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  • 105-08-8 Structure
  • Basic information

    1. Product Name: 1,4-Cyclohexanedimethanol
    2. Synonyms: 1,4-cyclohexamethylenebismethylol;1,4-Cyclohexanedimethanol,c&t;1,4-cyclohexanedimethanol,mixtureofcisandtrans;bis(hydroxymethyl)-1,4cyclohexane;Cyclohexane-1,4-dimethanol;Cyclohexane-1,4-dimethanol,c&t;rikabinoldm;CYCLOHEXANEDIMETHANOL(1,4-)
    3. CAS NO:105-08-8
    4. Molecular Formula: C8H16O2
    5. Molecular Weight: 144.21
    6. EINECS: 203-268-9
    7. Product Categories: Alkohols;fine chemicals
    8. Mol File: 105-08-8.mol
    9. Article Data: 49
  • Chemical Properties

    1. Melting Point: 31.5 °C
    2. Boiling Point: 283 °C(lit.)
    3. Flash Point: 322 °F
    4. Appearance: clear colourless viscous liquid
    5. Density: 1,04 g/cm3
    6. Vapor Density: 5 (vs air)
    7. Vapor Pressure: 0.000303mmHg at 25°C
    8. Refractive Index: 1.4240 (estimate)
    9. Storage Temp.: Store below +30°C.
    10. Solubility: >34g/l soluble
    11. PKA: 14.75±0.10(Predicted)
    12. Water Solubility: MISCIBLE
    13. BRN: 1902271
    14. CAS DataBase Reference: 1,4-Cyclohexanedimethanol(CAS DataBase Reference)
    15. NIST Chemistry Reference: 1,4-Cyclohexanedimethanol(105-08-8)
    16. EPA Substance Registry System: 1,4-Cyclohexanedimethanol(105-08-8)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36-41
    3. Safety Statements: 22-24/25-39-26
    4. WGK Germany: 1
    5. RTECS: GU9800000
    6. TSCA: Yes
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 105-08-8(Hazardous Substances Data)

105-08-8 Usage

Description

1,4-Cyclohexanedimethanol is a white waxy solid or clear colorless viscous liquid after melting, with a melting point of 43°C (cis) and 70°C (trans). It has a sublimation temperature of 160°C and is miscible with water and alcohol, soluble in ketone, and almost insoluble in aliphatic hydrocarbon and ether. It is extensively used as a cross-linking reagent in the polymer industry.

Uses

Used in Polymer Industry:
1,4-Cyclohexanedimethanol is used as a cross-linking reagent for enhancing the properties of various polymers.
Used in Fiber Production:
1,4-Cyclohexanedimethanol is used as a precursor to polyesters, making it an essential component in the production of polyester fibers.
Used in Electrical Appliances:
1,4-Cyclohexanedimethanol is used in the manufacturing of polyester-based electrical appliances due to its properties as a cross-linking reagent.
Used in Unsaturated Polyester Resins:
1,4-Cyclohexanedimethanol is used as a key component in the production of unsaturated polyester resins, which have various applications in the industry.
Used in Polyester Glaze:
1,4-Cyclohexanedimethanol is used in the formulation of polyester glaze, providing desired properties to the final product.
Used in Polyurethane Foam:
1,4-Cyclohexanedimethanol is used in the production of polyurethane foam, a versatile material with various applications.
Used in Lubricant and Hydraulic Fluid Production:
1,4-Cyclohexanedimethanol is used in the manufacturing of lubricants and hydraulic fluids, contributing to their performance characteristics.
Used in Polyethylene Terephthalate (PET) Production:
1,4-Cyclohexanedimethanol is one of the most important co-monomers for the production of polyethylene terephthalate (PET) or polyethylene terephthalic ester (PETE).
Used in Polyketal Copolymers Synthesis:
1,4-Cyclohexanedimethanol has been used in the synthesis of polyketal copolymers, which have potential applications in various industries.
Used in Polyester-Carbonates Synthesis:
1,4-Cyclohexanedimethanol was used as a diol comonomer during the synthesis of polyester-carbonates based on 1,3-propylene-co-1,4-cyclohexanedimethylene succinate, contributing to the development of new polymer materials.

Characteristics

1,4-Cyclohexanedimethanol (CHDM) is both hard and flexible, with high TG, and offers excellent heat stability, good solubility, and good weather resistance. It can enhance the reactivity in polyester compounds, and improve the hydrolytic stability, plasticity, gloss, transparency, printability, and processing ability of the polymer.

Preparation

In the first step, proline-catalyzed formal [3+1+2] cycloaddition of formaldehyde, crotonaldehyde, and ethyl acrylate affords ethyl 4-formylcyclohex-3-enecarboxylate (compound 1) by a domino Mannich condensation and Diels–Alder (D–A) process.synthesis of 1,4-Cyclohexanedimethanol (CHDM) and CHDA from compound 1. Cu-based catalysts have been widely used for the hydrogenation of esters to alcohols. compound 1 can be hydrogenated to CHDM over commercially available Cu/Zn/Al catalyst. Under the optimized reaction conditions (240°C, 4.0 MPa of H2 , 12 h), a high yield (84%) of CHDM was achieved. After taking the optimized yield of compound 1 (91%) into account in the first step, the overall yield of CHDM starting from formaldehyde, crotonaldehyde, and ethyl acrylate, reached 76%.

Check Digit Verification of cas no

The CAS Registry Mumber 105-08-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 5 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 105-08:
(5*1)+(4*0)+(3*5)+(2*0)+(1*8)=28
28 % 10 = 8
So 105-08-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H16O2/c9-5-7-1-2-8(6-10)4-3-7/h7-10H,1-6H2

105-08-8 Well-known Company Product Price

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

  • (A16769)  1,4-Cyclohexanedimethanol, cis + trans, 99%   

  • 105-08-8

  • 100g

  • 223.0CNY

  • Detail
  • Alfa Aesar

  • (A16769)  1,4-Cyclohexanedimethanol, cis + trans, 99%   

  • 105-08-8

  • 500g

  • 405.0CNY

  • Detail
  • Aldrich

  • (125598)  1,4-Cyclohexanedimethanol  mixture of cis and trans, 99%

  • 105-08-8

  • 125598-100G

  • 245.70CNY

  • Detail
  • Aldrich

  • (125598)  1,4-Cyclohexanedimethanol  mixture of cis and trans, 99%

  • 105-08-8

  • 125598-500G

  • 375.57CNY

  • Detail
  • Aldrich

  • (125598)  1,4-Cyclohexanedimethanol  mixture of cis and trans, 99%

  • 105-08-8

  • 125598-3KG

  • 1,385.28CNY

  • Detail
  • Aldrich

  • (125598)  1,4-Cyclohexanedimethanol  mixture of cis and trans, 99%

  • 105-08-8

  • 125598-17KG

  • 3,608.28CNY

  • Detail

105-08-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,4-Cyclohexanedimethanol

1.2 Other means of identification

Product number -
Other names 1,4-Chidm

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. 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:105-08-8 SDS

105-08-8Synthetic route

cyclohexane-1,4-dicarboxylic acid
619-81-8, 619-82-9, 1076-97-7

cyclohexane-1,4-dicarboxylic acid

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With tin; hydrogen at 220℃; under 90009 Torr; for 0.75h; Temperature; Pressure;100%
With hydrogen In water at 230℃; under 15001.5 - 75007.5 Torr; Catalytic behavior; Reagent/catalyst; Autoclave;98.3%
With hydrogen In water at 230℃; under 63756.4 Torr; for 3h; Reagent/catalyst; Autoclave;95.8%
1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With hydrogen In methanol at 200 - 240℃; under 30003 - 60006 Torr; for 8h;92%
With Cat.7; hydrogen at 180 - 250℃; under 52505.3 - 67506.8 Torr; Reagent/catalyst; Temperature; Pressure;
p-xylylene glycol
589-29-7

p-xylylene glycol

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With Ru/Al2O3; hydrogen In tetrahydrofuran at 60℃; under 7.50075 Torr; for 3.5h; Pressure; Autoclave;92%
Bis(2-Hydroxyethyl)terephthalat
959-26-2

Bis(2-Hydroxyethyl)terephthalat

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
Stage #1: Bis(2-Hydroxyethyl)terephthalat With tin(II) chloride dihdyrate; ruthenium(III) chloride trihydrate; alumina; Cl6H6Pt(2-)*2H(1+)*6H2O; hydrogen In water at 180 - 260℃; under 37503.8 Torr; for 10h; Autoclave;
Stage #2: With sodium tetrahydroborate; sodium hydroxide at 500℃; for 5.5h; pH=9; Reagent/catalyst; Concentration; Temperature;
87.1%
dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With C33H29FeMnN2O3P(1+)*Br(1-); potassium tert-butylate; hydrogen In isopropyl alcohol at 75℃; under 37503.8 Torr; Autoclave;86%
Stage #1: dimethyl 1,4-cyclohexane dicarboxylate With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 0.5h;
Stage #2: With water In tetrahydrofuran
With hydrogen In methanol at 220℃; under 45004.5 Torr; Catalytic behavior; Time; Temperature; Green chemistry;
Bis(2-Hydroxyethyl)terephthalat
959-26-2

