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Cas Database

107-10-8

107-10-8

Identification

  • Product Name:Propylamine

  • CAS Number: 107-10-8

  • EINECS:203-462-3

  • Molecular Weight:59.1112

  • Molecular Formula: C3H9N

  • HS Code:2921.19 Oral, rat LD50: 570 mg/kg

  • Mol File:107-10-8.mol

Synonyms:Propylamine(8CI);1-Aminopropane;1-Propylamine;Mono-n-propylamine;Monopropylamine;NSC7490;Propan-1-ylamine;n-Propylamine;1-Propanamine;

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Safety information and MSDS view more

  • Pictogram(s):FlammableF,CorrosiveC

  • Hazard Codes: F:Flammable;

  • Signal Word:Danger

  • Hazard Statement:H225 Highly flammable liquid and vapourH290 May be corrosive to metals H302 Harmful if swallowed H311 Toxic in contact with skin H314 Causes severe skin burns and eye damage H331 Toxic if inhaled H335 May cause respiratory irritation

  • 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 immediately for medical attention. In case of skin contact First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Refer immediately for medical attention. In case of eye contact Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention. If swallowed Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention. INHALATION: Mucous membrane and respiratory tract irritation. Tracheitis, bronchitis, pneumonitis, and pulmonary edema. EYES: Severe corneal damage or complete eye destruction. SKIN: Single drop-deep necrosis. INGESTION: Corrosive to G.I. tract. (USCG, 1999) Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mg/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . /Organic bases/Amines and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Use water spray, dry chemical, "alcohol resistant" foam, or carbon dioxide. Use water spray to keep fire-exposed containers cool. Solid streams of water may be ineffective and spread material. Special Hazards of Combustion Products: Extreme danger, enter with great care. Thermal decomposition may produce nitrogen oxides, CO and/or CO 2 . Behavior in Fire: Keep away from heat and open flame; can react vigorously. (USCG, 1999) 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. Remove all ignition sources. Evacuate danger area! Consult an expert! Personal protection: gas-tight chemical protection suit including self-contained breathing apparatus. 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. Overspread/spill with/ sufficient sodium bisulfate and sprinkle /with/ water. /Ethylamine/

  • 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. Provision to contain effluent from fire extinguishing. Fireproof. Separated from strong oxidants, strong acids and food and feedstuffs. Dry. Well closed. Store in an area without drain or sewer access.Outside or detached storage is prefered. Avoid oxidizing material, acids, and sources of halogen. Store in a cool, dry, well-ventilated location.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological 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 141 Articles be found

Spectroscopy of Hydrothermal Reactions, Part 26: Kinetics of Decarboxylation of Aliphatic Amino Acids and Comparison with the Rates of Racemization

Li, Jun,Brill, Thomas B.

, p. 602 - 610 (2003)

The kinetics of decarboxylation of six α-amino acids (glycine, alanine, aminobutyric acid, valine, leucine, and isoleucine) and β-aminobutyric acid were studied in aqueous solution at 310-330 deg C and 275 bar over the pH25 range 1.5-8.5 by using an in situ FT-IR spectroscopy flow reactor. Based on the rate of formation of CO2, the first-order or pseudo-first-order rate constants were obtained along with the Arrhenius parameters. The decarboxylation rates of amino acids follow the order Gly > Leu ca. Ile ca. Val > Ala > α-Aib > β-Aib. Differences in the concentration between 0.05 and 0.5 m had only a minor effect on the decarboxylation rate. The effect of the position of the amino group on the decarboxylation rate was investigated for α-, β-, and γ-aminobutyric acid and the order was found to be α > β >> γ. Although the pH dependence is complex, the decarboxylation rates of α-amino acids qualitatively have the inverse trend of the racemization rates.

Boyd et al.

