.A. Double metal cyanide catalysts // Patent US № 5900384. 1999.Wu L.-C., Yu A.-F., Zhang M., Liu B.-H., Chen L.-B. DMC catalyzed epoxide polymerization: induction period, kinetics, and mechanism // J. Appl. Polym. Sci. 2004. V. 92. № 2. P. 1302-1309. https://doi.org/10.1002/aP.20089McDaniel K.G. High productivity alkoxylation processes // Patent US № 2008/0167501. 2008.Bachmann R., Klinger M., Jupke A. Molecular weight distribution in di metal cyanide catalyzed polymerization 1: fundamental distribution for length dependent propagation constant and segments // Macromol. Theory Simul. 2021. V. 30. № 5. P. 2100012. https://doi.org/10.1002/mats.202100012Klinger M., Bachmann R., Jupke A. Molecular weight distribution in di metal cyanide catalyzed polymerization 2: numerical simulation of chain activation/deactivation and diffusion effects // Macromol. Theory Simul. 2021. V. 30. № 5. P. 2100013. https://doi.org/10.1002/mats.202100013Langanke J., Hofmann J., Gürtler C., Wolf A. Facile synthesis of formaldehyde-based polyether(-carbonate) polyols // J. Polym. Sci., Part A: Polym. Chem. 2015. V. 53. № 18. P. 2071-2074. https://doi.org/10.1002/pola.27687Ma K., Bai Q., Zhang L., Liu B. Synthesis of flame-retarding oligo(carbonate-ether) diols via double metal cyanide complex-catalyzed copolymerization of PO and CO2 using bisphenol A as a chain transfer agent // RSC Adv. 2016. V. 6. № 54. P. 48405-48410. https://doi.org/10.1039/C6RA07325EZhang, X., Dong, J., Su, Y., Lee, E.G., Duan, Z., Kim, I., Liu, B. Construction and arm evolution of trifunctional phenolic initiator-mediated polycarbonate polyols produced by using a double metal cyanide catalyst // Polym. Chem. 2023. V. 14. № 11. P. 1263-1274. https://doi.org/10.1039/D3PY00009EMijolovic D., Haunert A., Kunst A., Bauer S., Miao Q., Eling B. // Раtent WO № 2009/095363. 2009.Kunst A., Eling B., Loeffler A., Lutter H.-D., Han W., Mueller J. Polyether polyols, process for preparing polyether polyols and their use for producing polyurethanes // Patent US № 2011/0269863. 2011.Hager S.L., Moore M.N., Reese J.R., Neal B.L. Polyols suitable for hot molded foam production with high renewable resource content // Patent US № 2013/0210951. 2013.Huang Y.-J., Qi G.-R., Wang Y.-H. Controlled ring-opening polymerization of propylene oxide catalyzed by double metal-cyanide complex // J. Polym. Sci., Part A: Polym. Chem. 2002. V. 40. № 8. P. 1142-1150. https://doi.org/10.1002/pola.10183Gao Y., Gu L., Qin Y., Wang X., Wang F. Dicarboxylic acid promoted immortal copolymerization for controllable synthesis of low-molecular weight oligo(carbonateether) diols with tunable carbonate unit content // J. Polym. Sci., Part A: Polym. Chem. 2012. V. 50. № 24. P. 5177-5184. https://doi.org/10.1002/pola.26366Liu S., Qin Y., Qiao L., Miao Y., Wang X., Wang F. Cheap and fast: oxalic acid initiated CO2-based polyols synthesized by a novel preactivation approach // Polym. Chem. 2016. V. 7. № 1. P. 146-152. https://doi.org/10.1039/C5PY01338KLiu S., Miao Y., Qiao L., Qin Y., Wang X., Chen X., Wang F. Controllable synthesis of a narrow polydispersity CO2-based oligo(carbonate-ether) tetraol // Polym. Chem. 2015. V. 6. № 43. P. 7580-7585. https://doi.org/10.1039/C5PY00556FLiu S., Qin Y., Chen X., Wang X., Wang F. One-pot controllable synthesis of oligo(carbonate-ether) triol using a Zn-Co-DMC catalyst: the special role of trimesic acid as an initiation-transfer agent // Polym. Chem. 2014. V. 5. № 21. P. 6171-6179. https://doi.org/10.1039/C4PY00578CLi X.