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Cas Database

79-10-7

79-10-7

Identification

  • Product Name:Acrylic acid

  • CAS Number: 79-10-7

  • EINECS:201-177-9

  • Molecular Weight:72.0636

  • Molecular Formula: C3H4O2

  • HS Code:2916110000

  • Mol File:79-10-7.mol

Synonyms:Acide acrylique;Acroleic acid;Ethylenecarboxylic acid;NSC 4765;Propenoicacid;Vinylformic acid;2-Propenoic acid;Glacial acrylic acid;Propenoic acid;Glacial Acrylic Acid (AA);

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Safety information and MSDS view more

  • Pictogram(s):CorrosiveC, DangerousN

  • Hazard Codes: C:Corrosive;

  • Signal Word:Danger

  • Hazard Statement:H226 Flammable liquid and vapourH302 Harmful if swallowed H312 Harmful in contact with skin H314 Causes severe skin burns and eye damage H332 Harmful if inhaled H400 Very toxic to aquatic life

  • 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. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention. May burn skin or eyes upon short contact. INHALATION: eye and nasal irritation and lacrimation. INGESTION: may cause severe damage to the gastrointestinal tract. (USCG, 1999)Exposure Routes: inhalation, skin absorption, ingestion, skin and/or eye contact Symptoms: Irritation eyes, skin, respiratory system; eye, skin burns; skin sensitization Target Organs: Eyes, skin, respiratory system (NIOSH, 2016) Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organic acids and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Use dry chemical, carbon dioxide, or alcohol foam extinguishers. Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Storage containers and parts of containers may rocket great distances, in many directions. In advanced or massive fires, fire fighting should be done from a safe distance or from a protected location. If a leak or spill has not ignited, use water spray to disperse the vapors. Water spray may be used to flush spills away from exposures and to dilute spills to nonflammable mixtures. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors or shows any signs of deforming), withdraw immediately to a secure position. Special Hazards of Combustion Products: Toxic vapors are generated when heated Behavior in Fire: May polymerize and explode (USCG, 1999)Excerpt from ERG Guide 132P [Flammable Liquids - Corrosive]: Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016) 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: complete protective clothing including self-contained breathing apparatus. Ventilation. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

  • 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. Separated from strong oxidants, strong bases, strong acids and food and feedstuffs. Keep in the dark. Store only if stabilized. Store in an area without drain or sewer access. Storage conditions may vary according to the type of inhibitor used. Refer to the manufacturer's instructions for proper storage conditions. See Notes.Acrylic acid should be stored in a detached, cool, well-ventilated, non-combustible place, and its containers should be protected against physical damage. Acrylic acid can be stored only in vessels lined with glass, stainless steel, aluminum, or polyethylene. In order to inhibit polymerization during transport and storage, 200 ppm MeHQ (the monomethyl ether of hydroquinone) is commonly added to acrylic acid by the manufacturer. The presence of oxygen is required for the inhibitor to be effective. A major concern during the storage of acrylic acid is the avoidance of elevated temperatures as well as freezing, since both can lead to a failure of the inhibitor system. Ideally acrylic acid should be stored within a temperature range of 15 to 25°C.

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 10-hour Time-Weighted Average: 2 ppm (6 mg/cu m) [skin].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 520 Articles be found

Acetylene carbonylation over Ni-containing catalysts: Role of surface structure and active site distribution

Xie, Hao,Lin, Tiejun,Shi, Li,Meng, Xuan

, p. 97285 - 97292 (2016)

Heterogenization of homogeneous catalyst for acetylene carbonylation was carried out by preparing a series of Ni-modified catalysts (Ni-ZSM-5, Ni-IM-5 and Ni-MCM-41). Several important properties of the heterogeneous catalysts were determined by inductively coupled plasma atomic emission spectroscopy (ICP-AES), XPS, XRD, N2 adsorption, pyridine-FTIR, SEM and TGA. Moreover, we used various activity criteria to dissipate perturbing factors, when we focused on the influence of surface structure and active site distribution. The result that Ni-IM-5 had the greatest TOFNi = 5107 g acrylic acid per g Ni per h showed that the surface structure of samples did not influence the catalyst performance significantly. In addition, the highest ratio of nickel sites/acid sites in Ni-MCM-41 represented the best active site distribution. Thus, Ni-MCM-41 has the highest TOFcat = 70.6 g acrylic acid per g cat. per h. Furthermore, stability testing of the catalysts showed the Ni-MCM-41 could be used four times, while others only twice.

A unique nickel-base nitrogen-oxygen bidentate ligand catalyst for carbonylation of acetylene to acrylic acid

Cui, Long,Yang, Xiangui,Zeng, Yi,Chen, Yuntang,Wang, Gongying

, p. 57 - 61 (2019)

A nickel-base nitrogen-oxygen bidentate ligand catalyst was prepared in-situ via the complexation method. Our results show that the ligand with nickel can form a chelate catalyst possessing a ring structure, which exhibits good catalytic performance in the carbonylation reaction of acetylene to acrylic acid (AA). Furthermore, we discovered that, under our optimized conditions, when 8-hydroxyquinoline (HQ) is used as the ligand [c(Ni(OAc)2·4H2O) = 15 × 10?6 mol L?1, n(HQ):n(Ni(OAc)2·4H2O) = 1:1, V(H2O) = 7 mL], 70.1% conversion of acetylene and 92.4% the selectivity of AA is achieved at 200 °C with 8.0 MPa pressure for 30 min. Compared to traditional acetylene carbonylation catalysts and nickel-base phosphine ligand homogeneous complex catalysts, our catalytic system has unique advantages, including no copper, no halogen and no carbon deposition generated during the reaction process. It displays high selectivity and no corrosion of equipment, suggesting that this catalytic system possesses future industrial applications.

Ni-exchanged Y-zeolite: An efficient heterogeneous catalyst for acetylene hydrocarboxylation

Lin, Tie Jun,Meng, Xuan,Shi, Li

, p. 163 - 171 (2014)

A series of Ni-modified Y-zeolites with varying Ni loading in the presence of cupric salt as promoter were studied for acetylene hydrocarboxylation performed in a batch reactor. The catalysts were characterized by elemental analysis, H2-TPR, XRD, NH3-TPD, pyridine-FTIR, SEM, TG-DTG and Raman. It was found that the catalytic activity showed a pronounced dependence on the supports, metal introduction method, promoters and reaction conditions. The nickel species present as charge compensation cations in the zeolite framework constitute the active sites, and the acid sites help to promote the performance of carbonylation. Moreover, two types of coke were observed, and the remarkable reusability of NiY is attributable to the location of the coke outside the zeolite crystals. High catalytic performance was obtained over a NiY(7.0) catalyst with 62 gacrylic acid/(g cat. · h) of yield at 235 °C, 3.6 MPa of initial total pressure and 0.8 mM/l of cupric bromide within 40 min of reaction time. This is the most effective heterogeneous system for synthesizing acrylic acid by carbonylation of acetylene to date.

Exploring the multifunctionality and accessibility of vanadosilicates to produce acrylic acid in one-pot glycerol oxydehydration

Jones, Christopher W.,Lopez-Castillo, Alejandro,Martins, Leandro,Vieira, Luiz H.

, (2020)

Acrylic acid is one of the most attractive products directly produced from glycerol, and many efforts are still made to thoroughly understand the role of different catalytic sites in the reaction. In this work, we prepared Al-free vanadosilicates presenting structures analog to ferrierite and ITQ-6 zeolites (2D and 3D structures). The materials were efficient in catalyzing the one-pot conversion of glycerol to acrylic acid. The different vanadium species in the catalysts had specific roles in each step of the reaction. By exposing samples to humid conditions, dissociative adsorption of water produced hydroxylated sites (O3V-OH-Si) that acted as extrinsic Br?nsted acid sites. The deprotonation energy of these sites was estimated by DFT calculations and found to be close to deprotonation energy of intrinsic Br?nsted acidity of aluminosilicates with the same zeolitic structure, indicating the ability of the active site to dehydrate glycerol to acrolein. The formation of these sites seems to effectively block potential Lewis acidity of the vanadosilicates since acetol, a dehydration side product, was not formed. Spectroscopic data showed changes in oxidation states of vanadium in these sites after the reaction, presenting V5+ and V4+ states, indicating the activity of these sites on the oxidation step during oxidation of acrolein to acrylic acid. By decreasing vanadium content during synthesis, delamination to ITQ-6 was more effective, increasing accessibility and, consequently, the productivity of sites.

COMPETITION BETWEEN DECARBOXYLATION AND ISOMERIZATION IN THE C3H5O2(1+) ENERGY SURFACE. JUSTIFICATION OF THE EXPERIMENTAL RESULTS BY MOLECULAR ORBITAL CALCULATIONS ON THE SOLVATED IONS

Rajadell, Fernando,Planelles, Josep,Tomas, Francisco,Asensio, Gregorio,Miranda, Miguel A.,Sabater, Maria J.

, p. 221 - 226 (1994)

In contrast with recent molecular orbital calculations on the decarboxylation of O-protonated 2-oxetanone, this experimental work indicates that no decarboxylation of this cation occurs in sulphuric acid solution up to 150 deg C, but instead a clean isomerization to protonated acrylic acid takes place.Parallel theoretical work shows that the gas-phase model is too crude to account successfully for the experimental facts obtained in acidic media.However, the latter are well reproduced when the effect of the solvent is taken into account.The present findings do not necessarily invalidate the reaction mechanism currently accepted to explain the rate enhancement and change of stereochemistry accompanying the decarboxylation of 3,4-disubstituted 2-oxetanones under acid catalysis.

Facile sub-/supercritical water synthesis of nanoflake MoVTeNbO:X-mixed metal oxides without post-heat treatment and their catalytic performance

Deng, Luyao,Fan, Yaoxin,Li, Shuangming,Liu, Yongwei,Lu, Zixuan,Yan, Yunong,Yu, Sansan,Zhang, Zhe

, p. 39922 - 39930 (2020)

A fast and simple sub-/supercritical water synthesis method is presented in this work in which MoVTeNbOx-mixed metal oxides with various phase compositions and morphologies could be synthesized without post-heat treatment. It was demonstrated that the system temperature for synthesis had a significant influence on the physico-chemical properties of MoVTeNbOx. Higher temperatures were beneficial for the formation of a mixed crystalline phase containing TeVO4, Te3Mo2V2O17, Mo4O11 and TeO2, which are very different from the crystalline phases of conventional Mo-V-Te-Nb-mixed metal oxides. While at lower temperatures, Mo4O11 was replaced by Te. At high temperature, the as-prepared samples presented distinct nanoflake morphologies with an average size of 10-60 nm in width and exhibited excellent catalytic performances in the selective oxidation of propylene to acrylic acid. It is illustrated that the large specific surface area, presence of Mo4O11 and superficial Mo6+ and Te4+ ions are responsible for the high propylene conversion, while suitable acidic sites and superficial Nb5+ ions improved the selectivity to acrylic acid. This journal is

How important is the (001) plane of M1 for selective oxidation of propane to acrylic acid?

Celaya Sanfiz,Hansen,Sakthivel,Trunschke,Schloegl,Knoester,Brongersma,Looi,Hamid

, p. 35 - 43 (2008)

The role of the (001) crystallographic plane of the M1 phase of MoVTeNb mixed-oxide catalysts in selective oxidation of propane to acrylic acid was addressed by investigating a phase-pure M1 material preferentially exposing this surface. A model catalyst was prepared by complete silylation of M1, followed by breakage of the SiO2-covered needles. Using this approach, the reactivity of the M1 (001) surface was investigated by combining a microreactor study of propane oxidation with high-sensitivity low-energy ion scattering (HS-LEIS). Scanning electron microscopy (SEM) and transmission electron microscopy (TEM) were used to study the shape and microstructure of the model system and verify the surface exposure of the model catalyst. The specific rate of formation of acrylic acid on the model catalyst was found to be similar to that on the phase-pure M1 reference material, indicating that the (001) plane of the M1 crystal structure did not have better catalytic properties compared with the lateral surface of M1 needles in propane oxidation.

The regional hydrolysis of ethyl acrylate to acrylic acid in the rat nasal cavity

Frederick, Clay B.,Udinsky, John R.,Finch, Lavorgie

, p. 49 - 56 (1994)

Cytotoxicity is primarily limited to the olfactory epithelium of the dorsal meatus region of the nasal cavity of rodents following inhalation exposure to acrylic monomers. To investigate the biochemical basis for this effect, three regions of the Fischer F344N rat nasal cavity were evaluated for carboxylesterase activity for the representative acrylic ester, ethyl acrylate. Prior studies have indicated that the rodent olfactory epithelium is sensitive to the cytotoxic effects of short chain organic acids. In this study, no regional difference in carboxylesterase activity was observed between sensitive and non-sensitive regions of olfactory epithelium. Respiratory epithelium (resistant to cytotoxicity) was found to have a much lower rate of carboxylesterase activity than olfactory epithelium. These results suggest that the regional distribution of cytotoxicity observed in the rat nasal cavity at high concentrations of inhaled acrylic monomers may be due in part to the amount of released organic acid following deposition. However, the observation of the same esterase activity in sensitive and nonsensitive olfactory regions suggests that nasal air flow patterns and regional deposition may also be critical factors.

Pd@Zn-MOF-74: Restricting a Guest Molecule by the Open-Metal Site in a Metal-Organic Framework for Selective Semihydrogenation

Wu, Hui Qiong,Huang, Ling,Li, Jian Qiang,Zheng, An Min,Tao, Yuan,Yang, Li Xiao,Yin, Wen Hui,Luo, Feng

, p. 12444 - 12447 (2018)

In this work, we found that the open-metal site in a metal-organic framework (MOF) can be used to enhance such selectivity. Hydrogenation of phenylacetylene over such a catalyst enables ultrahigh styrene selectivity of 92% at full conversion with a turnover frequency of 98.1 h-1. The origin of ultrahigh selectivity, as unveiled by density functional theory calculation, is due to a coordination interaction between the open Zn(II) site and the C≡C bond of phenylacetylene.

Kinetics of osmium(VIII) catalyzed oxidation of allyl alcohol by potassium bromate in aqueous acidic medium-autocatalysis in catalysis

Desai,Halligudi,Nandibewoor

, p. 583 - 589 (1999)

The kinetics of oxidation of allyl alcohol with potassium bromate in the presence of osmium(VIII) catalyst in aqueous acid medium has been studied under varying conditions. The active species of oxidant and catalyst in the reaction were understood to be Bro3- and H2OsO5, respectively. The autocatalysis exhibited by one of the products, that is, Br-, was attributed to complex formation between bromide and osmium(VIII). A composite scheme and rate law were possible. Some reaction constants involved in the mechanism have been evaluated.

Immobilization of rhodococcus AJ270 and use of entrapped biocatalyst for the production of acrylic acid

Colby, John,Snell, David,Black, Gary W.

, p. 655 - 666 (2000)

Rhodococcus AJ270 is adsorbed by Dowex 1 at 15.4 mg dry weight per g resin with maximum amidase specific activity observed at lower loadings. Bacteria form a monolayer on the resin surface, and adsorption is complete within 2 min. AJ270 can be entrapped in agar and agarose gels (optimum loading: 20 mg dry weight bacteria per cm3 gel). Adsorption and entrapment improve amidase thermal stability 3-4 fold, and entrapment shifts the pH optimum from 8 to 7. Adsorbed and free bacteria show similar values for Km and Vmax, but entrapped bacteria have higher Km values. Compared with bacteria adsorbed to Dowex, the activity per cm3 of matrix of agar-entrapped AJ270 is eight-fold higher. In stirred-tank reactors, exposure to acrylic acid reduces the amidase activity of the biocatalyst in the hydrolysis of acrylamide. In column reactors, entrapped AJ270 suffers little reduction in amidase activity against 0.25 M acrylamide over 22 h continuous operation.

Surfactant-assisted synthesis of Mo-V mixed oxide catalysts for upgraded one-step conversion of glycerol to acrylic acid

Rasteiro, Letícia F.,Vieira, Luiz H.,Santilli, Celso V.,Martins, Leandro

, p. 11975 - 11982 (2018)

The catalytic properties of Mo-V mixed oxides hydrothermally synthetized in the presence of ionic surfactants (SDS and CTAB) were investigated in the gas-phase oxidative dehydration of glycerol. The presence of surfactants promoted a change in morphology of MoV2O8 phase, directing to formation of rod-shaped crystals, and, consequently, an increase in macroporosity of materials, generated by intercrystallite spaces, when compared to a reference sample. Rod-like morphology stabilized the MoV2O8 mixed oxide phase during glycerol conversion, avoiding migration of vanadium from crystalline to amorphous phase, like observed in the reference sample, favoring the dynamic of reduction/reoxidation of vanadium and, consequently contributing to an increase in efficiency and stability of the catalyst. Both SDS and CTAB catalysts presented higher productivity of acrylic acid and good catalytic stability, with no coke formation and considerable decrease in COX evolution during 6 h of reaction. SDS presented the best catalytic results with 100% of conversion, 57% of acrylic acid selectivity and 36% of COX selectivity.

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Riiber,Schetelig

, p. 349 (1904)

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Kinetic study of specific base catalyzed hydrolysis of ethyl acrylate in water-ethanol binary system

Sharma, Sangita,Ramani, Jayesh,Bhalodia, Jasmin,Vyas, Bijal

, p. 730 - 736 (2013)

Kinetic study of hydroxide anion catalyzed hydrolysis of ethyl acrylate has been carried in ethanol-water (10-50% v/v) binary systems at the temperature range 30 ± 0.1, 35 ± 0.1, 40 ± 0.1, and 45 ± 0.1 C. Calculated specific rate constant values decreases with increasing proportion of ethanol at all temperatures. The observed retardation of a base catalyzed hydrolysis reaction is explained on the basis of fact that the formation of polarized transition state is disfavored with increase in % of ethanol. The relation between the change in dielectric constant due to variation in binary mixtures and change in specific rate constant are explained on the basis of electrostatic and non electrostatic contributions of solvent mixtures. The variation of ΔG*, ΔH*, ΔS with solvent composition and the specific effect of water on the reaction rate kinetics are also discussed.

Enhancement of acrylic acid yields in propane and propylene oxidation by selective P Doping of MoV(Nb)TeO-based M1 and M2 catalysts

Grasselli,Lugmair,Volpe Jr.,Andersson,Burrington

, p. 33 - 38 (2010)

The selective doping of M1 and M2 phases for the selective oxidation of propane and propylene to acrylic acid (AA) was investigated. A series of catalytic materials for the oxidation of propane were prepared with the general precursor composition Mo1V0.31-Te0.37Nb xPyOn. A first solution was prepared by dissolving ammonium heptamolybdate, ammonium vanadate, and telluric acid in water at 60°C. This solution was allowed to cool to room temperature. A second solution was prepared by dissolving niobic acid in oxalic acid at 60°C. The appropriate amount of the first solution, second solution, and phosphoric acid were mixed and then dried by rotary evaporation. Each catalyst was tested at four different space velocities, starting with the highest, at several reaction temperatures starting at the lowest temperature. Doping of crystalline M1 and M2 phases with P in selective oxidation of propane or propylene enhances significantly the desired AA yields at commercially relevant high hydrocarbon conversions.

