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Cas Database

96-48-0

96-48-0

Identification

Synonyms:1,4-Butanolide;1-Oxacyclopentan-2-one;2,3,4,5-Tetrahydro-2-furanone;2-Oxolanone;2-Oxotetrahydrofuran;4,5-Dihydro-2(3H)-furanone;4-Butanolide;4-Deoxytetronicacid;4-Hydroxybutanoic acid lactone;4-Hydroxybutyric acid lactone;Butanoicacid, 4-hydroxy-, g-lactone;Butyric acid lactone;Butyrolactone;Dihydro-2(3H)-furanone;NIH 10540;NSC 4592;Paint Clean G;Tetrahydro-2-furanone;g-BL;g-Butalactone;g-Butyrolactone;g-Butyryllactone;g-Hydroxybutyric acid lactone;1,4-Butyrolactone;gamma-Butyrolactone;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn,F

  • Signal Word:Danger

  • Hazard Statement:H302 Harmful if swallowedH318 Causes serious eye damage H336 May cause drowsiness or dizziness

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. 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. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers 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. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • 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 460 Articles be found

Production of γ-butyrolactone from biomass-derived 1,4-butanediol over novel copper-silica nanocomposite

Hwang, Dong Won,Kashinathan, Palraj,Lee, Jong Min,Lee, Jeong Ho,Lee, U-Hwang,Hwang, Jin-Soo,Hwang, Young Kyu,Chang, Jong-San

, p. 1672 - 1675 (2011)

γ-Butyrolactone was produced highly selectively from biomass-derived 1,4-butanediol by vapor-phase dehydrocyclization over novel copper-silica nanocomposite catalyst. Compared with usual Cu(12)/SiO2, the highly Cu-loaded SiO2 nanocomposite (80 wt%) exhibited high catalyst performance with 98% yield on 400 h stream without significant deactivation even in the absence of H2.

Light-Promoted Minisci Coupling Reaction of Ethers and Aza Aromatics Catalyzed by Au/TiO2 Heterogeneous Photocatalyst

Li, Zhanchong,Wu, Liangying,Guo, Jiabao,Shao, Yifei,Song, Yang,Ding, Yuzhou,Zhu, Li,Yao, Xiaoquan

, p. 3671 - 3678 (2021)

In this paper, Au/TiO2 nanocomposite was synthesized and utilized as highly efficient and green photocatalyst for organic reactions. A sheet-like anatase titanium dioxide material with a highly active (001) crystal plane was prepared via a solvothermal method. Gold nanoparticles were then loaded on the surface of TiO2 by a liquid-phase reduction method to give an Au/TiO2 material with good photocatalytic activity. The Au/TiO2 nanocomposite was utilized as a photocatalyst to develop a light-promoted Minisci oxidative coupling reaction of ether and aza aromatics by using oxygen as green oxidant and only catalytic amount of acid as additive. The protocol shows a good functional group tolerance as well as good to excellent yields for various substrates. With mechanistic studies, Au/TiO2 nanocomposite proved to be an efficient photocatalyst to activate C?H bond via a SEO approach of heteroatoms. Moreover, the solid semiconductor photocatalyst shows good recycling performance, could be easily recovered and reused without significant decrease in yield.

Synthesis and metal binding properties of N-alkylcarboxyspiropyrans

Perry, Alexis,Kousseff, Christina J.

, p. 1542 - 1550 (2017)

Spiropyrans bearing an N-alkylcarboxylate tether are a common structure in dynamic, photoactive materials and serve as colourimetric/fluorimetric cation receptors. In this study, we describe an efficient synthesis of spiropyrans with 2–12 carbon atom alkylcarboxylate substituents, and a systematic analysis of their interactions with metal cations using 1H NMR and UV-visible spectroscopy. All N-alkylcarboxyspiropyrans in this study displayed a strong preference for binding divalent metal cations and a modest increase in M2+ binding affinity correlated with increased alkycarboxylate tether length.

-

Friess,Frankenburg

, p. 2679 (1952)

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Nikishin et al.