Bis(2-Hydroxyethyl)terephthalat

A

4-methylbenzoic acid ethyl ester
94-08-6

4-methylbenzoic acid ethyl ester

B

para-xylene
106-42-3

para-xylene

C

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With hydrogen at 170 - 260℃; under 37503.8 Torr; for 8h; Autoclave;A n/a
B n/a
C 78.4%
bis(2-hydroxyethyl) cyclohexane-1,4-dicarboxylate

bis(2-hydroxyethyl) cyclohexane-1,4-dicarboxylate

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With hydrogen In neat (no solvent) at 269.84℃; under 78757.9 Torr; for 10h; Reagent/catalyst; Pressure; Temperature; Autoclave;78%
ethyl 4-formylcyclohex-3-enecarboxylate

ethyl 4-formylcyclohex-3-enecarboxylate

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With hydrogen In water at 160℃; under 45004.5 Torr; for 12h; Reagent/catalyst;56%
Bis(2-Hydroxyethyl)terephthalat
959-26-2

Bis(2-Hydroxyethyl)terephthalat

A

4-methylbenzoic acid ethyl ester
94-08-6

4-methylbenzoic acid ethyl ester

B

para-xylene
106-42-3

para-xylene

C

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

D

C10H18O3

C10H18O3

E

C10H18O4

C10H18O4

Conditions
ConditionsYield
With hydrogen at 230℃; under 37503.8 Torr; for 8h; Autoclave;A n/a
B n/a
C 47.2%
D n/a
E n/a
Bis(2-Hydroxyethyl)terephthalat
959-26-2

Bis(2-Hydroxyethyl)terephthalat

A

4-methylbenzoic acid ethyl ester
94-08-6

4-methylbenzoic acid ethyl ester

B

para-xylene
106-42-3

para-xylene

C

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

D

(4-methylcyclohexyl)methanol
34885-03-5

(4-methylcyclohexyl)methanol

E

1,4 dimethylcyclohexane
589-90-2

1,4 dimethylcyclohexane

Conditions
ConditionsYield
With hydrogen at 260℃; under 37503.8 Torr; for 8h; Autoclave;A n/a
B n/a
C 28.5%
D n/a
E n/a
Bis(2-Hydroxyethyl)terephthalat
959-26-2

Bis(2-Hydroxyethyl)terephthalat

A

4-methylbenzoic acid ethyl ester
94-08-6

4-methylbenzoic acid ethyl ester

B

para-xylene
106-42-3

para-xylene

C

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

D

C10H18O4

C10H18O4

E

(4-methylcyclohexyl)methanol
34885-03-5

(4-methylcyclohexyl)methanol

F

1,4 dimethylcyclohexane
589-90-2

1,4 dimethylcyclohexane

Conditions
ConditionsYield
With hydrogen at 170 - 260℃; under 37503.8 Torr; for 8h; Autoclave;A n/a
B n/a
C 14.7%
D n/a
E n/a
F n/a
Bis(2-Hydroxyethyl)terephthalat
959-26-2

Bis(2-Hydroxyethyl)terephthalat

A

4-methylbenzoic acid ethyl ester
94-08-6

4-methylbenzoic acid ethyl ester

B

para-xylene
106-42-3

para-xylene

C

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

D

C10H18O4

C10H18O4

Conditions
ConditionsYield
With hydrogen at 170 - 260℃; under 37503.8 Torr; for 8h; Autoclave;A n/a
B n/a
C 5.3%
D n/a
1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

A

dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

B

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

C

4-methyloxymethylhydroxymethylhydroxymethylcyclohexane
62172-89-8

4-methyloxymethylhydroxymethylhydroxymethylcyclohexane

D

bis(4-hydroxymethylcyclohexyl) ether

bis(4-hydroxymethylcyclohexyl) ether

Conditions
ConditionsYield
With hydrogen; Pt1Ru5; silica gel In ethanol at 99.85℃; under 15001.2 Torr; for 8h; Product distribution; Further Variations:; Catalysts; reaction times;
1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

A

dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

B

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With hydrogen; Ru5PtSn; silica gel In ethanol at 99.85℃; under 15001.2 Torr; for 24h;
1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

A

dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

B

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

C

methyl 4-methyl-1-cyclohexanecarboxylate
51181-40-9

methyl 4-methyl-1-cyclohexanecarboxylate

D

(4-methylcyclohexyl)methanol
34885-03-5

(4-methylcyclohexyl)methanol

Conditions
ConditionsYield
With hydrogen; Ru5PtSn; silica gel In ethanol at 119.85℃; under 30002.4 Torr; for 8h; Further byproducts given;
With hydrogen; Ru5PtSn; silica gel In ethanol at 119.85℃; under 15001.2 Torr; for 24h; Further byproducts given;
1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

