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science • technique 198 • The propertiesoflimoneneandthemethodsitsobtaining atmospheric pressure). and 120°C to up (temperatures conditions mild at out carried are by-products can be easily developed. organicLimonene oxidation other processes and water, is peroxide hydrogen of transformation Ti-SBA-15. In this method, the only by-product and connected with ofthe Ti-MCM-41 as: presence such the materials, silicate in titanium mesoporous and various wt% in 60 peroxide, with hydrogen limonene of oxidation by limonene of derivatives oxygenated obtain to allows which technology “green” modern, Technologyof theUniversity on studies performed are Szczecin in Pomeranian Technology, West Chemical Organic of Institute the Now,atlimonene. of conversion high a at limonene of derivatives oxygenated appropriate the oxidizing of yields as high obtain TBHP to allow or agents peroxide hydrogen The used obtained. which are methods compound this of derivatives oxygenated of mixtures multicomponent the processes these in but limonene of derivativesoxygenated of formation the cause can microorganisms hydroperoxide t-butyl selected the utilization the (TBHP, or Also decane). in solution M solutions) 5-6 water wt% peroxide 60 hydrogen or as wt% (30 such agents oxidizing different using out for limonene, example perillyl of alcohol. allow Limonene derivatives oxidation process can oxygenated be It carried valuable processes. very obtain oxidation to environment. easily the very to undergoes harmful Limonene very are methods this moreover water, of waste quantities significant generate and temperatures with a small amount of toxic waste. Pyrolytic methods require high limonene pure almost obtain and industry food the from derived peels) allow to recycle the waste citrus peels ordistillation (simply methods Natural processes. pyrolytic of help with example for methods, synthetic and natural the by obtained be can It (biomass). peels citrus waste from obtained oils essential of component main the is industry.It chemical the in applications Introduction colon andbreast. of cancer the growth the inhibits which alcohol, perillyl example: a valuable raw material for the obtaining of valuable derivatives, for is peels the from extracted Limonene management. its for in the cyclic ring (Fig. 1). Moreover, in nature it occurs often in the in often occurs Moreover,it 1). nature (Fig. in ring cyclic the in thanks to the presence of chiral center on the fourth atom of carbon – two of form the in nature in occurs Limonene limonene). (S-(-)- smell or (R-(+)-limonene) smell citrus characteristic a with and g/mol 136.23 of mass molar a with liquid yellow pale or Dr hab.inż.AgnieszkaWRÓBLEWSKA,prof. [email protected] Corresponding author: colourless a is (4-isopropenyl-1-methylcyclohexene) Limonene many has which compound a is Limonene methods key the of one are processes oxidation Limonene Please citeas:CHEMIK2016,70,4,193–202 West Pomeranian UniversityofTechnology, Szczecin,Poland Technology, Chemical of Organic – Institute WRÓBLEWSKA* MALKO, Agnieszka Władysław Mariusz for organicsynthesesandindustry The importanceofR-(+)-limoneneastherawmaterial content of the ingredients and the ripening time affect significantly the into account the content of fruit acids, sugar and taking pigment. The important different is gathered are fruits which in time The properties. different have fruits collected the months, five about for last can time the in planted are which fruit oranges countries whichsuppliercitrusfruits: of types major the of list a presented is Below limonene. of 95% containing oil citrus including - fruityellowtype:,,limettaandgrapefruit. - fruitsoforangtype:sweetorange,bitterorangeandtangerine, Types offruitcanbeclassifiedasfollows: the citrus depends mainly on the type of the fruit and its structure [2]. from obtained juice the of quality The production. this during waste of minimization the with connected issues become have great importance the time, same the at and, obtaining juices this of methods of and the still growing demand for the juices resulted in the development acetone andbenzene[1]. g/dm 0.94 of density the -80°C, temperature melting the mmHg), 760 (at 176°C temperature boiling the properties: following the by characterized is it and lime, and lemon , orange, sweet of the citrus juices production started in 40 in started production juices citrus the of flourishing The people. by juices citrus consumption