Propylene polyol conversion to olefin monomer

Patent metadata

Field	Value
Publication number	US-2024182389-A1
Application number	US-202318526362-A
Country	US
Kind code	A1
Filing date	Dec 1, 2023
Priority date	Dec 2, 2022
Publication date	Jun 6, 2024
Grant date	—

Abstract

Processes for conversion of propylene polyol feed into useful petrochemical products, including olefin monomers, are described. Such processes comprise: adding a feed stream comprising one or more propylene polyols, hydrogen, and optionally water, to a catalytic conversion reaction zone in the presence of a first solid acid catalyst component and a hydrogenation catalyst component and reacting at a pressure and temperature sufficient to form a first product stream comprising a propanol component. The first product stream can be added to a dehydration reaction zone in the presence of a dehydration catalyst and reacted at a pressure and temperature sufficient to form a second product stream comprising propylene.

First claim

What is claimed is:

1 . A process comprising:
a) adding a feed stream comprising one or more propylene polyols, hydrogen, and optionally water, to a catalytic conversion reaction zone in the presence of a first solid acid catalyst component and a hydrogenation catalyst component to form a first reaction mixture; and b) reacting the first reaction mixture at a temperature in the range of from 20° ° C. to 600° C., a pressure in the range of from 100 psig (689 kPag) to 1,500 psig (10,340 kPag), or a combination thereof, to form a hydrogenation product stream comprising a propanol component.

2 . The process of claim 1 , wherein the feed stream is added to the catalytic conversion reaction zone at a weight hourly space velocity in the range of from 0.1 h −1 to 100 h −1 .

3 . The process of claim 1 , wherein the one or more propylene polyols comprise propylene glycol, di-propylene glycol, tri-propylene glycol, tetra-propylene glycol, or a combination thereof.

4 . The process of claim 1 , wherein the catalytic conversion product comprises 0 wt % to 90 wt % water and 10 wt % to 100 wt % organics other than water, wherein weight percentages are based on the total weight of the catalytic conversion product.

5 . The process of claim 4 , wherein the organics other than water comprise 1-propanol in the range of from 50 wt % to 90 wt % and other C 3 hydrocarbons in the range of from 10 wt % to 50 wt %, wherein weight percentages are based on the total weight of the organics other than water.

6 . The process of claim 1 , wherein the catalytic conversion product stream further comprises a propylene precursor component.

7 . The process of claim 6 , wherein the propylene precursor component comprises 1-propanol, 2-propanol, propionaldehyde, acetone, C 3 dioxanes, C 3 dioxolanes, propylene glycol, hydroxyacetone, or a combination thereof.

8 . The process of claim 1 , further comprising adding at least a portion of the catalytic conversion product to the catalytic conversion reaction zone.

9 . The process of claim 1 , wherein the first solid acid catalyst component comprises a zeolite component, an alumina silicate component, aluminum phosphate, zirconium sulfate, titanium sulfate, supported phosphoric acid, one or more supported tungsten oxides, supported tungstosilicic acid, supported phosphomolybdic acid, aluminum oxide, niobium oxide, one or more polystyrene sulfonate acidic resins, sulfonate functionalized support, tethered organic sulfonic acids, acidic clays, or a combination thereof.

10 . The process of claim 1 , wherein the hydrogenation catalyst component comprises sulfided NiMo/Al 2 O 3 , sulfided CoMo/Al 2 O 3 , Ni/SiO 2 , Ni/Al 2 O 3 , Raney Ni, Cu/SiO 2 , Cu/Al 2 O 3 , Pd/SiO 2 , Pd/Al 2 O 3 , Pd/C, Pt/SiO 2 , Pt/Al 2 O 3 , Ru/C, In 2 O 3 In 2 O 3 /Al 2 O 3 , In 2 O 3 /SiO 2 , or a combination thereof.