A

dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

B

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

C

[4-(methoxymethyl)cyclohexyl]methanol
98955-27-2

[4-(methoxymethyl)cyclohexyl]methanol

D

bis(4-hydroxymethylcyclohexyl) ether

bis(4-hydroxymethylcyclohexyl) ether

Conditions
ConditionsYield
With hydrogen; Ru5PtSn; silica gel In ethanol at 99.85℃; under 15001.2 Torr; for 24h; Product distribution; Further Variations:; Catalysts; Temperatures; Pressures;
With hydrogen; Pt1Ru5; silica gel In ethanol at 99.85℃; under 15001.2 Torr; for 24h;
terephthalic acid
100-21-0

terephthalic acid

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 6 h / 260 - 280 °C / 4535.33 Torr
2: dimethyl 1,4-cyclohexane dicarboxylate; Pd/Al2O3; hydrogen / 1 h / 200 °C / 93849.2 Torr / Autoclave
3: (4-methylcyclohexyl)methanol; hydrogen / 5 h / 250 °C / 212036 Torr
View Scheme
Stage #1: terephthalic acid With palladium on activated charcoal; hydrogen In water at 230℃; under 60006 Torr;
Stage #2: at 230℃; Pressure; Temperature; Reagent/catalyst;
100 %Chromat.
With hydrogen In water at 20 - 230℃; under 60006 Torr; Catalytic behavior; Reagent/catalyst; Inert atmosphere;
terephthalic acid 1,4-bis(4-methylcyclohexyl)methyl ester
95623-88-4

terephthalic acid 1,4-bis(4-methylcyclohexyl)methyl ester

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethyl 1,4-cyclohexane dicarboxylate; Pd/Al2O3; hydrogen / 1 h / 200 °C / 93849.2 Torr / Autoclave
2: (4-methylcyclohexyl)methanol; hydrogen / 5 h / 250 °C / 212036 Torr
View Scheme
With hydrogen at 150℃; under 22502.3 Torr; Temperature; Pressure;
bis((4-methylcyclohexyl)methyl) cyclohexane-1,4-dicarboxylate
1420954-46-6

bis((4-methylcyclohexyl)methyl) cyclohexane-1,4-dicarboxylate

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With (4-methylcyclohexyl)methanol; hydrogen at 250℃; under 212036 Torr; for 5h;
dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

A

4-hydroxymethylcyclohexanecarboxylic acid methyl ester
13380-85-3

4-hydroxymethylcyclohexanecarboxylic acid methyl ester

B

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With hydrogen In methanol at 220℃; under 45004.5 Torr; Green chemistry;
With hydrogen In methanol at 219.84℃; under 37503.8 Torr; Reagent/catalyst; chemoselective reaction;
With hydrogen In isopropyl alcohol at 220℃; under 75007.5 Torr; for 10h; Reagent/catalyst; Autoclave;
dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

A

4-hydroxymethylcyclohexanecarboxylic acid methyl ester
13380-85-3

4-hydroxymethylcyclohexanecarboxylic acid methyl ester

B

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

C

(4-methylcyclohexyl)methanol
34885-03-5

(4-methylcyclohexyl)methanol

D

4-(hydroxymethyl)-1-cyclohexanecarboxaldehyde
92385-32-5

4-(hydroxymethyl)-1-cyclohexanecarboxaldehyde

Conditions
ConditionsYield
With hydrogen at 220℃; under 45004.5 Torr; Catalytic behavior; Reagent/catalyst; Time; Overall yield = 98.7 %;
dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

A

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

B

(4-methylcyclohexyl)methanol
34885-03-5

(4-methylcyclohexyl)methanol

C

4-(hydroxymethyl)-1-cyclohexanecarboxaldehyde
92385-32-5

4-(hydroxymethyl)-1-cyclohexanecarboxaldehyde

Conditions
ConditionsYield
With hydrogen at 220℃; under 45004.5 Torr; Catalytic behavior; Reagent/catalyst; Time; Overall yield = 67.4 %;
dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

A

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

B

1,4-cyclohexanedicarboxaldehyde
33424-83-8

1,4-cyclohexanedicarboxaldehyde

Conditions
ConditionsYield
With hydrogen at 180℃; under 30003 Torr; Temperature; Pressure; Concentration;
dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

