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

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

Uses

Used in Polymer Production:
4-Oxododecanedioic acid is used as a monomer in the production of polymers for various applications due to its ability to form polyamides and polyesters. Its incorporation into these polymers enhances their properties, making them suitable for a wide range of uses.
Used in Adhesives Industry:
In the adhesives industry, 4-Oxododecanedioic acid is used as a component in the formulation of adhesives to improve their bonding strength and durability. Its presence in adhesive formulations contributes to the creation of stronger and more reliable adhesive products.
Used in Coatings Industry:
4-Oxododecanedioic acid is utilized in the coatings industry as a key ingredient in the development of high-quality coatings. It enhances the performance characteristics of coatings, such as their resistance to wear, environmental factors, and overall longevity.
Used in Lubricants Industry:
In the lubricants industry, 4-Oxododecanedioic acid serves as an additive to improve the lubricating properties of various products. Its inclusion in lubricant formulations helps to reduce friction, wear, and tear, thereby extending the life of machinery and components.
Used in Environmentally Friendly Materials:
4-Oxododecanedioic acid is used as a sustainable building block for the synthesis of biodegradable polymers, contributing to the development of eco-friendly materials. Its renewable nature makes it an attractive option for industries seeking to reduce their environmental impact.
Used in Biocompatible Materials:
Due to its potential for use in the synthesis of biodegradable polymers, 4-Oxododecanedioic acid is also utilized in the creation of biocompatible materials. These materials are designed to interact favorably with biological systems, making them suitable for applications in the medical and healthcare sectors.

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

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

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.