4704-94-3

Usage

Uses

Used in Chemical Synthesis:
2-(HYDROXYMETHYL)-1,3-PROPANEDIOL is used as a reactant for the preparation of tetracyanocyclopentadienide amine salts. Its versatility as a reactant allows for the creation of various chemical compounds, contributing to its importance in the chemical industry.
In addition to the provided material, Glycerol has several other applications across different industries:
Used in Pharmaceutical Industry:
Glycerol is used as a solvent, sweetening agent, and humectant in the pharmaceutical industry. It is also utilized in the production of various drugs, including antifreeze and as a component in the formulation of certain elixirs and expectorants.
Used in Cosmetics and Personal Care Industry:
In the cosmetics and personal care industry, Glycerol is used as a moisturizer, humectant, and emollient in products such as lotions, creams, and toothpaste. Its ability to retain moisture makes it a valuable ingredient in skincare and hair care products.
Used in Food Industry:
Glycerol is used as a humectant, sweetener, and preservative in the food industry. It is commonly found in the production of confectionery, baked goods, and as a component in the formulation of certain beverages.
Used in Energy Industry:
Glycerol is used as a feedstock for the production of biofuels, such as biodiesel and bio-jet fuel. Its ability to be derived from renewable resources makes it a sustainable option for energy production.
Used in Textile Industry:
In the textile industry, Glycerol is used as a humectant, lubricant, and plasticizer in the manufacturing of various fabrics and fibers, enhancing their softness and flexibility.
These applications highlight the diverse uses of 2-(HYDROXYMETHYL)-1,3-PROPANEDIOL across different industries, showcasing its importance and versatility as a compound.

Synthesis Reference(s)

Synthesis, p. 742, 1987 DOI: 10.1055/s-1987-28072

InChI:InChI=1/C4H10O3/c5-1-4(2-6)3-7/h4-7H,1-3H2

Synthetic route

2-Benzoyloxymethyl-1,3-propanediol dibenzoate (113967-50-3) → 2-hydroxymethyl-1,3-propanediol (4704-94-3)

Conditions	Yield
With sodium methylate In methanol for 20h; Heating;	98%
With sodium methylate In methanol for 20h; Time; Reflux;	90%

[2-(4-methoxyphenyl)-[1,3]dioxan-5-yl]methanol (465540-17-4) → 2-hydroxymethyl-1,3-propanediol (4704-94-3)

Conditions	Yield
With water; Selectfluor In acetonitrile at 20℃; for 5h;	90%

methanetricarboxylic acid triethyl ester (6279-86-3) → 2-hydroxymethyl-1,3-propanediol (4704-94-3)

Conditions	Yield
With dimethylsulfide borane complex 1.) reflux, 8 h, 2.) methanol, 15 h;	83%
With lithium aluminium tetrahydride; diethyl ether

bis-(hydroxymethyl)-acetaldehyde (40364-80-5) → 2-hydroxymethyl-1,3-propanediol (4704-94-3)

Conditions	Yield
With hydrogen; ruthenium In water at 25℃; under 2585.7 Torr; for 24h; Yield given;
PtO2 In water

formaldehyd (50-00-0) + acetaldehyde (75-07-0) → 2,2-di(hydroxymethyl)-acetic acid (68516-39-2) + Pentaerythritol (115-77-5) + 2-hydroxymethyl-1,3-propanediol (4704-94-3) + α,α,α-tris(hydroxymethyl)acetic acid (2831-90-5) + 2-Hydroxymethyl-2-(methoxymethoxymethyl)-1,3-propandiol (68658-38-8) + trimethyleneglycol (504-63-2)

Conditions	Yield
With calcium hydroxide Mechanism;

formaldehyd (50-00-0) + acetaldehyde (75-07-0) → Pentaerythritol (115-77-5) + 2-methyl-1.3-propanediol (2163-42-0) + 2-hydroxymethyl-1,3-propanediol (4704-94-3) + trimethyleneglycol (504-63-2)

Conditions	Yield
With sodium hydroxide; sulfuric acid; hydrogen; 5% activated charcoal-supported ruthenium catalyst 1.) 25 deg C, 30 min, 2.) 50 psi, 25 deg C, 4 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
With sodium hydroxide; sulfuric acid; hydrogen; Ru-carbon 1.) 25 deg C, 30 min, 2.) 50 psi, 25 deg C 4 h; Yield given. Multistep reaction. Yields of byproduct given;

formaldehyd (50-00-0) + acrolein (107-02-8) → 2-hydroxymethyl-1,3-propanediol (4704-94-3) + trimethyleneglycol (504-63-2)

