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629-11-8

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629-11-8 Usage

Description

1,6-Hexanediol is a waxy hygroscopic solid compound that is white in colour. The compound is a linear diol that contains two primary hydroxyl groups that are located at the terminal. 1,6-Hexanediol’s linear hydrocarbon chain enables the compound to have enhanced hardness and flexibility of polyesters. Moreover, this property is utilized in the extending chains in polyurethanes.

Preparation

1,6-Hexanediol is produced by a propriety process that is based on BASF technology. Industrially, it is prepared by the hydrogenation of adipic acid. Conversely, in the laboratory, 1,6-Hexanediol can be synthesized by the reduction of adipic acid with lithium aluminum hydride.

Uses and Applications

Polyurethanes 1,6-Hexanediol is widely utilized in the manufacture of polyesterols such as sebacates, azelates, and adipates. These compounds are resistant to hydrolysis and have low glass transition temperature as well as high mechanical levels. 1,6-hexanediol is used as an ingredient in the preparation of a wide range of tailor-made products for numerous specialty and standard applications. In Acrylics 1,6-hexanediol is utilized as an ingredient in the manufacture of the bifunctional hexanediol diacrylate which is a monomer that is normally used in conjunction with other acrylic monomers as a reactive diluent for decorative coatings and printing inks. In Adhesives Urethanes and co-terephthalates that are based on 1,6-hexanediol provide faster better tack properties and crystallization. Due to its low glass transition property, 1,6-hexanediol offers high flexibility as well as excellent adhesive properties. Other Uses 1,6-hexanediol is incorporated into the production of other compounds used in polymeric thickeners, sizing agents, plasticizers for polyvinyl chloride, pesticides, and surfactants dyestuffs as a flexible building block.

Safety

1,6-hexanediol is a no-irritating to the skin. However, it can be irritative to the respiratory tract and mucous membrane. 1,6-hexanediol vapours or dust cause irritation to the eye. Severe eye exposure may cause conjunctivitis, iritis, and diffuse corneal opacity.

Chemical Properties

white waxy flakes

Uses

Different sources of media describe the Uses of 629-11-8 differently. You can refer to the following data:
1. Solvent, intermediate for high polymers (nylon, polyesters), coupling agent, coil coating.
2. 1,6-Hexanediol is used in polymer synthesis such as polyester, polyurethane and nylon. It is used as an intermediate to adhesives, acrylics and dyestuffs. Further, it is employed in gasoline refining and pharmaceutical production.
3. 1,6-Hexanediol can be used for a variety of applications such as:a structure-directing agent for the synthesis of ZSM-5 zeolitea solvent for titanium tetraisopropoxide to form titanium oxide (TiO2) nanocrystalsa phase change material in combination with lauric acid for thermal energy storage applications

Definition

ChEBI: A diol that is hexane substituted by hydroxy groups at positions 1 and 6.

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 243, 1993 DOI: 10.1016/S0040-4039(00)60557-9

Hazard

Toxic by ingestion.

Purification Methods

Fractionally crystallise it from its melt or from water. Distil it in vacuo. [Beilstein 1 IV 2556.]

Check Digit Verification of cas no

The CAS Registry Mumber 629-11-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 9 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 629-11:
(5*6)+(4*2)+(3*9)+(2*1)+(1*1)=68
68 % 10 = 8
So 629-11-8 is a valid CAS Registry Number.

629-11-8 Well-known Company Product Price

  • Brand
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  • CAS number
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  • Alfa Aesar

  • (A12439)  1,6-Hexanediol, 97%   

  • 629-11-8

  • 250g

  • 180.0CNY

  • Detail
  • Alfa Aesar

  • (A12439)  1,6-Hexanediol, 97%   

  • 629-11-8

  • 500g

  • 328.0CNY

  • Detail
  • Alfa Aesar

  • (A12439)  1,6-Hexanediol, 97%   

  • 629-11-8

  • 2500g

  • 1043.0CNY

  • Detail
  • Aldrich

  • (240117)  1,6-Hexanediol  99%

  • 629-11-8

  • 240117-50G

  • 493.74CNY

  • Detail
  • Aldrich

  • (H11807)  1,6-Hexanediol  97%

  • 629-11-8

  • H11807-500G

  • 428.22CNY

  • Detail
  • Aldrich

  • (H11807)  1,6-Hexanediol  97%

  • 629-11-8

  • H11807-1KG

  • 789.75CNY

  • Detail

629-11-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name hexane-1,6-diol

1.2 Other means of identification

Product number -
Other names 1,6-HEXANEDIOL

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates,Paint additives and coating additives not described by other categories
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:629-11-8 SDS

