| 80% |
With hydrogen In lithium hydroxide monohydrate at 80℃; |
|
| 1: 15%
2: 62% |
With [ReOCl2(1,2-bis(diphenylphosphino)ethane)]; hydrogen; potassium tetraphenylborate In toluene at 150℃; for 24h; Autoclave; Inert atmosphere; |
8
General procedure: By the following method, it went 3-reduction of phenylpropionic acid (hydrogenation).Put a stir bar in a dry glass tube (25mL), further, 3-phenylpropionic acid (75.09mg, 0.5mmol), the rhenium complex 4 (7.07mg, 0.010mmol), potassium tetraphenylborate (17.92mg , accommodates 0.05 mmol), the tubes containing this mixture, was inserted into the autoclave. Then, after replacing the inside of the autoclave in an argon gas atmosphere was added while continuing flow of argon gas dehydration toluene (4.0mL). This autoclave through a stainless steel tube by introducing hydrogen gas from a hydrogen gas cylinder connected, the inside of the autoclave was replaced with hydrogen gas, then disconnect the hydrogen gas pressure from the leak valve. This operation - was repeated (substituted de substitution) five times. Finally, the hydrogen gas pressure in the autoclave was set to 4 MPa, using a constant temperature bath, and allowed to react for 12 hours at 180 ° C. After completion of the reaction, the autoclave was cooled by immersion in an ice bath, almost to room temperature. Then, carefully release the hydrogen gas that is inside in the draft. After removing the solvent, the reaction product was analyzed by 1H NMR using mesitylene (60.1 mg, 0.5 mmol) as an internal standard substance. As a result, 3-phenylpropyl alcohol, and 3-phenylpropionic acid 3-phenylpropyl The yield was 98% and 1%, respectively. In the above Examples 6-1,Substrate (carboxylic acid compounds), and hydrogenation conditions (hydrogen pressure),Except that to adopt the conditions described in Table 7-9,It has been reduced (hydrogenated) in the same manner as in Example 6-1.However,The entry 19-26 in Table 9,Using tetrahydrofuran (THF) as a solvent.The results are shown in Tables 7 to 9. |
| 1: 19.6%
2: 9.2% |
With gold-titanium dioxide; hydrogen at 200℃; for 2h; Microwave irradiation; |
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With ruthenium; hydrogen In lithium hydroxide monohydrate at 150℃; for 24h; Glovebox; Autoclave; |
Hydrogenation of LA with molecular hydrogen using Ru-NPs
General procedure: Catalytic tests were carried out in 100 mL stainless steel Parr autoclaves. In a typical experiment, the reactor was loaded with 1 g of LA (8.6 mmol), 3 mg of nanoparticles precursor (Ru3CO12, 0.005 mmol) and 15 mL of distilled water, pressurized with 5 bar H2 at room temperature, and heated at 130 °C for 12 h. The reaction mixture was extracted with 5 × 20 mL of ethyl acetate and the solvent was removed with vacuum. Experiments with 3 Å-MS and THF were carried out in a similar way. Batches of GVL were centrifuged after workup without observing deposition of metal nanoparticles |
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With ruthenium on carbon; hydrogen In lithium hydroxide monohydrate at 100℃; |
1 Example 1
Example 1 50% wt Levulinic Acid Levulinic acid as a 50 wt % solution in water was fed to a packed-bed reactor containing a 5 wt % Ru/C catalyst at 100° C. 400 psig (H2) and WHSV=0.5. |
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With formic acid; (87)Cu984(434)Ni172(40)O2516Si58.8 In 1,4-dioxane at 265℃; Inert atmosphere; |
2.4. Levulinic acid hydrogenation
The hydrogenation of LA with FA was performed in a conven-tional stainless-steel fixed-bed reactor (internal diameter 1 cm andlength 300 mm), in which 1 g of catalyst was packed. Vaporizedmixtures of LA and FA dissolved in 1,4-dioxane (10 wt% = 7.2 g ofLA and 2.85 g of FA in 90 g of 1,4-dioxane) were introduced intothe reactor via a syringe pump with 20 ml/min of nitrogen flowthrough a preheated line. In order to study the effect of FA concen-tration, we keep constant weight of LA (7.2 g) and concentration ofFA was varied accordingly. The liquid products were analyzed usinga gas chromatograph (DONAM DS6200) equipped with a flame ion-ization detector and capillary column (CycloSil-B). Only the molarconversion of LA was considered for this study because FA was usedas a hydrogen source. The decomposition of FA to form H2andCO2was confirmed using GC equipped with a TCD detector witha Carbosphere column. |
| 1: 73 %Chromat.
