Extraction of β-carotene from orange peel and carrot waste for cotton dyeing Susan Hecker - PDF

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Thesis for the Degree of Master in Science with a major in Textile Engineering The Swedish School of Textiles Report no Extraction of β-carotene from orange peel and carrot waste

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Thesis for the Degree of Master in Science with a major in Textile Engineering The Swedish School of Textiles Report no Extraction of β-carotene from orange peel and carrot waste for cotton dyeing Susan Hecker Visiting adress: Skaraborgsvägen 3 Postal adress: Borås Website: II Master thesis by Susan Hecker Description: Thesis submitted for the degree of Master in Science in Textile Engineering Title: Extraction of β-carotene from orange peel and carrot waste for cotton dyeing Author: Susan Hecker Supervisor: Mats Johansson, Vincent Nierstrasz Cooperation partners: University Borås, Almedahls Brämhults Juice AB, School of Engineering at the Examiner: Anders Persson The Swedish School of Textiles Report no Master thesis by Susan Hecker III Acknowledgement At the School of Textiles in Borås I would like to thank Maria Björklund and Catrin Tammjärv who helped me and had always an open ear for all my questions and thoughts. For the good feedbacks and discussions I want to thank my supervisors Vincent Nierstrasz and Mats Johansson. Special thanks for the help with the HPLC analysis to Jorge Ferreira at the Engineer school at the University of Borås. Thanks to Stina Haglund at Brämhults Juice AB for the allocation of the orange peel and carrot residue. Anna Frisk and Karin Eklund at Almedahls made it possible that I could make the Xenon test there. And of course I would like to thank my family and friends who supported me during my whole studies and especially during my master thesis work. Borås, June 2014 Susan Hecker IV Master thesis by Susan Hecker Abstract The further usage of vegetable and plant waste from juice pressing industry as textile dyes is presented in this thesis. The thesis is focused on β-carotene (C 40 H 56 ) dyestuff extracted from orange peel and carrot residue. The three organic solvents; ethyl acetate, petroleum ether and hexane/acetone (1:1 v/v) were used for the extraction. The analysis of the extract was done by RP-HPLC with a C18 column. The yield and the purity of the extracted β-carotene were determined. The highest yield was achieved with petroleum ether whereas the other two solvents were nearly as good. The highest and purest amount on β-carotene was found in the extracts of carrots. The dyeing process was continued with β-carotene dyestuff of orange peel and carrot residue extracted from 27 g of residue on 0,8 g cotton in the dyeing ratio 1:50. Unmordant and post mordanted bleached and mercerized cotton fabric was dyed. 10% alum of the weight fraction of cotton was used as mordant. Colour measurements (K/S, C*, L*, a*, b*, h and ΔE) and fastness properties as light- (ISO-Norm B02) and wash fastness (ISO 105 C) were tested. Fair light fastness grades were achieved by β-carotene dyestuff of orange peel residue dyed on cotton fabric. Poorer were the grades for β-carotene dyestuff of carrot residue for both unmordanted and mordanted samples. The wash fastness couldn t achieve reasonable results neither for β-carotene dyestuff from