Homogeneous hydrogenation of esters employing a complex of iron as catalyst

A technology of catalysts and complexes, applied in the field of homogeneous hydrogenation of esters using iron complexes as catalysts, can solve the problems of energy and capital consumption, and achieve the effect of reducing the generation and elimination of harmful wastes

Inactive Publication Date: 2016-11-23
PROCTER & GAMBLE CO +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although effective, these methods are extremely energy and money intensive

Method used

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  • Homogeneous hydrogenation of esters employing a complex of iron as catalyst
  • Homogeneous hydrogenation of esters employing a complex of iron as catalyst
  • Homogeneous hydrogenation of esters employing a complex of iron as catalyst

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Example 1 - Catalyst Synthesis

Embodiment 1A

[0033] Example 1A - Synthesis [ iPr PN(H)P]Fe(CO)Br 2 (Formula 6). In the glove box, add anhydrous FeBr to a 100 mL oven-dried Schlenk bottle equipped with a stir bar 2 (510 mg, 2.36 mmol) and 30 mL THF to give an orange solution. Add to( i PR 2 PCH 2 CH 2 ) NH (10% by weight, 9.0mL, 2.60mmol) THF solution, and then with FeBr 2 When the solution was mixed for several minutes, a thick white precipitate formed. The flask was connected to a Schlenk line and the argon inside the flask was replaced with CO by performing a freeze-pump-thaw cycle. When mixed with CO and warmed to room temperature, the white precipitate dissolved rapidly to give a dark blue solution. The solution was stirred at 15 psig CO for 1 h, then evaporated to dryness under vacuum. The resulting blue residue was washed with pentane (15 mL×3), and dried under vacuum to give the title compound (1.20 g, 93% yield) as a blue powder. of this complex 1 The H NMR spectrum showed broad resonances, presumably...

Embodiment 1B-

[0034] Example 1B - Synthesis [ iPr PN(H)P]Fe(H)(CO)(BH 4 ) (Formula 2). To a 100 mL oven-dried Schlenk flask equipped with a stir bar was added formula 6 (400 mg, 0.73 mmol) and NaBH under argon atmosphere 4 (138 mg, 3.65 mmol). To this mixture was first added 50 mL of anhydrous degassed ethanol at 0°C, resulting in a green solution which turned yellow in color within a few minutes. The resulting mixture was gradually warmed to room temperature and then stirred for an additional 16 h. The volatiles were removed in vacuo to give a yellow solid, which was treated with 80 mL of toluene and filtered through a pad of celite to give a yellow solution. The solvent was evaporated in vacuo to give the desired compound as a bright yellow powder (250 mg, 85% yield). This compound can be briefly exposed to air without appreciable decomposition.

[0035] Similarly by formula 6 and NaBD 4 synthesis[ iPr PN(H)P]Fe(D)(CO)(BD 4 )(Formula 2-d 5 ). 1 H NMR (400MHz, C 6 D 6 ,δ): –19...

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Abstract

The homogeneous hydrogenation of organic carbonyls, especially esters, under relatively mild conditions using iron hydrido-borohydride catalyst complexes having amino-phosphine pincer ligands. The catalyst and process are well-suited for catalyzing the hydrogenation of a wide variety of organic carbonyls, such as hydrogenation of fatty acid esters to alcohols. In particular embodiments, the process can be carried out in the absence of solvent.

Description

technical field [0001] The present invention relates to a homogeneous process for the hydrogenation of organic carbonyl compounds. Background technique [0002] The hydrogenation of esters is an industrially important process and is used in many applications to manufacture alcohols on a scale of millions of tons per year. In particular, long-chain or fatty alcohols are widely used as precursors of surfactants, plasticizers and solvents. Worldwide consumption of fatty alcohols grew to 2.2 million metric tons in 2012, and global demand is expected to increase at a CAGR of 3-4% from 2012 to 2020. Currently, about 50% of fatty alcohols are considered "natural fatty alcohols" because they are produced by hydrogenating fatty acid methyl esters derived from coconut and palm kernel oils, as well as other renewable materials. [0003] Currently used for the hydrogenation of large-scale esters to fatty alcohols (e.g., detergent-length methyl esters, mainly C 12 –C 14 ) techniques ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/24C07C29/149C07C33/22C07C33/20C07C33/46C07C31/125C07C31/135C07C41/26C07C43/23C07C37/00C07C39/08
CPCB01J31/2476C07C29/149C07C37/00C07C41/26B01J2531/842B01J2531/0244B01J2231/643C07C33/22C07C33/20C07C33/46C07C31/125C07C31/135C07C43/23C07C39/08C07C31/207B01J31/2295B01J31/20B01J31/16B01J2231/64
Inventor N·T·费尔韦瑟M·S·吉布森管海荣S·查克拉博蒂戴辉光P·巴塔查亚
Owner PROCTER & GAMBLE CO
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