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  • 110-63-4 Structure
  • Basic information

    1. Product Name: 1,4-Butanediol
    2. Synonyms: 1,4-Butyleneglycol;1,4-Dihydroxybutane;1,4-Tetramethylene glycol;DabcoDBO;Diol 14B;NSC 406696;Polycure D;Sucol B;Tetramethylene 1,4-diol;Tetramethylene glycol;Vibracure A 250;ZM 0025;
    3. CAS NO:110-63-4
    4. Molecular Formula: C4H10O2
    5. Molecular Weight: 90.121
    6. EINECS: 203-786-5
    7. Product Categories: N/A
    8. Mol File: 110-63-4.mol
    9. Article Data: 307
  • Chemical Properties

    1. Melting Point: 20℃
    2. Boiling Point: 227.999 °C at 760 mmHg
    3. Flash Point: 105.909 °C
    4. Appearance: viscous colourless liquid
    5. Density: 1.006 g/cm3
    6. Vapor Pressure: 0.015mmHg at 25°C
    7. Refractive Index: 1.441
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 14.73±0.10(Predicted)
    11. Water Solubility: Miscible
    12. CAS DataBase Reference: 1,4-Butanediol(CAS DataBase Reference)
    13. NIST Chemistry Reference: 1,4-Butanediol(110-63-4)
    14. EPA Substance Registry System: 1,4-Butanediol(110-63-4)
  • Safety Data

    1. Hazard Codes:  Xn:Harmful;
    2. Statements: R22:;
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 110-63-4(Hazardous Substances Data)

110-63-4 Usage

Description

1,4-Butanediol (BDO) is an organic compound that falls under the category of glycols. It is a colorless, viscous liquid at standard temperature and pressure, exhibiting solubility in water and many organic solvents. This versatile compound is primarily utilized in the production of polymers and plastics, making it a key component in various industries.

Uses

Used in Polymer and Plastics Industry:
1,4-Butanediol is used as a monomer for the production of polybutylene terephthalate (PBT), a thermoplastic polymer. This polymer is widely used in electronic products due to its desirable properties, such as high strength, heat resistance, and dimensional stability.
Used in Textile Industry:
1,4-Butanediol is used in the production of spandex, a type of elastic fiber. Its incorporation into textiles enhances the stretchability and recovery of the material, making it suitable for applications in clothing, sportswear, and other stretchable fabrics.
Used in Other Polymer Resins:
1,4-Butanediol is also utilized in the formulation of other polymer resins, contributing to the development of materials with specific properties tailored to various applications.

Check Digit Verification of cas no

The CAS Registry Mumber 110-63-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 0 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 110-63:
(5*1)+(4*1)+(3*0)+(2*6)+(1*3)=24
24 % 10 = 4
So 110-63-4 is a valid CAS Registry Number.
InChI:InChI=1/C4H10O2/c5-3-1-2-4-6/h5-6H,1-4H2

110-63-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (L03491)  1,4-Butanediol, 99%   

  • 110-63-4

  • 250g

  • 211.0CNY

  • Detail
  • Alfa Aesar

  • (L03491)  1,4-Butanediol, 99%   

  • 110-63-4

  • 1000g

  • 339.0CNY

  • Detail
  • Alfa Aesar

  • (L03491)  1,4-Butanediol, 99%   

  • 110-63-4

  • 2500g

  • 580.0CNY

  • Detail

110-63-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name butane-1,4-diol

1.2 Other means of identification

Product number -
Other names 1,4-Butanediol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Adhesives and sealant chemicals,CBI,Intermediates
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:110-63-4 SDS

110-63-4Synthetic route

succinic acid diethyl ester
123-25-1

succinic acid diethyl ester

Butane-1,4-diol
110-63-4

Butane-1,4-diol

Conditions
ConditionsYield
With C56H70Cl3N10Ru2(1+)*F6P(1-); potassium tert-butylate; hydrogen In tetrahydrofuran; dodecane at 70℃; under 37503.8 Torr; for 16h; Inert atmosphere; Glovebox; Autoclave;100%
With C30H34Cl2N2P2Ru; potassium methanolate; hydrogen In tetrahydrofuran at 100℃; under 38002.6 - 76005.1 Torr; for 15h; Glovebox; Autoclave;91%
With ethanol; sodium
4-butanolide
96-48-0

4-butanolide

Butane-1,4-diol
110-63-4

Butane-1,4-diol

Conditions
ConditionsYield
With sodium aluminum tetrahydride In tetrahydrofuran at 0℃; for 0.0833333h;100%
With C31H33ClN2O3RuS; potassium tert-butylate; hydrogen In isopropyl alcohol at 60℃; under 37503.8 Torr; for 48h; Inert atmosphere;100%
With C39H39N6ORu(1+)*Br(1-); potassium methanolate; hydrogen In tetrahydrofuran at 100℃; under 37503.8 Torr; for 16h; Reagent/catalyst;100%
succinic acid anhydride
108-30-5

succinic acid anhydride

Butane-1,4-diol
110-63-4

Butane-1,4-diol

Conditions
ConditionsYield
With sodium aluminum tetrahydride In tetrahydrofuran for 24h; Ambient temperature;100%
With hydrogen In water at 155℃; under 165017 Torr; Reagent/catalyst;95%
With sodium tetrahydroborate; C36H30F6N10Ni4O10(2+)*2C2F3O2(1-); zinc(II) chloride In tetrahydrofuran at 45℃; for 12h;78%
With [Ru(1,1,1-tris(diphenylphosphinomethyl)ethane)(trimethylenemethane)]; hydrogen In 1,4-dioxane at 195℃; under 37503.8 Torr; for 24h; Autoclave; Inert atmosphere;
With C38H54Cl2N2P2Ru; hydrogen; sodium hydride In toluene at 160 - 190℃; under 60006 Torr; for 23h; Autoclave; Sealed tube;98 %Spectr.
maleic acid
110-16-7

maleic acid

Butane-1,4-diol
110-63-4

Butane-1,4-diol

Conditions
ConditionsYield
With hydrogen In water100%
With hydrogen In water100%
With hydrogen In water100%
oxirane
75-21-8

oxirane

(naphthalene)Yb(THF)3

(naphthalene)Yb(THF)3

A

naphthalene
91-20-3

naphthalene

B

Butane-1,4-diol
110-63-4

Butane-1,4-diol

C

ytterbium hydroxide

ytterbium hydroxide

Conditions
ConditionsYield
With hydrogen cation In tetrahydrofuran shaken for 10 min at room temp.; centrifuged, decanted, soln. contains naphthalene, pptn. hydrolysed in THF: butanediol detd. by GLC in the organic layer and a pptn. (Yb(OH)3);A 83%
B 100%
C 75%
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

