# US 2019/0169153 A1 · Processes for conversion of biologically derived mevalonic acid

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- Number: US 2019/0169153 A1
- Document ID: US20190169153A1
- Status: Published application
- Kind: A1
- Application number: 16/278,570
- Filed: 2019-02-18
- Published: 2019-06-06
- Earliest claimed: 2014-11-26
- Assignees: Visolis, Inc.
- Applicants: Visolis, Inc.
- Inventors: Deepak Dugar; Brian Neltner
- Web page: https://patentgrep.com/patent/US20190169153A1

## CPC

- C07D 309/30: Oxygen atoms, e.g. delta-lactones
- C07C 1/207: from carbonyl compounds
- C07C 45/66: by dehydration
- C12P 7/42: Hydroxy-carboxylic acids
- C07C 2521/04: Alumina
- C07C 2521/06: Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- C07C 2521/08: Silica
- C07C 2521/10: Magnesium; Oxides or hydroxides thereof
- C07C 2521/12: Silica and alumina
- C07C 2523/44: Palladium
- C07C 2529/40: of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}

## Abstract

The invention relates to a process comprising reacting mevalonic acid, or a solution comprising mevalonic acid, to yield a first product or first product mixture, optionally in the presence of a solid catalyst and/or at elevated temperature and/or pressure. The invention further relates to a process comprising: (a) providing a microbial organism that expresses a biosynthetic mevalonic acid pathway; (b) growing the microbial organism in fermentation medium comprising suitable carbon substrates, whereby biobased mevalonic acid is produced; and (c) reacting said biobased mevalonic acid to yield a first product or first product mixture.

## Claims

### Claim 1

A process comprising reacting MVL, or a solution comprising MVL, in the presence of an acid catalyst at a temperature greater than or equal to 100° C. and less than or equal to 300° C. and a pressure in the range of atmospheric pressure to less than 50 bar to yield a first product or first product mixture comprising anhydro-mevalonolactone, isoprene, 1,3-Cyclohexadiene,1-methyl-4-(1-methylethyl), methyl vinyl ketone, 3-methyl-2-butanone, 2-pentene, 2-methyl-1-butene, 2-methyl-1-pentene, methane, hydrogen, an alcohol, and/or a carboxylic acid.

### Claim 2 (depends on 1)

The process of claim 1, wherein said temperature is greater than or equal to 150° C. and less than or equal to 200° C. and said pressure is less than or equal to 5 bar.

### Claim 3 (depends on 1)

The process of claim 1, wherein said first product comprises anhydro-mevalonolactone, isoprene, and/or 1,3-Cyclohexadiene,1-methyl-4-(1-methylethyl).

### Claim 4 (depends on 1)

The process of claim 1, wherein said first product comprises at least one C10H16 compound.

### Claim 5 (depends on 4)

The process of claim 4, wherein said at least one C10H16 compound comprises 1,3-Cyclohexadiene,1-methyl-4-(1-methylethyl).

### Claim 6 (depends on 1)

The process of claim 1, wherein said solution comprises a co-reactant.

### Claim 7 (depends on 6)

The process of claim 6, wherein said co-reactant comprises water, alkyl alcohol, ethers, aromatic compounds, acids, aldehydes and/or esters.

### Claim 8 (depends on 1)

The process of claim 1, wherein said acid catalyst comprises a solid acid catalyst having a surface area greater than or equal to 50 m2/g.

### Claim 9 (depends on 1)

The process of claim 1, wherein said acid catalyst comprises a sulfonated resin, a metal oxide, a zeolite, a supported transition metal, and/or a supported noble metal.

### Claim 10

A process comprising: (a) reacting MVL, or a solution comprising MVL, at a first temperature in the range of 150° C. to 400° C. and at a first pressure in the range of from atmospheric pressure to less than 100 bar to yield a first product or first product mixture; and (b) reacting said first product or first product mixture in the presence of an acid catalyst at a second temperature greater than or equal to 50° C. and less than or equal to 200° C. to yield a second product or second product mixture.

### Claim 11 (depends on 10)

The process of claim 10, wherein said reacting of step (a) is performed in the absence of a catalyst.

### Claim 12 (depends on 10)

The process of claim 10, wherein said MVL comprises ring-opened MVL.

### Claim 13 (depends on 10)

The process of claim 10, wherein said solution comprise a co-reactant.

### Claim 14 (depends on 13)

The process of claim 13, wherein said co-reactant comprises water, alkyl alcohol, ethers, aromatic compounds, acids, aldehydes and/or esters.

### Claim 15 (depends on 10)

The process of claim 10, wherein said reacting of step (a) is performed in the absence of a catalyst, said MVL comprises ring-opened MVL, said solution comprises water, and said first temperature is less than or equal to 200° C.

### Claim 16 (depends on 10)

The process of claim 10, wherein said first product or first product mixture comprises anhydro-mevalonolactone, isoprene, 1,3-Cyclohexadiene,1-methyl-4-(1-methylethyl), methyl vinyl ketone, 3-methyl-2-butanone, 2-pentene, 2-methyl-1-butene, 2-methyl-1-pentene, methane, hydrogen, an alcohol, and/or a carboxylic acid.

### Claim 17 (depends on 10)

The process of claim 10, wherein said first product comprises anhydro-mevalonolactone, isoprene, and/or 1,3-Cyclohexadiene,1-methyl-4-(1-methylethyl).

### Claim 18 (depends on 10)

The process of claim 10, wherein said reacting of step (a) is performed in the presence of a first catalyst.

### Claim 19 (depends on 18)

The process of claim 18, wherein said first catalyst and said acid catalyst are each solid acid catalysts.

### Claim 20

A process comprising reacting MVL, or a solution comprising MVL, at a temperature greater than or equal to 150° C. and less than or equal to 200° C. and a pressure in the range of atmospheric pressure to less than 50 bar to yield a first product or first product mixture comprising at least one C5H8 compound and/or at least one C10H16 compound.

### Claim 21 (depends on 20)

The process of claim 20, wherein said at least one C5H8 compound comprises isoprene and said at least one C10H16 compound comprises 1,3-Cyclohexadiene,1-methyl-4-(1-methylethyl).

### Claim 22 (depends on 20)

The process of claim 20, wherein said first product or first product mixture comprises at least one C10H16.

### Claim 23 (depends on 22)

The process of claim 22, wherein said first product or first product mixture comprises said at least one C5H8 compound.

### Claim 24 (depends on 20)

The process of claim 20, wherein said reacting is performed in the absence of a catalyst, said MVL comprises ring-opened MVL, and said solution comprises water.

### Claim 25 (depends on 20)

The process of claim 20, further comprising reacting at least a portion of said first product or first product mixture in the presence of an acid catalyst to yield a second product or second product mixture.

### Claim 26 (depends on 25)

The process of claim 25, wherein said second product or second product mixture comprises at least one C10H16 compound.

### Claim 27 (depends on 20)

The process of claim 20, wherein said solution comprises a co-reactant.

### Claim 28 (depends on 20)

The process of claim 20, wherein said reacting is carried out in the presence of an acid catalyst.

### Claim 29 (depends on 28)

The process of claim 28, wherein said acid catalyst comprises a sulfonated resin, a metal oxide, a zeolite, a supported transition metal, and/or a supported noble metal.