# US 4,395,578 A · Oligomerization of olefins over boron trifluoride in the presence of a transition metal cation-containing promoter

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- Number: US 4,395,578 A
- Document ID: US4395578A
- Status: Granted
- Kind: A
- Application number: 06/389,738
- Filed: 1982-06-18
- Granted: 1983-07-26
- Earliest claimed: 1982-06-18
- Assignees: Texaco Inc.
- Inventors: John M. Larkin
- Web page: https://patentgrep.com/patent/US4395578A

## CPC

- C07C 2/26: with hydrides or organic compounds (C07C2/20 takes precedence)
- B01J 27/12: Fluorides
- C07C 2/20: Acids of halogen; Salts thereof {; Complexes thereof with organic compounds}
- C07C 2/22: Metal halides; Complexes thereof with organic compounds
- C10M 107/02: Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
- C07C 2523/26: Chromium
- C07C 2523/72: Copper
- C07C 2523/755: Nickel
- C07C 2527/1213: Boron fluoride
- C07C 2527/128: Compounds comprising a halogen and an iron group metal or a platinum group metal
- C07C 2527/232: Carbonates
- C07C 2531/02: containing organic compounds or metal hydrides
- C07C 2531/04: containing carboxylic acids or their salts
- C10M 2205/00: Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33)

## Abstract

Alpha olefins may be oligomerized over a boron trifluoride catalyst and a promoter containing a transition metal cation. When the oligomers are hydrogenated they provide a synthetic lubricant base stock having excellent properties. The alpha olefins may be derived from ethylene polymerization or wax pyrolysis. A protonic promoter and an inert organic solvent may be present.

## Claims

### Claim 1

A process for oligomerizing mono olefins comprising contacting a mixture of alpha mono olefins having between 3 and 18 carbon atoms, inclusive, with a catalyst comprising boron trifluoride in the presence of an inorganic promoter containing a transition metal cation, under oligomerization conditions.

### Claim 2 (depends on 1)

The process of claim 1 in which the mixture of alpha mono olefins consists essentially of low molecular weight alpha olefins having 3 to 5 carbon atoms and higher molecular weight alpha olefins having 8 to 18 carbon atoms.

### Claim 3 (depends on 1)

The process of claim 1 in which the catalyst is present in an amount of from 0.2 to 3.0 weight percent.

### Claim 4 (depends on 1)

The process of claim 1 in which the inorganic promoter contains a transition metal cation selected from the group consisting of nickel, copper, cobalt and chromium.

### Claim 5 (depends on 4)

The process of claim 4 in which the inorganic promoter is selected from the group consisting of elemental nickel, elemental copper, nickel oxide, copper oxide, chromium oxide, nickel fluoride, cobaltous carbonate, cobaltous fluoride, and cobalt tetrafluoroborate, and mixtures thereof.

### Claim 6 (depends on 1)

The process of claim 1 in which the inorganic promoter is present in an amount of from 0.005 to 3.0 weight percent.

### Claim 7 (depends on 1)

The process of claim 1 in which a protonic promoter is employed in connection with the catalyst, the promoter being selected from the group consisting of alcohols carboxylic acids and water.

### Claim 8 (depends on 7)

The process of claim 7 in which the protonic promoter is 1-butanol.

### Claim 9 (depends on 1)

The process of claim 1 in which less than 30 weight percent of an inert organic solvent is employed.

### Claim 10 (depends on 1)

The process of claim 1 in which the oligomerization reaction is conducted at a temperature in the range of about 25.degree. to 125.degree. C. and a pressure that is autogenous.

### Claim 11 (depends on 1)

The process of claim 1 in which the oligomerized olefins are subsequently hydrogenated.

### Claim 12

A process for oligomerizing mono olefins comprising contacting a mixture of alpha mono olefins which consists essentially of low molecular weight alpha olefins having 3 to 5 carbon atoms and higher molecular weight alpha olefins having 8 to 18 carbon atoms, with a catalyst comprising boron trifluoride in the presence of an inorganic promoter containing a transition metal cation selected from the group consisting of nickel, copper, cobalt and chromium.