629-11-8Synthetic route

Adipic acid
124-04-9

Adipic acid

1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With hydrogen In water at 160℃; under 22502.3 Torr; for 18h; Molecular sieve; chemoselective reaction;100%
With hydrogen In water at 130℃; under 37503.8 Torr; for 18h; Pressure; Reagent/catalyst; Autoclave;89%
With hydrogen In water at 120℃; under 35409.9 Torr; for 2.5h; Reagent/catalyst; Pressure; Temperature;88%
hexanedioic acid dimethyl ester
627-93-0

hexanedioic acid dimethyl ester

1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With ethanol; [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amine](borohydride)(carbonyl)(hydride)iron(II) at 100℃; for 24h; Inert atmosphere; Sealed tube; Darkness;99%
With water; hydrogen under 37503.8 Torr;95%
With hydrogen; copper-comprising catalyst at 195 - 210℃; under 45004.5 Torr; Product distribution / selectivity; Gas phase;90%
hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With C21H35BrMnN2O2P; hydrogen; potassium hydride; 1,3,5-trimethyl-benzene In toluene at 100℃; under 15001.5 Torr; for 36h; Autoclave; Inert atmosphere;98%
With C21H35BrMnN2O2P; hydrogen; potassium hydride In toluene at 100℃; under 15001.5 Torr; for 36h;98%
With trimethoxysilane; lithium methanolate In tetrahydrofuran for 0.5h; Ambient temperature;95%
1-triethylsilyloxy-6-[β-(trimethylsilyl)ethoxymethyloxy]hexane

1-triethylsilyloxy-6-[β-(trimethylsilyl)ethoxymethyloxy]hexane

1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With carbon tetrabromide In methanol for 10h; Heating;98%
6-tert-butoxyhexan-1-ol
91988-83-9

6-tert-butoxyhexan-1-ol

1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With sodium iodide; cerium(III) chloride In acetonitrile at 70℃; for 3h;98%
6-[β-(trimethylsilyl)ethoxymethoxy]hexan-1-ol
279245-42-0

6-[β-(trimethylsilyl)ethoxymethoxy]hexan-1-ol

1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With magnesium bromide In diethyl ether; nitromethane at 20℃; for 5h; Hydrolysis;95%
1-(tert-butyldimethylsilyloxy)-6-[β-(trimethylsilyl)ethoxymethoxy]hexane

1-(tert-butyldimethylsilyloxy)-6-[β-(trimethylsilyl)ethoxymethoxy]hexane

1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With carbon tetrabromide In methanol for 10h; Heating;95%
With zinc dibromide In methanol; dichloromethane for 10h; Hydrolysis;72%
Multi-step reaction with 2 steps
1: 99 percent / TBAF / tetrahydrofuran / 1.5 h / 0 °C
2: 95 percent / MgBr2*Et2O / diethyl ether; nitromethane / 5 h / 20 °C
View Scheme
1-(tert-butyldimethylsilyloxy)-6-(triethylsilyloxy)-hexane
874796-87-9

1-(tert-butyldimethylsilyloxy)-6-(triethylsilyloxy)-hexane

A

1,6-hexanediol
629-11-8

1,6-hexanediol

B

6-(tert-butyldimethylsilyl)oxyhexan-1-ol
103202-59-1

6-(tert-butyldimethylsilyl)oxyhexan-1-ol

Conditions
ConditionsYield
With carbonochloridic acid 1-chloro-ethyl ester In methanol at 20℃; for 0.025h; Product distribution; Further Variations:; Reagents;A 3%
B 95%
2-(5-oxopentyl)-1,3-dioxolane
33875-22-8

2-(5-oxopentyl)-1,3-dioxolane

1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With water; hydrogen at 80 - 180℃; under 15001.5 - 30003 Torr; for 4h; Autoclave; Acidic conditions;95%
N-(6-hydroxyhexyloxy)phthalimide
209973-05-7

N-(6-hydroxyhexyloxy)phthalimide

1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 2h; Heating;93%
hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

