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Cas Database

75-44-5

75-44-5

Identification

  • Product Name:Carbonic dichloride

  • CAS Number: 75-44-5

  • EINECS:200-870-3

  • Molecular Weight:98.9164

  • Molecular Formula: CCl2 O

  • HS Code:2812103000

  • Mol File:75-44-5.mol

Synonyms:Phosgene(8CI); CG; Carbon dichloride oxide; Carbon oxychloride; Carbonyl chloride;Carbonyl dichloride; Chloroformyl chloride; Dichloroformaldehyde; Phosgen

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Safety information and MSDS view more

  • Pictogram(s):Very toxic via inhalation, strong irritant to eyes. TLV: 0.1 ppm.

  • Hazard Codes:T+,F

  • Signal Word:Danger

  • Hazard Statement:H314 Causes severe skin burns and eye damageH330 Fatal if inhaled

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Half-upright position. Administration of oxygen may be needed. Refer immediately for medical attention. In case of skin contact ON FROSTBITE: rinse with plenty of water, do NOT remove clothes. Rinse skin with plenty of water or shower. Refer immediately for medical attention. In case of eye contact Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. Phosgene is a lung toxicant that causes damage to the capillaries, bronchioles and alveoli of the lungs, by decomposition to hydrochloric acid. There is little immediate irritant effect upon the respiratory tract, and the warning properties of the gas are therefore very slight. Pulmonary edema, bronchopneumonia and occasionally lung abscesses develop. Degenerative changes in the nerves have been reported as later developments. A concentration of 25 ppm is dangerous for exposures lasting 30-60 minutes and 50 ppm is rapidly fatal after even short exposure. (EPA, 1998) /PREHOSPITAL/ Quickly access for a patent airway, ensure adequate respiration and pulse. If trauma is suspected, maintain cervical immobilization manually and apply a cervical collar and a backboard when feasible. ... If victims can walk, lead them out of the Hot Zone to the Decontamination Zone. Victims who are unable to walk may be removed on backboards or gurneys; if these are not available, carefully carry or drag victims to safety. Victims should be kept warm and quiet; any activity subsequent to exposure may increase the likelihood of death.

  • Fire-fighting measures: Suitable extinguishing media Use remote equipment wherever possible. Use water spray to keep fire-exposed containers cool. Extinguish fire using agent suitable for surrounding fire. When heated to decomposition or on contact with water or steam, it will react to produce toxic and corrosive fumes. Reacts violently with aluminum; tert-butyl azido formate; 2,4-hexadiyn-1,6-diol; isopropyl alcohol; potassium; sodium; hexafluoro isopropylidene; amino lithium; lithium. Stable in steel containers if dry. Avoid moisture. (EPA, 1998) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Evacuate danger area! Consult an expert! Personal protection: chemical protection suit including self-contained breathing apparatus. Ventilation. Shut off cylinder if possible. Remove gas with fine water spray. Isolate the area until the gas has dispersed. For liquid spills, cover with sodium bicarbonate or an equal mixture of soda ash and slaked lime. After mixing, spray water from an atomizer with great precaution. Transfer slowly into a large container of water. ... For gas spills, allow gas to flow into a mixed solution of caustic soda and slaked lime. If possible, keep in a hood until cylinder is emptied.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Fireproof if in building. Isolated from work area. Separated from incompatible materials. See Chemical Dangers. Cool. Dry. Ventilation along the floor.Phosgene must be stored to avoid contact with water, moisture, or steam since violent reactions occur. Store in tightly closed, steel containers in an isolated area away from the work area and separated form all other materials, as well as sunlight. Although phosgene in anhydrous equipment is not corrosive to ordinary metals, in presence of moisture, use monel, tantalum, or glass-lined storage containers. Phosgene should be stored away from heating and cooling ducts. Containers should be frequently inspected for leaks.

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 10 Hr Time-Weighted Avg: 0.1 ppm (0.4 mg/cu m).Recommended Exposure Limit: 15 Min Ceiling Value: 0.2 ppm (0.8 mg/cu m).Biological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 134 Articles be found

Hill, D. G.

, p. 32 - 40 (1932)

Transition-metal-catalyzed oxidation of carbon monoxide by dichlorine to produce phosgene

Calderazzo, Fausto,Belli Dell'Amico, Daniela

, p. 3639 - 3642 (1982)

Halometal carbonyls of gold, palladium, and platinum catalyze the formation of COCl2 from carbon monoxide and dichlorine at atmospheric pressure and room temperature under exclusion of light. Semiquantitative data show that the catalytic efficiency in this homogeneous process is Au > Pd > Pt. Attack at the carbonyl carbon of soluble halo-carbonyl complexes by coordinated chloride or by dichlorine to give unstable M-C(O)-Cl groupings is believed to be operative in these processes.

Crummett,Stenger

, p. 434,1083 (1956)

Armstrong

, p. 245 (1870)

Rollefson

, (1933)

-

Ramsperger, H. C.,Waddington, G.

, p. 214 - 220 (1933)

-

ULTRAVIOLET PHOTOOXIDATION FOR THE DESTRUCTION OF VOCS IN AIR

Bhowmick, Madhumita,Semmens, Michael

, p. 2407 - 2416 (1994)

Air stripping is an effective and economical process for removing volatile organic chemicals (VOCs) from contaminated water sources. However the air stripping process simply transfers the contaminants from the water to the air phase where they may continue to pose an environmental problem. In this study, the use of ultraviolet light (u.v.) photooxidation for treating the off gas from air stripping is examined. Subsequent papers will address linking u.v. photooxidation with air stripping in a closed loop stripping process. Fundamental studies are conducted to characterize the kinetics of the gas phase photooxidation of five volatile chlorinated alkanes and alkenes under different operating conditions. - Keywords: u.v.; volatile organic compounds; photooxidation; kinetics; gas phase; water treatment

In situ solid-state NMR studies of trichloroethylene photocatalysis: Formation and characterization of surface-bound intermediates

Hwang, Son-Jong,Petucci, Chris,Raftery, Daniel

, p. 4388 - 4397 (1998)

In situ solid-state NMR methodologies have been employed to investigate the photocatalytic oxidation of trichloroethylene (TCE) over two TiO2-based catalysts, Degussa P-25 powder and a monolayer TiO2 catalyst dispersed on porous Vycor glass. 13C magic angle spinning (MAS) experiments reveal that similar reaction intermediates form on the surfaces of both catalysts. Long- lived intermediates, including dichloroacetyl chloride (Cl2HCCOC1, DCAC), carbon monoxide, and pentachloroethane and final products CO2, phosgene (Cl2CO), and HCl were observed under dry conditions. The presence of molecular oxygen was found to be essential for TCE photooxidation to proceed. Adsorbed water was found to greatly reduce the formation of phosgene. The formation of surface-bound dichloroacetate and trichloroacetate species was observed and identified via 13C cross polarization MAS experiments. Dichloroacetate, which forms from mobile DCAC, appears to be bound to the nonirradiated surfaces of the powdered TiO2 catalysts and further degradation was not possible. Formation of di- and trichloroacetate also takes place on the TiO2/PVG catalyst in the absence of light; however, their concentrations are low. Degradation studies of these surface-bound species indicate that the photooxidation of dichloroacetate, is slow and results in the formation of phosgene and CO2, while trichloroacetate remains resistive to degradation on the TiO2/PVG catalyst. Our results also indicate that the formation of DCAC and phosgene seems to be a general result of TCE degradation which is not limited to TiO2 photocatalysis but instead may be more characteristic of the types of initiating species which are formed by UV irradiation. However, the TiO2 surface is the most effective in terms of the observed initial rates of degradation.

Chatterji,Dhar

, p. 155 (1930)

Reaction of carbon tetrachloride with hydrogen peroxide

Tatarova,Trofimova,Gorban',Khaliullin

, p. 1403 - 1406 (2004)

Reaction of carbon tetrachloride with aqueous hydrogen peroxide in the presence of anhydrous iron(III) chloride was studied. Optimal conditions for the preparation of phosgene were found on the basis of analysis of the kinetic data and mechanism of the process. The reaction rate and yield (the latter reaching 95% in the stationary mode) are determined mainly by the amount of the heterogeneous catalyst. According to the experimental data, the reaction follows a radical mechanism.

