Process for conversion of acyclic C5 compounds to cyclic C5 compounds and catalyst composition for use therein

Patent metadata

Field	Value
Publication number	US-10294175-B2
Application number	US-201615288364-A
Country	US
Kind code	B2
Filing date	Oct 7, 2016
Priority date	Nov 4, 2015
Publication date	May 21, 2019
Grant date	May 21, 2019

Abstract

Disclosed is a process for the conversion of acyclic C5 feedstock to a product comprising cyclic C5 compounds, such as for example, cyclopentadiene, and catalyst compositions for use in such process. The process comprising the steps of contacting said feedstock and, optionally, hydrogen under acyclic C5 conversion conditions in the presence of a catalyst composition to form said product. The catalyst composition comprising a crystalline aluminosilicate having a constraint index of less than or equal to 5, and a Group 10 metal, and, optionally, a Group 11 metal, in combination with a Group 1 alkali metal and/or a Group 2 alkaline earth metal.

First claim

What is claimed is:

1. A process for conversion of an acyclic C 5 feedstock to a product comprising cyclic C 5 compounds including cyclopentadiene, said process comprising the steps of contacting said feedstock and, optionally, hydrogen under acyclic C 5 conversion conditions in the presence of a catalyst composition to form said product, wherein said catalyst composition comprises a microporous crystalline aluminosilicate having a constraint index of less than or equal to 5 selected from the group consisting of zeolite beta, mordenite, faujasite, zeolite L, and mixtures of two or more thereof, and a Group 10 metal in combination with a Group 1 alkali metal and/or a Group 2 alkaline earth metal and, optionally, a Group 11 metal.

2. The process of claim 1 , wherein said catalyst composition has Group 10 metal content in the range from 0.005 wt % to 10 wt %, based on the weight of the catalyst composition.

3. The process of claim 1 , wherein said Group 10 metal is platinum, and said Group 11 metal is copper or silver.

4. The process of claim 1 , wherein said Group 1 alkali metal and/or said Group 2 alkaline earth metal is present as an oxide.

5. The process of claim 1 , wherein said Group 1 alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, and mixtures of two or more thereof.

6. The process of claim 1 , wherein said Group 2 alkaline earth metal is selected from the group consisting of beryllium, magnesium, calcium, strontium, barium, and mixtures of two or more thereof.

7. The process of claim 1 , wherein said crystalline aluminosilicate has a SiO 2 /Al 2 O 3 molar ratio of at least 2.

8. The process of claim 1 , wherein said crystalline aluminosilicate has a BET surface area of at least 275 m 2 /g.

9. The process of claim 1 , wherein said crystalline aluminosilicate has a molar ratio of the sum of said Group 1 alkali metal, and said Group 2 alkaline earth metal to Al is at least 0.5.

10. The process of claim 1 , wherein said catalyst composition provides a conversion of at least 20% of said acyclic C 5 feedstock under acyclic C 5 conversion conditions including an n-pentane feedstock with equimolar H 2 , a temperature of 450° C., an n-pentane partial pressure of 7 psia at the reactor inlet (48 kPa-a), and an n-pentane weight hourly space velocity of 2 hr −1 .

11. The process of claim 1 , wherein said catalyst composition provides a carbon selectivity to cyclic C 5 compounds of at least 20% under acyclic C 5 conversion conditions including an n-pentane feedstock with equimolar H 2 , a temperature of 450° C., an n-pentane partial pressure of 7 psia at the reactor inlet (48 kPa-a), and an n-pentane weight hourly space velocity of 2 hr −1 .

12. The process of claim 1 , wherein said acyclic C 5 feedstock comprises pentane, pentene, pentadiene, and mixtures of two or more thereof.

13. The process of claim 1 , wherein said cyclic C 5 compounds comprise cyclopentane, cyclopentene, cyclopentadiene, and mixtures of two or more thereof.

14. The process of claim 1 , wherein said acyclic C 5 feedstock comprises at least 75 wt % n-pentane.

15. The process of claim 1 , wherein said cyclic C 5 compounds comprise at least 20 wt % cyclopentadiene.

16. The process of claim 1 , wherein said acyclic C 5 conversion conditions include at least a temperature of 450° C. to 650° C., the molar ratio of said optional hydrogen co-feed to the acyclic C 5 feedstock is in the range of 0.01 to 3, said acyclic C 5 feedstock has a partial pressure in the range of 3 to 100 psia at the reactor inlet (21 to 689 kPa-a), and said acyclic C 5 feedstock has a weight hourly space velocity in the range from 0.5 to 50 hr −1 .

17. A process for conversion of an acyclic C 5 feedstock to a product comprising cyclic C 5 compounds including cyclopentadiene, said process comprising the steps of contacting said feedstock and, optionally, hydrogen under acyclic C 5 conversion conditions in the presence of a catalyst composition to form said product, wherein said catalyst composition is made by the method comprising the steps of:
(a) providing a crystalline aluminosilicate comprising a Group 1 alkali metal and/or a Group 2 alkaline earth metal and having a constraint index of less than or equal to 5 selected from the group consisting of zeolite beta, mordenite, faujasite, zeolite L, and mixtures of two or more thereof;
(b) optionally, treating said crystalline aluminosilicate with an acid at a PH of greater than or equal to 7 to increase the surface area of said crystalline aluminosilicate and to form an acid-treated aluminosilicate; and
(c) contacting said acid-treated aluminosilicate of step (b) with a source of a Group 10 metal, and, optionally, a Group 11 metal, to form said catalyst composition, whereby said catalyst composition having said Group 10 metal, and/or, optionally, said Group 11 metal, deposited thereon.

18. The process of claim 17 , wherein said Group 10 metal is platinum and said source of platinum is selected from the group consisting of platinum nitrate, chloroplatinic acid, platinous chloride, platinum amine compounds, platinum acetylacetonate, tetraamine platinum hydroxide, and mixtures of two or more thereof, and/or said Group 11 metal is copper and said source of copper is selected from the group consisting of copper nitrate, copper nitrite, copper acetate, copper hydroxide, copper acetylacetonate, copper carbonate, copper lactate, copper sulfate, copper phosphate, copper chloride, and mixtures of two or more thereof, and/or said Group 11 metal is silver and/or said source of silver is selected from the group consisting of silver nitrate, silver nitrite, silver acetate, silver hydroxide, silver acetylacetonate, silver carbonate, silver lactate, silver sulfate, silver phosphate, and mixtures of two or more thereof.

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

• Iaccino Larry L
• Bedard Jeremy W
• Strohmaier Karl G
• Mertens Machteld M W
• Carr Robert T
• Cheng Jane C

Classifications

• B01J29/44

  Noble metals · CPC title

• C07C13/12

  with a cyclopentene ring · CPC title

• B01J29/62

  Noble metals · CPC title

• C07C2529/46

  Iron group metals or copper · CPC title

• C07C13/15

  with a cyclopentadiene ring · CPC title