Abstract
Lactic acid (LA) is a nifty molecule with an eclectic range of applications in innumerable industries and is produced through biological and chemical processes. Factually, LA is converted into lactide (LAC), which is the precursor for polylactic acid (PLA). PLA is considered one of the first-rate replacements for petroleum-based products and is believed to be environmentally sustainable. Nevertheless, it has always been challenging due to increased PLA productivity costs. Reduction in the LA and LAC production price directly echoes the production price of PLA. Therefore, low-cost LA and LAC production methods have to be found to produce PLA effectively. Hence, this study uses cheap agricultural sources derived microbial LA to make LAC through dimerization. Produced LAC was analyzed through FT-IR, NMR, TGA and XRD. FT-IR results revealed that the successful dimerization of LA to LAC, NMR analysis revealed that the aligning of methine and methyl groups in produced LAC, TGA analysis exposed that the microbial LAC has more thermal stability than the commercial LAC, XRD results showed that the produced LACs are crystalline with 32% and 42% crystallinity. To the best of our acquaintance, this manuscript is pioneering one to describe LA production through microbial fermentation and uses this monomer to produce LAC through dimerization.
Data availability
Not applicable.
Abbreviations
- LA:
-
Lactic acid
- LAC:
-
Lactide
- LAB:
-
Lactic acid bacteria
- MLA:
-
Microbial lactic acid
- CLA:
-
Commercial lactic acid
- CLAC:
-
Lactide from commercial source
- MLAC:
-
Lactide from microbial fermentation
- PLA:
-
Polylactic acid
- DP:
-
Direct polycondensation
- ROP:
-
Ring-opening polymerisation
- NMR:
-
Nuclear magnetic resonance
- XRD:
-
X-ray diffraction
- FT-IR:
-
Fourier transform infra-red spectroscopy
- TGA:
-
Therma-gravimetric analysis
References
Abdel-Rahman MA, Tashiro Y, Sonomoto K (2013) Recent advances in lactic acid production by microbial fermentation processes. Biotechnol Adv 31:877–902. https://doi.org/10.1016/j.biotechadv.2013.04.002
Achmad F, Yamane K, Quan S, Kokugan T (2009) Synthesis of polylactic acid by direct polycondensation under vacuum without catalysts, solvents and initiators. Chem Eng J 151:342–350. https://doi.org/10.1016/j.cej.2009.04.014
Ahmad A, Othman I, Rambabu K et al (2021) Polymerization of lactic acid produced from food waste by metal oxide-assisted dark fermentation. Environ Technol Innov. https://doi.org/10.1016/j.eti.2021.101862
Alexandri M, Blanco-Catalá J, Schneider R et al (2020) High l(+)-lactic acid productivity in continuous fermentations using bakery waste and lucerne green juice as renewable substrates. Bioresour Technol 316:123949. https://doi.org/10.1016/j.biortech.2020.123949
Bernardo MP, Coelho LF, Sass DC, Contiero J (2016) l-(+)-lactic acid production by Lactobacillus rhamnosus B103 from dairy industry waste. Braz J Microbiol 47:640–646. https://doi.org/10.1016/j.bjm.2015.12.001
Botvin V, Karaseva S, Khasanov V (2020) Depolymerization of lactic acid oligomers into lactide: epimerization, stereocomplex formation, and nature of interactions of oligomers. Polym Degrad Stab. https://doi.org/10.1016/j.polymdegradstab.2020.109382
Casalini T, Rossi F, Castrovinci A, Perale G (2019) A perspective on polylactic acid-based polymers use for nanoparticles synthesis and applications. Front Bioeng Biotechnol 7:1–16. https://doi.org/10.3389/fbioe.2019.00259
Chuensangjun C, Kanomata K, Kitaoka T et al (2019) Surface-modified cellulose nanofibers-graft-poly(lactic acid)s made by ring-opening polymerization of l-lactide. J Polym Environ 27:847–861. https://doi.org/10.1007/s10924-019-01398-y
Cunha BLC, Bahú JO, Xavier LF et al (2022) Lactide: production routes, properties, and applications. Bioengineering 9:1
David H, Patrick G, Jim L, Jed R (2005) Polylactic acid technology. Nat Fibers Biopolym Biocompos. https://doi.org/10.1201/9780203508206.ch16