-J., Wen Y.-F., Wang Y., Peng H.-Y., Zhou X.-P., Xie X.-L. CO2-based biodegradable supramolecular polymers with well-tunable adhesive properties // Chin. J. Polym. Sci. 2022. V. 40. № 1. P. 47-55. https://doi.org/10.1007/s10118-021-2641-9Haider K.W., Chung J.Y.J., Dormish J.F., Starcher R.V., Yano I.L., Hortelano E.R. Polyether-polysiloxane polyols // Patent US № 2008/0171829. 2008.Yi M.J., Byun S.-H., Ha C.-S., Park D.-W., Kim I. Copolymerization of cyclohexene oxide with carbon dioxide over nano-sized multi-metal cyanide catalysts // Solid State Ion. 2004. V. 172. № 1. P. 139-144. https://doi.org/10.1016/j.ssi.2004.04.031Friščić T., Mottillo C., Titi H.M. Mechanochemistry for Synthesis // Angew. Chem. Int. Ed. 2020. V. 59. № 3. P. 1018-1029. https://doi.org/10.1002/anie.201906755Guo Z., Lin Q. Coupling reaction of CO2 and propylene oxide catalyzed by DMC with co-complexing agents incorporated via ball milling // J. Mol. Catal. A: Chem. 2014. V. 390. P. 63-68. https://doi.org/10.1016/j.molcata.2014.03.006Guo Z., Lin Q., Wang X., Yu C., Zhao J., Shao Y., Peng T. Rapid synthesis of nanoscale double metal cyanide catalysts by ball milling for the cycloaddition of CO2 and propylene oxide // Mater. Lett. 2014. V. 124. P. 184-187. https://doi.org/10.1016/j.matlet.2014.03.076Guo Z., Lin Q., Zhu L., Wang X., Niu Y., Yu C., Fang T. Nanolamellar Zn-Ni/Co-Ni catalysts introduced by ball milling for the copolymerization of CO2 with propylene oxide // Nanosci. Nanotechnol. Lett. 2014. V. 6. № 4. P. 353-356. https://doi.org/10.1166/nnl.2014.1757Zhang W., Lu L., Cheng Y., Xu N., Pan L., Lin Q., Wang Y. Clean and rapid synthesis of double metal cyanide complexes using mechanochemistry // Green Chem. 2011. V. 13. № 10. P. 2701-2703. https://doi.org/10.1039/C1GC15557AQiang L., Zhifang G., Lisha P., Xue X. Zn-Cr double metal cyanide catalysts synthesized by ball milling for the copolymerization of CO2/propylene oxide, phthalic anhydride/propylene oxide, and CO2/propylene oxide/phthalic anhydride // Catal. Commun. 2015. V. 64. P. 114-118. https://doi.org/10.1016/j.catcom.2015.02.015Shi J., Shi Z., Yan H., Wang X., Zhang X., Lin Q., Zhu L. Synthesis of Zn-Fe double metal cyanide complexes with imidazolium-based ionic liquid cocatalysts via ball milling for copolymerization of CO2 and propylene oxide // RSC Adv. 2018. V. 8. № 12. P. 6565-6571. https://doi.org/10.1039/C7RA12528CLiu N., Gu C., Wang Q., Zhu L., Yan H., Lin Q. Fabrication and characterization of the ternary composite catalyst system of ZnGA/RET/DMC for the terpolymerization of CO2, propylene oxide and trimellitic anhydride // RSC Adv. 2021. V. 11. № 15, P. 8782-8792. https://doi.org/10.1039/D0RA09630JKim I., Anas K., Lee S., Ha, C.-S., Park, D.-W. Tuning of the activity and induction period of double metal cyanide catalyzed ring-opening polymerizations of propylene oxide by using ionic liquids // Catal. Today. 2008. V. 131. № 1. P. 541-547. https://doi.org/10.1016/j.cattod.2007.10.067Tharun J., Dharman M.M., Hwang Y., Roshan R., Park M.S., Park D.-W. Tuning double metal cyanide catalysts with complexing agents for the selective production of cyclic carbonates over polycarbonates // Appl. Catal. A: Gen. 2012. V. 419-420. P. 178-184. https://doi.org/10.1016/j.apcata.2012.01.024Wei R.-j., Zhang X.-h., Du B.-y., Fan Z.-q., Qi G.-r. Synthesis of bis(cyclic carbonate) and propylene carbonate via a one-pot coupling reaction of CO2, bisepoxide and propylene oxide // RSC Adv. 2013. V. 3. № 38. P. 17307-17313. https://doi.org/10.1039/C3RA42570CDharman M.M., Yu J.-I., Ahn J.-Y., Park D.-W. Selective production of cyclic carbonate over polycarbonate using a double metal cyanide-quaternary ammonium salt catalyst system // Green Chem. 2009. V. 11. № 11. P. 1754-1757. https://doi.org/10.1039/B916875NZhang Y.-Y., Li Y., Zhou X.-J., Zhang X.-H., Du B.-Y., Fan Z.-Q. Synthesis of an amphiphilic brush copolymer by a highly efficient "grafting onto" approach via CO2 chemistry // Macromol. Rapid Commun. 2015. V. 36. № 9. P. 852-857. https://doi.org/10.1002/marc.201400718Liu B., Zhang Y.-Y., Zhang X.-H., Du B.-Y., Fan Z.-Q. Fixation of carbon dioxide concurrently or in tandem with free radical polymerization for highly transparent polyacrylates with specific UV absorption // Polym. Chem. 2016. V. 7. № 22. P. 3731-3739. https://doi.org/10.1039/C6PY00525JGarcia J.L., Jang E.J., Alper H. New heterogeneous catalysis for the synthesis of poly(ether polyol)s // J. Appl. Polym. Sci. 2002. V. 86. № 7. P. 1553-1557. https://doi.org/10.1002/aP.10996Robertson N.J., Qin Z., Dallinger G.C., Lobkovsky E.B., Lee S., Coates, G.W. Two-dimensional double metal cyanide complexes: highly active catalysts for the homopolymerization of propylene oxide and copolymerization of propylene oxide and carbon dioxide // Dalton Trans. 2006. № 45. P. 5390-5395. https://doi.org/10.1039/B607963FHofmann J. Double metal cyanide catalysts for the preparation of polyether polyols // Patent US № 2008/0177025. 2008.Yu S.J., Liu Y., Byeon S.J., Park D.W., Kim I. Ring-opening polymerization of propylene oxide by double metal cyanide catalysts prepared by reacting CoCl2 with various metal cyanide salts // Catal. Today. 2014. V. 232. P. 75-81. https://doi.org/10.1016/j.cattod.2013.09.038Alferov K., Wang S., Li T., Xiao M., Guan S., Meng Y. Co-Ni cyanide bi-metal catalysts: copolymerization of carbon dioxide with propylene oxide and chain transfer agents // Catalysts. 2019. V. 9. № 8. P. 632. https://doi.org/10.3390/catal9080632Chen S., Xiao Z., Ma M. Copolymerization of carbon dioxide and epoxides with a novel effective Zn-Ni double-metal cyanide complex // J. Appl. Polym. Sci. 2008. V. 107. № 6. P. 3871-3877. https://doi.org/10.1002/app.25064Lawniczak-Jablonska K., Dynowska E., Lisowski W., Sobczak J.W., Chruściel A., Hreczuch W., Libera J., Reszka A. Structural properties and chemical bonds in double metal cyanide catalysts // X-ray Spectrom. 2015. V. 44. № 5. P. 330-338. https://doi.org/10.1002/xrs.2636Mullica D.F., Milligan W.O., Beall G.W., Reeves W.L. Crystal structure of Zn3[Co(CN)6]2·12H2O // Acta Crystallogr. B. 1978. V. 34. № 12. P. 3558-3561. https://doi.org/10.1107/S0567740878011589Simonov A., De Baerdemaeker T., Boström H.L.B., Ríos Gómez M.L., Gray H.J., Chernyshov D., Bosak A., Bürgi H.-B., Goodwin A.L. Hidden diversity of vacancy networks in Prussian blue analogues // Nature. 2020. V. 578. № 7794. P. 256-260. https://doi.org/10.1038/s41586-020-1980-yZhang X.-H., Hua Z.-J., Chen S., Liu, F., Sun X.-K., Qi G.-R. Role of zinc chloride and complexing agents in highly active double metal cyanide catalysts for ring-opening polymerization of propylene oxide // Appl. Catal. A: Gen. 2007. V. 325. № 1. P. 91-98. https://doi.org/10.1016/j.apcata.2007.03.014Chen S., Zhang P., Chen L. Fe/Zn double metal cyanide (DMC) catalyzed ring-opening polymerization of propylene oxide: Part 3. Synthesis of DMC catalysts // Prog. Org. Coat. 2004. V. 50. № 4. P. 269-272. https://doi.org/10.1016/j.porgcoat.2004.03.003Lawniczak-Jablonska K., Chrusciel A. Estimation of the catalytic centre in double metal cyanide catalysts by XAS // J. Phys. Conf. Ser. 2016. V. 712. № 1. P. 012062. https://doi.org/10.1088/1742-6596/712/1/012062Chruściel A., Hreczuch W., Czaja K., Ławniczak-Jabłońska K., Janik J. The complementary structural studies of the double metal cyanide type catalysts for the ring opening polymerization of the oxiranes // Polimery. 2016. V. 61. № 6. P. 421-432. https://doi.org/10.14314/polimery.2016.421Sreeprasanth P.S., Srivastava R., Srinivas D., Ratnasamy P. Hydrophobic, solid acid catalysts for production of biofuels and lubricants // Appl. Catal. A: Gen. 2006. V. 314. № 2. P. 148-159. https://doi.org/10.1016/j.apcata.2006.08.012Marquez C., Simonov A., Wharmby M.T., Van Goethem C., Vankelecom I., Bueken B., Krajnc A., Mali G., De Vos, D., De Baerdemaeker T. Layered Zn2[Co(CN)6](CH3COO) double metal cyanide: a two-dimensional DMC phase with excellent catalytic performance // Chem. Sci. 2019. V. 10. № 18. P. 4868-4875. https://doi.org/10.1039/C9SC00527GSebastian J., Darbha S. Structure-induced catalytic activity of Co-Zn double-metal cyanide complexes for terpolymerization of propylene oxide, cyclohexene oxide and CO2 // RSC Adv. 2015. V. 5. № 24. P. 18196-18203. https://doi.org/10.1039/C5RA00299KSebastian J., Srinivas D. Factors influencing catalytic activity of Co-Zn double-metal cyanide complexes for alternating polymerization of epoxides and CO2 // Appl. Catal. A: Gen. 2015. V. 506. P. 163-172. https://doi.org/10.1016/j.apcata.2015.09.010Wojdeł J.C., Bromley S.T., Illas F., Jansen J.C. Development of realistic models for double metal cyanide catalyst active sites // J. Mol. Model. 2007. V. 13. № 6. P. 751-756. https://doi.org/10.1007/s00894-007-0218-3Almora-Barrios N., Pogodin S., Bellarosa L., García-Melchor M., Revilla-López G., García-Ratés, M., Vázquez-García A.B., Hernández-Ariznavarreta P., López N. Structure, activity, and deactivation mechanisms in double metal cyanide catalysts for the production of polyols // ChemCatChem. 2015. V. 7. № 6. P. 928-935. https://doi.org/10.1002/cctc.201402907Chruściel A., Hreczuch W., Czaja K., Sacher-Majewska B. On thermal behaviour of DMC catalysts for ring opening polymerization of epoxides // Thermochim. Acta. 2016. V. 630. P. 78-89. https://doi.org/10.1016/j.tca.2016.02.009Barnard J.A. The pyrolysis of tert-butanol // Trans. Faraday Soc. 1959. V. 55. P. 947-951. https://doi.org/10.1039/TF9595500947Kisielowski C., Specht P., Rozeveld S., Freitag B., Kieft E.R., Kang J., Fielitz A.J., Fielitz T.R., van Dyck D., Yancey D.F. Exploring functional materials by understanding beam-sample interactions // Adv. Funct. Mater. 