CN104053643B - 通过酯交换制备丙烯酸2-辛基酯的方法 - Google Patents
通过酯交换制备丙烯酸2-辛基酯的方法 Download PDFInfo
- Publication number
- CN104053643B CN104053643B CN201380006270.7A CN201380006270A CN104053643B CN 104053643 B CN104053643 B CN 104053643B CN 201380006270 A CN201380006270 A CN 201380006270A CN 104053643 B CN104053643 B CN 104053643B
- Authority
- CN
- China
- Prior art keywords
- acrylate
- column
- octanol
- catalyst
- distillation
- 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.)
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- HZLFQUWNZMMHQM-UHFFFAOYSA-N piperazin-1-ylmethanol Chemical compound OCN1CCNCC1 HZLFQUWNZMMHQM-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 43
- 238000005809 transesterification reaction Methods 0.000 title claims abstract description 26
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 claims abstract description 98
- 238000004821 distillation Methods 0.000 claims abstract description 52
- 239000003054 catalyst Substances 0.000 claims abstract description 48
- -1 2-octyl Chemical group 0.000 claims abstract description 28
- 238000000926 separation method Methods 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000000746 purification Methods 0.000 claims abstract description 11
- 239000003112 inhibitor Substances 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 20
- 239000000047 product Substances 0.000 claims description 19
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 238000004064 recycling Methods 0.000 claims description 10
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 9
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 9
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 238000000605 extraction Methods 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-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
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 229960002887 deanol Drugs 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- QWQNFXDYOCUEER-UHFFFAOYSA-N 2,3-ditert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C QWQNFXDYOCUEER-UHFFFAOYSA-N 0.000 description 1
- KTXWGMUMDPYXNN-UHFFFAOYSA-N 2-ethylhexan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-] KTXWGMUMDPYXNN-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- KVZLHPXEUGJPAH-UHFFFAOYSA-N 2-oxidanylpropanoic acid Chemical compound CC(O)C(O)=O.CC(O)C(O)=O KVZLHPXEUGJPAH-UHFFFAOYSA-N 0.000 description 1
- AODAQIOEZVDQLS-UHFFFAOYSA-N 3,4-ditert-butylbenzene-1,2-diol Chemical class CC(C)(C)C1=CC=C(O)C(O)=C1C(C)(C)C AODAQIOEZVDQLS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PKCKEGFHGRMLNH-UHFFFAOYSA-N octan-2-yl prop-2-enoate Chemical class CCCCCCC(C)OC(=O)C=C PKCKEGFHGRMLNH-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- 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
-
- 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
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 (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1250607 | 2012-01-23 | ||
| FR1250607A FR2985999B1 (fr) | 2012-01-23 | 2012-01-23 | Procede de production d'acrylate de 2-octyle par transesterification |
| FR1256471A FR2986000B1 (fr) | 2012-01-23 | 2012-07-05 | Procede de production d'acrylate de 2-octyle par transesterification |
| FR1256471 | 2012-07-05 | ||
| PCT/FR2013/050078 WO2013110876A1 (fr) | 2012-01-23 | 2013-01-14 | Procede de production d'acrylate de 2-octyle par transesterification |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104053643A CN104053643A (zh) | 2014-09-17 |
| CN104053643B true CN104053643B (zh) | 2015-12-30 |
Family
ID=46634451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380006270.7A Active CN104053643B (zh) | 2012-01-23 | 2013-01-14 | 通过酯交换制备丙烯酸2-辛基酯的方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9018410B2 (enExample) |
