DL-Lactic acid (2-Hydroxypropanoic acid) to Propionic acid by Asch

Bioactivities (10143)

Yield

Reactions (34)

Substances (34)

Conditions

Targets (576)

Citations (43)

References A

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A: 5.5% B: 5.9%

With cobalt in water

T=250°C; 2 h; Green chemistry; ConcentrationTemperatureReagent/catalyst;

Huo, Zhibao; Xiao, Jiefeng; Ren, Dezhang; Jin, Fangming; Wang, Tian; Yao, Guodong

Green Chemistry, 2017 , vol. 19, # 5 p. 1308 - 1314 Title/Abstract Full Text View citing articles Show Details

Geschwindigkeit des aeroben und anaeroben Abbaus durch P.pentosaceum und P.zeae;

Fromageot; Bost

Enzymol., 1938 , vol. 2, p. 232 Chem. Zentralbl., 1938 , vol. 109, # II p. 1064 Full Text Show Details

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With cobalt; zinc in water

T=250°C; 2 h; Inert atmosphere; TemperatureReagent/catalyst; Hide Experimental Procedure

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Rx-ID: 101722

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Shanghai Jiaotong University; Huo, Zhibao; Xiao, Jiefeng; Ren, Dezhang; Jin, Fangming; Jiang, Naimeng; Yao, Guodong

Patent: CN106117035 A, 2016 ; Location in patent: Paragraph 0038; 0039; 0040; 0041; 0042; 0043 ; Title/Abstract Full Text Show Details

1:Example 1

lactic acid(1.5 mmol, reaction concentration 200 mmol / L), Zn powder (10 mmol) and Co powder (4 mmol)Teflon-lined reactor, the reactor was filled with water to a 25percent rate, and the reactor was purged with nitrogen to remove airThe reactor was placed in an oven to make the reaction temperature 250 ° C, the reaction time 120 min, and the reaction was taken outThe mixture was filtered to give a propionic acid solution.The reaction product, propionic acid, was analyzed by HPLC (see Fig. 1), and the results shown in Fig. 1 showed that propionic acid was the mainThe yield was 58.79percent. 6%

With titanium(IV) oxide; zinc in water

T=250°C; 2 h; Green chemistry; Reagent/catalyst;

Huo, Zhibao; Xiao, Jiefeng; Ren, Dezhang; Jin, Fangming; Wang, Tian; Yao, Guodong

Green Chemistry, 2017 , vol. 19, # 5 p. 1308 - 1314 Title/Abstract Full Text View citing articles Show Details

Einw. von Propionilbacterium pentosaceum;

Delwiche

J.Bacteriol.Chem.Abstr., 1948 , vol. 56, p. 815 J.Bacteriol.Chem.Abstr., 1949 , p. 2277 Full Text Show Details Fromageot; Bost Enzymol., 1937 , vol. 2, p. 225 Full Text Show Details

Einw. von Propionsaeurebakterien;

Erb,Wood,Werkman

J.Bacteriol., vol. 31, p. 599 Chem. Zentralbl., 1936 , vol. 107, # II p. 1188 Full Text Show Details

bei der Einw. von Bact.acidi propionici, Bact.acidi propionici a oder Bact.acidi propionici b;

v.Freudenreich; Jensen Zbl.Bakt.Parasitenk., 1907 , vol. <II>17, p. 537,539 Full Text Show Details

bei der Einw. Bact.propionicum;

Maurer

Biochemische Zeitschrift, 1927 , vol. 191, p. 83 Full Text View citing articles Show Details

Virtanen

Comment.phys.-math.Helsingfors, vol. 1, # 36 p. 11 Chem. Zentralbl., 1924 , vol. 95, # II p. 64 Full Text Show Details

With hydrogen iodide

Lautemann

Justus Liebigs Annalen der Chemie, 1860 , vol. 113, p. 217 Full Text View citing articles Show Details

With hydrogen iodide

Freund

Journal fuer Praktische Chemie (Leipzig), 1872 , vol. <2>5, p. 446 Full Text View citing articles Show Details

als Zwischenprodukt bei der Vergaerung zu Methan durch

Tarvin; Buswell

Abwasserbakterien;

Journal of the American Chemical Society, 1934 , vol. 56, p. 1753 Full Text View citing articles Show Details

With hydrogen

T=199.84°C; Gas phase;

Simonov; Simakova; Minyukova; Khassin

Russian Chemical Bulletin, 2009 , vol. 58, # 6 p. 1114 - 1118 Title/Abstract Full Text View citing articles Show Details

in water

T=300°C; 3 h; Catalytic behavior; Reagent/catalystTemperature; Hide Experimental Procedure

Patent: CN106431890 A, 2017 ; Location in patent: Paragraph 0027; 0028; 0029; 0030; 0031; 0032; 0033-0091 ; Title/Abstract Full Text Show Details

4:Example 4

The activated alumina powder was placed in a muffle furnace and calcined at 500 ° C for 3 hours under static or flowing air,The rate of heating was 5 ° C / min to obtain the calcined alumina powder. Weigh 0.2 g of tin sulfate in a beaker, add 30 ml of deionized water, and weigh 1.0 g of calcined alumina powderWas added to the solution, treated with ultrasonic dipping, treated at room temperature for three hours, and then the resulting solution was placed in a microwaveAnd the resulting catalyst was dried in a drying oven at 130 ° C for 4 hours, followed by filtrationThe temperature is calcined at a temperature programmed temperature rise of 5-10 ° C / min, and the calcination temperature is set at 600 ° C and calcined at constant temperature for 3 hours to obtain20 wtpercent SnSO4 / Al2O3 supported catalyst, wherein SnSO4 corresponds to a supported amount of carrier Al2O3 of 20 wtpercent. The obtained 20 wtpercent SnSO4 / Al2O3 supported catalyst was 0.8-1.2 g, compressed, ground,Take 40-60 mesh particles as a catalyst. The prepared catalyst was placed at a diameter of 8 mm,A length of 45 cm in the middle of the tubular reactor,The upper and lower portions of the catalyst are filled with 40-60 mesh quartz sand.The tube reactor filled with the catalyst is then placed in a heating furnace,Open the carrier gas (N2) and access, access flow rate of 20ml / min,Open the heating device,The temperature was raised to 300 ° C by the temperature of the program (3-5 ° C / min)A constant temperature was passed through 10 wtpercent aqueous solution of lactic acid at a flow rate of 0.5 ml / min,After 3 hours of reaction, the product was collected and subjected to product analysis,To gas chromatography as a detection tool,Using n-butanol as internal standard, using FFAP capillary column,Hydrogen flame (FID) detection,The results showed that the conversion of lactic acid was 100percentThe selectivity of propionic acid was 82.6percent. A

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With calcium phosphate-calcium pyrophosphate composite catalyst in water

T=390°C; 27 h; Inert atmosphere;

Hong, Ju Hyeong; Lee, Jong-Min; Kim, Hyungrok; Hwang, Young Kyu; Chang, Jong-San; Halligudi, Shiva B.; Han, Yo-Han

Applied Catalysis A: General, 2011 , vol. 396, # 1-2 p. 194 - 200 Title/Abstract Full Text View citing articles Show Details

With (7.1percentNa2HPO4)/Na3/K-L-type zeolite in water

T=350°C; 5 h; TemperatureConcentrationReagent/catalyst; Hide Experimental Procedure

MYRIANT CORPORATION; OZMERAL, A., Cenan; GLAS, Joseph P.; DASARI, Rajesh; TANIELYAN, Setrak; BHAGAT, Ramesh Deoram; KASIREDDY, Mohan Reddy; SINGH, Ramnik; GNANADESIKAN, Vijay; AUGUSTINE, Robert L.; MORE, Santosh

Patent: WO2013/134385 A1, 2013 ; Location in patent: Paragraph 0146; 0147 ; Title/Abstract Full Text Show Details

[0146] Dehydroxylation of Lactic Acid in a Water Solvent - Lactic Acid Concentration Effect. Starting compositions with 50percent and 60percent initial concentrations of lactic acid ("LA") in water as listed in Table 9 were reacted in the vapor phase with a (7.1percent Na2HPO4)/Na3/K-L-type zeolite, according to Reaction Protocol III above, for 5 hours at varying temperatures as listed in Table 9. [0147] As shown in Table 9, increasing the temperature led to an increase in the conversion but

the selectivity was minimally changed at the higher temperature. Further, increasing the initial lactic acid concentration has minimal effect, at least at these concentrations, on the conversion and selectivity at the corresponding temperatures A: 7.9 %Chromat. B: 7.4 %Chromat. C: 18.5 %Chromat.

With barium phosphate in water

T=400°C; Flow reactor; Hide Experimental Procedure

Tang, Congming; Peng, Jiansheng; Fan, Guoce; Li, Xinli; Pu, Xiaoli; Bai, Wei

Catalysis Communications, 2014 , vol. 43, p. 231 - 234 Title/Abstract Full Text View citing articles Show Details

Catalyst evaluation

General procedure: The dehydration of lactic acid to acrylic acid over the catalysts was carried out in a fixed-bed quartz reactor with a 4mm inner diameter operated at atmospheric pressure. The catalyst (0.50–0.60 g, 20–40 meshes) was placed in the middle of the reactor and quartz wool was placed in both ends. Before catalytic evaluation the catalyst was pretreated at the required reaction temperature (400 °C) for 1.0 hunder high purity N2 (0.1 MPa, 1.0 mL/min). The feedstock (20 wt.percent solution of lactic acid) was then pumped into the preheating zone (lactic acid aqueous solution flow rate, 1.0 mL/h) and driven through the catalyst bed by nitrogen. The liquid products were condensed using ice-water bath and analyzed off-line using an SP-6890 gas chromatograph with a FFAP capillary column connected to an FID. Quantitative analysis of the products was carried out by the internal standard method using n-butanol as the internal standard material. GC–MS analyses of the samples were performed using Agilent 5973N Mass Selective Detector attachment.