2022. V. 32. № 27. P. 2201112. https://doi.org/10.1002/adfm.202201112Hayes J.E., Langsdorf L.J., Isaacs B.H., Armellini F.J. Process for rapid activation of double metal cyanide catalysts // Patent US № 5844070. 1998.Schenk S., Notni J., Köhn U., Wermann K., Anders E. Carbon dioxide and related heterocumulenes at zinc and lithium cations: bioinspired reactions and principles // Dalton Trans. 2006. № 35. P. 4191-4206. https://doi.org/10.1039/B608534BLi Y., Zhang Y.-Y., Liu B., Zhang X.-H. HCAII-inspired catalysts for making carbon dioxide-based copolymers: the role of metal-hydroxide bond // Chin. J. Polym. Sci. 2018. V. 36. № 2. P. 139-148. https://doi.org/10.1007/s10118-018-2047-5Kuyper J., Boxhoorn G. Hexacyanometallate salts used as alkene-oxide polymerization catalysts and molecular sieves // J. Catal. 1987. V. 105. № 1. P. 163-174. https://doi.org/10.1016/0021-9517(87)90016-9Chen S., Xu N., Shi J. Structure and properties of polyether polyols catalyzed by Fe/Zn double metal cyanide complex catalyst // Prog. Org. Coat. 2004. V. 49. № 2. P. 125-129. https://doi.org/10.1016/j.porgcoat.2003.08.021Chen S., Chen L. Sequence structure of polyether catalyzed by Fe-Zn double-metal cyanide complex catalysts // Colloid. Polym. Sci. 2003. V. 281. № 3. P. 288-291. https://doi.org/10.1007/s00396-002-0792-yLuinstra G.A., Molnar F. Poly(propylene carbonate), old CO2 copolymer with new attractiveness // Macromol. Symp. 2007. V. 259. № 1. P. 203-209. https://doi.org/10.1002/masy.200751324Klaus S., Lehenmeier M.W., Herdtweck E., Deglmann P., Ott A.K., Rieger B. Mechanistic insights into heterogeneous zinc dicarboxylates and theoretical considerations for CO2-epoxide copolymerization // J. Am. Chem. Soc. 2011. V. 133. № 33. P. 13151-13161. https://doi.org/10.1021/ja204481wStahl S.-F., Luinstra G.A. DMC-Mediated copolymerization of CO2 and PO - mechanistic aspects derived from feed and polymer composition // Catalysts. 2020. V. 10. № 9. P. 1066. https://doi.org/10.3390/catal10091066Darensbourg D.J., Adams M.J., Yarbrough J.C. Toward the design of double metal cyanides for the copolymerization of CO2 and epoxides // Inorg. Chem. 2001. V. 40. № 26. P. 6543-6544. https://doi.org/10.1021/ic0155941Darensbourg D.J., Adams M.J., Yarbrough J.C., Phelps A.L. Synthesis and structural characterization of double metal cyanides of iron and zinc: catalyst precursors for the copolymerization of carbon dioxide and epoxides // Inorg. Chem. 2003. V. 42. № 24. P. 7809-7818. https://doi.org/10.1021/ic0347900Darensbourg D.J., Phelps A.L. Mixed metal cyanide complexes derived from the CpCo(CN)3- anion // Inorg. Chim. Acta. 2004. V. 357. № 5. P. 1603-1607. https://doi.org/10.1016/j.ica.2003.11.016Kubisa P., Penczek S. Cationic activated monomer polymerization of heterocyclic monomers // Prog. Polym. Sci. 1999. V. 24. № 10. P. 1409-1437. https://doi.org/10.1016/S0079-6700(99)00028-3Raghuraman A., Babb D., Miller M., Paradkar M., Smith B., Nguyen A. Sequential DMC/FAB-catalyzed alkoxylation toward high primary hydroxyl, high molecular weight polyether polyols // Macromolecules. 