TW406070B - Process for producing butyl acrylate - Google Patents
Process for producing butyl acrylate Download PDFInfo
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- TW406070B TW406070B TW086106515A TW86106515A TW406070B TW 406070 B TW406070 B TW 406070B TW 086106515 A TW086106515 A TW 086106515A TW 86106515 A TW86106515 A TW 86106515A TW 406070 B TW406070 B TW 406070B
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- 238000000034 method Methods 0.000 title abstract description 125
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 title abstract description 44
- 230000008569 process Effects 0.000 title abstract description 34
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 125
- 238000005336 cracking Methods 0.000 abstract description 98
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract description 88
- 238000000926 separation method Methods 0.000 abstract description 59
- 238000005886 esterification reaction Methods 0.000 abstract description 30
- 238000011084 recovery Methods 0.000 abstract description 29
- 230000032050 esterification Effects 0.000 abstract description 25
- 239000000376 reactant Substances 0.000 abstract description 12
- 125000005250 alkyl acrylate group Chemical group 0.000 abstract description 7
- 238000010924 continuous production Methods 0.000 abstract description 5
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 345
- 229910001868 water Inorganic materials 0.000 description 340
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 336
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 267
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- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 31
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- 238000009833 condensation Methods 0.000 description 16
- 230000005494 condensation Effects 0.000 description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
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- -1 alkane acrylate Chemical class 0.000 description 9
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- 235000021312 gluten Nutrition 0.000 description 1
- 239000003353 gold alloy Substances 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form
-
- 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
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1033495P | 1995-12-15 | 1995-12-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW406070B true TW406070B (en) | 2000-09-21 |
Family
ID=21745257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW086106515A TW406070B (en) | 1995-12-15 | 1997-05-16 | Process for producing butyl acrylate |
Country Status (11)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI786168B (zh) * | 2017-08-17 | 2022-12-11 | 德商巴地斯顏料化工廠 | 連續製備丙烯酸正丁酯或丙烯酸異丁酯之方法 |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19851984A1 (de) * | 1998-11-11 | 2000-05-18 | Basf Ag | Verfahren zum Verestern von (Meth)acrylsäure mit einem Alkanol |
| DE19922722A1 (de) * | 1999-05-18 | 2000-11-23 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| JP2003521478A (ja) * | 1999-06-17 | 2003-07-15 | ユニオン・カーバイド・ケミカルズ・アンド・プラスティックス・テクノロジー・コーポレイション | 平衡律速反応を行う方法 |
| US6482976B1 (en) | 1999-06-17 | 2002-11-19 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for conducting equilibrium-limited reactions |
| WO2005007609A1 (de) * | 2003-07-11 | 2005-01-27 | Basf Aktiengesellschaft | Thermisches trennverfahren zur abtrennung wenigstens eines (meth)acrylmonomere angereichert enthaltenden stoffstroms |
| RU2259399C2 (ru) * | 2003-10-22 | 2005-08-27 | Федеральное государственное унитарное предприятие "Саратовский научно-исследовательский институт химии и технологий акриловых мономеров и полимеров с опытным заводом" | Способ получения эфиров акриловой кислоты и алифатических спиртов c2-c8 |
| JP2011068648A (ja) * | 2004-04-23 | 2011-04-07 | Sumitomo Chemical Co Ltd | 化学増幅型ポジ型レジスト組成物及び（メタ）アクリル酸誘導体とその製法 |
