# US 4,399,301 A · Methylenically-substituted undecadienes

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- Number: US 4,399,301 A
- Document ID: US4399301A
- Status: Granted
- Kind: A
- Application number: 06/075,216
- Filed: 1979-09-13
- Granted: 1983-08-16
- Earliest claimed: 1978-09-15
- Assignees: Rhone-Poulenc Industries
- Inventors: Didier Morel
- Web page: https://patentgrep.com/patent/US4399301A

## CPC

- C07C 29/46: by diene-synthesis
- C07C 33/02: Acyclic alcohols with carbon-to-carbon double bonds
- C07C 41/30: by increasing the number of carbon atoms, e.g. by oligomerisation
- C07C 43/15: containing only non-aromatic carbon-to-carbon double bonds
- C07C 69/007: Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
- C07C 69/145: of unsaturated alcohols
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Methylenically-substituted undecadiene compounds having the structural formula: ##STR1## wherein X is selected from the group consisting of lower acyloxy, aryloxy having from 6 to 14 carbon atoms, lower alkoxy and hydroxy, and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15 and R.sub.16 are independently selected from the group consisting of hydrogen and lower alkyl, with the proviso that at least one of R.sub.3, R.sub.5 and R.sub.6 and at least one of R.sub.9, R.sub.10, R.sub.11 and R.sub.12 must be hydrogen, are prepared by reacting a diene having the structural formula: ##STR2## with a conjugated diene having the structural formula: ##STR3## in the presence of a rhodium/trivalent phosphorus catalyst, with the atomic ratio of the trivalent phosphorus to the rhodium therein being at least 1.5. The compounds can be hydrogenated and saponified to form known alcohols which are precursors for biodegradable detergents.

## Claims

### Claim 1

A methylenically-substituted undecadiene compound having the structural formula: ##STR24## wherein X is selected from the group consisting of lower acyloxy, aryloxy having from 6 to 14 carbon atoms, lower alkoxy and hydroxy, and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15 and R.sub.16 are independently selected from the group consisting of hydrogen and lower alkyl, with the proviso that at least one of R.sub.3, R.sub.5 and R.sub.6 and at least one of R.sub.9, R.sub.10, R.sub.11 and R.sub.12 must be hydrogen.

### Claim 2 (depends on 1)

The compound of claim 1 wherein the lower alkyl contains from 1 to about 3 carbon atoms.

### Claim 3 (depends on 1)

The compound of claim 1 wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15 and R.sub.16 are independently selected from the group consisting of hydrogen and methyl.

### Claim 4 (depends on 1)

The compound of claim 1 wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15 and R.sub.16 are hydrogen.

### Claim 5 (depends on 1)

The compound of claim 1 wherein X is an acyloxy.

### Claim 6 (depends on 5)

The compound of claim 5 wherein X is acetoxy.

### Claim 7 (depends on 1)

The compound of claim 1 wherein X is an aryloxy.

### Claim 8 (depends on 1)

The compound of claim 1 wherein X is an alkoxy.

### Claim 9 (depends on 8)

The compound of claim 8 wherein X is methoxy.

### Claim 10 (depends on 1)

The compound of claim 1 which has the structural formula: ##STR25##