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PEH, Coldwar,
A couple of hints that helped me with the oil filter on the '68 220D I drove for 20 years. When putting it all together, I sat the can down over the bolt on a flat level place on the floor or a work bench. Then proceeded to load all of the parts back into the can. Once all is inside, you can place the assembly up against the filter case head tightly and start the bolt into the hole. Once the bolt is started you can relax your grip on the can and use the bolt to pull it all together. Just before the big 'O' ring seats, push the can back up and make sure it is accurately seated and complete the bolt tightening.
On the oil draining part of the job, I always loosened up the center bolt a few turns, but not so much that it came out of the head. Then you can hold the can up and the oil will drain out around the bolt but below where you are holding and into a drain pan or whatever you have provided. 20 years of doing it provided a lot of practice!!
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1961 190Db retired
1968 220D/8 325,000
1983 300D 164,150
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