and production a has scale industrial an on limonene of production greatest the for importance The kg. 50–75 achieves limonene of production annual Its 95%). reaches purity its method this (in peels citrus waste the from distillation vapor the by or 96–97%) of the purity the by characterized is from (it layer oranges fruit whole organic the from obtained the was which of juice squeezed separation R-(+)-limonene the scale by laboratory manufactured the is On peels. fruits citrus the in ie apiain ad perne xiis R-(+)-limonene. exhibits appearance and applications wider limonene of isomers two these From mixture. racemic a of form Because citrus fruits are growing the whole year and their ripening • Spain/Morocco:Navel,Valencia, Jaffa. • Italy:BiondoComune,Ovale, Navel, Valencia,• USA: JaffaandPineapple, • Brazil:HamlinandPera, juices, of production the in material raw basic the are Oranges R-(+)-limonene occurs in the peels of citrus fruits, such as: such fruits, citrus of peels the in occurs R-(+)-limonene -+-ioee s mjr opnn o esnil is found oils essential of component major a is R-(+)-limonene 3 and a good in methanol and as well as in as well as ethanol and methanol in solubility good a and Fig. 1. Theisomersoflimonene nr 4/2016 •tom 70 th years of the 20 the of years th century, this oilisR(+)-limonene. glands, which collect the essential – the main component of final product. Figure 2 shows a cross section of the orange fruit and the which arecontained inthisoil. waxes oil essential the from separate to allows It applied. is freezing of step the also peels orange the from oil essential the obtaining the of process the of variations some In tanks. in stored is product pure The processed. are they which on way the and fruit the of type the on depends water in oil essential the of amount the but material, used raw the of kg 100 the on oil essential the of kg 2–5 about contains water This extraction. of stage first the to recycled is process this of of the fruit and parts of skin. Water, which is used in the several stages seeds sand, as: such parts, solid of cleared it then and separators, and the orange oil is separated from the water layer using the hydrocyclone 70–90 wt% of the from the orange peels. In the next stages and directed into the tank. The resulting emulsion of O/W type contains shakers in water with washed type then is emulsion This emulsion obtained. is O/W of form the in oil orange the way this In water. with order extracted then is oil resulting The oil. orange in the them from obtain to pressed and fragmented are fruits the of peels later them, from squeezed is juice the and of cut are they first extractor,where Westfalia schema whichisshownonFigure3. GEA The industry.the to according oil orange the food of production the proposes company the from the with waste scale the industrial the utilization on and laboratory the on production a largeamountofjuice,whichisholdbygluelikesubstances. containing segments into divided radiate is flesh fruit The pectin’s. of amount high contains that layer dense white, a is It . the of part inside the is Albedo wax. natural a by microorganisms against also and The external layer of the orange fruit is protected against loss of water fruits is responsible the aroma oil which is collected oils in the oil glands. peel the in presence the with connected is fruit the of color The glands. oil contains which layer thin relatively external pigmented, a The is [2]. peel the albedo of layer and peel the of layer external the layers: codn t te iue te rne ris r sre t the to served are fruits orange the 2 Figure the to According limonene of methods many presented are there literature the In two of composed is pericarp, as known also peel, orange The Fig. 2.Thecrosssectionoftheorangefruitandoilglands Fig. 3.Thetechnologicalschemeoftheorangeoilproduction - (orange pigment). For the special smell of the orange the of smell special the For pigment). (orange β-carotene proposed byGEAWestfalia company[2] nr 4/2016 •tom 70 f hs cmons belong: compounds these of To[9]. industry or in also and medicine, group the in example for used are which compounds, active biologically many of fact that this compound has a carbon skeleton similar to the construction biodegradable polymers. and “fragrant” example for production in monomer valuable the it production polymers In cellulite. relaxing against fight the to and in massages, used also is R-(+)-limonene fresheners). air and as the fragrant component of the household