ZA200201553B - Process for the production and purification of n-butyl acrylate. - Google Patents
Process for the production and purification of n-butyl acrylate. Download PDFInfo
- Publication number
- ZA200201553B ZA200201553B ZA200201553A ZA200201553A ZA200201553B ZA 200201553 B ZA200201553 B ZA 200201553B ZA 200201553 A ZA200201553 A ZA 200201553A ZA 200201553 A ZA200201553 A ZA 200201553A ZA 200201553 B ZA200201553 B ZA 200201553B
- Authority
- ZA
- South Africa
- Prior art keywords
- buaca
- buoh
- zone
- light ends
- purge recovery
- Prior art date
Links
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 title claims description 81
- 238000000034 method Methods 0.000 title claims description 32
- 238000004519 manufacturing process Methods 0.000 title description 5
- 238000000746 purification Methods 0.000 title description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 99
- 238000011084 recovery Methods 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 45
- 238000010926 purge Methods 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 239000012074 organic phase Substances 0.000 claims description 24
- 239000008346 aqueous phase Substances 0.000 claims description 20
- 238000010992 reflux Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- 238000005194 fractionation Methods 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 5
- 238000004064 recycling Methods 0.000 claims 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 14
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 8
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- BQIMPGFMMOZASS-CLZZGJSISA-N (6r,7r)-7-amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(CO)=C(C(O)=O)N2C(=O)[C@@H](N)[C@H]21 BQIMPGFMMOZASS-CLZZGJSISA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
- -1 alkyl dihydroxybenzene Chemical compound 0.000 description 3
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 2
- 238000006845 Michael addition reaction Methods 0.000 description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/395,410 US6172258B1 (en) | 1999-09-14 | 1999-09-14 | Process for the production and purification of n-butyl acrylate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200201553B true ZA200201553B (en) | 2003-04-30 |
Family
ID=23562912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200201553A ZA200201553B (en) | 1999-09-14 | 2002-02-25 | Process for the production and purification of n-butyl acrylate. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6172258B1 (cs) |
| EP (1) | EP1212284A1 (cs) |
| JP (1) | JP2003509396A (cs) |
| KR (1) | KR20020026273A (cs) |
| CN (1) | CN1374939A (cs) |
| AU (1) | AU6781000A (cs) |
| BR (1) | BR0013843A (cs) |
| CZ (1) | CZ2002931A3 (cs) |
| MX (1) | MXPA02002715A (cs) |
| MY (1) | MY135836A (cs) |
| WO (1) | WO2001019772A1 (cs) |
| ZA (1) | ZA200201553B (cs) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004038013A1 (de) * | 2004-08-04 | 2006-03-16 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| JP2011510000A (ja) * | 2008-01-18 | 2011-03-31 | アーケマ・インコーポレイテッド | アクリレートのヘビーエンドからスルホン酸触媒およびノーブル・プロダクツを回収するためのプロセス |
| KR100970889B1 (ko) * | 2008-04-23 | 2010-07-16 | 강형민 | 분체 고형물 제거공정용 내압소켓 |
| KR100970890B1 (ko) * | 2008-04-23 | 2010-07-16 | 강형민 | 분체 고형물 제거공정용 내열소켓 |
| WO2012071158A1 (en) | 2010-11-22 | 2012-05-31 | Rohm And Haas Company | Acrylate production process |
| WO2024033279A1 (de) * | 2022-08-08 | 2024-02-15 | Basf Se | Kontinuierliches verfahren zur herstellung von n-butyl(meth)acrylat mit einer katalysatorrückführung |
| WO2024033283A1 (de) * | 2022-08-08 | 2024-02-15 | Basf Se | Kontinuierliches verfahren zur herstellung von n-butyl(meth)acrylat mit einer katalysatorrückführung |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3868410A (en) | 1972-08-03 | 1975-02-25 | Celanese Corp | Conversion of oligomeric acrylates to acrylate monomers |
| DE2449811C2 (de) | 1974-10-19 | 1983-01-05 | Hoechst Ag, 6000 Frankfurt | Verfahren zur kontinuierlichen Herstellung von dibutylätherfreiem n-Butylacrylat |
| DE2552987C2 (de) | 1975-11-26 | 1983-09-29 | Hoechst Ag, 6230 Frankfurt | Verfahren zur kontinuierlichen Herstellung ätherfreier Acrylsäurealkylester |
| US4814493A (en) | 1983-07-05 | 1989-03-21 | Hoechst Celanese Corporation | Process for production of alkyl acrylates |
| DE4436242A1 (de) | 1994-10-11 | 1996-04-18 | Basf Ag | Verfahren zur Abtrennung eines (Meth)acrylsäurediesters eines C¶4¶- bis C¶6¶-Alkandiols aus einem Gemisch, das im wesentlichen aus dem C¶4¶- bis C¶-¶¶6¶-Alkandiol, dem (Meth)acrylsäuremonoester des C¶4¶- bis C¶6¶-Alkandiols und dem (Meth)acrylsäurediester des C¶4¶- C¶6¶-Alkandiols besteht |
| DE19510891A1 (de) | 1995-03-24 | 1996-09-26 | Basf Ag | Verfahren zur kontinuierlicheen Herstellung von Alkylestern der (Meth)acrylsäure |
| DE19604252A1 (de) * | 1996-02-06 | 1997-08-07 | Basf Ag | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von Alkylestern der (Meth)acrylsäure |
| US5877345A (en) * | 1997-02-07 | 1999-03-02 | Rohm And Haas Company | Process for producing butyl acrylate |
| DE69717314T2 (de) * | 1997-05-20 | 2003-08-21 | Union Carbide Chem Plastic | Verfahren zur raffination von butylacrylat |
| ZA974628B (en) | 1997-05-27 | 1998-03-25 | Union Carbide Chem Plastic | Processes for refining butyl acrylate. |
-
1999
- 1999-09-14 US US09/395,410 patent/US6172258B1/en not_active Expired - Fee Related
-
2000
- 2000-08-17 AU AU67810/00A patent/AU6781000A/en not_active Abandoned
- 2000-08-17 CZ CZ2002931A patent/CZ2002931A3/cs unknown
- 2000-08-17 KR KR1020027003435A patent/KR20020026273A/ko not_active Application Discontinuation
- 2000-08-17 BR BR0013843-6A patent/BR0013843A/pt not_active IP Right Cessation
- 2000-08-17 CN CN00812896A patent/CN1374939A/zh active Pending
- 2000-08-17 JP JP2001523353A patent/JP2003509396A/ja active Pending
- 2000-08-17 MX MXPA02002715A patent/MXPA02002715A/es active IP Right Grant
- 2000-08-17 EP EP00955641A patent/EP1212284A1/en not_active Ceased
- 2000-08-17 WO PCT/US2000/022573 patent/WO2001019772A1/en not_active Application Discontinuation
- 2000-09-12 MY MYPI20004229A patent/MY135836A/en unknown
-
2002
- 2002-02-25 ZA ZA200201553A patent/ZA200201553B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CZ2002931A3 (cs) | 2002-07-17 |
| CN1374939A (zh) | 2002-10-16 |
| JP2003509396A (ja) | 2003-03-11 |
| EP1212284A1 (en) | 2002-06-12 |
| WO2001019772A1 (en) | 2001-03-22 |
| MY135836A (en) | 2008-07-31 |
| KR20020026273A (ko) | 2002-04-06 |
| AU6781000A (en) | 2001-04-17 |
| US6172258B1 (en) | 2001-01-09 |
| MXPA02002715A (es) | 2002-07-30 |
| BR0013843A (pt) | 2002-05-14 |
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