Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Methods of producing para-xylene and terephthalic acid

A technology of p-xylene and sulfonic acid, which is applied in chemical instruments and methods, preparation of carboxylate, preparation of organic compounds, etc., can solve the problem of reduced selectivity of xylene

Inactive Publication Date: 2015-09-16
MICROMIDAS INC
View PDF6 Cites 11 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such side reactions involving HD lead to reduced selectivity for p-xylene

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Methods of producing para-xylene and terephthalic acid
  • Methods of producing para-xylene and terephthalic acid
  • Methods of producing para-xylene and terephthalic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0333] The embodiments listed below represent some aspects of the invention.

[0334] 1. A method for producing p-xylene, comprising:

[0335] a) providing 2,5-hexanedione;

[0336] b) providing ethylene;

[0337] c) providing a catalyst;

[0338] d) combining 2,5-hexanedione, ethylene and catalyst to form a reaction mixture; and

[0339] e) generating p-xylene from at least a portion of the 2,5-hexanedione in the reaction mixture.

[0340] 2. The method of embodiment 1, further comprising separating paraxylene from the reaction mixture.

[0341] 3. The method of embodiment 1, further comprising providing a solvent system, and combining the 2,5-hexanedione, ethylene, the catalyst, and the solvent system to form a reaction mixture.

[0342] 4. The method of embodiment 3, wherein the solvent system comprises an aprotic solvent.

[0343] 5. The method of embodiment 3, wherein the solvent system comprises an ether solvent.

[0344] 6. The method according to embodiment 3, w...

Embodiment 1

[0469] Preparation of PX from DMF

[0470] A mixture of 5.0 g of DMF, 0.025 g of copper triflate, and 100 mL of dioxane was charged into an autoclave equipped with a gas-entraining impeller. The autoclave was purged three times with nitrogen, once with ethylene, and then pressurized to 500 psig (3,447 kpas) with ethylene. The autoclave was heated to 250°C at which point the pressure was increased to 2250 psig (15,513 kpas). The reactor was kept pressurized at 250°C for 7 hours with the heater turned off and the reactor was allowed to cool at RT. The pressure was released and the reaction solution was poured into a storage bottle. The reaction mixture was a pale yellow solution with a small amount of black precipitate. pass 1 H and 13 C NMR spectroscopy of the solution phase identified residual DMF, PX, ethylene and HD as major components and dioxane as solvent. These components pass 1 The H NMR spectra were quantified and the values ​​are given in Table 1 below. About ...

Embodiment 2

[0476] Preparation of PX from DMF and HD

[0477] A mixture of 8.0 g DMF, 2.0 g HD, 0.5 g yttrium triflate and 200 g dioxane was charged to an autoclave equipped with a gas entrainment propeller. The autoclave was purged three times with nitrogen, once with ethylene, and then pressurized to 500 psig (3,447 kpas) with ethylene. The autoclave was heated to 250°C at which point the pressure was increased to 2,000 psig (13,790 kpas). The reactor was kept pressurized at 250°C for 7 hours. Samples were taken at hourly intervals and analyzed for conversion and selectivity by NMR spectroscopy. After 7 hours, the heater was turned off and the reactor was allowed to cool to RT. The pressure was released and the reaction solution was poured into a storage bottle. After 7 hours 100% conversion was obtained, the molar selectivity of PX based on HD and DMF was 90%, the yield was equal to 90%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The present disclosure provides methods to produce para-xylene, toluene, and other compounds from renewable sources (e.g., cellulose, hemicellulose, starch, sugar) and ethylene in the presence of a catalyst. For example, cellulose and / or hemicellulose may be converted into 2,5-dimethylfuran (DMF), which may be converted into para-xylene by cycloaddition of ethylene to DMF. Para-xylene can then be oxidized to form terephthalic acid.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to U.S. Provisional Patent Application No. 61 / 701,276, filed September 14, 2012, and U.S. Patent Application No. 13 / 838,761, filed March 15, 2013, which are hereby incorporated by reference in their entirety . technical field [0003] This disclosure relates generally to the manufacture of paraxylene and terephthalic acid, and more specifically, to the manufacture of paraxylene and paraxylene from renewable biomass resources (e.g., cellulose, hemicellulose, starch, sugars) and ethylene. Phthalic acid. Background technique [0004] There is a high demand for the production of paraxylene and terephthalic acid from renewable biomass resources for the manufacture of clothing and plastics. Terephthalic acid is a precursor to polyethylene terephthalate (PET) that can be used to make polyester fabrics. Terephthalic acid can be produced by oxidation of p-xylene. [0005] Paraxylene is an a...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C2/86C07C15/08C07C51/265C07C63/26C07C2/46C07C2/62C07C49/14
CPCC07C63/26C07C2527/11C07C2527/173C07C2/865C07C51/265C07C2531/025C07C2529/70C07C2527/126C07C2527/054C07C2523/72C07C2521/08C07C2529/08C07C2/46C07C15/08C07C2531/04C07C2/62C07C49/14C07C2527/19C07C2523/10C07C2527/122C07C2/86C07C2523/28C07C2527/125C07C2/867C07C2531/12C07C2521/04
Inventor 增野真家R·L·史密斯J·比斯尔M·福斯特P·B·史密斯D·A·赫克尔E·J·斯塔克D·R·亨顿A·杜米特拉斯库K·布龙
Owner MICROMIDAS INC
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com