### Claim 13 (depends on 12)

The process of claim 12 in which the catalyst is present in an amount of from 0.2 to 3.0 weight percent.

### Claim 14 (depends on 12)

The process of claim 12 in which the inorganic promoter is selected from the group consisting of elemental nickel, elemental copper, nickel oxide, copper oxide, chromium oxide, nickel fluoride, cobaltous carbonate, cobaltous fluoride and cobalt tetrafluoroborate, and mixtures thereof.

### Claim 15 (depends on 12)

The process of claim 12 in which the inorganic promoter is present in an amount of from 0.005 to 3.0 weight percent.

### Claim 16 (depends on 12)

The process of claim 12 in which a protonic promoter is employed in connection with the catalyst, the promoter being selected from the group consisting of alcohols, carboxylic acids and water.

### Claim 17 (depends on 16)

The process of claim 16 in which the protonic promoter is 1-butanol.

### Claim 18 (depends on 12)

The process of claim 12 in which less than 30 weight percent of an inert organic solvent is employed.

### Claim 19 (depends on 12)

The process of claim 12 in which the oligomerization reaction is conducted at a temperature in the range of about 25.degree. to 125.degree. C. and a pressure that is autogenous.

### Claim 20 (depends on 12)

The process of claim 12 in which the oligomerized olefins are subsequently hydrogenated.

### Claim 21

A process for oligomerizing mono olefins comprising contacting
a. A mixture of alpha olefins which consists essentially of
(1) at least one low molecular weight alpha olefin having 3 to 5 carbon atoms and
(2) at least one higher molecular weight alpha olefin having 8 to 18 carbon atoms, with
b. 0.2 to 3.0 weight percent of a catalyst comprising boron trifluoride in the presence of
c. 0.005 to 3.0 weight percent of an inorganic promoter which contains a transition metal cation selected from the group consisting of nickel, copper, cobalt and chromium, at a temperature in the range of about 25.degree. to 125.degree. C. and a pressure that is autogenous.

### Claim 22 (depends on 21)

The process of claim 21 in which the inorganic promoter is selected from the group consisting of elemental nickel, elemental copper, nickel oxide, copper oxide, chromium oxide, nickel fluoride, cobaltous carbonate, cobaltous fluoride and cobalt tetrafluoroborate, and mixtures thereof.

### Claim 23 (depends on 21)

The process of claim 21 in which a protonic promoter is employed in connection with the catalyst, the promoter being selected from the group consisting of alcohols, carboxylic acids and water.

### Claim 24 (depends on 23)

The process of claim 23 in which the protonic promoter is 1-butanol.

### Claim 25 (depends on 21)

The process of claim 21 in which less than 30 weight percent of an inert organic solvent is employed.

### Claim 26 (depends on 21)

The process of claim 21 in which the oligomerized olefins are subsequently hydrogenated.

### Claim 27

A process for the production of a synthetic lubricant component comprising
a. oligomerizing a mixture of alpha mono olefins having between 3 and 18 carbon atoms, inclusive, by contacting the mixture with boron trifluoride in the presence of an inorganic promoter containing a transition metal cation, at a temperature sufficient to produce a crude oligomer product,
b. neutralizing the crude oligomer product,
c. removing the organic layer from the neutralized crude oligomer product,
d. hydrogenating the oligomers in the removed organic layer, and
e. stripping off the molecules having less than 20 carbon atoms, the balance being the synthetic lubricant component.

### Claim 28 (depends on 27)

The process of claim 27 in which the mixture of alpha mono olefins consists essentially of
a. at least one low molecular weight alpha olefin having 3 to 5 carbon atoms, and
b. at least one higher molecular weight alpha olefin having 8 to 18 carbon atoms.