carrots nor orange peel residue, dyed on cotton fabric. Keywords: β-carotene, carrot and orange peel residue, organic solvent extraction, cotton dyeing Master thesis by Susan Hecker V Popular abstract Brämhults Juice AB a juice pressing company in Borås, Sweden has every year 8100 tons of orange peel waste and 570 tons of carrots waste from juice pressing that still contains a lot of natural resources, such pigments and colorants. Using these pigments and colorants further would increase its efficiency. A market for the further usage would be the food or textile dyeing industry. The main colorant in carrots and orange peel residues is β-carotene (C 40 H 56 ). β-carotene is a water insoluble yellow-orange pigment. Nowadays it is used in the food industry as food colorant and pro vitamin A precursor. In this paper the further usage of dying cotton fabric is investigated. Due to solvent extraction β-carotene can be obtained in a quite pure form from carrots residue and in less pure form from orange peel residue. The dyed cotton fabric is red-orange for carrot extract. The orange peel extract contains besides β-carotene also other carotenes; flavonoids, phenolic acids, pectin and waxes. The dyed cotton is light yellow-orange. The fastness properties to stand washing and light exposure were tested. The light fastness properties got fair results for β-carotene dyestuff of orange peel residue dyed on cotton fabric and less fair results for the carrot extract. The wash fastness properties couldn t achieve reasonable results. VI Master thesis by Susan Hecker Content List ACKNOWLEDGEMENT ABSTRACT POPULAR ABSTRACT TABLE LIST FIGURE LIST LIST OF ABBREVIATIONS IV V VI IX X XI 1. INTRODUCTION 2 2. LITERATURE REVIEW Β-CAROTENE CARROTS AND ORANGE PEEL EXTRACTION METHODS AND SOLVENT PROPERTIES DYEING WITH NATURAL SOURCES MORDANTS DYE AND DYEING METHOD PROBLEM DESCRIPTION AIM RESEARCH QUESTION MATERIALS AND METHODS MATERIALS DRYING OF THE CARROT AND ORANGE PEEL RESIDUE EXTRACTION METHOD ANALYSIS OF THE DYESTUFF, PURITY AND YIELD COTTON DYEING SPECTROPHOTOMETRIC MEASUREMENTS FASTNESS PROPERTIES TESTS XENON TEST (ISO-NORM B02) WASH FASTNESS TEST (ISO 105 C) RESULTS AND DISCUSSION DETERMINATION OF Β-CAROTENE SPECTRUM RESULTS OF THE RP-HPLC ANALYSIS MORDANTING AND DYEING SPECTROPHOTOMETRIC COLOUR MEASUREMENTS RESULTS OF THE WASH FASTNESS TEST (ISO 105 C) RESULTS OF THE XENON TEST (ISO-NORM B02) 31 Master thesis by Susan Hecker VII 6. CONCLUSIONS FUTURE RESEARCH 34 REFERENCES 35 APPENDIX APPENDIX I AQUEOUS EXTRACTION ORGANIC SOLVENTS EXTRACTION WITH ETHANOL RESULTS OF THE HPLC ANALYSIS APPENDIX II CHEMICAL STRUCTURES OF THE SOLVENTS USED APPENDIX III VAT DYE APPENDIX IV HPLC RESULTS APPENDIX V SPECTROPHOTOMETRIC AND FASTNESS PROPERTY RESULTS I II II III IV VI VI VII VII VIII VIII XII XII VIII Master thesis by Susan Hecker Table List TABLE 1: TOTAL CAROTENOIDS AND THE CONTENT OF DIFFERENT CAROTENE AND XANTHOPHYLLS IN CARROTS AND ORANGE PEEL IN MG/G CARROTS/ORANGE PEEL... 7 TABLE 2: SOLVENT PROPERTIES OF THE USED SOLVENTS... 