A

4-hydroxymethylcyclohexanecarboxylic acid methyl ester
13380-85-3

4-hydroxymethylcyclohexanecarboxylic acid methyl ester

B

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

C

(4-methylcyclohexyl)methanol
34885-03-5

(4-methylcyclohexyl)methanol

Conditions
ConditionsYield
With hydrogen In isopropyl alcohol at 220℃; under 75007.5 Torr; for 10h; Reagent/catalyst; Pressure; Autoclave;
dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

A

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

B

(4-methylcyclohexyl)methanol
34885-03-5

(4-methylcyclohexyl)methanol

Conditions
ConditionsYield
With hydrogen In isopropyl alcohol at 220℃; under 75007.5 Torr; for 10h; Reagent/catalyst; Pressure; Autoclave;
L-leucine
61-90-5

L-leucine

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

L,L-leucine 1,4-cyclohexanedimethanol diester
893447-84-2

L,L-leucine 1,4-cyclohexanedimethanol diester

Conditions
ConditionsYield
Stage #1: L-leucine; bis-1,4-(hydroxymethyl)cyclohexane With toluene-4-sulfonic acid In toluene at 150℃; for 30h; Heating / reflux;
Stage #2: With sodium hydrogencarbonate In water; toluene at 60℃;
100%
L-leucine
61-90-5

L-leucine

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

L,L-leucine 1,4-cyclohexanedimethanol diester
893447-84-2

L,L-leucine 1,4-cyclohexanedimethanol diester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 20 - 150℃; for 30h; Heating / reflux;100%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

acetic anhydride
108-24-7

acetic anhydride

1,4-cyclohexanedimethylene diacetate
6308-18-5

1,4-cyclohexanedimethylene diacetate

Conditions
ConditionsYield
With pyridine at 125℃; for 3.5h; Reagent/catalyst; Large scale;99%
With pyridine at 125℃; for 3.5h; Large scale;99%
5-Norbornene-2-carboxaldehyde
5453-80-5, 19926-90-0

5-Norbornene-2-carboxaldehyde

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

5-norbornene-2-(4-hydroxymethyl)cyklohexylmethoxymethanol

5-norbornene-2-(4-hydroxymethyl)cyklohexylmethoxymethanol

Conditions
ConditionsYield
sodium hydride at 20℃; for 10h;93%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

7-oxa-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde
59274-95-2

7-oxa-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde

oxabicyclo[2.2.1]-hept-5-ene-2-(4-hydroxymethyl)cyclohexylmethoxy methanol

oxabicyclo[2.2.1]-hept-5-ene-2-(4-hydroxymethyl)cyclohexylmethoxy methanol

Conditions
ConditionsYield
sodium hydride at 20℃; for 10h;93%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

aniline
62-53-3

aniline

C20H26N2
1352050-49-7

C20H26N2

Conditions
ConditionsYield
With Pt-Sn/γ-Al2O3 In o-xylene at 145℃; for 24h; Inert atmosphere;93%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

cyclohexane-1,4-dimethyl chloride
824-93-1

cyclohexane-1,4-dimethyl chloride

Conditions
ConditionsYield
With pyridine; thionyl chloride Chlorination; Heating;92%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

phenyl chloroformate
1885-14-9

phenyl chloroformate

1,4-cyclohexanedimethanol diphenyl dicarbonate
22563-70-8

1,4-cyclohexanedimethanol diphenyl dicarbonate

Conditions
ConditionsYield
With pyridine; dmap In tetrahydrofuran at 0 - 20℃;90.2%
2-Isocyanatoethyl methacrylate
30674-80-7

2-Isocyanatoethyl methacrylate

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

C15H25NO5

C15H25NO5

Conditions
ConditionsYield
With dibutyltin dilaurate In toluene for 5h;90.1%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

acetyl chloride
75-36-5

acetyl chloride

1,4-cyclohexanedimethylene diacetate
6308-18-5

1,4-cyclohexanedimethylene diacetate

Conditions
ConditionsYield
With pyridine; dmap In chloroform at 0 - 20℃;87%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

(R)-1-C-(1-Cyclohexen-5-yl)carbaldehyde
60631-76-7

(R)-1-C-(1-Cyclohexen-5-yl)carbaldehyde

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

acetal oligomer

acetal oligomer

Conditions
ConditionsYield
With N,N-dimethyl acetamide; toluene-4-sulfonic acid at 140℃; for 20h;85%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

chlorophosphoric acid diphenyl ester
2524-64-3

chlorophosphoric acid diphenyl ester

1,4-cyclohexanedimethanol bis(diphenyl phosphate)
476371-27-4

1,4-cyclohexanedimethanol bis(diphenyl phosphate)

Conditions
ConditionsYield
With magnesium chloride In methanol; hexane82.2%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

C17H20O5
1033761-69-1

C17H20O5

C42H52O10

C42H52O10

Conditions
ConditionsYield
With dmap; 2,6-di-tert-butyl-4-methyl-phenol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;81%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

cyclohexane-1,4-dicarbonitrile
10534-13-1

cyclohexane-1,4-dicarbonitrile

Conditions
ConditionsYield
With 1,10-Phenanthroline; ammonia; oxygen In 1,4-dioxane at 30 - 60℃; under 3750.38 Torr; for 12h; Pressure; Temperature; Reagent/catalyst; Solvent;80.5%
maleic anhydride
108-31-6

maleic anhydride

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

(Z)-2-butenedioic-acid-1,4-cyclohexanediylbis(methylene) ester
551929-43-2

(Z)-2-butenedioic-acid-1,4-cyclohexanediylbis(methylene) ester

Conditions
ConditionsYield
In acetonitrile at 50℃; for 72h;80%
In acetonitrile at 50℃; for 72h;80%
4-(hydroxymethyl)cyclohexane-1-carboxylic acid
13380-84-2

4-(hydroxymethyl)cyclohexane-1-carboxylic acid

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

[4-(hydroxymethyl)cyclohexyl]methyl 4-(hydroxymethyl)cyclohexane-1-carboxylate

[4-(hydroxymethyl)cyclohexyl]methyl 4-(hydroxymethyl)cyclohexane-1-carboxylate

Conditions
ConditionsYield
Stage #1: bis-1,4-(hydroxymethyl)cyclohexane With dmap; dicyclohexyl-carbodiimide In dimethyl sulfoxide at 20℃; for 0.5h;
Stage #2: 4-(hydroxymethyl)cyclohexane-1-carboxylic acid In dimethyl sulfoxide at 20℃; for 5h;
80%
Stage #1: bis-1,4-(hydroxymethyl)cyclohexane With dmap; dicyclohexyl-carbodiimide In dimethyl sulfoxide at 20℃; for 0.5h;
Stage #2: 4-(hydroxymethyl)cyclohexane-1-carboxylic acid In dimethyl sulfoxide at 20℃; for 5h;
80%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

2-(diphenylmethoxy)-pyridine

2-(diphenylmethoxy)-pyridine

(4-(benzhydryloxymethyl)cyclohexyl)methanol

(4-(benzhydryloxymethyl)cyclohexyl)methanol

Conditions
ConditionsYield
With iron(III) chloride In 1,2-dichloro-ethane at 70℃; for 10h;78%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

(4-chlorophenyl)(phenyl)carbamic chloride
1187856-44-5

(4-chlorophenyl)(phenyl)carbamic chloride

(4-(hydroxymethyl)cyclohexyl)methyl (4-chlorophenyl)(phenyl)carbamate

(4-(hydroxymethyl)cyclohexyl)methyl (4-chlorophenyl)(phenyl)carbamate

Conditions
ConditionsYield
With pyridine at 120℃; for 18h;78%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

1,5-dioxa-3,3-bis(ethoxycarbonyl)-8,8,10,10-tetramethyl-9-azaspiro<5.5>undecane
110844-29-6

1,5-dioxa-3,3-bis(ethoxycarbonyl)-8,8,10,10-tetramethyl-9-azaspiro<5.5>undecane

8,8,10,10-Tetramethyl-1,5-dioxa-9-azaspiro-[5.5]undecane-3,3-dicarboxylic acid
110839-53-7

8,8,10,10-Tetramethyl-1,5-dioxa-9-azaspiro-[5.5]undecane-3,3-dicarboxylic acid

Conditions
ConditionsYield
In dichloromethane; acetic acid77%
Isopropenyl acetate
108-22-5

Isopropenyl acetate

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

A

1,4-cyclohexanedimethylene diacetate
6308-18-5

1,4-cyclohexanedimethylene diacetate

B

diisopropenyl 1,4-cyclohexanedimethanol ether

diisopropenyl 1,4-cyclohexanedimethanol ether

C

C13H22O3

C13H22O3

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium carbonate In toluene at 100℃; for 6h;A n/a
B 75%
C n/a
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

trans-1,4-Cyclohexanedimethanol
3236-48-4

trans-1,4-Cyclohexanedimethanol

Conditions
ConditionsYield
With Ni/NiO-diatomite at 200℃; for 3h; Reagent/catalyst; Autoclave; Inert atmosphere;72.6%
Multi-step reaction with 2 steps
1: 52.1 percent / 140 - 165 °C
2: 46.3 percent / aq. NaOH / 10 h / Heating
View Scheme
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

