WO2017155441A1 - Production equipment for production of caprolactone - Google Patents

Production equipment for production of caprolactone Download PDF

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Publication number
WO2017155441A1
WO2017155441A1 PCT/SE2017/000018 SE2017000018W WO2017155441A1 WO 2017155441 A1 WO2017155441 A1 WO 2017155441A1 SE 2017000018 W SE2017000018 W SE 2017000018W WO 2017155441 A1 WO2017155441 A1 WO 2017155441A1
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Prior art keywords
production equipment
equipment according
hydrogen peroxide
anyone
section
Prior art date
Application number
PCT/SE2017/000018
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French (fr)
Inventor
William John MAYO
Neil David EDWARDSON
Antony ORRELL
Jeremy Charles HAZLEHURST
Original Assignee
Perstorp Ab
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Priority to EP17763648.7A priority Critical patent/EP3426645A4/en
Publication of WO2017155441A1 publication Critical patent/WO2017155441A1/en

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24—Stationary reactors without moving elements inside
    • B01J19/2415—Tubular reactors
    • B01J19/242—Tubular reactors in series
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/18—Stationary reactors having moving elements inside
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24—Stationary reactors without moving elements inside
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • C07D313/02—Seven-membered rings
    • C07D313/04—Seven-membered rings not condensed with other rings
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24—Stationary reactors without moving elements inside
    • B01J19/2415—Tubular reactors
    • B01J19/243—Tubular reactors spirally, concentrically or zigzag wound
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00002—Chemical plants
    • B01J2219/00004—Scale aspects
    • B01J2219/00006—Large-scale industrial plants
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00002—Chemical plants
    • B01J2219/00027—Process aspects
    • B01J2219/0004—Processes in series
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
    • B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
    • B01J2219/00101—Reflux columns
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
    • B01J2219/00105—Controlling the temperature by indirect heating or cooling employing heat exchange fluids part or all of the reactants being heated or cooled outside the reactor while recycling
    • B01J2219/0011—Controlling the temperature by indirect heating or cooling employing heat exchange fluids part or all of the reactants being heated or cooled outside the reactor while recycling involving reactant liquids

Definitions

  • the present invention refers to a production equipment for production of a caprolactone, such as ⁇ -caprolactone, by reaction between peracetic acid and cyclohexanone in a so called Baeyer-Villiger reaction.
  • the first step in a caprolactone synthesis is typically the generation of peracetic acid, from acetic acid and hydrogen peroxide, used to oxidise cyclohexanone according to reaction scheme (I) below
  • the present invention is directed to a production equipment for production of a caprolactone by above disclosed reactions, said equipment is in embodiments split into a first section wherein peracetic acid is produced, a second section wherein caprolacton is produced, and a third section wherein yielded product is purified.
  • Said first section comprises, in embodiments of the present invention, a hydrogen peroxide inlet (1), a concentration unit (2) wherein hydrogen peroxide is concentrated into high strength hydrogen peroxide, a high strength hydrogen peroxide tank (3), a measure unit (4) wherein said high strength hydrogen peroxide and acetic acid are measured before being mixed and cooled in a premix unit (5), and peracetic acid stills (6) wherein said high strength hydrogen peroxide and said acetic acid is reacted in presence of a catalyst, such as sulphuric acid, and fractionated by distilling off yielded peracetic acid, unreacted acetic acid and water and holding back unreacted peroxide and catalyst.
  • a catalyst such as sulphuric acid
  • Said concentration unit (2) comprises, in especially preferred embodiments of said first section (Fig. 1), a serious of 3 peroxide concentrators (2a, 2b and 2c) being for instance film evaporators having large surface areas.
  • said premix unit (5) comprises a series of 3 agitated vessels (5a, 5b and 5c).
  • hydrogen peroxide is in said concentration unit (2), at a pressure of for instance 20-45 mBar and at a temperature of 50-60°C, such as 55 +/-2°C, concentrated into high strength peroxide comprising at least 80%, such as at least 85%, hydrogen peroxide.
  • the peracetic acid stills (6) are in said preferred embodiments suitably operated at 70-150, such as 1 10-130, mBar and yielded peracetic acid has typically a peracetic acid concentration of 30-55%.
  • Said second section (Fig. 2) comprises a peracetic inlet (7), a cyclohexanone inlet (8), at least two continuously stirred reactors (9 and 10) followed by a set of tubular reactors (11), in especially preferred embodiments at least 4, such as 6, tubular reactors (11a, l ib, 1 1c, l id, l ie and 11 f) in series wherein said peracetic acid and said cyclohexanone are reacted, a product cooler (12) wherein yielded reaction mixture is cooled, and an outlet (13) for further feeding of yielded reaction mixture to said third section.
  • tubular reactors 11a, l ib, 1 1c, l id, l ie and 11 f
  • Said third sector comprises, in preferred embodiments of the present invention, an inlet (14) for feeding of yielded reaction mixture, a pre-heater (15) heating the reaction mixture to a predetermined temperature, such as 50 +/- 5°C, a stripper (16) wherein water is removed, a fractionator (17) wherein light ends and unreacted raw materials are removed through an outlet (18).
  • the fractionated product is fed to a tank (19) and subsequently to a thin film evaporator (20) via a pre-heater (21) and finally to a distillation column (22), operating at for instance 0.5-20, such as 5-10, mbar, comprising separation steps yielding purified caprolactone.
  • the production equipment according to the present invention may optionally and additionally comprise a forth section (Fig. 4) comprising a tank (23) comprising unreacted raw materials and light ends which products are separated in at least a primary (24), a secondary (25) and a tertiary (26) distillation column, whereby cyclohexanone and acetic acid are recovered and optionally recycled.
  • Said primary distillation column (24) is, in preferred embodiments, operated at for instance atmospheric pressure, whereby an azeotrope of water and cyclohexanone is distilled off and separated in a decanter (27).
  • Acetic acid is, in said secondary distillation column (25), which suitably operates at for instance a temperature of 1 10-120°C, distilled off and sent to a storage tank.
  • Cyclohexanone is, under for instance vacuum condition, purified in said tertiary distillation column (26) and remains are sent for disposal. While particular embodiments of the invention have been shown, it will be understood, of course, that the invention is not limited thereto since many modifications may be made, and it is, therefore, contemplated to cover by the appended claims any such modifications as fall within the true spirit and scope of the invention.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Disclosed is a production equipment for production of a caprolactone by reaction between peracetic acid, produced from acetic acid and hydrogen peroxide, and cyclohexanone, said equipment being split into a first section (Fig. 1) wherein peracetic acid is produced, a second section (Fig. 2) wherein caprolacton is produced, and a third section (Fig. 3) wherein yielded product is purified.

Description

PRODUCTION EQUIPMENT FOR PRODUCTION OF CAPROLACTONE
The present invention refers to a production equipment for production of a caprolactone, such as ε-caprolactone, by reaction between peracetic acid and cyclohexanone in a so called Baeyer-Villiger reaction.
The first step in a caprolactone synthesis is typically the generation of peracetic acid, from acetic acid and hydrogen peroxide, used to oxidise cyclohexanone according to reaction scheme (I) below
Figure imgf000002_0001
Yielded peracetic acid reacts with cyclohexanone to yield caprolactone and acetic acid according to reaction scheme (II) below
Figure imgf000002_0002
The present invention is directed to a production equipment for production of a caprolactone by above disclosed reactions, said equipment is in embodiments split into a first section wherein peracetic acid is produced, a second section wherein caprolacton is produced, and a third section wherein yielded product is purified.
Said first section (Fig. 1) comprises, in embodiments of the present invention, a hydrogen peroxide inlet (1), a concentration unit (2) wherein hydrogen peroxide is concentrated into high strength hydrogen peroxide, a high strength hydrogen peroxide tank (3), a measure unit (4) wherein said high strength hydrogen peroxide and acetic acid are measured before being mixed and cooled in a premix unit (5), and peracetic acid stills (6) wherein said high strength hydrogen peroxide and said acetic acid is reacted in presence of a catalyst, such as sulphuric acid, and fractionated by distilling off yielded peracetic acid, unreacted acetic acid and water and holding back unreacted peroxide and catalyst. Yielded peracetic acid is subsequently and after addition of a stabiliser, such as dipicolinic acid, sent to a storage tank for further feeding to said second section (Fig.2). Said concentration unit (2) comprises, in especially preferred embodiments of said first section (Fig. 1), a serious of 3 peroxide concentrators (2a, 2b and 2c) being for instance film evaporators having large surface areas. In likewise preferred embodiments said premix unit (5) comprises a series of 3 agitated vessels (5a, 5b and 5c). 60-70%, such as 70%, hydrogen peroxide is in said concentration unit (2), at a pressure of for instance 20-45 mBar and at a temperature of 50-60°C, such as 55 +/-2°C, concentrated into high strength peroxide comprising at least 80%, such as at least 85%, hydrogen peroxide. The peracetic acid stills (6) are in said preferred embodiments suitably operated at 70-150, such as 1 10-130, mBar and yielded peracetic acid has typically a peracetic acid concentration of 30-55%.
Said second section (Fig. 2) comprises a peracetic inlet (7), a cyclohexanone inlet (8), at least two continuously stirred reactors (9 and 10) followed by a set of tubular reactors (11), in especially preferred embodiments at least 4, such as 6, tubular reactors (11a, l ib, 1 1c, l id, l ie and 11 f) in series wherein said peracetic acid and said cyclohexanone are reacted, a product cooler (12) wherein yielded reaction mixture is cooled, and an outlet (13) for further feeding of yielded reaction mixture to said third section.
Said third sector (Fig. 3) comprises, in preferred embodiments of the present invention, an inlet (14) for feeding of yielded reaction mixture, a pre-heater (15) heating the reaction mixture to a predetermined temperature, such as 50 +/- 5°C, a stripper (16) wherein water is removed, a fractionator (17) wherein light ends and unreacted raw materials are removed through an outlet (18). The fractionated product is fed to a tank (19) and subsequently to a thin film evaporator (20) via a pre-heater (21) and finally to a distillation column (22), operating at for instance 0.5-20, such as 5-10, mbar, comprising separation steps yielding purified caprolactone.
The production equipment according to the present invention may optionally and additionally comprise a forth section (Fig. 4) comprising a tank (23) comprising unreacted raw materials and light ends which products are separated in at least a primary (24), a secondary (25) and a tertiary (26) distillation column, whereby cyclohexanone and acetic acid are recovered and optionally recycled. Said primary distillation column (24) is, in preferred embodiments, operated at for instance atmospheric pressure, whereby an azeotrope of water and cyclohexanone is distilled off and separated in a decanter (27). Acetic acid is, in said secondary distillation column (25), which suitably operates at for instance a temperature of 1 10-120°C, distilled off and sent to a storage tank. Cyclohexanone is, under for instance vacuum condition, purified in said tertiary distillation column (26) and remains are sent for disposal. While particular embodiments of the invention have been shown, it will be understood, of course, that the invention is not limited thereto since many modifications may be made, and it is, therefore, contemplated to cover by the appended claims any such modifications as fall within the true spirit and scope of the invention. These and other objects will be more fully understood from appended drawings, wherein like reference numerals have been applied to like parts throughout the various figures and wherein:
Figur 1 : Schemes an embodiment of said first section of the claimed production equipment,
Figur 2: Schemes an embodiment of said second section of the claimed production equipment,
Figur 3: Schemes an embodiment of said third section of the claimed production equipment, and
Figur 4: Schemes an embodiment of said optional forth section of the claimed production equipment.

Claims

1. A production equipment for production of a caprolactone by reaction between peracetic acid, produced from acetic acid and hydrogen peroxide, and cyclohexanone, said equipment being split into a first section wherein peracetic acid is produced, a second section wherein caprolacton is produced, and a third section wherein yielded product is purified, whereby said first section (Fig. 1) comprises a hydrogen peroxide inlet (1), a concentration unit (2) wherein hydrogen peroxide is concentrated into high strength hydrogen peroxide, a high strength hydrogen peroxide tank (3), a measure unit (4) wherein said high strength hydrogen peroxide and acetic acid are measured before being mixed and cooled in a premix unit (5), and peracetic acid stills (6) wherein said high strength hydrogen peroxide and said acetic acid is reacted in presence of sulphuric acid as catalyst and fractionated by distilling off yielded peracetic acid, unreacted acetic acid and water and holding back unreacted peroxide and sulphuric acid, yielded peracetic acid is subsequently and after addition of dipicolinic acid, as stabiliser, sent to a storage tank for further feeding to said second section (Fig.2) comprising a peracetic inlet (7), a cyclohexanone inlet (8), at least two continuously stirred reactors (9, 10) followed by a set of tubular reactors (1 1) in series wherein said peracetic acid and said cyclohexanone are reacted, a product cooler (12) wherein yielded reaction mixture is cooled, and an outlet (13) for further feeding of yielded reaction mixture to said third section (Fig. 3) comprising an inlet (14) for feeding of yielded reaction mixture, a pre-heater (15), a stripper (16) wherein water is removed, a fractionator (17) wherein light ends and unreacted raw materials are removed through an outlet (18) and said fractionated product being fed to a tank (19), and subsequently to a thin film evaporator (20) via a pre-heater (21) and finally to a distillation column (22) with separation steps yielding purified caprolactone.
2. The production equipment according to Claim 1, wherein said concentration unit (2) comprises a serious of 3 peroxide concentrators (2a, 2b and 2c).
3. The production equipment according to Claim 2, wherein said peroxide concentrators (2a, 2b and 2c) are film evaporators having large surface areas.
4. The production equipment according to any of the Claims 1-3, wherein said premix unit (5) comprises a series of 3 agitated vessels (5a, 5b and 5c).
5. The production equipment according to anyone of the Claims 1-4, wherein 60-75% hydrogen peroxide is concentrated into high strength peroxide comprising at least 80% hydrogen peroxide.
6. The production equipment according to anyone of the Claims 1-5, wherein 60-75% hydrogen peroxide is concentrated at 20-45 mBar.
7. The production equipment according to anyone of the Claims 1-6, wherein 60-75%) hydrogen peroxide is concentrated at 50-60°C.
8. The production equipment according to anyone of the Claims 1-7, wherein 70% hydrogen peroxide is concentrated at a temperature of 55 +/-2C into high strength peroxide comprising at least 85% hydrogen peroxide.
9. The production equipment according to anyone of the Claims 1-8, wherein yielded peracetic acid has a peracetic acid concentration of 30-55%.
10. The production equipment according to anyone of the Claims 1-9, wherein said peracetic acid stills (6) are operated at 70-150 mBar.
1 1. A production equipment according to anyone of the Claims 1-11 characterised in that said set of tubular reactors (11) comprises 6 tubular reactors (11a, l ib, 1 1 c, l id, l ie and 1 If) in series.
12. The production equipment according to anyone of the Claims 1-11, wherein said pre- heater (15) heats said reaction mixture to 50 +/- 5°C.
13. The production equipment according to anyone of the Claims 1-12, wherein said distillation column (22) operates at a pressure of 0.5-20 mbar.
14. The production equipment according to anyone of the Claims 1-13, wherein said distillation column (22) operates at a pressure of 5-10 mBar.
15. The production equipment according to anyone of the Claims 1-14, wherein it optionally and additionally comprises a forth section (Fig. 4) comprising a tank (23) comprising unreacted raw materials and light ends which products are separated in at least a primary (24), a secondary (25) and a tertiary (26) distillation column, whereby cyclohexanone and acetic acid are recovered and optionally recycled.
16. The production equipment according to Claim 15, wherein said primary distillation column (24) operates at atmospheric pressure and wherein an azeotrope of water and cyclohexanone is distilled off and separated in a decanter (27).
17. The production equipment according to Claim 15 or 16, wherein said secondary distillation column (25) operates at a temperature of 110-120°C and wherein acetic acid is distilled off and sent to a storage tank.
18. The production equipment according to anyone of the Claims 15-17, wherein said tertiary distillation column (26) purifies cyclohexanone under vacuum condition and wherein remains are sent for disposal.
PCT/SE2017/000018 2016-03-09 2017-03-03 Production equipment for production of caprolactone WO2017155441A1 (en)

Priority Applications (1)

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EP17763648.7A EP3426645A4 (en) 2016-03-09 2017-03-03 Production equipment for production of caprolactone

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1604114.7A GB2548138A (en) 2016-03-09 2016-03-09 Production equipment (II) for production of a caprolactone
GBGB1604114.7 2016-03-09

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Cited By (6)

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Publication number Priority date Publication date Assignee Title
CN109705083A (en) * 2019-01-29 2019-05-03 安徽华业香料合肥有限公司 A kind of synthetic method of ε-decalactone fragrance
CN109748900A (en) * 2019-01-29 2019-05-14 安徽华业香料合肥有限公司 A kind of production method of ε-decalactone synthetic perfume
EP3693430A1 (en) 2019-02-08 2020-08-12 tesa SE Thermally softenable adhesive tape and method for covering elongated products, in particular cables
US11208394B2 (en) 2018-09-17 2021-12-28 Regents Of The University Of Minnesota Chemical process to manufacture branched-caprolactone
US11466177B2 (en) 2019-02-08 2022-10-11 Tesa Se Moisture-curable adhesive tape and method for jacketing elongated items, especially leads
US11965121B2 (en) 2019-02-08 2024-04-23 Tesa Se UV-curable adhesive tape and method for jacketing elongated items, especially leads

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11208394B2 (en) 2018-09-17 2021-12-28 Regents Of The University Of Minnesota Chemical process to manufacture branched-caprolactone
CN109705083A (en) * 2019-01-29 2019-05-03 安徽华业香料合肥有限公司 A kind of synthetic method of ε-decalactone fragrance
CN109748900A (en) * 2019-01-29 2019-05-14 安徽华业香料合肥有限公司 A kind of production method of ε-decalactone synthetic perfume
EP3693430A1 (en) 2019-02-08 2020-08-12 tesa SE Thermally softenable adhesive tape and method for covering elongated products, in particular cables
US11466177B2 (en) 2019-02-08 2022-10-11 Tesa Se Moisture-curable adhesive tape and method for jacketing elongated items, especially leads
US11680189B2 (en) 2019-02-08 2023-06-20 Tesa Se Thermally softenable adhesive tape and method for jacketing elongated items, especially leads
US11965121B2 (en) 2019-02-08 2024-04-23 Tesa Se UV-curable adhesive tape and method for jacketing elongated items, especially leads

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GB2548138A (en) 2017-09-13
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GB201604114D0 (en) 2016-04-20

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