564-00-1

Basic information

• Product Name: ERYTHRITOL ANHYDRIDE
• Synonyms: (r*,s*)-2,2’-bioxirane;(r*,s*)-diepoxybutane;1,2:3,4-dianhydro-erythrito;1,2:3,4-dianhydroerythritol;2:3,4-diepoxy-meso-butan;meso-1,2;meso-diepoxybutane;ERYTHRITOL ANHYDRIDE
• CAS NO: 564-00-1
• Molecular Formula: C₄H₆O₂
• Molecular Weight: 86.09
• Product Categories: Oxiranes;Simple 3-Membered Ring Compounds
• Mol File: 564-00-1.mol

Chemical Properties

• Melting Point: -19 °C
• Boiling Point: 138 °C
• Flash Point: 45.6°C
• Appearance: /
• Density: 1.11
• Refractive Index: 1.4340 (estimate)
• Merck: 3676
• CAS DataBase Reference: ERYTHRITOL ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ERYTHRITOL ANHYDRIDE(564-00-1)
• EPA Substance Registry System: ERYTHRITOL ANHYDRIDE(564-00-1)

Safety Data

• RTECS: EJ8750000
• Hazardous Substances Data: 564-00-1(Hazardous Substances Data)

Usage

Uses

Used in Polymer Industry:
ERYTHRITOL ANHYDRIDE is used as a curing agent for polymers, enhancing their cross-linking and improving the overall properties of the material. Its ability to form cross-links within the polymer structure contributes to increased strength, durability, and stability of the final product.
Used in Textile Industry:
In the textile industry, ERYTHRITOL ANHYDRIDE is used as a crosslinking agent for textile fibers. This application improves the strength, elasticity, and resistance to abrasion of the fibers, resulting in higher quality and more durable textiles.
The provided materials on ERYTHRITOL ANHYDRIDE highlight its chemical properties and its applications in curing polymers and crosslinking textile fibers. Its versatility as a compound makes it a valuable asset in these industries, where its ability to form cross-links and improve material properties is highly sought after.

Hazard

Quite toxic.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by skin contact. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Upstream product

• 930-22-3 epoxybutene 
• 75-21-8 oxirane 
• 20163-90-0 2,3-dibromo-1,4-dihydroxy-2-butane 
• 106-99-0 buta-1,3-diene 
• 909878-64-4 meso-erythritol 
• 299-74-1 treosulfan 
• 1464-53-5 rac-1,2,3,4-diepoxybutane 
• 139165-54-1 (2S,3S)-1,4-dichlorobutan-2,3-diol 
• 1947-62-2 treosulfan 
• 172821-20-4 (2R,3R)-1,4-diiodobutane-2,3-diol 
• 57495-46-2 (2S,3S)-butane-1,4-diol bis[4-methylbenzenesulfonate] 

Downstream Products

• 2419-73-0 1,4-dichloro-2,3-butanediol 
• 137003-79-3 5-(2-Oxiranyl)-2,2,2-triphenyl-1,2-λ⁵-oxaphospholan 
• 137003-80-6 2,2,2,2',2',2'-Hexaphenyl-5,5'-bi-1,2-λ⁵-oxaphospholan 
• 930-22-3 epoxybutene 
• 643-97-0 erythritol tetranitrate 
• 17177-50-3 (+/-)-(1,2-Dihydroxyethyl)oxirane 
• 6892-68-8 1,4-dithio-erythritol 

Relevant articles and documents

Chiroptical properties of 2,2’-bioxirane

The two enantiomers of 2,2′-bioxirane were synthesized, and their chiroptical properties were thoroughly investigated in various solvents by polarimetry, vibrational circular dichroism (VCD), and Raman optical activity (ROA). Density functional theory (DFT) calculations at the B3LYP/aug-cc-pVTZ level revealed the presence of three conformers (G+, G?, and cis) with Gibbs populations of 51, 44, and 5% for the isolated molecule, respectively. The population ratios of the two main conformers were modified for solvents exhibiting higher dielectric constants (G? form decreases whereas G+ form increases). The behavior of the specific optical rotation values with the different solvents was correctly reproduced by time-dependent DFT calculations using the polarizable continuum model (PCM), except for the benzene for which explicit solvent model should be necessary. Finally, VCD and ROA spectra were perfectly reproduced by the DFT/PCM calculations for the Boltzmann-averaged G+ and G? conformers.