chemicals (detergents, ability to degrease its various to surfaces. due Limonene equipment found electronic also for utilizations cleaner a as used be also can compoundThis reactions. oxidation in the be not can it so utilization of limonene the in with biodegradable, organic connected disadvantage syntheses cheap, main is The a its compound. toxic easiness is low to it oxidation, because syntheses organic the for chemistry and the organic industry, and also as an alternative solvent organic the for intermediates useful many of syntheses the in used because it has antibacterial and disinfecting properties. Limonene is [8]®) (Herbromix poultry for feeds of component the as also and This compound is also used in agriculture [7].as stabilizer an a ecological and insecticidecompound fragrant a of role a plays limonene as: such corporations, large Coca–Cola Company, in fruit juices, ice creams and sweets, where by produced are which beverages carbonated in present also R-(+)-limoneneis 4. Figure – food) for perfume industry, in the food industry ( and fragrant additives the in system), medicinenervous the natural stabilizing and harmonizing the (relaxing, in aromatherapy the including – medicine Limonene –thecompoundwithmanyapplications contains 20–25wt%oftheracemicmixturelimonene[6]. usually which fraction paraffin the and 200°C below point boiling the withfraction gasoline the of wt% 20–25 contains usually oil This oil. fuel of wt% 55 about obtain to allows tires waste of pyrolysis the for pyrolysis vacuum of utilization The [5]. pyrolysis of temperature the of increasing the with increases atmosphere nitrogen the at out that the content of PAHs in fuel oils after pyrolysis which was carried at the temperature of 720°C. Moreover, Cunliffe and Williams found reactions Diels-Alder classical the in pyrolysis of process the during aliphatic from obtained are PAHs health. human for includes: oil polycyclic aromatic hydrocarbons (PAHs), This which are very dangerous [4]. composition chemical different have can oil fuel – product the which in 75–100°C), to amounts difference (this pyrolysis classical the to comparison in temperatures lower at carried out is pyrolysis pyrolysis, vacuum process This this formed. this not during are that gases during dangerous causes temperature, conditions low a milder example of for utilization The [3]. allows to obtain many valuable organic compounds, such as limonene Simultaneously,waste. environment the for dangerous very this of it recycle the for way good very a is it and articles, and patents many in described been has method This tyres. car used of pyrolysis a is Wide applications of limonene in organic synthesis are related to the the to related are synthesis organic in limonene of applications Wide -+-ioee on mil apiain i cseis in cosmetics, in applications mainly found R-(+)-limonene R-(+)-limonene of obtaining industrial the of method Another Fig. 4.Themaindirectionsoflimoneneapplications triel croe crel perillyl carveol, , α-, • 199

science • technique science • technique 200 • p-cymene isachieved–90%Figure5. presence the in radiation of selectivity high the way this microwave In mixture. reaction the on acids Lewis the of action by min 30 to 5 from performed be can p-cymene of synthesis The [10]. limonene of dehydrogenation the by formed is which p-cymene and limonene) of derivatives oxygenated (the 1,2-epoxylimonene and alcohol, development of the breast and colon cancers [16]. Ten[16]. cancers colon and the breast ago, the years of development the hinders it example for cancers, of types certain against activity an shows also R-(+)-limonene heartburn. reliving drugs the in used is it thus acids, stomach the neutralize can also It gallstones. of removal the for treating clinical a in used also is It [15]. for solvent and purificationofthecrudeoilfromsand(bitumen)[14]. outputting of process the improves which compound a as utilization process isusedbytheMilestoneGroup[14]. this – fats other and olives from oils of extraction microwave the in n-hexane of instead applications found (R)-(+)-limonene solvent, a As insects. against crops protect to agriculture in pesticide a as used this family is LimoSol-10 – it is a transparent microemulsion, which is from preparation Another properties. anti- antibacterial used as the solvent, varnish remover and having unique is preparation This LimoSol-90. is R-(+)-limonene of 90% contains removing inks and for adhesives) [13]. and The basic body’s, and well ship known