2016. V. 49. № 18. P. 6790-6798. https://doi.org/10.1021/acs.macromol.6b01363Inoue S. Immortal polymerization: the outset, development, and application // J. Polym. Sci., Part A: Polym. Chem. 2000. V. 38. № 16. P. 2861-2871. https://doi.org/10.1002/1099-0518(20000815)38:16<2861::AIDPOLA20>3.0.CO;2-1Zhang M., Villa C., Thompson L., Weston J. Multisite model of polyol preparation in continuous processes using heterogeneous double metal cyanide catalysts. https://folk.ntnu.no/skoge/prost/proceedings/aiche-2004/pdffiles/papers/353b.pdf.Grajciar L., Heard C.J., Bondarenko A.A., Polynski M.V., Meeprasert J., Pidko E.A., Nachtigall P. Towards operando computational modeling in heterogeneous catalysis // Chem. Soc. Rev. 2018. V. 47. № 22. P. 8307-8348. https://doi.org/10.1039/C8CS00398JNatta G., Mantica E. The distribution of products in a series of consecutive competitive reactions // J. Am. Chem. Soc. 1952. V. 74. № 12. P. 3152-3156. https://doi.org/10.1021/ja01132a057Stahl S.-F., Wietzer M., Luinstra G.A. DMC-mediated propoxylation in semibatch with an external loop: insights into the catalytic action // Ind. Eng. Chem. Res. 2023. V. 62. № 29. P. 11536-11548. https://doi.org/10.1021/acs.iecr.3c01313Lee S., Baek S.T., Anas K., Ha C.-S., Park D.-W., Lee J.W., Kim I. Tuning of activity, induction period and polymer properties of double metal cyanide catalyzed ring-opening polymerizations of propylene oxide by using quaternary ammonium salts // Polymer. 2007. V. 48. № 15. P. 4361-4367. https://doi.org/10.1016/j.polymer.2007.05.072Lee S.H., Ha C.-S., Kim I. Modified montmorillonite as a tuner of propylene oxide polymerization behavior catalyzed by double metal cyanide compound // Macromol. Res. 2007. V. 15. № 3. P. 202-204. https://doi.org/10.1007/BF03218775Le-Khac B., Wang W., Faraj M.K. Acid-treated double metal cyanide complex catalysts // Patent US № 6063897. 2000.Safina L.R., Kharlampidi K.E., Safin D.K. Molecular-weight characteristics and deemulsifying activity of oligourethanes based on alkylene oxide block copolymers and propylene oxide homopolymers prepared in the presence of a double metal cyanide catalyst // Russ. J. Appl. Chem. 2012. V. 85. № 10. P. 1610-1616. https://doi.org/10.1134/S1070427212100230Dai C., Zhu Q., Pang H., Zhu L., Lin Q. Rapid copolymerization of carbon dioxide and propylene oxide catalyzed by double metal cyanide complexes in an ultrasonic field // Mater. Lett. 2016. V. 180. P. 89-92. https://doi.org/10.1016/j.matlet.2016.05.119Lear J.J., Sloan O.D., Pazos J.F. Method for decreasing the propensity for phase-out of the high molecular weight component of double metal cyanide-catalyzed high secondary hydroxyl polyoxypropylene polyols // Patent US № 6083420. 2000.Laitar D.S., Babb D.A., Villa C.M., Keaton R., Masy J.-P. Alkylene oxide polymerization using a double metal cyanide catalyst complex and a magnesium, Group 3-Group 15 metal or lanthanide series metal compound // Patent US № 9040657. 2015.McDaniel K.G., Combs G.G. Catalyst for the production of polyols having lower amounts of high molecular weight tail // Patent US № 9562134. 2017.Eleveld M.B., Grotenbreg R.A.W., Van Kempen R. Preparation of a double metal cyanide catalyst // Patent US № 6977236. 