Carbonylation of functionalized diamine diols to cyclic ureas: Application to derivatives of DMP 450

Synthesis of the cyclic urea core structure of the HIV protease inhibitor DMP 450 has been achieved via W(CO)6/I2-catalyzed carbonylation of diamine intermediates. Carbonylations of related functionalized diamines to derivatives of the DMP 450 core structure were also examined. Selected diamine diol substrates could be converted to the cyclic urea core structure by catalytic carbonylation without protection of the diol functionality.

METHOD FOR REPROCESSING MIXTURES CONTAINING BIS-EPOXIDE

The invention relates to a method for reprocessing mixtures containing (a) one or several bis-epoxides of general formula (I), wherein R1 and R2 are identical or different and are selected among hydrogen and C1-C3 alkyl, (b) one or several organic solvents, (c) water, and (d) other optional compounds. The inventive method is characterized in that the mixture is subjected to an at least two-stage distillation process, at least one bis-epoxide (a) being converted into the gas phase in at least one stage.

Interstrand and intrastrand DNA-DNA cross-linking by 1,2,3,4-diepoxybutane: Role of stereochemistry

1,2,3,4-Diepoxybutane (DEB) is a bifunctional electrophile capable of forming DNA-DNA and DNA-protein cross-links. DNA alkylation by DEB produces N7-(2′-hydroxy-3′,4′-epoxybut-1′-yl)-guanine monoadducts, which can then form 1,4-bis-(guan-7-yl)-2,3-butanediol (bis-N7G-BD) lesions. All three optical isomers of DEB are produced metabolically from 1,3-butadiene, but S,S-DEB is the most cytotoxic and genotoxic. In the present work, interstrand and intrastrand DNA-DNA cross-linking by individual DEB stereoisomers was investigated by PAGE, mass spectrometry, and stable isotope labeling. S,S-, R,R-, and meso-diepoxides were synthesized from L-dimethyl-2,3-O-isopropylidene-tartrate, D-dimethyl-2,3-O-isopropylidene- tartrate, and meso-erythritol, respectively. Total numbers of bis-N7G-BD lesions (intrastrand and interstrand) in calf thymus DNA treated separately with S,S-, R,R-, or meso-DEB (0.01-0.5 mM) were similar as determined by capillary HPLC-ESI+-MS/MS of DNA hydrolysates. However, denaturing PAGE has revealed that S,S-DEB produced the highest number of interchain cross-links in 5′-GGC-3′/3′-CCG-5′ sequences. Intrastrand adduct formation by DEB was investigated by a novel methodology based on stable isotope labeling HPLC-ESI+-MS/MS. Meso DEB treatment of DNA duplexes containing 5′-[1,7, NH2-15N3,2- 13C-G]GC-3′/3′-CCG-5′ and 5′-GGC-3′/ 3′-CC[15N3,2-13C-G]-5′ trinucleotides gave rise to comparable numbers of 1,2-intrastrand and 1,3-interstrand bis-N7G-BD cross-links, while S,S DEB produced few intrastrand lesions. R,R-DEB treated DNA contained mostly 1,3-interstrand bis-N7G-BD, along with smaller amounts of 1,2-interstrand and 1,2-intrastrand adducts. The effects of DEB stereochemistry on its ability to form DNA-DNA cross-links may be rationalized by the spatial relationships between the epoxy alcohol side chains in stereoisomeric N7-(2′-hydroxy-3′,4′-epoxybut-1′-yl)- guanine adducts and their DNA environment. Different cross-linking specificities of DEB stereoisomers provide a likely structural basis for their distinct biological activities.