preparation and which concrete cleaning (for the industry of kind many in surfaces dirty clean to cable and flammability, of environmentally friendly aqueous cleaning preparations with a low formation causes It surfactants. with mixed easily be can Limonene [12]. compounds chlorinated for solvent alternative the as industry electronic and automotive aviation, the in process production the in cleaning of surfaces made of different materials. the Moreover,for plants industrial it in used is are R-(+)-limoneneapplied of composition the in containing Today,products compounds. the chlorinated also and derivatives petroleum for solvent alternative the as and agent cleaning the as applications characterized found it thus is fats, to affinity Limonene good a by biodegradable. is it because friendly, to be environmentally are considered its more, properties kg. What’s show that the oral lethal dose of rats R-(+)-limonene on studies toxicological amounts The known. to well also 4400 is toxicology mg/ is It steel corrosionprocessundertheinfluencechlorinatedacids. the for compound fragrance the production of fabrics. This as compound is also used as an inhibitor of utilization the the found has urea textile the industry, In R-(+)-limonene encapsulated in the coating of polyurethane- smoke. cigarette the of smell the it removes ozone, and effectively air with mixture a as refreshers the in used is this When scent. pine a has and active less is isomer S-(-) limonene, in the bergamot and eucalyptus oils. occurs limonene, of isomer second the S-(-)-limonene, [11]. p-cresol beverages and food. In addition, p-cymene is used in the production of perfumery, the in applied cosmetics and were food industry, as and ingredients of fragrances for cosmetics, limonene than valuable more From the medical point of view, R-(+)-limonene is a very good very a is R-(+)-limonene view, of point medical the From Very interesting application of limonene on an industrial scale is its The applications of R-(+)-limonene has been thoroughly studied. All above mentioned oxygenated derivatives of limonene are much Fig. 5.Thesynthesisofp-cymenefromR-(+)-limonene with application ofthemicrowaves However, in comparison to R-(+)- Fig. 7. Biotransformation of with utilization of bacterial H with impregnated the of presence the in and 60°C of temperature a ed t triel frain n aoaiain f h cci ring, cyclic the of which causescymeneformation. aromatization and formation to leads which hydration, as such observed, were reactions side the process this During [19]. obtained was terpinolene and of mixture s ietd o h floig ecin: smrzto, oxidation, isomerization, Figure 6showstheproductsofR-(+)-limonene. reactions: following R-(+)-limonene.The of epoxidation and the aromatization acetoxylation, to directed is food [18].Thesefilmsareusedascontainersforfood. with incontact and biocompatible biodegradable are films received glasses, indicating good permeability and stability to light [18, 19]. The and window for (R)-(+)-limonene coatings as used polyesters be can which 5-hydroxymethylfurfural, active biologically example: for applications, specialist have which polymers, advanced of production and addition epoxidation, hydrogenation. Very valuable is the isomerization, utilization of R-(+)-limonene in the processes: following undergo easy can the It products. valuable many of production the for material raw good a is R-(+)-limonene ring, six-membered the and irritate theskin[17]. the influence of oxygen R-(+)- undergoes oxidation to hydroperoxides, which of disadvantage main limonene are its allergic properties. In addition, R-(+)-limonene under the However, (R)-(+)-limonene. of properties antiasthmatic the identified has Israel from Keinan of team BR388; 6:CYP153A6from Mycobacterium sp. PYEHOLE-1500;8:Ogee from Pseudomonas putida;2:CYP102A7fromBacilluslicheniformis ; 3: monooxygenases anddeoxyhydrogenases: 1:CY P101A1 (P450cam) CYP111A2 fromNovosphingobiumaromaticivorans ; 4:P450cinfrom 2 Bacillus cereus;5:monooxygenase from Bacillusstearothermophilus SO The process of R(+)-limonene isomerization was carried out at out carried was isomerization R(+)-limonene of process The From the point of view of chemical technology a special attention special a technology chemical of view of point Fromthe structure the in bonds double two of presence the to Thanks from Pseudomonas putida;9:CymBfrom Pseudomonas putida; 4 zirconium oxide (ZrO oxide zirconium Fig. 6.TheproductsofR-(+)-limonene isomerization 2 ). As