A

Butane-1,4-diol
110-63-4

Butane-1,4-diol

B

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760 Torr; Kinetics;A n/a
B 99%
With LaNi5 hydride In tetrahydrofuran; methanol at 0℃; for 6h;A 10%
B 67%
4-hydroxybutyl (4-oxo-3-phenyl-4H-thiochromen-2-yl)methylcarbonate
1033736-93-4

4-hydroxybutyl (4-oxo-3-phenyl-4H-thiochromen-2-yl)methylcarbonate

A

Butane-1,4-diol
110-63-4

Butane-1,4-diol

B

carbon dioxide
124-38-9

carbon dioxide

C

C16H10O3S
1033736-87-6

C16H10O3S

Conditions
ConditionsYield
In d(4)-methanol at 20℃; for 1h; Conversion of starting material; light irradiation;A 99%
B n/a
C 85%
maleic acid
110-16-7

maleic acid

A

tetrahydrofuran
109-99-9

tetrahydrofuran

B

4-butanolide
96-48-0

4-butanolide

C

Butane-1,4-diol
110-63-4

Butane-1,4-diol

D

succinic acid
110-15-6

succinic acid

E

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With hydrogen; 0.5 percent Pd on Rutile TiO2 at 110℃; Product distribution / selectivity;A 0.37%
B 0.28%
C 0.37%
D 98.89%
E 0.08%
maleic acid
110-16-7

maleic acid

A

tetrahydrofuran
109-99-9

tetrahydrofuran

B

4-butanolide
96-48-0

4-butanolide

C

methanol
67-56-1

methanol

D

Butane-1,4-diol
110-63-4

Butane-1,4-diol

E

malic acid
617-48-1

malic acid

F

succinic acid
110-15-6

succinic acid

G

acetic acid
64-19-7

acetic acid

H

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; 0.5percent Pd on Rutile TiO2 at 110℃; Product distribution / selectivity;A 0.45%
B 0.06%
C 0%
D 0.21%
E 0.36%
F 98.73%
G 0.04%
H 0.08%
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

Butane-1,4-diol
110-63-4

Butane-1,4-diol

Conditions
ConditionsYield
With hydrogen; Ni catalyst as described in example 1 of U.S. Pat. No. 5,068,468 at 140℃; under 150015 Torr; for 336h; Conversion of starting material;98.3%
With hydrogen; Ni catalyst as described in example 1 of U.S. Pat. No. 5,068,468 In water at 140℃; under 150015 Torr; for 24 - 336h; Product distribution / selectivity;98.3%
With hydrogen In water at 100 - 135℃; under 60006 Torr; for 6h; Reagent/catalyst; Temperature; Pressure;90%
maleic acid
110-16-7

maleic acid

A

tetrahydrofuran
109-99-9

tetrahydrofuran

B

4-butanolide
96-48-0

4-butanolide

C

Butane-1,4-diol
110-63-4

Butane-1,4-diol

D

4-hydroxybutanoic acid
591-81-1

4-hydroxybutanoic acid

E

succinic acid
110-15-6

succinic acid

F

acetic acid
64-19-7

acetic acid

G

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; 0.5percent Pd on Rutile TiO2 at 110℃; Product distribution / selectivity;A 0.77%
B 0.38%
C 0.24%
D 0.05%
E 98.28%
F 0.02%
G 0.26%
1,4-Bis-(tert-butyl-dimethyl-silanyloxy)-butane
122795-01-1

1,4-Bis-(tert-butyl-dimethyl-silanyloxy)-butane

Butane-1,4-diol
110-63-4

Butane-1,4-diol

Conditions
ConditionsYield
sulfated SnO2 In methanol at 20℃; for 0.166667h;98%
With sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide at 25℃; for 12h;70%
dimethyl cis-but-2-ene-1,4-dioate
624-48-6

dimethyl cis-but-2-ene-1,4-dioate

A

tetrahydrofuran
109-99-9

tetrahydrofuran

B

2-methoxytetrahydrofuran
13436-45-8

2-methoxytetrahydrofuran

C

4-butanolide
96-48-0

4-butanolide

D

propan-1-ol
71-23-8

propan-1-ol

E

2-(4'-hydroxybutoxy)-tetrahydrofuran
64001-06-5

2-(4'-hydroxybutoxy)-tetrahydrofuran

F

Butane-1,4-diol
110-63-4

Butane-1,4-diol

G

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; copper catalyst, T 4489, Sud-Chemie AG, Munich at 150 - 280℃; under 187519 Torr; Neat liquid(s) and gas(es)/vapour(s);A 1%
B n/a
C 0.4%
D n/a
E n/a
F 98%
G 0.5%
Dimethyl succinate
106-65-0

Dimethyl succinate

Butane-1,4-diol
110-63-4

Butane-1,4-diol

Conditions
ConditionsYield
With C24H38Cl2N3PRu; hydrogen; sodium methylate In isopropyl alcohol at 25℃; under 38002.6 Torr; for 6h; Autoclave;97%
With C13H34BFeNOP2; hydrogen In tetrahydrofuran at 100℃; under 22502.3 Torr; for 18h; Autoclave; Inert atmosphere;97%
With C24H38Cl2N3PRu; hydrogen; sodium methylate In isopropyl alcohol at 25℃; under 37503.8 Torr; for 6h;97%
succinic acid
110-15-6

