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Meso 2 3 Butanediol

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Decoding Meso-2,3-Butanediol: A Deep Dive into its Chemistry and Applications



Meso-2,3-butanediol, often abbreviated as meso-2,3-BD, is a fascinating chiral molecule with significant implications across various fields. This article aims to provide a comprehensive understanding of meso-2,3-butanediol, exploring its structure, properties, synthesis, and applications. We will delve into its unique characteristics stemming from its internal symmetry and examine its role in different industries.


Understanding the Structure and Stereochemistry



Meso-2,3-butanediol is a vicinal diol, meaning it possesses two hydroxyl (-OH) groups on adjacent carbon atoms. The crucial aspect of this molecule lies in its stereochemistry. Butanediol itself can exist as four stereoisomers: two enantiomers (R,R and S,S) and two diastereomers, one of which is meso-2,3-butanediol. The meso isomer possesses an internal plane of symmetry, which bisects the molecule, rendering it achiral despite having two chiral centers. This internal symmetry effectively cancels out the optical activity that would otherwise be present in its chiral counterparts. This can be visualized by imagining a plane cutting through the molecule, dividing it into two mirror-image halves.


Physical and Chemical Properties



Meso-2,3-butanediol is a colorless, viscous liquid at room temperature. Its relatively high boiling point (190-192 °C) reflects the presence of strong intermolecular hydrogen bonds between the hydroxyl groups. It exhibits good solubility in water and polar organic solvents, due to its ability to form hydrogen bonds. The chemical reactivity of meso-2,3-butanediol is largely dictated by its hydroxyl groups, which can participate in various reactions like esterification, etherification, and oxidation. For instance, reacting it with acetic acid will produce a diacetate ester.


Synthesis of Meso-2,3-Butanediol



Several methods exist for synthesizing meso-2,3-butanediol. One common route involves the reduction of acetoin (3-hydroxy-2-butanone). This can be achieved using various reducing agents, such as sodium borohydride (NaBH₄) or catalytic hydrogenation. Another approach utilizes the fermentation of sugars by specific microorganisms. Certain bacterial strains can selectively produce meso-2,3-butanediol as a major byproduct during fermentation, making this a potentially sustainable and environmentally friendly synthesis method. This bio-based production is gaining traction due to increasing demands for environmentally friendly chemicals.


Applications in Diverse Industries



The applications of meso-2,3-butanediol span various sectors:

Polymer Chemistry: Meso-2,3-butanediol serves as a valuable monomer or comonomer in the synthesis of polyesters and polyurethanes. Its incorporation improves the flexibility and hydrophilicity of the resulting polymers. For example, it can be used in the production of biodegradable plastics.
Pharmaceutical Industry: It's used as an intermediate in the synthesis of various pharmaceuticals, acting as a building block for more complex molecules with potential medicinal properties.
Cosmetics and Personal Care: Due to its moisturizing properties, it finds application in lotions, creams, and other personal care products. Its humectant properties attract and retain moisture.
Solvent and Reagent: Its ability to dissolve both polar and non-polar compounds makes it a useful solvent in certain chemical reactions. Additionally, it can serve as a reagent in various organic synthesis pathways.
Food Industry (potentially): While not currently a widely used food additive, its potential as a food-grade humectant is being explored. Further research and regulatory approval would be necessary before widespread use.


Conclusion



Meso-2,3-butanediol, with its unique stereochemical properties and versatile reactivity, stands as a crucial chemical compound. Its significance stems from its diverse applications across numerous industries, ranging from polymer science to pharmaceuticals. The growing interest in sustainable and bio-based production methods further underscores its importance in the development of environmentally friendly technologies.


Frequently Asked Questions (FAQs):



1. Is meso-2,3-butanediol toxic? Like many chemicals, meso-2,3-butanediol has a certain level of toxicity. However, its toxicity is relatively low at typical exposure levels. Proper handling and safety measures should always be observed.

2. What is the difference between meso-2,3-butanediol and its chiral isomers? The key difference lies in the stereochemistry. Meso-2,3-butanediol is achiral due to its internal plane of symmetry, while its chiral isomers are optically active. This difference affects their physical properties and reactivity.

3. Can meso-2,3-butanediol be separated from its chiral isomers? Yes, advanced separation techniques like chiral chromatography can be employed to separate meso-2,3-butanediol from its optically active isomers.

4. What are the environmental implications of meso-2,3-butanediol production? Traditional synthetic routes may have some environmental impact. However, bio-based production methods offer a more sustainable alternative, reducing reliance on fossil fuels and minimizing waste.

5. Where can I find meso-2,3-butanediol? Meso-2,3-butanediol can be purchased from various chemical suppliers, both online and offline. The availability may vary depending on the desired purity and quantity.

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meso-2,3-Butanediol - NIST Chemistry WebBook Notes. Go To: Top Data from NIST Standard Reference Database 69: NIST Chemistry WebBook The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment.

meso-2,3-Butanediol - NIST Chemistry WebBook , The Reaction of dl- and meso-2,3-dibromobutane with Silver nitrate in Acetonitrile. Failure of the Nitrate Ester Grouping to Exhibit the Neighboring Group Effect , J. Am. Chem. Soc. , 1957, 79, 2959.

2,3-Butanediol, 98%, mixture of racemic and meso forms, techn., … Shop 2,3-Butanediol, 98%, mixture of racemic and meso forms, techn., Thermo Scientific Chemicals at Fishersci.com

2,3-Butanediol - SpringerLink 29 Sep 2022 · This chemical sequence produces meso-2,3-butanediol from trans-2-butene via trans-2,3-butene oxide, as well as a racemic mixture of R, R- and S,S-2,3-butanediol from cis-2-butene via cis-2,3-butene oxide.

meso-2,3-Butanediol - MilliporeSigma <I>meso</I>-2,3-Butanediol. CH3CH(OH)CH(OH)CH3. CAS 5341-95-7. Molecular Weight 90.12. Browse <I>meso</I>-2,3-Butanediol and related products at Merck.

