4-hydroxybutanal synthesis

13synthesis methods

Product Name:4-hydroxybutanal
CAS Number:25714-71-0
Molecular formula:C4H8O2
Molecular Weight:88.11

The 4-hydroxybutanal which is produced as the high yield product of the invention hydroformylation process can be separated and recovered by conventional distillation procedures. It is highly preferred, however, to subject the hydroformylation product mixture to aqueous phase extraction. Surprisingly it was found that water is capable of extracting 4-hydroxybutanal from the product mixture substantially to the exclusion of the other product mixture components. In a commercial scale operation, an aqueous phase stream can be contacted countercurrently and continuously with reaction product effluent from the hydroformylation reaction zone. The resultant aqueous phase containing 4-hydroxybutanal is an excellent vehicle for subsequent processing procedures, such as hydrogenation of 4-hydroxybutanal with Raney nickel to produce valuable 1,4-butanediol.
literature source US04064145

201230-82-2 Synthesis

201230-82-2
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107-18-6
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38433-80-6
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25714-71-0
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$195.00/100mg

Yield:25714-71-0 54.99% ，38433-80-6 34.7%

Reaction Conditions:

with (S_a)-1,16-bis(diphenylphosphino)-6,7,8,9,10,11-hexahydrodibenzo[b,d][1,6]dioxacyclododecine;hydrogen in toluene under 9308.91 - 10343.2 Torr;Autoclave;Overall yield = 91.27 %;Reagent/catalyst;

Steps:

2 i. Hydroforniylation Conditions
General procedure: [0060] The hydroformylation experiments were carried out in anhydrous toluene with the stoichiometry determined by the amount of Rh. In a typical experiment, a rhodium complex ( 1 equivalent, 4.3 ^χ If)^"5 moles) was added to this solution of dry degassed toluene (15 g) and the desired phosphine ligand. This solution was then transferred to a 50 mL Parr autoclave. The autoclave was then flushed three times with a 1 : 1 CO/H₂ mixture, and pressurized to 180 psi (1240 kPa), and the autoclave was heated with stirring, to the indicated temperature, for example 80 °C. Once the desired temperature was stably attained for at least 5 minutes, allyl alcohol (3.5 mL) was then injected and the autoclave pressure increased to 200 psi (1,379 kPa) with the CO:H₂ mixture. The reactor was then maintained at a constant 200 psi (1 ,379 kPa) pressure and the gas uptake with time was monitored until there was no further gas uptake. The reactor was cooled down, depressurized and the solution was analyzed by gas chromatography to determine the products of the reaction, which included HBA, MHPA and C3 products, (n-propanol and Propionaldehyde). Results are shown in Tables 2 and 4.

References:

LYONDELL CHEMICAL TECHNOLOGY, L.P.;WHITE, Daniel, F.;MANDIMUTSIRA, Beaven, S. WO2017/79171, 2017, A1 Location in patent:Paragraph 0061

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