9 TABLE 3: AMOUNTS OF THE DRIED RESIDUES (G) AND SOLVENTS (ML) THAT WERE USED FOR THE HPLC SAMPLES AND THE DYESTUFF EXTRACTION FOR THE COTTON DYEING TABLE 4: COMPOSITION OF THE USED Β-CAROTENE DYESTUFF OF CARROT AND ORANGE PEEL RESIDUE THAT WAS USED FOR THE DYEING OF 0,8 G COTTON FABRIC TABLE 5: FINAL DYE RECEIPT. AMOUNT PER LITRE WATER AND THE CALCULATED AMOUNT THAT WAS USED FOR THE DYEING OF 0,8 G COTTON FABRIC IS LISTED TABLE 6: THREE DIFFERENT CONCENTRATIONS USED FOR THE HPLC-STANDARD CURVE TABLE 7: Β-CAROTENE CONTENT IN CARROTS AND ORANGE PEEL (MG/G OF CARROTS OR ORANGE PEEL) TABLE 8: COLOUR COORDINATION OF THE DYED COTTON FABRICS WITH CARROT EXTRACT TABLE 9: COLOUR COORDINATION OF THE DYED COTTON FABRICS WITH ORANGE PEEL EXTRACT TABLE 10: RESULTS OF THE WASH FASTNESS TEST OF UNMORDANTED AND POST MORDANTED (ALUM) DYED COTTON FABRICS OF ORANGE PEEL AND CARROT EXTRACT TABLE 11: RESULTS OF THE XENON LIGHT FASTNESS TEST OF UNMORDANTED AND POST MORDANTED (ALUM) DYED COTTON FABRICS OF ORANGE PEEL AND CARROT EXTRACT TABLE 12: Β-CAROTENE CONTENT IN CARROTS AND ORANGE PEEL (ΜG/G)... IV TABLE 13: DIFFERENT PARAMETERS FOR VAT DYEING ON COTTON FABRIC... VII TABLE 14: RESULTS OF THE DETERMINATION OF Β-CAROTENE BY HPLC... VIII TABLE 15: COLOUR COORDINATION OF THE ALL DYED COTTON FABRICS WITH CARROT EXTRACT... XII TABLE 16: COLOUR COORDINATION OF THE ALL DYED COTTON FABRICS WITH ORANGE PEEL EXTRACT... XII TABLE 17: RESULTS OF THE WASH FASTNESS TEST OF ALL UNMORDANTED AND POST MORDANTED (ALUM) DYED COTTON FABRICS OF ORANGE PEEL AND CARROT EXTRACT.... XIII TABLE 18: RESULTS OF THE LIGHT FASTNESS TEST OF ALL UNMORDANTED AND POST MORDANTED (ALUM) DYED COTTON FABRICS OF ORANGE PEEL AND CARROT EXTRACT.... XIII Master thesis by Susan Hecker IX Figure List FIGURE 1: FRUITS AND VEGETABLE WASTE FROM JUICE PRESSING OF BRÄMHULTS JUICE AB IN TONS PER YEAR FIGURE 2: WASTE HANDLING OF BRÄMHULTS JUICE AB. WASTE IN TONS PER YEAR FIGURE 3: ALL-TRANS Β-CAROTENE... 4 FIGURE 4: CAROTENOIDS CLASSIFICATIONS... 5 FIGURE 5: Β-CAROTENE SYNTHESIS BY WITTIG REACTION... 6 FIGURE 6: 9-CIS-Β-CAROTENE... 6 FIGURE 7: DESICCATOR SILICA UNDER VACUUM CONTAINING ORANGE PEEL AND CARROT PIECES FIGURE 8: GRINDING DRIED ORANGE PEEL AND CARROTS IN A MORTAR FIGURE 9: EXTRACTION FROM CARROTS IN PETROLEUM ETHER FIGURE 10: GRAPH OF THE DETERMINED WAVELENGTH OF Β-CAROTENE AT 450 NM FIGURE 11: HPLC-STANDARD CURVE OF Β-CAROTENE FIGURE 12: HPLC GRAPH AT 450 NM SHOWING Β-CAROTENE, Α-CAROTENE AND ZEAXANTHIN EXTRACTED FROM CARROT RESIDUE FIGURE 13: HPLC GRAPH AT 450 NM SHOWING Β-CAROTENE, Α-CAROTENE AND ZEAXANTHIN EXTRACTED FROM ORANGE PEEL RESIDUE FIGURE 14: Β-CAROTENE DYESTUFF OF CARROT RESIDUE, DYED ON COTTON, MORDANTED AND UNMORDANTED FIGURE 15: Β-CAROTENE DYESTUFF OF ORANGE PEEL RESIDUE, DYED ON COTTON, MORDANTED AND UNMORDANTED FIGURE 16: HPLC FROM CARROT EXTRACT IN AQUEOUS SOLUTION AT 450 NM... IV FIGURE 17: HPLC FROM ORANGE PEEL EXTRACT IN AQUEOUS SOLUTION AT 450 NM... IV FIGURE 18: HPLC FROM CARROT EXTRACT IN 80 % AQUEOUS ETHANOL SOLUTION AT 450 NM... IV FIGURE 19: HPLC FROM ORANGE PEEL IN 80 % AQUEOUS ETHANOL SOLUTION AT 450 NM... V FIGURE 20: HPLC GRAPH OF SAMPLE 1 Β-CAROTENE FROM ORANGE PEEL, EXTRACTED IN ETHYL ACETATE VIII FIGURE 21: HPLC GRAPH OF SAMPLE 7 Β-CAROTENE FROM ORANGE PEEL, EXTRACTED IN ETHYL ACETATE.. IX FIGURE 22: HPLC GRAPH OF SAMPLE 3 Β-CAROTENE FROM ORANGE PEEL, EXTRACTED IN HEXANE/ACETONE... IX FIGURE 23: HPLC GRAPH OF SAMPLE 9 Β-CAROTENE FROM ORANGE PEEL, EXTRACTED IN HEXANE/ACETONE... IX FIGURE 24: HPLC GRAPH OF SAMPLE 2 Β-CAROTENE FROM ORANGE PEEL, EXTRACTED IN PETROLEUM ETHER... IX FIGURE 25: HPLC GRAPH OF SAMPLE 8 Β-CAROTENE FROM ORANGE PEEL, EXTRACTED IN PETROLEUM ETHER... X