, (1973)

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Peroxyl Radical Reactions in Water Solution: A Gym for Proton-Coupled Electron-Transfer Theories

Amorati, Riccardo,Baschieri, Andrea,Morroni, Gloria,Gambino, Rossana,Valgimigli, Luca

, p. 7924 - 7934 (2016)

The reactions of alkylperoxyl radicals with phenols have remained difficult to investigate in water. We describe herein a simple and reliable method based on the inhibited autoxidation of water/THF mixtures, which we calibrated against pulse radiolysis. With this method we measured the rate constants kinh for the reactions of 2-tetrahydrofuranylperoxyl radicals with reference compounds: urate, ascorbate, ferrocenes, 2,2,5,7,8-pentamethyl-6-chromanol, Trolox, 6-hydroxy-2,5,7,8-tetramethylchroman-2-acetic acid, 2,6-di-tert-butyl-4-methoxyphenol, 4-methoxyphenol, catechol and 3,5-di-tert-butylcatechol. The role of pH was investigated: the value of kinh for Trolox and 4-methoxyphenol increased 11- and 50-fold from pH 2.1 to 12, respectively, which indicate the occurrence of a SPLET-like mechanism. H(D) kinetic isotope effects combined with pH and solvent effects suggest that different types of proton-coupled electron transfer (PCET) mechanisms are involved in water: less electron-rich phenols react at low pH by concerted electron-proton transfer (EPT) to the peroxyl radical, whereas more electron-rich phenols and phenoxide anions react by multi-site EPT in which water acts as proton relay. Radical kinetics: A simple and reliable method to measure the kinetics of peroxyl radical reactions in water is described (see figure). The proton-coupled electron transfer from a variety of compounds was investigated. Electron-poorer phenols react by concerted electron-proton transfer (EPT or CPET), whereas electron-richer phenols and phenoxide anions react by multi-site EPT (separated CPET) in which water acts as proton relay, similarly to the chemistry of radical enzymes.

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Nikishin et al.

, (1971)

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Highly dispersed ruthenium nanoparticle-embedded mesoporous silica as a catalyst for the production of γ-butyrolactone from succinic anhydride

Chung, Sang-Ho,Eom, Hee-Jun,Kim, Min-Sung,Lee, Myung Suk,Lee, Kwan-Young

, p. 7701 - 7706 (2013)

In this study, a novel, strategic method was developed for the synthesis of a mesoporous silica catalyst embedded with ruthenium nanoparticles (RuNPs/SiO2) by combining the polyol and modified sol-gel methods. By applying this new procedure, uniformly synthesized ruthenium nanoparticles with an average size of 3.8 nm and 95% spherical shape were highly dispersed in the mesoporous silica support material. Coordinated carbonyl groups of PVP remaining from the synthesis of the RuNPs were effectively removed by the thermal treatment (calcined at 573 K for 4 h) and the sythesized RuNPs/SiO2 catalysts were reduced under hydrogen at 20 bar for 2 h. These catalysts were analyzed using transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR), N2 adsorption-desorption, and X-ray diffraction (XRD). After the thermal treatment and the reduction procedure, the size and shape of the embedded RuNPs were nearly unchanged, and the catalyst was active in the liquid-phase hydrogenation of succinic anhydride (SAN) to selectively form γ-butyrolactone (GBL) with a maximum yield of 90.1%. This novel catalyst preparation is a potentially useful method for the synthesis of metal nanoparticles as heterogeneous catalysts. Copyright

Convergent Cascade Catalyzed by Monooxygenase–Alcohol Dehydrogenase Fusion Applied in Organic Media

Huang, Lei,Aalbers, Friso S.,Tang, Wei,R?llig, Robert,Fraaije, Marco W.,Kara, Selin

, p. 1653 - 1658 (2019)

With the aim of applying redox-neutral cascade reactions in organic media, fusions of a type II flavin-containing monooxygenase (FMO-E) and horse liver alcohol dehydrogenase (HLADH) were designed. The enzyme orientation and expression vector were found to influence the overall fusion enzyme activity. The resulting bifunctional enzyme retained the catalytic properties of both individual enzymes. The lyophilized cell-free extract containing the bifunctional enzyme was applied for the convergent cascade reaction consisting of cyclobutanone and butane-1,4-diol in different microaqueous media with only 5 % (v/v) aqueous buffer without any addition of external cofactor. Methyl tert-butyl ether and cyclopentyl methyl ether were found to be the best organic media for the synthesis of γ-butyrolactone, resulting in about 27 % analytical yield.

REACTION OF SPIRO ORTHO ESTERS WITH POLAR REAGENTS

Zhidkova, N. V.,Kobryanskii, V. M.,Turovskaya, L. M.

, p. 1462 - 1465 (1986)

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REARRANGEMENT OF 2-BUTYNE-1,4-DIOL TO BUTYROLACTONE CATALYZED BY RUTHENIUM COMPLEXES

Shvo, Youval,Blum, Yigal,Reshep, Deborah

, p. C79 - C81 (1982)

The isomerization of 2-butyne-1,4-diol to butyrolactone catalysed by ruthenium complexes is described.

Modification of γ-aminobutyric Acid with Acylacetylenes: Stereoselective C-Vinylation of the Primary Adducts and Transformation to Acylpyridines

Glotova, Tatyana E.,Dvorko, Marina Yu.,Ushakov, Igor A.,Shabalin, Dmitrii A.,Schmidt, Elena Yu.,Trofimov, Boris A.

, p. 314 - 316 (2012)

Primary N-C adducts of γ-aminobutyric acid (GABA) to acylacetylenes undergo mild stereoselective C-vinylation by another acylacetylene molecule to afford (2E,4Z)-4-acyl-5-aminoalka-2,4-dien-1-one-type diadducts in 83-92% yields. The latter cyclize to acyl

Au/TiO2 as high efficient catalyst for the selective oxidative cyclization of 1,4-butanediol to γ-butyrolactone

Huang, Jie,Dai, Wei-Lin,Li, Hexing,Fan, Kangnian

, p. 69 - 76 (2007)

Au/TiO2 catalysts prepared by the deposition-precipitation method showed excellent activity and selectivity in the oxidative cyclization of 1,4-butanediol to γ-butyrolactone, with high yields (>99%) under mild conditions (413 K, 1.25 MPa air). Catalysts with 3-8% gold loading and calcined at 573-673 K were all highly active for the formation of γ-butyrolactone, as demonstrated by XRD, TEM, XPS, ICP and UV-vis DRS results. It is concluded that highly dispersed small (2-10 nm) gold particles are formed with the surface enrichment of gold. The ratio of cationic gold to metallic gold depends on the treatment temperature. These findings, combined with those of the activity tests, lead to the conclusion that the surface metallic nanosized gold particles are active sites. The catalyst can be reused with no drop in activity or selectivity.

Microwave-assisted reduction of levulinic acid with alcohols producing γ-valerolactone in the presence of a Ru/C catalyst

Al-Shaal, Mohammad Ghith,Calin, Marc,Delidovich, Irina,Palkovits, Regina

, p. 65 - 68 (2016)

γ-Valerolactone can be synthesized by reduction of levulinic acid and its esters in the presence of secondary alcohols as hydrogen donors and Ru/C as catalyst. The reaction rate increases when using microwave heating. Quantitative formation of γ-valerolactone was observed within 25 min at 160 °C under microwave heating based on levulinic acid and i-propanol. The reaction appears to proceed via a dehydrogenation-hydrogenation sequence.

Gas-phase hydrogenation of maleic anhydride to γ-butyrolactone over Cu-CeO2-Al2O3 catalyst at atmospheric pressure: Effects of the residual sodium and water in the catalyst precursor

Yu, Yang,Zhan, Wangcheng,Guo, Yun,Lu, Guanzhong,Adjimi, Souheila,Guo, Yanglong

, p. 392 - 397 (2014)

Cu-CeO2-Al2O3 catalysts were prepared by the co-precipitation method with different washing operations during the preparation process for the purpose of controlling the contents of the residual sodium and water in the catalyst precursors. Cu-CeO2-Al2O3 catalysts were characterized by ICP-AES, XRD, SEM, nitrogen sorption, N2O chemisorption, Raman spectroscopy and H2-TPR. Effects of the residual sodium and water in the catalyst precursor on the catalytic performance of Cu-CeO2-Al2O3 catalyst for gas-phase hydrogenation of maleic anhydride to γ-butyrolactone at atmospheric pressure, and the structure-activity relationships were investigated. The results show that the residual water and sodium in the form of Na2CO3 in the catalyst precursor lead to a decrease in Cu dispersion and Cu surface area, which is disadvantageous to the catalytic performance and stability. Washing step of the residual sodium in the catalyst precursor with the deionized water and then removing step of the residual water using azeotropy distillation shows a great improvement in the stability of Cu-CeO2-Al2O3 catalyst, in which 100% of conversion of maleic anhydride and 100% of selectivity to γ-butyrolactone were maintained for 12 h.

Selenium-doped TiO2 as an efficient photocatalyst for the oxidation of tetrahydrofuran to γ-butyrolactone using hydrogen peroxide as oxidant

Padmalatha, Patnam,Khatri, Praveen K.,Jain, Suman L.

, p. 1405 - 1409 (2013)

Selenium-doped TiO2 has been used for the first time as efficient photocatalyst for the oxidation of tetrahydrofuran by using hydrogen peroxide as oxidant, affording γ-butyrolactone (GBL) in excellent yield with higher selectivity. TiO2-doped with selenium showed greater visible absorption and exhibited superior photocatalytic activity than undoped TiO2. The prepared catalyst was subjected to reflux in Millipore water in order to remove the surface-bound selenium species. After this treatment, the catalyst did not show any leaching and showed efficient recycling with consistent catalytic efficiency. Georg Thieme Verlag Stuttgart · New York.