Conditions	Yield
With sulfuric acid; hydrogen; iron(II) sulfate; palladium on activated charcoal; Ru-carbon 1.) 25 deg C, 5 h, 2.) 50 psi, 25 deg C, 42 h; Yield given. Multistep reaction. Yields of byproduct given;

glycerol tristearate (555-43-1) → 2-hydroxymethyl-1,3-propanediol (4704-94-3) + stearic acid (57-11-4)

Conditions	Yield
With lipase from Pseudomonas stutzeri PS59 In aq. phosphate buffer; isopropyl alcohol at 30℃; for 0.25h; pH=8; Enzymatic reaction;

glyceroltripalmitate (555-44-2) → 2-hydroxymethyl-1,3-propanediol (4704-94-3) + 1-hexadecylcarboxylic acid (57-10-3)

Conditions	Yield
With lipase from Pseudomonas stutzeri PS59 In aq. phosphate buffer; isopropyl alcohol at 30℃; for 0.25h; pH=8; Enzymatic reaction;

trioleoylglycerol (122-32-7) → cis-Octadecenoic acid (112-80-1) + 2-hydroxymethyl-1,3-propanediol (4704-94-3)

Conditions	Yield
With lipase from Pseudomonas stutzeri PS59 In aq. phosphate buffer; isopropyl alcohol at 30℃; for 0.25h; pH=8; Enzymatic reaction;

Upstream product

• 6279-86-3 methanetricarboxylic acid triethyl ester 
• 113967-50-3 2-Benzoyloxymethyl-1,3-propanediol dibenzoate 
• 122-32-7 trioleoylglycerol 
• 555-44-2 glyceroltripalmitate 
• 555-43-1 glycerol tristearate 
• 465540-17-4 [2-(4-methoxyphenyl)-[1,3]dioxan-5-yl]methanol 
• 50-00-0 formaldehyd 
• 107-02-8 acrolein 
• 75-07-0 acetaldehyde 
• 40364-80-5 bis-(hydroxymethyl)-acetaldehyde 

Downstream Products

• 465540-17-4 [2-(4-methoxyphenyl)-[1,3]dioxan-5-yl]methanol 
• 4728-07-8 5-hydroxymethyl-1,3-dioxane 
• 155850-41-2 Tris<(diphenylphosphanyl)methyl>methan 
• 367970-16-9 2-fudroxymethyl-3-hydroxypropyl 3,5-dinitrobenzoate 
• 4728-12-5 2,2-dimethyl-5-hydroxymethyl-1,3-dioxane 
• 1255304-21-2 {3-[4-(4-cyclopropylbenzyloxy)-3-methoxyphenyl]azetidin-1-yl}-[4-(3-hydroxy-2-hydroxymethylpropoxymethyl)pyridin-2-yl]methanone 

Relevant academic research and scientific papers

Preparation method of 3-oxetanecarboxylic acid

The invention provides a preparation method of 3-oxetanecarboxylic acid. According to the preparation method, 2-hydroxymethyl-2-nitro-1,3-propylene glycol is taken as a raw material, hydroxyl in 2-hydroxymethyl-2-nitro-1,3-propylene glycol is subjected to a group protection reaction, nitryl in 2-hydroxymethyl-2-nitro-1,3-propylene glycol is subjected to a reductive elimination reaction and hydrolysis reaction, and 2-hydroxymethyl-1,3-propylene glycol is obtained; 2-hydroxymethyl-1,3-propylene glycol is continuously subjected to a cyclization reaction and an oxidation reaction, and 3-oxetanecarboxylic acid is obtained. The provided preparation method can be completed only through five-step reactions; compared with existing preparation methods through ten-step reactions, the preparation method has the advantages that the reaction steps are greatly reduced, the reaction routes are greatly shortened, the overall yield is increased, and the final yield can be up to 50% or above on the basisof the raw material, namely, 2-hydroxymethyl-2-nitro-1,3-propylene glycol; the related reactions are simple, and the method is easy to operate and favorable for industrial production.

A high-detergent-performance, cold-adapted lipase from Pseudomonas stutzeri PS59 suitable for detergent formulation

A high-detergent-performance and cold-adapted lipase was purified and characterised from Pseudomonas stutzeri PS59, which was isolated from Daqing oil fields (Heilongjiang, PR China). The lipase was purified to homogeneity using ammonium sulphate precipitation, dialysis, freeze-drying, ion exchange chromatography and gel filtration chromatography. The molecular weight of the lipase was approximately 55 kDa, as measured by SDS-PAGE. The lipase showed optima activity at pH 8.5 and 20 C. The lipase activity was activated by metal ions, such as Ca2+ and Mn2+, and surfactants, such as Tween 80, Tween 20, sodium dodecyl benzene sulfonate and urea. Oxidising agents, such as H2O2 and NaClO, were found to have little effect on the activity of the lipase, and most organic solvents can enhance the activity of the lipase. The broad substrate specificity and the compatibility of the lipase in the presence of surfactants, oxidising agents, and other detergent additives clearly indicate its potential application in the laundry industry. The hydrolysis resolution of (R,S)-ethyl 2-methylbutyrate by P. stutzeri PS59 lipase was carried out with the yield of 31.2% for R-ethyl 2-methylbutyrate, the enantiomeric excess of residual substrate (ees) was 85.7%. Thus, the lipase also showed an attractive potency for application in biocatalysis.