A

1,6-hexanediol
629-11-8

1,6-hexanediol

B

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With hydrogen In 1,2-dimethoxyethane at 80℃; under 60006 Torr; for 2h; Reagent/catalyst; Pressure; Solvent; Temperature;A 92.3%
B 8%
With hydrogen; (acetylacetonato)dicarbonylrhodium (l); molybdenum hexacarbonyl In 1,4-dioxane at 150℃; under 75007.5 Torr; for 3h;A 79%
B 7%
1-triethylsilyloxy-6-[β-(trimethylsilyl)ethoxymethyloxy]hexane

1-triethylsilyloxy-6-[β-(trimethylsilyl)ethoxymethyloxy]hexane

A

1,6-hexanediol
629-11-8

1,6-hexanediol

B

6-[β-(trimethylsilyl)ethoxymethoxy]hexan-1-ol
279245-42-0

6-[β-(trimethylsilyl)ethoxymethoxy]hexan-1-ol

Conditions
ConditionsYield
With carbon tetrabromide In methanol for 1.5h; `; ultrasound irradiation;A 3%
B 91%
1-tert-bytyldimethylsilyloxy-6-methoxyethoxymethoxyl-hexane

1-tert-bytyldimethylsilyloxy-6-methoxyethoxymethoxyl-hexane

1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With carbon tetrabromide In methanol for 3h; Heating;90%
1-(tert-butyldiphenylsilyloxy)-6-[β-(trimethylsilyl)ethoxymethoxy]hexane

1-(tert-butyldiphenylsilyloxy)-6-[β-(trimethylsilyl)ethoxymethoxy]hexane

A

1,6-hexanediol
629-11-8

1,6-hexanediol

B

6-{[tert-butyl(diphenyl)silyl]oxy}hexan-1-ol
121671-77-0

6-{[tert-butyl(diphenyl)silyl]oxy}hexan-1-ol

Conditions
ConditionsYield
With carbon tetrabromide In isopropyl alcohol for 1h; Heating;A 3%
B 90%
C21H28O4

C21H28O4

1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With 4,4'-bipyridine; (phthalocyaninato)iron(II); oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 80℃; under 3000.3 Torr; for 8h; Autoclave;90%
6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexan-1-ol
1361022-69-6

6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexan-1-ol

1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With rose bengal; triethylamine In ethanol at 25℃; for 12h; Schlenk technique; Irradiation;90%
hexanedioic acid dimethyl ester
627-93-0

hexanedioic acid dimethyl ester

A

1,6-hexanediol
629-11-8

1,6-hexanediol

B

adipic anhydride
2035-75-8

adipic anhydride

Conditions
ConditionsYield
With water; hydrogen In methanol under 37503.8 Torr;A 8.3%
B 89.1%
1-triisopropylsilyloxy-6-[β-(trimethylsilyl)ethoxymethoxy]hexane

1-triisopropylsilyloxy-6-[β-(trimethylsilyl)ethoxymethoxy]hexane

1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With carbon tetrabromide In methanol for 18h; Heating;89%
1-(tert-butyldiphenylsilyloxy)-6-[β-(trimethylsilyl)ethoxymethoxy]hexane

1-(tert-butyldiphenylsilyloxy)-6-[β-(trimethylsilyl)ethoxymethoxy]hexane

1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With carbon tetrabromide In methanol for 18h; Heating;88%
hexanedinitrile
111-69-3

hexanedinitrile

1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); water; hydrogen In 1,4-dioxane at 140℃; under 7500.75 Torr; for 42h; Autoclave;88%
With formaldehyd; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In water; toluene at 90℃; for 24h;83%
1,6-di(tert-butyldimethylsilyloxy)hexane

1,6-di(tert-butyldimethylsilyloxy)hexane

1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With water; lithium chloride In N,N-dimethyl-formamide at 90℃; for 136h; sealed tube;87%
1-tert-bytyldimethylsilyloxy-6-methoxyethoxymethoxyl-hexane

1-tert-bytyldimethylsilyloxy-6-methoxyethoxymethoxyl-hexane

A

1,6-hexanediol
629-11-8

1,6-hexanediol

B

6-(tert-butyldimethylsilyl)oxyhexan-1-ol
103202-59-1

6-(tert-butyldimethylsilyl)oxyhexan-1-ol

Conditions
ConditionsYield
With carbon tetrabromide In isopropyl alcohol for 3h; Heating;A 86%
B 10%
1-(tert-butyldimethylsilyloxy)-6-[β-(trimethylsilyl)ethoxymethoxy]hexane

