BR112014017366B1 - Processo de produção de acrilato de 2-octila por transesterificação - Google Patents
Processo de produção de acrilato de 2-octila por transesterificação Download PDFInfo
- Publication number
- BR112014017366B1 BR112014017366B1 BR112014017366-4A BR112014017366A BR112014017366B1 BR 112014017366 B1 BR112014017366 B1 BR 112014017366B1 BR 112014017366 A BR112014017366 A BR 112014017366A BR 112014017366 B1 BR112014017366 B1 BR 112014017366B1
- Authority
- BR
- Brazil
- Prior art keywords
- acrylate
- catalyst
- column
- octanol
- octyl acrylate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 40
- 238000005809 transesterification reaction Methods 0.000 title claims abstract description 28
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims description 34
- 238000004519 manufacturing process Methods 0.000 title abstract description 17
- 229950004492 octil Drugs 0.000 title 1
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 claims abstract description 97
- 239000003054 catalyst Substances 0.000 claims abstract description 51
- 238000004821 distillation Methods 0.000 claims abstract description 51
- HZLFQUWNZMMHQM-UHFFFAOYSA-N piperazin-1-ylmethanol Chemical compound OCN1CCNCC1 HZLFQUWNZMMHQM-UHFFFAOYSA-N 0.000 claims abstract description 50
- -1 2-octyl Chemical group 0.000 claims abstract description 25
- 238000000746 purification Methods 0.000 claims abstract description 12
- 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 11
- 238000000926 separation method Methods 0.000 claims abstract description 9
- 238000010924 continuous production Methods 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 45
- 239000003112 inhibitor Substances 0.000 claims description 33
- 238000006116 polymerization reaction Methods 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 239000000047 product Substances 0.000 claims description 20
- 239000011541 reaction mixture Substances 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 8
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000002148 esters Chemical class 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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-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
- 238000009835 boiling Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000012855 volatile organic compound Substances 0.000 description 3
- 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
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229960002887 deanol Drugs 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
- BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical group CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 description 1
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical class OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 1
- 208000005156 Dehydration Diseases 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 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
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- DTDMYWXTWWFLGJ-UHFFFAOYSA-N decan-4-ol Chemical compound CCCCCCC(O)CCC DTDMYWXTWWFLGJ-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction 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
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([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
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 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
- 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
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000000126 substance 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
- 239000005418 vegetable 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
- C07C67/28—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 |
| FR1256471 | 2012-07-05 | ||
| FR1256471A FR2986000B1 (fr) | 2012-01-23 | 2012-07-05 | Procede de production d'acrylate de 2-octyle par transesterification |
| PCT/FR2013/050078 WO2013110876A1 (fr) | 2012-01-23 | 2013-01-14 | Procede de production d'acrylate de 2-octyle par transesterification |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| BR112014017366A2 BR112014017366A2 (pt) | 2017-06-13 |
| BR112014017366A8 BR112014017366A8 (pt) | 2017-07-04 |
| BR112014017366B1 true BR112014017366B1 (pt) | 2020-02-18 |
Family
ID=46634451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112014017366-4A BR112014017366B1 (pt) | 2012-01-23 | 2013-01-14 | Processo de produção de acrilato de 2-octila por transesterificação |
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. |
Family Cites Families (8)
| 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 |
| DK1294658T3 (da) | 2000-06-28 | 2005-06-27 | Zambon Spa | Fremgangsmåde til fremstilling af nitroalkener |
| DE10127939A1 (de) * | 2001-06-08 | 2002-05-29 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| DE10200171A1 (de) * | 2002-01-04 | 2003-07-10 | Roehm Gmbh | Verfahren zur kontinuierlichen Herstellung von Alkyl(meth)acrylaten |
| 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 JP JP2014552673A patent/JP6030150B2/ja active Active
- 2013-01-14 SG SG11201404333SA patent/SG11201404333SA/en unknown
- 2013-01-14 KR KR1020147022795A patent/KR102017924B1/ko active Active
- 2013-01-14 CN CN201380006270.7A patent/CN104053643B/zh active Active
- 2013-01-14 EP EP13705205.6A patent/EP2807140B1/fr active Active
- 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 BR BR112014017366-4A patent/BR112014017366B1/pt active IP Right Grant
- 2013-01-14 MY MYPI2014002149A patent/MY166181A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2986000A1 (fr) | 2013-07-26 |
| JP2015504084A (ja) | 2015-02-05 |
| EP2807140B1 (fr) | 2015-10-28 |
| EP2807140A1 (fr) | 2014-12-03 |
| US20140371482A1 (en) | 2014-12-18 |
| KR102017924B1 (ko) | 2019-09-03 |
| BR112014017366A2 (pt) | 2017-06-13 |
| FR2985999A1 (fr) | 2013-07-26 |
| CN104053643A (zh) | 2014-09-17 |
| SG11201404333SA (en) | 2014-10-30 |
| KR20140114880A (ko) | 2014-09-29 |
| MY166181A (en) | 2018-06-07 |
| US9018410B2 (en) | 2015-04-28 |
| BR112014017366A8 (pt) | 2017-07-04 |
| FR2985999B1 (fr) | 2014-01-31 |
| CN104053643B (zh) | 2015-12-30 |
| FR2986000B1 (fr) | 2014-01-31 |
| JP6030150B2 (ja) | 2016-11-24 |
| WO2013110876A1 (fr) | 2013-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B06F | Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette] | ||
| B06T | Formal requirements before examination [chapter 6.20 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 14/01/2013, OBSERVADAS AS CONDICOES LEGAIS. |