succinic acid

A

4-butanolide
96-48-0

4-butanolide

B

Butane-1,4-diol
110-63-4

Butane-1,4-diol

Conditions
ConditionsYield
With C36H54IrN2P2(1+)*C24H20B(1-); hydrogen; sodium hydride In toluene at 180℃; under 7500.75 - 45004.5 Torr; for 18h; Reagent/catalyst; Temperature; Pressure; Autoclave; Sealed tube;A 5%
B 95%
Stage #1: succinic acid In 1,4-dioxane at 500℃; for 4h;
Stage #2: With hydrogen In 1,4-dioxane at 200℃; under 60006 Torr; for 5h; Catalytic behavior; Reagent/catalyst;
A n/a
B 64.7%
With hydrogen In water at 130℃; under 37503.8 Torr; for 12h; Pressure; Reagent/catalyst; Temperature; Autoclave;A 34%
B 23%
succinic acid
110-15-6

succinic acid

A

Butane-1,4-diol
110-63-4

Butane-1,4-diol

B

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With perrhenic acid anhydride; hydrogen In 1,4-dioxane at 209.84℃; under 187519 Torr; for 4h; Catalytic behavior; Autoclave; Overall yield = 100 %;A 94%
B 6%
With hydrogen In water at 130℃; under 37503.8 Torr; for 12h; Pressure; Reagent/catalyst; Temperature; Autoclave;A 92%
B 5%
With hydrogen In water at 99.84℃; under 45004.5 Torr;
1-(phenylmethyl)-2,5-pyrrolidinedione
2142-06-5

1-(phenylmethyl)-2,5-pyrrolidinedione

A

Butane-1,4-diol
110-63-4

Butane-1,4-diol

B

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With C25H19BrMnN2O2P; potassium tert-butylate; hydrogen In tetrahydrofuran at 130℃; under 22502.3 Torr; for 48h; Inert atmosphere; Glovebox; Autoclave; Green chemistry;A 85%
B 93%
With [Ru(PtBuNNHtBu)H(CO)Cl]; potassium tert-butylate; hydrogen In 1,4-dioxane at 135℃; under 30003 Torr; for 40h; Autoclave;
1-tert-butyldimethylsilyloxy-4-triethylsilyloxybutane
117785-64-5

1-tert-butyldimethylsilyloxy-4-triethylsilyloxybutane

Butane-1,4-diol
110-63-4

Butane-1,4-diol

Conditions
ConditionsYield
With H-Y zeolite In methanol for 4h; Ambient temperature;92%
2-phenyl-1,3,2-benzodioxaborole
5747-23-9

2-phenyl-1,3,2-benzodioxaborole

A

Butane-1,4-diol
110-63-4

Butane-1,4-diol

B

phenol
108-95-2

phenol

Conditions
ConditionsYield
With oxygen; hydrazine hydrate In acetonitrile at 32℃; under 760.051 Torr; for 4h; Schlenk technique;A 92%
B 90%
maleic acid
110-16-7

maleic acid

A

tetrahydrofuran
109-99-9

tetrahydrofuran

B

4-butanolide
96-48-0

4-butanolide

C

Butane-1,4-diol
110-63-4

Butane-1,4-diol

D

4-hydroxybutanoic acid
591-81-1

4-hydroxybutanoic acid

E

malic acid
617-48-1

malic acid

F

succinic acid
110-15-6

succinic acid

G

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With hydrogen; 0.5percent Pd/2.0percent Re on Rutile TiO2 at 110℃; Product distribution / selectivity;A 1.27%
B 4.78%
C 1.55%
D 1.24%
E 0.48%
F 90.6%
G 0.08%
1-(tert-Butyl-dimethyl-silanyloxy)-4-triisopropylsilanyloxy-butane

1-(tert-Butyl-dimethyl-silanyloxy)-4-triisopropylsilanyloxy-butane

A

Butane-1,4-diol
110-63-4

Butane-1,4-diol

B

4-((triisopropylsilyl)oxy)butan-1-ol
175849-51-1

4-((triisopropylsilyl)oxy)butan-1-ol

Conditions
ConditionsYield
With iron(III) chloride In methanol at 23℃; for 4h;A 4%
B 90%
cis-1,4-anhydroerythritol
4358-64-9

cis-1,4-anhydroerythritol

Butane-1,4-diol
110-63-4

Butane-1,4-diol

Conditions
ConditionsYield
With water; hydrogen In 1,4-dioxane at 139.84℃; under 60006 Torr; for 4h; Reagent/catalyst; Solvent;90%
With cerium(IV) oxide; hydrogen In 1,4-dioxane at 139.84℃; under 60006 Torr; for 24h;
2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

Butane-1,4-diol
110-63-4

Butane-1,4-diol

Conditions
ConditionsYield
With titanium(III)-tris-(tetrahydridoborate) In dichloromethane at -20℃; for 6h;89%
With chloro-trimethyl-silane; Benzyltriethylammonium borohydride; oxygen In dichloromethane at 0℃; for 8h; other enol ethers;73%
With chloro-trimethyl-silane; Benzyltriethylammonium borohydride; oxygen In dichloromethane at 0℃; for 8h;73%
With hydrogen In 1,4-dioxane; water at 139.84℃; under 60006 Torr; for 4h;24%
With water at 5℃;
4-(tetrahydropyran-2-yloxy)butan-1-ol
51326-51-3

4-(tetrahydropyran-2-yloxy)butan-1-ol

Butane-1,4-diol
110-63-4

Butane-1,4-diol

Conditions
ConditionsYield
With ammonium nitrate; Montmorillonite-K10 for 0.0416667h; deprotection; microwave irradiation;89%
With lithium bromide In methanol for 6h; Substitution; Heating;80%
succinic acid
110-15-6

succinic acid

A

tetrahydrofuran
109-99-9

tetrahydrofuran

B

4-butanolide
96-48-0

4-butanolide

C

Butane-1,4-diol
110-63-4

Butane-1,4-diol

D

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen In 1,4-dioxane at 139.84℃; under 60006 Torr; for 96h; Catalytic behavior; Reagent/catalyst; Time; Temperature; Autoclave; Overall yield = 100 %;A 0.2%
B 3.1%
C 89%
D 7.6%
With hydrogen; 1.0percent Pd/ 3.0percent Re on Rutile TiO2 at 164 - 185℃; for 21 - 237h; Product distribution / selectivity;A 2.95%
B 0%
C 81.5%
D 3.35%
With hydrogen; 0percent Pd/5.0percent Re on Rutile TiO2 at 170 - 185℃; for 90 - 825h; Product distribution / selectivity;A 3.38%
B 0%
C 64.14%
D 2.86%
succinic acid
110-15-6

succinic acid

A

tetrahydrofuran
109-99-9

tetrahydrofuran

B

4-butanolide
96-48-0

4-butanolide

C

Butane-1,4-diol
110-63-4

Butane-1,4-diol

D

butyric acid
107-92-6

butyric acid

E

n-butane
106-97-8

n-butane

F

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen In 1,4-dioxane at 139.84℃; under 60006 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Time; Autoclave; Overall yield = > 99 %;A 0.2%
B 3.1%
C 89%
D n/a
E n/a
F 7.6%
maleic acid
110-16-7

maleic acid

A

tetrahydrofuran
109-99-9

tetrahydrofuran

B

4-butanolide
96-48-0

4-butanolide

C

Butane-1,4-diol
110-63-4

Butane-1,4-diol

D

malic acid
617-48-1

malic acid

E

succinic acid
110-15-6

succinic acid

F

acetic acid
64-19-7

acetic acid

G

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; 0.5percent Pd on Rutile TiO2 at 110℃; for 96 - 238h; Product distribution / selectivity;A 0.6%
B 0.04%
C 0.62%
D 0.19%
E 88.49%
F 0.12%
G 0.11%
malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Butane-1,4-diol
110-63-4

Butane-1,4-diol

Conditions
ConditionsYield
With sodium tetrahydroborate; C36H30F6N10Ni4O10(2+)*2C2F3O2(1-); zinc(II) chloride In tetrahydrofuran at 45℃; for 12h;87%
2-butenedioic acid
6915-18-0

2-butenedioic acid

A

Butane-1,4-diol
110-63-4

Butane-1,4-diol

B

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen In water at 130℃; under 37503.8 Torr; for 18h; Pressure; Reagent/catalyst; Autoclave;A 87%
B 13%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

cyclic sulfite of 1,4-butanediol
5732-45-6

cyclic sulfite of 1,4-butanediol

Conditions
ConditionsYield
With methanesulfonic acid; diisopropyl sulfite In toluene at 50℃; under 95 Torr;100%
With pyridine; thionyl chloride In benzene for 4h; Ambient temperature;70%
With thionyl chloride In dichloromethane Heating;67%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

chloroacetaldehyde dimethyl acetal
97-97-2

chloroacetaldehyde dimethyl acetal

2-Chloromethyl-1,3-dioxepane
54237-96-6

2-Chloromethyl-1,3-dioxepane

Conditions
ConditionsYield
With toluene-4-sulfonic acid Heating;100%
With Dowex 50(H+) at 120℃; for 1h;75%
Substitution;38%
With toluene-4-sulfonic acid at 115℃; for 5h;
Butane-1,4-diol
110-63-4

Butane-1,4-diol

(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

Cinnamic acid 1,4-butane diol monoester

Cinnamic acid 1,4-butane diol monoester

Conditions
ConditionsYield
With sulfuric acid In toluene Heating;100%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

1,2 bis (tricosa 10,12 diynoyl)-sn-3-glycerophosphocholine, DC8,9PC
75898-24-7

1,2 bis (tricosa 10,12 diynoyl)-sn-3-glycerophosphocholine, DC8,9PC

DC8,9 phosphatidylhydroxybutanol
150891-85-3

DC8,9 phosphatidylhydroxybutanol

Conditions
ConditionsYield
With acetate buffer In isopropyl alcohol at 37℃; for 10h; phospholipase D;100%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

4-(tert-butyldimethylsiloxy)-1-butanol
87184-99-4

4-(tert-butyldimethylsiloxy)-1-butanol

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0℃; for 1h;100%
Stage #1: Butane-1,4-diol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.666667h; Inert atmosphere;
Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; mineral oil at 0℃; for 1.75h; Inert atmosphere;
100%
Stage #1: Butane-1,4-diol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h;
Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; mineral oil at 0℃; for 1h;
100%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

4-(tret-butyldiphenylsilyloxy)butan-1-ol
130372-07-5

4-(tret-butyldiphenylsilyloxy)butan-1-ol

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 25℃;100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 18℃; for 20h; Inert atmosphere;100%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

N,N-diisopropylcarbamoyl chloride
19009-39-3

N,N-diisopropylcarbamoyl chloride

5-hydroxybutyl N,N-diisopropylcarbamate

5-hydroxybutyl N,N-diisopropylcarbamate

Conditions
ConditionsYield
Stage #1: Butane-1,4-diol With sodium hydride In tetrahydrofuran at 0℃; for 1h;
Stage #2: N,N-diisopropylcarbamoyl chloride In tetrahydrofuran Heating; Further stages.;
100%
Stage #1: Butane-1,4-diol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h;
Stage #2: N,N-diisopropylcarbamoyl chloride In tetrahydrofuran Reflux;
91%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

[(CH3COCHCOCH3)2Al(μ-OCH(CH3)2)2Al(OCH(CH3)2)2]

[(CH3COCHCOCH3)2Al(μ-OCH(CH3)2)2Al(OCH(CH3)2)2]

[Al2(OCH(CH3)2)2(CH3COCHCOCH3)2(O(CH2)4O)]2
163462-32-6

[Al2(OCH(CH3)2)2(CH3COCHCOCH3)2(O(CH2)4O)]2

Conditions
ConditionsYield
In benzene byproducts: i-PrOH; moisture free; refluxing; solvent removal; elem. anal.;100%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

pivaloyl chloride
3282-30-2

pivaloyl chloride

C4H10O2(C5H8O)2

C4H10O2(C5H8O)2

Conditions
ConditionsYield
at 20℃; for 0.25h; Neat (no solvent);100%
vinyl acetate
108-05-4

vinyl acetate

Butane-1,4-diol
110-63-4

Butane-1,4-diol

butane-1,4-diol diacetate
628-67-1

butane-1,4-diol diacetate

Conditions
ConditionsYield
With dilithium tetra(tert-butyl)zincate In toluene at 0℃; for 1h; Inert atmosphere;100%
With steapsin lipase In hexane at 55℃; for 24h; Enzymatic reaction;99 %Chromat.
Butane-1,4-diol
110-63-4