, p. 2283,2284, 2287, 2288 (1971)

Merging constitutional and motional covalent dynamics in reversible imine formation and exchange processes

Kovaricek, Petr,Lehn, Jean-Marie

, p. 9446 - 9455 (2012)

The formation and exchange processes of imines of salicylaldehyde, pyridine-2-carboxaldehyde, and benzaldehyde have been studied, showing that the former has features of particular interest for dynamic covalent chemistry, displaying high efficiency and fast rates. The monoimines formed with aliphatic α,ω-diamines display an internal exchange process of self-transimination type, inducing a local motion of either "stepping-in- place" or "single-step" type by bond interchange, whose rate decreases rapidly with the distance of the terminal amino groups. Control of the speed of the process over a wide range may be achieved by substituents, solvent composition, and temperature. These monoimines also undergo intermolecular exchange, thus merging motional and constitutional covalent behavior within the same molecule. With polyamines, the monoimines formed execute internal motions that have been characterized by extensive one-dimensional, two-dimensional, and EXSY proton NMR studies. In particular, with linear polyamines, nondirectional displacement occurs by shifting of the aldehyde residue along the polyamine chain serving as molecular track. Imines thus behave as simple prototypes of systems displaying relative motions of molecular moieties, a subject of high current interest in the investigation of synthetic and biological molecular motors. The motional processes described are of dynamic covalent nature and take place without change in molecular constitution. They thus represent a category of dynamic covalent motions, resulting from reversible covalent bond formation and dissociation. They extend dynamic covalent chemistry into the area of molecular motions. A major further step will be to achieve control of directionality. The results reported here for imines open wide perspectives, together with other chemical groups, for the implementation of such features in multifunctional molecules toward the design of molecular devices presenting a complex combination of motional and constitutional dynamic behaviors.

N,N-Bis(trimethylsilyl)methoxymethylamine as a Convenient Synthetic Equivalent for +CH2NH2: Primary Aminomethylation of Organometallic Compounds

Morimoto, Toshiaki,Takahashi, Toshio,Sekiya, Minoru

, p. 794 - 795 (1984)

The introduction of the primary aminomethyl unit at carbon through N,N-bis(trimethylsilyl)aminomethylation of Grignard and organolithium compounds can be achieved in good yield using N,N-bis(trimethylsilyl)methoxymethylamine (1).

-

Johnson,Degering

, p. 3194 (1939)

-

-

Coleman,Hermanson,Johnson

, p. 1896 (1937)

-

-

Boyer et al.

, p. 325 (1956)

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Water-soluble platinum and palladium nanoparticles modified with thiolated β-cyclodextrin

Alvarez, Julio,Liu, Jian,Roman, Esteban,Kaifer, Angel E.

, p. 1151 - 1152 (2000)

Pt and Pd nanoparticles can be modified with surface-attached cyclodextrin receptors leading to water-soluble materials that exhibit catalytic activity for the hydrogenation of allylamine.

Rice husk-SiO2supported bimetallic Fe-Ni nanoparticles: as a new, powerful magnetic nanocomposite for the aqueous reduction of nitro compounds to amines

Ghadermazi, Mohammad,Moradi, Setareh,Mozafari, Roya

, p. 33389 - 33400 (2020)

This paper reports a novel green procedure for immobilization of bimetallic Fe/Ni on amorphous silica nanoparticles extracted from rice husk (RH-SiO2). The heterogeneous nanocomposite (Fe/Ni?RH-SiO2) was identified using SEM, EDX, TEM, BET, H2-TPR, TGA, XRD, VSM, ICP-OES, and FT-IR analyses. The Fe/Ni?RH-SiO2nanocomposite was applied as a powerful catalyst for the reduction of structurally diverse nitro compounds with sodium borohydride (NaBH4) in green conditions. This procedure suggests some benefits such as green chemistry-based properties, short reaction times, non-explosive materials, easy to handle, fast separation and simple work-up method. The catalyst was separated by an external magnet from the reaction mixture and was reused for 9 successive cycles with no detectable changes of its catalytic efficiency.

Reduced reactivity of amines against nucleophilic substitution via reversible reaction with carbon dioxide

Mohammed, Fiaz S.,Kitchens, Christopher L.