FIGURE 26: HPLC GRAPH OF SAMPLE 4 Β-CAROTENE FROM CARROT, EXTRACTED IN ETHYL ACETATE... X FIGURE 27: HPLC GRAPH OF SAMPLE 10 Β-CAROTENE FROM CARROT, EXTRACTED IN HEXANE/ACETONE... X FIGURE 28: HPLC GRAPH OF SAMPLE 6 Β-CAROTENE FROM CARROT, EXTRACTED IN HEXANE/ACETONE... X FIGURE 29: HPLC GRAPH OF SAMPLE 12 Β-CAROTENE FROM CARROT, EXTRACTED IN HEXANE/ACETONE... XI FIGURE 30: HPLC GRAPH OF SAMPLE 5 Β-CAROTENE FROM CARROT, EXTRACTED IN PETROLEUM ETHER... XI FIGURE 31: HPLC GRAPH OF SAMPLE 11 Β-CAROTENE FROM CARROT, EXTRACTED IN PETROLEUM ETHER... XI X Master thesis by Susan Hecker List of Abbreviations Abbreviation Unit Definition Å Ångström a* Red-green b* Blue-yellow C* Chroma FTIR Fourier transform infrared spectroscopy h Hue HPLC High Performance Liquid Chromatography K/S Kubelka Munk, colour strength or colour uptake L* Lightness NaOH Sodium hydroxide Owf Of the weight fraction RP-HPLC Reverse-Phase High Performance Liquid Chromatography TLC Thin Layer Chromatography UV Ultra violet v Volume V Volt ΔE Colour difference between uncoloured and coloured fabric μg Microgram λ max Maximal absorption Master thesis by Susan Hecker XI 1. Introduction Plant material like fruits, berries, roots, barks, vegetables, leaves etc. have been used for textile dyeing over hundreds of years (Cardon, 2007). With the industrialisation and the invention of synthetic dyes, natural dyes disappeared almost entirely in the textile industry (Cardon, 2007, Hardman and Pinhey, 2009). With their well-known structures synthetic dyes became easier in handling, higher in process safety and better in reproducibility compared to natural dyes and so a success for dye houses. Nevertheless different researchers investigated in the recent years again in new methods on dyeing with natural material and their extracts. The used extraction methods are mostly organic-solvent extraction (Saleh et al., 2013, Yi and Yoo, 2010). The article by Saleh et al. (2013) shows great potential of dyeing cotton fabric with β-carotene containing dyestuff extracts, extracted from banana leaves by organic solvent extraction. The results evidenced high tensile strength, high colour strength, and high fastness properties for the dyed cotton fabrics. Brämhults Juice AB, Borås has 8100 tons of orange peel waste and 570 tons of carrots waste from juice pressing each year (Figure 1). In this state after the juice pressing the vegetable and fruit residues still contain a lot of natural resources such as colorants and pigments (Brämhults Juice AB, 2014). A further use of the waste could be the textile dyeing industry (Guinot et al., 2007, Saleh et al., 2013). With extraction and purification of the pigments, dyes comparable to synthetically textile dyes can be achieved Orange peel Carrots Others Figure 1: Fruits and vegetable waste from juice pressing of Brämhults Juice AB in tons per year. 2 Master thesis by Susan Hecker β-carotene is a natural yellow-red pigment. Its chemical formula is C 40 H 56. Its sources are mainly plants, vegetables and fruits with a yellow-red colour as carrots and oranges. It is an important precursor for vitamin A since it cannot be synthesised in the human body. The intake has to be over the diet (Schlieper, 2005). As colorant it is used in the food industry under the numbers E160 a-f (Domke et al., 2004). The total amount of residue of the juice pressing of all