FR2509294A1 - Procede de fabrication d'esters de l'acide acrylique ou methacrylique - Google Patents
Procede de fabrication d'esters de l'acide acrylique ou methacrylique Download PDFInfo
- Publication number
- FR2509294A1 FR2509294A1 FR8211987A FR8211987A FR2509294A1 FR 2509294 A1 FR2509294 A1 FR 2509294A1 FR 8211987 A FR8211987 A FR 8211987A FR 8211987 A FR8211987 A FR 8211987A FR 2509294 A1 FR2509294 A1 FR 2509294A1
- Authority
- FR
- France
- Prior art keywords
- acid
- acrylic
- esterification
- methacrylic
- column
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 21
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 58
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 56
- 239000002253 acid Substances 0.000 claims abstract description 36
- 238000004821 distillation Methods 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 238000005886 esterification reaction Methods 0.000 claims abstract description 25
- 230000032050 esterification Effects 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 239000007858 starting material Substances 0.000 claims abstract description 7
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims abstract description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 6
- 239000003377 acid catalyst Substances 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 54
- 150000002148 esters Chemical class 0.000 claims description 28
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 23
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 20
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 11
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 11
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 10
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 description 16
- 238000009835 boiling Methods 0.000 description 13
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- -1 acrylic ester Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000012607 strong cation exchange resin Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000008096 xylene 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
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S203/00—Distillation: processes, separatory
- Y10S203/22—Accessories
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10622881A JPS588042A (ja) | 1981-07-09 | 1981-07-09 | アクリル酸メチルの蒸留方法 |
| JP11778681A JPS5821647A (ja) | 1981-07-29 | 1981-07-29 | アクリル酸エチルの蒸留方法 |
| JP17455781A JPS5877845A (ja) | 1981-11-02 | 1981-11-02 | アクリル酸エステルまたはメタクリル酸エステルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2509294A1 true FR2509294A1 (fr) | 1983-01-14 |
| FR2509294B1 FR2509294B1 (enExample) | 1984-08-17 |
Family
ID=27310678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8211987A Granted FR2509294A1 (fr) | 1981-07-09 | 1982-07-08 | Procede de fabrication d'esters de l'acide acrylique ou methacrylique |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4464229A (enExample) |
| BR (1) | BR8203983A (enExample) |
| FR (1) | FR2509294A1 (enExample) |
| MX (1) | MX163005B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5386052A (en) * | 1993-03-31 | 1995-01-31 | Mitsubishi Petrochemical Company Limited | Process for producing acrylic or methacrylic esters |
| WO2015040298A2 (fr) | 2013-09-23 | 2015-03-26 | Arkema France | Procede d'extraction liquide-liquide pour la production d'esters acryliques |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5236559A (en) * | 1993-01-22 | 1993-08-17 | Lloyd Berg | Separation of hexane from vinyl acetate and methyl acrylate by extractive distillation |
| US5435892A (en) * | 1993-08-30 | 1995-07-25 | Mitsubishi Rayon Co., Ltd. | Process for separating methanol and methyl acrylate or methyl methacrylate |
| DE19501326A1 (de) * | 1995-01-18 | 1996-07-25 | Basf Ag | Verfahren der rektifikativen Abtrennung von (Meth)acrylsäure aus einem (Meth)acrylsäure als Hauptbestandteil und niedere Aldehyde als Nebenbestandteile enthaltenden Gemisch in einer aus Abtriebsteil und Verstärkerteil bestehenden Rektifiaktionskolonne |
| US5877345A (en) * | 1997-02-07 | 1999-03-02 | Rohm And Haas Company | Process for producing butyl acrylate |
| DE10144490A1 (de) * | 2001-09-10 | 2003-03-27 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| US20050107629A1 (en) * | 2003-11-17 | 2005-05-19 | Hershberger Brian L. | Method for producing ethyl acrylate |
| JP2016516732A (ja) | 2013-03-18 | 2016-06-09 | エボニック レーム ゲゼルシャフト ミット ベシュレンクテル ハフツングＥｖｏｎｉｋ Ｒｏｅｈｍ ＧｍｂＨ | メタクリル酸及びメタクリル酸エステルの製造方法 |
| FR3012447B1 (fr) | 2013-10-29 | 2017-01-20 | Arkema France | Procede de production d'esters (meth)acryliques legers |
| US10807063B1 (en) | 2019-12-31 | 2020-10-20 | Industrial Technology Research Institute | Device and method for continuously manufacturing acrylate compound |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2202876A1 (en) * | 1972-10-10 | 1974-05-10 | Nippon Catalytic Chem Ind | Acrylic or methacrylic esters - by continuous esterification of acrylic or methacrylic acid with methanol or ethanol |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4830257B1 (enExample) * | 1969-02-06 | 1973-09-18 | ||
| US3743672A (en) * | 1970-05-27 | 1973-07-03 | Halcon International Inc | Separation of water in alkylene glycol mono and diester purification by azeotropic distillation |
| DE2226829A1 (de) * | 1972-06-02 | 1973-12-20 | Knapsack Ag | Verfahren zur herstellung von acrylsaeureestern |
| US3951756A (en) * | 1974-11-08 | 1976-04-20 | Celanese Corporation | Purification of alkyl esters |
| US4076950A (en) * | 1976-07-19 | 1978-02-28 | Rohm And Haas Company | Process for manufacture of alkyl esters of aliphatic carboxylic acids |
| NL7807420A (nl) * | 1977-07-22 | 1979-01-24 | Mitsubishi Chem Ind | Werkwijze voor het afscheiden van methacrylzuur uit een mengsel, dat water, methanol, methacrylzuur en methylmethacrylaat bevat. |
| JPS54106412A (en) * | 1978-02-08 | 1979-08-21 | Kyowa Yuka Kk | Method of purifying ester |
| JPS54122210A (en) * | 1978-03-15 | 1979-09-21 | Sumitomo Chem Co Ltd | Recovery of acrylic acid and alcohol |
| JPS55105645A (en) * | 1979-02-07 | 1980-08-13 | Toyo Soda Mfg Co Ltd | Continuous esterification of methacrylic acid |
-
1982
- 1982-06-29 US US06/393,484 patent/US4464229A/en not_active Expired - Lifetime
- 1982-07-08 FR FR8211987A patent/FR2509294A1/fr active Granted
- 1982-07-08 BR BR8203983A patent/BR8203983A/pt unknown
- 1982-07-08 MX MX193511A patent/MX163005B/es unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2202876A1 (en) * | 1972-10-10 | 1974-05-10 | Nippon Catalytic Chem Ind | Acrylic or methacrylic esters - by continuous esterification of acrylic or methacrylic acid with methanol or ethanol |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5386052A (en) * | 1993-03-31 | 1995-01-31 | Mitsubishi Petrochemical Company Limited | Process for producing acrylic or methacrylic esters |
| WO2015040298A2 (fr) | 2013-09-23 | 2015-03-26 | Arkema France | Procede d'extraction liquide-liquide pour la production d'esters acryliques |
Also Published As
| Publication number | Publication date |
|---|---|
| MX163005B (es) | 1991-07-31 |
| FR2509294B1 (enExample) | 1984-08-17 |
| US4464229A (en) | 1984-08-07 |
| BR8203983A (pt) | 1983-07-05 |
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