A: 79

With aluminum oxide in water

Peng, Jiansheng; Li, Xinli; Tang, Congming; Bai, Wei

%Chromat. B: 5.5 %Chromat. C: 9.4 %Chromat.

T=400°C; P=760.051 Torr; Flow reactorInert atmosphereGas phase; Reagent/catalyst;

Green Chemistry, 2014 , vol. 16, # 1 p. 108 - 111 Title/Abstract Full Text View citing articles Show Details

A: 23 %Chromat. B: 24.1 %Chromat. C: 27 %Chromat.

With sodium sulfate in water

T=400°C; P=760.051 Torr; Flow reactorInert atmosphereGas phase;

Peng, Jiansheng; Li, Xinli; Tang, Congming; Bai, Wei

Green Chemistry, 2014 , vol. 16, # 1 p. 108 - 111 Title/Abstract Full Text View citing articles Show Details

A: 20.5 %Chromat. B: 7.6 %Chromat. C: 68.6 %Chromat.

With calcium sulfate in water

T=400°C; P=760.051 Torr; Flow reactorInert atmosphereGas phase; Time;

Peng, Jiansheng; Li, Xinli; Tang, Congming; Bai, Wei

Green Chemistry, 2014 , vol. 16, # 1 p. 108 - 111 Title/Abstract Full Text View citing articles Show Details

A: 20.3 %Chromat. B: 9.4 %Chromat. C: 65.7 %Chromat.

With barium sulfate in water

T=400°C; P=760.051 Torr; Flow reactorInert atmosphereGas phase; Reagent/catalystTemperatureConcentrationTime;

Peng, Jiansheng; Li, Xinli; Tang, Congming; Bai, Wei

Green Chemistry, 2014 , vol. 16, # 1 p. 108 - 111 Title/Abstract Full Text View citing articles Show Details

With HAP-300 in water

T=349.84°C; 6 h; Inert atmosphere; Hide Experimental Procedure

Matsuura, Yumiko; Onda, Ayumu; Yanagisawa, Kazumichi

Catalysis Communications, 2014 , vol. 48, p. 5 - 10 Title/Abstract Full Text View citing articles Show Details

General procedure: The typical catalytic conversions of lactic acid to acrylic acid werecarried in a fixed-bed continuous-flow reactor under atmosphericpressure. Before reaction, the pelletized catalysts (0.2–1.0 g) werepretreated at 773 K for 3 h in Ar flow and cooled to 623 K. 38 wt.percent lacticacid aqueous solution (1.2 mL h−1) was introduced into the reactor by amicrosyringe pump with 40 mL min−1 of Ar gas. The products werecondensed in an ice–water trap. The collected liquid products were analyzedon a GC-FID (Shimadzu GC14B) with a Stabilwax-DA column.And, after the dilutions of the collected liquid products with distilledwater into 50 mL, they were analyzed using an HPLC (HITACHI LC-2000withUVdetector)with a Shodex KC811 column, and a total organiccarbon analyzer (TOC2000, Shimadzu). The gas product of acetaldehydewas determined by on-line GC-TCD (Shimadzu GC8A) with aGaskuropack 54. CO and CO2 were non-quantitatively analyzed by onlineGC-TCD. The lactic acid conversion and product yieldwere calculatedbased on the following equations: With lanthanum phosphate nanorods in water

T=350°C; Inert atmosphere;

Guo, Zhen; Theng, De Sheng; Tang, Karen Yuanting; Zhang, Lili; Huang, Lin; Borgna, Armando; Wang, Chuan

Physical Chemistry Chemical Physics, 2016 , vol. 18, # 34 p. 23746 - 23754 Title/Abstract Full Text View citing articles Show Details

With water; copper

T=300°C; P=300030 Torr; 0.0101111 h; AutoclaveGreen chemistry; Hide Experimental Procedure

NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY; KAWANAMI, HAJIME; HATAKEDA, KIYOTAKA; ISHIZAKA, TAKAYUKI; NAGAO, IKUHIRO

Patent: JP2017/14144 A, 2017 ; Location in patent: Paragraph 0011; 0021-0024 ; Title/Abstract Full Text Show Details

1:Example 1 [Synthesis 1 of acrylic acid from lactic acid]

The reaction was carried out using a high temperature high pressure microreaction system. Figure 2 shows the reaction part of the high-temperature high-pressure microreaction system.The reaction was carried out using a 10 m long double tube (FIG. 3) obtained by lining a copper tube having an inner diameter of 0.5 mm inside the pipe made of SUS 316 having an outer shape of 1/8 inch. Using lactic acid as a raw material as 2-hydroxycarboxylic acid,The reaction was carried out using acrylic acid as an α, β-unsaturated carboxylic acid as an objective substance.Lactic acid aqueous solution (0.11 M, 0.5 mL / min)High temperature and high pressure water (distilled water or ion exchanged water,2.0 mL / min) with a micro mixer,From room temperature (25 ° C.) to a predetermined temperature (300, 320, 340, 360, 380, 400 ° C., 420,A pressure of 40 MPa).The temperature after the temperature rise is,The temperature of the oven was adjusted so that the temperature difference between the entrance and the exit was less than 0.1 ° C as observed with a thermocouple.After mixing and raising the temperature and reacting in a reaction tube under high temperature and high pressure conditions, After cooling to a predetermined temperature (40 ° C.) with a cooler (heat exchanger)Finally, pressure was released via a back pressure valve.Reaction time isConverting from the density of water,46.8 seconds at 300 ° C., 44.7 seconds at 320 ° C., 39.7 seconds at 360 ° C., 36.4 seconds at 380 ° C., 32.0 seconds at 400 ° C. and 25.9 seconds at 420 ° C. .In the obtained sample,With clear aqueous solution,Analysis,Without special treatment,The aqueous solution was analyzed by liquid chromatography and gas chromatography (GC), and the product was analyzed. FIG. 4 shows a GC chart of the obtained sample (reaction temperature 380 ° C., reaction pressure 40 MPa, reaction time 36.4 seconds).HP-INNOWAX was used for the column, and the product was detected using the FID detector for the detector.Compound identification of each peak was made from GC-MS and standard sample, and the yield of each compound was obtained by preparing a calibration curve using a standard sample. FIG. 5 shows,When conducted at each temperature, acrylic acid,Hydroxyacetone,Acetic acid,Propionic acid,Acetaldehyde,The yields of 3-methyl-2 (5H) -furanone were determined and shown in the graph.At 40 MPa,It was found that the maximum value exists between 360 ° C. and 380 ° C.,It was found that the yield of acrylic acid was highest at 85percent. At the same time, it was also found that the yield of acetaldehyde decreased to 10percent.Incidentally, including the following Examples 2 to 5,In either case, the raw lactic acid was not left and the conversion was 100percent.Therefore, in Examples 1 to 5, the selectivity and yield values were the same. FIG. 5 shows,When conducted at each temperature, acrylic acid,Hydroxyacetone,Acetic acid,Propionic acid,Acetaldehyde,The yields of 3-methyl-2 (5H) -furanone were determined and shown in the graph.At 40 MPa,It was found that the maximum value exists between 360 ° C. and 380 ° C.,It was found that the yield of acrylic acid was highest at 85percent. At the same time, it was also found that the yield of acetaldehyde decreased to 10percent.Incidentally, including the following Examples 2 to 5,In either case, the raw lactic acid was not left and the conversion was 100percent.for that reason,In Examples 1 to 5, the selectivity and yield values were the same. With barium sulfate; ammonia in water

T=420°C; 24 h; Temperature;

Li, Xinli; Chen, Zhi; Cao, Ping; Pu, Wenjie; Zou, Weixin; Tang, Congming; Dong, Lin

RSC Advances, 2017 , vol. 7, # 86 p. 54696 - 54705 Title/Abstract Full Text View citing articles Show Details

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A: 5.2% B: 5.1% C: 1% D: 74.3%

With 12percent Na2HPO4-modified NaY-20.1 (H2O/SiO2 molar ratio) in water

T=340°C; 2 h; Catalytic behavior; Reagent/catalystTemperature;

Zhang, Junfeng; Zhao, Yuling; Feng, Xinzhen; Pan, Min; Zhao, Jing; Ji, Weijie; Au, Chak-Tong

Catalysis Science and Technology, 2014 , vol. 4, # 5 p. 1376 - 1385 Title/Abstract Full Text View citing articles Show Details

A: 2.5% B: 13.6% C: 1.1% D: 42%

With NaY-20.1 (H2O/SiO2 molar ratio) in water

T=340°C; 2 h; Catalytic behavior; Reagent/catalystTemperature;

Zhang, Junfeng; Zhao, Yuling; Feng, Xinzhen; Pan, Min; Zhao, Jing; Ji, Weijie; Au, Chak-Tong

Catalysis Science and Technology, 2014 , vol. 4, # 5 p. 1376 - 1385 Title/Abstract Full Text View citing articles Show Details

With calcium phosphate hydroxyapatite; ammonia; sodium hydroxide in water

T=349.84°C; 6 h; Inert atmosphere; Hide Experimental Procedure

Matsuura, Yumiko; Onda, Ayumu; Yanagisawa, Kazumichi

Catalysis Communications, 2014 , vol. 48, p. 5 - 10 Title/Abstract Full Text View citing articles Show Details

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With dipotassium hydrogenphosphate

3 h; Reagent/catalyst; Hide Experimental Procedure

MYRIANT CORPORATION; OZMERAL, Cenan; DASARI, Rajesh; SINGH, Ramnik; NODA, Yu; RIOUX, Robert, M.; ROMAN-LESHKOV, Yuriy

Patent: WO2016/201181 A1, 2016 ; Location in patent: Page/Page column 41; 53 ; Title/Abstract Full Text Show Details