Ding WD, Pervaiz M, Sain M (2018) Cellulose-enabled polylactic acid (PLA) nanocomposites: recent developments and emerging trends. Funct Biopolym 2018:183–216
Fitzpatrick JJ, O’Keeffe U (2001) Influence of whey protein hydrolysate addition to whey permeate batch fermentations for producing lactic acid. Process Biochem 37:183–186. https://doi.org/10.1016/S0032-9592(01)00203-5
Garlotta D (2001) A literature review of poly(lactic acid). J Polym Environ 9:63–84
Ghaffar T, Irshad M, Anwar Z et al (2014) Recent trends in lactic acid biotechnology: a brief review on production to purification. J Radiat Res Appl Sci 7:222–229. https://doi.org/10.1016/j.jrras.2014.03.002
Glotova VN, Zamanova MK, Yarkova AV et al (2014) Influence of storage conditions on the stability of lactide. Procedia Chem 10:252–257. https://doi.org/10.1016/j.proche.2014.10.042
Henton DE, Gruber P, Lunt J, Randall J (2005) Natural fibers, biopolymers, and biocomposites. 16. Polylactic acid technology. Nat Fibers Biopolym Biocompos 2005:527–578
Horváth T, Marossy K, Szabó TJ (2022) Ring-opening polymerization and plasticization of poly(l-lactic)acid by adding of glycerol-dioleate. J Therm Anal Calorim 147:2221–2227
Hu Y, Daoud WA, Cheuk KKL, Lin CSK (2016) Newly developed techniques on polycondensation, ring-opening polymerization and polymer modification: focus on poly(lactic acid). Materials. https://doi.org/10.3390/ma9030133
Hua J, Lv Q, Wang Z et al (2018) Ring-opening polymerization of l-lactide catalyzed by a novel molybdenum-based catalytic system. Iran Polym J (engl Ed) 27:319–327. https://doi.org/10.1007/s13726-018-0612-y
Inkinen S, Hakkarainen M, Albertsson AC, Södergård A (2011) From lactic acid to poly(lactic acid) (PLA): characterization and analysis of PLA and its precursors. Biomacromol 12:523–532. https://doi.org/10.1021/bm101302t
Jamshidian M, Tehrany EA, Imran M et al (2010) Poly-lactic acid: production, applications, nanocomposites, and release studies. Compr Rev Food Sci Food Saf 9:552–571. https://doi.org/10.1111/j.1541-4337.2010.00126.x
John RP, Anisha GS, Nampoothiri KM, Pandey A (2009) Direct lactic acid fermentation: focus on simultaneous saccharification and lactic acid production. Biotechnol Adv 27:145–152. https://doi.org/10.1016/j.biotechadv.2008.10.004
Kaihara S, Matsumura S, Mikos AG, Fisher JP (2007) Synthesis of poly(l-lactide) and polyglycolide by ring-opening polymerization. Nat Protoc 2:2667–2671. https://doi.org/10.1038/nprot.2007.391
Korhonen H, Helminen A, Seppa Èla JV (2005) Synthesis of polylactides in the presence of co-initiators with different numbers of hydroxyl groups. Polymer 42:7541–7549
Kumar S, Yadav N, Nain L, Khare SK (2020) A simple downstream processing protocol for the recovery of lactic acid from the fermentation broth. Bioresour Technol 318:124260. https://doi.org/10.1016/j.biortech.2020.124260
Li Z, Ding S, Li Z, Tan T (2006) L-lactic acid production by Lactobacillus casei fermentation with corn steep liquor-supplemented acid-hydrolysate of soybean meal. Biotechnol J 1:1453–1458. https://doi.org/10.1002/biot.200600099
Lin HTV, Huang MY, Kao TY et al (2020) Production of lactic acid from seaweed hydrolysates via lactic acid bacteria fermentation. Fermentation 6:12–14. https://doi.org/10.3390/FERMENTATION6010037
López-Gómez JP, Alexandri M, Schneider R, Venus J (2019) A review on the current developments in continuous lactic acid fermentations and case studies utilising inexpensive raw materials. Process Biochem 79:1–10. https://doi.org/10.1016/j.procbio.2018.12.012
López-Gómez JP, Alexandri M, Schneider R et al (2020a) Organic fraction of municipal solid waste for the production of l-lactic acid with high optical purity. J Clean Prod. https://doi.org/10.1016/j.jclepro.2019.119165
López-Gómez JP, Unger P, Schneider R, Venus J (2020b) From upstream to purification: production of lactic acid from the organic fraction of municipal solid waste. Waste Biomass Valorization 11:5247–5254. https://doi.org/10.1007/s12649-020-00992-9
