Process for Aluminum Catalyst Deactivation and Removal from Alkylated Phenols

Abstract

A method having the steps of heating a first mixture to at least 40 C. for a first period of time, wherein the first mixture contains the following two substances: a first aluminum-containing species and an alkylated phenol compound; after heating the first mixture to at least 40 C. for a first period of time, adding water to the first mixture to thereby create a second mixture, wherein the second mixture contains the following two substances: a second aluminum-containing species and the alkylated phenol compound; and removing the second aluminum-containing species from the second mixture by passing the second mixture through a first filter.

Claims

1. A method comprising the steps: heating a first mixture to at least 40 C. for a first period of time, wherein the first mixture contains the following two substances: a first aluminum-containing species and an alkylated phenol compound; after heating the first mixture to at least 40 C. for a first period of time, adding water to the first mixture to thereby create a second mixture, wherein the second mixture contains the following two substances: a second aluminum-containing species and the alkylated phenol compound; and removing the second aluminum-containing species from the second mixture by passing the second mixture through a first filter.

2. The method of claim 1, wherein the first mixture is heated to about 80 C. for a first period of time.

3. The method of claim 1, wherein after passing the second mixture through the first filter and thereby creating a filtered second mixture, the filtered second mixture is then passed through a filter.

4. The method of claim 1, wherein the first filter is rated at approximately 1 micron.

5. The method of claim 1, wherein the second mixture is heated to a temperature ranging from 80 C. to 300 C. for a second period of time before passing the second mixture through the first filter.

6. The method of claim 1, wherein the second mixture is heated to a temperature ranging from 100 C. to 200 C. for a second period of time before passing the second mixture through the first filter.

7. The method of claim 1, wherein the second mixture is heated to a temperature ranging from 120 C. to 150 C. for a second period of time before passing the second mixture through the first filter.

8. The method of claim 1, wherein the second mixture is heated to a temperature ranging from 40 C. to 200 C. for a second period of time before passing the second mixture through the first filter.

9. The method of claim 1, wherein the second mixture is heated to a temperature ranging from 70 C. to 150 C. for a second period of time before passing the second mixture through the first filter.

10. The method of claim 1, wherein the second mixture is heated to a temperature ranging from 80 C. to 90 C. for a second period of time before passing the second mixture through the first filter.

11. The method of claim 1, wherein the amount of water added to the first mixture ranges from 0.01 to 50% by weight of the first mixture.

12. The method of claim 1, wherein the amount of water added to the first mixture ranges from 0.01 to 10% by weight of the first mixture.

13. The method of claim 1, wherein the amount of water added to the first mixture ranges from 0.01 to 2% by weight of the first mixture.

14. The method of claim 1, wherein except for adding water, the method does not include the step of adding a dilute acid, a dilute base, or a salt to either the first mixture or the second mixture.

15. The method of claim 1, wherein the method does not include the step of separating mixtures by decanting.

16. The method of claim 1, wherein the method does not include the step of performing heat distillation on either the first mixture or second mixture.

17. The method of claim 2, wherein the filtered second mixture is then passed through a filter rated at approximately 1 micron.

18. A method comprising the steps: heating a first mixture to about 80 C. for a first period of time, wherein the first mixture contains the following two substances: a first aluminum-containing species and an alkylated phenol compound; after heating the first mixture to about 80 C. for a first period of time, adding water to the first mixture to thereby create a second mixture, wherein the second mixture contains the following two substances: a second aluminum-containing species and the alkylated phenol compound; heating the second mixture to at least 80 C. for a second period of time; and removing the second aluminum-containing species from the second mixture by passing the second mixture through a first filter.

19. A method comprising the steps: heating a first mixture to at least 80 C. for a first period of time, wherein the first mixture contains the following two substances: a first aluminum-containing species and an alkylated phenol compound; and after heating the first mixture to at least 80 C. for a first period of time, adding water to the first mixture to thereby create a second mixture, wherein the second mixture contains the following two substances: a second aluminum-containing species and the alkylated phenol compound.

20. The method of claim 19, wherein the amount of water added to the first mixture ranges from 0.01 to 10% by weight of the first mixture.

21. The method of claim 19, wherein deionized water is not used.

22. The method of claim 19, wherein this method does not include the step of decanting.

Description

BRIEF DESCRIPTION OF THE SEVERAL VIEWS OF THE DRAWING

[0019] FIG. 1 shows the general hydrolysis of active aluminum-containing catalyst species in alkylated phenolsynthesis where R is the alkyl/aryl group.

[0020] FIG. 2 shows aluminum hydroxide soluble complexes in dilute acidic solution.

[0021] FIG. 3 shows aluminum hydroxide soluble complexes in dilute base.

[0022] FIG. 4 shows aluminum hydroxide solubility in water.

DETAILED DESCRIPTION OF THE INVENTION

[0023] Embodiments are directed to a method for deactivating an aluminum-containing catalyst and then removing the deactivated aluminum-containing catalyst from a mixture containing the deactivated aluminum-containing catalyst and alkylated-phenol reaction products.

[0024] Embodiments include any combination of the following steps: [0025] 1. heating a first mixture to a temperature greater than 23 C. for a first period of time, wherein the first mixture contains the following two substances: a first aluminum-containing species and an alkylated-phenol compound; [0026] 2. after heating the first mixture to a temperature greater than 23 C. for a first period of time, adding water to the first mixture to thereby create a second mixture, wherein the second mixture contains the following two substances: a second aluminum-containing species and the alkylated-phenol compound; [0027] 3. heating the second mixture to a temperature greater than 80 C. for a second period of time; [0028] 4. after the second period of time, passing the second mixture through a first filter at least once.

[0029] The first aluminum-containing species can be any known aluminum-containing species. In embodiments, the aluminum containing species is:

##STR00001##

wherein R is an alkyl or aryl moiety.

[0030] The alkyl phenol compound found in both the first and second mixture can be any alkyl phenol compound. As a non-limiting example, the alkyl phenol compound can be 2,4 dicumylphenol.

[0031] In embodiments, the first mixture can be heated to a temperature greater than 23 C. for a first period of time. In embodiments, the first mixture can be heated to a temperature of at least 40 C. for a first period of time. In embodiments, the first mixture can be heated to a temperature of at least 80 C. for a first period of time. In embodiments, the first mixture can be heated to a temperature of about 80 C. for a first period of time.

[0032] In embodiments, the first period of time can be any period of time. In embodiments, the first period of time is approximately 10 seconds. In embodiments, the first period of time is approximately 30 seconds. In embodiments, the first period of time ranges from 1 to 10 minutes. In embodiments, the first period of time ranges from 5 to 25 minutes.

[0033] In embodiments, water is added to the first mixture in an amount ranging from 0.01 to 50% by weight of the first mixture. In embodiments, the amount of water added to the first mixture ranges from 0.01 to 10% by weight of the first mixture. In embodiments, the amount of water added to the first mixture ranges from 0.1 to 10% by weight of the first mixture. In embodiments, the amount of water added to the first mixture ranges from 0.5 to 2% by weight of the first mixture. In embodiments, the amount of water added to the first mixture ranges from 0.01 to 2% by weight of the first mixture.

[0034] In embodiments, the second aluminum-containing species is aluminum hydroxide:

##STR00002##

[0035] In embodiments, the second mixture is heated to a temperature of about 80 C. for a second period of time. In embodiments, the second mixture is heated to a temperature ranging from 80 C. to 300 C. for a second period of time. In embodiments, the second mixture is heated to a temperature ranging from 100 C. to 200 C. for a second period of time. In embodiments, the second mixture is heated to a temperature ranging from 120 C. to 150 C. for a second period of time.

[0036] In embodiments, the second period of time can be any period of time. In embodiments, the second period of time is approximately 20 minutes. In embodiments, the second period of time ranges from 10 to 30 minutes. In embodiments, the second period of time ranges from 15 to 25 minutes.

[0037] In embodiments, the second mixture is filtered at a temperature of about 80.0 C. In embodiments, the second mixture is filtered at a temperature ranging from 40.0 C. to 200.0 C.

[0038] In an embodiment, the second mixture is filtered at a temperature ranging from 70.0 C. to 150.0 C. In an embodiment, the second mixture is filtered at a temperature ranging from 80.0 C. to 90.0 C.

[0039] In embodiments, the second mixture is filtered using a filter rated at 1 micron. In embodiments, the second mixture is filtered using a filter rated at approximately 1 micron.

[0040] In embodiments, the second mixture is filtered only once. In embodiments, the second mixture is filtered twice. In embodiments where a second filtering occurs, the filter used for the second filtering is rated at 1 micron or approximately 1 micron.

[0041] In embodiments, other than water, this method does not add an acid, base, or salt to the first or second mixture. Embodiments do not include the step of separating mixtures by decanting. Embodiments do not include performing distillation.

EXAMPLES

Example 1

[0042] To a three-neck 500 mL flask equipped with a magnetic stirrer and connected to a condenser was added 320 g of 2, 4 dicumylphenol reaction mixture. The mixture was well mixed and heat was applied to a temperature of 80.0 C. When the mixture reached 80.0 C. 7.0 g of water was added to the flask. After 20 minutes, the material was filtered twice through a bag filter rated at 1 micron and 99% efficiency with samples taken after each filtration.

TABLE-US-00001 1.sup.st Filtration, % Al removal 1.8% 2.sup.nd Filtration, % Al removal 2.2% Color <100 APHA

Example 2

[0043] To a three-neck 500 mL flask equipped with a magnetic stirrer and connected to a condenser was added 320 g of 2, 4 dicumylphenol reaction mixture. The mixture was well mixed and heat was applied to a temperature of 80.0 C. When the mixture reached 80.0 C. 7.0 g of water was added to the flask. The mixture was then heated to 150 C. Once at 150.0 C. this temperature was held for 20 minutes. After 20 minutes, the set point was lowered to 90.0 C. Once at 90.0 C. the material was filtered twice through a bag filter rated at 1 micron and 99% efficiency with samples taken after each filtration.

TABLE-US-00002 1.sup.st Filtration, % Al removal 90.9% 2.sup.nd Filtration, % Al removal 96.6% Color <100 APHA

Example 3

[0044] To a three-neck 500 mL flask equipped with a magnetic stirrer and connected to a condenser was added 320 g of 2, 4 dicumylphenol reaction mixture. The mixture was well mixed and heat was applied to a temperature of 80.0 C. When the mixture reached 80.0 C. 7.0 g of water was added to the flask. The mixture was then heated to 150 C. Once at 150.0 C. this temperature was held for 20 minutes. After 20 minutes, the set point was lowered to 80.0 C. Once at 80.0 C. the material was filtered twice through a bag filter rated at 1 micron and 99% efficiency with samples taken after each filtration.

TABLE-US-00003 1.sup.st Filtration, % Al removal 95.1% 2.sup.nd Filtration, % Al removal 96.5% Color <100 APHA

Example 4

[0045] To a three-neck 500 mL flask equipped with a magnetic stirrer and connected to a condenser was added 320 g of 2, 4 dicumylphenol reaction mixture. The mixture was well mixed and heat was applied to a temperature of 80.0 C. When the mixture reached 80.0 C. 7.0 g of water was added to the flask. The mixture was then heated to 150 C. Once at 150.0 C. this temperature was held for 20 minutes. After 20 minutes, the set point was lowered to 70.0 C. Once at 70.0 C. the material was filtered twice through a bag filter rated at 1 micron and 99% efficiency with samples taken after each filtration.

