# US 10,307,745 B2 · Catalysts for making acrylic acid from lactic acid or its derivatives in liquid phase

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- Number: US 10,307,745 B2
- Document ID: US10307745B2
- Status: Granted
- Kind: B2
- Application number: 15/661,016
- Filed: 2017-07-27
- Published: 2018-02-01
- Granted: 2019-06-04
- Earliest claimed: 2016-07-29
- Assignees: The Procter & Gamble Company
- Applicants: The Procter & Gamble Company; Friedrich Alexander Universitat Erlangen-Nurnberg
- Inventors: Jakob Albert; Peter Wasserscheid; Nicola Taccardi; Jens Nagengast; Matthias Kehrer; Julian Kadar; Dimitris Ioannis Collias
- Web page: https://patentgrep.com/patent/US10307745B2

## CPC

- B01J 31/0288: {Phosphorus}
- B01J 27/02: Sulfur, selenium or tellurium; Compounds thereof
- B01J 27/06: Halogens; Compounds thereof
- B01J 27/122: of copper
- B01J 27/125: with scandium, yttrium, aluminium, gallium, indium or thallium
- B01J 27/138: with alkaline earth metals, magnesium, beryllium, zinc, cadmium or mercury
- B01J 27/16: containing oxygen {, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr}
- B01J 31/0298: {the ionic liquids being characterised by the counter-anions}
- B01J 31/04: containing carboxylic acids or their salts {(B01J31/0277 - B01J31/0298 take precedence; multi-metal carboxylate complexes like Pd (II) acetate, i.e. Pd3 (OAc) 6 or Cr(II)acetate, i.e. Cr2(OAc)4 B01J31/2226)}
- B01J 31/26: containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

Catalysts for the dehydration of lactic acid, lactic acid derivatives, or mixtures thereof to acrylic acid, acrylic acid derivatives, or mixtures thereof in liquid phase comprising an ionic liquid (IL) and an acid are provided.

## Claims

### Claim 1

A molten salt catalyst comprising an ionic liquid (IL) and an acid; wherein said IL is ethyltriphenylphosphonium bromide ([EtPPh3]Br); wherein said acid is soluble in said IL and selected from the group consisting of Lewis acid, Brønsted acid, and mixtures thereof; wherein said Lewis acid is selected from the group consisting of CaBr2, MgBr2, AlBr3, CuBr2, and mixtures thereof; and wherein said Brønsted acid has a pKa less than about 5 in water at 25° C.

### Claim 2 (depends on 1)

The catalyst of claim 1, wherein said Brønsted acid is hydrobromic acid (HBr).

### Claim 3 (depends on 2)

The catalyst of claim 2, wherein the molar ratio of said [EtPPh3]Br to said HBr is between about 1 and about 20.

### Claim 4 (depends on 3)

The catalyst of claim 3, wherein the molar ratio of said [EtPPh3]Br to said HBr is between about 2 and about 5.

### Claim 5 (depends on 4)

The catalyst of claim 4, wherein the molar ratio of said [EtPPh3]Br to said HBr is about 4.

### Claim 6

A molten salt catalyst comprising an ionic liquid (IL) and an acid; wherein said IL is tetrabutylphosphonium bromide ([PBu4]Br); wherein said acid is soluble in said IL and selected from the group consisting of Lewis acid, Brønsted acid, and mixtures thereof; wherein said Lewis acid is selected from the group consisting of CaBr2, MgBr2, AlBr3, CuBr2, and mixtures thereof; and wherein said Brønsted acid is pyrophosphoric acid (H4P2O7).

### Claim 7 (depends on 6)

The catalyst of claim 6, wherein the molar ratio of said [PBu4]Br to said H4P2O7 is between about 1 and about 30.

### Claim 8 (depends on 7)

The catalyst of claim 7, wherein the molar ratio of said [PBu4]Br to said H4P2O7 is about 4.75.

### Claim 9

A molten salt catalyst comprising an ionic liquid (IL) and an acid; wherein said IL is tetrabutylphosphonium bromide ([PBu4]Br); and wherein said acid is selected from the group consisting of sulfuric acid (H2SO4), phosphoric acid (H3PO4), and 2-bromopropionic acid (2-BrPA).