METHOD FOR THE PRODUCTION OF BISEPOXIDES AND DITHIOLS

The invention relates to a method for the production of bisepoxides, characterised in that a conjugated diene of formula (I) is reacted with at least one peroxide with the application of up to 4 equivalents of peroxide per C-C double bond, where R1 is selected from hydrogen and C1-C12 alkyl, unsubstituted or substituted with one or several SH or OH groups, in the presence of a catalyst, obtained by the bringing into contact of at least one manganese compound, selected from A2MnX4, AMnX3, MnY, MnX2 and MnX3 with at least one ligand L, of general formula (II), whereby the variables have the following definitions: X may be the same or different and is selected from monovalent anions, Y is a divalent anion, A is selected from alkali metals and optionally alkylated ammonium, R2 may be different or preferably the same and selected from C1-C20 alkyl and at least one co-ligand, derived from monocarboxylic acids, di- or poly-carboxylic acids or diamines.

Multigram-scale stereoselective synthesis of meso-1,3-butadiene bisepoxide

meso-1,3-Butadiene bisepoxide, a potential building block for natural product synthesis and of interest as a toxic metabolite of butadiene, was synthesized in multi-gram scale in two steps from meso-erythritol in good overall yield.

Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen)CoIII complexes. Practical synthesis of enantioenriched terminal epoxides and 1,2-diols

The hydrolytic kinetic resolution (HKR) of terminal epoxides catalyzed by chiral (salen)CoIII complex 1·OAc affords both recovered unreacted epoxide and 1,2-diol product in highly enantioenriched form. As such, the HKR provides general access to useful, highly enantioenriched chiral building blocks that are otherwise difficult to access, from inexpensive racemic materials. The reaction has several appealing features from a practical standpoint, including the use of H2O as a reactant and low loadings (0.2-2.0 mol %) of a recyclable, commercially available catalyst. In addition, the HKR displays extraordinary scope, as a wide assortment of sterically and electronically varied epoxides can be resolved to ≥ 99% ee. The corresponding 1,2-diols were produced in good-to-high enantiomeric excess using 0.45 equiv of H2O. Useful and general protocols are provided for the isolation of highly enantioenriched epoxides and diols, as well as for catalyst recovery and recycling. Selectivity factors (krel) were determined for the HKR reactions by measuring the product ee at ca. 20% conversion. In nearly all cases, krel values for the HKR exceed 50, and in several cases are well in excess of 200.

Method for production of oxygen-containing organic compound

A novel method for the production of an oxygen-containing organic compound is provided. The production of an oxygen-containing organic compound is attained by oxidizing an olefin, an alcohol, or an aldehyde by catalyzing thereof with a molecular oxygen-containing gas in the presence of a catalyst formed of a polyoxo metalate substituted with a divalent transition metal cation.

Raman, infrared, and microwave spectra and conformational preferences of meso-Bisoxirane

Vibrational infrared and Raman spectra of liquid and solid meso-bisoxirane and infrared spectra of the gaseous phase were recorded. Additionally, microwave rotational spectra from 40 to 18 GHz were recorded. The vibrational spectra demonstrate the presence of two conformations in the fluid phases but only one in the solid state. Infrared and Raman activities and gas-phase band contours indicate that the trans conformer with C(i) molecular symmetry is more stable than the gauche conformer (C1 symmetry). Variable temperature studies of two pairs of Raman lines are consistent with a ΔH value of 0.31 ± 0.10 kcal/mol in the liquid state. Rotational constants (A = 9187.45 ± 0.04, B = 2651.80 ± 0.01, C = 2608.92 ± 0.01 MHz) and the dipole moment (μ(total) = 3.03 D) were determined for the gauche conformer. Model calculations give an acceptable match to the observed rotational constants for an H-C-C'-H' dihedral angle of 60°. The relationship of meso-bisoxirane to other similar three-membered ring compounds is discussed. Published by Elsevier Science B.V.