vegetables and fruits from Brämhults Juice is 9300 tons per year Biogas production and fodder Fodder 8300 Waste disposal Figure 2: Waste handling of Brämhults Juice AB. Waste in tons per year. This is composed of 8300 tons that is used for the biogas production and fodder, 500 tons for fodder and 500 tons for waste disposal (Figure 2) (Brämhults Juice AB, 2014). A suitable extraction method of β-carotene from orange peel and carrot residue would gain an additional value to their waste. The further use of the residues can be economically beneficial for both the juice pressing and the textile dyeing industry. Synthetically produced β-carotene and the extracted β-carotene from natural sources have the same chemical structure and are therefore comparative with each other. Master thesis by Susan Hecker 3 2. Literature review The following literature review gives a look into the physical and chemical properties of β- carotene, its synthesis and uses today. It gives an overview on the existing research in the field of extraction of β-carotene and other natural pigments and their appliance in different dyeing methods. It is shown how much β-carotene other researchers could extract from orange peel and carrots. An investigation on different solvents and their suitability for β- carotene extraction was done. Different dyeing methods used for water insoluble dyes and on cotton and the usage of mordants is described as well β-carotene β-carotene is a natural yellow-red coloured pigment with the chemical structure C 40 H 56, (Figure 3). It occurs mainly in plants, fruit and vegetables. It belongs to the group of carotenes that together with xanthophyll belongs to the upper-level grouping of carotenoids (Bergmann, 2004). Chemically β-carotene is classified as tetraterpene (Koskinen, 2012). Carotenoids are divided in oxygen containing molecules (xantophylls) and non-oxygen containing molecules (carotene) (Domke et al., 2004), Figure 4. The lack of hydroxyl groups makes β-carotene hydrophobic. Due to its two cyclic rings at each end of the molecule chain, β-carotene is a dicyclic compound, composed of 8 isoprene-units (C 5 H 8 ). The high amount of conjugated double bonds is called chromophor and is responsible for the colour impression (Bergmann, 2004). β-carotene absorbs light of the wavelength 450 nm of the visible part of the spectrum (Bauernfeind, 1981). Figure 3: All-trans β-carotene In the nature carotenoids have an indispensable protective role for chlorophyll and the human eyes by absorbing and dissipating excessive light energy that would damage them 4 Master thesis by Susan Hecker (Campbell, 2003). β-carotene is the most common carotene (Schlieper, 2005). β-carotene is very sensitive to light, heat and oxygen. It can change its chemical structure due to oxidation, degradation or isomerization. The latter doesn t have any effect on the colour impression of β-carotene because the double bonds do not break (Liaaen-Jensen, 1989). The handling of carrots and orange peel residue for the β-carotene pigment extraction and the later dyeing process therefore has to be handled with care. Too high exposures to light, heat and oxygen have to be avoided. The storing is recommended under frozen conditions. According to Qian et al. (2012) the β-carotene stability against degradation is higher at a ph between 4-8. Natural β-carotene occurs in