27987-87-7

Basic information

• Product Name: polydiacetylene
• Synonyms: polydiacetylene;1,3-Butadiyne, homopolymer
• CAS NO: 27987-87-7
• Molecular Formula: C4H2
• Molecular Weight: 50.05868
• Mol File: 27987-87-7.mol
• Article Data: 83

Chemical Properties

• Boiling Point: 10.3°Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 0.806g/cm³
• CAS DataBase Reference: polydiacetylene(CAS DataBase Reference)
• NIST Chemistry Reference: polydiacetylene(27987-87-7)
• EPA Substance Registry System: polydiacetylene(27987-87-7)

Safety Data

• Hazardous Substances Data: 27987-87-7(Hazardous Substances Data)

Upstream product

• 584-12-3 2-bromofuran 
• 5929-72-6 2,7-dimethyl-octa-3,5-diyne-2,7-diol 
• 1529-68-6 1,2,3,4-tetrabromobutane 
• 36678-47-4 1,2-dibromo-buta-1,3-diene 
• 1066-26-8 sodium acetylide 
• 106-97-8 n-butane 
• 689-97-4 3-buten-1-yne 
• 74-85-1 ethene 
• 593-61-3 bromoethyne 
• 2122-48-7 ethynyl 
• 513-37-1 2-methylprop-1-enyl chloride 
• 2810-61-9 but-1-en-3-ynyl 
• 74-86-2 acetylene 
• 6401-87-2 propynyl radical 

Downstream Products

• 4945-70-4 5,5-diphenyl-1,3-pentadiyn-5-ol 
• 103512-95-4 1,1,6,6-tetrakis(p-methoxyphenyl)hexa-2,4-diyne-1,6-diol 
• 101439-73-0 1-(4-nitro-phenyl)-1-phenyl-penta-2,4-diyn-1-ol 
• 103566-02-5 5-ethynyl-3-(3-chloro-phenyl)-isoxazole 
• 107524-50-5 3,3'-bis-(3-chloro-phenyl)-[5,5']biisoxazolyl 
• 62051-68-7 1,6-dimethyl-1,6-diphenylhexa-2,4-diyne-1,6-diol 
• 492998-51-3 hexaiodobutadiene-1,3 
• 103050-85-7 1,6-diphenyl-1,6-di-[2]thienyl-hexa-2,4-diyne-1,6-diol 
• 99172-14-2 but-1-en-3-ynyl-cyclohexyl ether 
• 109255-06-3 but-2-ynal-dicyclohexylacetal 
• 5445-30-7 1-butyl-cyclohexanol 
• 13757-06-7 1-(3-oxo-1-butynyl)cyclohexanol 
• 13757-22-7 1-(5-diethylamino-penta-1,3-diynyl)-cyclohexanol 
• 13757-36-3 2-Methyl-1-(buta-1,3-diinyl)-cyclohexanol 

Relevant articles and documents

Kinetics of the reactions of hydroxyl radicals with diacetylene and vinylacetylene

Highly unsaturated hydrocarbons like diacetylene (C4H2) or vinylacetylene (C4H4) are important intermediates in combustion that can have impact on soot formation. One of their major loss channels is reaction with hydroxyl radicals (OH). We studied the reactions C4H2 + OH → products (1) and C4H4 + OH → products (2) in a quasi-static reactor with helium as bath gas. The hydroxyl radicals were produced by laser flash-photolysis of nitric acid at a wavelength of 248 nm and detected by laser-induced fluorescence with excitation at 282 nm. The rate coefficients were obtained from the intensity-time profiles under pseudo-first order conditions with respect to OH. We found a virtually temperature-independent rate coefficient for reaction (1): k1 = (1.0 ± 0.3) × 10-11 cm3 s-1 (T = 290-670 K, P = 2.7-30.5 bar) and a weakly negative temperature-dependent rate coefficient for reaction (2): k2(T) = (6.4 ± 1.9) × 10-12 exp (486 K/T) cm3 s-1 (T = 295-740 K, P = 1.7-19.2 bar). For neither of the two reactions pressure dependence was observed. From comparisons with analogous reaction systems, we conclude that the dominating reaction pathway is OH addition, where in the case of C4H4 the double bond is preferred over the triple bond.