Lunelli BH, Andrade RR, Atala DIP et al (2010) Production of lactic acid from sucrose: Strain selection, fermentation, and kinetic modeling. Appl Biochem Biotechnol 161:227–237. https://doi.org/10.1007/s12010-009-8828-0
Masutani K, Kimura Y (2014) Chapter 1. PLA synthesis. In: From the monomer to the polymer, pp 1–36
Mendiburu-Valor E, Larraza I, Echeverria-Altuna O et al (2023) Thermoset polyurethanes from biobased and recycled components. J Polym Environ. https://doi.org/10.1007/s10924-023-02891-1
Mohite KK, Garnaik B (2020) Kinetic and biocompatibility investigation on the catalytic ring opening polymerization of l-lactide in bulk using cyclic Bu2Sn initiators derived from ethylene glycol, pentaerythritol and cloisite 30B. Polyhedron. https://doi.org/10.1016/j.poly.2019.114202
Nanaki S, Barmpalexis P, Iatrou A et al (2018) Risperidone controlled release microspheres based on poly(lactic acid)–poly(propylene adipate) novel polymer blends appropriate for long acting injectable formulations. Pharmaceutics. https://doi.org/10.3390/pharmaceutics10030130
Oonkhanond B, Jonglertjunya W, Srimarut N et al (2017) Lactic acid production from sugarcane bagasse by an integrated system of lignocellulose fractionation, saccharification, fermentation, and ex-situ nanofiltration. J Environ Chem Eng 5:2533–2541. https://doi.org/10.1016/j.jece.2017.05.004
Park J, Cho H, Hwang D et al (2018) Design of a novel process for continuous lactide synthesis from lactic acid. Ind Eng Chem Res 57:11955–11962. https://doi.org/10.1021/acs.iecr.8b02419
Probst M, Fritschi A, Wagner A, Insam H (2013) Biowaste: a lactobacillus habitat and lactic acid fermentation substrate. Bioresour Technol 143:647–652. https://doi.org/10.1016/j.biortech.2013.06.022
Rahmayetty, Whulanza Y, Sukirno EA et al (2018) Use of Candida rugosa lipase as a biocatalyst for l-lactide ring-opening polymerization and polylactic acid production. Biocatal Agric Biotechnol 16:683–691. https://doi.org/10.1016/j.bcab.2018.09.015
Rawoof SAA, Kumar PS, Vo DVN et al (2021) Production of optically pure lactic acid by microbial fermentation: a review. Environ Chem Lett 19:539–556. https://doi.org/10.1007/s10311-020-01083-w
Richter K, Träger A (1994) (l+)-Lactic acid from sweet sorghum by submerged and solid-state fermentations. Acta Biotechnol 14:367–378. https://doi.org/10.1002/abio.370140409
Romero-Garcia S, Hernández-Bustos C, Merino E et al (2009) Homolactic fermentation from glucose and cellobiose using Bacillus subtilis. Microb Cell Fact 8:1–8. https://doi.org/10.1186/1475-2859-8-23
Shuklov IA, Jiao H, Schulze J et al (2011) Studies on the epimerization of diastereomeric lactides. Tetrahedron Lett 52:1027–1030. https://doi.org/10.1016/j.tetlet.2010.12.094
Sin LT, Tueen BS (2019) Synthesis and production of poly(lactic acid). In: Polylactic acid. Elsevier, London, pp 53–95
Spaggiari M, Ricci A, Calani L et al (2020) Solid state lactic acid fermentation: a strategy to improve wheat bran functionality. Lwt 118:108668. https://doi.org/10.1016/j.lwt.2019.108668
Sreenath HK, Moldes AB, Koegel RG, Straub RJ (2001) Lactic acid production by simultaneous saccharification and fermentation of alfalfa fiber. J Biosci Bioeng 92:518–523. https://doi.org/10.1016/S1389-1723(01)80309-1
Su L, Zou J, Dong S et al (2017) Influence of different β-nucleation agents on poly(l-lactic acid): structure, morphology, and dynamic mechanical behavior. RSC Adv 7:55364–55370. https://doi.org/10.1039/c7ra10550a
Teng L, Xu X, Nie W et al (2015) Synthesis and degradability of a star-shaped polylactide based on l-lactide and xylitol. J Polym Res. https://doi.org/10.1007/s10965-015-0719-1
Vignesh Kumar B, Muthumari B, Kavitha M et al (2022) Studies on optimization of sustainable lactic acid production by Bacillus amyloliquefaciens from sugarcane molasses through microbial fermentation. Sustainability (switzerland) 14:7400. https://doi.org/10.3390/SU14127400
