DE2449811C2 - Verfahren zur kontinuierlichen Herstellung von dibutylätherfreiem n-Butylacrylat - Google Patents
Verfahren zur kontinuierlichen Herstellung von dibutylätherfreiem n-ButylacrylatInfo
- Publication number
- DE2449811C2 DE2449811C2 DE2449811A DE2449811A DE2449811C2 DE 2449811 C2 DE2449811 C2 DE 2449811C2 DE 2449811 A DE2449811 A DE 2449811A DE 2449811 A DE2449811 A DE 2449811A DE 2449811 C2 DE2449811 C2 DE 2449811C2
- Authority
- DE
- Germany
- Prior art keywords
- butyl acrylate
- butanol
- acrylic acid
- distillation zone
- weight
- 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.)
- Expired
Links
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 title claims description 46
- 238000000034 method Methods 0.000 title claims description 8
- 238000010924 continuous production Methods 0.000 title claims description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 82
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 51
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 238000004821 distillation Methods 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 19
- 239000008346 aqueous phase Substances 0.000 claims description 8
- 238000005886 esterification reaction Methods 0.000 claims description 8
- 230000032050 esterification Effects 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 5
- -1 sulfonic acid cation Chemical class 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000010626 work up procedure Methods 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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 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 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- VENJJOGQEGHFPI-UHFFFAOYSA-N butyl prop-2-enoate;2-methylidenehexanoic acid Chemical compound CCCCOC(=O)C=C.CCCCC(=C)C(O)=O VENJJOGQEGHFPI-UHFFFAOYSA-N 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XAEWZDYWZHIUCT-UHFFFAOYSA-N desipramine hydrochloride Chemical compound [H+].[Cl-].C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 XAEWZDYWZHIUCT-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 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)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2449811A DE2449811C2 (de) | 1974-10-19 | 1974-10-19 | Verfahren zur kontinuierlichen Herstellung von dibutylätherfreiem n-Butylacrylat |
| GB3574775A GB1471800A (en) | 1974-10-19 | 1975-08-29 | Continuous production of n-butyl acrylate free from dibutyl ether |
| CA237,224A CA1064959A (en) | 1974-10-19 | 1975-10-07 | Continuous production of n-butylacrylate free from dibutylether |
| US05/622,263 US4012439A (en) | 1974-10-19 | 1975-10-14 | Continuous production of n-butylacrylate free from dibutylether |
| BE160952A BE834530A (fr) | 1974-10-19 | 1975-10-15 | Procede de preparation en continu d'acrylate de n-butyle exempt d'oxyde de dibutyle |
| NL7512164A NL7512164A (nl) | 1974-10-19 | 1975-10-16 | Werkwijze voor de continue bereiding van dibu- tylethervrij n-butylacrylaat. |
| FR7531889A FR2288081A1 (fr) | 1974-10-19 | 1975-10-17 | Procede de preparation en continu d'acrylate de n-butyle exempt d'oxyde de dibutyle |
| JP50125245A JPS5165712A (enExample) | 1974-10-19 | 1975-10-17 | |
| IT51815/75A IT1047838B (it) | 1974-10-19 | 1975-10-17 | Procedimento ed impianto per la produzione continua di n butila crilato esente da etere dibutilico |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2449811A DE2449811C2 (de) | 1974-10-19 | 1974-10-19 | Verfahren zur kontinuierlichen Herstellung von dibutylätherfreiem n-Butylacrylat |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2449811A1 DE2449811A1 (de) | 1976-04-29 |
| DE2449811C2 true DE2449811C2 (de) | 1983-01-05 |
Family
ID=5928711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2449811A Expired DE2449811C2 (de) | 1974-10-19 | 1974-10-19 | Verfahren zur kontinuierlichen Herstellung von dibutylätherfreiem n-Butylacrylat |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4012439A (enExample) |
| JP (1) | JPS5165712A (enExample) |
