96-23-1

Basic information

• Product Name: 1,3-Dichloro-2-propanol
• Synonyms: 1,3-Dichloro-2-hydroxypropane;1,3-Dichlorohydrin;1,3-Dichloroisopropanol;1,3-Dichloroisopropyl alcohol;2-Chloro-1-(chloromethyl)ethanol;Bis(chloromethyl)methanol;Glycerol 1,3-dichlorohydrin;Glycerol a,g-dichlorohydrin;NSC 70982;Propylene dichlorohydrin;sym-Dichloroisopropyl alcohol;sym-Glycerol dichlorohydrin;a,g-Dichlorohydrin;a-Dichlorohydrin
• CAS NO: 96-23-1
• Molecular Formula: C₃H₆Cl₂O
• Molecular Weight: 128.98514
• EINECS: 202-491-9
• Mol File: 96-23-1.mol

Chemical Properties

• Melting Point: -4℃
• Boiling Point: 174.3 °C at 760 mmHg
• Flash Point: 85.6 °C
• Appearance: Colorless to light yellow liquid
• Density: 1.306 g/cm³
• Vapor Pressure: 0.0366mmHg at 25°C
• Refractive Index: 1.462
• PKA: 12.87±0.20(Predicted)
• Water Solubility: soluble. >=10 g/100 mL at 23℃
• CAS DataBase Reference: 1,3-Dichloro-2-propanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dichloro-2-propanol(96-23-1)
• EPA Substance Registry System: 1,3-Dichloro-2-propanol(96-23-1)

Safety Data

• Hazard Codes: T:Toxic
• Statements: R21:; R25:; R45:
• Safety Statements: S45:; S53:
• RIDADR: 2750
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 96-23-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Production:
1,3-Dichloro-2-propanol is used as a chemical intermediate for the synthesis of other compounds, playing a significant role in the creation of a wide range of products.
Used in Industrial Applications:
1,3-Dichloro-2-propanol is used as a solvent in industrial processes, particularly in paint and varnish removers, due to its ability to dissolve a variety of substances.
Used in Pharmaceutical Production:
Within the pharmaceutical industry, 1,3-Dichloro-2-propanol is utilized as a chemical intermediate in the manufacturing of certain medications, contributing to the development of new treatments and therapies.
Used in Pesticide Production:
In agriculture, 1,3-Dichloro-2-propanol is employed in the production of pesticides, serving as a component in the formulation of products designed to protect crops from pests and diseases.
However, due to its potentially hazardous nature, 1,3-Dichloro-2-propanol requires careful handling to prevent irritation to the skin, eyes, and respiratory tract, as well as to minimize systemic effects on the liver and kidneys. Adherence to proper safety protocols is essential when working with this chemical.

InChI:InChI=1/C3H6Cl2O/c4-2-1-3(5)6/h3,6H,1-2H2

Upstream product

• 60-29-7 diethyl ether 
• 513-88-2 1,1-Dichloroacetone 
• 555-75-9 aluminum ethoxide 
• 75-07-0 acetaldehyde 
• 534-07-6 1,3-Dichloroacetone 
• 96-24-2 3-monochloro-1,2-propanediol 
• 56-81-5 glycerol 
• 107-05-1 3-chloroprop-1-ene 
• 110-86-1 pyridine 
• 90-02-8 salicylaldehyde 
• 106-89-8 epichlorohydrin 
• 108-95-2 phenol 
• 123-51-3 i-Amyl alcohol 
• 463-72-9 carbamic chloride 

Downstream Products

• 13429-29-3 1,3-bispiperidin-1-ylpropan-2-ol 
• 7250-87-5 1,3-bismorpholinopropan-2-ol 
• 43015-17-4 1,3-dipropyl glycerol 
• 53883-86-6 2-(chloromethoxy)-1,3-dichloropropane 
• 18587-81-0 bis-(β,β'-dichloro-isopropoxy)-methane 
• 5855-89-0 1,2,3,4-tetrahydro-benzo[h]quinoline-3,7-diol 
• 14569-62-1 1,3-bis(4-methylphenoxy)propan-2-ol 
• 2186-24-5 cresyl-glicidyl ether 
• 405-32-3 1,3-bis-(4-fluoro-phenoxy)-propan-2-ol 
• 2212-06-8 2-((4-bromophenoxy)methyl)oxirane 
• 587-01-9 carbamic acid-(β,β'-dichloro-isopropyl ester) 
• 13880-89-2 3-hydroxyglutaronitrile 
• 4043-59-8 1,3-diethoxy-isopropanol 
• 59068-03-0 5,13-diethyl-7,11-dioxa-9-heptadecanol 

Relevant articles and documents

Unconventional reactivity of epichlorohydrin in the presence of triphenylphosphine: isolation of ((1,4-dioxane-2,5-diyl)-bis-(methylene))-bis-(triphenylphosphonium) chloride

The selective formation of the heterocyclic salt ((1,4-dioxane-2,5-diyl)-bis-(methylene))-bis-(triphenylphosphonium) chloride was observed when epichlorohydrin and triphenylphosphine were reacted in CH2Cl2 at room temperature. Slow evaporation from a mixture of ethanol and ethyl acetate allows to isolate monocrystals of the heterocyclic phosphonium salt. Mechanistic investigations point to the formation of the zwitterionic intermediate 1-chloro-3-(triphenylphosphonio)-propan-2-olate, which can dimerize and generate the 1,4-dioxane derivative. In the exclusive presence of a Br?nsted acid as HCl, which usually facilitates epoxide ring opening, the exclusive formation of 1,3-dichloro-2-propanol was although observed. Also, when epichlorohydrin, PPh3, and a stoichiometric amount of HCl were mixed, (2-chloro-3-hydroxypropyl)-triphenylphosphonium chloride was formed and its isolation in pure form provides monocrystals subjectable to X-ray analysis.

Preparation method for 1,3-propylene glycol from glycerol

The invention relates to a preparation method for 1,3-propylene glycol from glycerol, wherein the preparation method comprises the steps of chlorohydrination reaction, cyclization reaction, hydrogenation reaction and the like. The glycerin conversion rate of the preparation method reaches 99% or above, the yield of 1,3-propylene glycol reaches 65% or above, and the preparation method has the advantages of being simple in process, mild in reaction condition, small in investment, high in technical safety and easy to operate and control.

A method for efficient preparation of epichlorohydrin by biomass glycerol

The present invention discloses a method for efficiently preparing epichlorohydrin by biomass glycerol, comprising the following steps: 1) the mass ratio of 1: 0.06 ~ 0.08 of biomass glycerol and a composite catalyst poured into the reactor, and then using an ultrasonic probe to extend into the reactor, 2) step 1) after the end of the reaction, the resulting material is cooled to room temperature and transferred to the reaction vessel, maintaining a temperature of 15 ~ 30 ° C, and then adding an alkaline cyclizer for the reaction; 3) after the completion of the reaction to filter the resulting solids, The filtrate is a solution of epichlorohydrin oxide; the glycerol of the present invention can be completely converted, the intermediate product dichloropropanol yield is high, and the selectivity of collecting 1,3-dichloropropanol is improved, which accelerates the reaction rate; and the process can be co-produced with biodiesel and chlor-alkali industry, and the industrialization prospect is good.

Preparation method of sodium beta-glycerophosphate containing crystal water

The invention discloses a preparation method of sodium beta-glycerophosphate containing crystal water. The method comprises the following steps: A) taking epoxy chloropropane as an initial raw material, slowly dropwise adding the epoxy chloropropane into hydrochloric acid, reacting for 1-6 hours, adjusting the pH value to 3-4 by using a sodium hydroxide solution, carrying out vacuum distillation to remove moisture, distilling to 60 DEG C, adding a drying agent, stirring for 1 hour, and filtering to obtain 1, 3-dichloropropanol; B) adding the 1,3-dichloropropanol into an esterification reactionkettle, adding a phosphating agent, heating the temperature to 80-130 DEG C, controlling the temperature to esterify for 10-20 hours, after esterification is finished, adding water for dilution, dropwise adding the sodium hydroxide solution, adjusting the pH value to be 9-13, keeping the temperature at 40-80 DEG C, hydrolyzing for 3-5 hours, adding magnesium oxide or calcium oxide and stirring for 2 hours at 60-80 DEG C, adding activated carbon and stirring for 1 hour, the negative pressure distillation concentration being 70%-75%, adding ethyl alcohol, carrying out cooling and stirring and filtering to obtain the sodium beta-glycerophosphate. According to the invention, the generation of sodium alpha-glycerophosphate is avoided, and the sodium beta-glycerophosphate containing crystal water and not containing crystal water can be flexibly prepared.

Expeditious Syntheses to Pharmochemicals 1,3-Dihydroxyacetone, 1,3-Dichloro-, 1,3-Dibromo- And 1,3-Diiodoacetone from Glycerol 1,3-Dichlorohydrin Using Homogenous and Heterogenous Medium

New efficient and reproductive routes to production of 1,3-dihydroxyacetone (1), 1,3-dichloroacetone (6), 1,3-dibromoacetone (7) and 1,3-diiodoacetone (8) from glycerol 1,3-dichlorohydrin (3) were developed. The synthesis of 1 was processed in three steps from glycerol 2 (1,3-selective chlorination of 2 to 3, oxidation of 3 to 6 and subsequent di-hydroxylation) in 51% overall yield. On the other hand, 7 and 8 were produced from 3, via a trans-bromination and trans-iodination, respectively, followed by oxidation and hydroxylation steps, in 38-52% overall yield. It was used homogeneous media with different reagents (HCl/AcOH, pyridinium chlorochromate (PCC), PCC-HIO4) and heterogeneous media with reagents supported on polymer resins such as Amberlyst A26-HCrO4– form, PV-PCC (polyvinyl-pyridinium chlorochromate) and Amberlyst A26-OH– form or reagents supported on alumina such as KI/Al2O3, KBr/Al2O3, in solvent free conditions.

Continuous flow upgrading of glycerol toward oxiranes and active pharmaceutical ingredients thereof

A robust continuous flow procedure for the transformation of bio-based glycerol into high value-added oxiranes (epichlorohydrin and glycidol) is presented. The flow procedure features a central hydrochlorination/dechlorination sequence and provides economically and environmentally favorable conditions involving an organocatalyst and aqueous solutions of hydrochloric acid and sodium hydroxide. Pimelic acid (10 mol%) shows an exceptional catalytic activity (>99% conversion of glycerol, a high selectivity toward 1,3-dichloro-2-propanol and 81% cumulated yield toward intermediate chlorohydrins) for the hydrochlorination of glycerol (140 °C) with 36 wt% aqueous HCl. These conditions are validated on a sample of crude bio-based glycerol. The dechlorination step is effective (quantitative conversion based on glycerol) with concentrated aqueous sodium hydroxide (20 °C) and can be directly concatenated to the hydrochlorination step, hence providing a ca. 2:3 separable mixture of glycidol and epichlorohydrin (74% cumulated yield). An in-line membrane separation unit is included downstream, providing usable streams of epichlorohydrin (in MTBE, with an optional concentrator) and glycidol (in water). The scalability of the dechlorination step is then assessed in a commercial pilot-scale continuous flow reactor. Next, bio-based epichlorohydrin is further utilized for the continuous flow preparation of β-amino alcohol active pharmaceutical ingredients including propranolol (hypertension, WHO essential), naftopidil (prostatic hyperplasia) and alprenolol (angina pectoris) within a concatenable two-step procedure using a FDA class 3 solvent (DMSO). This work provides the first example of direct upgrading of bio-based glycerol into high value-added pharmaceuticals under continuous flow conditions.

Laminaria digitata and palmaria palmata seaweeds as natural source of catalysts for the cycloaddition of CO2 to Epoxides

Seaweed powder has been found to act as an effective catalyst for the fixation of CO2 into epoxides to generate cyclic carbonates under solvent free conditions. Model background reactions were performed using metal halides and amino acids typically found in common seaweeds which showed potassium iodide (KI) to be the most active. The efficacy of the seaweed catalysts kelp (Laminaria digitata) and dulse (Palmaria palmata) was probed based on particle size, showing that kelp possessed greater catalytic ability, achieving a maximum conversion and selectivity of 63.7% to styrene carbonate using a kelp loading of 80% by weight with respect to epoxide, 40 bar of CO2, 120?C for 3 h. Maximizing selectivity was difficult due to the generation of diol side product from residual H2O found in kelp, along with a chlorinated by-product thought to form due to a high quantity of chloride salts in the seaweeds. Data showed there was loss of organic matter upon use of the kelp catalyst, likely due to the breakdown of organic compounds and their subsequent removal during product extraction. This was highlighted as the likely cause of loss of catalytic activity upon reuse of the Kelp catalyst.

Effect of sodium chloride on the solubility and hydrolysis of epichlorohydrin in water

The mutual solubility of the components in the epichlorhydrin–water–sodium chloride system was studied in the temperature range of 20–90 °С. It was found that epichlorohydrin is salted out as the concentration of NaCl increases. The Sechenov coefficient was determined to be equal to 0.29. It was found that epichlorohydrin reacts with an aqueous solution of sodium chloride to form glycerol dichlorohydrins. Alkali formed during this reaction catalyzes the hydrolysis of epichlorohydrin to glycerol monochlorohydrin, acts as a reagent in the glycidol formation and accelerates its subsequent conversion to glycerol.

Method for preparing 1,3-dichloro-2-propanol

The present invention discloses a method for preparing 1,3-dichloro-2-propanol. The method comprises the following steps: performing a contact reaction on allyl chloride, hydrogen chloride, an oxidantand an oxygen-containing hydrocarbon in the presence of a catalyst, wherein the oxygen-containing hydrocarbon is an alcohol and/or a carboxylic acid, and the catalyst is a titanium silicate molecularsieve catalyst. The method has the advantages of no use of toxic chlorine, simple operation process, mild reaction conditions, high selectivity of 1,3-dichloro-2-propanol, and easy separation of thecatalyst.

A safer and greener chlorohydrination of allyl chloride with H2O2 and HCl over hollow titanium silicate zeolite

Industrial production of dichloropropanols through chlorohydrination of allyl chloride suffers from a series of disadvantages such as use of hazardous Cl2, low atom economy, low dichloropropanol concentration and serious pollution. In this work, a safer and greener route for chlorohydrination of allyl chloride with H2O2 and HCl over hollow titanium silicate (HTS) at mild condition is developed. Unlike the traditional Cl2-based chlorohydrination, this novel method is initiated via synergistic effect of Lewis acidity (HTS) and Br?nsted acidity (HCl) to promote occurrence of oxidation, protonation and nucleophilic reaction of allyl chloride simultaneously and hence dichloropropanols are generated. Owing to a completely different reaction route, the formation of 1,2,3-trichloropropane by-product is depressed and the content of dichloropropanol exceeded 22?wt%, which increase by about 4 times compared with traditional Cl2-based chlorohydrination (the content of dichloropropanol is below 4?wt%). At the optimized conditions, both of the allyl chloride conversion and dichloropropanol selectivity could approach 99% simultaneously and the waste is minimized. What's more, the HTS was reusable. Concentrated HCl solution treatment was adopted to test HTS's stability. The characterization and catalytic evaluation results reveal that, although parts of the framework Ti species have transformed into non-framework Ti and then leached into the solution, HTS remains structural stable, and the allyl chloride conversion and dichloropropanol selectivity didn't decrease obviously during the treatment.