2: 5 %Chromat. |
With ammonium hexafluorophosphate; tris(acetylacetonato)ruthenium (III); hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 150℃; for 25h; High pressure; |
|
| 1: 9 %Chromat.
2: 83 %Chromat. |
With tris(acetylacetonato)ruthenium (III); hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 150℃; for 25h; High pressure; |
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With C40H38NP3; ruthenium(III) acetylacetonate In tetrahydrofuran at 160℃; for 18h; |
|
| 1: 78 %Chromat.
2: 17 %Chromat. |
With hydrogen In ethanol at 199.84℃; |
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With ruthenium(III) trichloride trihydrate; hydrogen In acetonitrile at 140℃; for 6h; |
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With hydrogen In ethanol at 140℃; for 6h; Overall yield = 92 %; |
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With hydrogen In lithium hydroxide monohydrate at 70℃; Flow reactor; Green chemistry; |
|
| 1: 73.7 %Chromat.
2: 15.3 %Chromat. |
With hydrogen In ethanol at 140℃; for 2h; Autoclave; |
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Multi-step reaction with 2 steps
1: hydrogen / 2 h / 170 °C / 22502.3 Torr / Autoclave
2: hydrogen / ethanol / 3 h / 140 °C / 37503.8 Torr / Autoclave |
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With (5,10,15,20-tetraphenylporphinato)chloroiridium(III); hydrogen In N,N-dimethyl-formamide at 100℃; for 12h; Autoclave; Schlenk technique; |
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With rhodium-meso-tetrakis(4-carboxyphenyl)porphyrin; hydrogen In butan-1-ol at 100℃; for 12h; Schlenk technique; Autoclave; |
|
| 1: 90 %Spectr.
2: 6 %Spectr. |
With Ru(CO3)(CO){CH3C(CH2PPh2)3-κ3P}; hydrogen In 1,4-dioxane at 130℃; for 25h; Autoclave; |
5.11. Hydrogenation experiments
A solution of levulinic acid (1.16 g, 10 mmol) and catalyst (0.5 mol %, 0.05 mmol) in 25 mL of solvent (1,4-dioxane or methanol) was injected into a pre-purged high-pressure autoclave reactor un- der a positive flow of nitrogen. The reactor was sealed, and the at- mosphere was changed from nitrogen to hydrogen following three cycles of pressurizing and depressurizing the system with hydro- gen at 5 bar pressure. The pressure was then increased to required pressure (typically between 15 and 50 bar) with stirring at 40 0 0 rpm and heated to the required temperature. Reactions were run for 10-24 h, the vessel cooled to room temperature and depres- surised. The crude reaction mixture was passed through a plug of silica. The products and unreacted substrates were identified by their characteristic methyl signals using 1 H NMR spectroscopy. Methyl protons of LA are identified by the characteristic singlet at 2.10 ppm, while GVL, 2-MTHF and 1,4-PDO display doublets at 1.33 ppm, 1.19 ppm and 1.05 ppm respectively. |
| 1: 82 %Chromat.
2: 18 %Chromat. |
With hydrogen In lithium hydroxide monohydrate at 503℃; for 3h; |
|
| 1: 81 %Chromat.
2: 19 %Chromat. |
With hydrogen In lithium hydroxide monohydrate; isopropanol; Bicyclo[4.4.0]decane at 110℃; for 3h; Autoclave; |
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