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Chemical Structure| 4254-14-2 Chemical Structure| 4254-14-2
Chemical Structure| 4254-14-2

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(R)-(-)-1,2-Propanediol is the (R)-enantiomer of 1,2-Propanediol, produced by Escherichia coli expressing the NADH-linked glycerol dehydrogenase gene. (R)-(-)-1,2-Propanediol has low toxicity and moisturizing properties, commonly used in food additives and cosmetics.

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Product Details of (R)-(-)-1,2-Propanediol

CAS No. :4254-14-2
Formula : C3H8O2
M.W : 76.09
SMILES Code : C[C@@H](O)CO
MDL No. :MFCD00066248
InChI Key :DNIAPMSPPWPWGF-GSVOUGTGSA-N
Pubchem ID :259994

Safety of (R)-(-)-1,2-Propanediol

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H319
Precautionary Statements:P305+P351+P338

Application In Synthesis of (R)-(-)-1,2-Propanediol

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 4254-14-2 ]

[ 4254-14-2 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 4254-14-2 ]
  • [ 105-58-8 ]
  • [ 16606-55-6 ]
YieldReaction ConditionsOperation in experiment
90% at 105 - 110℃; for 8 h; Large scale R - Preparation of propylene carbonate,R-1,2-propanediol was added to a glass-lined reactor(38.05 kg, 500Mol),Diethyl carbonate(70.88 kg, 600 mol) and (3.4 kg, 50 mol) of sodium ethoxide,Heated to 105-110 ° C,Reaction for 8 hours,The reaction is terminated,The unreacted diethyl carbonate was distilled off under reduced pressure,Cooled to room temperature,Filter insoluble matter,The filtrate was evaporated to remove the solvent of product R - propylene carbonate 34.24 kg,Purity ≥ 99percentThe yield was 90percent.
81.2% With sodium methylate In ethanol at 80℃; Example 1
Preparation of (R)-4-methyl-1,3-dioxolan-2-one
To the mixture of diethyl carbonate (380 ml, 15.1 mol) and 200 g of (R)-1,2-propanediol was added 40 ml of denatured ethanol (the solution of 9 g sodium methoxide dissolved in 50 ml of anhydrous ethanol), the resulting solution was heated to 80° C., then ethanol was distilled off slowly.
The reaction process was monitored by TLC, after TLC showed that only trace amount of (R)-1,2-propanediol remained or (R)-1,2-propanediol was undetectable, ethanol was distilled under vacuum by water pump at 120° C. until no ethanol dropped out.
The residue was distilled under vacuum to give the title compound as a colorless transparent liquid (111 g, 81.2percent yield, purity 97percent by GC)
44.5 g With sodium ethanolate In ethanol at 80℃; The 1000 ml hydrogenation vessel was evacuated and then passed through nitrogen,Then add 500ml ethanol, 2g5percent Pd / C, 2.5g caustic soda, cool to -10 ,Slowly add 50g of S-glycidol,Then, hydrogen gas (about 2 atmospheres) was passed for 4 hours,To no longer consume hydrogen so far, filtered and concentrated to give 48 g of a colorless oil.
References: [1] Patent: CN105859781, 2016, A, . Location in patent: Paragraph 0011-0012.
[2] Patent: US2010/216822, 2010, A1, . Location in patent: Page/Page column 13.
[3] Tetrahedron Letters, 1998, vol. 39, # 14, p. 1853 - 1856.
[4] Patent: EP1243590, 2002, A2, . Location in patent: Page 9.
[5] Patent: CN102977146, 2016, B, . Location in patent: Paragraph 0016; 0021; 0023.
[6] Patent: CN108358968, 2018, A, . Location in patent: Paragraph 0073; 0087-0089; 0134-0136; 0142-0144; 0150-0152.
[7] Patent: JP2015/164934, 2015, A, . Location in patent: Paragraph 0166; 0167; 0173.
  • 2
  • [ 4254-14-2 ]
  • [ 616-38-6 ]
  • [ 16606-55-6 ]
References: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 23, p. 2931 - 2938.
 

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