KINETICS AND MECHANISM OF HYDROCARBON FORMATION IN THE SYSTEM C2H2/O/H AT TEMPERATURES UP TO 1300 K.

The consumption of O atoms and the formation of CO, C//3H//4 (Propyne and propadiene), C//4H//2 (Butadiyne) and other hydrocarbons in the system C//2H//2/O with and without added H atoms has been studied in the temperature range 295-1300 K, p equals 2. 7 mbar. Both the rate of formation and the yield of C//3H//4 in C//2H//2-rich mixtures increases with higher temperature. The rate of C//4H//2 formation increases but the maximum concentration remains constant up to 500 K. The results can be described quantitatively through a slightly modified mechanism of 30 reactions that had been proposed previously for the reaction at room temperature.

Absolute IR Band Intensities of Diacetylene in the 250-4300 cm-1 Region: Implications for Titan's Atmosphere

The infrared spectrum of C4H2, butadyine (also called diacetylene), has been experimentally investigated in the region from 250 to 4300 cm-1 using a Fourier transform spectrometer.A total of 12 bands have been analyzed.For each band, the characteristic wavenumber has been deduced and the values of the absolute band intensities have been systematically determined together with their associated uncertainties.The results provide important data for planetary studies.In particular, a better estimate of the mean statospheric abundance of butadiyne in Titan's atmosphere is obtained: its value is about 50percent higher than previously reported.

Photochemistry of acetylene at 1470 Angstroem

The photolysis of acetylene at 1470 Angstroem has been studied over the pressure region from 13 to 1330 Nm-2 (0.1 to 10 Torr).The quantum yield of diacetylene formation has been measured as a function of C2H2 pressure and the partial pressures of He and H2.The quantum yields of acetylene disappearance and of ethylene and hydrogen formation were also briefly studied.From these results it was concluded that the major primary photochemical process is direct dissociation C2H2 -> C2H + H with a quantum yield of 0.3 and the process of H2 production C2H2 -> C2 + H2 is minor (quantum yield 0.1).The remaining process is the formation of a metastable acetylene which reacts either with ground state acetylene to form C2H radicals or is deactivated by collisions with the walls or inert gases.The C2H radicals react with H2 130 +/- 11 times slower and with CH4 31 +/- 1.7 times slower than with C2H2.Absorption cross sections of diacetylene have been measured in the 1200 and 1800 Angstroem region.The role of acetylene photolysis in the Jovian atmosphere is briefly discussed.

Submerged electric arc between graphite electrodes: A one-pot tool for the synthesis of long-chain polyynes in solution

Polyynes, a class of molecules described by the general formula H-(CC) mH (where m is an integer) can be synthesized using an electric arc between graphite electrodes submerged in an organic solvent such as methanol, n-hexane, n-dodecane, decahydronaphthalene or acetonitrile. When the electric arc is used in acetonitrile at -40°C, polyyne chains of up to 18 carbon atoms (m=9) have been produced together with monocyanopolyyne as by-product. The polyynes can be reduced to ene-ynes by shaking a hexane solution of them with Zn/HCl.

A Flow Tube Study of Ion-Molecule Reactions of Acetylene

The reactivities of C2Hy+, C4Hy+, and C6Hy+ (0 y+ cations into C6- and C8-based cyclic hydrocarbons.Significant differences were noted in reaction rate and product ion distribution between low-pressure and high-pressure techniques of investigating association reactions.Isomeric structures of C4H4+, C6H4+, and C6H5+ are distinguished.

A modified synthesis of tellurophene using NaBH4 to generate sodium telluride

A modified synthesis of tellurophene by reaction of diacetylene with sodium telluride is described. The primary modification involves the convenient in situ generation of sodium telluride by reduction of tellurium metal with NaBH4 in water.