11 . The process of claim 1 , wherein:
a) the first solid acid catalyst component is a first discrete catalyst, and the hydrogenation catalyst component is a second discrete catalyst; or b) a hybrid catalyst comprises the first solid acid catalyst component and the hydrogenation catalyst component.

12 . The process of claim 1 , further comprising:
a) adding the catalytic conversion product stream to a dehydration reaction zone in the presence of a second solid acid catalyst to form a second reaction mixture; and b) reacting the second reaction mixture at a temperature in the range of from 20° C. to 600° C., a pressure in the range of from 15 psig (103 kPag) to 500 psig (689 kPag), or a combination thereof, to form a dehydration product stream comprising propylene.

13 . The process of claim 12 , wherein the catalytic conversion product stream is added to the dehydration reaction zone at a weight hourly space velocity in the range of from 0.1 h −1 to 100 h −1 .

14 . The process of claim 12 , wherein the second solid catalyst component comprises a zeolite component, an alumina silicate component, aluminum phosphate, zirconium sulfate, titanium sulfate, supported phosphoric acid, one or more supported tungsten oxides, supported tungstosilicic acid, supported phosphomolybdic acid, aluminum oxide, niobium oxide, or a combination thereof.

15 . The process of claim 1 , further comprising adding an organic waste stream, comprising one or more propylene polyols and a first content of one or more impurities harmful to the first solid acid catalyst component and/or the hydrogenation catalyst component, to a guard reaction zone to form the feed stream comprising one or more propylene polyols.

16 . The process of claim 15 , wherein the impurities comprise amines, urethane, amides, other nitrogen containing hydrocarbons, organic bases, caustic, or a combination thereof.

17 . A process comprising:
a) adding a feed stream comprising one or more propylene polyols, hydrogen, and optionally water, to a catalytic conversion reaction zone in the presence of a first solid acid catalyst component and a hydrogenation catalyst component to form a first reaction mixture; b) reacting the first reaction mixture at a temperature in the range of from 20° C. to 600° C., a pressure in the range of from 100 psig (689 kPag) to 1,500 psig (10,340 kPag), or a combination thereof, to form a catalytic conversion product stream comprising a propanol component; and c) adding the catalytic conversion product to a first distillation column to produce a catalytic conversion product overhead stream and a catalytic conversion product bottoms stream and withdrawing the catalytic conversion overhead product stream as a first conversion product.

18 . The process of claim 17 , further comprising adding at least a portion of the first conversion product to the catalytic conversion reaction zone.

19 . The process of claim 17 , further comprising:
a) adding the first conversion product to a dehydration reaction zone in the presence of a second solid acid catalyst to form a second reaction mixture; and b) reacting the second reaction mixture at a temperature in the range of from 20° ° C. to 600° C., a pressure in the range of from 15 psig (103 kPag) to 500 psig (689 kPag), or a combination thereof, to form a dehydration product stream comprising propylene.

20 . The process of claim 19 , further comprising:
a) withdrawing the dehydration product as a first propylene-containing product; or b) routing the dehydration product to a second distillation column to produce a dehydration product overhead stream and a dehydration product bottoms stream and withdrawing the dehydration overhead product as a second propylene-containing product.

Assignees

• Basell Poliolefine Italia Srl

Inventors

• Nagy Sandor
• Mannel David S
• Nagy Natalia
• Rose Amy D
• Horvat George R
• Arndt Larry W
• Leyshon David W
• Yang Xueyong
• Kimmich Barbara

Classifications

• C07C29/60 Primary

  by elimination of -OH groups, e.g. by dehydration (C07C29/34 takes precedence) · CPC title

• C07C1/24

  by elimination of water · CPC title

• C07C29/80

  by distillation · CPC title

• C07C29/132 Primary

  by reduction of an oxygen containing functional group · CPC title

• C07C2527/167

  Phosphates or other compounds comprising the anion (PnO3n+1)(n+2)- · CPC title