Bi4Cu0.2V1.8O11-δ based electrolyte membrane reactor for selective oxidation of propane to acrylic acid

Wang, Jibo,Ji, Baofeng,Chu, Wenling,Zhan, Shijing,Lin, Liwu,Yang, Weishen

, p. 157 - 162 (2010)

An electrochemical membrane reactor using Bi4Cu0.2V1.8O11-δ as a solid electrolyte membrane was employed to investigate the selective oxidation of propane to acrylic acid over a MoV0.3Te0.17Nb0.12O catalyst. By applying an external current to the membrane reactor, the ionic oxygen was pumped to the surface of the MoV0.3Te0.17Nb0.12O catalyst, which exhibited higher conversion of propane and selectivity to acrylic acid than that in the fixed-bed reactor. The results indicate that the enhancement of catalytic performance in the membrane reactor is mainly due to the presence of the lattice oxygen, which has been proved to be necessary for the formation of acrylic acid. Thus, the Au/Bi4Cu0.2V1.8O11-δ/Au/MoVTeNbO membrane reactor achieved a higher conversion of propane (42%) and selectivity to acrylic acid (79.6%) at 380 °C with a 0.6 A current.

V-Zr-P oxide catalysts for highly selective oxidation of propane to acrylic acid

Han, Yi-Fan,Wang, Huai-Ming,Cheng, Hua,Deng, Jing-Fa

, p. 521 - 522 (1999)

V-Zr-P oxide catalysts have been prepared and exhibited high selectivity in the oxidation of propane to acrylic acid.

The multiple benefits of glycerol conversion to acrolein and acrylic acid catalyzed by vanadium oxides supported on micro-mesoporous MFI zeolites

Possato, Luiz G.,Chaves, Thiago F.,Cassinelli, Wellington H.,Pulcinelli, Sandra H.,Santilli, Celso V.,Martins, Leandro

, p. 20 - 28 (2017)

The ZSM-5 zeolite (MFI structure, Si/Al?=?40) was treated using NaOH and either oxalic acid or HCl to obtain hierarchical materials with different characteristics, followed by impregnation with vanadium oxides (V2O5) to generate redox-active sites. The impact of the multiple treatments on the efficiency and stability of the catalysts in the conversion of glycerol to acrolein and acrylic acid was investigated and correlated with catalyst porosity, acidity, and chemical composition. The treated and impregnated V2O5 catalysts were subjected to XRD, 27Al NMR, nitrogen physisorption, TPD-NH3, TG, and UV–Vis analyses, in order to associate the properties of the catalysts with their activities. The studies showed that the catalytic performance of the materials depended on the acidic and textural properties of the zeolites, which influenced both the dispersion of V2O5 and its interaction with the acid sites of the supporting zeolites. All the catalysts provided conversion values exceeding 65%, even after 6?h on glycerol stream. The distribution of products strongly reflected the effects of pore formation, acid treatment with oxalic acid or HCl, and the presence of vanadium oxide. The effects of these modifications resulted in higher selectivity to acrolein and acrylic acid, a reduced rate of coke accumulation in the zeolite, and a longer catalyst lifetime.

Oxidation of Propane to Acrylic Acid on V2O5-P2O5-based Catalysts

Ai, Mamoru

, p. 786 - 787 (1986)

V2O5-P2O5-based oxides, especially V2O5-P2O5-TeO2, are effective catalysts for the partial oxidation of propane to acrylic acid using gaseous oxygen as an oxidant; a yield of 9 molpercent was reached.

Highly Selective Synthesis of Acrylic Acid from Lactide in the Liquid Phase

Nagengast, Jens,Hahn, Simon,Taccardi, Nicola,Kehrer, Matthias,Kadar, Julian,Collias, Dimitris,Dziezok, Peter,Wasserscheid, Peter,Albert, Jakob

, p. 2936 - 2943 (2018)

A new reaction system for the highly selective, hydrobromic acid catalyzed conversion of lactide into acrylic acid under mild conditions is reported. The applied liquid reaction system consists of a temperature-stable bromide-containing ionic liquid and 2-bromopropionic acid as a source of dry HBr, with no volatile organic solvent being used. This allows for the in situ removal of the formed acrylic acid, leading to an unmatched acrylic acid selectivity of over 72 % at full lactide conversion. Accounting for leftover reaction intermediates on the way to acrylic acid, which could be recycled in an elaborate continuous process, the proposed reaction system shows potential for acrylic acid yields well above 85 % in the liquid phase. This opens new avenues for the effective conversion of biogenic lactic acid (e.g., obtained by fermentation from starch) to acrylic acid. The resulting bio-acrylic acid is a highly attractive product for, for example, the diaper industry, where we expect consumers to be especially sensitive to aspects of sustainability.