a result of this isomerization the isomerization this of result a As ). nr 4/2016 •tom 70 yrprxd. iue sos h psil ratos ht can that reactions proceed duringtheepoxidationR-(+)-limonene. possible the shows 9 Figure hydroperoxide. cumene and hydroperoxide t-butyl oxygen, molecular peroxide, hydrogen used: were oxidants following the (R)-(+)-limonene of ipxlmnn ad il ws eetd I ws on during found was It detected. was diols and diepoxylimonene carveol, carvone, of: presence the mixtures reactor post-reaction the glass In the in stirrer. magnetic 70°C, and condenser, thermometer reflux a with of fitted temperature the at epoxidation catalysts silicalite (Al titanium hydrotalcites and mesoporous ruthenium complexes, porphyrins, cobalt used: and been have catalysts following the compound this of widely epoxidation the For literature. are the in described heterogeneous, and homogeneous catalysts, of kind of twocarbonatomsinBaeyer-Villiger oxidationreactionisobserved. carbon atoms are linked to the structure, and in the two next stage reagent the loss Grignard a with reaction the In reconstruction skeleton. carbon the the of with and stages two in undergoes process This R-(+)-limonene. from synthesis lavandulol process) many-staged to due (simplified reactions of scheme as the shows 8 microorganisms Figure [20]. roseum such of which presence process, the oxidation in Bayer-Villigerproceeds the the in in utilizations industry founds cosmetics compound This lavandulol. of synthesis alcohol perillyl perillowy, 1,2-epoksylimoneneandcarveol. as: such valuable R-(+)-limonene, obtain of to derivatives R-(+)-limonene allowed oxygenated enzymes of appropriate the ways of utilization shows 7 The enzymes. appropriate the of influence Figure the under transformation bacteria’s. of strains appropriate the by produced enzymes R-(+)-limonene of oxidation the in utilization the be can example An R-(+)-limoneneoxidation. of Fig. 8.ThesynthesisofS-(-)-lavandulolfromR-(+)-limonene withhelp Fig. 9.Reactions proceedduringtheprocessofR-(+)-limonene ain a a. 2] ae tde te rcs o limonene of process the studied have [22] al. at Mariano both of presence the in (R)-(+)-limonene of epoxidations The the is R-(+)-limonene of application interesting very Another It has been shown in the literature many modifications of the process nr 4/2016 •tom 70 2 Mg of Acremoniumroseum 6 (OH) epoxidation 16 CO 3 • 4H • 2 O) [21]. In epoxidation In [21]. O) Acremonium Acremonium cfinl tcnlge o te bann ad tlzto o this of utilization and obtaining the of technologies ecofriendly and efficient modern, the developing is important very that show Summary andconclusions 90–95 mol%,whiletheconversion oflimonenewas20-30mol%. achieved peroxide hydrogen of conversion The used. solvent the on depending changed products of selectivity the and mixtures, reaction post- the of composition the affected considerably time reaction the studies showed that the medium of the reaction, the temperature, The and toluene. i acetonitrile isopropanol, methanol, ethanol, solvents: and its diol in those mixtures. We were used in our studied 5 doff rent 1,2-epoxylimonene alcohol, perillyl carveol, carvone, of presence the The studies on the composition of the post-reaction mixtures showed to 120°C and in the presence of the mesoporous Ti-MCM-41 catalyst. used. The process was carried out at the range of temperatures from 0 as the oxidizing agent 60 wt% water solution of hydrogen peroxide was in environment the natural comparison toorganicsolventssuchastolueneorbenzene. on liquids ionic of influence lower its is limonene of conversion amounted the to 50–90 mol%. The time considerable advantage of this this process after and hour, 1 performed was limonene of epoxidation The oxidant. the as used was peroxide catalyst methylimidazolium tetrafluoroborate [26]. Jacobsen In this the epoxidation hydrogen of presence (immobilized manganese complex), which the was dissolved in 3-buthyl-1- in performed was process way.different the in underwent epoxidation liquid such ionic first The of 1,2-epoxylimoneneamountedto70mol%wasobtained. the solvent was carried out. At the temperature of 60°C the selectivity with theepoxidation hydrogen peroxide as next the oxidizing and agent oxidizer stage and in butane-1-ol first as the in synthesis sieves molecular hydrothermal of the on relied sieves molecular of presence the in limonene of epoxidation The [25]. columns exchange ion and liquids ionic sieves, molecular zincophosphorate and zincochromate amounted to100mol%. limonene was 97 mol%, and the selectivity of the compound compound 100 mol%. In case of t-butyl hydroperoxide conversion of epoxide the of selectivity the and mol%, 40 to amounted limonene ofconversion the as oxidant, the as peroxide hydrogen for obtained were results worse that studies those from results It hours. 