CATALYTIC ENANTIOTOPOS DIFFERENTIATING DEHYDROGENATION OF PROCHIRAL DIOLS USING RUTHENIUM COMPLEX WITH DIOP

Ishii, Youichi,Osakada, Kohtaro,Ikariya, Takao,Saburi, Masahiko,Yoshikawa, Sadao

, p. 1179 - 1182 (1982)

Optically active δ- and γ-lactones are obtained by the homogeneous catalytic dehydrogenation of prochiral diols using Ru2Cl4((-)-DIOP)3 in the presence of benzalacetone as a hydrogen acceptor and triethylamine.

Atomically dispersed Pd catalysts for the selective hydrogenation of succinic acid to γ-butyrolactone

Zhang, Chi,Chen, Lifang,Cheng, Hongye,Zhu, Xuedong,Qi, Zhiwen

, p. 55 - 61 (2016)

Heterogeneous palladium catalysts with high atom-efficiency offer practical value for selective hydrogenation. Here, we prepared atomically dispersed Pd species supported on γ-AlOOH nanosheets (Pd/γ-AlOOH), which contain clusters and dominated single atoms. Even with an extremely low amount of Pd loading, the catalytic activity of 0.1Pd/γ-AlOOH leads to 50.3% of succinic acid conversion at 4 h. At the time, the succinic acid conversion reaches 90.7% and 97.1%, and the selectivity to γ-butyrolactone is high up to 96.9% and 93.8% over 0.5Pd/γ-AlOOH and 1.0Pd/γ-AlOOH, respectively. The supported Pd single atom (Pd1/γ-AlOOH) Exhibits 30- and 1100-fold increase in the catalytic activity compared with the supported clusters Pd13/γ-AlOOH and Pd55/γ-AlOOH for the selective hydrogenation of succinic acid to γ-butyrolactone, respectively. Analysis of the structural properties confirms that Pd single atoms on γ-AlOOH (0 1 0) surface have high adsorption energy, which is in agreement with catalytic efficiency. In addition, Pd single atoms in the catalyst 0.2Pd/γ-AlOOH account for 86.6% of the overall catalytic activity and can serve as the most efficient catalytic active sites.

Oxidative heterocyclization of 1,4-butanediol to 4-butanolide

Seleznev,Zorina,Trifonova,Zorin,Rakhmankulov

, p. 1064 - 1065 (2002)

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Oka

, p. 12 (1961)

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Hydrolysis of Spiro Derivatives that Undergo No Shrinkage on Polymerization

Tagoshi, Hirotaka,Endo, Takeshi

, p. 945 - 947 (1989)

Acid catalysed hydrolyses of spiroorthoeters (1, 2a, 2b, and 2c and spirocarbonates (3 and 4) were carried out to give the corresponding ring-opening reaction products.The ring-cleavage modes of these spiro derivatives depended on the structure of intermediate cations.

Magnetic Co/Al2O3 catalyst derived from hydrotalcite for hydrogenation of levulinic acid to γ-valerolactone

Long, Xiangdong,Sun, Peng,Li, Zelong,Lang, Rui,Xia, Chungu,Li, Fuwei

, p. 1512 - 1518 (2015)

The efficient hydrogenation of levulinic acid (LA) to γ-valerolactone (GVL) over a hydrotalcite-derived non-precious metal Co/Al2O3 catalyst was achieved. Its core-shell structure and a strong interaction between Co and Al species stabilized the Co particles against leaching and sintering. This magnetic non-precious metal catalyst showed a comparable catalytic performance to a commercial Ru/C for the liquid hydrogenation of LA. It was easily separated from the reaction medium with an external magnet. The catalyst exhibited excellent recyclability, complete LA conversion and >99% GVL selectivity, and would be useful in a large scale biorefinery.

A novel route for synthesis of γ-butyrolactone through the coupling of hydrogenation and dehydrogenation

Zhu, Yu-Lei,Xiang, Hong-Wei,Wu, Gui-Sheng,Bai, Liang,Li, Yong-Wang

, p. 254 - 255 (2002)

A coupling process of the hydrogenation of maleic anhydride and the dehydrogenation of 1,4-butanediol has been invented for the synthesis of γ-butyrolactone over a Cu-Zn catalyst, realizing optimal hydrogen utilization and better energy efficiency.