A simplified [11C]phosgene synthesis

Bramoullé, Yann,Roeda, Dirk,Dollé, Frédéric

, p. 313 - 316 (2010)

A new flow-through system for the production of [11C]phosgene, a versatile labelling agent in radiochemistry for PET, is described. Cyclotron-produced [11C]CH4 is mixed with Cl2 and converted into [11C]CCl4 by passing the mixture through an empty quartz tube at 510 °C. The outflow is directed through a Sb-filled guard that takes out Cl2 and then, without intentional O2 addition, through a second empty quartz tube at 750 °C, giving rise to [11C]phosgene in 30-35% radiochemical yield.

Bent Carbon Surface Moieties as Active Sites on Carbon Catalysts for Phosgene Synthesis

Gupta, Navneet K.,Pashigreva, Anastasia,Pidko, Evgeny A.,Hensen, Emiel J. M.,Mleczko, Leslaw,Roggan, Stefan,Ember, Erika E.,Lercher, Johannes A.

, p. 1728 - 1732 (2016)

Active sites in carbon-catalyzed phosgene synthesis from gaseous CO and Cl2 have been identified using C60 fullerene as a model catalyst. The carbon atoms distorted from sp2 coordination in non-planar carbon units are concluded to generate active Cl2. Experiments and density functional theory calculations indicate the formation of a surface-bound [C60?Cl2] chlorine species with radical character as key intermediate during phosgene formation. It reacts rapidly with physisorbed CO in a two-step Eley-Rideal-type mechanism.

CCl4 chemistry on the reduced selvedge of a α-Fe 2O3(0 0 0 1) surface: A scanning tunneling microscopy study

Rim, Kwang Taeg,Fitts, Jeffrey P.,Müller, Thomas,Adib, Kaveh,Camillone III, Nicholas,Osgood, Richard M.,Joyce,Flynn, George W.

, p. 59 - 75 (2003)

Scanning tunneling microscopy (STM) and low energy electron diffraction (LEED) were used to study the degradation of CCl4 on the reduced selvedge of a natural single crystal α-Fe2O3(0001) surface in ultrahigh vacuum. Before exposure to CCl4, STM images indicate that approximately 85% of the reduced surface exhibits a Fe 3O4(111) 2×2 termination, while the remaining 15% is terminated by 1×1 and superstructure phases. Images obtained after room temperature dosing with CCl4 and subsequent flashing to 600 K reveal that chlorine atoms are adsorbed only on surface regions with the Fe 3O4(111) 2×2 termination, not on 1×1 and superstructure regions. Chlorine atoms from dissociative adsorption of CCl 4 are observed to occupy two distinct positions located atop lattice protrusions and in threefold oxygen vacancy sites. However, in companion chemical labeling experiments, chlorine atoms provided by room temperature, dissociative Cl2 adsorption on this surface are found to occupy sites atop lattice protrusions exclusively. The clear dissimilarity in STM feature shape and brightness at the two distinct chlorine adsorption sites arising from CCl4 dissociation as well as the results of the Cl 2 chemical labeling experiments are best explained via reactions on a Fe3O4(111) 2×2 selvedge terminated by a 1/4 monolayer of tetrahedrally coordinated iron atoms. On this surface, adsorption atop an iron atom occurs for both the CCl4 and Cl2 dissociative reactions. A second adsorption site, assigned as binding to second layer iron atoms left exposed following surface oxygen atom abstraction resulting in the formation of phosgene (COCl2), only appears in the case of reaction with CCl4. The reaction mechanism and active site requirements for CCl4 degradation on iron oxide surfaces are discussed in light of this evidence and in the context of our previously reported results from Auger electron spectroscopy (AES), LEED, temperature-programmed desorption (TPD), and X-ray photoelectron spectroscopy studies.

Photodecomposition of chloroform catalyzed by unmodified MCM-41 mesoporous silica

Pena, Laura A.,Chan, Alissa M.,Cohen, Larissa R.,Hou, Karen,Harvey, Brent M.,Hoggard, Patrick E.