| CN101932547A (zh) * | 2008-01-18 | 2010-12-29 | 阿科玛股份有限公司 | 用于从丙烯酸酯重尾馏分中回收磺酸催化剂以及贵重产物的方法 |
| JP6030564B2 (ja) | 2010-11-22 | 2016-11-24 | ローム アンド ハース カンパニーＲｏｈｍ Ａｎｄ Ｈａａｓ Ｃｏｍｐａｎｙ | ブチルアクリレートの製造方法 |
| JP5748482B2 (ja) * | 2011-01-14 | 2015-07-15 | 株式会社ダイセル | カルボン酸エステルの製造方法 |
| EP3464233B1 (en) * | 2016-05-25 | 2020-04-29 | Dow Global Technologies Llc | Process for recovering byproducts from mma |
| JP2019156738A (ja) * | 2018-03-09 | 2019-09-19 | 三菱ケミカル株式会社 | （メタ）アクリル酸エステルの製造方法 |
| FR3137090B1 (fr) * | 2022-06-24 | 2024-05-10 | Arkema France | Procede de valorisation de sous-produits lourds issus de la fabrication d’acide acrylique |
| FR3137091B1 (fr) * | 2022-06-24 | 2024-05-10 | Arkema France | Procede de valorisation continu de sous-produits lourds issus de la fabrication d’acide acrylique |
| FR3137089B1 (fr) * | 2022-06-24 | 2024-05-10 | Arkema France | Procede de valorisation de sous-produits lourds issus de la fabrication d’acide acrylique |
| FR3137088B1 (fr) * | 2022-06-24 | 2024-05-10 | Arkema France | Procede de valorisation en batch de sous-produits lourds issus de la fabrication d’acide acrylique |
| CN115490590A (zh) * | 2022-08-29 | 2022-12-20 | 平湖石化有限责任公司 | 带丙烯酸循环的丙烯酸丁酯连续生产工艺 |
Family Cites Families (7)
| 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 |
| US3951756A (en) * | 1974-11-08 | 1976-04-20 | Celanese Corporation | Purification of alkyl esters |
| DE2552987C2 (de) * | 1975-11-26 | 1983-09-29 | Hoechst Ag, 6230 Frankfurt | Verfahren zur kontinuierlichen Herstellung ätherfreier Acrylsäurealkylester |
| US4968834A (en) | 1990-05-07 | 1990-11-06 | Hoechst Celanese Corporation | Recovery of acrylic acid and/or ethyl acrylate from black acid |
| FR2727964B1 (fr) * | 1994-12-12 | 1997-01-24 | Atochem Elf Sa | Procede de recuperation des produits nobles legers contenus dans les residus de distillation des procedes de fabrication de l'acide acrylique et de ses esters |
| DE19547485A1 (de) * | 1995-12-19 | 1996-05-09 | Basf Ag | Verfahren zum Verestern von (Meth)acrylsäure mit einem Alkanol |
-
1996
- 1996-12-02 SG SG9611492A patent/SG81213A1/en unknown
- 1996-12-04 EP EP96308792A patent/EP0779268B1/en not_active Expired - Lifetime
- 1996-12-04 ES ES96308792T patent/ES2177738T3/es not_active Expired - Lifetime
- 1996-12-04 DE DE69634457T patent/DE69634457T2/de not_active Expired - Lifetime
- 1996-12-04 DE DE69621902T patent/DE69621902T2/de not_active Expired - Lifetime
- 1996-12-06 CA CA002192264A patent/CA2192264A1/en not_active Abandoned
- 1996-12-09 KR KR1019960062981A patent/KR970042475A/ko not_active Ceased
- 1996-12-11 CZ CZ963638A patent/CZ363896A3/cs unknown
- 1996-12-12 BR BR9605973A patent/BR9605973A/pt not_active IP Right Cessation
- 1996-12-13 JP JP35293096A patent/JP3941843B2/ja not_active Expired - Lifetime
- 1996-12-15 RU RU96123848/04A patent/RU2161150C2/ru active
-
1997
- 1997-05-16 TW TW086106515A patent/TW406070B/zh not_active IP Right Cessation
-
2007
- 2007-01-04 JP JP2007000210A patent/JP4335925B2/ja not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI786168B (zh) * | 2017-08-17 | 2022-12-11 | 德商巴地斯顏料化工廠 | 連續製備丙烯酸正丁酯或丙烯酸異丁酯之方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| BR9605973A (pt) | 1998-08-25 |
| JPH09208520A (ja) | 1997-08-12 |
| KR970042475A (ko) | 1997-07-24 |
| DE69621902D1 (de) | 2002-07-25 |
| DE69634457T2 (de) | 2006-01-26 |
| ES2177738T3 (es) | 2002-12-16 |
| JP4335925B2 (ja) | 2009-09-30 |
| CZ363896A3 (en) | 1997-07-16 |
| DE69621902T2 (de) | 2003-02-13 |
| SG81213A1 (en) | 2001-06-19 |
| RU2161150C2 (ru) | 2000-12-27 |
| CA2192264A1 (en) | 1997-06-16 |
| EP0779268A1 (en) | 1997-06-18 |
| EP0779268B1 (en) | 2002-06-19 |
| DE69634457D1 (de) | 2005-04-14 |
| JP3941843B2 (ja) | 2007-07-04 |
| JP2007153903A (ja) | 2007-06-21 |
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| GD4A | Issue of patent certificate for granted invention patent | ||
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