, (2016)

The reversible reaction of carbon dioxide (CO2) with primary amines to form alkyl-ammonium carbamates is demonstrated in this work to reduce amine reactivity against nucleophilic substitution reactions with benzophenone and phenyl isocyanate. The reversible formation of carbamates has been recently exploited for a number of unique applications including the formation of reversible ionic liquids and surfactants. For these applications, reduced reactivity of the carbamate is imperative, particularly for applications in reactions and separations. In this work, carbamate formation resulted in a 67% reduction in yield for urea synthesis and 55% reduction for imine synthesis. Furthermore, the amine reactivity can be recovered upon reversal of the carbamate reaction, demonstrating reversibility. The strong nucleophilic properties of amines often require protection/de-protection schemes during bi-functional coupling reactions. This typically requires three separate reaction steps to achieve a single transformation, which is the motivation behind Green Chemistry Principle #8: Reduce Derivatives. Based upon the reduced reactivity, there is potential to employ the reversible carbamate reaction as an alternative method for amine protection in the presence of competing reactions. For the context of this work, CO2 is envisioned as a green protecting agent to suppress formation of n-phenyl benzophenoneimine and various n-phenyl-n-alky ureas.

-

Frieman,Jurewicz

, p. 1800 (1969)

-

Supramolecular solid-gas complexes: A thermodynamic approach

Grechin, Alexander G.,Buschmann, Hans-Juergen,Schollmeyer, Eckhard

, p. 6499 - 6501 (2007)

(Table Presented) Phasing up to complex problems: A thermodynamic approach based on solution data has been proposed for the determination of the stability of gas complexes and elucidation of the selectivity of gas binding. Stability constants, reaction enthalpies, and entropies for the complexation of gaseous guests (n-alkylamines) by solid macrocyclic hosts (β-cyclodextrin, cucurbit[6]uril) were calculated by using the Born-Haber type cycle (see picture).

Insight into the mechanism of hydrogenation of amino acids to amino alcohols catalyzed by a heterogeneous MoOx-modified Rh catalyst

Tamura, Masazumi,Tamura, Riku,Takeda, Yasuyuki,Nakagawa, Yoshinao,Tomishige, Keiichi

, p. 3097 - 3107 (2015)

Hydrogenation of amino acids to amino alcohols is a promising utilization of natural amino acids. We found that MoOx-modified Rh/SiO2 (Rh-MoOx/SiO2) is an efficient heterogeneous catalyst for the reaction at low temperature (323 K) and the addition of a small amount of MoOx drastically increases the activity and selectivity. Here, we report the catalytic potential of Rh-MoOx/SiO2 and the results of kinetic and spectroscopic studies to elucidate the reaction mechanism of Rh-MoOx/SiO2 catalyzed hydrogenation of amino acids to amino alcohols. Rh-MoOx/SiO2 is superior to previously reported catalysts in terms of activity and substrate scope. This reaction proceeds by direct formation of an aldehyde intermediate from the carboxylic acid moiety, which is different from the reported reaction mechanism. This mechanism can be attributed to the reactive hydride species and substrate adsorption caused by MoOx modification of Rh metal, which results in high activity, selectivity, and enantioselectivity.

-

Rooley et al.

, p. 1082 (1952)

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Catalytic Reductions and Tandem Reactions of Nitro Compounds Using in Situ Prepared Nickel Boride Catalyst in Nanocellulose Solution

Prathap, Kaniraj Jeya,Wu, Qiong,Olsson, Richard T.,Dinér, Peter

, p. 4746 - 4749 (2017)

A mild and efficient method for the in situ reduction of a wide range of nitroarenes and aliphatic nitrocompounds to amines in excellent yields using nickel chloride/sodium borohydride in a solution of TEMPO-oxidized nanocellulose in water (0.01 wt %) is described. The nanocellulose has a stabilizing effect on the catalyst, which increases the turnover number and enables low loading of nickel catalyst (0.1-0.25 mol % NiCl2). In addition, two tandem protocols were developed in which the in situ formed amines were either Boc-protected to carbamates or further reacted with an epoxide to yield β-amino alcohols in excellent yields.

-

Mukaiyama,Fujita

, p. 54 (1956)

-

Amination of alcohols with ammonia in water over Rhin catalyst

Takanashi, Tsukasa,Nakagawa, Yoshinao,Tomishige, Keiichi

, p. 822 - 824 (2014)

Amination of various C3 alcohols such as 1,2-propanediol with ammonia was catalyzed by RhIn/C in water while Rh/C was totally inactive. Activated carbon FAC-10 was the best support in terms of activity and resistance to metal leaching. In the amination of 1,2-propanediol, RhIn/C produced amino alcohols in 68% total selectivity and 38% conversion. XRD and TEM measurements showed that RhIn alloy particle with size of 34 nm was formed on the carbon support.

Sustainable hydrogenation of aliphatic acyclic primary amides to primary amines with recyclable heterogeneous ruthenium-tungsten catalysts

Coeck, Robin,Berden, Sarah,De Vos, Dirk E.

, p. 5326 - 5335 (2019)

The hydrogenation of amides is a straightforward method to produce (possibly bio-based) amines. However current amide hydrogenation catalysts have only been validated in a rather limited range of toxic solvents and the hydrogenation of aliphatic (acyclic) primary amides has rarely been investigated. Here, we report the use of a new and relatively cheap ruthenium-tungsten bimetallic catalyst in the green and benign solvent cyclopentyl methyl ether (CPME). Besides the effect of the Lewis acid promotor, NH3 partial pressure is identified as the key parameter leading to high primary amine yields. In our model reaction with hexanamide, yields of up to 83% hexylamine could be achieved. Beside the NH3 partial pressure, we investigated the effect of the catalyst support, PGM-Lewis acid ratio, H2 pressure, temperature, solvent tolerance and product stability. Finally, the catalyst was characterized and proven to be very stable and highly suitable for the hydrogenation of a broad range of amides.

CoFe2O4?SiO2-NH2-CoII NPs: An effective magnetically recoverable catalyst for Biginelli reaction

Allahresani, Ali,Hemmat, Kaveh,Nasseri, Mohammad Ali,Sangani, Mehri Mohammadpour

, (2020)

Biginelli reaction entails acid-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) with simply-accessible initial substances, specifically, aldehyde, urea, and active methylene compound. DHPMs have stimulated a resurgence of attention in the previous two decades because of their broad-ranging pharmacological actions and the existence of varied all-natural products. Currently, green methods to asymmetric Biginelli reaction have been researched for anti-inflammatory DHPMs. In materials chemistry, DHPMs are increasingly decision applications in the creation of materials like polymers, adhesives, fabric dyes, etc. In light of the simplicity by which the Biginelli reaction is conducted, numerous interesting prospects expect its exploitation in variety fields. CoFe2O4?SiO2-NH2-CoII is herein turned out to be an effective catalyst at a three-component Biginelli reaction. The yield of the corresponding DHPMs was rather large (20 cases; average 92 percent). Finally, we herein suggest a procedure that shows lots of advantages and benefits such as the whole lack of solvents, mild reaction conditions, comparatively short reaction times. Also, CoFe2O4?SiO2-NH2-CoII NPs catalyst has been readily recovered from the reaction combination and reused, without the decrease of catalytic action.

Chemosensor for the optical detection of aliphatic amines and diamines

Reinert, Susanne,Mohr, Gerhard J.

, p. 2272 - 2274 (2008)

Two new chemosensor dyes with either one or two trifluoroacetophenone recognition moieties have been investigated in terms of reversibly interacting with amines and diamines. The Royal Society of Chemistry.

Comparison of the Activity and Lifetime of Raney Nickel and Nickel Boride in the Hydrogenation of Various Functional Groups

Schreifels, John A.,Maybury, P. Calvin,Swartz, William E.

, p. 1263 - 1269 (1981)

Nickel borides (Ni2B) are prepared by the reduction of a nickel salt with sodium borohydride.These materials have been shown to be active hydrogenation catalysts.The activity and lifetime of a P-1.50 nickel boride catalyst, which is prepared in a 50percent water/ethanol solvent, are reported for the hydrogenation of unsaturated carbon and nitrogen bonds and for aldehydes.The data are compared to those obtained for similar reductions which employ Raney nickel as the catalyst.The nickel boride is more active and productive than Raney nickel in the hydrogenation of hexene,cyclohexene, and acrylonitrile.The properties of the two catalysts are similar for the reduction of cinnamaldehyde, 2-ethylhexanal, and benzaldehyde.The data for the reduction of nitrobenzene, adiponitrile, and propionitrile indicate that the nickel boride is more susceptible to nitrogen poisoning than Raney nickel.

Palladium/Graphitic Carbon Nitride (g-C3N4) Stabilized Emulsion Microreactor as a Store for Hydrogen from Ammonia Borane for Use in Alkene Hydrogenation

Han, Chenhui,Meng, Peng,Waclawik, Eric R.,Zhang, Chao,Li, Xin-Hao,Yang, Hengquan,Antonietti, Markus,Xu, Jingsan

, p. 14857 - 14861 (2018)

Direct hydrogenation of C=C double bonds is a basic transformation in organic chemistry which is vanishing from simple practice because of the need for pressurized hydrogen. Ammonia borane (AB) has emerged as a hydrogen source through its safety and high hydrogen content. However, in conventional systems the hydrogen liberated from the high-cost AB cannot be fully utilized. Herein, we develop a novel Pd/g-C3N4 stabilized Pickering emulsion microreactor, in which alkenes are hydrogenated in the oil phase with hydrogen originating from AB in the water phase, catalysed by the Pd nanoparticles at the interfaces. This approach is advantageous for more economical hydrogen utilization over conventional systems. The emulsion microreactor can be applied to a range of alkene substrates, with the conversion rates achieving >95 % by a simple modification.

Zoerner,Huettig

, p. 145,156 (1933)

Postcolumn Photolysis of Pesticides for Fluorometric Determination by High-Performance Liquid Chromatography

Miles, Carl J.,Moye, H. Anson

, p. 220 - 226 (1988)

A high-performance liquid chromatography postcolumn reaction detector that employs UV photolysis with an optional reaction by using o-phthalaldehyde-2-mercaptoethanol (OPA-MERC) followed by fluorescence detection was found to be useful for several classes of pesticides.In the presence of the OPA-MERC reagent, most carbamates, carbamoyl oximes, carbamothioic acids, and substituted ureas gave a sensitive response while the response of dithiocarbamates, phenylamides, and phenylcarbamates varied.The response of most of the pesticides tested was significantly affected bythe solvent used.Method detection limits for aldicarb sulfoxide, aldicarb, propoxur, thiram, and neburon in groundwater were 2.5, 2.3, 3.3, 3.8, and 2.0 νg/L, respectively.In the absence of OPA-MERC reagent, several of the substituted aromatic compounds also gave strong fluorescence after photolysis.This detector is applicable to a broad range of nitrogenous pesticides.

Kinetic study of the reaction between iodide and N-chloramines

Antelo, J. M.,Arce, F.,Campos, J.,Parajo, M.

, p. 391 - 396 (1996)

We carried out a kinetic study of the reaction between iodide ion and various primary N-chloramines and found it to be first-order in the latter.Experiments also showed the rate constant for the reaction to be directly proportional to the iodide and hydrogen ion concentrations.The influence of the concentration reveals the presence of general acid catalysis processes.

-

Crum,Robinson

, p. 561,562 (1943)

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Mechanism of β-lactam ring opening in cephalosporins

Page,Proctor

, p. 3820 - 3825 (1984)

The mechanism of the aminolysis of cephalosporins is a stepwise process. A tetrahedral intermediate is formed by the reversible addition of the amine to the beta -lactam carbonyl carbon. Expulsion of the attacking amine from the tetrahedral intermediate occurs faster than fission of the beta -lactam C-N bond. The reaction proceeds by trapping the intermediate with base. Expulsion of a leaving group at C-3 prime in cephalosporins is not concerted with nucleophilic attack of the amine on the beta -lactam carbonyl carbon and makes little difference to the rate of beta -lactam C-N bond fission.

-

Friedmann,Jurewicz

, p. 1254 (1968)

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Development and Application of Efficient Ag-based Hydrogenation Catalysts Prepared from Rice Husk Waste

Unglaube, Felix,Kreyenschulte, Carsten Robert,Mejía, Esteban

, p. 2583 - 2591 (2021/04/09)

The development of strategies for the sustainable management and valorization of agricultural waste is of outmost importance. With this in mind, we report the use of rice husk (RH) as feedstock for the preparation of heterogeneous catalysts for hydrogenation reactions. The catalysts were prepared by impregnating the milled RH with a silver nitrate solution followed by carbothermal reduction. The composition and morphology of the prepared catalysts were fully assessed by IR, AAS, ICP-MS, XPS, XRD and STEM techniques. This novel bio-genic silver-based catalysts showed excellent activity and remarkable selectivity in the hydrogenation of nitro groups in both aromatic and aliphatic substrates, even in the presence of reactive functionalities like halogens, carbonyls, borate esters or nitriles. Recycling experiments showed that the catalysts can be easily recovered and reused multiple times without significant drop in performance and without requiring re-activation.

Highly selective synthesis of primary amines from amide over Ru-Nb2O5 catalysts

Guo, Wanjun,Guo, Yong,Jia, Hongyan,Liu, Xiaohui,Pan, Hu,Wang, Yangang,Wang, Yanqin,Xia, Qineng

supporting information, (2021/12/22)

Amines are an important class of compounds in natural products and medicines. The universal availability of amides provides a potential way for the synthesis of amines. Herein, Ru/Nb2O5 catalyst is demonstrated to be highly efficient and stable for the selective hydrogenation of propionamide to propylamine (as a model reaction), with up to 91.4% yield of propylamine under relatively mild conditions. Results from XPS analyses, CO chemisorption, TEM images and DRIFTS spectra revealed that the unique properties of Nb2O5 can effectively activate the C=O group of amides, and the smaller Ru particles on Nb2O5 could further promote the activation, leading to superior catalytic performance of Ru/Nb2O5 for amide hydrogenation. Meanwhile, reducing the surface acidity of Nb2O5 can greatly inhibit the side reactions to by-products, and further enhance the selectivity to amine. Moreover, this catalytic system is also applicable for the hydrogenation of a variety of amides and provides high potential for the industrial production of primary amines from amides.

Indirect reduction of CO2and recycling of polymers by manganese-catalyzed transfer hydrogenation of amides, carbamates, urea derivatives, and polyurethanes

Liu, Xin,Werner, Thomas

, p. 10590 - 10597 (2021/08/20)

The reduction of polar bonds, in particular carbonyl groups, is of fundamental importance in organic chemistry and biology. Herein, we report a manganese pincer complex as a versatile catalyst for the transfer hydrogenation of amides, carbamates, urea derivatives, and even polyurethanes leading to the corresponding alcohols, amines, and methanol as products. Since these compound classes can be prepared using CO2as a C1 building block the reported reaction represents an approach to the indirect reduction of CO2. Notably, these are the first examples on the reduction of carbamates and urea derivatives as well as on the C-N bond cleavage in amides by transfer hydrogenation. The general applicability of this methodology is highlighted by the successful reduction of 12 urea derivatives, 26 carbamates and 11 amides. The corresponding amines, alcohols and methanol were obtained in good to excellent yields up to 97%. Furthermore, polyurethanes were successfully converted which represents a viable strategy towards a circular economy. Based on control experiments and the observed intermediates a feasible mechanism is proposed.

Catalyst for producing 3-aminopropanol by hydrogenating 3-hydroxypropionitrile and preparation method thereof

-

Paragraph 0114; 0115; 0116-0118; 0126, (2020/06/09)

The invention discloses a catalyst for producing 3-aminopropanol by hydrogenating 3-hydroxypropionitrile. The catalyst is characterized in that the catalyst comprises an active component and a carrier, wherein the active component comprises active metal elements; the active metal elements comprise M and Re; M is selected from at least one of Ni, Co and Cu; M accounts for 5.0-50.0% of the weight ofthe catalyst; Re accounts for 0.1-15.0% of the weight of the catalyst; and the carrier is selected from at least one of inorganic porous materials. The catalyst has high catalytic activity and selectivity.

Process route upstream and downstream products

Process route

ethanol
64-17-5

ethanol

trimethyl(n-propylamino)silane
18182-24-6

trimethyl(n-propylamino)silane

ethyl trimethylsilyl ether
1825-62-3

ethyl trimethylsilyl ether

Conditions
Conditions Yield
In benzene; at 30 ℃; for 5h; Rate constant; Equilibrium constant; Mechanism;
complex of α-cyclodextrin with n-propylamine

complex of α-cyclodextrin with n-propylamine

alpha cyclodextrin
10016-20-3

alpha cyclodextrin

Conditions
Conditions Yield
In alkaline aq. solution; at 25 ℃; pH=11.60; Equilibrium constant;
α-Hydroxy-N-propylphenylacetamide
104749-84-0