MESO-2,3-BUTANEDIOL | 5341-95-7 - ChemicalBook 27 Jan 2025 · MESO-2,3-BUTANEDIOL (CAS 5341-95-7) information, including chemical properties, structure, melting point, boiling point, density, formula, molecular weight, uses, prices, suppliers, SDS and more, available at Chemicalbook.

meso-2,3-butanediol | CAS#:5341-95-7 | Chemsrc - 化源网 6 Jan 2024 · Chemsrc provides meso-2,3-butanediol (CAS#:5341-95-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of meso-2,3-butanediol are included as well.

GreenDiol™ (2,3-Butanediol) - Meso - Prospector by UL GreenDiol™ offers diverse effects including superior moisturizing and preservative-boosting effects. It also has excellent dispersing effect for active ingredients such as Vitamin C, as well as high skin penetration which all together make it suitable for cosmetics and personal care products.

meso-2,3-Butanediol 99 5341-95-7 - MilliporeSigma meso-2,3-Butanediol is a diol. 2,3-Butanediol (2,3-DB) exists in three stereoisomeric forms: dextro, levo and meso. 2,3-DB is a crucial chemical feedstock and has wide applications in industry. Production of meso -2,3-butanediol under low oxygen condition by metabolically engineered Escherichia coli is reported.

meso-butane-2,3-diol | C4H10O2 - ChemSpider ChemSpider record containing structure, synonyms, properties, vendors and database links for meso-butane-2,3-diol, 5341-95-7, OWBTYPJTUOEWEK-ZXZARUISSA-N Accessed: Simple

meso-2,3-Butanediol | C4H10O2 | CID 220010 - PubChem meso-2,3-Butanediol | C4H10O2 | CID 220010 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more.

2,3-Butanediol (mixture of meso- D- and L-form) for synthesis 513 … 2,3-Butanediol (mixture of meso- D- and L-form) for synthesis; CAS Number: 513-85-9; Synonyms: 2,3-Butanediol,2,3-Butylene glycol; Linear Formula: CH3CH(OH)CH(OH)CH3 at Sigma-Aldrich

meso -2,3-Butanediol - MilliporeSigma <I>meso</I>-2,3-Butanediol. CH3CH(OH)CH(OH)CH3. CAS 5341-95-7. Molecular Weight 90.12. Browse <I>meso</I>-2,3-Butanediol and related products at MilliporeSigma.

2,3-Butanediol analytical standard, mixture of racemic and meso … 2,3-Butanediol analytical standard, mixture of racemic and meso forms; CAS Number: 513-85-9; EC Number: 208-173-6; Synonyms: 2,3-Butylene glycol; Linear Formula: CH3CH(OH)CH(OH)CH3 at Sigma-Aldrich

Acid And Base Catalyzed Reaction Mechanisms in Bio Butadiene … 10 Feb 2025 · 2,3-butanediol (2,3‑BDO) dehydration to 1,3‑butadiene (BD) is assessed over a Sc2O3 catalyst calcined at 800°C (Sc2O3_800) and compared with performance of an in‑house prepared ZrO2 (ZrO2_HT_800) catalyst via active sites, activity, product distribution and apparent activation energies to elucidate the reaction mechanism.

2,3-Butanediol | 513-85-9 - ChemicalBook 27 Jan 2025 · 2,3-Butanediol(23BD) is the organic compound with the formula (CH3CHOH). It is classified as a vic-diol (glycol). It exists as three stereoisomers, a chiral pair and the meso isomer.

meso-2,3-Butanediol - NIST Chemistry WebBook Van Den Dool and Kratz RI, non-polar column, temperature ramp. View large format table.

2,3-Butanediol - Wikipedia 2,3-Butanediol is the organic compound with the formula (CH 3 CHOH) 2. It is classified as a vic -diol (glycol). It exists as three stereoisomers, a chiral pair and the meso isomer. All are colorless liquids. Applications include precursors to various plastics and pesticides.

2,3-Butanediol 98 513-85-9 - MilliporeSigma CRISPR/Cas9 in Pichia pastoris: 2,3-Butanediol (BDO) is used in the construction of P. pastoris cell factories as a representative example to demonstrate the procedures for integrating multiple heterologous genes using the CRISPR-based multiplex genome integration toolkit (Gao et al., 2024). Antifungal activity in sorghum: 2,3-butanediol, a metabolite of A. oryzae YRA3, can …

meso-2,3-Butanediol, 99% | 361461-10G | SIGMA-ALDRICH | SLS meso-2,3-Butanediol is a diol. 2,3-Butanediol (2,3-DB) exists in three stereoisomeric forms: dextro, levo and meso. 2,3-DB is a crucial chemical feedstock and has wide applications in industry.

meso-2,3-Butanediol - NIST Chemistry WebBook , The Reaction of dl- and meso-2,3-dibromobutane with Silver nitrate in Acetonitrile. Failure of the Nitrate Ester Grouping to Exhibit the Neighboring Group Effect , J. Am. Chem. Soc. , 1957, 79, 2959.

2,3-Butanediol | C4H10O2 | CID 262 - PubChem 2,3-Butanediol (at least 80% meso isomer, the rest racemic mixture) is used as a crosslinking agent for naphthalene-1,5-diisocyanate in the production of specific hard-rubber products (Vulkollan).