24 after made were mixtures reaction post the of analyses quantitative The out in acetonitrile as the solvent and at the temperature of 70 of temperature the at and solvent the as acetonitrile in out specially catalyst prepared [24]. Ti-SBA-15 The studies were carried follows: 68mol%and62mol%. aswere functions these of values acetate ethyl in while mol%, 79 to reached 62 mol% and the selectivity of 1,2-epoxylimonene amounted organic reactant was 30 wt%. In acetonitrile conversion of limonene oxidant/organic of ratio molar reactant amounted to 1:1 and The amount of the catalyst in applied. relation to the was hydroperoxide ethyl and Acetonitrile t-butyl 85°C. agent oxidizing the as and solvents the as of used were acetate temperature the at and glass the reactor in out carried were epoxidations The catalyst. MCM-41 Ti- the on ) (including compounds unsaturated organic the from thestructureofcatalystwasobserved. Ti of leaching no 1 above or 1 was peroxide substrate/hydrogen organic of ratio molar the which at studies the during that shown the Moreover,out. carried was reaction the which at conditions wasit at peroxide hydrogen of decomposition the with connected was It 100%. than lower was compounds organic the to peroxide hydrogen of transformation the of selectivity the that studies the The presented in this article numerous applications of limonene During our research on the process of R-(+)-limonene epoxidation of presence the in epoxidation R-(+)-limonene of process The used: were epoxidation R-(+)-limonene of methods other In hce a a. tde te pxdto o Rlmnn o the on R-limonene of epoxidation the studied al. at Chicker of epoxidation of processes the studied have [23] al. at Berlini • 201 o C. C.

science • technique science • technique 202 • 15. 14. 13. 12. 11. 10. 9. 8. 7. 6. 5. 4. 3. 17. 2. 1. 16. Literature from thefruitjouncesindustry. to recycle the allowsbiomass in the form of orange peels R-(+)-limonenewhich are waste of production The peroxide. hydrogen – titanium mesoporous the agentoxidizing “ecological” the of presence the in catalysts silicate over limonene of epoxidation the can be compound this of utilization the of ways the of One Poland. in produced not is compound this Especially,because compound. terpenes. GreenChemistry2012,14,1447-1454. upon based (NIPU) polyurethanes oligo-and non-isocyanate for monomer Bahr M., Bitto A., Mullhaupt R.: Mullhaupt A., Bitto M., Bahr Chemical Society2004,126,11404–11405. copolymerization of limonene W.:oxide G. and Coates carbon dioxide. B., Journal E. of Lobkovsky American D., S. Allen M., C. Byrne Applied CatalysisAGeneral2010,387,141–146. R.: E. RuizHitzky D., Martin-Luengo M. 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Soxhlet using limonene followed by microwave Clevenger distillation. Journal Microwave-integrated determination: oils’ and fats for solvent green a with Virota M., Tomaoa V., Giniesa C., Visinoni F., Chemata F.: South AfricanJournalofAnimalScience2003,33,89-94. Turkeyperformance. in broiler wild on growing herbs selected from derived Alcicek A., Bozkurt M., Cabuk M.: Technology 1991,25,1646–1649. and Science Environmental oils. pyrolysis vacuum tire used in limonene Pakdel H., Roy Ch., Aubin H., Jean G., Coulombe S.: Coulombe G., Jean H., Aubin Ch., Roy H., Pakdel 57, 91-107. 2001, Pyrolysis Applied and Analytical of Journal tires. used of pyrolysis Pakdel H., Panteaa D. M., Roya C.: Roya M., PakdelPanteaaH.,D. http://www.gea.com/global/en/binaries/CP_ Extraction%20EN_tcm11-23532.PDF informacyjna, broszura Equipment, Mechanical GEA processing. citrus for separator Westfalia dioxide. ChemicalCommunications2009,1312–1330. T.,K.: KohnoSakakura A.: P., Borner S. F., Verevkin Schaffner B., Schaffner S.: Pecoroni Description cardofR-(+)-limonene, Merck,2015. solvents insynthesisandcatalysis.ChemicalReviews 2010,110,4554–4581. . Chemical bioeconomy. the of chemical versatile a Limonene: eaaos dcnes n poes ie fo GEA from lines process and decanters Separators, Sustainable p-cymene and hydrogen from limonene. from hydrogen and p-cymene Sustainable The synthesis of organic carbonates from carbon from carbonates organic of synthesis The The effect of an essential oil combination Cyclic limonene dicarbonate as a new a as dicarbonate limonene Cyclic Production of dl-limonene by vacuum by dl-limonene of Production Use of limonene in countercurrent ytei o pcmn from p-cymene of Synthesis Air oxidation of d–limonene of oxidation Air fetvns o of Effectiveness Organic carbonates as as carbonates Organic Formation of dl- of Formation Green procedure Natural ozone Alternating 25. 24. 23. 18. 22. 21. 20. 19. and oxidation of limonene and compounds aromatic of hydroxylation epoxidation, compounds allylic of processes including catalysts, silicate titanium of applications with cesses pro oxidation interests: Scientific TechnologySzczecin. of in University TechnologyChemical Organic of Institute the Westat the Pomeranianof of University Szczecin Szczecin. Technologyin former – Szczecin in Technology of University PomeranianWest Engineering, Chemical Technologyand of Faculty the (1998). Ph.D. scientific the received nology, of Faculty the from (1994) graduated of Technology).of University Szczecin (former TechnologySzczecin of in University ranian Technology,and Pome - WestEngineering Chemical of Faculty the from national andinternationalconferences. the co-author of 5 patent applications, 1 research paper and 12 posters at processes. oxidation and catalysts silicate titanium liquids, ionic of tific interests: nanotechnology, biochemistry, processes with the utilization Agnieszka Wróblewska, Ph.D., D.Sc., (Eng.), Assoc. Prof. of WPUT. of supervision the Technologyunder of Szczecin, University in meranian Technology,Chemical PoOrganic West of Institute the at programme) ference materials. post-con- and conference in articles full-text 52 as well as conferences, 133 oral presentations and posters presented at national aboutand international applications, patent 26 and patents national 29 articles, technical co-author of 26 chapters in monographs or monographs, 94 scientific and oxidation. and isomerization their and origin natural ofcompounds nanotechnologies, technologies, friendly ecologically lysts, cata- silicate titanium new syntheses oxidants, as hydroperoxide t-butyl Aneza RBESA P.. DS. (n., so. rf has Prof. Assoc. (Eng.), D.Sc., Ph.D., – WRÓBLEWSKA *Agnieszka ais Waylw AK – .c, Eg) hs rdae (2011) graduated has (Eng.), M.Sc., – MALKO Wladyslaw Mariusz e-mail: [email protected] immobilized inionicliquids.CatalysisCommunications2009,135–139. K.: asymmetric epoxidation of F., Bernardo-Gusmao limonene using R. manganese Schiff- Souza complexes De J., Dupont L., Pinto Echavarrıa S., zincochromates. CatalysisToday 2008, 133–135, 80-86. Palacio Amparo Luz J, I.: C. A. G. Vergara A., Santa M. 60, 219–225. N.: Ravasio epoxidation of unsaturated alcohols on Ti-MCM-41. Catalysis R., Today Psaro 2000, G., Moretti M., Guidotti Ch., Berlini Catalysis Today 2008,133-135 , 632-638. rit P M, oe J, enne A, ao E.: Rayon A., Hernandez J., Lopez P. M., Arrieta rprd y otsnhss ehd: ioee pxdto wt H with epoxidation limonene methods: post-synthesis by prepared G.: S. Marchetti R., E. Herrero G., S. Casuscelli V.,M. Cagnoli M., F.,A. J. Alvarez Bengoa G., N. Gallegos D., Marino Biomass intoChemicals.ChemicalReviews 2007,107,2411-2502. VeltyA.: S., Iborra A., Corma 2011, 52,4461–4463. Tetrahedron(S)-lavandulol. and (R)- of synthesis Chemomicrobial Letters K.: Ciolak Cz., Wawrzenczyk J., Kula R., Bonikowski A., Gliszczynska Industrial andEngineeringChemistryResearch 2008,47,4142–4147. F. Barreiro E.: Rodrigues V. G., A., Mata M., I. Martins I., Fernandes N., S. Rodrigues European Polymer Journal2014,50,255–270. applications. packaging food biodegradable for intended blends Limonene zzcn nvriy f ehooy 19) fo wih h also she which from Technology (1994), of University Szczecin ioee pxdto b mlclr ivs icpopae and zincophosphates sieves molecular by epoxidation Limonene He is currently a student of the 3 the of student a currently is He Microencapsulation of limonene for textile application. textile for limonene of Microencapsulation Currently, she works as an Associate Professor Associate an as works she Currently, α - involving hydrogen peroxide and Chemical Routes for the Transformationthe of for Routes Chemical She received her D.Sc. (2009) from (2009) D.Sc. her received She hmcl niern ad Tech and - Engineering Chemical nr 4/2016 •tom 70 rd degree studies (Ph.D.studies degree She is the author or author the is She Ti-MCM-41 catalysts Ti-MCM-41 enr PLA–PHB– Ternary Catalytic Catalytic Scien- He is He 2 O - - 2 .