1-(tert-butyldimethylsilyloxy)-6-[β-(trimethylsilyl)ethoxymethoxy]hexane

A

1,6-hexanediol
629-11-8

1,6-hexanediol

B

6-[β-(trimethylsilyl)ethoxymethoxy]hexan-1-ol
279245-42-0

6-[β-(trimethylsilyl)ethoxymethoxy]hexan-1-ol

Conditions
ConditionsYield
With carbon tetrabromide In methanol for 1.5h; `; ultrasound irradiation;A 6%
B 86%
1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
In water at 120℃; under 7500.75 - 60006 Torr; for 20h; Product distribution / selectivity; Autoclave;86%
Multi-step reaction with 3 steps
1: hydrogen / water / 21 h / 80 °C / 7500.75 - 60006 Torr / Autoclave
2: trifluorormethanesulfonic acid / sulfolane / 0.5 h / 125 °C
3: hydrogen / water / 4.5 h / 180 °C / 7500.75 - 60006 Torr / Autoclave
View Scheme
Multi-step reaction with 3 steps
1: hydrogen / water / 21 h / 120 °C / 7500.75 - 60006 Torr / Autoclave
2: trifluorormethanesulfonic acid / sulfolane / 0.5 h / 125 °C
3: hydrogen / water / 4.5 h / 180 °C / 7500.75 - 60006 Torr / Autoclave
View Scheme
Bis(trimethylsilyl) adipate
18105-31-2

Bis(trimethylsilyl) adipate

1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With diisobutylaluminium hydride In hexane at -78℃; for 1h;85%
1-iodopropan-3-ol
627-32-7

1-iodopropan-3-ol

4-bromo-1-tosylpiperidine
347885-68-1

4-bromo-1-tosylpiperidine

A

1-tosyl-1,2,5,6-tetrahydropyridine
57186-75-1

1-tosyl-1,2,5,6-tetrahydropyridine

B

1,6-hexanediol
629-11-8

1,6-hexanediol

C

N-tosylpiperidine
4703-22-4

N-tosylpiperidine

D

3-(1-tosylpiperidin-4-yl)propan-1-ol
1282036-62-7

3-(1-tosylpiperidin-4-yl)propan-1-ol

E

1,1'-bis-(toluene-4-sulfonyl)-dodecahydro-[4,4']bipyridyl

1,1'-bis-(toluene-4-sulfonyl)-dodecahydro-[4,4']bipyridyl

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel(0); zinc; 2,6-bis[(4S,6S)-sec-butyl-2-oxazolin-2-yl]pyridine In N,N-dimethyl acetamide at 25℃; for 12h; Inert atmosphere;A 8 %Spectr.
B 85%
C 10 %Spectr.
D 17 %Spectr.
E 52%
1-triisopropylsilyloxy-6-[β-(trimethylsilyl)ethoxymethoxy]hexane

1-triisopropylsilyloxy-6-[β-(trimethylsilyl)ethoxymethoxy]hexane

A

1,6-hexanediol
629-11-8

1,6-hexanediol

B

6-{[tris(propan-2-yl)silyl]oxy}hexan-1-ol
146952-70-7

6-{[tris(propan-2-yl)silyl]oxy}hexan-1-ol

Conditions
ConditionsYield
With carbon tetrabromide In isopropyl alcohol for 1h; Heating;A 10%
B 84%
adipic acid monomethyl ester
627-91-8

adipic acid monomethyl ester

A

1,6-hexanediol
629-11-8

1,6-hexanediol

B

methyl 6-hydroxycaproate
4547-43-7

methyl 6-hydroxycaproate

Conditions
ConditionsYield
With water; Rh6(CO)16*Mo(CO)6 In 1,2-dimethoxyethane at 165℃; under 76000 Torr; for 16h;A 15%
B 83%
1-(tert-butyldimethylsilyloxy)-6-(triisopropylsilyloxy)hexane

1-(tert-butyldimethylsilyloxy)-6-(triisopropylsilyloxy)hexane

A

1,6-hexanediol
629-11-8

1,6-hexanediol

B

6-{[tris(propan-2-yl)silyl]oxy}hexan-1-ol
146952-70-7

6-{[tris(propan-2-yl)silyl]oxy}hexan-1-ol

Conditions
ConditionsYield
With sodium tetrachloroaurate(III) dihydrate In methanol at 20℃; for 2h;A 7%
B 83%
methyl 6-hydroxycaproate
4547-43-7

methyl 6-hydroxycaproate

1,6-hexanediol
629-11-8

1,6-hexanediol

Conditions
ConditionsYield
Stage #1: methyl 6-hydroxycaproate With phenylsilane; fac-[Mn-(xantphos)(CO)3Br] at 120℃; for 12h; Inert atmosphere;
Stage #2: With water; sodium hydroxide In methanol at 20℃; Inert atmosphere;
81%
With trimethoxysilane; lithium methanolate In tetrahydrofuran for 27h; Heating;63%
1,6-hexanediol
629-11-8

1,6-hexanediol

Adipic acid
124-04-9

Adipic acid

Conditions
ConditionsYield
With dihydrogen peroxide; Na12[WZn3(H2O)2(ZnW9O34)2] at 75℃; for 7h;100%
With C24H33IrN4O3; water; sodium hydroxide for 18h; Reflux;97%
With Gluconobacter oxydans DSM 50049 In aq. phosphate buffer at 30℃; pH=4.3-7; Microbiological reaction;95.5%
1,6-hexanediol
629-11-8

1,6-hexanediol

5-(dimethylamino)naphth-1-ylsulfonyl chloride
605-65-2

5-(dimethylamino)naphth-1-ylsulfonyl chloride

(6-hydroxyhex-1-yl) 5-(dimethylamino)naphthalene-1-sulfonate
1034293-27-0

(6-hydroxyhex-1-yl) 5-(dimethylamino)naphthalene-1-sulfonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃;100%
1,6-hexanediol
629-11-8

1,6-hexanediol

oxepane
592-90-5

oxepane

Conditions
ConditionsYield
With copper(ll) bromide In tetrahydrofuran at 190℃; for 12h; Inert atmosphere; Sealed tube;99%
Nafion-H at 135℃; for 5h;72%
With aluminium phosphate aluminium oxide catalyst Heating;60%
1,6-hexanediol
629-11-8

1,6-hexanediol

hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; [RhCl2(p-cymene)]2; potassium carbonate In 4-methyl-2-pentanone for 0.5h; Inert atmosphere; Reflux;99%
With sodium bromite In water; acetic acid for 10h; Ambient temperature;84%
With barium manganate In acetonitrile at 150℃; for 1h; Microwave irradiation;84%
1,6-hexanediol
629-11-8

1,6-hexanediol

isocyanatoethene
3555-94-0

isocyanatoethene

1,6-hexanediol bis(N-vinylcarbamate)
7439-17-0

1,6-hexanediol bis(N-vinylcarbamate)

Conditions
ConditionsYield
Stage #1: 1,6-hexanediol With dibutyltin dilaurate In tetrahydrofuran at 2.5 - 20℃; Inert atmosphere;
Stage #2: isocyanatoethene In tetrahydrofuran at 0 - 20℃; for 26h; Inert atmosphere;
99%
With pyridine In tetrahydrofuran
1,6-hexanediol
629-11-8

1,6-hexanediol

methyl octanate
111-11-5

methyl octanate

1,6-bis-octanoyloxy-hexane
15805-95-5

1,6-bis-octanoyloxy-hexane

Conditions
ConditionsYield
1-Hydroxy-3-(isothiocyanato)-tetrabutyldistannoxane In toluene for 10h; Heating;99%
1,6-hexanediol
629-11-8

1,6-hexanediol

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

6-{[tris(propan-2-yl)silyl]oxy}hexan-1-ol
146952-70-7

6-{[tris(propan-2-yl)silyl]oxy}hexan-1-ol

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 10 - 20℃; for 18h;99%
With 1H-imidazole; dmap In dichloromethane at 20℃; for 4h; Inert atmosphere;93%
With dmap; triethylamine In dichloromethane at 20℃;71%
maleic anhydride
108-31-6

maleic anhydride

1,6-hexanediol
629-11-8

1,6-hexanediol

(Z)-2-Butenedioic-acid-1,6-hexanediyl-ester
86367-74-0

(Z)-2-Butenedioic-acid-1,6-hexanediyl-ester

Conditions
ConditionsYield
In toluene at 60℃;99%
In toluene at 60℃;99%
1,6-hexanediol
629-11-8

1,6-hexanediol

[Ti(N-phenylsalicylideneimine(-H))2(O-i-Pr)2]

[Ti(N-phenylsalicylideneimine(-H))2(O-i-Pr)2]

[Ti(N-phenylsalicylideneimine(-H))2(O(CH2)6O)]
943433-29-2

[Ti(N-phenylsalicylideneimine(-H))2(O(CH2)6O)]

Conditions
ConditionsYield
In benzene byproducts: (CH3)2CHOH; under unhydrous atm., soln. of ligand added to soln. of Ti compd. (3.06:3.01), refluxed, monitored by isopropanol liberated; concd., crystd., elem. anal.;99%
1,6-hexanediol
629-11-8

1,6-hexanediol

cyclohexanone
108-94-1

cyclohexanone

hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

Conditions
ConditionsYield
With wild-type cyclohexanone monooxygenase; Thermoanaerobacter ethanolicus In aq. buffer at 30℃; for 48h; Catalytic behavior; Reagent/catalyst; Baeyer-Villiger Ketone Oxidation; Enzymatic reaction;99%
1,6-hexanediol
629-11-8

1,6-hexanediol

2-(2-methacryloyloxyethyloxy)ethyl isocyanate
107023-60-9

2-(2-methacryloyloxyethyloxy)ethyl isocyanate

C24H40N2O10

C24H40N2O10

Conditions
ConditionsYield
With dibutyltin(II) dilaurate In N,N-dimethyl-formamide at 20℃; for 3h;99%
1,6-hexanediol
629-11-8

1,6-hexanediol

6-chloro-1-hexanol
2009-83-8

6-chloro-1-hexanol

Conditions
ConditionsYield
With tetrachloromethane; hexacarbonyl molybdenum at 120℃; for 8h;98%
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide at -5 - 0℃; for 2h; Solvent; Temperature; Large scale;95.2%
With hydrogenchloride; copper(l) chloride In toluene at 100℃; for 24h;66%
1,6-hexanediol
629-11-8

1,6-hexanediol

1-bromo-6-hexanol
4286-55-9

1-bromo-6-hexanol

Conditions
ConditionsYield
With hydrogen bromide In water; toluene for 2h; Heating / reflux;98%
With hydrogen bromide In water; toluene at 120℃; for 72h;98%
With hydrogen bromide In benzene Heating;97%
1,6-hexanediol
629-11-8

1,6-hexanediol

1,6-dichlorohexane
2163-00-0

1,6-dichlorohexane

Conditions
ConditionsYield
Stage #1: 1,6-hexanediol With N,N-dimethylthiourea In dichloromethane at 20℃;
Stage #2: With N-chloro-succinimide In dichloromethane at 20℃; for 1h; Irradiation;
98%
With hydrogenchloride; ammonium chloride In water at 50 - 110℃; for 3h; Reagent/catalyst;96%
With thionyl chloride; Triphenylphosphine oxide at 20 - 80℃; for 3h;87%
1,6-hexanediol
629-11-8

1,6-hexanediol

4'-Chloro-2,2':6',2''-terpyridine
128143-89-5

4'-Chloro-2,2':6',2''-terpyridine

1,6-bis(2,2':6',2''-terpyridin-4'-yloxy)hexane

1,6-bis(2,2':6',2''-terpyridin-4'-yloxy)hexane

Conditions
ConditionsYield
Stage #1: 1,6-hexanediol With potassium hydroxide In dimethyl sulfoxide at 80℃; for 0.5h;
Stage #2: 4'-Chloro-2,2':6',2''-terpyridine In dimethyl sulfoxide at 60℃; for 4h;
98%
With potassium hydroxide In dimethyl sulfoxide at 70℃; for 4h;66%
Stage #1: 1,6-hexanediol With potassium hydroxide In dimethyl sulfoxide at 70℃; for 0.5h;
Stage #2: 4'-Chloro-2,2':6',2''-terpyridine In dimethyl sulfoxide at 70℃; for 4h;
66%
1,6-hexanediol
629-11-8

