# US 9,752,167 B2 · Methods for production of L-methionine and related products

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- Number: US 9,752,167 B2
- Document ID: US9752167B2
- Status: Granted
- Kind: B2
- Application number: 14/982,108
- Filed: 2015-12-29
- Published: 2016-04-21
- Granted: 2017-09-05
- Earliest claimed: 2010-12-29
- Assignees: Cj Cheiljedang Corporation
- Applicants: Cj Cheiljedang Corporation
- Inventors: Soon Won Hong; In Seok Hwang; Sang Mok Lee; Youn Jae Lee; Jun Young Jung; Aharon Eyal
- Web page: https://patentgrep.com/patent/US9752167B2

## CPC

- C12P 13/12: Methionine; Cysteine; Cystine
- A23L 33/175: Amino acids
- C05C 3/00: Fertilisers containing other salts of ammonia or ammonia itself, e.g. gas liquor
- C07C 323/58: with amino groups bound to the carbon skeleton
- C12P 7/46: Dicarboxylic acids having four or less carbon atoms, e.g. fumaric acid, maleic acid
- C12P 7/54: Acetic acid (vinegar C12J)
- C12P 11/00: Preparation of sulfur-containing organic compounds
- C12P 13/06: Alanine; Leucine; Isoleucine; Serine; Homoserine
- A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs
- 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)}
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- C05C: NITROGENOUS FERTILISERS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION

## Abstract

A method comprising: (a) enzymatically processing an O-acetylhomoserine (OAHS) fermentation liquor to produce L-methionine and an acetate source; (b) separating at least a portion of said L-methionine from at least a fraction of said acetate source to form separated L-methionine and a residual liquor comprising an acetate-source; and (c) recovering at least a portion of said acetate source from said residual liquor as recovered acetate.

## Claims

### Claim 1

A method for producing an L-methionine product comprising;
(a) providing a fermentation liquor comprising an L-methionine precursor selected from the group consisting of O-acetylhomoserine (OAHS) and O-succinyl homoserine (OSHS), and at least one impurity;
(b) enzymatically processing said precursor to produce a reaction liquor comprising L-methionine, an organic acid selected from the group consisting of acetic acid and succinic acid and at least one impurity;
(c) modifying said reaction liquor to form a crystallizing feed;
(d) crystallizing L-methionine from said crystallizing feed to form crystalline L-methionine and an L-methionine-depleted mother liquor; and
(e) recovering at least a portion of said organic acid from said mother liquor as recovered organic acid; wherein said recovering comprises producing a residual liquor containing said free organic acid and separating said free organic acid,
and said crystalline L-methionine is characterized by at least one characteristic selected from the group consisting of:
(i) purity greater than 95%;
(ii) containing less than 1% organic acid;
(iii) L-methionine precursor content greater than 1 PPB;
(iv) content of at least one particular impurity is greater than 10 PPM;
(v) less than 2% of D-methionine; and
(vi) carbon-14 to carbon-12 ratio of at least 2.0×10−13.

### Claim 2 (depends on 1)

The method according to claim 1, wherein said modifying comprises combining said reaction liquor with an L-methionine-comprising recycle stream.

### Claim 3 (depends on 2)

The method according to claim 2, further comprising the step of separating L-methionine from said mother liquor to form said L-methionine-comprising recycle stream and a purged mother liquor stream.

### Claim 4 (depends on 3)

The method according to claim 3, wherein said separating L-methionine from said mother liquor comprises crystallizing to form second crystalline L-methionine and separating said second crystalline L-methionine from said purged mother liquor.

### Claim 5 (depends on 1)

The method according to claim 1, wherein one or more of said impurity is selected from the group consisting of amino acids, vitamins, minerals, ammonia, acetic acid, succinic acid, methyl mercaptan, enzymes, L-methionine precursor and a combination thereof.

### Claim 6 (depends on 1)

The method according to claim 1, wherein said L-methionine precursor is O-succinyl homoserine, wherein said organic acid is succinic acid and wherein said processing is conducted in the presence of calcium ions.

### Claim 7

A method for producing an L-methionine comprising;
(a) enzymatically processing a fermentation liquor comprising an L-methionine precursor selected from the group consisting of O-acetylhomoserine (OAHS) and O-succinylhomoserine (OSHS) to produce L-methionine and a source of an organic acid selected from acetic acid and succinic acid;
(b) separating at least a portion of said L-methionine from at least a fraction of said source of organic acid to form separated L-methionine and a residual liquor comprising the source of organic acid; and
(c) recovering at least a portion of said source of organic acid from said residual liquor as recovered organic acid, wherein said recovering comprises producing said residual liquor containing free organic acid and separating said free organic acid.

### Claim 8 (depends on 7)

The method according to claim 7, further comprising using said recovered organic acid as a reagent, wherein said using comprises applying to production of a fermentation product.

### Claim 9 (depends on 8)

The method according to claim 8, wherein said fermentation product is selected from the group consisting of carboxylic and amino acids.

### Claim 10 (depends on 7)

The method according to claim 7, further comprising using said recovered organic acid as a reagent, wherein said using comprises adding said reagent as an ingredient in a fermentation medium.

### Claim 11 (depends on 7)

The method according to claim 7, wherein said L-methionine precursor is O-succinyl homoserine, wherein said organic acid is succinic acid, and wherein recovering comprises forming residual liquor comprising free succinic acid and separating said free succinic acid.