6920-22-5

Basic information

• Product Name: DL-1,2-Hexanediol
• Synonyms: dl-hexane-1,2-diol;DL-1,2-HEXANEDIOL;1,2-HEXANEDIOL;1,2-HEXYLENE GLYCOL;1,2-DIHYDROXYHEXANE;DL-1,2-Hexanediol, 98+%;1,2-HEXANEDIOL, 98.5%;DL-Hexan-1,2-diol
• CAS NO: 6920-22-5
• Molecular Formula: C₆H₁₄O₂
• Molecular Weight: 118.17
• EINECS: 230-029-6
• Product Categories: Organic Building Blocks;Oxygen Compounds;Polyols;Organic solvents
• Mol File: 6920-22-5.mol
• Article Data: 183

Chemical Properties

• Melting Point: 45°C
• Boiling Point: 223-224 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 0.951 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0194mmHg at 25°C
• Refractive Index: n20/D 1.442(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.49±0.20(Predicted)
• Water Solubility: Miscible with water, lower aliphatic hydrocarbons and fatty acids.
• Sensitive: Hygroscopic
• BRN: 1719244
• CAS DataBase Reference: DL-1,2-Hexanediol(CAS DataBase Reference)
• NIST Chemistry Reference: DL-1,2-Hexanediol(6920-22-5)
• EPA Substance Registry System: DL-1,2-Hexanediol(6920-22-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 2
• F: 3
• TSCA: Yes
• Hazardous Substances Data: 6920-22-5(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid.

Uses

Different sources of media describe the Uses of 6920-22-5 differently. You can refer to the following data:
1. DL-1,2-Hexanediol is a solvent used to dissolve other compounds in a formulation.
2. 1,2-Hexanediol can be used in the ruthenium-catalyzed synthesis of oxazolidin-2-ones from urea. It can undergo ruthenium-hydride catalyzed dehydrative coupling with anilines to form substituted indole and quinoline products.

Definition

1,2-Hexanediol is a linear aliphatic diol with a carbon chain length containing six carbons. It is a synthetic preservative and moisture-binding agent belonging to a class of agents known as higher molecular glycols. It is considered non-sensitizing. It is ideal for use as an emollient, humectant, and wetting agent in cosmetic and skin care products.

Preparation

1,2-Hexanediol was prepared in about 45% over-all yield by a-bromination of caproic acid, hydrolysis to a-hydroxycaproic acid, and reduction with lithium aluminum hydride.Using the oxidant of H2O2, the organic acid is oxidized to peroxyacid, and the peroxyacid then epoxidizes the olefin double bond, and finally hydrolyzes to obtain 1,2-hexanediol.

benefits

1,2 hexanediol is most commonly used as a solvent in skincare formulation. It pulls the moisture up from the deeper levels of the skin, as well as from the air, to help keep the top layers of your skin from drying out. This makes It very effective at keeping your skin hydrated and providing long-term moisture. It can also help to disperse pigments more evenly in makeup products and boost the antimicrobial activity of preservatives.

General Description

1,2-Hexanediol acts as cosurfactant, used for modifying the sodium dodecyl sulfate micelles. Solubility of 1,2-hexanediol in supercritical CO2 has been reported. It has a tendency of self-association to form micelle-like aggregates.

Flammability and Explosibility

Nonflammable

Safety

1,2 hexanediol has been proven to be a completely safe and non-irritating ingredient. In an in-use safety evaluation for skin irritation and sensitization potential, 28 participants (males and females) were instructed to use a body wash containing 0.15% 1,2- hexanediol for a minimum of 3 times per week over a 30-day period. There was no evidence of erythema, edema, or dryness of application sites in any of the participants, and it was concluded that the product did not demonstrate a potential for eliciting skin irritation or sensitization.?

Purification Methods

Fractionally distil it, preferably in a vacuum. Alternatively, dissolve it in Et2O, dry with K2CO3 then Na2SO4, filter, evaporate and distil it in a vacuum. The bis-4-nitrobenzoyl derivative has m 101.5-102.5o. [Rudloff Can J Chem 36 486 1958, Beilstein 1 I 251, 1 III 2200, 1 IV 2554.]

InChI:InChI=1/C6H14O2/c1-2-3-4-6(8)5-7/h6-8H,2-5H2,1H3/t6-/m1/s1

Synthetic route

1,2-Epoxyhexane (1436-34-6) → Hexane-1,2-diol (6920-22-5)

Conditions	Yield
With water; erbium(III) triflate In acetonitrile at 25℃; for 1h;	100%
With poly{[CuBa(pyridine-2,5-dicarboxylate)2(H2O)5]*H2O}; dihydrogen peroxide In water; acetonitrile at 40℃; for 2h; Catalytic behavior; Reagent/catalyst;	100%
With water at 40℃; for 8h; Autoclave;	99%

1-hexene (592-41-6) → Hexane-1,2-diol (6920-22-5)

Conditions	Yield
With poly{[CuBa(pyridine-2,5-dicarboxylate)2(H2O)5]*H2O}; dihydrogen peroxide In acetonitrile at 60℃; for 6h; Catalytic behavior; Reagent/catalyst;	100%
With N-methyl-2-indolinone; fluorous OsO4 In water; acetone; tert-butyl alcohol at 20℃; for 36h;	97%
With N-methyl-2-indolinone; polysulfone microencapsulated OsO4 In water; acetone; acetonitrile at 20℃; for 0.416667h;	96%

2-hydroxyhexanoic acid ethyl ester (52089-55-1) → Hexane-1,2-diol (6920-22-5)

Conditions	Yield
With trimethoxysilane; lithium methanolate In tetrahydrofuran for 9.5h; Heating;	100%
With sodium tetrahydroborate at 65℃; for 10h;	65%

2,3-epoxyhexanol (106498-75-3) → Hexane-1,2-diol (6920-22-5)

Conditions	Yield
With Bu3Sn(HMPA)I; tri-n-butyl-tin hydride In tetrahydrofuran at 60℃; for 24h;	100%
With titanium(IV) isopropylate; lithium borohydride In benzene for 2h; Ambient temperature;	80%

4-butyl-1,3-dioxolan-2-one (66675-43-2) → methanol (67-56-1) + Hexane-1,2-diol (6920-22-5)

Conditions	Yield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; hydrogen In tetrahydrofuran at 140℃; for 4h; Autoclave;	A 99 %Chromat. B 99%
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)-amino]ruthenium(II); potassium carbonate In isopropyl alcohol at 140℃; Glovebox;	A > 99 %Chromat. B 97%
With C23H21MnN2O3P(1+)*Br(1-); potassium tert-butylate; hydrogen In 1,4-dioxane at 140℃; under 37503.8 Torr; for 16h; Autoclave;	A 88 %Chromat. B 96%

4-butyl-2,2-dimethyl-[1,3]dioxolane (93339-59-4) → Hexane-1,2-diol (6920-22-5)

Conditions	Yield
With polymer-supported dicyanoketene acetal; water at 20℃; for 2h;	96%
With sulfuric acid

4-butyl-1,3-dioxolan-2-one (66675-43-2) → Hexane-1,2-diol (6920-22-5)

Conditions	Yield
With potassium tert-butylate; hydrogen; C16H18BrCoINO2 In dibutyl ether at 160℃; under 45004.5 Torr; for 20h; Sealed tube; Autoclave;	91%
With water; N,N'-dimethylimidazolium-2-carboxylate at 140℃; under 3000.3 Torr; for 6h; Autoclave; Sealed tube;	64 %Chromat.

S-methyl 2-hydroxyhexanethioate (61603-70-1) → Hexane-1,2-diol (6920-22-5)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 3h; Heating;	90%

1,2-Epoxyhexane (1436-34-6) + carbon dioxide (124-38-9) + aniline (62-53-3) → Hexane-1,2-diol (6920-22-5) + 5-butyl-3-phenyl-1,3-oxazolidin-2-one (1174337-23-5)

Conditions	Yield
With C24H25N4O3(1+)*I(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene at 110℃; under 3750.38 Torr; for 25h; Autoclave;	A n/a B 81%

1-hexene (592-41-6) → 1,2-Epoxyhexane (1436-34-6) + Hexane-1,2-diol (6920-22-5)

Conditions	Yield
With poly{[CuMg(pyridine-2,5-dicarboxylate)2(H2O)4]*2H2O}; dihydrogen peroxide In acetonitrile at 60℃; for 24h; Catalytic behavior;	A 22% B 61%
With dihydrogen peroxide; large pore titanium silicate (MCM-41) In methanol at 55.9℃; for 5h; Product distribution; other hydrocarbon; var. oxidation compounds; var. time;
With urea-hydrogen peroxide; tegafur In methanol at 39.85℃; for 12h; Product distribution; Further Variations:; Reagents;

1-aminohexan-2-ol hydrochloride (92447-04-6) → Hexane-1,2-diol (6920-22-5) + n-hexan-2-one (591-78-6) + 1-acetoxy-2-hexanol (85861-55-8) + 2,5-dibutyl-2-methyl-N-nitroso-oxazolidine (92447-10-4) + 5-butyl-N-nitroso-2-pentyl-oxazolidine (92447-09-1)

Conditions	Yield
With acetic acid; sodium nitrite In water for 48h; Product distribution; pH=6.5; other reagents, other solvent, reagents'molar ratio, different reaction time, other pH value;	A 61% B 17% C 8% D n/a E n/a

methanol (67-56-1) + 4-butyl-1,3-dioxolan-2-one (66675-43-2) → Hexane-1,2-diol (6920-22-5) + carbonic acid dimethyl ester (616-38-6)

Conditions	Yield
With MCM-41-pr-TMEDA(+)Cl(-) at 120℃; for 4h;	A n/a B 55%

4-butyl-1,3-dioxolan-2-one (66675-43-2) + aniline (62-53-3) → Hexane-1,2-diol (6920-22-5) + 5-butyl-3-phenyl-1,3-oxazolidin-2-one (1174337-23-5)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 115℃; for 15h;	A n/a B 51%

1,2-Epoxyhexane (1436-34-6) → Hexane-1,2-diol (6920-22-5) + (S)-1,2-epoxyhexane (1436-34-6, 104898-06-8, 122922-40-1, 130404-08-9)

Conditions	Yield
Stage #1: 1,2-Epoxyhexane With C57H54CoN3O8 In dichloromethane at 20℃; for 0.25h; Stage #2: With water In dichloromethane at 20℃; for 12h; Cooling with ice; enantioselective reaction;	A n/a B 48%
With water In neat (no solvent) at 0 - 20℃; for 6h; Resolution of racemate; enantioselective reaction;	A n/a B 42%

1,2-Epoxyhexane (1436-34-6) → Hexane-1,2-diol (6920-22-5) + (R)-1,2-epoxyhexane (1436-34-6, 122922-40-1, 130404-08-9, 104898-06-8)

Conditions	Yield
With water In neat (no solvent) at 0 - 20℃; for 6h; Reagent/catalyst; Resolution of racemate; enantioselective reaction;	A n/a B 42%

cellulose → propylene glycol (57-55-6) + Hexane-1,2-diol (6920-22-5) + ethylene glycol (107-21-1) + glycerol (56-81-5) + 1,2-dihydroxybutane (584-03-2)

Conditions	Yield
With hydrogen In water at 240℃; for 2h; Autoclave;	A 13.5% B 28.5% C 5.4% D 8% E 10.5%

2-oxohexyl acetate (92675-73-5) → Hexane-1,2-diol (6920-22-5) + Acetic acid (S)-1-hydroxymethyl-pentyl ester + (S)-1-acetoxy-2-hexanol

Conditions	Yield
With baker's yeast In ethanol; water for 6h; Ambient temperature; Yields of byproduct given;	A 28% B n/a C n/a
With baker's yeast; L-Cysteine In ethanol; water for 1h; Ambient temperature; Yield given. Yields of byproduct given;

rac-2-hydroxyhexanoic acid (636-36-2, 6064-63-7) → Hexane-1,2-diol (6920-22-5)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

1-hydroxyhexan-2-one (73397-68-9) → Hexane-1,2-diol (6920-22-5)

Conditions	Yield
Reduktion mit gaerender Hefe;

diethyl ether (60-29-7) + ethyl-2,4-dioxohexanoate (13246-52-1) → Hexane-1,2-diol (6920-22-5)

Conditions	Yield
With lithium aluminium tetrahydride

1-acetoxy-2-chloro-hexane (55704-80-8) → Hexane-1,2-diol (6920-22-5) + 1-amino-2-hydroxy-hexane (72799-62-3, 208850-64-0, 208850-72-0)

Conditions	Yield
With ammonium hydroxide

2,3-epoxyhexanol (106498-75-3) → Hexane-1,2-diol (6920-22-5) + 1,3-hexanediol (21531-91-9)

Conditions	Yield
With lithium borohydride In tetrahydrofuran for 2h; Ambient temperature; Yield given. Yields of byproduct given;

(+/-)-1-(hydroxymethyl)pentyl benzoate (128733-29-9) → Hexane-1,2-diol (6920-22-5)

Conditions	Yield
With barium dihydroxide In ethanol; water at 85℃; for 3h;

1-(hydroxymethyl)pentyl β-D-galactopyranoside (92447-11-5) → D-Galactose (10257-28-0) + Hexane-1,2-diol (6920-22-5)

Conditions	Yield
With water at 100℃; for 1h;	A 91 % Chromat. B n/a

1-hexene (592-41-6) → 1,2-Epoxyhexane (1436-34-6) + n-hexan-2-ol (626-93-7) + Hexane-1,2-diol (6920-22-5) + 1-hexene-3-ol (4798-44-1) + hexanal (66-25-1) + hexan-1-ol (111-27-3)

Conditions	Yield
With europioum(III) chloride; oxygen; propionic acid; zinc In 1,2-dichloro-ethane at 40℃; for 1h; Product distribution; various catalysts, various solvents, other alkenes;

2-(dimethylphenylsilyl)hexanol → Hexane-1,2-diol (6920-22-5)

Conditions	Yield
With peracetic acid; mercury(II) diacetate In acetic anhydride; acetic acid for 3h; Ambient temperature;

2-(Butyl-di-tert-butyl-silanyloxy)-hexan-1-ol (205124-98-7) → Hexane-1,2-diol (6920-22-5)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran Ambient temperature;

diethyl ether (60-29-7) + ethyl-2,4-dioxohexanoate (13246-52-1) + lithium alanate → Hexane-1,2-diol (6920-22-5)

Upstream product

• 52089-55-1 2-hydroxyhexanoic acid ethyl ester 
• 592-41-6 1-hexene 
• 20261-68-1 1-chlorohexan-2-one 
• 110-83-8 cyclohexene 
• 66675-43-2 4-butyl-1,3-dioxolan-2-one 
• 1436-34-6 1,2-Epoxyhexane 
• 41472-84-8 2-hydroxyhexanal 
• 7732-18-5 water 
• 141-78-6 ethyl acetate 
• 60-29-7 diethyl ether 
• 13246-52-1 ethyl-2,4-dioxohexanoate 
• 92675-73-5 2-oxohexyl acetate 
• 61603-70-1 S-methyl 2-hydroxyhexanethioate 
• 92447-04-6 1-aminohexan-2-ol hydrochloride 

Downstream Products

• 128126-11-4 C₂₀H₂₀N₆O₁₂ 
• 128126-11-4 C₂₀H₂₀N₆O₁₂ 
• 143508-41-2 Z-Glu<(2S,2R)-2-hydroxyhexyl>-OtBu 
• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 
• 156599-71-2 (2R,6S,7R,9R,14S)-14-tert-Butyl-2,9-diphenyl-1,8,13,16-tetraoxa-dispiro[5.0.5.4]hexadecane 
• 6920-22-5 (2S)-hexane-1,2-diol 
• 93339-60-7 toluene-4-sulfonic acid (2-hydroxyhexyl) ester 
• 109-52-4 valeric acid 
• 128733-29-9 (+/-)-1-(hydroxymethyl)pentyl benzoate 
• 23246-47-1 (+/-)-2-hydroxyhexyl benzoate 
• 545882-54-0 2-benzyloxymethyl-6-butyl-5,8-dioxa-spiro[3.4]octane 
• 862307-22-0 2-(2-benzyloxy-ethyl)-6-butyl-5,8-dioxa-spiro[3.4]octane 
• 110-62-3 pentanal 
• 638-29-9 n-valeryl chloride 