[4-(p-toluenesulfonyloxymethyl)cyclohexyl]methanol
109004-13-9

[4-(p-toluenesulfonyloxymethyl)cyclohexyl]methanol

Conditions
ConditionsYield
With pyridine; dmap; triethylamine In dichloromethane at 20℃; for 3h;72%
In pyridine at 20℃; for 36h;61%
With pyridine In dichloromethane186 g
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

ethyl 3-diazoindole-2-carboxylate
89607-68-1

ethyl 3-diazoindole-2-carboxylate

3-(4-hydroxymethyl-cyclohexylmethoxy)-3H-indole-2-carboxylic acid ethyl ester

3-(4-hydroxymethyl-cyclohexylmethoxy)-3H-indole-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
dirhodium tetraacetate In dichloromethane at 85℃; for 3h; Substitution; O-H insertation;72%

105-08-8Related news

Enzymatic separation of cis/trans 1,4-Cyclohexanedimethanol (cas 105-08-8) mixtures by mono- and polytransesterification08/22/2019

Lipase-catalyzed poly- and monotransesterification reactions were used in kinetic separations of a commercial mixture of cis,trans-1,4-cyclohexanedimethanol. The reactions were performed with lipases from various sources and with mono- and diesters as the acylating reagents. In a series of monot...detailed

105-08-8Relevant articles and documents

Surface synergistic effect in well-dispersed Cu/MgO catalysts for highly efficient vapor-phase hydrogenation of carbonyl compounds

Liu, Hanwen,Hu, Qi,Fan, Guoli,Yang, Lan,Li, Feng

, p. 3960 - 3969 (2015)

The highly efficient vapor-phase selective hydrogenation of carbonyl compounds (e.g. furfural (FAL) and dimethyl 1,4-cyclohexane dicarboxylate (DMCD)) to corresponding alcohols was achieved excellently over well-dispersed MgO-supported copper catalysts (Cu/MgO), which were prepared by an alternative separate nucleation and aging step method. The characterization results revealed that the structure and catalytic performance of the as-formed Cu/MgO catalysts were profoundly affected by Cu loading. Especially, the results confirmed that the decrease in the Cu loading could lead to the improvement of metal dispersion and the formation of more surface strong Lewis basic sites. In the vapor-phase selective hydrogenation of FAL to furfuryl alcohol (FOL) and DMCD to 1,4-cyclohexane dimethanol (CHDM), two Cu/MgO catalysts with Cu loadings of 27.6 wt% and 70.9 wt% exhibited superior catalytic performance with higher conversions (>97.3%) and selectivities to alcohols (>96.0%) compared to the other supported ones. The high efficiency of the as-formed Cu/MgO catalysts was mainly attributed to the surface synergistic catalytic effect between the catalytically active metallic copper species and the Lewis basic sites, which held the key to the hydrogenation reaction related to the hydrogen dissociation and the activation of the carbonyl groups.

Single-step, highly active, and highly selective nanoparticle catalysts for the hydrogenation of key organic compounds

Raja, Robert,Khimyak, Tetyana,Thomas, John Meurig,Hermans, Sophie,Johnson, Brian F. G.

, p. 4638 - 4642 (2001)

Pores for cluster catalysts: Nanoparticles of both Ru5Pt and Ru10Pt2, uniformly distributed along the inner walls of mesoporous silica, exhibit high catalytic performance in the single-step hydrogenation of dimethyl terephthalate (DMT, to 1,4-cyclohexanedimethanol (CHDM); see scheme), of benzoic acid (to cyclohexane carboxylic acid), and of naphthalene (in the presence of sulfur) to cisdecalin.

Single-step conversion of dimethyl terephthalate into cyclohexanedimethanol with Ru5PtSn, a trimetallic nanoparticle catalyst

Hungria, Ana B.,Raja, Robert,Adams, Richard D.,Captain, Burjor,Thomas, John Meurig,Midgley, Paul A.,Golovko, Vladimir,Johnson, Brian F. G.

, p. 4782 - 4785 (2006)

Highly active and selective: A supported Ru5PtSn nanoparticle cluster (the picture shows an axial projection of a tomogram), prepared from the carbonyl cluster [PtRu5(CO)15(μ-SnPh 2)(μ6-C)], is an excellent catalyst in the single-step hydrogenation of dimethyl terephthalate to cyclohexanedimethanol under mild conditions (100°C, 20 bar H2). (Figure Presented).

