OK, my 1983 380SEl has been leaking oil out the left cylinder head for about five years and it has finally gotten to the point that it is leaking about 1 quart every 500 miles if I drive around tow.
The funny thing, if I drive it on a highway trip the oil leak near stops! I've ordered all the parts.
I intend on doing the timing chain (already a double chain), all the guides, head gaskets on both sides, and totally reseal the entire upper half and front of the engine.
I've already purchased three special hex key sockets to remove the cylinder head bolts.
My question is, what problems may arise in this venture? I've heard of broken head bolts and stripped head bolt holes in the block.
I'm reusing my original bolts due to the fact that the Mercedes does not use torque to yield bolts.
I'm a Ford mechanic and this is my first major repair on old Janis (the cars name).
If anyone can offer any advice I'm open to hearing.
I just want to get my baby back on the road leak free! This has been the best car I've ever had.
She has 225000 miles on her and she still looks like new although the seats are starting to show there age.

Perhaps because V8 head gasket problems are so rare.

I did mine about 2 years back on my 82, I encountered no problem with any bolts stripping out, but I had heard the same thing. I also converted mine over to double row at the same time, did the valve job on the heads as well and overhauled the transmission.

...and thats where it still sits today. Just the block and the heads on it. Someday I'll get time to finish reassembling it and put it back in the car. Too many projects...

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1980 500SE/AMG Euro
1981 500SEL Euro
1982 380SEL
1983 300TD
1983 500SEC/AMG Euro
1984 500SEC
1984 300TD Euro
1986 190E 2.3-16
1986 190E 2.3
1987 300D
1997 C36 AMG
2003 C320T 4matic

past: 1969 280SE 4.5 | 1978 240D | 1978 300D | 1981 300SD | 1981 300SD | 1982 300CD | 1983 300CD | 1983 300SD | 1983 380SEC | 1984 300D | 1984 300D | 1984 300TD | 1984 500SEL | 1984 300SD | 1985 300D | 1986 300E | 1986 560SEL | 1986 560SEL/Carat | 1987 560SEC | 1991 300D 2.5 | 2006 R350

I did not figure the bolts would be a problem. I will find out tomorrow though. Deanyel obviously does not have much experience with the 116 engines and the leaky left heads. But thanks for the input.

Nor do other people - that was the point.

Never mind the head bolts...I stripped one of the allens (the head not the threads) holding the generator assembly onto the block last night. 20 year old bolts don't like to move. Why did MB use allen heads on the alternator brackets and hex heads on the PS brscket? My chain guide pins don't like to move either...I have tried the bolt and washer method but I don't think they make a M6 bolt strong enough...may have to break down and but the $50 tool.

Good luck w/ your project. I think if you work on it as a hobby it will be fun but if you put a time limit on it and need that car running by a certain time it'll become stressful. Enjoy!

I did this job about 3 months ago on my 560SL. It's a 117 engine but should be the same. When you do this, expect to replace every vacume line under the manifold and all the rubber vacume elbows. I also overhauled the intake manifold and replaced all seals. Since the vacume lines are color coded and you can only purchase pure white replacement line, I color coded mine with colored shink tube. When I pulled the manifold off I damaged the rubber boot connecting the airflow sensor to the throttle body. That was about a $60.00 part. Also the clamp that connects the rubber boot to the throtle body is a two pice clamp. You order the band and the clamping mechinism as seperate parts.

I heard all the stories about striped out bolt but it did not happen to me. They all torqued up just fine. I replaced the leaking left head gasket and retorqued the right head. On some of the right head bolts I did get almost 1/4 turn additional from the point wher the bolt started. Therefore I will retorque my left head next year after I get a few miles on it just so that this doesent happen again. I will admit it is kind of scary retorquing. It will be the third time torque will be being applied to those aluminum threads.

If the cylinder head bolt should strip out, my plan was to buy a set of junk yard heads drill them and sleave them to the proper size for the helicoil kit drill size, insted of buying the $1600.00 tool drill plate. Warning the bolts that go through the cam bearings are at a slight angle from perpendiculare to the head.

I would highly recomend you get the 380SL Repiar CD before you start. It is typically about $100.00 online or $10.00 for a bootleg copy on ebay.

Things you should order before you start the job are:

1) Head gasket set
2) Intake manifold ring seals
3) Injector seals
4) Throttle body gasket
5) 10 meters of nylon vacume tube (replaces all tubing under the hood)
6) 1 meter of rubber vacume tube.
7) An assortment of Vacume Elbows
8) There is one vacume elbow attached to the throttle body which is an odd ball I was not able to find it on line. If I recal it goes to the charcole canister. I ordered mine from a local MB dealer after bring down the old one.
9) Airflow sensor rubber mounting isolators.
10) Throtel body to rubber boot clamp (Both pieces)
11) A water bypass hoes. You have to buy 1 meter and use about 2" of it.
12) A water outlet gasket
13) Valve cover gaskets
14) Cam oiler plastic fittings
15) Timing Chain and spare link (If you find a peaned over one let me know where you got it.)
16) 3 chain guides
17) 4 chain guide pins
18) Chain Tensioner if required
19) Since you will have the exhaust manifolds off it is a good time to replace the engine mounts. Use genuine MB mounts or nothing.
20) I also recomend you getting the pin pulling tools and the chain installer tool. The last guy that used a washer proceedure I gave him ended up taking it to the shop to finish the job.

A trick I used to get the exhaust manifolds back on is I got four 8mm bolts about 60mm long and cut the heads off them. I placed these finger tight in the cylinder head upper exhaust outlet holes and the standard studs in the lower holes. I then sliped the gaskets onto these bolts and the cutoff bolts served as a tool to hold the gaskets in place untill you got enough torque on the lower studs to clamp the gaskets in place then the cutoff bolts can be removed and replaced with the normal bolts.

The job is straight forward just like a Ford V8.
1) Start by disconnecting the batery.
2) Remove the fuel cooler lines going to AC line (Might not have this on a 380SL)
3) You will have to disconect the exhaust, remove the engine mount bolts and jack one side up at a time to get at the lower exhaust manifold bolts.
4) Remove the exhaust manifolds. The EGR tube comes out with the intake manifold.
5) Drain water from radiator and block using drain plugs on both forward sides of engine
6) Remove the power stearing pump, Alternator and distributor
7) Remove the tiny bolt on the back of the left head that supports the EGR tube. You will have lots of fun putting it back in later.
8) Remove all injector lines and injectors.
9) Remove the intake manifold with EGR tube attached
10) Remove came oiler tubes
11) Remove head bolts and remove head. Carful some of the bolts that look like head bolts only hold in the cam bearings.
12) Inspect heads and repair as required (mine needed nothing)
13) Clean out all EGR ports on head and manifold and also the head thats still in the car
14) Clean out vally under the intake manifold.
15) Clean all gasket surfaces (take your time with this)
16) Put it all back together and check for fuel leaks and oil leaks.
17) Dont forget that little EGR tube clamp bolt in the back of the left cylinder head.
18) I am sure there is a bunch of stuff I missed like removing the vacume line to the power booster or transmission. This is why I recommend getting the CD.

I used 20 ft-lb on the intake manifold bolts there is no torque value listed in the manual.

Thank you Roncallo for such a nice reply.
I started on it yesterday and got the left head off and am starting on the right side.
I'm going to go ahead and pull the timing cover as well and replace the guides under there as well as the oil pump chain and guide.
Everything has went well except for one bolt (probably the same one another poster was telling me about) on the right cylinder head that the cruise control servo is mounted to refuses to move.
I eventually stripped the Allen head out of it but I guess it's time to move on to vice grips and other means of force.
I started not to do the lower end guides but it has been like 150,000 miles since the chain was replaced so I figured it would be cheap insurance to go ahead and replace them all.
The head gasket leak was fairly visible once I got the head off and looked at the gasket.
You could see where it had lost it's seal near the large oil galley. Overall, the project has been relatively simple.
The hardest thing to date was removing the intake manifold.
And the boot below the air flow meter was busted (evidently not all the way) so I'm going to replace it while I'm in there as well as most of those vacuum lines.

Anyone ever replaced that boot under the air flow sensor?
I will only need the boot and not the boot and flange mount because my engine number is below the engine number that requires both pieces.
Thank God! Both pieces are like $200.00! Well, I guess it will be a day or two before I get back to working on her, I'm waiting on this Hurricane to pass over (or the remnants of it). I've got to get outside and pick up any small loose object that may blow away! Cheers!

That is the same boot I broke on my car. I just needed the boot it was about $60.00 dont forget to get a new clamp you have to order the strap and tightening mechanism seperatly. Good to see it's going well.

John Roncallo