### Claim 29 (depends on 28)

The process of claim 28 in which the weight ratio of the low molecular weight alpha olefins to the higher molecular weight alpha olefins ranges from about 0.5:1 to 3:1.

### Claim 30 (depends on 27)

The process of claim 27 in which the catalyst is present in an amount of from 0.2 to 3.0 weight percent.

### Claim 31 (depends on 27)

The process of claim 27 in which the inorganic promoter contains a transition metal cation selected from the group consisting of nickel, copper, cobalt and chromium.

### Claim 32 (depends on 27)

The process of claim 27 in which the inorganic promoter is selected from the group consisting of elemental nickel, elemental copper, nickel oxide, copper oxide, chromium oxide, nickel fluoride, cobaltous carbonate, cobaltous fluoride and cobalt tetrafluoroborate, and mixtures thereof.

### Claim 33 (depends on 27)

The process of claim 27 in which the inorganic promoter is present in an amount of from 0.005 to 3.0 weight percent.

### Claim 34 (depends on 27)

The process of claim 27 in which a protonic promoter is employed in connection with the catalyst, the promoter being selected from the group consisting of alcohols, carboxylic acids and water.

### Claim 35 (depends on 34)

The process of claim 34 in which the protonic promoter is 1-butanol.

### Claim 36 (depends on 27)

The process of claim 27 in which less than 30 weight percent of an inert organic solvent is employed.

### Claim 37 (depends on 27)

The process of claim 27 in which the oligomerization reaction is conducted at a temperature in the range of about 25.degree. to 125.degree. C. and a pressure that is autogenous.

### Claim 38

A synthetic lubricant component having a viscosity at 210.degree. F. of between 3.5 and 5.0 centistokes being produced by oligomerizing a mixture of alpha mono olefins which consists essentially of low molecular weight alpha olefins having 3 to 5 carbon atoms and higher molecular weight alpha olefins having 8 to 18 carbon atoms, by means of contacting the alpha olefins with boron trifluoride in the presence of an inorganic promoter containing a transition metal cation, under oligomerization conditions, and subsequently hydrogenating the oligomerized olefins.

### Claim 39 (depends on 38)

The synthetic lubricant component of claim 38 in which the weight ratio of the low molecular weight alpha olefins to the higher molecular weight alpha olefins ranges from about 0.5:1 to 3:1.

### Claim 40 (depends on 38)

The synthetic lubricant component of claim 38 in which the catalyst is present in an amount of from 0.2 to 3.0 weight percent.

### Claim 41 (depends on 38)

The synthetic lubricant component of claim 38 in which the inorganic promoter contains a transition metal cation selected from the group consisting of nickel, copper, cobalt and chromium.

### Claim 42 (depends on 38)

The synthetic lubricant component of claim 38 in which the inorganic promoter is selected from the group consisting of elemental nickel, elemental copper, nickel oxide, copper oxide, chromium oxide, nickel fluoride, cobaltous carbonate, cobaltous fluoride and cobalt tetrafluoroborate, and mixtures thereof.

### Claim 43 (depends on 38)

The synthetic lubricant component of claim 38 in which the inorganic promoter is present in an amount of from 0.005 to 3.0 weight percent.

### Claim 44 (depends on 38)

The synthetic lubricant component of claim 38 in which a protonic promoter is present during the oligomerization, the promoter being selected from the group consisting of alcohols, carboxylic acids and water.

### Claim 45 (depends on 44)

The synthetic lubricant component of claim 44 in which the protonic promoter is 1-butanol.

### Claim 46 (depends on 38)

The synthetic lubricant component of claim 38 in which less than 30 weight percent of an inert organic solvent is present during oligomerization.

### Claim 47 (depends on 38)

The synthetic lubricant component of claim 38 in which the oligomerization reaction is conducted at a temperature in the range of about 25.degree. to 125.degree. C. and a pressure that is autogenous.