# US 10,501,399 B2 · Lactic acid manufacturing method

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- Number: US 10,501,399 B2
- Document ID: US10501399B2
- Status: Granted
- Kind: B2
- Application number: 15/129,870
- Filed: 2015-03-30
- Published: 2017-06-01
- Granted: 2019-12-10
- Earliest claimed: 2014-03-31
- Assignees: Toray Industries, Inc.
- Applicants: Toray Industries, Inc.
- Inventors: Kenji Kawamura; Miyuki Horiguchi; Satoshi Sakami; Katsushige Yamada
- Web page: https://patentgrep.com/patent/US10501399B2

## CPC

- C07C 51/43: by change of the physical state, e.g. crystallisation
- C07C 51/44: by distillation
- C08G 63/06: derived from hydroxycarboxylic acids
- C08G 63/08: Lactones or lactides
- C08G 63/80: Solid-state polycondensation
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

A method of producing lactic acid includes subjecting a lactic acid-containing solution to distillation to collect lactic acid from the vapor side (Step A); subjecting the lactic acid obtained in Step A to crystallization (Step B); subjecting the lactic acid slurry obtained in Step B to solid-liquid separation into lactic acid crystals and a mother liquor (Step C); and circulating the mother liquor obtained in Step C to Step B (Step D).

## Claims

### Claim 1

A method of producing lactic acid comprising:
subjecting a lactic-acid containing solution to distillation to collect lactic acid from the vapor side (Step A);
subjecting the lactic acid obtained in Step A to crystallization (Step B);
subjecting a lactic acid slurry obtained in (Step B) to solid-liquid separation into lactic acid crystals and a mother liquor containing a lactic acid oligomer (Step C); and
circulating the mother liquor obtained in Step C to Step B (Step D),
wherein a mixture of the mother liquor circulated in Step D and the lactic acid obtained in Step A is subjected to crystallization to obtain lactic acid crystals.

### Claim 2 (depends on 1)

The method according to claim 1, wherein said lactic acid-containing solution is derived by microbial fermentation.

### Claim 3 (depends on 1)

The method according to claim 1, wherein said crystallization in Step B is cooling crystallization, evaporative crystallization, or insulated crystallization.

### Claim 4 (depends on 1)

A method of producing polylactic acid comprising:
producing lactic acid by the method according to claim 1; and
producing polylactic acid using said lactic acid obtained in said step as a material (Step E).

### Claim 5 (depends on 4)

The method according to claim 4, wherein said Step (E) is a step of direct dehydration condensation of said lactic acid.

### Claim 6 (depends on 2)

The method according to claim 2, wherein said crystallization in Step B is cooling crystallization, evaporative crystallization, or insulated crystallization.

### Claim 7 (depends on 2)

A method of producing polylactic acid comprising:
producing lactic acid by the method according to claim 2; and
producing polylactic acid using said lactic acid obtained in said step as a material (Step E).

### Claim 8 (depends on 3)

A method of producing polylactic acid comprising:
producing lactic acid by the method according to claim 3; and
producing polylactic acid using said lactic acid obtained in said step as a material (Step E).

### Claim 9 (depends on 7)

The method according to claim 7, wherein said Step (E) is a step of direct dehydration condensation of said lactic acid.

### Claim 10 (depends on 8)

The method according to claim 8, wherein said Step (E) is a step of direct dehydration condensation of said lactic acid.

### Claim 11

A method of producing lactic acid comprising:
subjecting a lactic acid-containing solution to distillation to collect lactic acid from the vapor side (Step A);
partially condensing vapor from the vapor side to produce liquid lactic acid and water, and condensing a remaining portion of the vapor to produce water and low boiling point components (Step A1);
subjecting the lactic acid obtained in (Step A1) to crystallization (Step B);
subjecting lactic acid slurry obtained in (Step B) to solid-liquid separation into lactic acid crystals and a mother liquor containing a lactic acid oligomer (Step C); and
circulating the mother liquor obtained in (Step C) to (Step B) (Step D),
wherein a mixture of the mother liquor circulated in Step D and the lactic acid obtained in Step A is subjected to crystallization to obtain lactic acid crystals.

### Claim 12 (depends on 11)

The method according to claim 11, wherein said lactic acid-containing solution is derived by microbial fermentation.

### Claim 13 (depends on 11)

The method according to claim 11, wherein said crystallization in Step B is cooling crystallization, evaporative crystallization, or insulated crystallization.

### Claim 14 (depends on 11)

A method of producing polylactic acid comprising:
producing lactic acid by the method according to claim 11; and
producing polylactic acid using said lactic acid obtained in said step as a material (Step E).

### Claim 15 (depends on 14)

The method according to claim 14, wherein said Step (E) is a step of direct dehydration condensation of said lactic acid.

### Claim 16 (depends on 12)

The method according to claim 12, wherein said crystallization in Step B is cooling crystallization, evaporative crystallization, or insulated crystallization.

### Claim 17 (depends on 12)

A method of producing polylactic acid comprising:
producing lactic acid by the method according to claim 12; and
producing polylactic acid using said lactic acid obtained in said step as a material (Step E).

### Claim 18 (depends on 13)

A method of producing polylactic acid comprising:
producing lactic acid by the method according to claim 13; and
producing polylactic acid using said lactic acid obtained in said step as a material (Step E).

### Claim 19 (depends on 17)

The method according to claim 17, wherein said Step (E) is a step of direct dehydration condensation of said lactic acid.

### Claim 20 (depends on 18)

The method according to claim 18, wherein said Step (E) is a step of direct dehydration condensation of said lactic acid.

### Claim 21

A method of producing lactic acid comprising:
subjecting a solution containing water and lactic acid to distillation to collect lactic acid from the vapor side (Step A), wherein the distillation comprises recovering vaporized lactic acid and a portion of the water in a first-stage condenser and recovering remaining water and low boiling components in a second-stage condenser;
subjecting the lactic acid obtained in Step A to crystallization (Step B);
subjecting the lactic acid slurry obtained in Step B to solid-liquid separation into lactic acid crystals and a mother liquor (Step C); and
circulating the mother liquor obtained in Step C to Step B (Step D),
wherein a mixture of the mother liquor circulated in Step D and the lactic acid obtained in Step A is subjected to crystallization to obtain lactic acid crystals.