| EP (1) | EP2807140B1 (enExample) |
| JP (1) | JP6030150B2 (enExample) |
| KR (1) | KR102017924B1 (enExample) |
| CN (1) | CN104053643B (enExample) |
| BR (1) | BR112014017366B1 (enExample) |
| FR (2) | FR2985999B1 (enExample) |
| MY (1) | MY166181A (enExample) |
| SG (1) | SG11201404333SA (enExample) |
| WO (1) | WO2013110876A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3032198B1 (fr) * | 2015-02-04 | 2017-01-13 | Arkema France | Valorisation de produits nobles dans un procede de production d'ester (meth)acrylique. |
| FR3069538B1 (fr) * | 2017-07-25 | 2020-05-15 | Arkema France | Procede de purification d'esters (meth)acryliques. |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1525953A (zh) * | 2001-06-08 | 2004-09-01 | �����ɷ� | (甲基)丙烯酸酯的制备方法 |
| US6977310B2 (en) * | 2002-01-04 | 2005-12-20 | Roehm Gmbh & Co. Kg | Method for the continuous production of alkyl (meth)acrylates |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0466555A (ja) * | 1990-07-03 | 1992-03-02 | Mitsubishi Gas Chem Co Inc | （メタ）アクリル酸エステルの製造法 |
| JPH11222461A (ja) * | 1998-02-02 | 1999-08-17 | Mitsubishi Rayon Co Ltd | （メタ）アクリル酸エステルの製造方法 |
| FR2777561B1 (fr) * | 1998-04-21 | 2000-06-02 | Atochem Elf Sa | Procede de fabrication en continu de (meth)acrylates de dialkylaminoalkyle |
| PT1294658E (pt) | 2000-06-28 | 2005-07-29 | Zambon Spa | Processo para a preparacao de nitroalcenos |
| DE10301007A1 (de) * | 2003-01-13 | 2004-07-22 | Röhm GmbH & Co. KG | Verbessertes Verfahren zur kontinuierlichen Herstellung von Alkyl(meth)acrylaten mit mehrfacher Katalysatorrezyklierung. |
| FR2934261B1 (fr) * | 2008-07-25 | 2015-04-10 | Arkema France | Procede de synthese d'esters de l'acide acrylique |
-
2012
- 2012-01-23 FR FR1250607A patent/FR2985999B1/fr not_active Expired - Fee Related
- 2012-07-05 FR FR1256471A patent/FR2986000B1/fr not_active Expired - Fee Related
-
2013
- 2013-01-14 WO PCT/FR2013/050078 patent/WO2013110876A1/fr not_active Ceased
- 2013-01-14 US US14/370,223 patent/US9018410B2/en active Active
- 2013-01-14 KR KR1020147022795A patent/KR102017924B1/ko active Active
- 2013-01-14 MY MYPI2014002149A patent/MY166181A/en unknown
- 2013-01-14 SG SG11201404333SA patent/SG11201404333SA/en unknown
- 2013-01-14 CN CN201380006270.7A patent/CN104053643B/zh active Active
- 2013-01-14 BR BR112014017366-4A patent/BR112014017366B1/pt active IP Right Grant
- 2013-01-14 JP JP2014552673A patent/JP6030150B2/ja active Active
- 2013-01-14 EP EP13705205.6A patent/EP2807140B1/fr active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1525953A (zh) * | 2001-06-08 | 2004-09-01 | �����ɷ� | (甲基)丙烯酸酯的制备方法 |
| US6977310B2 (en) * | 2002-01-04 | 2005-12-20 | Roehm Gmbh & Co. Kg | Method for the continuous production of alkyl (meth)acrylates |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2807140A1 (fr) | 2014-12-03 |
| MY166181A (en) | 2018-06-07 |
| US20140371482A1 (en) | 2014-12-18 |
| CN104053643A (zh) | 2014-09-17 |
| EP2807140B1 (fr) | 2015-10-28 |
| SG11201404333SA (en) | 2014-10-30 |
| BR112014017366A8 (pt) | 2017-07-04 |
| FR2986000A1 (fr) | 2013-07-26 |
| KR102017924B1 (ko) | 2019-09-03 |
| WO2013110876A1 (fr) | 2013-08-01 |
| JP6030150B2 (ja) | 2016-11-24 |
| US9018410B2 (en) | 2015-04-28 |
| FR2986000B1 (fr) | 2014-01-31 |
| BR112014017366B1 (pt) | 2020-02-18 |
| JP2015504084A (ja) | 2015-02-05 |
| BR112014017366A2 (pt) | 2017-06-13 |
| FR2985999B1 (fr) | 2014-01-31 |
| KR20140114880A (ko) | 2014-09-29 |
| FR2985999A1 (fr) | 2013-07-26 |
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|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |