Even before I purchased my 1982 Mercedes 380 SL in 2014, I had changed oil many, many times on my cars. And indeed, one of the first things I did after getting the car home was change fluids, including oil. My first time on this car must of been not eventful, as I do not remember anything about doing it. However, I must have noticed the rather antiquated oil filter system that was on this car. Antiquated and over engineered. Much later -- perhaps in 2024 -- I ran into big trouble doing an oil change.
I usually get my Mann filter from Rock auto and it comes with a rubber sealing gasket, a drain plug copper gasket, and two small gaskets to use on the center bolt. Often the filters come two ended, so make sure that the larger diameter hole is the one you use to push up to the filter assembly on the block
Anyway, on one fateful day I drained the oil, removed the filter with a 17 mm socket, and then put the whole thing back together. I suffer from brain fog (I guess that is what it is) in old age, and promptly cross-threaded the bolt into a metal connector that screws into the block housing. I didn't quite realize what I had done, filled up the car with 9 quarts of oil, and started the car up.
9 quarters gushed on to the driveway - I major problem for weeks, and I set off a search for both chemicals to get the oil off the concreate and a new connector. The connector was not easy to find. Not on Ebay. Not on online parts suppliers. Finally, I visited Gina at Bob Ross Mercedes and she found one for about $30, as I recall.
The problem was getting the old adapter -- the thing that the long bolt screws in to. First, I needed a 32mm 12 point socket. With a ratchet and even small breaker bar, the adapter did not move! So then my friend Cliff got under the car pushed the socket at short breaker bar up to ensure a good fit, and I used the handle off my hydraulic jack to try to turn it. Only after I leaned on it did it move, with a loud "crack!" I thought I broke to socket, but actually we succeeded in getting the adapter to move. The rest was routine. But I did use tide, other detergents, and chemicals I no longer recall cleaning off the driveway that for a time was both an embarrassment and testimony to folly.

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