2005.Song Z., Subramaniam B., Chaudhari R.V. Transesterification of propylene carbonate with methanol using Fe-Mn double metal cyanide catalyst // ACS Sustain. Chem. Eng. 2019. V. 7. № 6. P. 5698-5710. https://doi.org/10.1021/acssuschemeng.8b04779Hamuyuni J., Daramola M.O., Oluwasina O.O. Energy-Dispersive X-ray Spectroscopy: Theory and Application in Engineering and Science in Encyclopedia of Physical Organic Chemistry / Eds. Wang. Z. John Wiley & Sons, 2017. P. 1-23.Jadhav A.R., Bandal H.A., Kim H. Synthesis of substituted amines: catalytic reductive amination of carbonyl compounds using Lewis acid Zn-Co-double metal cyanide/polymethylhydrosiloxane // Chem. Eng. J. 2016. V. 295. P. 376-383. https://doi.org/10.1016/j.cej.2016.02.067Kotwal M., Deshpande S.S., Srinivas D. Esterification of fatty acids with glycerol over Fe-Zn doublemetal cyanide catalyst // Catal. Commun. 2011. V. 12. № 14. P. 1302-1306. https://doi.org/10.1016/j.catcom.2011.05.008Kumar P., Matoh L., Srivastava V.C., Štangar U.L. Synthesis of zinc/ferrocyanide nano-composite catalysts having a high activity for transesterification reaction // Renew. Energy. 2020. V. 148. P. 946-952. https://doi.org/10.1016/j.renene.2019.10.178Kumar P., Srivastava V.C., Jha M.K. Synthesis of biodiesel from transesterification of Jatropha oil with methanol using double metal cyanide as catalyst // J. Clean Energy Technol. 2017. V. 5. № 1. P. 23-26. https://doi.org/10.18178/jocet.2017.5.1.337Sebastian J., Darbha S. Solid, double-metal cyanide catalysts for synthesis of hyperbranched polyesters and aliphatic polycarbonates // J. Chem. Sci. 2014. V. 126. № 2. P. 499-509. https://doi.org/10.1007/s12039-014-0573-4Sebastian J., Srinivas D. Influence of method of preparation of solid, double-metal cyanide complexes on their catalytic activity for synthesis of hyperbranched polymers // Appl. Catal. A: Gen. 2013. V. 464-465. P. 51-60. https://doi.org/10.1016/j.apcata.2013.05.024Srinivas D., Satyarthi J.K. Biodiesel production from vegetable oils and animal fat over solid acid double-metal cyanide catalysts // Catal. Surv. from Asia. 2011. V. 15. № 3. P. 145-160. https://doi.org/10.1007/s10563-010-9108-2Srivastava R., Srinivas D., Ratnasamy P. Fe-Zn double-metal cyanide complexes as novel, solid transesterification catalysts // J. Catal. 2006. V. 241. № 1. P. 34-44. https://doi.org/10.1016/j.jcat.2006.04.002Marquez C., Corbet M., Smolders S., Marion P., De Vos D. Double metal cyanides as heterogeneous Lewis acid catalysts for nitrile synthesis via acid-nitrile exchange reactions // Chem. Commun. 2019. V. 55. № 86. P. 12984-12987. https://doi.org/10.1039/C9CC05382DSatyarthi J.K., Radhakrishnan S., Srinivas D. Factors influencing the kinetics of esterification of fatty acids over solid acid catalysts // Energy & Fuels. 2011. V. 25. № 9. P. 4106-4112. https://doi.org/10.1021/ef2009138Satyarthi J.K., Srinivas D., Ratnasamy P. Influence of surface hydrophobicity on the esterification of fatty acids over solid catalysts // Energy & Fuels. 2010. V. 24. № 3. P. 2154-2161. https://doi.org/10.1021/ef1001452Satyarthi J.K., Srinivas D., Ratnasamy P. Hydrolysis of vegetable oils and fats to fatty acids over solid acid catalysts // Appl. Catal. A: Gen. 2011. V. 391. № 1. P. 427-435. https://doi.org/10.1016/j.apcata.2010.03.047De Gisi S., Lofrano G., Grassi M., Notarnicola M. Characteristics and adsorption capacities of low-cost sorbents for wastewater treatment: a review // Sustain. Mater. Technol. 