TABLE-US-00004 1.sup.st Filtration, % Al removal 93.7% 2.sup.nd Filtration, % Al removal 96.3% Color <100 APHA

Example 5

[0046] To a three-neck 500 mL flask equipped with a magnetic stirrer and connected to a condenser was added 320 g of 2, 4 dicumylphenol reaction mixture. The mixture was well mixed and heat was applied to a temperature of 80.0 C. When the mixture reached 80.0 C. 7.0 g of water was added to the flask. The mixture was then heated to 130 C. Once at 130.0 C. this temperature was held for 20 minutes. After 20 minutes, the set point was lowered to 90.0 C. Once at 90.0 C. the material was filtered twice through a bag filter rated at 1 micron and 99% efficiency with samples taken after each filtration.

TABLE-US-00005 1.sup.st Filtration, % Al removal 90.4% 2.sup.nd Filtration, % Al removal 92.8% Color <100 APHA

Example 6

[0047] To a three-neck 500 mL flask equipped with a magnetic stirrer and connected to a condenser was added 320 g of 2, 4 dicumylphenol reaction mixture. The mixture was well mixed and heat was applied to a temperature of 80.0 C. When the mixture reached 80.0 C. 7.0 g of water was added to the flask. The mixture was then heated to 130 C. Once at 130.0 C. this temperature was held for 20 minutes. After 20 minutes, the set point was lowered to 80.0 C. Once at 80.0 C. the material was filtered twice through a bag filter rated at 1 micron and 99% efficiency with samples taken after each filtration.

TABLE-US-00006 1.sup.st Filtration, % Al removal 93.0% 2.sup.nd Filtration, % Al removal 93.5% Color <100 APHA

Example 7

[0048] To a three-neck 500 mL flask equipped with a magnetic stirrer and connected to a condenser was added 320 g of 2, 4 dicumylphenol reaction mixture. The mixture was well mixed and heat was applied to a temperature of 80.0 C. When the mixture reached 80.0 C. 7.0 g of water was added to the flask. The mixture was then heated to 130 C. Once at 130.0 C. this temperature was held for 20 minutes. After 20 minutes, the set point was lowered to 70.0 C. Once at 70.0 C. the material was filtered twice through a bag filter rated at 1 micron and 99% efficiency with samples taken after each filtration.

TABLE-US-00007 1.sup.st Filtration, % Al removal 93.7% 2.sup.nd Filtration, % Al removal 96.6% Color <100 APHA

Example 8

[0049] To a three-neck 500 mL flask equipped with a magnetic stirrer and connected to a condenser was added 320 g of 2, 4 dicumylphenol reaction mixture. The mixture was well mixed and heat was applied to a temperature of 80.0 C. When the mixture reached 80.0 C. 3.0 g of water was added to the flask. The mixture was then heated to 130 C. Once at 130.0 C. this temperature was held for 20 minutes. After 20 minutes, the set point was lowered to 90.0 C. Once at 90.0 C. the material was filtered twice through a bag filter rated at 1 micron and 99% efficiency with samples taken after each filtration.

TABLE-US-00008 1.sup.st Filtration, % Al removal 93.1% 2.sup.nd Filtration, % Al removal 93.6% Color <100 APHA

Example 9

[0050] To a three-neck 500 mL flask equipped with a magnetic stirrer and connected to a condenser was added 320 g of 2, 4 dicumylphenol reaction mixture. The mixture was well mixed and heat was applied to a temperature of 80.0 C. When the mixture reached 80.0 C. 3.0 g of water was added to the flask. The mixture was then heated to 130 C. Once at 130.0 C. this temperature was held for 20 minutes. After 20 minutes, the set point was lowered to 80.0 C. Once at 80.0 C. the material was filtered twice through a bag filter rated at 1 micron and 99% efficiency with samples taken after each filtration.

TABLE-US-00009 1.sup.st Filtration, % Al removal 93.4% 2.sup.nd Filtration, % Al removal 94.6% Color <100 APHA

Example 10

[0051] To a three-neck 500 mL flask equipped with a magnetic stirrer and connected to a condenser was added 320 g of 2, 4 dicumylphenol reaction mixture. The mixture was well mixed and heat was applied to a temperature of 80.0 C. When the mixture reached 80.0 C. 3.0 g water was added to the flask. The mixture was then heated to 130 C. Once at 130.0 C. this temperature was held for 20 minutes. After 20 minutes, the set point was lowered to 70.0 C. Once at 70.0 C. the material was filtered twice through a bag filter rated at 1 micron and 99% efficiency with samples taken after each filtration.