Butane-1,4-diol

4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

4-(p-methoxybenzyloxy)butan-1-ol
119649-45-5

4-(p-methoxybenzyloxy)butan-1-ol

Conditions
ConditionsYield
Stage #1: Butane-1,4-diol With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: 4-methoxy-benzoyl chloride With tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 0 - 20℃; for 17.5h;
100%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

cyclohexanone
108-94-1

cyclohexanone

7,12-dioxaspiro<5.6>dodecane
181-28-2

7,12-dioxaspiro<5.6>dodecane

Conditions
ConditionsYield
With sulfonic group functionalized polyacrylonitrile preoxidated nanofiber mat In cyclohexane at 150℃; for 2h; Dean-Stark;99.7%
With phosphorus modified SO4(2-)/TiO2 In cyclohexane for 2h; Dean-Stark; Reflux;98%
With cyclohexane for 2h; Dean-Stark;92%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

tetrahydrofuran
109-99-9

tetrahydrofuran

Conditions
ConditionsYield
Trichlorbutylstannan at 80 - 84℃; for 9h;99%
Trichlorbutylstannan at 80 - 84℃; for 19h; Mechanism; different molar ratios, different times;99%
zirconium(IV) sulfate at 200℃; under 760.051 Torr; Product distribution / selectivity; Gas phase;99.5%
2-chloroethanal
107-20-0

2-chloroethanal

Butane-1,4-diol
110-63-4

Butane-1,4-diol

2-Chloromethyl-1,3-dioxepane
54237-96-6

2-Chloromethyl-1,3-dioxepane

Conditions
ConditionsYield
With cyclohexane for 4h; Dean-Stark;99%
With sulfonic group functionalized polyacrylonitrile preoxidated nanofiber mat In cyclohexane at 150℃; for 2h; Dean-Stark;99.5%
With phosphorus modified SO4(2-)/TiO2 In cyclohexane for 2h; Dean-Stark; Reflux;98%
With [SOClMIm]Cl at 40℃; for 15h;
With melamine formaldehyde resin supported ionic liquid and cuprous catalyst In cyclohexane for 2h; Dean-Stark; Reflux;80.24 %Chromat.
furfural
98-01-1

furfural

Butane-1,4-diol
110-63-4

Butane-1,4-diol

A

2-methylfuran
534-22-5

2-methylfuran

B

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With hydrogen; Cu-based catalyst at 210℃; Product distribution; Further Variations:; Temperatures; reaction in vapour phase, fixed bed reactor, coupled dehydrogenation reactions of title comp. and INO 160;A 96.5%
B 99.4%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

titanium tetrachloride
7550-45-0

titanium tetrachloride

C8H16O4Ti

C8H16O4Ti

Conditions
ConditionsYield
With calcium hydroxide for 2h; Autoclave; Cooling with ice; Inert atmosphere; Green chemistry;99.3%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

benzyl bromide
100-39-0

benzyl bromide

4-benzyloxy-butan-1-ol
4541-14-4

4-benzyloxy-butan-1-ol

Conditions
ConditionsYield
With potassium hydroxide for 3h; Ambient temperature;99%
With potassium hydroxide at 20℃; Inert atmosphere;99%
Stage #1: Butane-1,4-diol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.833333h;
Stage #2: benzyl bromide In tetrahydrofuran; mineral oil at 20℃; for 14h;
97%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

benzoyl chloride
98-88-4

benzoyl chloride

4-benzoyloxybutan-1-ol
32651-37-9

4-benzoyloxybutan-1-ol

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine Inert atmosphere;99%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 20℃;92%
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;90%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

4-((triisopropylsilyl)oxy)butan-1-ol
175849-51-1

4-((triisopropylsilyl)oxy)butan-1-ol

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran 1.) room temperature, 45 min, 2.) 0 deg C o room temperature, 30 min;99%
Stage #1: Butane-1,4-diol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.75h; Inert atmosphere;
Stage #2: triisopropylsilyl chloride In tetrahydrofuran Inert atmosphere;
97%
Stage #1: Butane-1,4-diol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Inert atmosphere; Cooling with ice;
Stage #2: triisopropylsilyl chloride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
95.6%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

(S)-2-methylbutyl tosylate
38261-81-3

(S)-2-methylbutyl tosylate

(S)-4-(2-methylbutoxy)butan-1-ol
104773-60-6

(S)-4-(2-methylbutoxy)butan-1-ol

Conditions
ConditionsYield
Stage #1: Butane-1,4-diol With sodium In tetrahydrofuran at 20℃;
Stage #2: (S)-2-methylbutyl tosylate In tetrahydrofuran at 70 - 80℃;
99%
Stage #1: Butane-1,4-diol With sodium In tetrahydrofuran at 20℃;
Stage #2: (S)-2-methylbutyl tosylate In tetrahydrofuran at 70 - 80℃;
78%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

2-methylbutanedioic acid
498-21-5, 636-60-2

2-methylbutanedioic acid

poly(butylene methylsuccinate), Mn 9.7E3 Da, Mw/Mn 1.5; monomer(s): 1,4-butanediol; methylsuccinic acid

poly(butylene methylsuccinate), Mn 9.7E3 Da, Mw/Mn 1.5; monomer(s): 1,4-butanediol; methylsuccinic acid

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) at 35℃; under 0.3 - 3 Torr; for 110h;99%

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110-63-4Relevant articles and documents

Effect of boron content on 1,4-butanediol production by hydrogenation of succinic acid over Re-Ru/BMC (boron-modified mesoporous carbon) catalysts

Kang, Ki Hyuk,Han, Seung Ju,Lee, Jong Won,Kim, Tae Hyeop,Song, In Kyu

, p. 206 - 213 (2016)

A series of Re-Ru bimetallic catalysts supported on mesoporous boron-modified carbon (denoted as Re-Ru/xBMC, x?=?B/C molar ratio) were prepared by a single-step surfactant-templating method and a subsequent incipient wetness impregnation method, and they were used for liquid-phase hydrogenation of succinic acid to 1,4-butandiol (BDO). The effect of boron addition on the catalytic activities and physicochemical properties of Re-Ru/xBMC catalysts was investigated. It was found that the addition of boron into carbon support affected surface area, metal dispersion, and reducibility of rhenium and ruthenium species in the Re-Ru/xBMC catalysts. It was also observed that boron species in carbon framework existed in several different phases such as substituted boron, partial oxidized boron, and boron oxide. In particular, the amount of substituted boron species was closely related to the hydrogen adsorption behavior of Re-Ru/xBMC catalysts. The amount of weak hydrogen-binding sites increased with increasing the amount of substituted boron species of the catalysts. Yield for BDO in the hydrogenation of succinic acid showed a volcano-shaped trend with respect to B/C molar ratio. This result was in good agreement with the amount of weak hydrogen-binding sites of the catalysts. It was revealed that TOFBDO increased with increasing the amount of weak hydrogen-binding sites of Re-Ru/xBMC catalysts. Among the catalysts, Re-Ru/0.04BMC with the largest amount of weak hydrogen-binding sites served as an efficient catalyst in the selective formation of BDO by hydrogenation of succinic acid.

Extremely facile and selective nickel-catalyzed allyl ether cleavage

Taniguchi, Takahiko,Ogasawara, Kunio

, p. 1136 - 1137 (1998)

Child's play! Allyl ethers as protecting groups for hydroxyl functions can be removed readily with a combination of DIBAL and catalytic amounts of [NiCl2(dppp)]. Propene is expelled in this remarkably selective reaction, and a nickel-catalyzed hydroalumination-elimination pathway is proposed. dppp = propane-1,3-diylbis(diphenylphosphane).

-

Enz,W.

, p. 206 - 212 (1961)

-

Comparison of Carbon-13 Nuclear Magnetic Resonance Methods for the Analysis of Multiple Partially Deuteriated Products from Catalytic Reactions: Heptan-1-ol and 2-Methylpropanol

MacDougall, Joanna K.,Simpson, Michael C.,Cole-Hamilton, David J.

, p. 3061 - 3066 (1994)

Products from the hydrocarbonylation of hex-1-ene or prop-2-en-1-ol using H2-CO or D2-CO in EtOH or EtOD have been analysed using 13C NMR techniques.Where there are up to four isotopomers in the products, analysis of β-shifted resonances in the 13C- NMR spectrum can give enough information for quantification of all isotopomers.Using prop-2-en-1-ol, D2-CO and EtOH, the 2-methylpropanol produced is a mixture of 16 different isotopomers.These can be individually quantified by analysis of the 13C- NMR spectrum.In particular, the resonance from the methyl C atom shows β and γ shifts, the latter being different for different types of γ-D atom.These analytical methods are shown to be superior to other possibilities including 1H NMR and mass spectrometry.

High chemo and regioselective formation of alcohols from the hydrocarbonylation of alkenes using cooperative ligand effects

Boogaerts, Ine T.I. F.,White, Daniel F. S.,Cole-Hamilton, David J.

, p. 2194 - 2196 (2010)

The hydrocarbonylation of alkenes, including allyl alcohol, catalysed by rhodium complexes and wide angle bidentate ligands together with PEt 3, gives alcohols as the primary products with high chemo and regio-selectivity.

A new carboxylesterase from Brevibacterium linens IFO 12171 responsible for the conversion of 1,4-butanediol diacrylate to 4-hydroxybutyl acrylate: Purification, characterization, gene cloning, and gene expression in Escherichia coli

Sakai, Yasuyoshi,Ishikawa, Junko,Fukasaka, Shunji,Yurimoto, Hiroya,Mitsui, Ryoji,Yanase, Hideshi,Kato, Nobuo

, p. 688 - 697 (1999)

A carboxylesterase that is responsible for conversion of 1,4-butanediol diacrylate (BDA) to 4-hydroxybutyl acrylate (4HBA) was found in Brevibacterium lines IFO 12171, and purified to homogeneity. The purified enzyme was active toward a variety of diesters of ethylene glycol, 1,4-butanediol, and 1,6-hexanediol. The Km and kcat of the enzyme for BDA were 3.04 mM and 203,000 s-1, respectively. The reaction with the purified enzyme gave 98 mM 4HBA from 100 mM BDA for 60 min. The enzyme gene was cloned from the chromosomal DNA of the bacterium. The open reading frame encoding the enzyme was 1176 bp long, corresponding to a protein of 393 amino acid residues (molecular mass=42,569Da). The deduced amino acid sequence contained the tetra peptide motif sequence, STTK, and the serine residue was confirmed to be the catalytic center of BDA esterase by site-directed mutagenesis for several amino acid residues. The gene was expressed in Escherichia coli under the control of the lac promoter, and the gene product (a fusion protein with 6 amino acid residues from β-galactosidase) showed the same catalytic properties as the enzyme from the parent strain.

A Novel and Unusual Reaction of Enol Ethers with Benzyltriethylammonium Borohydride and Chlorotrimethylsilane

Baskaran, S.,Chidambaram, N.,Narasimhan, N.,Chandrasekaran, S.

, p. 6371 - 6374 (1992)

Benzyltriethylammonium borohydride-chlorotrimethylsilane reagent system has been found to effect a novel and unusual reaction with cyclic and acyclic enol ethers 1 to give exclusively diols and alcohols 2 respectively in high yields, under very mild reaction conditions.

Bimetallic Synergy Effects of Phyllosilicate-Derived NiCu@SiO2 Catalysts for 1,4-Butynediol Direct Hydrogenation to 1,4-Butanediol

Wang, Changzhen,Tian, Yani,Wu, Ruifang,Li, Haitao,Yao, Benzhen,Zhao, Yongxiang,Xiao, Tiancun

, p. 4777 - 4787 (2019)

Hydrogenation of 1,4-butynediol (BYD) to 1,4-butanediol (BDO) is a two-step process, with an initial hydrogenation of BYD to 1,4-butenediol (BED) and the subsequent hydrogenation of BED to BDO. However, the BYD hydrogenation also involves many side reactions originated from the isomerization of BED. In order to inhibit the isomerization pathways, phyllosilicate-derived bimetallic NiCu@SiO2 catalysts have been developed for efficient C≡C/C=C hydrogenation in this work. Due to the formation of phyllosilicate matrix and highly dispersed metal nanoparticles, NiCu@SiO2 showed total BYD conversion with extremely high BDO selectivity compared to a conventional impregnated Ni/SiO2 catalyst. A remarkable result of NiCu@SiO2 catalysts is that a new type of bimetallic catalytic sites responsible for the high hydrogenation activity can be differentiated from the Ni phyllosilicate matrix by the induction of Cu species, and these neighboring bimetallic sites with the help of weak acid phyllosilicate interface, can realize to stabilize the activated BED species (allyl alcohol form) adsorbed on the cooperative active sites, thus to avoid its isomerization to aldehyde form and unexpected C=O hydrogenolysis. Consequently, it enhanced the selectivity to the diol products BDO significantly. Owing to the benign improvement of three center synergy effect, 9Ni1Cu@SiO2 possesses the optimum BYD direct hydrogenation ability with a rarely reported high selectivity of 90.5–94.5 % at 50 °C and 1 MPa.

