Systems and processes for polyacrylic acid production

• US 10,428,165 B2
• Filed: 02/12/2016
• Issued: 10/01/2019
• Est. Priority Date: 02/13/2015
• Status: Active Grant

• Current Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Original Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Inventors: Sookraj, Sadesh H.
• Primary Examiner(s): Bernshteyn, Michael
• Application Number:
  US15/550,111
• Publication Number:
  US 20180057619A1
• Time in Patent Office: 1,327 Days
• Field of Search: 526317
• CPC Class Codes: C07C 51/12 on an oxygen-containing group in organic compounds, e.g. alcohols
• CPC Class Codes: C07C 51/14 on a carbon-to-carbon unsaturated bond in organic compounds
• CPC Class Codes: C07C 51/145 with simultaneous oxidation
• CPC Class Codes: C07C 51/377 by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups C07C51/36 - C07C51/373 take precedence
• CPC Class Codes: C07C 57/04 Acrylic acid; Methacrylic acid
• CPC Class Codes: C07C 59/01 Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
• CPC Class Codes: C08F 2/01 characterised by special features of the polymerisation apparatus used
• CPC Class Codes: C08F 2/18 Suspension polymerisation
• CPC Class Codes: C08F 20/06 Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof

Abstract

Disclosed are systems and methods for the production of polyacrylic acid and superabsorbent polymers from ethylene oxidation to form ethylene oxide. Reacting the ethylene oxide with carbon monoxide to form to beta propiolactone (BPL) or polypropiolactone (PPL), or a combination thereof. An outlet configured to provide a carbonylation stream comprising the BPL or PPL, or a combination thereof and using one or more reactors to convert BPL to acrylic acid or to convert at least some of the BPL to PPL, and then to convert PPL to acrylic acid. An outlet configured to provide a PPL stream to a second reactor tm to convert at least some of the PPL to AA or a third reactor to convert at least some of the PPL to AA. The outlet configured to provide an AA stream to a fourth reactor to convert the AA to polyacrylic acid.

Claims

1. An integrated system for producing polyacrylic acid (PAA) and superabsorbent polymer (SAP) from ethylene, comprising:

an oxidative reactor, comprising;

an inlet configured to receive ethylene,

an oxidative reaction zone configured to convert ethylene to ethylene oxide (EO), and

an outlet configured to provide an EO stream comprising the EO;

a central reactor, comprising;

an inlet configured to receive EO from the EO stream of the oxidative reactor, and carbon monoxide (CO) from a CO source,

a central reaction zone configured to convert EO to beta propiolactone (BPL) or polypropiolactone (PPL), or a combination thereof, and

an outlet configured to provide a carbonylation stream comprising the BPL, or a carbonylation stream comprising the PPL, or a combination thereof;

one or more of (i), (ii) and (iii);

(i) a first reactor, comprising;

an inlet configured to receive BPL from the carbonylation stream of the central reactor,

a first reaction zone configured to convert BPL to acrylic acid (AA), and

an outlet configured to provide an AA stream comprising the AA,

(ii) a second (a) reactor, comprising;

an inlet configured to receive BPL from the carbonylation stream of the central reactor,

a second (a) reaction zone configured to convert BPL to PPL, and

an outlet configured to provide a PPL stream comprising the PPL, and

a second (b) reactor, comprising;

an inlet configured to receive the PPL stream of the second (a) reactor,

a second (b) reaction zone configured to convert at least some of the PPL to AA, and

an outlet configured to provide an AA stream comprising the AA, and

(iii) a third reactor, comprising;

an inlet configured to receive PPL from the carbonylation stream of the central reactor,

a third reaction zone configured to convert PPL to AA, and

an outlet configured to provide an AA stream comprising the AA;

a fourth reactor, comprising;

an inlet configured to receive the AA stream of one or more of the first, second (b) and third reactor,

a fourth reaction zone configured to convert AA to polyacrylic acid (PAA), or a salt thereof, and

an outlet configured to provide a PAA stream comprising the PAA, or a salt thereof;

a fifth reactor, comprising;

an inlet configured to receive PAA, or a salt thereof, from the PAA stream of the fourth reactor,

a fifth reaction zone configured to directly convert the PAA, or a salt thereof, to superabsorbent polymer (SAP), and

an outlet configured to provide a SAP stream comprising the SAP; and

a controller to independently modulate production of the EO, BPL, PPL, AA, PAA and SAP.

2. The system of claim 1, comprising two of (i), (ii) and (iii).

3. The system of claim 1, comprising (i), (ii) and (iii).

4. The system of claim 1, wherein the system produces AA at 200 kilotons to 800 kilotons per annum (kta).

5. The system of claim 1, wherein the AA has less than 5% by weight of an aldehyde impurity or a compound that derives from the oxidation of propylene.

6. The system of claim 1, wherein the inlet to the fourth reactor is configured to receive one or more reactant streams comprising sodium hydroxide, and the fourth reaction zone is configured to form a PAA sodium salt from the one or more reactant streams in the presence of a radical initiator.

7. The system of claim 1, wherein the fourth reaction zone is configured to convert AA to polyacrylic acid (PAA), or a salt thereof, by gel polymerization, suspension polymerization, or solution polymerization.

8. The system of claim 1, wherein the PAA, or a salt thereof, has less than 5% by weight of an aldehyde impurity or a compound that derives from the oxidation of propylene.

9. The system of claim 1, wherein the inlet to the fourth reactor is configured to further receive one or more reactant streams each comprising a co-reactant to co-polymerize with AA, and the fourth reaction zone is configured to form one or more co-polymers of PAA selected from the group consisting of a polyacrylamide co-polymer, ethylene maleic anhydride co-polymer, cross-linked carboxymethylcellulose co-polymer, polyvinyl alcohol co-polymer, cross-linked polyethylene oxide co-polymer, and starch grafted polyacrylonitrile co-polymer of PAA.

10. The system of claim 1, wherein the inlet to the fifth reactor is configured to further receive one or more reactant streams each comprising a cross-linking agent.

11. The system of claim 1, wherein the SAP has less than 1000 parts per million residual monoethylenically unsaturated monomer, and has less than 5% by weight of an aldehyde impurity or a compound that derives from the oxidation of propylene.

12. The system of claim 1, wherein the controller independently modulates production of the BPL by the central reactor.

13. The system of claim 1, wherein the AA stream has:

less than 1000 parts per million residual monoethylenically unsaturated monomer,

(ii) less than 5% by weight or less than 10,000 ppm of an aldehyde impurity,

(iii) less than 5% by weight or less than 10,000 ppm of a compound that derives from the oxidation of propylene,

(iv) less than 5% by weight or less than 10,000 ppm of furfural,

(v) less than 5% by weight or less than 10,000 ppm of acetic acid,

(vi) less than 5% by weight or less than 10,000 ppm of stabilizers,

(vii) less than 5% by weight or less than 10,000 ppm of radical polymerization inhibitors,

(viii) less than 5% by weight or less than 10,000 ppm of anti-foam agents,

or any combination of (i)-(viii).