13:Catalytic dehydration of lactic acid using modified NaZSM-5 zeolite

In the first set of experiments, NaZSM-5 zeolite was modified by impregnating one of the five different potassium phosphate compounds as provided in Table 7 and each of the modified NaZSM-5 zeolites was tested for their efficiency in vapor phase dehydration reaction. The vapor phase dehydration reaction using lactic acid as a reactant was carried out using the following experimental parameters: Gas flow rate: 55cc/mm; Feed: Heat treated 20percent USP lactic acid; Feed flow rate: 0.1 cc/mi; Temp: 330°C; Catalyst volume: 3 cc. As the results shown in Table 7 indicate among the five different potassium phosphate compound tested, monobasic potassium phosphate (KH2PO4) at 2mmol/g of zeolite was found to be efficient doping agent in terms of resulting in the formation of acetaldehyde as the only major side product in the vapor phase dehydration reaction using lactic acid for the production acrylic acid. Stage #1: With Cs-doped hydroxyapatite in water

T=300°C; P=760.051 Torr; Inert atmosphere; Stage #2: T=700°C; Calcination; Reagent/catalyst;

Li, Xinli; Sun, Liangwei; Zou, Weixin; Cao, Ping; Chen, Zhi; Tang, Congming; Dong, Lin

ChemCatChem, 2017 , vol. 9, # 24 p. 4621 - 4627 Title/Abstract Full Text View citing articles Show Details

With 96 wtpercent sodium ion-4 wtpercent potassium ionexchanged 46 molar SiO2/Al2O3 ratio ZSM-11 zeolite in water

T=360°C; P=760.051 Torr; Flow reactorInert atmosphere; Reagent/catalyst;

Yan, Bo; Tao, Li-Zhi; Mahmood, Azhar; Liang, Yu; Xu, Bo-Qing

ACS Catalysis, 2017 , vol. 7, # 1 p. 538 - 550 Title/Abstract Full Text View citing articles Show Details

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A: 72.3%

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Stage #1: With Cs-doped hydroxyapatite in water

T=300°C; P=760.051 Torr; Inert atmosphere; Stage #2: T=400°C; Calcination; Reagent/catalyst;

Li, Xinli; Sun, Liangwei; Zou, Weixin; Cao, Ping; Chen, Zhi; Tang, Congming; Dong, Lin

ChemCatChem, 2017 , vol. 9, # 24 p. 4621 - 4627 Title/Abstract Full Text View citing articles Show Details

With Mg0388Al2408O4

T=380°C; P=760.051 Torr; pH=7 - 8; Gas phase; Reagent/catalystConcentration; Hide Experimental Procedure

Tang, Congming; Zhai, Zhanjie; Li, Xinli; Sun, Liangwei; Bai, Wei

Journal of Catalysis, 2015 , vol. 329, art. no. 11766, p. 206 - 217 Title/Abstract Full Text View citing articles Show Details

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2.4. Catalyst evaluation

The synthesis of acetaldehyde from LA over the catalysts is carried out in a fixed-bed quartz reactor with an 4 mm inner diameter operated at atmospheric pressure. The catalyst (ca. 0.3 g, 20–40 meshes) is placed in the middle of the reactor and quartz wool is placed in both ends. Firstly, the catalyst is pretreated at the required reaction temperature (ca. 380 C) for 1.0 h under N2 withhigh purity (0.1 MPa, 1.0 mL/min). The feedstock (20 wtpercent solutionof LA) is then pumped into the reactor (LA aqueous solution flowrate, 1.0 mL/h) and driven through the catalyst bed by nitrogen. The contact time of reactant over the catalyst is around 0.5 s, and the contact time is estimated according to Eq. (1) [32,49]. The liquid products are condensed using ice-water bath and analyzed off-line using a SP-6890 gas chromatograph with a FFAP capillary column connected to a FID. Quantitative analysis of the products is carried out by the internal standard method using n-butanol as the internal standard material. GC–MS analyses of the samples are performed using Agilent 5973N Mass Selective Detector attachment. The reaction tail gas is analyzed using GC with a packed column of TDX-01 connected to TCD detector. The conversion of LA and the selectivity toward acetaldehyde or other by-products are calculated according to Eqs. (2) and (3). A

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A: 15.6% B: 7.3% C: 6.4%

With cobalt; zinc in water

T=300°C; 1 h; Green chemistry;

Huo, Zhibao; Xiao, Jiefeng; Ren, Dezhang; Jin, Fangming; Wang, Tian; Yao, Guodong

Green Chemistry, 2017 , vol. 19, # 5 p. 1308 - 1314 Title/Abstract Full Text View citing articles Show Details

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A: 17.8% B: 47.3% C: 30.9%

With cobalt; zinc in water

T=250°C; 2 h; Green chemistry; ConcentrationTemperatureReagent/catalyst;

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Huo, Zhibao; Xiao, Jiefeng; Ren, Dezhang; Jin, Fangming; Wang, Tian; Yao, Guodong

Green Chemistry, 2017 , vol. 19, # 5 p. 1308 - 1314 Title/Abstract Full Text View citing articles Show Details