1,6-hexanediol

succinic acid
110-15-6

succinic acid

poly(hexamethylene succinate), degree of polymerization > 200, Mn=2.24E4, Mw=3.87E4; monomers: succinic acid; 1,6-hexanediol

poly(hexamethylene succinate), degree of polymerization > 200, Mn=2.24E4, Mw=3.87E4; monomers: succinic acid; 1,6-hexanediol

Conditions
ConditionsYield
tetrachlorobis(tetrahydrofuran)hafnium(IV) In o-xylene for 24h; Heating;98%
1,6-hexanediol
629-11-8

1,6-hexanediol

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

polymer, MP: 248-258 deg C; monomer(s): 1,6-hexanediol; hexaethylphosphorous triamide

polymer, MP: 248-258 deg C; monomer(s): 1,6-hexanediol; hexaethylphosphorous triamide

Conditions
ConditionsYield
In diethylene glycol dimethyl ether at 100 - 110℃; for 25h;98%
1,6-hexanediol
629-11-8

1,6-hexanediol

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

polymer, MP: 274-280 deg C; monomer(s): 1,6-hexanediol; hexaethylphosphorous triamide

polymer, MP: 274-280 deg C; monomer(s): 1,6-hexanediol; hexaethylphosphorous triamide

Conditions
ConditionsYield
at 80 - 90℃; for 3h;98%
1,6-hexanediol
629-11-8

1,6-hexanediol

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

poly(phosphoramidite)? MP: 274-280 deg C; Monomer(s): 1,6-hexanediol; hexaethylphosphorous triamide

poly(phosphoramidite)? MP: 274-280 deg C; Monomer(s): 1,6-hexanediol; hexaethylphosphorous triamide

Conditions
ConditionsYield
at 80 - 90℃; for 3h;98%
1,6-hexanediol
629-11-8

1,6-hexanediol

succinic acid
110-15-6

succinic acid

Reaxys ID: 11364960

Reaxys ID: 11364960

Conditions
ConditionsYield
With molecular sevies 4A; tetrachlorobis(tetrahydrofuran)hafnium(IV) In o-xylene for 24h; Heating / reflux;98%
1,6-hexanediol
629-11-8

1,6-hexanediol

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

hexane-1,6-diyl dimethyl dicarbonate
6222-20-4

hexane-1,6-diyl dimethyl dicarbonate

Conditions
ConditionsYield
With dicobalt octacarbonyl at 180℃; for 1h;98%
With 1,1,1-trioctyl-1-methylphosphonium methylcarbonate at 90℃; for 4h;78%
1,6-hexanediol
629-11-8

1,6-hexanediol

1 ,6-dibromohexane
629-03-8

1 ,6-dibromohexane

Conditions
ConditionsYield
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at -78 - 20℃; for 12h; Darkness; chemoselective reaction;97%
With sulfuric acid; hydrogen bromide
With hydrogen bromide folgendes Erhitzen;
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

1,6-hexanediol
629-11-8

1,6-hexanediol

6-(tetrahydro-2H-pyranyloxy)hexan-1-ol
28659-22-5

6-(tetrahydro-2H-pyranyloxy)hexan-1-ol

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium hydrogen sulfate In hexane microwave irradiation;97%
With lanthanum(III) nitrate at 20℃; for 3h;96%
With sodium hydrogen sulfate In toluene at 20℃; for 5h;94%
1,6-hexanediol
629-11-8

1,6-hexanediol

hexamethylene imine
111-49-9

hexamethylene imine

Conditions
ConditionsYield
With ammonia; hydrogen; CuO/ZnO/Al2O3 In tert-butyl alcohol at 230℃; under 26252.1 Torr;97%
1,6-hexanediol
629-11-8

1,6-hexanediol

Hexamethylphosphorous triamide
1608-26-0

Hexamethylphosphorous triamide

polymer, Mr 5500, MP: 260-275 deg C; monomer(s): 1,6-hexanediol; hexamethylphosphorous triamide

polymer, Mr 5500, MP: 260-275 deg C; monomer(s): 1,6-hexanediol; hexamethylphosphorous triamide

Conditions
ConditionsYield
In diethylene glycol dimethyl ether at 80 - 90℃; for 4h;97%

629-11-8Relevant articles and documents

Determining Roles of Cu0 in the Chemosynthesis of Diols via Condensed Diester Hydrogenation on Cu/SiO2 Catalyst