A novel production of γ-butyrolactone catalyzed by ruthenium complexes

Hara, Yoshinori,Kusaka, Haruhiko,Inagaki, Hiroko,Takahashi, Kazunari,Wada, Keisuke

, p. 188 - 197 (2000)

The two-stage hydrogenation of maleic anhydride (MAH) in the liquid phase yielded γ-butyrolactone (GBL). The first stage was the hydrogenation of MAH to succinic anhydride (SAH) and the second stage was the subsequent hydrogenation of SAH to GBL which was studied using a homogeneous catalyst. In the hydrogenation of SAH, a novel ruthenium catalyst system composed of Ru(acac)3, P(octyl)3, and p-toluenesulfonic acid (p-TsOH) was developed exhibiting excellent catalytic performance, with > 95% selectivity for GBL and higher activity than that reported in the literature. p-TsOH was significant in enhancing the reaction rate and improving selectivity. A structural change in the Ru complexes was induced by p-TsOH resulting in the cationic exchange which showed higher catalyst activity. It also prevented the undesired side reaction catalyzed by free P(octyl)3, resulting in high selectivity for GBL. The process which yielded GBL features the external preparation method of the Ru complex, the coupling reaction, and the separation to remove water (a product of hydrogenation of SAH) to increase the reaction rate. To recover > 90% of the catalyst, a catalyst recovery system was developed.

OXIDATION OF CYCLOBUTANONES TO γ-BUTYROLACTONES WITH HYDROGEN PEROXIDE IN 2,2,2-TRIFLUOROETHANOL

Matsumoto, Masakatsu,Kobayashi, Hisako

, p. 2443 - 2447 (1986)

Cyclobutanones were selectively oxidized to yield γ-butyrolactones with hydrogen peroxide in 2,2,2-trifluoroethanol.

Synthesis and radical polymerization of methacrylate endowed with bicyclobis(γ-butyrolactone) moiety through methylene linker

Yamasaki, Ryu,Sudo, Atsushi,Endo, Takeshi

, p. 2462 - 2468 (2015)

A series of methacrylates bearing bicyclobis(γ-butyrolactone) (BBL) moiety were synthesized and radically polymerized to afford the corresponding poly(methacrylate)s bearing BBL moiety in the side chain, with expecting that the high polarity and rigidity of BBL would be inherited by the polymers. The resulting polymers were soluble in polar aprotic solvents such as dimethyl sulfoxide and N,N-dimethylformamide because of the high polarity of the BBL moiety. The glass transition temperatures (Tg) of the polymers depended on the length of methylene linker that tethered the methacrylate and BBL moieties, making the use of shorter linkers lead to higher Tgs.

Routes to Heterotrinuclear Metal Siloxide Complexes for Cooperative Activation of O2

Braun-Cula, Beatrice,Herwig, Christian,Hoof, Santina,Limberg, Christian,Wind, Marie-Louise

, (2020)

The assembly of heterometallic complexes capable of activating dioxygen is synthetically challenging. Here, we report two different approaches for the preparation of heterometallic superoxide complexes [PhL2CrIII-η1-O2][MX]2 (PhL = -OPh2SiOSiPh2O-, MX+ = [CoCl]+, [ZnBr]+, [ZnCl]+) starting from the CrII precursor complex [PhL2CrII]Li2(THF)4. The first strategy proceeds via the exchange of Li+ by [MX]+ through the addition of MX2 to [PhL2CrII]Li2(THF)4 before the reaction with dioxygen, whereas in the second approach a salt metathesis reaction is undertaken after O2 activation by adding MX2 to [PhL2CrIII-η1-O2]Li2(THF)4. The first strategy is not applicable in the case of redox-active metal ions, such as Fe2+ or Co2+, as it leads to the oxidation of the central chromium ion, as exemplified with the isolation of [PhL2CrIIICl][CoCl]2(THF)3. However, it provided access to the hetero-bimetallic complexes [PhL2CrIII-η1-O2][MX]2 ([MX]+ = [ZnBr]+, [ZnCl]+) with redox-inactive flanking metals incorporated. The second strategy can be applied not only for redox-inactive but also for redox-active metal ions and led to the formation of chromium(III) superoxide complexes [PhL2CrIII-η1-O2][MX]2 (MX+ = [ZnCl]+, [ZnBr]+, [CoCl]+). The results of stability and reactivity studies (employing TEMPO-H and phenols as substrates) as well as a comparison with the alkali metal series (M+ = Li+, Na+, K+) confirmed that although the stability is dependent on the Lewis acidity of the counterions M and the number of solvent molecules coordinated to those, the reactivity is strongly dependent on the accessibility of the superoxide moiety. Consequently, replacement of Li+ by XZn+ in the superoxides leads to more stable complexes, which at the same time behave more reactive toward O-H groups. Hence, the approaches presented here broaden the scope of accessible heterometallic O2 activating compounds and provide the basis for further tuning of the reactivity of [RL2CrIII-η1-O2]M2 complexes.

Simultaneous synthesis of aniline and γ-butyrolactone from nitrobenzene and 1,4-butanediol over Cu-CoOx-MgO catalyst via catalytic hydrogen transfer process: Effect of calcination temperature

Kannapu, Hari Prasad Reddy,Park, Young-Kwon,Vaddeboina, Veeralakshmi

, (2022/01/26)

This study examined a hydrogen transfer reaction from 1,4-butanediol to nitrobenzene for γ-butyrolactone and aniline simultaneously over Cu-CoOx-MgO catalysts. The catalyst was developed by co-precipitation followed by metal hydroxycarbonate mixing and calcination at three different temperatures (500, 700, and 900 °C). The hydrogenation of nitrobenzene to aniline and the dehydrogenation of 1,4-butanediol to γ-butyrolactone was accomplished in a gas-phase fixed-bed continuous reactor system at 250 °C. The catalyst Cu-CoOx-MgO-500 calcined at 500 °C showed outstanding performance because of the higher copper dispersion and negligible spinel species (CuCo2O4 /MgCo2O4) compared to the other two catalysts. The order of activity decreased with increasing calcination temperature from 500° to 900°C. The activity trend followed the order, Cu-CoOx-MgO-500 > Cu-CoOx-MgO-700 > Cu-CoOx-MgO-900. The effect of calcination on the catalytic properties was analyzed by atomic absorption spectroscopy elemental analysis, Brunauer-Emmett-Teller surface area, N2O pulse chemisorption, temperature-programmed reduction-H2, X-ray diffraction, and X-ray photoelectron spectroscopy. The results showed that Cu-CoO-MgO-500 exhibited more active copper sites (Cu0/Cu+1) and optimal metal-support interactions that decrease the reduction temperature of copper. On the other hand, Cu-Co and Mg-Co spinel (CuCo2O4/MgCo2O4) content, which adversely affects the catalyst activity, increased with increasing calcination temperature. In summary, simultaneous hydrogenation and dehydrogenation reactions via hydrogen transfer reactions have potential commercial applications.

Ru/SiO2 Catalyst for Highly Selective Hydrogenation of Dimethyl Malate to 1,2,4-Butanetriol at Low Temperatures in Aqueous Solvent

Chen, Can,Jiang, Junxiang,Li, Guangci,Li, Xuebing,Wang, Da,Wang, Zhong,Yu, Pei

, (2022/01/12)

Catalytic selective hydrogenation of esterified malic acid to produce 1,2,4-butanetriol (1,2,4-BT) using H2 as the reducing reagent suffers from the low 1,2,4-BT selectivity. Here, Ru/SiO2 catalyst was employed for selective hydrogenation of dimethyl malate (DM) to produce 1,2,4-BT, which gave abnormal high DM conversion (100%) and 1,2,4-BT selectivity (92.4%) in aqueous solvent at 363?K, especially, the 1,2,4-BT yield even is higher than the optimal catalyst reported (Ru-Re, 79.8%). The reaction pathways for the DM hydrogenation on Ru/SiO2 were also proposed, suggesting that extremely high 1,2,4-BT selectivity require for the much high hydrogenation rates at low temperatures, where side-reaction transesterification rates are relatively low. The extremely high hydrogenation activity and 1,2,4-BT selectivity on Ru/SiO2 in aqueous solvent at low temperatures arise from that H2O may coordinate to Ru2+ and prevent the reduction of Ru2+ to Ru under high H2 pressure. Ru/SiO2 surface presents abundant Ru2+ in aqueous solvent, can activate H2 through heterolytic cleavage mode to form hydride, which can significantly increase hydrogenation rates of C = O groups at low temperatures. In addition, the activity and 1,2,4-BT selectivity on Ru/SiO2 catalyst only reduced by 2.3% and 2.6%, respectively over a period of 550?h. Graphical Abstract: [Figure not available: see fulltext.]

Dehydrogenative ester synthesis from enol ethers and water with a ruthenium complex catalyzing two reactions in synergy

Ben-David, Yehoshoa,Diskin-Posner, Yael,Kar, Sayan,Luo, Jie,Milstein, David,Rauch, Michael

supporting information, p. 1481 - 1487 (2022/03/07)

We report the dehydrogenative synthesis of esters from enol ethers using water as the formal oxidant, catalyzed by a newly developed ruthenium acridine-based PNP(Ph)-type complex. Mechanistic experiments and density functional theory (DFT) studies suggest that an inner-sphere stepwise coupled reaction pathway is operational instead of a more intuitive outer-sphere tandem hydration-dehydrogenation pathway.

