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EP-4735427-A1 - A PROCESS OF COUPLING ALDEHYDES

EP4735427A1EP 4735427 A1EP4735427 A1EP 4735427A1EP-4735427-A1

Abstract

A process of coupling aldehydes is disclosed. The process comprises passing an aldehyde stream and a catalyst stream comprising a homogeneous catalyst in an alcohol solution to a reactor. The aldehyde stream is mixed with the homogeneous catalyst in the alcohol solution. A furoin based molecule is precipitated from the solution in the reactor. A liquid stream comprising the homogeneous catalyst in the alcohol solution is recovered from the reactor. The liquid stream comprising the homogeneous catalyst in the alcohol solution is recycled to the reactor to couple the fresh supply of the aldehyde stream.

Inventors

  • BRODERICK, Erin M.
  • HICKMAN, AMANDA
  • KUZMANICH, Gregory B.

Assignees

  • UOP LLC

Dates

Publication Date
20260506
Application Date
20240813

Claims (10)

  1. 1. A process of coupling aldehydes, comprising: charging an aldehyde containing stream and a catalyst stream comprising a catalyst in an alcohol solution to a reactor: contacting said aldehyde containing stream with said catalyst in the alcohol solution; precipitating a furoin based molecule in said reactor; and recovering a liquid stream comprising said catalyst in the alcohol solution from the reactor.
  2. 2. The process of claim 1 wherein said liquid stream comprising said catalyst in the alcohol solution is recycled to the reactor.
  3. 3. The process of claim 1 wherein said aldehyde containing stream comprises one or more aldehydes having formula (I) , wherein Rl, R2, and R3 is selected from a group comprising hydrogen, C1-C20 alkyl chains, aromatic groups, heteroatoms, and oxygenated groups comprising alcohols, ethers, carbonyls, esters, and hydroxyls, and X is selected from a group comprising heteroatoms, oxygen, sulfur, and nitrogen.
  4. 4. The process of claim 1 wherein the aldehyde containing stream comprises furfural.
  5. 5. The process of claim 1 wherein said furoin based molecule is hydrodeoxygenated to a liquid fuel.
  6. 6. The process of claim 1 wherein said furoin based molecule is hydrodeoxygenated and then dehydrogenated to produce a product comprising olefins having from 8 to 16 carbons.
  7. 7. The process of claim 1 wherein said homogeneous catalyst is a N- heterocyclic carbene catalyst.
  8. 8. The process of claim 7 wherein said catalyst is selected from TPT, 1,3-di- mesityl-butyl-imidazolin-2-ylidene and l,3-dialkylimidazolin-2-ylidene.
  9. 9. The process of claim 1 wherein the furoin based molecule comprises one or more compound having formula (II) , wherein Rl, R2, and R3 is selected from a group comprising hydrogen, C1-C20 alkyl groups, aromatic groups, heteroatoms, and oxygenated groups comprising alcohols, ethers, carbonyls, esters, and hydroxyls, and X is selected from a group comprising oxygen, sulfur, and nitrogen.
  10. 10. The process of claim 1 wherein furoin based molecule comprises 5,5'- di(hydroxymethyl)furoin.

Description

A PROCESS OF COUPLING ALDEHYDES STATEMENT OF PRIORITY [0001] This application claims priority to U.S. Patent Application Ser. No. 18/453,220 filed on August 21, 2023, the entirety of which is incorporated herein by reference. FIELD [0002] The field is related to a process of coupling aldehydes. The field may particularly relate to a process of coupling aldehydes and recycling a catalyst stream for coupling aldehydes. BACKGROUND [0003] As the demand for fuel increases worldwide, there is increasing interest in producing fuels and blending components from sources other than crude oil. Often referred to as biorenewable sources, these sources include, but are not limited to, plant oils such as com, rapeseed, canola, soybean, microbial oils such as algal oils, animal fats such as inedible tallow, fish oils and various waste streams such as yellow and brown greases and sewage sludge. A common feature of these sources is that they are composed of glycerides and free fatty acids (FFA). Both triglycerides and the FFAs contain aliphatic carbon chains having from 8 to 24 carbon atoms. The aliphatic carbon chains in triglycerides or FFAs can be fully saturated or mono, di or poly-unsaturated. [0004] With an increased focus on sustainability, the need for sustainable aviation fuels (SAF) has grown due to the decrease in greenhouse gases (GHG) emissions of SAF compared to petrochemically sourced fuel. There is increasing support and demand across the globe for SAF with the government offering subsidies and mandating the production of carbon-neutral jet fuel. In recent years, considerable research has been devoted to finding effective and efficient means of producing the SAF. As the demand for SAF increases worldwide, there is an increasing interest in sources other than petroleum crude oil for producing the SAF. [0005] Light weight olefins have traditionally been produced through the process of steam or catalytic cracking. Light weight olefins serve as feeds for the production of numerous chemicals. However, the use of petroleum sources as feed leads to GHG emissions. Researchers and refineries are looking for alternate sources for these processes. The search for alternative materials for light weight olefin production has led to the use of oxygenates. Oxygenates may provide non-petroleum-based routes for the production of olefins and other hydrocarbons. However, there is a need for a consistent supply of sources for oxygenates to meet the demand of lightweight olefins. [0006] Azolium compounds such as a thiazolium salt, an imidazolium salt and a triazolium salt are known to be used as catalysts for aldehyde coupling reactions such as benzoin condensation. The coupled product of aldehyde coupling reactions include alkanes which can be converted to other products including fuels. However, these azolium compounds are difficult to recover and, hence, their industrial use as catalysts is difficult. For this reason, azolium compounds are used as supported catalysts on organic or inorganic carriers. However, these azolium compound supported catalysts have problems such as insufficient yield, precipitous reduction in catalyst activity, and poor recyclability. [0007] The anticipation of stagnation in growth of high fructose com syrup could lead to stranded sugars in the future. It would be desirable to have an effective pathway for converting sugars to hydroxymethfurfural (HMF) which may be processed to produce sustainable aviation fuel meeting fuel specifications and to other chemicals such as olefins. SUMMARY OF THE INVENTION [0008] A process of coupling aldehydes is disclosed. The process discloses contacting an aldehyde containing stream with a catalyst stream of a catalyst in an alcohol solution. The coupling reaction produces a furoin based molecule which is withdrawn. A liquid stream of catalyst in the alcohol solution is also withdrawn from the reactor. The process recycles the used catalyst back to the reactor to couple a fresh supply feed of aldehyde. It is demonstrated that the recycled catalyst for the coupling reaction has produced a commensurate yield compared to fresh catalyst. Also, the furoin based molecule may be processed to produce SAF or olefin. BRIEF DESCRIPTION OF THE DRAWINGS [0009] FIG. l is a simplified process flow diagram of the process of coupling aldehydes in accordance with an exemplary embodiment of the present disclosure. [0010] FIG. 2 is a graph plotted between the 5,5'-di(hydroxymethyl)furoin (DHMF) % yield vs time (min) in accordance with another exemplary embodiment of the present disclosure. [0011] FIG. 3 is a graph plotted between the variation of DHMF % yield vs water content of a used solvent in accordance with yet another exemplary embodiment of the present disclosure. [0012] FIG. 4 is a graph plotted to show the variation of DHMF % yield with a mole ratio of the aldehyde and catalyst at different water concentrations in alcohol as the solvent in accordance with still another exempl