Wang, Weichao,Wang, Hui,Zhang, Jingwei,Kong, Lingxin,Huang, Huijiang,Liu, Wei,Wang, Shengping,Ma, Xinbin,Zhao, Yujun

, p. 3849 - 3852 (2020)

Copper-based catalyst was applied in the condensed diester hydrogenation with unexpected high selectivity (~100 percent) to 1,6-hexanediol. On basis of the mass transfer analysis and kinetics results, the reaction rate of the condensed diester hydrogenation was deduced to be controlled by the activation of hydrogen on Cu0 sites, which was further demonstrated by the correlations between the catalytic activity and different copper species. Importantly, this catalysis mechanism is different with that of gas-phase diester hydrogenation, which is generally determined by the adsorption of ester on Cu+ species.

-

Raphael,Roxburgh

, p. 3875 (1952)

-

Synthesis of Supported RhMo and PtMo Bimetallic Catalysts by Controlled Surface Reactions

Alba-Rubio, Ana C.,Sener, Canan,Hakim, Sikander H.,Gostanian, Thomas M.,Dumesic, James A.

, p. 3881 - 3886 (2015)

We previously described a synthesis method to prepare bimetallic catalysts with narrow nanoparticle size and composition distributions by means of controlled surface reactions (CSR) between a reduced supported metal nanoparticle and an organometallic precursor of an oxophilic promoter metal. Herein, we report a comparison of such catalysts with those prepared by traditional incipient wetness impregnation. STEM/EDS analysis indicates that catalysts prepared by CSR exhibit more effective interaction of metals, thereby minimizing the undesirable formation of component-rich nanoparticles and/or monometallic domains. Reaction kinetics studies using these bimetallic catalysts reveal that optimal conversion rates in a selective CO hydrogenolysis reaction (i.e., hydrogenolysis of 2-(hydroxymethyl)tetrahydropyran to 1,6-hexanediol) could be achieved using a lower amount of the oxophilic promoter metal for the catalysts prepared by the CSR approach, as compared to their impregnated counterparts. A superior method for greater results: At the same conversion rate level, catalysts prepared by controlled surface reactions (CSR) requires smaller amount of promoter as compared to those prepared by incipient wetness impregnation (IWI). This increased performance is attributed to the uniform bimetallic composition of the catalysts prepared by CSR.

Reductive depolymerization of polyesters and polycarbonates with hydroboranes by using a lanthanum(iii) tris(amide) catalyst

Berthet, Jean-Claude,Cantat, Thibault,Kobylarski, Marie

supporting information, p. 2830 - 2833 (2022/03/09)

The homogeneous reductive depolymerization of polyesters and polycarbonates with hydroboranes is achieved with the use of an f-metal complex catalyst. These polymeric materials are transformed into their value-added alcohol equivalents. Catalysis proceeds readily, under mild conditions, with La[N(SiMe3)2]3 (1 mol%) and pinacolborane (HBpin) and shows high selectivity towards alcohols and diols, after hydrolysis.

Understanding of the key properties of supported Cu-based catalysts and their influence on ester hydrogenolysis

Aubrecht, Jaroslav,Kikhtyanin, Oleg,Kubi?ka, David,Lhotka, Miloslav,Pospelova, Violetta

, (2021/10/19)

The application of Cr-free Cu-based catalysts in ester hydrogenolysis is a modern environmentally-friendly research approach. The comprehensive study of four supported Cu-based catalysts was performed using 8 wt% of Cu loaded on Al2O3, ZnO, TiO2 and ZrO2 supports by an impregnation method. Using XRD, H2-TPR, BET, pyridine-TPD, CO2-TPD and N2O-RFC methods, the effect of the support on the formation of Cu-nanoparticles was described. Al2O3 was evaluated as the support ensuring the highest nanoparticles dispersion, while Cu nanoparticles in Cu-TiO2 were liable to sintering. The catalysts were tested in dimethyl adipate hydrogenolysis, where the catalyst performance and activity (TOF) were evaluated and Cu-ZrO2 showed the best results. A correlation between the number of acid-base sites and the catalyst selectivity was revealed and the catalyst effect on the formation of various by-products was described. The intrinsic selectivity to hydrogenolysis products was found to decrease with the increasing acid-base character of the supports whereas the selectivity to transesterification and cyclization products increased. The hydrogenolysis activity was not a simple function of the number of the surface copper atoms, but it was affected by the support nature and its properties.

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