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[ CAS No. 497-23-4 ]

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Chemical Structure| 497-23-4
Chemical Structure| 497-23-4
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CAS No. :497-23-4 MDL No. :MFCD00005376
Formula : C4H4O2 Boiling Point : 203.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :84.07 g/mol Pubchem ID :10341
Synonyms :

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Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 497-23-4 ]

  • Upstream synthesis route of [ 497-23-4 ]
  • Downstream synthetic route of [ 497-23-4 ]

[ 497-23-4 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 6305-38-0 ]
  • [ 50768-69-9 ]
  • [ 5061-21-2 ]
  • [ 497-23-4 ]
Reference: [1] Patent: KR2015/118287, 2015, A, . Location in patent: Paragraph 0095; 0109-0114
  • 2
  • [ 36603-83-5 ]
  • [ 96-48-0 ]
  • [ 627-00-9 ]
  • [ 497-23-4 ]
Reference: [1] Patent: KR2015/118287, 2015, A, . Location in patent: Paragraph 0154-0158
  • 3
  • [ 617-55-0 ]
  • [ 3068-00-6 ]
  • [ 52079-23-9 ]
  • [ 497-23-4 ]
  • [ 88246-12-2 ]
YieldReaction ConditionsOperation in experiment
97.9 - 98.8 % ee With hydrogen In Dimethyl ether at 56 - 110℃; for 0.5 - 2 h; HYDROGENATION OF DIMETHYL MALATE:; The following conditions were used Hydrogen pressure 0,1, 10 and 30 bar Substrate 0,4 and 1,5 molpercent Catalyst CuMn AI203, particle size 90-180 um Samples are taken at regular intervals after the substrate feed is started. Experiment 1: This was performed according to the procedure described above in Materials, Equipment and Activation Procedure. The reaction temperature was 56°C, Hydrogen pressure was 10bar, DME pressure was 150bar, substrate concentration in solution was 0.4 molpercent, and 10G of catalyst were used. The following results were obtained: Time on DM L DE BT HGB H-THF HGB equiv Selectivity stream areapercent areapercent 5 67.5 0.22 15.16 0.14 15.86 0.1 31.02 95.4percent 13 58.4 0.09 21.45 0.27 18.29 0.07 39.74 95.5percent 20 63.1 0.15 19.8 0.37 15.6 0.07 35.4 95.9percent 30 67.8 0.07 18.2 0.58 12.39 0.06 30.59 95.0percent 60 76.5 0.04 15 0.48 7.22 0.04 22.22 94.6percent DM = dimethyl malate L = 2 (5H)-Furanone DE = 3,4-dihydroxy methyl butyrate ester BT = butanetriol HGB = 3-hydroxy-gammabutyrolactone (produced by in-situ cyclisation of 3,4-dihydroxy methyl butyrate ester) H-THF = hydroxy-THF Notes: HGB EQUIVALENT = areapercent"HGB"+ areapercent"Dihydroxy ester" (as hydroxy ester can be cyclise to HGB) SELECTIVITY DEFINED AS (AREApercent USEFUL PRODUCTS) / (AREA percent OF ALL PRODUCTS) HGB (S) was obtained in 97.9percent ee Experiment 2: This was performed according to the procedure described above in Materials, Equipment and Activation Procedure. The reaction temperature was 110°C, Hydrogen pressure was 10bar, DME pressure was 150bar, substrate concentration in solution was 1.5 molpercent, and 5.9g of catalyst were used. The following results were obtained : Time on DM L DE BT HGB H-THF HGB equiv Selectivity stream areapercent areapercent 5 64.1 0.55 18.22 1.6 15.3 33.52 93.4percent 15 72.6 0.24 15.38 0.9 10 0.1 25.38 92.6percent 30 77.6 0.16 13.3 0.5 7.8 0.1 21.1 94.2percent Note: HGB (S) obtained in 98.8percent ee Conclusion: These experiments illustrate high selectivity for HGB in the hydrogenation of dimethyl malate EXPERIMENT-MEOH removal and the effect on the conversion of LDMM to HGB Experiment 3: This was performed according to the procedure described above in Materials, Equipment and Activation Procedure. The reaction temperature was 80°C, Hydrogen pressure was 10bar, DME pressure was 150bar, substrate concentration in solution was 0.4 molpercent, and 87g of catalyst were used. After 2 hours on stream, the product was found to contain 39.8 areapercent starting material and 51.5 areapercent HGB-EQUIVALENT (as defined in Example 1). The product was formed with 85.5percent selectivity. The collected product from this experiment, after depressurisation and removal of Methanol, was used as the feed for another hydrogenation, under otherwise identical conditions. The following results were obtained. Time on DM areapercent L DE BT HGB HGB Selectivity stream equiv areapercent 50 14.7 5.3 15.2 8 47.4 62.6 73.4percent 60 18. 8 4.4 14. 8 11.7 45.5 60.3 74.3percent 75 21.15 3.7 21.1 11.5 43.2 64. 3 81.5percent 90 13. 4 7. 1 5.5 59.1 66.2 76.4percent 105 26.7 3.4 17.5 8.7 40.6 58. 1 79.3percent 120 25.6 2.3 17.7 9.5 42 59.7 80. 2percent Conclusions : When the reaction products from one incomplete hydrogenation are depressurised and Methanol removed by evaporation, then re-hydrogenated the conversion is increased FROM-50percent TO-60percent, and the selectivity remains approximately constant.
Reference: [1] Patent: WO2005/23737, 2005, A1, . Location in patent: Page/Page column 10-12
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