Catalytic behaviour of the Cu(I)/L/TEMPO system for aerobic oxidation of alcohols - a kinetic and predictive model

Abu-Radaha, Batool,Al-Hunaiti, Afnan,Repo, Timo,Wraith, Darren

, p. 7864 - 7871 (2022/04/09)

Here, we disclose a new copper(i)-Schiff base complex series for selective oxidation of primary alcohols to aldehydes under benign conditions. The catalytic protocol involves 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO), N-methylimidazole (NMI), ambient air, acetonitrile, and room temperature. This system provides a straightforward and rapid pathway to a series of Schiff bases, particularly, the copper(i) complexes bearing the substituted (furan-2-yl)imine bases N-(4-fluorophenyl)-1-(furan-2-yl)methanimine (L2) and N-(2-fluoro-4-nitrophenyl)-1-(furan-2-yl)methanimine (L4) have shown excellent yields. Both benzylic and aliphatic alcohols were converted to aldehydes selectively with 99% yield (in 1-2 h) and 96% yield (in 16 h). The mechanistic studies via kinetic analysis of all components demonstrate that the ligand type plays a key role in reaction rate. The basicity of the ligand increases the electron density of the metal center, which leads to higher oxidation reactivity. The Hammett plot shows that the key step does not involve H-abstraction. Additionally, a generalized additive model (GAM, including random effect) showed that it was possible to correlate reaction composition with catalytic activity, ligand structure, and substrate behavior. This can be developed in the form of a predictive model bearing in mind numerous reactions to be performed or in order to produce a massive data-set of this type of oxidation reaction. The predictive model will act as a useful tool towards understanding the key steps in catalytic oxidation through dimensional optimization while reducing the screening of statistically poor active catalysis.

Dehydrogenative alcohol coupling and one-pot cross metathesis/dehydrogenative coupling reactions of alcohols using Hoveyda-Grubbs catalysts

?zer, Halenur,Arslan, Dilan,?ztürk, Bengi ?zgün

, p. 5992 - 6000 (2021/04/12)

In this study,in situformed ruthenium hydride species that were generated from Grubbs type catalysts are used as efficient catalysts for dehydrogenative alcohol coupling and sequential cross-metathesis/dehydrogenative coupling reactions. The selectivity of Grubbs first generation catalysts (G1) in dehydrogenative alcohol coupling reactions can be tuned for the ester formation in the presence of weak bases, while the selectivity can be switched to the β-alkylated alcohol formation using strong bases. The performance of Hoveyda-Grubbs 2nd generation catalyst (HG2) was improved in the presence of tricyclohexylphosphine for the selective synthesis of ester derivatives with weak and strong bases in quantitative yields. Allyl alcohol was used as self and cross-metathesis substrate for the HG2 catalyzed sequential cross-metathesis/dehydrogenative alcohol coupling reactions to obtain γ-butyrolactone and long-chain ester derivatives in quantitative yields.

Process route upstream and downstream products

Process route

dimethyl cis-but-2-ene-1,4-dioate
624-48-6

dimethyl cis-but-2-ene-1,4-dioate

2-methoxytetrahydrofuran
13436-45-8

2-methoxytetrahydrofuran

4-butanolide
96-48-0

4-butanolide

propan-1-ol
71-23-8

propan-1-ol

1-methoxy-1,4-butanediol

1-methoxy-1,4-butanediol

2-(4'-hydroxybutoxy)-tetrahydrofuran
64001-06-5

2-(4'-hydroxybutoxy)-tetrahydrofuran

4-hydroxy-butanoic acid 4-hydroxybutyl ester

4-hydroxy-butanoic acid 4-hydroxybutyl ester

Butane-1,4-diol
110-63-4

Butane-1,4-diol

4-hydroxybutyraldehyde
25714-71-0

4-hydroxybutyraldehyde

methyl 4-hydroxybutanoate
925-57-5

methyl 4-hydroxybutanoate

butan-1-ol
71-36-3

butan-1-ol

Conditions
Conditions Yield
With hydrogen; at 190 ℃; under 46504.7 Torr; Gas phase;
79.1%
10.4%
5.3%
dimethyl cis-but-2-ene-1,4-dioate
624-48-6

dimethyl cis-but-2-ene-1,4-dioate

2-methoxytetrahydrofuran
13436-45-8

2-methoxytetrahydrofuran

4-butanolide
96-48-0

4-butanolide

propan-1-ol
71-23-8

propan-1-ol

2-(4'-hydroxybutoxy)-tetrahydrofuran
64001-06-5

2-(4'-hydroxybutoxy)-tetrahydrofuran

Butane-1,4-diol
110-63-4

Butane-1,4-diol

butan-1-ol
71-36-3

butan-1-ol

Conditions
Conditions Yield
With hydrogen; copper catalyst, T 4489, Sud-Chemie AG, Munich; at 150 - 280 ℃; under 187519 Torr; Neat liquid(s) and gas(es)/vapour(s);
98%
1%
0.4%
0.5%
4-butanolide
96-48-0