Vignesh Kumar B, Muthumari B, Kavitha M et al (2023) Unraveling the role of intra-cellular metabolites in the lactic acid production by novel Bacillus amyloliquefaciens using sugarcane molasses as substratum. RSC Mol Omics. https://doi.org/10.1039/D3MO00141E
Wang Y, Zhang LF, Wang P, Shen LJ (2010) Ring-opening polymerization of l-lactide with rare earth aryloxides substituted by various alkyl groups. Chin J Polym Sci (engl Ed) 28:509–515. https://doi.org/10.1007/s10118-010-9065-2
Wang G, Tang S, Cao F et al (2018) Preparation of high purity lactide using a high-boiling-point alcohol immobilization method. Ind Eng Chem Res 57:7711–7716. https://doi.org/10.1021/acs.iecr.8b01088
Wang J, Huang J, Laffend H et al (2020) Optimization of immobilized Lactobacillus pentosus cell fermentation for lactic acid production. Bioresour Bioprocess. https://doi.org/10.1186/s40643-020-00305-x
Wang G, Hao X, Dong Y, Zhang L (2023) Bio-based poly(butylene succinate-co-dodecylene succinate) derived from 1,12-dodecanediol: synthesis and characterization. J Polym Environ. https://doi.org/10.1007/s10924-023-02916-9
Zaini NAM, Chatzifragkou A, Tverezovskiy V, Charalampopoulos D (2019) Purification and polymerisation of microbial d-lactic acid from DDGS hydrolysates fermentation. Biochem Eng J. https://doi.org/10.1016/j.bej.2019.107265
Zhan S, Wan Z, Zhao Y et al (2020) Ring-opening dispersion polymerization of l-lactide initiated by l-arginine in supercritical carbon dioxide. Polym Degrad Stab. https://doi.org/10.1016/j.polymdegradstab.2019.109049
Zhang W, Li X, Zhang T et al (2017a) High-rate lactic acid production from food waste and waste activated sludge via interactive control of pH adjustment and fermentation temperature. Chem Eng J 328:197–206. https://doi.org/10.1016/j.cej.2017.06.174
Zhang X, Wang H, Liu C et al (2017b) Synthesis of thermoplastic xylan-lactide copolymer with amidine-mediated organocatalyst in ionic liquid. Sci Rep 7:1–10. https://doi.org/10.1038/s41598-017-00464-6
Acknowledgements
All the author’s thanks to DST-PURSE, Department of Botany (Phase II—3rd Instalment), and RUSA 2.0, Alagappa University for the financial support of this research work, and also Research Instrumentation facilities of the Department of Botany, Energy Science, Animal Health and Management, Bioinformatics, Microbiology, Biotechnology, Inorganic Chemistry, Physics, Alagappa University, NMR facility, The Gandhigram Rural Institute—Deemed to be University. XRD Facility, Department of Physics, TGA and NMR Facility, Department of Chemistry, National Changhua University of Education, Taiwan. The first author thanks to Taiwan Education Exchange Programme (TEEP) Internship for partially supporting this work. This work was also supported by grants from the Ministry of Science and Technology, Taiwan (MOST 111-2621-B-018-001 to Jui-Yu Chou). The first author thanks Dr. Immauel Paulraj, Dr. Pravinraj Selvaraj, Mr. Palepu Teja Ravindar, Ms. Catherine, and Ms. Agalya for their support and help.
Funding
This research received no external funding.
Author information
Authors and Affiliations
Contributions
BVK: conceptualization; data curation; formal analysis; methodology; writing—original draft; writing—review and editing BM: formal analysis; methodology; MK: formal analysis; methodology; JKJPK: formal analysis; methodology; MJB and JYC: conceptualization; data curation; formal analysis; funding acquisition; investigation; methodology; project administration; resources; supervision; validation; visualization; writing—review and editing. All authors have read and agreed to the published version of the manuscript.
Corresponding author
Ethics declarations
Conflict of interest
The authors declare no conflict of interest.
Rights and permissions
About this article
Cite this article
Balasubramanian, V.K., Balakrishnan, M., Murugan, K. et al. Synthesis and characterization of lactide from Bacillus amyloliquefaciens brewed lactic acid utilizing cheap agricultural sources. 3 Biotech 14, 13 (2024). https://doi.org/10.1007/s13205-023-03855-x
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s13205-023-03855-x