TRANS-1,4-CYCLOHEXANEDICARBOXYLIC ACID MONOMETHYL ESTER Chemical Properties

Melting point:

126.0 to 130.0 °C

Boiling point:

303.1±35.0 °C(Predicted)

Density 

1.191±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

4.66±0.10(Predicted)

color 

White to Almost white

InChI

InChI=1S/C9H14O4/c1-13-9(12)7-4-2-6(3-5-7)8(10)11/h6-7H,2-5H2,1H3,(H,10,11)/t6-,7-

InChIKey

ZQJNPHCQABYENK-LJGSYFOKSA-N

SMILES

[C@@H]1(C(OC)=O)CC[C@@H](C(O)=O)CC1

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2917200090

TRANS-1,4-CYCLOHEXANEDICARBOXYLIC ACID MONOMETHYL ESTER Usage And Synthesis

Uses

Trans-cyclohexane-1,4-dicarboxylic acid monomethyl ester is a carboxylic acid ester derivative, used as organic reagents.

Synthesis

(1) Isomerization reaction: 0.5 mol (100.1 g) of dimethyl 1,4-cyclohexanedicarboxylate (Ib) with a trans/cis isomer ratio of 3/7 to 5/5 was dissolved in 200 g of methanol at 40°C. The reaction was carried out by adding 15 g of pyridine as a catalyst. 15 g of pyridine was added as a catalyst, and after 2 h of reaction, a methanolic solution of dimethyl 1,4-cyclohexanedicarboxylate (II-b) with a trans/cis isomer ratio of 9/1 was obtained. (2) Monoester hydrolysis reaction: The methanol solution of dimethyl 1,4-cyclohexanedicarboxylate (II-b) with a trans/cis isomer ratio of 9/1 obtained in step (1) was cooled to room temperature, and 150 g of potassium hydroxide was added. The reaction was carried out at 20°C for 3 h. Monoester hydrolysis was carried out to obtain a water-soluble carboxylic acid ester of trans-1,4-cyclohexanedicarboxylic acid monomethyl ester. (3) Acidification and post-treatment: 200 g of water and 100 g of toluene were added to the reaction system of step (2), and the organic phase was removed by extraction and stratification. The aqueous phase was adjusted to pH 1-2 with concentrated hydrochloric acid and the mixture was cooled to 0 °C. After filtration, the mixture was dried under reduced pressure at 50 °C to afford 66.4 g of white solid powder of monomethyl trans-1,4-cyclohexanedicarboxylate (III). The yield was 71.32% and the purity of compound (III) was 98.9% as determined by gas chromatography.

References

[1] Patent: CN108129307, 2018, A. Location in patent: Paragraph 0027-0041

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