4-butanolide

Butane-1,4-diol
110-63-4

Butane-1,4-diol

4-hydroxybutanoic acid
591-81-1

4-hydroxybutanoic acid

succinic acid
110-15-6

succinic acid

terephthalic acid
100-21-0

terephthalic acid

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

acetic acid

propionic acid
802294-64-0,79-09-4

propionic acid

(2E)-but-2-enedioic acid
110-17-8,26099-09-2

(2E)-but-2-enedioic acid

Conditions
Conditions Yield
With hydrogen; 0.5percent Pd/0.2percent Re on Rutile TiO2; at 110 ℃; for 170 - 1009h; Product distribution / selectivity;
0.04%
0.28%
4.34%
0%
1.24%
0%
0%
85.51%
0%
0.86%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

ethylenediamine
107-15-3,85404-18-8

ethylenediamine

4-butanolide
96-48-0

4-butanolide

bis-N-(succinimido)-1,2-ethane
13323-93-8

bis-N-(succinimido)-1,2-ethane

hydrogen
1333-74-0

hydrogen

Conditions
Conditions Yield
With [Ru(PPhNNHtBu)H(CO)Cl]; potassium tert-butylate; In 1,4-dioxane; at 120 ℃; for 24h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;
60%
12 %Spectr.
Butane-1,4-diol
110-63-4

Butane-1,4-diol

4-butanolide
96-48-0

4-butanolide

homoalylic alcohol
627-27-0

homoalylic alcohol

(E/Z)-2-buten-1-ol
6117-91-5,542-72-3

(E/Z)-2-buten-1-ol

butan-1-ol
71-36-3

butan-1-ol

Conditions
Conditions Yield
With zirconium(IV) oxide; at 299.84 - 499.84 ℃; for 2h; under 760.051 Torr; Reagent/catalyst; Activation energy; Inert atmosphere;
methyl 4-(benzyloxy)butanoate
31600-42-7

methyl 4-(benzyloxy)butanoate

4-butanolide
96-48-0

4-butanolide

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
With trityl tetrafluoroborate; In acetonitrile; Product distribution; Mechanism; Ambient temperature; D2O;
28%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

4-butanolide
96-48-0

4-butanolide

4-chlorobutyraldehyde
6139-84-0

4-chlorobutyraldehyde

Conditions
Conditions Yield
With tetrachloromethane; bis(acetylacetonate)oxovanadium; at 100 ℃; for 1h;
82%
10%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

4-butanolide
96-48-0

4-butanolide

4-hydroxybutanoic acid
591-81-1

4-hydroxybutanoic acid

succinic acid
110-15-6

succinic acid

Conditions
Conditions Yield
With oxygen; In water; at 100 ℃; for 24h; under 2250.23 Torr; Reagent/catalyst;
With oxygen; In water; at 100 ℃; for 24h; under 2250.23 Torr;
76 %Spectr.
18 %Spectr.
6 %Spectr.
With oxygen; In water; at 100 ℃; for 24h; under 2250.23 Torr;
63 %Spectr.
21 %Spectr.
16 %Spectr.
With oxygen; In water; at 100 ℃; for 24h; under 2250.23 Torr;
66 %Spectr.
23 %Spectr.
11 %Spectr.
cyclobutanone
1191-95-3

cyclobutanone

4-butanolide
96-48-0

4-butanolide

4-hydroxybutanoic acid
591-81-1

4-hydroxybutanoic acid

Conditions
Conditions Yield
With dihydrogen peroxide; In acetonitrile; at 55 - 60 ℃; for 4h;
69.2%
12.3%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

4-butanolide
96-48-0

4-butanolide

4-hydroxybutanoic acid
591-81-1

4-hydroxybutanoic acid

Conditions
Conditions Yield
With 1% Pd on activated carbon; oxygen; In water; at 100 ℃; for 24h; under 2250.23 Torr;
With oxygen; In water; at 100 ℃; for 24h; under 2250.23 Torr;
71 %Spectr.
29 %Spectr.

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