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Alkylated Naphthalenes #729151
05/01/05 01:22 AM
05/01/05 01:22 AM
Joined: Jun 2002
Posts: 19,494
Iowegia - USA
MolaKule Offline OP
MolaKule  Offline OP
Joined: Jun 2002
Posts: 19,494
Iowegia - USA
Alkylated Naphthalenes ( AN's)
By MolaKule


Alkylated Naphthalenes (AN’s) or”alkylnaphthalenes” are a class of fluids of “alkylated aromatics” and were first developed as Pour Point Depressants (PPD’s) in mineral oils. These were made by reacting alkylating agents with naphthalenes and suitable catalysts.

Another alkylated aromatic that has previously been used in manual transmission lubes are the alkylated benzenes.

As such, the AN’s fall into the Group V base oil category.

From the latest literature, there are about 20 or more different approaches to producing AN’s. In one patent application, the AN is” The hydrocarbyl aromatic is…..alkylated naphthalene (primarily mono-alkylated) having a kinematic viscosity of approximately 4.6 cSt at 100.degree. C. The primarily mono-alkylated naphthalene is prepared by the alkylation of naphthalene with an olefin primarily comprised of 1-hexadecene.”

Today, the AN’s are being used as partial replacements for esters in fully formulated synthetic and mineral based PCMO and diesel motor oils.

From the most recent patent literature, companies such as Exxon Mobil are currently using an olefinic methylnaphthalenes such as is described in this and previous patents:

http://appft1.uspto.gov/netacgi/nph-Parser?Sect1=PTO2&Sect2=HITOFF&u=%2Fnetahtml%2FPTO%2Fsearch-adv.html&r=56&f=G&l=50&d=PG01&s1=%22alkylated+naphthalenes%22&p=2&OS="alkylated+naph thalenes"&RS="alkylated+naphthalenes"

It is believed that these “higher” naphthalenes exhibit better thermal and oxidative stability than previous AN's.

From another patent application, the new Blends may be composed of, “One of ordinary skill in the art would easily note that these findings may be extended to any paraffinic base stock. The inventors note that this discovery may also employ Group III base stocks, and preferably Gas-to-Liquids or Fischer-Tropsch base stocks. Thus, as an non-limiting illustrative sample, the inventors also note that a mixture of about 30 wt % Group III base stock, about 30 to 40% PAO, about 2 wt % Trimethylolpropane and about 5 to 40 wt % Hydrocarbyl Aromatics, with the remainder being a Performance Additive package will also achieve the same surprising Fuel Economy increases.”

So some new formulations may be incorporating AN’s as well as eters in their GroupIII formulations.

[ May 01, 2005, 05:35 PM: Message edited by: MolaKule ]

Re: Alkylated Naphthalenes #729152
05/01/05 02:17 AM
05/01/05 02:17 AM
Joined: Dec 2003
Posts: 7,409
Austin, TX
427Z06 Offline
427Z06  Offline
Joined: Dec 2003
Posts: 7,409
Austin, TX
For some time I suspected that these new Alkylated Naphthalenes were substitued for ester basestocks in Mobil's latest "SuperSyn" synthetic motor oils. I.e. Mobil's latest "SuperSyn" synthetic motor oils are composed of their regular PAO, SuperSyn PAOs and Alkylated Naphthalenes as opposed to the Tri-Syn formula that was mainly composed of their regular PAO, esters and some smaller percentage of something else. Am I way off base here? [I dont know]

Re: Alkylated Naphthalenes #729153
05/01/05 02:41 AM
05/01/05 02:41 AM
Joined: Jun 2002
Posts: 19,494
Iowegia - USA
MolaKule Offline OP
MolaKule  Offline OP
Joined: Jun 2002
Posts: 19,494
Iowegia - USA
In the Tri-Syn formulation that something else was Alkylated Naphthalenes.

Let's hope the methylated version of their AN's are better than the AN's in their Tri-syn formulas.

Re: Alkylated Naphthalenes #729154
05/01/05 02:55 AM
05/01/05 02:55 AM
Joined: Oct 2004
Posts: 5,799
Texas, Mentone for work, Galve...
Bryanccfshr Offline
Bryanccfshr  Offline
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Texas, Mentone for work, Galve...
Thanks Molakule,
I am going to have to read it all, especially the patent language, a dozen times to digest it.

It seems there are more ways to formulate a PCMO than I had imagined.

Re: Alkylated Naphthalenes #729155
05/01/05 04:28 AM
05/01/05 04:28 AM
Joined: Nov 2002
Posts: 30,919
NJ
buster Offline
buster  Offline
Joined: Nov 2002
Posts: 30,919
NJ
Thanks Molakule, I've been curious about AN's. I wonder how they impact volatility? For instance, M1 GF-3 5w-30 had a Noak of 8.9% or something around there. Many experience high volatility with that oil. Should AN's help reduce volatility? And with the additional 50% SuperSyn in the new EP oils, does that mean 50% more PAO is used rather then AN's?

Re: Alkylated Naphthalenes #729156
05/01/05 04:59 AM
05/01/05 04:59 AM
Joined: Jun 2002
Posts: 19,494
Iowegia - USA
MolaKule Offline OP
MolaKule  Offline OP
Joined: Jun 2002
Posts: 19,494
Iowegia - USA
quote:
I wonder how they impact volatility? For instance, M1 GF-3 5w-30 had a Noak of 8.9% or something around there. Many experience high volatility with that oil. Should AN's help reduce volatility? And with the additional 50% SuperSyn in the new EP oils, does that mean 50% more PAO is used rather then AN's?

Remember people, this is a patent application, and it DOES NOT MEAN they are using this formulation AT THE PRESENT TIME. These companies file patents all the time to protect future formulations and processes.

If they use the 8 cSt version and a high viscosity PAO, the volatility might be reduced, but not with the 4.6 cSt stuff.

Who knows what the vague language in the last part of their ad sentence really means.

Re: Alkylated Naphthalenes #729157
05/01/05 05:26 AM
05/01/05 05:26 AM
Joined: Apr 2004
Posts: 7,819
New York
pbm Offline
pbm  Offline
Joined: Apr 2004
Posts: 7,819
New York
Molakule: When I first used Mobil 1 it was Advanced Formula SH, followed by Advanced Formula SJ. When Tri-Syn came out I just assumed it was an improvement (because Mobil said it was.) When SS came out I again assumed (because again Mobil said) it was a better product. I am now wondering if the old Advanced Formula really was the superior product and that the changes were to keep
the price down. What do you think? What was the makeup of AF if you know? Thanks.

Re: Alkylated Naphthalenes #729158
05/01/05 06:10 AM
05/01/05 06:10 AM
Joined: Nov 2002
Posts: 30,919
NJ
buster Offline
buster  Offline
Joined: Nov 2002
Posts: 30,919
NJ
It would makes sense to me that any large oil company/producer would try and improve formulations but also reduce costs while doing so. Companies like Redline and Molekule's company are out to make the best regardless of price. Like Molekule said, it's pure speculation at this point whether these are being used and to what extent. Interesting stuff regardless. [Cheers!]

Re: Alkylated Naphthalenes #729159
05/01/05 06:11 AM
05/01/05 06:11 AM
Joined: Jun 2003
Posts: 278
Petersburg, West Virginia
like a rock Offline
like a rock  Offline
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Posts: 278
Petersburg, West Virginia
Well what could be in the new EP version of M-1 that causes oil consumption. My 2004 dodge dakota v-6 never used any oil. With only 14000 miles on the truck I switched to the new ep version and was on a 300 mile trip this weekend and the truck used a half quart of oil. This is the 5w-30 in the crankcase and the trip was at speeds up to the legal limits of around 70 mph. I do not want to blame the oil because the motor seems to produce better power with this oil and does get better gas mileage also. [I dont know]

Re: Alkylated Naphthalenes #729160
05/01/05 06:43 AM
05/01/05 06:43 AM
Joined: Nov 2002
Posts: 30,919
NJ
buster Offline
buster  Offline
Joined: Nov 2002
Posts: 30,919
NJ
quote:
Well what could be in the new EP version of M-1 that causes oil consumption. My 2004 dodge dakota v-6 never used any oil. With only 14000 miles on the truck I switched to the new ep version and was on a 300 mile trip this weekend and the truck used a half quart of oil. This is the 5w-30 in the crankcase and the trip was at speeds up to the legal limits of around 70 mph. I do not want to blame the oil because the motor seems to produce better power with this oil and does get better gas mileage also.
It should subside. Very normal for a spike in oil consumption to occur when changing oils. RL in particular causes this to happen. Nothing to worry aobut.

Re: Alkylated Naphthalenes #729161
02/21/06 11:03 PM
02/21/06 11:03 PM
Joined: Jun 2002
Posts: 19,494
Iowegia - USA
MolaKule Offline OP
MolaKule  Offline OP
Joined: Jun 2002
Posts: 19,494
Iowegia - USA
BTW, Alkylated Naphthalenes (AN's) do not provide any cost or tribological advantage over esters IMHO. Currently, they are almost as expensive as esters.

The only advanatge of Alkylated Naphthalenes (AN's) over esters is that AN's would have slightly better additive solvency for PAO formulations and thus the amount of dispersant could be reduced.

After doiong my own testing, I am not convinced that complex POE's suffer any hydrolitic stability problems.

Re: Alkylated Naphthalenes [Re: buster] #4671327
02/19/18 07:40 PM
02/19/18 07:40 PM
Joined: Sep 2010
Posts: 7,481
Texas & Global
4WD Offline
4WD  Offline
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Posts: 7,481
Texas & Global
Originally Posted By: buster
Thanks Molakule, I've been curious about AN's. I wonder how they impact volatility? For instance, M1 GF-3 5w-30 had a Noak of 8.9% or something around there. Many experience high volatility with that oil. Should AN's help reduce volatility? And with the additional 50% SuperSyn in the new EP oils, does that mean 50% more PAO is used rather then AN's?


When you say “many experienced high volatility” ~ exactly how is that diagnosed?


2018 Chevy 1500 Z71 4WD
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Re: Alkylated Naphthalenes [Re: MolaKule] #4671337
02/19/18 07:43 PM
02/19/18 07:43 PM
Joined: Sep 2010
Posts: 7,481
Texas & Global
4WD Offline
4WD  Offline
Joined: Sep 2010
Posts: 7,481
Texas & Global
Originally Posted By: MolaKule
BTW, Alkylated Naphthalenes (AN's) do not provide any cost or tribological advantage over esters IMHO. Currently, they are almost as expensive as esters.

The only advanatge of Alkylated Naphthalenes (AN's) over esters is that AN's would have slightly better additive solvency for PAO formulations and thus the amount of dispersant could be reduced.

After doiong my own testing, I am not convinced that complex POE's suffer any hydrolitic stability problems.


What if there was a higher external market value for Esterex … would they sell to formulators and use the AN at BPT to blend thier stuff?


2018 Chevy 1500 Z71 4WD
2017 Chevy Tahoe LT 4WD
2014 Fusion Hybrid Titanium
2013 Cruze LTZ - RS Turbo
Re: Alkylated Naphthalenes [Re: 4WD] #4672047
02/20/18 03:07 PM
02/20/18 03:07 PM
Joined: Jun 2002
Posts: 19,494
Iowegia - USA
MolaKule Offline OP
MolaKule  Offline OP
Joined: Jun 2002
Posts: 19,494
Iowegia - USA
Originally Posted By: 4WD
Originally Posted By: MolaKule
BTW, Alkylated Naphthalenes (AN's) do not provide any cost or tribological advantage over esters IMHO. Currently, they are almost as expensive as esters.

The only advanatge of Alkylated Naphthalenes (AN's) over esters is that AN's would have slightly better additive solvency for PAO formulations and thus the amount of dispersant could be reduced.

After doiong my own testing, I am not convinced that complex POE's suffer any hydrolitic stability problems.


What if there was a higher external market value for Esterex … would they sell to formulators and use the AN at BPT to blend thier stuff?


As I said I shy away from AN's but some of my customers want some AN (not supplied by Mobil) included because of the Advertising hype so I include it to satisfy their itch. For full synthetic formulations I still insist on including esters even if AN's are requested.

Last edited by MolaKule; 02/20/18 03:08 PM.

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