Alkyl aromatic hydroalkylation for the production of plasticizers
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Solution Overview
Problem
There is a need for alternative non-phthalate plasticizers that offer good melting and chemical stability, compatibility, and low-temperature properties to replace traditional phthalate esters, particularly in applications where phthalates are being phased out due to safety concerns, such as in food-contact materials and medical products.
Innovation Solution
Development of OXO-ester plasticizers, specifically compounds and mixtures of the formula where R1 is a saturated or unsaturated cyclic hydrocarbon optionally substituted with an alkyl and/or OXO-ester, and R2 is a C4 to C14 hydrocarbyl, which are synthesized through processes involving benzene alkylation, oxidation, and esterification, providing a cost-effective and efficient manufacturing route.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If phthalate esters are used as plasticizers, then good plasticizing performance is achieved, but safety concerns arise due to health and environmental issues
Solution Approach 1:
The patent replaces phthalate esters with alternative plasticizers based on benzoic acid, cyclohexanoic acid, or polyketone structures. These alternative plasticizers achieve comparable plasticizing performance without the harmful effects of phthalates, effectively substituting a harmful substance with a safer alternative that fulfills the same functional role
Solution Approach 2:
The patent modifies the chemical structure parameters of plasticizers by using different acid bases (benzoic acid, cyclohexanoic acid, polyketones) and varying alkyl chain lengths (C8-C22). This structural parameter change maintains plasticizing effectiveness while eliminating the harmful properties associated with phthalate esters
2Object-affected harmful factors
If alternative plasticizers are developed to replace phthalates, then safety requirements are met, but successful substitutes have not been found for most applications
Solution Approach 1:
The patent develops plasticizers with universal applicability across multiple polymer systems including PVC, polyvinyl butyral, acrylic polymers, nylon, polyolefins, polyurethanes, and fluoroplastics. The alternative plasticizers based on benzoic acid, cyclohexanoic acid, and polyketones demonstrate multi-functional compatibility, successfully replacing phthalates in diverse applications from food contact materials to medical products and construction materials
Solution Approach 2:
The patent creates composite plasticizer formulations by combining different acid-based esters (benzoic acid esters, cyclohexanoic acid esters, polyketone esters) with various alkyl chains. These composite structures provide both safety compliance and broad compatibility across different polymer matrices, achieving successful substitution in applications where single-component alternatives failed
3Reliability
If existing alternative plasticizers like cyclohexanoate esters are used, then some plasticizing capability is achieved, but they lack broad compatibility and successful performance across different polymer systems
Solution Approach 1:
The patent systematically varies the alkyl chain parameters (length and branching) of the ester components to optimize compatibility with different polymer systems. By adjusting the carbon chain length (C8-C22) and branching structure of the alternative plasticizers, broad adaptability across PVC, acrylics, nylons, polyolefins, polyurethanes, and fluoroplastics is achieved while maintaining plasticizing capability
Solution Approach 2:
The patent develops composite plasticizer systems that combine multiple ester components with different acid bases and alkyl chain characteristics. This composite approach enhances versatility and compatibility across diverse polymer matrices, overcoming the limited adaptability of single-component alternative plasticizers like cyclohexanoate esters
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
The OXO-ester plasticizers demonstrate improved compatibility and stability, effectively replacing traditional phthalate plasticizers in various polymer systems, including PVC, while meeting economic and performance requirements, and extending the flexible temperature range of polyvinyl chloride materials.
Implementation Method 1
benzene alkylation
Implementation Method 2
oxidation
Implementation Method 3
esterification
Data Source
AI summary
Provided are compounds of the following:wherein R1 is a saturated or unsaturated cyclic hydrocarbon optionally substituted with an alkyl and/or an OXO-ester, and R2 is a C4 to C14 hydrocarbyl, preferably the residue of a C4 to C14 OXO-alcohol. Also provided are processes for making the compounds and plasticized polymer compositions containing said compounds.