TABLE-US-00010 1.sup.st Filtration, % Al removal 94.6% 2.sup.nd Filtration, ppm Al 95.2% Color <100 APHA

Example 11

[0052] To a three-neck 500 mL flask equipped with a magnetic stirrer and connected to a condenser was added 320 g of 2, 4 dicumylphenol reaction mixture. The mixture was well mixed and heat was applied to a temperature of 80.0 C. When the mixture reached 80.0 C. 1.0 g water was added to the flask. The mixture was then heated to 130 C. Once at 130.0 C. this temperature was held for 20 minutes. After 20 minutes, the set point was lowered to 90.0 C. Once at 90.0 C. the material was filtered twice through a bag filter rated at 1 micron and 99% efficiency with samples taken after each filtration.

TABLE-US-00011 1.sup.st Filtration, % Al removal 93.2% 2.sup.nd Filtration, % Al removal 94.5% Color <100 APHA

Example 12

[0053] To a three-neck 500 mL flask equipped with a magnetic stirrer and connected to a condenser was added 320 g of 2, 4 dicumylphenol reaction mixture. The mixture was well mixed and heat was applied to a temperature of 80.0 C. When the mixture reached 80.0 C. 1.0 g water was added to the flask. The mixture was then heated to 120 C. Once at 120.0 C. this temperature was held for 20 minutes. After 20 minutes, the set point was lowered to 90.0 C. Once at 90.0 C. the material was filtered through a bag filter rated at 1 micron and 99% efficiency.

TABLE-US-00012 1.sup.st Filtration, % Al removal 91.6% Color <100 APHA

Example 13

[0054] To a three-neck 500 mL flask equipped with a magnetic stirrer and connected to a condenser was added 320 g of 2, 4 dicumylphenol reaction mixture. The mixture was well mixed and heat was applied to a temperature of 80.0 C. When the mixture reached 80.0 C. 1.0 g water was added to the flask. The mixture was then heated to 110 C. Once at 110.0 C. this temperature was held for 20 minutes. After 20 minutes, the set point was lowered to 90.0 C. Once at 90.0 C. the material was filtered through a bag filter rated at 1 micron and 99% efficiency.

TABLE-US-00013 1.sup.st Filtration, % Al removal 88.4% Color <100 APHA

Example 14

[0055] To a three-neck 500 mL flask equipped with a magnetic stirrer and connected to a condenser was added 320 g of 2, 4 dicumylphenol reaction mixture and 0.032 g aluminum (100 ppm). The mixture was well mixed and heat was applied to a temperature of 80.0 C. When the mixture reached 80.0 C. 3.0 g water was added to the flask. The mixture was then heated to 130.0 C. Once at 110.0 C. this temperature was held for 20 minutes. After 20 minutes, the set point was lowered to 90.0 C. Once at 90.0 C. the material was filtered through a bag filter rated at 1 micron and 99% efficiency.

TABLE-US-00014 1.sup.st Filtration, % Al removal 84.9% Color <100 APHA

Example 15

[0056] To a three-neck 500 mL flask equipped with a magnetic stirrer and connected to a condenser was added 320 g of 2, 4 dicumylphenol reaction mixture and 0.064 g aluminum (200 ppm). The mixture was well mixed and heat was applied to a temperature of 80.0 C. When the mixture reached 80.0 C., 3.0 g water was added to the flask. The mixture was then heated to 130.0 C. Once at 110.0 C. this temperature was held for 20 minutes. After 20 minutes, the set point was lowered to 90.0 C. Once at 90.0 C. the material was filtered through a bag filter rated at 1 micron and 99% efficiency.

TABLE-US-00015 1.sup.st Filtration, % Al removal 75.1% Color <100 APHA