trans- and cis-isomers whereas synthetically produced β- carotene is mostly all-trans-form, due to its higher absorbance for the human body (Bundesinstitut für Risikobewertung, 2013). Carotenoids Carotene (hydrophobic) Xantophylls (hydrophillic) β-carotene α-carotene Lutein Zeaxanthin Lycopene etc. etc. Figure 4: Carotenoids classifications The β-carotene synthesis is either produced by employing a Wittig reaction or a Grignard reaction (Koskinen, 2012). The following reaction (Figure 5) is by Wittig. It shows a transselective Wittig olefination of aldehydes II synthesis of β-carotene from a dialdehyde. Master thesis by Susan Hecker 5 Figure 5: β-carotene synthesis by Wittig reaction As vitamin A precursor, synthetically produced β-carotene is especially important for the use in the food industry as completion to the natural, in the food existing β-carotene. As food additive with the purpose of a food colorant it is known under the numbers E160 a-f. (Domke et al., 2004) Figure 6: 9-cis-β-carotene 6 Master thesis by Susan Hecker 2.2. Carrots and Orange peel Carrots and orange peels are a rich source for carotenoids. Carotenoids, especially β- carotene is present in both of them and is responsible for their yellow-orange colour. Main compounds in carrots and orange peel are β-carotene, α-carotene, lutein and zeaxanthin (Table 1), (Heinonen, 1990, Wang et al., 2008, Curl and Bailey, 1956). Additionally orange peel contains flavonoids, phenolic acids, pectin and waxes (Wang et al., 2008). The compounds in orange peels extracts are by some researches tested on their UV-protective properties and antimicrobial activity (Hou et al., 2013, Yi and Yoo, 2010). The total carotenoids content and the amount of some xantophylls and carotenes of carrots and orange peel are listed below. Table 1: Total carotenoids and the content of different carotene and xanthophylls in carrots and orange peel in mg/g carrots/orange peel Carrots Article Orange peel Article Total carotenoids 0,16 0,38 Mustafa et al. (2012) 0,45 Wang et al. (2008) Carotenes (hydrophobic carotenoids) β-carotene 0,046 0,10 Heinonen (1990) 0,05 0,056 Dumbravă et al. (2010), Wang et al. (2008) α -carotene 0,022 0,049 Heinonen (1990) 0,017 0,019 Curl and Bailey (1956) Xanthophylls (hydrophilic carotenoids) Lutein 0,0011 0,0056 Zeaxanthin 0,0574 Heinonen (1990) Curl and Bailey (1956) 0,029 Wang et al. (2008) 0,027 Wang et al. (2008) Master thesis by Susan Hecker 7 2.3. Extraction methods and solvent properties In literature different extraction methods for β-carotene (carotenes) from orange peel, carrots and other fruits, vegetables and plants are described. The most common method is the organic solvent extraction. It was described by several different researches for the extraction of β-carotene from orange peel (Ghazi, 1999), (Dumbravă et al., 2010) and carrots (Biswas et al., 2011), (Fikselova et al., 2008), (Livny et al., 2003), (Marx et al., 2000), but also from other vegetables and plants as tomato, paprika (Levy et al., 1995) and from the algae Dunaliella salina (Marchal et al., 2013), (Mojaat et al., 2008). Several other extraction methods for β-carotene were researched. So were investigations on supercritical fluid extraction of β-carotene done by Kaur et al. (2012), Chandra and Nair (1997) and Benelli et al. (2010) for car
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