Process and composition for inhibiting the polymerization of cyclopentadiene compounds

Patent metadata

Field	Value
Publication number	US-9493382-B2
Application number	US-201414217588-A
Country	US
Kind code	B2
Filing date	Mar 18, 2014
Priority date	Mar 20, 2013
Publication date	Nov 15, 2016
Grant date	Nov 15, 2016

Abstract

A process for inhibiting the polymerization of cyclopentadiene compounds (B) by contacting the cyclopentadiene compound with a quinone methide compound (A) of structure (I),

Compositions (AB) comprising (A) and (B) are also provided.

First claim

The invention claimed is:

1. A process for inhibiting the polymerization of a cyclopentadiene compound (B), comprising:
contacting the cyclopentadiene compound (B) with at least one compound (A);

wherein
(A) is a compound of structure (I)

wherein
R 1 and R 2 are each independently hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 3 to 15 carbon atoms, aryl of 6 to 15 carbon atoms or phenylalkyl of 7 to 15 carbon atoms;
R 3 is 2-furyl, 3-furyl or phenyl.

2. The process according to claim 1 , wherein
R 1 and R 2 are each tert-butyl in the compound of structure (I).

3. The process according to claim 1 , wherein the cyclopentadiene compound is at least one selected from the group consisting of cyclopentadiene, dicyclopentadiene, alkylated cyclopentadiene and alkylated dicyclopentadiene.

4. The process according to claim 1 , wherein the cyclopentadiene compound is at least one of cyclopentadiene and dicyclopentadiene.

5. The process according to claim 1 , wherein (A) is in the form of a solution (AC) in (C), wherein (C) is at least one solvent selected from the group consisting of benzene, a mono-alkylated aromatic compound, a polyalkylated aromatic compound, an alkane having a carbon number of 6 to 15, a cycloalkane having a carbon number of 6 to 15, a high-boiling hydrocarbon cut, an ether having a carbon number of 6 to 15 and an ester having a carbon number of 6 to 15.

6. The process according to claim 5 , wherein a ratio (m/m) of a total weight of all compounds of structure (I) in solution (AC) to a total weight of all solvents in solution (AC) is from 1:1000 to 100:1.

7. The process according to claim 1 , wherein a total concentration of all compounds of structure (I) is between 10 ppb (m/m) and 100,000 ppm (m/m), based on the total weight of all cyclopentadiene compounds.

8. The process according to claim 1 , wherein (B) is a component of a process stream and a concentration of (B) is 0.0001 to 15 wt % based on the total weight of the process stream.

Assignees

• Rinker Stefanie
• Ludwig Bettina
• Neumann Manfred
• Nissen Felix
• Erpeldinger Oliver
• James Phillip R
• Watkins Peter
• Evonik Degussa Gmbh

Inventors

• Rinker Stefanie
• Ludwig Bettina
• Neumann Manfred
• Nissen Felix
• Erpeldinger Oliver
• James Phillip R
• Watkins Peter

Classifications

• C07C7/20 Primary

  Use of additives, e.g. for stabilisation · CPC title

• C07C2601/10

  the ring being unsaturated · CPC title

• C09K15/20

  containing nitrogen and oxygen · CPC title

• C07C2603/68

  Dicyclopentadienes; Hydrogenated dicyclopentadienes · CPC title

• C09K15/08

  containing a phenol or quinone moiety · CPC title