α-Hydroxy-N-propylphenylacetamide

Conditions
Conditions Yield
3-benzyloxypropionitrile
6328-48-9

3-benzyloxypropionitrile

3-benzyloxypropylamine
16728-64-6

3-benzyloxypropylamine

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
at 65 ℃;
diethyl ether
60-29-7,927820-24-4

diethyl ether

3-benzyloxypropionitrile
6328-48-9

3-benzyloxypropionitrile

3-benzyloxypropylamine
16728-64-6

3-benzyloxypropylamine

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
at 35 ℃;
piperazine
110-85-0

piperazine

2-Amino-1-propanol
6168-72-5

2-Amino-1-propanol

N-(1-aminomethyl-2-hydroxyethyl)amine
2811-20-3

N-(1-aminomethyl-2-hydroxyethyl)amine

(RS)-2-methylpiperazine
109-07-9

(RS)-2-methylpiperazine

isopropylamine
75-31-0

isopropylamine

1,2-diaminopropan
78-90-0,10424-38-1

1,2-diaminopropan

3-amino-2-propanol
78-96-6,1674-56-2

3-amino-2-propanol

methylamine
74-89-5

methylamine

Conditions
Conditions Yield
With ammonia; hydrogen; catalyst obtained by prereduction from precursor whose catalytically active composition before the reduction with hydrogen comprised 13% by weight of Cu, calculated as CuO, 28% by weight of NI, calculated as NiO, 28% by weight of Co, calculated as CoO and 31% by weight of Zr, calculated as ZrO2; In water; at 250 ℃; under 37503.8 - 225023 Torr; Product distribution / selectivity; Autoclave;
pyridine
110-86-1

pyridine

5-Methylene-2-[propylcarbamoyl-(2-thiophen-2-yl-acetylamino)-methyl]-5,6-dihydro-2H-[1,3]thiazine-4-carboxylic acid

5-Methylene-2-[propylcarbamoyl-(2-thiophen-2-yl-acetylamino)-methyl]-5,6-dihydro-2H-[1,3]thiazine-4-carboxylic acid

cefaloridine
50-59-9

cefaloridine

Conditions
Conditions Yield
With potassium chloride; In water; at 30 ℃; Equilibrium constant;
propan-1-ol
71-23-8

propan-1-ol

i-Amyl alcohol
123-51-3

i-Amyl alcohol

ammonia
7664-41-7

ammonia

3-methyl-N-(3-methylbutyl)-1-butanamine
544-00-3

3-methyl-N-(3-methylbutyl)-1-butanamine

isopentyl-propyl-amine
78579-58-5

isopentyl-propyl-amine

di-n-propylamine
142-84-7

di-n-propylamine

Conditions
Conditions Yield
at 330 ℃;
1,3-dipropylurea
623-95-0

1,3-dipropylurea

sodium p-toluenesulfonamide
18522-92-4

sodium p-toluenesulfonamide

4-methyl-N-( propylcarbamoyl)benzenesulfonamide
24570-88-5

4-methyl-N-( propylcarbamoyl)benzenesulfonamide

Conditions
Conditions Yield
at 150 ℃; for 6h; Product distribution; other time;;
87%
at 150 ℃; for 6h;
87%
Propyl-thiocarbamic acid; compound with propylamine
64221-20-1

Propyl-thiocarbamic acid; compound with propylamine

carbon oxide sulfide
463-58-1

carbon oxide sulfide

1,3-dipropylurea
623-95-0

1,3-dipropylurea

Conditions
Conditions Yield
at 124 ℃; Thermodynamic data; ΔS (excit.)=-44,77; E*;

Global suppliers and manufacturers

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  • Simagchem Corporation
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  • Main Products:110
  • Country:China (Mainland)
  • Chemwill Asia Co., Ltd.
  • Business Type:Manufacturers
  • Contact Tel:021-51086038
  • Emails:sales@chemwill.com
  • Main Products:30
  • Country:China (Mainland)
  • EAST CHEMSOURCES LIMITED
  • Business Type:Manufacturers
  • Contact Tel:86-532-81906761
  • Emails:josen@eastchem-cn.com
  • Main Products:97
  • Country:China (Mainland)
  • Amadis Chemical Co., Ltd.
  • Business Type:Lab/Research institutions
  • Contact Tel:86-571-89925085
  • Emails:sales@amadischem.com
  • Main Products:29
  • Country:China (Mainland)
  • Career Henan Chemical Co
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-371-86658258
  • Emails:purchase@coreychem.com
  • Main Products:137
  • Country:China (Mainland)
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