Hydrothermal synthesis of Mo-V mixed oxides possessing several crystalline phases and their performance in the catalytic oxydehydration of glycerol to acrylic acid

Rasteiro, Letícia F.,Vieira, Luiz H.,Possato, Luiz G.,Pulcinelli, Sandra H.,Santilli, Celso V.,Martins, Leandro

, p. 10 - 18 (2017)

The one-step oxydehydration of glycerol to acrylic acid over molybdenum and vanadium mixed oxides was investigated. The Mo-V oxide catalysts were prepared by a simple hydrothermal method under different synthesis and calcination atmospheres and were characterized by in situ XRD, TPD-NH3, N2 adsorption/desorption, X-ray absorption near vanadium K-edge spectroscopy and thermogravimetry. The catalytic performance of the samples at different temperatures (290, 320 and 350 °C) and under different gas flow compositions (20% O2 in N2, 100% O2, or 100% N2) revealed that the arrangement of the crystallographic structures of the active phases directly influenced the catalytic performance. It was found that the catalysts heat-treated in oxidizing atmosphere gave superior catalytic results comparing with the catalysts heat-treated in inert atmosphere due to the equilibrium between the crystalline phases MoVO5 and Mo4.65V0.35O14 that contains V+4 and V+5. Catalytic oxydehydration at 320 °C under a flow of 100% O2 gave the best performance, achieving selectivity of 33.5% towards acrylic acid and 100% conversion of glycerol.

Hierarchical NaY Zeolites for Lactic Acid Dehydration to Acrylic Acid

Lari, Giacomo M.,Puértolas, Bego?a,Frei, Matthias S.,Mondelli, Cecilia,Pérez-Ramírez, Javier

, p. 1507 - 1514 (2016)

The industrial viability of heterogeneous catalysts for the gas-phase conversion of lactic acid to acrylic acid will strongly depend on their selectivity and durability. Here, we initially screened various aluminum-rich zeolites confirming that NaY is the most efficient catalyst for this reaction. This material was modified by sequential dealumination and alkaline treatment attaining a solid featuring a hierarchical distribution of micro- and mesopores, reduced Lewis acidity, and increased basicity owing to the presence of well-dispersed sodium ions interacting with external siloxy groups, as evidenced by in-depth characterization. These properties were crucial for determining higher selectivity (75 %) and minimizing the activity loss in a 6 h run. Remarkably, the catalyst gained in selectivity and stability upon reuse in consecutive cycles. This was ascribed to the depletion of the stronger basic sites and the clustering of sodium into oxidic particles upon the intermediate calcination.

Selective dehydrosulfurization of 3-mercaptopropionic acid to acrylic acid on silicalite catalyst

Pina, Cristina Della,Falletta, Ermelinda,Rossi, Michele

, p. 456 - 459 (2010)

Dehydrosulfurization of 3-mercaptopropionic acid has been investigated in a fixed bed reactor using a silicalite catalyst in order to recover the hydrocarbon core. Under reductive conditions, acrylic acid was formed in high yield at 350 °C and atmospheric pressure as the desired product along the toxic H2S, whereas, carrying out the reaction in the presence of air, safer dihydrogenpolysulfides resulted as the co-product.

A recyclable heterogeneous-homogeneous-heterogeneous NiO/AlOOH catalysis system for hydrocarboxylation of acetylene to acrylic acid

Li, Yakun,Yan, Lifang,Zhang, Qiaofei,Yan, Binhang,Cheng, Yi

, p. 1634 - 1638 (2020)

Concerns about the high-valued utilization of coal- A nd natural gas-based acetylene has provided particular impetus for exploration of acrylic acid (AA) production via one-step hydrocarboxylation reaction. Motivated by simple recovery, recycling and reuse of the catalyst, we report a high-performance NiO/AlOOH catalyst with AA space-time-yield of 412 gAA gcat.-1 h-1, obtainable by a simple incipient wetness impregnation method. Detailed kinetic and controlled experiments confirmed that nickel species on such a solid catalyst provide a heterogeneous-homogeneous-heterogeneous catalytic cycle where the chelates formed between CO and leached nickel act as the active species. The thorough recovery of leached nickel species improves the catalyst stability greatly. These preliminary findings indicate further prospects for new heterogeneous catalyst design in traditional homogeneous catalytic systems.

Nickel oxide-silica core-shell catalyst for acetylene hydroxycarbonylation

Choi, Hong Sub,Park, Ji Hoon,Bae, Jong Wook,Lee, Jin Hee,Chang, Tae Sun

, p. 86 - 90 (2019)

Acrylic acid and its ester derivatives are important chemicals utilized to synthesize numerous end products. Acrylic acid is industrially produced via propylene oxidation. We report in this study a nickel oxide-silica core-shell catalyst (NiO@SiO2) for acetylene hydroxycarbonylation as an alternative way to synthesize acrylic acid. NiO@SiO2 catalyst provided the higher turnover frequency and yield than commercial nickel oxide catalyst on acetylene hydroxycarbonylation. The carbon monoxide/acetylene ratio influenced more significantly to initial reaction rate than final acrylic acid yield. The silica shell protected the nickel oxide from sintering during reaction, however, the catalyst was deactivated by coke formation, attributed to acetylene decomposition.

-

Kaszuba

, p. 1227 (1945)

-

METHOD FOR MANUFACTURING A NUMBER OF REACTION TUBES FOR PRODUCING (METH)ACRYLIC ACID

-

Paragraph 0176-0201, (2021/03/09)

The present invention relates to a method for producing a plurality of reaction tubes for acrylic acid production. A method for manufacturing a plurality of reaction tubes is provided to minimize pressure difference between a plurality of reaction tubes.

Mo–V–O nanocrystals synthesized in the confined space of a mesoporous carbon

Mukai, Shin R.,Obunai, Ryo,Ogino, Isao,Tamura, Keisuke,Ueda, Wataru

, (2021/08/21)

Ternary Mo–V oxide nanocrystals (Nano-MoVO) were hydrothermally synthesized in the confined space of a mesoporous carbon template and tested in the oxidative dehydrogenation (ODH) of ethane and propane. The synthesized nanocrystals are approximately 60 nm in length, 20 nm in diameter on average, and possess a structure resembling orthorhombic MoVO (Orth-MoVO) as indicated by spectroscopic and microscopy characterization. The Nano-MoVO catalyst has a 5-fold higher mesopore volume and a 4-fold larger external surface area than an Orth-MoVO synthesized by a conventional method (Orth-MoVO) as characterized through N2 adsorption analysis. Nano-MoVO shows similar activation energy in the ODH of ethane compared with other conventional MoVO catalysts. However, Nano-MoVO exhibits significantly higher propane/ethane activation rate ratio and higher propene selectivity even in the absence of elements such as Te and Nb that suppress overoxidation of propane-derived species to COx. The results suggest the benefits of the nanocrystalline morphology to limit overoxidation.

Novel Mo-V Oxide Catalysts with Nanospheres as Templates for the Selective Oxidation of Acrolein to Acrylic Acid

Wang, Weihua,Xu, Wenjie,Song, Weilin,Yang, Bin,Li, Li,Guo, Xuhong,Wu, Lianghua,Liu, Hongxing

, p. 2326 - 2338 (2021/01/11)

Abstract: Novel Mo-V-PMMA and Mo-V-PS catalysts are prepared by addition of hard polymethyl methacrylate (PMMA) and polystyrene (PS) nanospheres into Mo/V compounds in the preparation process, respectively. The catalytic tests in selective oxidation of acrolein reveal that Mo-V-PMMA catalyst shows very high acrolein conversion (99.1%) and the yield of acrylic acid (90.7%). The BET, DLS, SAXS, XRD, XPS, H2-TPR and NH3-TPD measurements reveal that the addition of PMMA and PS nanospheres causes the obvious changes of porous structure, crystal phases composition and chemical properties of catalysts. These differences between Mo-V-PMMA and Mo-V-PS catalysts are attributed to the totally different “real” nano–environment during heat treatment in the high–concentration component mixture. PS nanospheres are in a state of adhesion or agglomeration or not uniformly distributed in the active component solution, while PMMA nanospheres with much better hydrophilicity and monodispersed state promote Mo and V ions more easily and uniformly dispersed in the mixture. Graphic abstract: Novel Mo-V catalysts are prepared by addition of hard polymethyl methacrylate (PMMA) and polystyrene (PS) nanospheres into Mo/V mixture. Obvious changes of porous structure, crystal phases and chemical properties of catalysts are caused by the nanospheres introduction, showing very high acrolein conversion (99.1%) and the yield of acrylic acid (90.7%) in selective oxidation of acrolein.[Figure not available: see fulltext.].

Parahydrogen-Induced Polarization Relayed via Proton Exchange

Them, Kolja,Ellermann, Frowin,Pravdivtsev, Andrey N.,Salnikov, Oleg G.,Skovpin, Ivan V.,Koptyug, Igor V.,Herges, Rainer,H?vener, Jan-Bernd

supporting information, p. 13694 - 13700 (2021/09/07)

The hyperpolarization of nuclear spins is a game-changing technology that enables hitherto inaccessible applications for magnetic resonance in chemistry and biomedicine. Despite significant advances and discoveries in the past, however, the quest to establish efficient and effective hyperpolarization methods continues. Here, we describe a new method that combines the advantages of direct parahydrogenation, high polarization (P), fast reaction, and low cost with the broad applicability of polarization transfer via proton exchange. We identified the system propargyl alcohol + pH2 → allyl alcohol to yield 1H polarization in excess of P ≈ 13% by using only 50% enriched pH2 at a pressure of ≈1 bar. The polarization was then successfully relayed via proton exchange from allyl alcohol to various target molecules. The polarizations of water and alcohols (as target molecules) approached P ≈ 1% even at high molar concentrations of 100 mM. Lactate, glucose, and pyruvic acid were also polarized, but to a lesser extent. Several potential improvements of the methodology are discussed. Thus, the parahydrogen-induced hyperpolarization relayed via proton exchange (PHIP-X) is a promising approach to polarize numerous molecules which participate in proton exchange and support new applications for magnetic resonance.