Modelling proposed intermediates in the hydrocarbonylation of alkenes catalysed by rhodium complexes of PBui3 and PPr i3

Cheliatsidou, Paraskevi,White, Daniel F. S.,Slawin, Alexandra M. Z.,Cole-Hamilton, David J.

, p. 2389 - 2394 (2008)

In ethanol, hydrocarbonylation reactions of alkenes catalysed by triethylphosphine complexes of rhodium give alcohols as the products with low linear selectivity, whilst rhodium complexes of PPri3 or PBui3 give mainly aldehydes, again with low linear selectivity. Modelling the proposed acyl intermediates by studying [Rh(C(O)Me)(CO)m(L)4-m] (L = PPri3 or PBui3) shows that they exist as monophosphine species under the normal reaction conditions. In the absence of CO, [Rh(=C(OH)Me)(CO) L2]+ can also be formed. The implications of these NMR studies for the chemo- and regio-selectivity of the hydrocarbonylation reactions are discussed. The Royal Society of Chemistry.

An unusual reaction of cyclic enol ethers with titanium(III) tetrahydroborate

Ravikumar,Chandrasekaran, Srinivasan

, p. 2973 - 2978 (1997)

Titanium(III) Tetrahydroborate formed in situ from titanium tetrachloride and benzyltriethylammonium tetrahydroborate (1:4) readily reacts with cyclic enol ethers in dichloromethane at -20°C to give the corresponding acyclic diols in high yields after simple aqueous work-up.

New environmentally friendly catalysts containing Pd-interstitial carbon made from Pd-glucose precursors for ultraselective hydrogenations in the liquid phase

Chan, Chun Wong Aaron,Xie, Yaling,Cailuo, Nick,Yu, Kai Man Kerry,Cookson, James,Bishop, Peter,Tsang, Shik Chi

, p. 7971 - 7973 (2011)

We report a novel preparation of a Pd nanocatalyst modified with subsurface C via blending a glucose precursor at the molecular level: the catalyst is demonstrated for the first time to be stereoselective in the hydrogenation of alkynes to cis-alkenes in the liquid phase.

Efficient Pd@MIL-101(Cr) hetero-catalysts for 2-butyne-1,4-diol hydrogenation exhibiting high selectivity

Yin, Dongdong,Li, Chuang,Ren, Hangxing,Shekhah, Osama,Liu, Jinxuan,Liang, Changhai

, p. 1626 - 1633 (2017)

Pd@MIL-101(Cr) hetero-catalysts have been successfully prepared using the metal-organic chemical vapour deposition (MOCVD) approach, by choosing [Pd(η3-C3H5)(η5-C5H5)] as a volatile precursor, and the hydrothermally stable metal-organic framework, MIL-101(Cr) as a support. The prepared Pd@MIL-101(Cr) hetero-catalysts characterized with various analytical techniques, exhibited highly monodispersed immobilized Pd nanoparticles in the MIL-101(Cr) cavities, while retaining the pristine crystallinity and porosity. The intact hybrid Pd@MIL-101(Cr) has been demonstrated to be an efficient catalyst for 2-butyne-1,4-diol hydrogenation with excellent activity, stability and selectivity (2-butene-1,4-diol (>94%)).

Biosynthesis of 1,4-butanediol from erythritol using whole-cell catalysis

Dai, Lu,Tai, Cui,Shen, Yaling,Guo, Yali,Tao, Fei

, p. 1 - 5 (2018)

1,4-Butanediol (BDO) biosynthesis from renewable resources is of increasing interest because of global energy and environmental problems. We have previously demonstrated the production of BDO from erythritol by whole-cell catalysis. Here, the effects of several variables on BDO production were investigated, including cell density, temperature, substrate concentration and pH. It was found that the maximum BDO production was obtained at cell density (OD600) of 30. Low temperature and weak alkaline environment were beneficial for the biotransformation. Regarding substrate concentration, 80?g/L of erythritol was found to be optimum for the bioconversion. Under the optimal conditions, the highest concentration of BDO reached 34.5?mg/L, resulting in 5.8-fold increment after optimization. These results will provide useful guidance for enhancing the bioconversion of erythritol to BDO.

Kinetics and mechanism of tetrahydrofuran synthesis via 1,4-butanediol dehydration in high-temperature water

Hunter, Shawn E.,Ehrenberger, Carolyn E.,Savage, Phillip E.

, p. 6229 - 6239 (2006)

We conducted an experimental investigation into the kinetics and mechanism of tetrahydrofuran synthesis from 1,4-butanediol via dehydration in high-temperature liquid water (HTW) without added catalyst at 200-350 °C. The reaction was reversible, with tetrahydrofuran being produced at an equilibrium yield of 84% (at 200 °C) to 94% (at 350 °C). The addition of CO2 to the reaction mixture increased the reaction rate by a factor of 1.9-2.9, because of the increase in acidity resulting from the formation and dissociation of carbonic acid. This increase was much less than that expected (factor of 37-60) from a previously suggested acid-catalyzed mechanism. This disagreement prompted experiments with added acid (HCl) and base (NaOH) to investigate the influence of pH on the reaction rate. These experiments revealed three distinct regions of pH dependence. At high and low pH, the dehydration rate increased with increasing acidity. At near-neutral pH, however, the rate was essentially insensitive to changes in pH. This behavior is consistent with a mechanism where H2O, in addition to H+, serves as a proton donor. This work indicates that the relatively high native concentration of H+ (large Kw), which has commonly been thought to lead to the occurrence of acid-catalyzed reactions in HTW without added catalyst, does not explain the dehydration of 1,4-butanediol in HTW without catalyst. Rather, H2O serves directly as the proton donor for the reaction.

