30828-09-2

Basic information

• Product Name: 4-Oxododecanedioic acid
• Synonyms: 4-Oxododecanedioic acid
• CAS NO: 30828-09-2
• Molecular Formula: C₁₂H₂₀O₅
• Molecular Weight: 244
• Mol File: 30828-09-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 106-109 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 472.4±25.0 °C(Predicted)
• Appearance: /
• Density: 1.146±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 4.77±0.17(Predicted)
• CAS DataBase Reference: 4-Oxododecanedioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Oxododecanedioic acid(30828-09-2)
• EPA Substance Registry System: 4-Oxododecanedioic acid(30828-09-2)

Safety Data

• Hazardous Substances Data: 30828-09-2(Hazardous Substances Data)

Usage

General Description

4-Oxododecanedioic acid, also known as 4-ketododecanedioic acid, is a dicarboxylic acid with the chemical formula C12H22O5. It is a white crystalline compound that is used in the production of polymers, such as polyamides and polyesters. 4-Oxododecanedioic acid has been studied for its potential as a renewable and sustainable building block for the synthesis of biodegradable polymers. It is also used in various industrial applications, such as in the production of adhesives, coatings, and lubricants. 4-Oxododecanedioic acid has attracted interest for its potential use in the development of environmentally friendly and biocompatible materials.

Synthetic route

2,2-dimethyl-4,6-dioxo-5-(2-oxo-9-carbomethoxynonyl)-1,3-dioxane (85060-85-1) → 4-ketododecanedioic acid (30828-09-2)

Conditions	Yield
With hydrogenchloride; acetic acid 1) H2O, reflux, 3 h, 2) reflux, 3 h; Yield given. Multistep reaction;
With hydrogenchloride; acetic acid 1.) reflux, 3 h, 2.) reflux, 3 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: AcOH / H2O / 4 h / Heating 2: 0.7 g / conc. HCl / 4 h / Heating View Scheme

4-Oxo-dodecanedioic acid 12-methyl ester (74017-21-3) → 4-ketododecanedioic acid (30828-09-2)

Conditions	Yield
With hydrogenchloride for 4h; Heating;	0.7 g

methyl 9-oxodecanoate (2575-07-7) → 4-ketododecanedioic acid (30828-09-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) Br2, urea, 2.) KOH (aq.), Et4NI / 1.) MeOH, 20 deg C, 8 h, 2.) DMF, 20 deg C, 24 h 2: 1.) AcOH(aq.), 2.) HCl(conc.) / 1.) reflux, 3 h, 2.) reflux, 3 h View Scheme
Multi-step reaction with 3 steps 1: 1.) bromine, 2.) Et4N+I-, KOH / 1.) MeOH, ca.20 deg C, 1 h, 2.) DMF, water, 20 deg C, 48 h 2: AcOH / H2O / 4 h / Heating 3: 0.7 g / conc. HCl / 4 h / Heating View Scheme
Multi-step reaction with 3 steps 1: Br2, urea / dimethylformamide / 2 h 2: AcONa*3H2O / dimethylformamide / 24 h / 20 °C 3: 1) acetic acid, 2) conc. HCl / 1) H2O, reflux, 3 h, 2) reflux, 3 h View Scheme

10-bromo-9-ketodecanoic acid methyl ester (85060-82-8) → 4-ketododecanedioic acid (30828-09-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: AcONa*3H2O / dimethylformamide / 24 h / 20 °C 2: 1) acetic acid, 2) conc. HCl / 1) H2O, reflux, 3 h, 2) reflux, 3 h View Scheme

methanol (67-56-1) + 4-ketododecanedioic acid (30828-09-2) → 4-ketododecanedioic acid dimethyl ester (30828-10-5)

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 96h;	62%

diazomethane (186581-53-3, 908094-01-9) + 4-ketododecanedioic acid (30828-09-2) → 4-ketododecanedioic acid dimethyl ester (30828-10-5)

Upstream product

• 85060-85-1 2,2-dimethyl-4,6-dioxo-5-(2-oxo-9-carbomethoxynonyl)-1,3-dioxane 
• 74017-21-3 4-Oxo-dodecanedioic acid 12-methyl ester 
• 2575-07-7 methyl 9-oxodecanoate 
• 85060-82-8 10-bromo-9-ketodecanoic acid methyl ester 

Relevant articles and documents

SYNTHESIS OF 4-OXODODECANOIC AND 4-OXODODECANEDIOIC ACIDS

A short synthesis is described for 4-oxododecanoic acid starting from 1-decene or 2-decanone and of 4-oxododecanedioic acid from the methyl ester of 9-oxodecanoic acid.

SYNTHESIS OF DIMETHYL ESTER OF 4-KETODODECANEDIOIC ACID

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