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With water; copper

T=400°C; P=300030 Torr; AutoclaveGreen chemistry; Hide Experimental Procedure

NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY; KAWANAMI, HAJIME; HATAKEDA, KIYOTAKA; ISHIZAKA, TAKAYUKI; NAGAO, IKUHIRO

Patent: JP2017/14144 A, 2017 ; Location in patent: Paragraph 0021-0023; 0029 ; Title/Abstract Full Text Show Details

1:compartive Example 1 [Synthesis of Acrylic Acid from Lactic Acid 4 - Influence Survey of the Type of Alloy 1]

The reaction was carried out using a high temperature high pressure microreaction system. Figure 2 shows the reaction part of the high-temperature high-pressure microreaction system.The reaction was carried out using a 10 m long double tube (FIG. 3) obtained by lining a copper tube having an inner diameter of 0.5 mm inside the pipe made of SUS 316 having an outer shape of 1/8 inch. Using lactic acid as a raw material as 2-hydroxycarboxylic acid,The reaction was carried out using acrylic acid as an α, β-unsaturated carboxylic acid as an objective substance.Lactic acid aqueous solution (0.11 M, 0.5 mL / min)High temperature and high pressure water (distilled water or ion exchanged water,2.0 mL / min) with a micro mixer,From room temperature (25 ° C.) to a predetermined temperature (300, 320, 340, 360, 380, 400 ° C., 420,A pressure of 40 MPa).The temperature after the temperature rise is,The temperature of the oven was adjusted so that the temperature difference between the entrance and the exit was less than 0.1 ° C as observed with a thermocouple.After mixing and raising the temperature and reacting in a reaction tube under high temperature and high pressure conditions, After cooling to a predetermined temperature (40 ° C.) with a cooler (heat exchanger)Finally, pressure was released via a back pressure valve.Reaction time isConverting from the density of water,46.8 seconds at 300 ° C., 44.7 seconds at 320 ° C., 39.7 seconds at 360 ° C., 36.4 seconds at 380 ° C., 32.0 seconds at 400 ° C. and 25.9 seconds at 420 ° C. .In the obtained sample,With clear aqueous solution,Analysis,Without special treatment,The aqueous solution was analyzed by liquid chromatography and gas chromatography (GC), and the product was analyzed. FIG. 4 shows a GC chart of the obtained sample (reaction temperature 380 ° C., reaction pressure 40 MPa, reaction time 36.4 seconds).HP-INNOWAX was used for the column, and the product was detected using the FID detector for the detector.Compound identification of each peak was made from GC-MS and standard sample, and the yield of each compound was obtained by preparing a calibration curve using a standard sample. FIG. 5 shows,When conducted at each temperature, acrylic acid,Hydroxyacetone,Acetic acid,Propionic acid,Acetaldehyde,The yields of 3-methyl-2 (5H) -furanone were determined and shown in the graph.At 40 MPa,It was found that the maximum value exists between 360 ° C. and 380 ° C.,It was found that the yield of acrylic acid was highest at 85percent. At the same time, it was also found that the yield of acetaldehyde decreased to 10percent.Incidentally, including the following Examples 2 to 5,In either case, the raw lactic acid was not left and the conversion was 100percent.Therefore, in Examples 1 to 5, the selectivity and yield values were the same. As the material of the reaction tube, SUS 316,Hastelloy (registered trademark) C-276,Alternatively, acrylic acid was synthesized under the same conditions as in Example 1 except that an alloy system of Inconel 625 was used.result,In any of the alloys, the yield of acrylic acid remained at only about 14percent at the maximum, and it turned out that there was not much effect.Also, in the case of using SUS 316, the breakdown of products at 400 ° C. and 40 MPa is as follows:49percent acetaldehyde,1.5percent of hydroxyacetone,8.2percent of acetic acid,Propionic acid is 29percent7.9percent acrylic acid,Other (furanone etc.) is 4.2percentBy-products other than acrylic acid, Especially propionic acid and acetaldehyde were found to be the main products. A

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A: 34% B: 8%

With 20 wtpercent H4PVMo11O40 on CARiACT.(R). Q-15 supported in water

T=274.84°C; 16 h; Inert atmosphere;

Katryniok, Benjamin; Paul, Sebastien; Dumeignil, Franck

Green Chemistry, 2010 , vol. 12, # 11 p. 1910 - 1913 Title/Abstract Full Text View citing articles Show Details

With iron(II) oxide

T=390°C; Inert atmosphere; Reagent/catalyst;

Li, Xinli; Zhai, Zhanjie; Tang, Congming; Sun, Liangwei; Zhang, Yu; Bai, Wei

RSC Advances, 2016 , vol. 6, # 67 p. 62252 - 62262 Title/Abstract Full Text View citing articles Show Details

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D: 44%

With Cs beta zeolite T=360°C; 10 h;

Yan, Bo; Mahmood, Azhar; Liang, Yu; Xu, Bo-Qing

Catalysis Today, 2016 , vol. 269, p. 65 - 73 Title/Abstract Full Text View citing articles Show Details

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With iron(II,III) oxide

T=390°C; Inert atmosphere; Reagent/catalyst;

Li, Xinli; Zhai, Zhanjie; Tang, Congming; Sun, Liangwei; Zhang, Yu; Bai, Wei

RSC Advances, 2016 , vol. 6, # 67 p. 62252 - 62262 Title/Abstract Full Text View citing articles Show Details

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With nonstoichiometric calcium pyrophosphate in water

T=375°C; Flow reactor; Reagent/catalystTemperature;

Ghantani, Vidhya C.; Dongare, Mohan K.; Umbarkar, Shubhangi B.

RSC Advances, 2014 , vol. 4, # 63 p. 33319 - 33326 Title/Abstract Full Text View citing articles Show Details

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With calcium pyrophosphate; nitrogen; water

T=170°C; Kinetics; Reagent/catalystTime; Hide Experimental Procedure

Blanco; Delichere; Millet; Loridant

Catalysis Today, 2014 , vol. 226, p. 185 - 191 Title/Abstract Full Text View citing articles Show Details

2.3 Catalytic testing

General procedure: Dehydration of lactic acid was conducted in a fixed bed reactor (inner diameter 14 mm) operating at atmospheric pressure. A 20 weight percent aqueous solution of lactic acid was fed using 307 HPLC pump (Gilson), vaporized at 170 °C with home-made system and diluted with N2. The vaporization temperature was determined from liquid vapor equilibrium simulated by the ProSim plus software (ProSim S.A.). The feed composition was LA/H2O/N2: 3/66/31. Before addition of the vaporized LA solution, the reactor was heated at the reaction temperature under N2. The contact time was varied from 0.1 to 4.1 s (GHSV from 36,000 to 880 h−1). Condensable molecules were collected in a cold trap at −4 °C and analyzed off-line with a GC-2014 chromatograph (Shimadzu) equipped with AOC-20i auto injector, ZB-WAXplus (30 m, 0.32 mm) column and FID detector, while gas products, mainly CO, CO2 and N2 were analyzed online with the same chromatograph but using sampling valve, Carboxen 1000 column and TCD detector.

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With calcium pyrophosphate; nitrogen; water

T=380°C; Reagent/catalystTime; Hide Experimental Procedure

Blanco; Delichere; Millet; Loridant

Catalysis Today, 2014 , vol. 226, p. 185 - 191 Title/Abstract Full Text View citing articles Show Details

2.3 Catalytic testing

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With bis(acetylacetonato)dioxidomolybdenum(VI); sodium hydroxide in Triethylene glycol dimethyl ether; water

T=220 - 270°C; Inert atmosphere; Reagent/catalystSolventPressure;

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Rx-ID: 35746880

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Korstanje, Ties J.; Kleijn, Hendrik; Jastrzebski, Johann T. B. H.; Klein Gebbink, Robertus J. M.

Green Chemistry, 2013 , vol. 15, # 4 p. 982 - 988 Title/Abstract Full Text View citing articles Show Details

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With bis(acetylacetonato)dioxidomolybdenum(VI); sodium hydroxide in water

T=200 - 270°C; Inert atmosphere; SolventTemperature;

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Rx-ID: 35746881

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Korstanje, Ties J.; Kleijn, Hendrik; Jastrzebski, Johann T. B. H.; Klein Gebbink, Robertus J. M.

Green Chemistry, 2013 , vol. 15, # 4 p. 982 - 988 Title/Abstract Full Text View citing articles Show Details

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With bis(acetylacetonato)dioxidomolybdenum(VI) in water

T=200 - 270°C; Inert atmosphere;

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Rx-ID: 35746882

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Korstanje, Ties J.; Kleijn, Hendrik; Jastrzebski, Johann T. B. H.; Klein Gebbink, Robertus J. M.

Green Chemistry, 2013 , vol. 15, # 4 p. 982 - 988 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 36232479

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With Na3/K-L-type zeolite in water

T=340°C; 4 h; Hide Experimental Procedure

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Patent: WO2013/134385 A1, 2013 ; Location in patent: Paragraph 0152; 0153 ; Title/Abstract Full Text Show Details

[0152]Dehydroxylation of Lactic Acid in a Solvent — Solvent Effect. A starting composition as listed in Table 12 was reacted in the vapor phase with a Na3/K-L-type zeolite, according to Reaction Protocol III above, for 4 hours at 340°C.[0153]As shown in Table 12, a Na3/K-L-type zeolite does catalyze esterificationreactions. Further, the addition of an alcohol in the starting composition appears to haveeffect on the conversion but does dramatically reduce the selectivity to acrylic acid. A

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With Na3/K-L-type zeolite in water

T=340°C; 4 h; Hide Experimental Procedure

Patent: WO2013/134385 A1, 2013 ; Location in patent: Paragraph 0152; 0153 ; Title/Abstract Full Text Show Details

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With hydrogen; silica gel in water

T=349.84°C; P=42754.3 Torr; Mechanism; Reagent/catalyst;

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Carlos Serrano-Ruiz, Juan; Dumesic, James A.