Liquid-phase catalytic hydrogenation of 2-butyne-1,4-diol to 1,4-butanediol at atmospheric pressure on suspended catalysts

Pyatnitsyna,El'Chaninov

, p. 394 - 397 (2013)

The optimum parameters of hydrogenation of 2-butyne-1,4-diol to 1,4-butanediol on the suspended palladium and Ni-Raney catalysts at atmospheric pressure were found. In selected conditions a yield up to 90% of 1,4-butanediol was reached.

Gasparic,Borecky

, (1962)

Selective Hydrogenation of Cyclic Ester to α,ω-Diol Catalyzed by Cationic Ruthenium Complexes with Trialkylphosphine Ligands

Hara, Yoshinori,Inagaki, Hiroko,Nishimura, Sugio,Wada, Keisuke

, p. 1983 - 1986 (1992)

Cyclic esters like γ-butyrolactone were smoothly hydrogenated in the presence of a series of ruthenium complexes with trialkylphosphine ligands under mild conditions to afford the corresponding α,ω-diols with high selectivity.The ruthenium complexes prepared in the presence of additional NH4PF6 or H3PO4 turned out to have the superior catalytic activity.

Tracking Electrical Fields at the Pt/H2O Interface during Hydrogen Catalysis

Ryu, Jaeyune,Surendranath, Yogesh

, p. AR (2019)

We quantify changes in the magnitude of the interfacial electric field under the conditions of H2/H+ catalysis at a Pt surface. We track the product distribution of a local pH-sensitive, surface-catalyzed nonfaradaic reaction, H2 addition to cis-2-butene-1,4-diol to form n-butanol and 1,4-butanediol, to quantify the concentration of solvated H+ at a Pt surface that is constantly held at the reversible hydrogen electrode potential. By tracking the surface H+ concentration across a wide range of pH and ionic strengths, we directly quantify the magnitude of the electrostatic potential drop at the Pt/solution interface and establish that it increases by 60 mV per unit increase in pH. These results provide direct insight into the electric field environment at the Pt surface and highlight the dramatically amplified field existent under alkaline vs acidic conditions.

Young,Shore

, p. 3497 (1969)

Converging conversion - using promiscuous biocatalysts for the cell-free synthesis of chemicals from heterogeneous biomass

Pick, André,Sieber, Volker,Sutiono, Samuel

, p. 3656 - 3663 (2021)

Production of chemicals from lignocellulosic biomass has been proposed as a suitable replacement to petrochemicals. However, one inherent challenge of biomass utilization is the heterogeneity of the substrate resulting in the presence of mixed sugars after hydrolysis. Fermentation of mixed sugars often leads to poor yield and generation of multiple by-products, thus complicating the subsequent downstream processing. System biocatalysis has thus been developed in recent years to address this challenge. In this work, several novel enzymes with broad substrate promiscuity were identified using a sequence-based discovery approach as suitable biocatalysts in a conversion ofd-xylose andl-arabinose, two major constituents of hemicellulose found in plant biomass. These promiscuous enzymes enabled simultaneous biotransformation ofd-xylose andl-arabinose to yield 1,4-butanediol (BDO) with a maximum production rate of 3 g L?1h?1and a yield of >95%. This model system was further adapted toward the production of α-ketoglutarate (2-KG) from the pentoses using O2as a cosubstrate for cofactor recycling reaching a maximum production rate of 4.2 g L?1h?1and a yield of 99%. To verify the potential applicability of our system, we attempted to scale up the BDO and 2-KG production fromd-xylose andl-arabinose. Simple optimization and reaction engineering allowed us to obtain BDO and 2-KG titers of 18 g L?1and 42 g L?1, with theoretical yields of >75% and >99%, respectively. One of the promiscuous enzymes identified together with auxiliary promiscuous enzymes was also suitable for stereoconvergent synthesis from a mixture ofd-glucose andd-galactose, predominant sugars found in food waste streams and microalgae biomass.

Catalytic hydrogenation of 2-butyne-1,4-diol to 2-butene-1,4-diol at atmospheric pressure in the liquid phase

Pyatnitsyna,El'chaninov,Savost'yanov

, p. 89 - 92 (2006)

Selective hydrogenation of 2-butyne-1,4-diol to 2-butene-1,4-diol on suspended palladium and Raney nickel catalysts at atmospheric pressure was studied. The optimal parameters of this reaction were determined. Samples containing 90% 2-butene-1,4-diol were

Hydroboration Reaction and Mechanism of Carboxylic Acids using NaNH2(BH3)2, a Hydroboration Reagent with Reducing Capability between NaBH4and LiAlH4

Wang, Jin,Ju, Ming-Yue,Wang, Xinghua,Ma, Yan-Na,Wei, Donghui,Chen, Xuenian

, p. 5305 - 5316 (2021/04/12)

Hydroboration reactions of carboxylic acids using sodium aminodiboranate (NaNH2[BH3]2, NaADBH) to form primary alcohols were systematically investigated, and the reduction mechanism was elucidated experimentally and computationally. The transfer of hydride ions from B atoms to C atoms, the key step in the mechanism, was theoretically illustrated and supported by experimental results. The intermediates of NH2B2H5, PhCH= CHCOOBH2NH2BH3-, PhCH= CHCH2OBO, and the byproducts of BH4-, NH2BH2, and NH2BH3- were identified and characterized by 11B and 1H NMR. The reducing capacity of NaADBH was found between that of NaBH4 and LiAlH4. We have thus found that NaADBH is a promising reducing agent for hydroboration because of its stability and easy handling. These reactions exhibit excellent yields and good selectivity, therefore providing alternative synthetic approaches for the conversion of carboxylic acids to primary alcohols with a wide range of functional group tolerance.

Method for producing a shaped catalyst body

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Page/Page column 29-30, (2021/11/19)

Provided herein is a novel process for producing shaped catalyst bodies in which a mixture having aluminum contents of Al±0 in the range from 80 to 99.8% by weight, based on the mixture used, is used to form a specific intermetallic phase, shaped catalyst bodies obtainable by the process of the invention, a process for producing an active catalyst fixed bed including the shaped catalyst bodies provided herein, the active catalyst fixed beds and also the use of these active catalyst fixed beds for the hydrogenation of organic hydrogenatable compounds or for formate degradation.

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