, p. 760 - 766 (2014)

Unactivated MCM-41 mesoporous silica catalyzes the photodecomposition of chloroform to phosgene and hydrogen chloride under near-UV (λ > 360 nm) irradiation. The rate of photodecomposition increases toward an asymptotic limit as the O2 partial pressure is increased. Deuterochloroform does not decompose under the same experimental conditions. Low concentrations of both cyclohexane and ethanol quench the photodecomposition, whereas water, up to its solubility limit, does not. Dissolved tetraalkylammonium salts suppress photodecomposition. The data are consistent with a mechanism in which light absorption by an SiO2 defect yields an electron-deficient oxygen atom, which then abstracts hydrogen from chloroform. The resulting CCl 3 radicals react with oxygen to form a peroxy radical that decomposes, eventually yielding phosgene and hydrogen chloride. Unmodified MCM-41 silica catalyzes the photodecomposition of chloroform under near-UV irradiation. It is proposed that decomposition is initiated through hydrogen abstraction from chloroform at a photoactive SiO2 defect site.

-

Fowler,Beaver

, p. 4186 (1953)

-

Lyons,Dikinson

, p. 443 (1935)

Spurny, Z.

, p. 337 - 340 (1963)

Chapman, A. T.

, p. 419 - 422 (1935)

Schulte, J. W.,Suttle, J. F.,Wilhelm, R.

, p. 2222 - 2227 (1953)

New members of an old family: Isolation of IC(O)CI and IC(O)Br and evidence for the formation of weakly bound Br...CO

Romano, Rosana M.,Della Vedova, Carlos O.,Downs, Anthony J.,Tobon, Yeny A.,Willner, Helge

, p. 3241 - 3248 (2005)

The photochemically induced reactions of a dihalogen, XY, with CO isolated together in an Ar matrix at about 15 K lead to the formation of carbonyl dihalide molecules XC(O)Y, where X and Y may be the same or different halogen atoms, Cl, Br, or I. In addition to the known compounds OCCI2, OCBr2, and BrC(O)Cl, the carbonyl iodide chloride, IC(0)Cl, and carbonyl iodide bromide, IC(O)C, compounds have thus been identified for the first time as products of the reactions involving ICl and IBr, respectively. The first product to be formed in reactions with Cl2, BrCl, or ICI is the CICO radical, which reacts subsequently with a second halogen atom to give the corresponding carbonyl dihalide [OCCI2, BrC(O)Cl, or IC(O)Cl]. The analogous reaction with Br2 affords, in low yield, the unusually weakly bound BrCO radical, better described as a van der Waals complex, Br...CO. The changes have been followed and the products characterized experimentally by their infrared spectra, and the spectra have been analyzed in light of the results afforded by ab initio (Hartree-Fock and Moeller-Plesset second-order) and density functional theory calculations.

Silverman,Olofson

, p. 1313 (1968)

Stock et al.

, p. 140 - 146 (1931)

Chapman, A. T.

, p. 416 - 419 (1935)

Carbonyl dihalides: Synthesis and spectroscopic characterization

Parkington, Michael J.,Ryan, T. Anthony,Seddon, Kenneth R.

, p. 251 - 256 (1997)

New, or improved, syntheses of phosgene, carbonyl bromide chloride and carbonyl bromide fluoride have been elaborated. The NMR (13C, 19F and 17O) and electron impact mass spectra were recorded for COX2 (X = F, C

-

Chapman,Gee

, p. 1726 (1911)

-

Oxychlorination of CO to phosgene in a three-step reaction cycle and corresponding catalytic mechanism

Zhang, Tianzhu,Troll, Carsten,Rieger, Bernhard,Kintrup, Juergen,Schlueter, Oliver F.-K.,Weber, Rainer

, p. 76 - 85 (2010)

An improved procedure, three-step reaction cycle procedure, for the continuous preparation of phosgene from CO, air and HCl catalyzed by CuCl2 was reported for the first time. The corresponding catalytic mechanism of each step was preliminarily disclosed with the powder X-ray diffraction (XRD) analysis: the first step is the oxychlorination of CO to phosgene and simultaneous reduction of CuCl2 to CuCl; the second step is the oxidation of CuCl with air to Cu2OCl2, and the third step is the neutralization of Cu2OCl2 with HCl to CuCl2. The regeneration of catalyst consists of steps 2 and 3, which is called the two-step regeneration of catalyst. The no-simultaneous existence of Cu (I) chloride and water in this three-step reaction procedure prevented effectively copper (I) chloride from the disproportionation. The influence of regeneration conditions, including reaction time, pressure of air or HCl on morphologies and recovery degree of catalyst were investigated and discussed. The degree of recovery for the single-run yield and cumulative yield of phosgene from the two-step regenerated oxychlorination agent can reach, respectively, 87.0% and 97.0% whereas the single-run yield and cumulative yield of phosgene with the one-step regenerated catalyst only can be recovered to 58.8% and 80.5%, respectively. The two-step regeneration method also can result in a higher dispersion of CuCl2/KCl on silica gel than that of the one-step regeneration. These results not only can offer a quite promising potential for the industrial use, but also can promote our deeply understanding of this important industrial reaction.

Chapman, A. T.

, p. 818 - 823 (1934)

Discussion on decomposition of chloroform

Kawai

, p. 1125 - 1132 (1966)

-

Jacox,Milligan

, p. 866 (1965)

Photochemistry of chloropicrin in cryogenic matrices

Wade, Elisabeth A.,Reak, Kristina E.,Parsons, Bradley F.,Clemes, Thomas P.,Singmaster, Karen A.

, p. 473 - 479 (2002)

The photolysis of chloropicrin (CCl3NO2) was investigated in Ar and N2 cryogenic matrices. The extent of reaction was monitored using FT-IR spectroscopy. Phosgene and nitrosyl chloride were the observed photoproducts at all wavelengths investigated (220, 251, 313, 365, and 405 nm). When the photolysis was performed with 220, 251, or 313 nm light, two additional bands were also observed. These bands have been assigned to CCl3ONO. Chloropicrin was also photolyzed in the presence of O2 and 18O2. 18O-labeled photoproducts were not detected in cryogenic matrices.

Kinetics of the Oxidation of Trichloroethylene in Air via Heterogeneous Photocatalysis

Jacoby, William A.,Blake, Daniel M.,Noble, Richard D.,Koval, Carl A.

, p. 87 - 96 (1995)

Trichloroethylene in solution with air is oxidized rapidly in the presence of irradiated titanium dioxide.Dichloroacetyl chloride (DCAC), which is formed as an intermediate during the trichloroethylene reaction, also undergoes photocatalytic oxidation.This paper describes the kinetics of these reactions and how operating conditions influence the observed reaction rates.Annular photocatalytic reactors with thin films of titanium dioxide catalyst were used to make kinetic measurements.Observations of the reaction rate of trichloroethylene were made while varying parameters such as catalyst loading, feed flow rate, feed composition, and ultraviolet light energy.The observed reaction rates are higher by several orders of magnitude than those previously reported in the literature, and an expression for the prediction of rate as a function of reactant partial pressure is provided.The rate of reaction of the DCAC intermediate is also discussed.Air is shown to be an optimum oxidant, and an optimum humidity is established.The reaction is shown to proceed indefinitely under dry conditions, supporting the existence of a chlorine radical propagated surface reaction.

Peri, J. B.

, p. 2937 - 2945 (1966)

-

Dickinson,Leermakers

, p. 3852 (1932)

-

IR spectroscopic study of the dichloromethyl peroxyl radical and its deuterated analogs in the argon matrix

Baskir, E. G.,Nefedov, O. M.

, p. 2236 - 2240 (2022/01/22)

The dichloromethyl peroxyl radical (CHCl2OO?) and its deuterated analog formed in the reaction of the corresponding dichloromethyl radicals with O2 were studied by matrix IR spectroscopy. Dichloromethyl radicals are genera

Photocatalytic degradation of gaseous trichloroethylene on porous titanium dioxide pellets modified with copper(II) under visible light irradiation

Tashiro, Keigo,Tanimura, Toshifumi,Yamazaki, Suzuko

, p. 228 - 235 (2019/04/17)

Porous titanium dioxide pellets modified with copper(II) ion (Cu-TiO2) were synthesized by sol-gel method with dialysis for photocatalytic degradation of gaseous trichloroethylene (TCE) under visible light (VL) irradiation. TCE was completely degraded by passing the gas stream (mole fractions of oxygen and TCE were 0.2 and 1.75 × 10?4, respectively) at the flow rate of 25 mL min?1 through 0.2 g of the Cu-TiO2 pellets (Cu content: 0.1 atom%) calcined at 200 °C. TCE was converted mainly to carbon dioxide, dichloroacetic acid (DCAA), and inorganic chlorine species. Relatively small quantities of pentachloroethane (PCA) and trichloroacetaldehyde (TCAH) were detected as products on the Cu-TiO2 surface. Comparison with porous TiO2 pellets under ultraviolet irradiation revealed that more chlorinated products and less carbon dioxide were formed on Cu-TiO2 under VL irradiation. The mineralization of TCE to carbon dioxide was calculated to be only ca. 30.0%. It is noted that DCAA, PCA and TCAH were accumulated on the surface and were extracted with ethyl acetate. The porous Cu-TiO2 pellets show promise as the photocatalyst acting under VL irradiation for converting TCE gas to chlorinated compounds which can be used in industries.

Safe and Efficient Phosgenation Reactions in a Continuous Flow Reactor

Yasukouchi, Hiroaki,Nishiyama, Akira,Mitsuda, Masaru

supporting information, p. 247 - 251 (2018/02/23)

Phosgene is widely used in organic synthesis owing to its high reactivity, utility, and cost efficiency. However, the use of phosgene in batch processes on the industrial scale is challenging owing to its toxicity. An effective method to minimize reaction volumes and mitigate the safety risks associated with hazardous chemicals is the use of flow reactors. Consequently, we have established a flow reaction system using triphosgene and tributylamine, which affords a homogeneous reaction that avoids clogging issues. In addition, we have demonstrated that this methodology can be applied to a wide variety of phosgene reactions, including the preparation of pharmaceutical intermediates, in good to excellent yields.

A fluorescent probe Cou - Bu and its preparation and the ozone application in the

-

Paragraph 0021; 0032; 0033, (2018/07/15)

A fluorescent probe Cou - Bu and its preparation and application of ozone in the detection. The invention provides a can be used for selectively detecting ozone molecules of the fluorescent probe. The main synthetic method is as follows: 7 - amino - 4 - methyl coumarin with triphosgene reaction to obtain the acyl chloride, generated product also and 3 - butene - 1 - ol to undergo esterification reaction, the final generation structure is Compound; under the action of the ozone molecules, generating 7 - amino - 4 - methyl coumarin, by using the difference between the front and the rear of the fluorescent reaction to the selectivity of the ozone molecule detection.

Reactions of Three Lactones with Cl, OD, and O3: Atmospheric Impact and Trends in Furan Reactivity

Ausmeel,Andersen,Nielsen,?sterstr?m,Johnson,Nilsson

, p. 4123 - 4131 (2017/06/23)

Lactones, cyclic esters of hydroxycarboxylic acids, are interesting biofuel candidates as they can be made from cellulosic biomass and have favorable physical and chemical properties for distribution and use. The reactions of γ-valerolactone (GVL), γ-crotonolactone (2(5H)-F), and α-methyl-γ-crotonolactone (3M-2(5H)-F) with Cl, OD, and O3 were investigated in a static chamber at 700 Torr and 298 ± 2 K. The relative rate method was used to determine kGVL+Cl = (4.56 ± 0.51) × 10-11, kGVL+OD = (2.94 ± 0.41) × 10-11, k2(5H)-F+Cl = (2.94 ± 0.41) × 10-11, k2(5H)-F+OD = (4.06 ± 0.073) × 10-12, k3M-2(5H)-F+Cl = (16.1 ± 1.8) × 10-11, and k3M-2(5H)-F+OD = (12.6 ± 0.52) × 10-12, all rate coefficients in units of cm3 molecule-1 s-1. An absolute rate method was used to determine k2(5H)-F+O3 = (6.73 ± 0.18) × 10-20 and k3M-2(5H)-F+O3 = (5.42 ± 1.23) × 10-19 in units of cm3 molecule-1 s-1. Products were identified for reactions of the lactones with Cl. In the presence of O2 the products are formic acid (HCOOH), formyl chloride (CHClO), and phosgene (CCl2O), and also maleic anhydride (C2H2(CO)2O) for 2(5H)-F. In addition both reactions produced a number of unidentified products that likely belong to molecules with the ring-structure intact. A review of literature data for reactions of other furans show that the reactivity of the lactones are generally lower compared to that of corresponding compounds without the carbonyl group.

Process route upstream and downstream products

Process route

tetrachloromethane
56-23-5

tetrachloromethane

(4-nitro-phenyl)-carbamic acid trichloromethyl ester
859807-24-2

(4-nitro-phenyl)-carbamic acid trichloromethyl ester

phosgene
75-44-5

phosgene

4-Nitrophenyl isocyanate
100-28-7

4-Nitrophenyl isocyanate

Conditions
Conditions Yield
(4-nitro-phenyl)-carbamic acid trichloromethyl ester
859807-24-2

(4-nitro-phenyl)-carbamic acid trichloromethyl ester

phosgene
75-44-5

phosgene

4-Nitrophenyl isocyanate
100-28-7

4-Nitrophenyl isocyanate

Conditions
Conditions Yield
at 100 ℃;
C<sub>7</sub>H<sub>7</sub>ClNO<sub>2</sub><sup>(1+)</sup>*Cl<sup>(1-)</sup>

C7H7ClNO2(1+)*Cl(1-)

4-methylpyridine-1-oxide
1003-67-4

4-methylpyridine-1-oxide

phosgene
75-44-5

phosgene

Conditions
Conditions Yield
In dichloromethane; at 15 - 35 ℃; Equilibrium constant; Thermodynamic data; ΔH (at 25 deg C);
tetrachloromethane
56-23-5

tetrachloromethane

molybdenum
7439-98-7

molybdenum

phosgene
75-44-5

phosgene

molybdenum(VI) oxide chloride

molybdenum(VI) oxide chloride

molybdenum(IV) chloride
13320-71-3

molybdenum(IV) chloride

Conditions
Conditions Yield
With oxygen; at 310°C;
tetrachloromethane
56-23-5

tetrachloromethane

phosphorus pentoxide

phosphorus pentoxide

phosgene
75-44-5

phosgene

Conditions
Conditions Yield
In neat (no solvent); byproducts: CO2; heating starting material to 200 - 210°C; the amt. of COCl2 formed depends on P2O5/CCl4 ratio;;
tetrachloromethane
56-23-5

tetrachloromethane

zirconium(IV) oxide
7440-67-7

zirconium(IV) oxide

phosgene
75-44-5

phosgene

oxygen
80937-33-3

oxygen

zirconium(IV) chloride
10026-11-6

zirconium(IV) chloride

Conditions
Conditions Yield
In neat (no solvent); reaction at 1000K; mechanism discussed;; determination by IR;;
In neat (no solvent); reaction at 1000K; mechanism discussed;; determination by IR;;
antimony(III) trioxide

antimony(III) trioxide

phosgene
75-44-5

phosgene

antimony(III) chloride
10025-91-9

antimony(III) chloride

Conditions
Conditions Yield
With tetrachloromethane; at 100°C in sealed tube;
With CCl4; at 100°C in sealed tube;
phosphorus dichloride trifluoride
13454-99-4

phosphorus dichloride trifluoride

Carbonyl fluoride
353-50-4

Carbonyl fluoride

phosgene
75-44-5

phosgene

fluoroformyl chloride
353-49-1

fluoroformyl chloride

Dichlorodifluoromethane
75-71-8

Dichlorodifluoromethane

carbon dioxide
124-38-9,18923-20-1

carbon dioxide

Conditions
Conditions Yield
300°C, further product: CCl4;
tungsten tritaoctoxide

tungsten tritaoctoxide

phosgene
75-44-5

phosgene

tungsten(V) chloride
13470-14-9

tungsten(V) chloride

tungsten(VI) chloride
13283-01-7

tungsten(VI) chloride

Conditions
Conditions Yield
With tetrachloromethane; 240°C; in closed tube;
With CCl4; 240°C; in closed tube;
tetrachloromethane
56-23-5

tetrachloromethane

M-P<sub>2</sub>O<sub>5</sub> (monomeric P<sub>4</sub>O<sub>10</sub>)
16752-60-6

M-P2O5 (monomeric P4O10)

phosgene
75-44-5

phosgene

carbon dioxide
124-38-9,18923-20-1

carbon dioxide

Conditions
Conditions Yield
In neat (no solvent); react. with an excess of CCl4 at 200 °C;;
In neat (no solvent); react. with an excess of CCl4 at 200 °C;;

Global suppliers and manufacturers

Global( 1) Suppliers
  • Company Name
  • Business Type
  • Contact Tel
  • Emails
  • Main Products
  • Country
  • Amadis Chemical Co., Ltd.
  • Business Type:Lab/Research institutions
  • Contact Tel:86-571-89925085
  • Emails:sales@amadischem.com
  • Main Products:29
  • Country:China (Mainland)
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