Relevant articles and documents

Sterically controlling 2-carboxylated imidazolium salts for one-step efficient hydration of epoxides into 1,2-diols

In order to overcome the disadvantages of excessive water and many byproducts in the conventional process of epoxide hydration into 1,2-diols, 2-carboxylated imidazolium salts were first adopted as efficient catalysts for one-step hydration of epoxides into 1,2-diols. By regulating the cation chain lengths, different steric structures of 2-carboxylated imidazolium salts with chain lengths from C1 to C4 were prepared. The salt with the shortest substituent chain (DMIC) exhibited better thermal stability and catalytic performance for hydration, achieving nearly 100% ethylene oxide (EO) conversion and 100% ethylene glycol (EG) selectivity at 120 °C, 0.5 h with just 5 times molar ratio of H2O to EO. Such a tendency is further confirmed and explained by both XPS analysis and DFT calculations. Compared with other salts with longer chains, DMIC has stronger interaction of CO2?anions and imidazolium cations, exhibiting a lower tendency to release CO2?and form HO-CO2?, which can nucleophilically attack and synergistically activate ring-opening of epoxides with imidazolium cations. The strong huge sterically dynamic structure ring-opening transition state slows down the side reaction, and both cations and anions stabilized the transition state imidazolium-EG-HO-CO2?, both of which could avoid excessive hydration into byproducts, explaining the high 1,2-diol yield. Based on this, the cation-anion synergistic mechanism is then proposed.

Diethylene Glycol/NaBr Catalyzed CO2 Insertion into Terminal Epoxides: From Batch to Continuous Flow

CO2 insertion reactions on terminal epoxides (styrene oxide, 1,2-epoxyhexane and butyl glycidyl ether) were performed in a binary homogeneous mixture comprising NaBr as the nucleophilic catalyst and diethylene glycol (DEG) as both solvent and catalyst activator (cation coordinating agent). The reaction protocol was initially studied under batch conditions either in autoclaves and glass reactors: quantitative formation of the cyclic organic carbonate products (COCs) were achieved at T=100 °C and p0(CO2)=1–40 bar. The process was then transferred to continuous-flow (CF) mode. The effects of the reaction parameters (T, p(CO2), catalyst loading, and flow rates) were studied using microfluidic reactors of capacities variable from 7.85 ? 10?2 to 0.157 cm3. Albeit the CF reaction took place at T=220 °C and 120 bar, CF improved the productivity and allowed catalyst recycle through a semi-continuous extraction procedure. For the model case of 1,2-epoxyhexane, the (non-optimized) rate of formation of the corresponding carbonate, 4-butyl-1,3-dioxolan-2-one, was increased up to 27.6 mmol h?1 equiv.?1, a value 2.5 higher than in the batch mode. Moreover, the NaBr/DEG mixture was reusable without loss of performance for at least 4 subsequent CF-tests.

Understanding the mechanism of N coordination on framework Ti of Ti-BEA zeolite and its promoting effect on alkene epoxidation reaction

The function of ammonium salts on the epoxidation performance over Ti-BEA zeolite was investigated in detail. Experiments of alkene epoxidation, side reactions of epoxide and decomposition of H2O2 with or without ammonium salts were designed, and the UV-Vis spectroscopy was employed to analyze the structure of Ti-hydroperoxo species. It is revealed that the ammonia (or amines) dissociated from the ammonium salt would chelate with the linear Ti-η1(OOH) species and form a bridged Ti-η2(OOH)-R species, which is more stable, more weaker in epoxide adsorption and acidity as well. Therefore, side reactions and H2O2 decomposition would be suppressed, and both alkene conversion and epoxide selectivity would be promoted simultaneously. On the other hand, the excessive NH3?H2O (NH3/Ti>1) or NaOH bond with the Ti-η2(OOH)-R species and generate salt-like Ti-η2(OO)-M+ species, resulting in the deactivation of Ti active center. While for ammonium salts, e.g. NH4Cl, the limited dissociation degree along with the acidic environment help the Ti active center to maintain in highly active. In short, this work provides a practical Ti active center tuning method for Ti-BEA zeolite, as well as a thorough understanding of its Ti-hydroperoxo species.