2016. V. 9. P. 10-40. https://doi.org/10.1016/j.susmat.2016.06.002Luo M., Zhang X.-H., Du B.-Y., Wang Q., Fan Z.-Q. Alternating copolymerization of carbonyl sulfide and cyclohexene oxide catalyzed by zinc-cobalt double metal cyanide complex // Polymer. 2014. V. 55. № 16. P. 3688-3695. https://doi.org/10.1016/j.polymer.2014.05.065Wei R.-J., Zhang X.-H., Du B.-Y., Sun X.-K., Fan Z.-Q., Qi G.-R. Highly Regioselective and alternating copolymerization of racemic styrene oxide and carbon dioxide via heterogeneous double metal cyanide complex catalyst // Macromolecules. 2013. V. 46. № 9. P. 3693-3697. https://doi.org/10.1021/ma4004709Yan F., Yuan Z., Lu P., Luo W., Yang L., Deng L. Fe-Zn double-metal cyanide complexes catalyzed biodiesel production from high-acid-value oil // Renew. Energy. 2011. V. 36. № 7. P. 2026-2031. https://doi.org/10.1016/j.renene.2010.10.032Cao X., Wang K., Mao Q., Gu Z., Wang F. MCM-41-supported double metal cyanide nanocomposite catalyst for ring-opening polymerisation of propylene oxide // J. Nanopart. Res. 2022. V. 24. № 3. P. 71-71. https://doi.org/10.1007/s11051-022-05443-1Dienes Y., Leitner W., Müller M.G.J., Offermans W.K., Reier T., Reinholdt A., Weirich T.E., Müller T.E. Hybrid sol-gel double metal cyanide catalysts for the copolymerisation of styrene oxide and CO2 // Green Chem. 2012. V. 14. № 4. P. 1168-1177. https://doi.org/10.1039/C2GC16485JMarquez C., Rivera-Torrente M., Paalanen P.P., Weckhuysen B.M., Cirujano F.G., De Vos D., De Baerdemaeker T. Increasing the availability of active sites in Zn-Co double metal cyanides by dispersion onto a SiO2 support // J. Catal. 2017. V. 354. P. 92-99. https://doi.org/10.1016/j.jcat.2017.08.008Sun X.-K., Zhang X.-H., Liu F., Chen S., Du B.-Y., Wang Q., Fan Z.-Q., Qi G.-R. Alternating copolymerization of carbon dioxide and cyclohexene oxide catalyzed by silicon dioxide/Zn-CoIII double metal cyanide complex hybrid catalysts with a nanolamellar structure // J. Polym. Sci., Part A: Polym. Chem. 2008. V. 46. № 9. P. 3128-3139. https://doi.org/10.1002/pola.22666Zhu L., Zhu Q., Wang Q., Gu C., Tang A., Liu T., Dai C., Li H. CO2 copolymerization catalyzed by the double metal cyanide catalysts Zn-Fe(III)/Zn-Co(III) with nanometer-sized γ-Al2O3 as co-catalyst // Nanosci. Nanotechnol. Lett. 2018. V. 10. № 11. P. 1515-1522. https://doi.org/10.1166/nnl.2018.2822Le-Khac B. Polyurethane foam-supported double metal cyanide catalysts for polyol synthesis // Patent US № 5426081. 1995.Le-Khac B. Plastic foam-supported double metal cyanide catalysts for polyether polyol synthesis // Patent US № 5523386. 1996.Le-Khac B. Polyurethane foam-supported double metal cyanide catalysts for polyether polyol synthesis // Patent US № 5527880. 1996.Zhang X.-H., Wei R.-J., Sun X.-K., Zhang J.-F., Du B.-Y., Fan Z.-Q., Qi G.-R. Selective copolymerization of carbon dioxide with propylene oxide catalyzed by a nanolamellar double metal cyanide complex catalyst at low polymerization temperatures // Polymer. 2011. V. 52. № 24. P. 5494-5502. https://doi.org/10.1016/j.polymer.2011.09.040