Cu(II)-Based Ionic Liquid Supported on SBA-15 Nanoparticles Catalyst for the Oxidation of Various Alcohols into Carboxylic Acids in the Presence of CO2

Chen, Yanwu,Hou, Dejian,Lin, Litian,Peng, Qi,Sadeghzadeh, Seyed Mohsen

, (2021/07/26)

In this paper, we have produced carboxylic acids by the oxidation of various alcohols in the presence of CO2 using SBA-15/IL supported Cu(II) (SBA-15/IL/Cu(II)) as nanocatalyst. The obtained products showed to have excellent yields by taking into account of SBA-15/IL/Cu(II) nanocatalyst. In addition, the analysis of EDX, SEM, TGA, TEM, XPS, and FT-IR showed the heterogeneous structure of SBA-15/IL/Cu (II) catalyst. It is determined that, after using SBA-15 excess, the catalytic stability of the system was enhanced. Moreover, hot filtration provided a full vision in the heterogeneous catalyst nature. The recycling as well as reuse of the catalyst were studied in cases of coupling reactions many times. Moreover, we have studied the mechanism of the coupling reactions. Graphic Abstract: [Figure not available: see fulltext.]

Process route upstream and downstream products

Process route

p-nitrophenyl acrylate
2123-85-5

p-nitrophenyl acrylate

acrylic acid
79-10-7

acrylic acid

Conditions
Conditions Yield
With water; at 24 ℃; Kinetics; different pH;
4-(4-methoxy-phenyl)-4-oxo-butyric acid
3153-44-4

4-(4-methoxy-phenyl)-4-oxo-butyric acid

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

acrylic acid
79-10-7

acrylic acid

Conditions
Conditions Yield
With disodium hydrogenphosphate; sodium acetate; permanganate(VII) ion; at 29.85 ℃; pH=6.5; Further Variations:; Temperatures; Reagents; Kinetics;
3-Bromopropionic acid
590-92-1

3-Bromopropionic acid

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

acrylic acid
79-10-7

acrylic acid

Conditions
Conditions Yield
beim Erhitzen unter gewoehnlichem Druck;
3-iodopropanoic acid
141-76-4

3-iodopropanoic acid

hydrogen iodide
10034-85-2

hydrogen iodide

acrylic acid
79-10-7

acrylic acid

Conditions
Conditions Yield
3-iodopropanoic acid
141-76-4

3-iodopropanoic acid

hydrogen iodide
10034-85-2

hydrogen iodide

acrylic acid
79-10-7

acrylic acid

Conditions
Conditions Yield
beim Destillieren;
3-iodopropanoic acid
141-76-4

3-iodopropanoic acid

water
7732-18-5

water

hydrogen iodide
10034-85-2

hydrogen iodide

acrylic acid
79-10-7

acrylic acid

Conditions
Conditions Yield
Conditions
Conditions Yield
With water; oxygen; catalyst (composed of Mo, Bi, Fe, Co, W, Si, and K at respective molar ratios of 12:1.0:1:5:0.5:1:0.06) obtained by evaporation of water solution of salts and silica sol; powder was fired under current of air at 460 C;
5.8 %Chromat.
Conditions
Conditions Yield
Hoveyda-Grubbs catalyst second generation; In dichloromethane; at 40 ℃; for 24h; under 750.075 Torr; Inert atmosphere;
13%
13%
Conditions
Conditions Yield
Hoveyda-Grubbs catalyst second generation; In dichloromethane; at 40 ℃; for 24h; under 562.556 Torr; Product distribution / selectivity; Inert atmosphere;
31%
5%
21%
Acid Orange 7

Acid Orange 7

ethylbenzene
100-41-4,27536-89-6

ethylbenzene

(1S)-camphor
464-48-2,68546-28-1

(1S)-camphor

2,6-di-tert-butyl-4-methyl-phenol
128-37-0

2,6-di-tert-butyl-4-methyl-phenol

2-benzylpropionaldehyde
5445-77-2

2-benzylpropionaldehyde

1,3-bis(3-phenoxyphenoxy)benzene
2455-71-2

1,3-bis(3-phenoxyphenoxy)benzene

(+)-isothujone
471-15-8

(+)-isothujone

acetic acid
64-19-7,77671-22-8

acetic acid

acrylic acid
79-10-7

acrylic acid

Conditions
Conditions Yield
With zinc(II) oxide; Reagent/catalyst; Concentration; pH-value; Sonication; Darkness;

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