Re/AC catalysts for selective hydrogenation of dimethyl 1, 4-cyclohexanedicarboxylate to 1, 4-cyclohexanedimethanol: Essential roles of metal dispersion and chemical environment

Dong, Yanan,Liang, Changhai,Luo, Jingjie,Qu, Enhui,Zhou, Yixue

, (2020)

Rhenium, although viewed as one of the noble metals with lower-price, has been commonly used as doping element in the bimetallic catalysts due to its middlebrow to activate hydrogen. Its major role as catalyst is less frequently mentioned. In this work, rhenium has been decorated on the surface of activated carbon and used for the selective hydrogenation of dimethyl 1, 4-cyclohexanedicarboxylate (DMCD) to 1, 4-cyclohexanedimethanol (CHDM). Characterizations suggested that ReOx particles were anchored occupying the surface oxygenated groups on pre-functionalized carbon. Rhenium decoration modified both the textural and chemical properties of the samples. Electrons were easily transferred from Re to the neighboring C atoms as a result of the formation of fine ReOx particles. Medium strong acid sites were generated and rhenium species in the reduced states could be still maintained under appropriate rhenium dispersion. The moderate hydrogenation ability of rhenium catalyst partially restrained the excessive hydrogenation of CHDM to other by-products. Rational decoration of 5 wt% Re performed the better catalytic performance with complete conversion of diester and 66 % yield of diol. The specific rate reached 9.5×102 mmolDMCD?gRe-1?h-1 at 220 °C under 10 MPa H2.

A Highly Active Manganese Catalyst for Enantioselective Ketone and Ester Hydrogenation

Widegren, Magnus B.,Harkness, Gavin J.,Slawin, Alexandra M. Z.,Cordes, David B.,Clarke, Matthew L.

, p. 5825 - 5828 (2017)

A new hydrogenation catalyst based on a manganese complex of a chiral P,N,N ligand has been found to be especially active for the hydrogenation of esters down to 0.1 mol % catalyst loading, and gives up to 97 % ee in the hydrogenation of pro-chiral deactivated ketones at 30–50 °C.

The role of hydrotalcite-modified porous alumina spheres in bimetallic RuPd catalysts for selective hydrogenation

Chen, Jiali,Guo, Li,Zhang, Fazhi

, p. 19 - 23 (2014)

By utilizing alumina previously modified by in-situ growth of varying amounts of hydrotalcites, a series of heterogeneous bimetallic catalysts with constant low loading (0.3 wt.%) and identical Ru:Pd ratio (1:1) were prepared based on co-impregnation for selective hydrogenation of dimethyl terephthalate to dimethyl cyclohexane-1,4-dicarboxylate. Nanoparticles confined in the reticular structure were observed. The resulting candidates show the superior catalytic activity over that supported on the unmodified alumina, and reach the highest in the optimized sample RuPd/HTC-Al2O 3-1. This promotion and optimization effect could be ascribed to the improved dispersion and more supply of hydrogen and acid sites especially with medium strength.

Preparation method of 1, 4-cyclohexanedimethanol

-

Paragraph 0025; 0030-0116, (2021/08/14)

The invention discloses a preparation method of 1, 4-cyclohexanedimethanol, which is characterized by comprising the following steps of: preparing a supported palladium-based catalyst by using an impregnation method or a liquid phase reduction method, preparing a copper-based catalyst by using a coprecipitation method, mixing the two catalysts, adding a mixture and dimethyl terephthalate into a 1, 4-dioxane solvent, and carrying out a catalytic hydrogenation reaction for preparing CHDM by a one-pot method under electromagnetic stirring, and filtering out the catalyst after the reaction is finished to obtain the product 1, 4-cyclohexanedimethanol. Compared with the prior art, the method has the advantages of good low-temperature reaction activity, high product selectivity and the like, under optimized conditions, the conversion rate of DMT reaches 100%, the yield of CHDM reaches 91% or above, and the research and application field of the reaction of generating CHDM through DMT liquid-phase hydrogenation is further widened.

Catalytic hydrogenation products of aromatic and aliphatic dicarboxylic acids

Shinde, Sunil B.,Deshpande, Raj M.

, p. 1137 - 1142 (2019/04/05)

Hydrogenation of aromatic dicarboxylic acids gave 100 % selectivity to respective cyclohexane dicarboxylic acid with 5 % Pd/C catalyst. 5 % Ru/C catalyst was observed to give over hydrogenation products at 493 K and at lower temperature (453 K) the selectivity for cyclohexane dicarboxylic acids was increased. Hydrogenation of phthalic acid with Ru-Sn/Al2O3 catalyst was observed to give phthalide instead of 1,2-benzene dimethanol or 2-hydroxy methyl benzoic acid. Ru-Sn/Al2O3 catalyst selectively hydrogenated the carboxylic group of cyclohexane dicarboxylic acids to give cyclohexane dimethanol. Use of proper catalysts and reaction conditions resulted in desired products.

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