An efficient method for the cleavage of p-methoxybenzylidene (PMP), tetrahydropyranyl (THP) and 1,3-dithiane protecting groups by Selectfluor

A new and efficient method for the cleavage of the PMP, THP and 1,3-dithiane protecting groups with Selectfluor has been developed.

Synthesis and antiviral activity of 9-alkoxypurines. 1. 9-(3-Hydroxypropoxy)- and 9-[3-hydroxy-2-(hydroxymethyl)propoxy]purines

Reaction of hydroxyl-protected derivatives of hydroxyalkoxyamines (3a,b,c) with either 4,6-dichloro-2,5-diformamidopyrimidine (5) or 4,6-dichloro-5-formamidopyrimidine (31) and subsequent cyclization of the resultant 6-(alkoxyamino)pyrimidines (6, 17, 32, 35) by heating with diethoxymethyl acetate afforded 9-alkoxy-6-chloropurines (7, 18, 33, 36), which were converted subsequently to 9-(3-hydroxypropoxy)- and 9-[3-hydroxy-2-(hydroxymethyl)propoxy] derivatives of guanine, 2-amino-6-chloropurine, 2-amino-6-alkoxypurines, 2-aminopurine, 2,6-diaminopurine, adenine, hypoxanthine, and 6-methoxypurine (8, 12, 13, 19-21, 23-26, 34, 37-39). Carboxylic acid esters (9-11, 14-16, 27-29) and a cyclic phosphate derivative (22) of the 9-(hydroxyalkoxy)guanines (8, 21) and 2-amino-9-(hydroxyalkoxy)purines (13, 26) were also prepared. The guanine derivatives (8, 21) showed potent and selective activity against herpes simplex virus types 1 and 2 and varicella zoster virus in cell cultures and 8 is more active than acyclovir. Although without significant antiviral activity in cell cultures, the 2-aminopurines (13, 14-16, 26-29) and 2-amino-6-alkoxypurines (12, 23-25) are well absorbed after oral administration to mice and are converted efficiently to the antiviral guanine derivatives (8, 21) in vivo.

Simple Syntheses of 2-Hydroxymethyl-1,3-propanediol and Related Compounds

A significantly improved synthesis of 2-hydroxymethyl-1,3-propanediol involves benzoylation of 2-hydroxymethyl-2-nitro-1,3-propanediol, replacement of the nitro group by hydrogen using tributylstannane, and methanolysis.Other simple procedures yield the corresponding trimethanesulfonate, triiodide, and trichloride.Dehydrohalogenation of the triiodide and the trichloride by DBU provides 3-iodo-2-(iodomethyl)propene and the corresponding dichloride, respectively.All of these useful compounds are now readily available for the first time.

Derivatives of Pentaerythritol, IV. - Identification of By-products in Pentaerythritol Process Liquors

Several previously unknown by-products of the pentaerythritol synthesis were identified by comparison of their GC/MS spectra with the spectra of pure compounds.Furthermore, pure 2-hydroxymethyl-2-(methoxymethoxymethyl)-1,3-propandiol (5) was isolated from mother liquors, and the reference compounds 5-hydroxymethyl-1,3-dioxane-5-carboxylic acid (6) and 3--2,2-bis(hydroxymethyl)propanoic acid (7) were synthesized.

2-Hydroxymethyl-1,3-propanediol preparation

2-Hydroxymethyl-1,3-propanediol trinitrate, processes for its preparation, and compounds related thereto are disclosed. The final product is useful as a plasticizer of relatively low volatility in double based propellant compositions and as a liquid explosive.

A 13C AND 1H NMR STUDY OF FORMALDEHYDE REACTIONS WITH ACETALDEHYDE AND ACROLEIN. SYNTHESIS OF 2-(HYDROXYMETHYL)-1,3-PROPANEDIOL

The 13C i 1H NMR spectra of various formaldehyde-acetaldehyde and formaldehyde-acrolein mixtures in buffered aqueous solutions were examined.Reaction intermediates and products were assayed including 3-hydroxypropanal, 3-hydroxy-2-(hydroxymethyl)propanal, pentaerythrose and pentaerythritol.Reaction mixtures were hydrogenated under various conditions to yield mixtures of 1,3-propanediol, pentaerythritol and 2-(hydroxymethyl)-1,3-propanediol.The latter compound was also prepared by an efficient new procedure from 3,3-diethoxy-2-(hydroxymethyl)-1-propanol.