Green Chemistry, 2009 , vol. 11, # 8 p. 1101 - 1104 Title/Abstract Full Text View citing articles Show Details

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With hydrogen

T=199.84°C; Gas phase;

Simonov; Simakova; Minyukova; Khassin

Russian Chemical Bulletin, 2009 , vol. 58, # 6 p. 1114 - 1118 Title/Abstract Full Text View citing articles Show Details

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A: 14% B: 9.1% C: 12.5% D: 1.6% E: 3.1% F: 7.8%

With sodium nitrate; silica gel; sodium lactate

T=315°C; P=4500.4 Torr; 2.2 h; ΔE(excit.); var. temp. and time; Product distributionRate constantThermodynamic data;

Wadley, Douglas C.; Tam, Man S.; Kokitkar, Prashant B.; Jackson, James E.; Miller, Dennis J.

Journal of Catalysis, 1997 , vol. 165, # 2 art. no. CA971484, p. 162 - 171 Title/Abstract Full Text View citing articles Show Details

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A: 4.3% C: 1.9% D: 0.9% E: 0.6% F: 2%

With aluminum oxide; silica gel; sodium phosphate

T=300°C; P=3750.3 Torr; mechanism, var. sodium phosphate salts, temp. and contact times; Product distributionThermodynamic dataEquilibrium constant;

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Gunter, Garry C.; Miller, Dennis J.; Jackson, James E.

Journal of Catalysis, 1994 , vol. 148, # 1 p. 252 - 260 Title/Abstract Full Text View citing articles Show Details

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With water; sulfuric acid

T=385°C; P=258574 Torr; 0.00916667 h; other carboxylic acids; effects of pH, residence time, temperature, concentration, and solvent density; Product distributionMechanism;

Mok, William Shu-Lai; Antal, Michael Jerry; Jones, Maitland

Journal of Organic Chemistry, 1989 , vol. 54, # 19 p. 4596 - 4602 Title/Abstract Full Text View citing articles Show Details

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A: 3 %

With lt;PtH(PEt )3gt;OH in water

Odell, Barbara; Earlam, George; Cole-Hamilton, David J.

Chromat. B: 43 % Chromat. C: 1 % Chromat. D: 1 % Chromat. E: 3.4 % Chromat. F: 24 % Chromat.

T=230°C; 2 h; pH = 2; investigated effect of reaction conditions and the effect of different catalysts; Product distribution;

Journal of Organometallic Chemistry, 1985 , vol. 290, p. 241 - 248 Title/Abstract Full Text View citing articles Show Details

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A: 6.3 % Chromat. B: 50.5 % Chromat. C: 1.1 % Chromat. D: 24 % Chromat.

With lt;PtH(PEt3)3gt;OH in water

T=250°C; 0.25 h; pH = 2;

Odell, Barbara; Earlam, George; Cole-Hamilton, David J.

Journal of Organometallic Chemistry, 1985 , vol. 290, p. 241 - 248 Title/Abstract Full Text View citing articles Show Details

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A: 19 % Chromat. B: 13.0 % Chromat. C: 1 % Chromat.

With lt;PtH(PEt3)3gt;OH in water

T=220°C; 2 h; pH = 7;

Odell, Barbara; Earlam, George; Cole-Hamilton, David J.

Journal of Organometallic Chemistry, 1985 , vol. 290, p. 241 - 248 Title/Abstract Full Text View citing articles Show Details

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durch Clostridium propionicum;

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Cardon; Barker

Archives of Biochemistry, 1947 , vol. 12, p. 169 Full Text View citing articles Show Details

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aerobe Oxydation durch belueftete und gewaschene Kulturen von Propionibacterium arabinosum;

Erb,Wood,Werkman

J.Bacteriol., 1936 , vol. 31, p. 599 Chem. Zentralbl., 1936 , vol. 107, # II p. 1188 Full Text Show Details

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Vergaerung durch Abwasserbakterien;

Tarvin; Buswell

Journal of the American Chemical Society, 1934 , vol. 56, p. 1753 Full Text View citing articles Show Details

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T=270°C; P=53200 Torr; in Gegenwart Tonerde; Produkt 5: dl-Brenzweinsaeure;

Ipatjew; Rasuwajew

Chemische Berichte, 1926 , vol. 59, p. 2032 Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1926 , vol. 58, p. 1347 Full Text View citing articles Show Details

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bei der Einw. von Bac. propionicus;

Virtanen

Comment.phys.-math.Helsingfors, vol. 1, # 36 p. 2,11 Chem. Zentralbl., 1924 , vol. 95, # II p. 54 Full Text Show Details

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T=270 - 290°C;

Nef

Justus Liebigs Annalen der Chemie, 1904 , vol. 335, p. 323 Justus Liebigs Annalen der Chemie, 1907 , vol. 357, p. 215,300 Full Text View citing articles Show Details

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Rx-ID: 6681717

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Lautemann

Justus Liebigs Annalen der Chemie, 1860 , vol. 113, p. 217 Full Text View citing articles Show Details