| BE (1) | BE834530A (enExample) |
| CA (1) | CA1064959A (enExample) |
| DE (1) | DE2449811C2 (enExample) |
| FR (1) | FR2288081A1 (enExample) |
| GB (1) | GB1471800A (enExample) |
| IT (1) | IT1047838B (enExample) |
| NL (1) | NL7512164A (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51146418A (en) * | 1975-06-10 | 1976-12-16 | Nippon Zeon Co Ltd | Purification of methacrylic esters |
| DE2548561C2 (de) * | 1975-10-30 | 1983-09-29 | Hoechst Ag, 6230 Frankfurt | Verfahren zur kontinuierlichen Herstellung dioctylätherfreien 2-Äthyl- hexylacrylats |
| DE2552987C2 (de) * | 1975-11-26 | 1983-09-29 | Hoechst Ag, 6230 Frankfurt | Verfahren zur kontinuierlichen Herstellung ätherfreier Acrylsäurealkylester |
| JPS6357554A (ja) * | 1986-08-29 | 1988-03-12 | Mitsubishi Rayon Co Ltd | アクリル酸又はメタクリル酸のフエニルエステル類の製法 |
| DE3728242A1 (de) * | 1987-08-25 | 1989-03-09 | Basf Ag | Verfahren zur herstellung von carbonsaeureestern |
| FR2723089B1 (fr) | 1994-07-28 | 1996-09-06 | Atochem Elf Sa | Procede de fabrication de l'acrylate de butyle par esterification directe |
| SG81213A1 (en) * | 1995-12-15 | 2001-06-19 | Rohm & Haas | Process for producing butyle acrylate |
| EP1182189B1 (en) * | 1995-12-15 | 2005-03-09 | Rohm And Haas Company | Process for recovering butyl acrylate substantially free from acrylic acid |
| WO1998052904A1 (en) * | 1997-05-20 | 1998-11-26 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for refining butylacrylate |
| US6605738B1 (en) | 1996-05-29 | 2003-08-12 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for refining butyl acrylate |
| CN1069893C (zh) * | 1996-08-03 | 2001-08-22 | 中国石化齐鲁石油化工公司 | 甲基丙烯酸甲酯和乙酯的制造方法 |
| US5877345A (en) * | 1997-02-07 | 1999-03-02 | Rohm And Haas Company | Process for producing butyl acrylate |
| US6180820B1 (en) * | 1999-09-14 | 2001-01-30 | Celanese International Corporation | Process for the production and purification of N-butyl acrylate |
| US6172258B1 (en) | 1999-09-14 | 2001-01-09 | Celanese International Corporation | Process for the production and purification of n-butyl acrylate |
| JP4715106B2 (ja) * | 2004-04-01 | 2011-07-06 | 三菱化学株式会社 | （メタ）アクリル酸誘導体の製造方法 |
| CN100443460C (zh) * | 2005-12-27 | 2008-12-17 | 中国石油化工股份有限公司 | 一种羧酸酯的制备方法 |
| 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 |
| CN102675098A (zh) * | 2012-05-29 | 2012-09-19 | 江门谦信化工发展有限公司 | 一种丙烯酸丁酯连续生产新工艺 |
| CN102863337A (zh) * | 2012-09-18 | 2013-01-09 | 太仓市运通化工厂 | 一种1,6-己二醇二丙烯酸酯的合成方法 |
| CN104529759A (zh) * | 2014-11-28 | 2015-04-22 | 江门谦信化工发展有限公司 | 一种节能环保的丙烯酸丁酯的生产方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB841521A (en) * | 1955-09-28 | 1960-07-20 | Wakefield & Co Ltd C C | Improvements in or relating to processes for the preparation of esters of acrylic and methacrylic acids |
| NL296301A (enExample) * | 1962-08-08 | |||
| GB1003007A (en) * | 1963-05-30 | 1965-09-02 | Distillers Co Yeast Ltd | Improvements in or relating to the production of ethyl acrylate |
-
1974
- 1974-10-19 DE DE2449811A patent/DE2449811C2/de not_active Expired
-
1975
- 1975-08-29 GB GB3574775A patent/GB1471800A/en not_active Expired
- 1975-10-07 CA CA237,224A patent/CA1064959A/en not_active Expired
- 1975-10-14 US US05/622,263 patent/US4012439A/en not_active Expired - Lifetime
- 1975-10-15 BE BE160952A patent/BE834530A/xx not_active IP Right Cessation
- 1975-10-16 NL NL7512164A patent/NL7512164A/xx not_active Application Discontinuation
- 1975-10-17 FR FR7531889A patent/FR2288081A1/fr active Granted
- 1975-10-17 JP JP50125245A patent/JPS5165712A/ja active Pending
- 1975-10-17 IT IT51815/75A patent/IT1047838B/it active
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7512164A (nl) | 1976-04-21 |
| GB1471800A (en) | 1977-04-27 |
| CA1064959A (en) | 1979-10-23 |
| DE2449811A1 (de) | 1976-04-29 |
| IT1047838B (it) | 1980-10-20 |
| JPS5165712A (enExample) | 1976-06-07 |
| US4012439A (en) | 1977-03-15 |
| FR2288081B1 (enExample) | 1980-08-01 |
| FR2288081A1 (fr) | 1976-05-14 |
| BE834530A (fr) | 1976-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |