BR112017007905B1 - Processo para a produção de metil metacrilato - Google Patents
Processo para a produção de metil metacrilato Download PDFInfo
- Publication number
- BR112017007905B1 BR112017007905B1 BR112017007905-4A BR112017007905A BR112017007905B1 BR 112017007905 B1 BR112017007905 B1 BR 112017007905B1 BR 112017007905 A BR112017007905 A BR 112017007905A BR 112017007905 B1 BR112017007905 B1 BR 112017007905B1
- Authority
- BR
- Brazil
- Prior art keywords
- stream
- aqueous
- phase
- mma
- polymer
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 40
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 69
- 229920000642 polymer Polymers 0.000 claims description 50
- 239000012071 phase Substances 0.000 claims description 31
- 239000010410 layer Substances 0.000 claims description 30
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 22
- 238000005886 esterification reaction Methods 0.000 claims description 17
- 238000005191 phase separation Methods 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000008346 aqueous phase Substances 0.000 claims description 14
- DZGUJOWBVDZNNF-UHFFFAOYSA-N azanium;2-methylprop-2-enoate Chemical compound [NH4+].CC(=C)C([O-])=O DZGUJOWBVDZNNF-UHFFFAOYSA-N 0.000 claims description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 9
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 239000012044 organic layer Substances 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 239000012263 liquid product Substances 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 239000012431 aqueous reaction media Substances 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 238000010926 purge Methods 0.000 description 20
- 239000000047 product Substances 0.000 description 18
- 230000032050 esterification Effects 0.000 description 11
- 239000003112 inhibitor Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 9
- 238000005336 cracking Methods 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- QYPPRTNMGCREIM-UHFFFAOYSA-N methylarsonic acid Chemical compound C[As](O)(O)=O QYPPRTNMGCREIM-UHFFFAOYSA-N 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920002972 Acrylic fiber Polymers 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- -1 Methacrylate ester Chemical class 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 229920001600 hydrophobic polymer Polymers 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 150000003464 sulfur compounds Chemical class 0.000 description 2
- DRYMMXUBDRJPDS-UHFFFAOYSA-N 2-hydroxy-2-methylpropanamide Chemical compound CC(C)(O)C(N)=O DRYMMXUBDRJPDS-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical group CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003090 exacerbative effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/18—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group
- C07C67/20—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group from amides or lactams
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/42—Regulation; Control
- B01D3/4211—Regulation; Control of columns
- B01D3/4294—Feed stream
-
- 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
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/18—Stationary reactors having moving elements inside
- B01J19/1868—Stationary reactors having moving elements inside resulting in a loop-type movement
- B01J19/1875—Stationary reactors having moving elements inside resulting in a loop-type movement internally, i.e. the mixture circulating inside the vessel such that the upwards stream is separated physically from the downwards stream(s)
-
- 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
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- 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
-
- 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
- B01J2219/00027—Process aspects
- B01J2219/0004—Processes in series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462068996P | 2014-10-27 | 2014-10-27 | |
| US62/068,996 | 2014-10-27 | ||
| PCT/US2015/055211 WO2016069252A1 (en) | 2014-10-27 | 2015-10-13 | Reduced fouling process for the production of methyl methacrylate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112017007905A2 BR112017007905A2 (pt) | 2018-01-23 |
| BR112017007905B1 true BR112017007905B1 (pt) | 2021-11-30 |
Family
ID=54347907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112017007905-4A BR112017007905B1 (pt) | 2014-10-27 | 2015-10-13 | Processo para a produção de metil metacrilato |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10294190B2 (enExample) |
| EP (1) | EP3212603B1 (enExample) |
| JP (1) | JP6740220B2 (enExample) |
| CN (1) | CN107074723A (enExample) |
| BR (1) | BR112017007905B1 (enExample) |
| WO (1) | WO2016069252A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105968012B (zh) * | 2016-07-04 | 2019-11-08 | 江苏斯尔邦石化有限公司 | 一种mma洗涤塔酸度消除方法及用于该方法的装置 |
| KR102482504B1 (ko) * | 2018-04-23 | 2022-12-30 | 주식회사 엘지화학 | t-부틸 메타크릴레이트의 제조방법 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2472487A (en) | 1946-03-29 | 1949-06-07 | Standard Oil Dev Co | Butadiene extraction |
| NL252505A (enExample) | 1959-07-31 | |||
| NL266444A (enExample) | 1960-06-29 | |||
| US3821286A (en) | 1971-10-05 | 1974-06-28 | American Cyanamid Co | Process for the production of methyl methacrylate |
| IT1257282B (it) * | 1992-03-16 | 1996-01-12 | Processo migliorato per la produzione di metilmetacrilato monomero da acetoncianidrina | |
| US5403963A (en) | 1994-02-01 | 1995-04-04 | Shell Oil Company | Process for the production of lower alcohols |
| KR960000850A (ko) * | 1994-06-06 | 1996-01-25 | 사토 아키오 | 메타크릴산메틸의 연속제조방법 |
| EP0999200B1 (en) | 1998-11-04 | 2002-07-17 | Rohm And Haas Company | Process for the high yield production of methyl methacrylate or methacrylic acid |
| AU2002354063A1 (en) * | 2001-11-27 | 2003-06-10 | Mitsubishi Chemical Corporation | Process for producing (meth)acrylic ester |
| JP2003226672A (ja) * | 2001-11-27 | 2003-08-12 | Mitsubishi Chemicals Corp | (メタ)アクリル酸エステルの製造方法 |
| ZA200303241B (en) | 2002-05-01 | 2003-11-04 | Rohm & Haas | Improved process for methacrylic acid and methcrylic acid ester production. |
| DE102006058250A1 (de) | 2006-12-08 | 2008-06-12 | Evonik Röhm Gmbh | Integriertes Verfahren und Vorrichtung zur Herstellung von Methacrylsäureestern aus Aceton und Blausäure |
| DE102011076642A1 (de) * | 2011-05-27 | 2012-11-29 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Methacrylsäure |
| JP6036400B2 (ja) * | 2013-02-26 | 2016-11-30 | 三菱化学株式会社 | (メタ)アクリル酸エステルの製造方法 |
-
2015
- 2015-10-13 US US15/521,421 patent/US10294190B2/en active Active
- 2015-10-13 JP JP2017518427A patent/JP6740220B2/ja active Active
- 2015-10-13 WO PCT/US2015/055211 patent/WO2016069252A1/en not_active Ceased
- 2015-10-13 BR BR112017007905-4A patent/BR112017007905B1/pt active IP Right Grant
- 2015-10-13 EP EP15784898.7A patent/EP3212603B1/en active Active
- 2015-10-13 CN CN201580056111.7A patent/CN107074723A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BR112017007905A2 (pt) | 2018-01-23 |
| US20170298000A1 (en) | 2017-10-19 |
| EP3212603B1 (en) | 2020-11-25 |
| EP3212603A1 (en) | 2017-09-06 |
| CN107074723A (zh) | 2017-08-18 |
| JP6740220B2 (ja) | 2020-08-12 |
| US10294190B2 (en) | 2019-05-21 |
| WO2016069252A1 (en) | 2016-05-06 |
| JP2017531656A (ja) | 2017-10-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B06U | Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette] | ||
| B07A | Application suspended after technical examination (opinion) [chapter 7.1 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 13/10/2015, OBSERVADAS AS CONDICOES LEGAIS. |