Electronic coupling mediated by furan, thiophene, selenophene and tellurophene in a homologous series of organic mixed valence compounds

Charge delocalization in the mixed-valent monocationic forms of phenothiazine-decorated chalcogenophenes is explored by cyclic voltammetry, optical absorption and EPR spectroscopy. Single units of furan, thiophene, selenophene and tellurophene are found to mediate electronic coupling between the phenothiazines attached to their 2- and 5-positions roughly equally well. Electronic communication seems to occur mostly through the butadiene-like backbone of the chalcogenophenes. the Partner Organisations 2014.

Perthio- and perseleno-1,3-butadienes, -but-1-ene-3-ynes, and -[3]-cumulenes: One-step syntheses from 1,4-dilithio-1,3-butadiyne

(Matrix presented) Treatment of 1,4-dilithio-1,3-butadiyne (1) with dichalcogenides RSSR or RSeSeR affords dithio- and diseleno-1,3-butadiynes (2, 3), perthio- and perseleno-[3]-cumulenes (4, 5), perthio- and perseleno-1,3-butadienes (6, 7), and/or perthio- and perseleno-but-1-ene-3-ynes (8, 9). The products can be controlled by stoichiometry and temperature, by the presence or absence of oxygen, and by choice of the "R" group. By X-ray crystallography, hexa(methylthio)-1,3-butadiene is highly twisted, with a torsion angle [Φ(CCCC)] of 84.7° and an elongated C(2)-C(3) distance of 1.484(3) A.

Formation of fulvene in the reaction of C2H with 1,3-butadiene

Abstract Products formed in the reaction of C2H radicals with 1,3-butadiene at 4 Torr and 298 K are probed using photoionization time-of-flight mass spectrometry. The reaction takes place in a slow-flow reactor, and products are ionized by tunable vacuum-ultraviolet light from the Advanced Light Source. The principal reaction channel involves addition of the radical to one of the unsaturated sites of 1,3-butadiene, followed by H-loss to give isomers of C6H6. The photoionization spectrum of the C6H6 product indicates that fulvene is formed with a branching fraction of (57 ± 30)%. At least one more isomer is formed, which is likely to be one or more of 3,4-dimethylenecyclobut-1-ene, 3-methylene-1-penten-4-yne or 3-methyl-1,2-pentadien-4-yne. An experimental photoionization spectrum of 3,4-dimethylenecyclobut-1-ene and simulated photoionization spectra of 3-methylene-1-penten-4-yne and 3-methyl-1,2-pentadien-4-yne are used to fit the measured data and obtain maximum branching fractions of 74%, 24% and 31%, respectively, for these isomers. An upper limit of 45% is placed on the branching fraction for the sum of benzene and 1,3-hexadien-5-yne. The reactive potential energy surface is also investigated computationally. Minima and first-order saddle-points on several possible reaction pathways to fulvene + H and 3,4-dimethylenecyclobut-1-ene + H products are calculated.

Site-Selective N-Dealkylation of 1,2,3-Triazolium Salts: A Metal-Free Route to 1,5-Substituted 1,2,3-Triazoles and Related Bistriazoles

N3-Alkylation of 1-(pivaloyloxymethyl)-1,2,3-triazoles with alkyl triflates carrying latent "click" functionality, followed by a nucleophile-promoted N1-dealkylation of the resulting strongly electrophilic intermediate triazolium salts, provides an efficient route to 1,5-disubstituted 1,2,3-triazoles. The azide and alkyne groups incorporated by N-alkylation can be submitted to further copper-catalyzed azide-alkyne and Huisgen cycloadditions to provide bis(1,2,3-triazoles) with unprecedented 1,5/1,4 substitution patterns.

METHODS OF PRODUCING DICARBONYL COMPOUNDS

Dicarboxylic acids, such as adipic acid, and diesters, such as adipates, may be produced by hydrogenating alkynes that may be produced from raw materials salvaged from waste stream processes. The carbons of the dicarboxylic acids are provided by alkynes generated from biomass waste and carbon dioxide recovered from waste streams such as exhaust gases.