# US 2013/0253239 A1 · Heavy Alkylbenzene Production Through Oligomerization

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- Number: US 2013/0253239 A1
- Document ID: US20130253239A1
- Status: Published application
- Kind: A1
- Application number: 13/428,559
- Filed: 2012-03-23
- Published: 2013-09-26
- Earliest claimed: 2012-03-23
- Assignees: Uop LLC
- Inventors: Andrea G. Bozzano; Jeffery C. Bricker; Bryan K. Glover
- Web page: https://patentgrep.com/patent/US20130253239A1

## CPC

- C07C 7/167: for removal of compounds containing a triple carbon-to-carbon bond
- C07C 2/06: of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C 2/64: Addition to a carbon atom of a six-membered aromatic ring
- C07C 5/327: Formation of non-aromatic carbon-to-carbon double bonds only
- C07C 7/163: by hydrogenation
- C10G 9/00: Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
- C10G 29/205: {by reaction with hydrocarbons added to the hydrocarbon oil}
- C10G 45/32: Selective hydrogenation of the diolefin or acetylene compounds
- C10G 50/00: Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
- C10G 57/005: {with alkylation}
- C10G 57/02: with polymerisation
- C10G 69/00: Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process (C10G67/00 takes precedence)
- C10G 2300/1011: Biomass
- C10G 2300/1022: Fischer-Tropsch products
- C10G 2300/4081: Recycling aspects
- C10G 2400/22: Higher olefins
- C10G 2400/30: Aromatics
- Y02P 30/20: using bio-feedstock
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C10G: CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION (cracking to hydrogen or synthesis gas C01B; cracking or pyrolysis of hydrocarbon gases to individual hydrocarbons or mixtures thereof of definite or specified constitution C07C; cracking to cokes C10B); RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A process for producing heavy alkyl aromatics is presented. The process utilizes low molecular weight hydrocarbons for generating larger alkyl groups. The hydrocarbons can be generated from a variety of sources including Fischer-Tropsch liquids. The process includes oligomerization of low molecular weight olefins to larger olefins. The larger olefins are passed to an alkylation reactor to alkylate aromatic compounds.

## Claims

### Claim 1

A process for producing heavy olefins, comprising:
passing a hydrocarbon feedstock, comprising C4 to C6 olefins to an oligomerization reactor to generate a first stream comprising heavy olefins in the C15 to C36 range; and
passing the first stream to a first separation unit to generate a product stream comprising C15 to C36 olefins, and a recycle stream having a reduced heavy olefin content.

### Claim 2 (depends on 1)

The process of claim 1 wherein the hydrocarbon feedstock is a light cracked naphtha.

### Claim 3 (depends on 1)

The process of claim 1 wherein the product stream comprises C18 to C28 olefins.

### Claim 4 (depends on 1)

The process of claim 1 further comprising:
passing the recycle stream to a second separation unit to generate a first recycle stream comprising olefins in the C4 to C14 range and a second recycle stream having reduced olefin content; and
passing the first recycle stream to the oligomerization reactor.

### Claim 5 (depends on 4)

The process of claim 4 further comprising:
passing the second recycle stream to a dehydrogenation unit to generate a dehydrogenation stream comprising C4 to C6 olefins; and
passing the dehydrogenation stream to the oligomerization reactor.

### Claim 6 (depends on 4)

The process of claim 4 further comprising:
passing the dehydrogenation stream to a selective hydrogenation reactor to generate a dehydrogenation stream with reduced alkyne and diolefin content; and
passing the dehydrogenation stream with reduced alkyne and diolefin content to the oligomerization reactor.

### Claim 7 (depends on 5)

The process of claim 5 further comprising:
passing the dehydrogenation stream to a third separation unit to generate a light stream comprising C4 to C8 olefins and a heavy stream comprising C9 to C14 olefins;
passing the heavy stream to a dimerization reactor to generate a dimerization reactor product stream comprising C18 to C28 olefins; and
passing the light stream to the oligomerization reactor.

### Claim 8 (depends on 1)

The process of claim 1 further comprising:
passing a portion of the product stream to an alklation reactor; and
passing an aromatic stream, comprising aromatic compounds, to the alkylation reactor to alkylate the aromatic compounds with the olefins under alkylation conditions to generate an alkylaromatic stream comprising alkylaromatic compounds having carbon chains in the C15 to C36 range on the aromatic groups.

### Claim 9 (depends on 8)

The process of claim 8 further comprising separating the aromatic compounds from at least a portion of the alkylaromatic stream to generate an alkylaromatic product stream, and aromatics stream.

### Claim 10 (depends on 9)

The process of claim 9 further comprising passing the aromatics stream to the alkylation reactor.

### Claim 11 (depends on 8)

The process of claim 8 wherein the aromatic compounds comprise benzene and toluene.

### Claim 12

An integrated process for producing detergent range alkylbenzenes from a hydrocarbon feedstock comprising C4 and C6 olefins and oxygenated compounds, the process comprising:
contacting the feedstock with a liquid extractant comprising at least one of alcohol and diol having 1 to 3 carbon atoms per molecule and a minor amount of water under extraction conditions to provide a deoxygenated feedstock having a reduced concentration of oxygenated compounds and a spent extractant;
regenerating at least a portion of the spent extractant to provide at least a portion of the liquid extractant;
reacting at least a portion of the C4 and C6 olefins in an oligomerization reactor under chain growth conditions to provide a heavy olefin stream comprising C15 to C36 mono-olefins;
passing the heavy olefin stream to a separation unit to generate a heavy olefin product stream comprising C15 to C36 mono-olefins, and a second stream having reduced heavy olefin content;
alkylating benzene with at least a portion of the heavy olefin product stream under alkylation conditions including a stoichiometric excess of benzene to olefin to provide an alkylation effluent comprising alkylbenzenes and benzene; and
separating benzene from at least a portion of the alkylation effluent and recycling at least a portion of the separated benzene to alkylation step.

### Claim 13 (depends on 12)

The process of claim 12 further comprising:
passing the second stream to a dehydrogenation unit to generate a third stream comprising olefins; and
passing the third stream to the oligomerization reactor.

### Claim 14 (depends on 13)

The process of claim 13 wherein the third stream contains about 1 to 50 mass-percent C5 and C6 mono-olefins.

### Claim 15 (depends on 14)

The process of claim 14 wherein the third feedstock is subjected to selective hydrogenation.

### Claim 16 (depends on 12)

The process of claim 12 wherein the hydrocarbon feedstock is derived from Fischer-Tropsch synthesis.

### Claim 17 (depends on 12)

The process of claim 12 wherein the liquid extractant comprises methanol and contains less than about 25 mass-percent water.

### Claim 18 (depends on 12)

The process of claim 12 wherein the hydrocarbon feedstock is derived from renewable sources.