SK21497A3 - Process for preparing refined acrylic acid esters - Google Patents

Process for preparing refined acrylic acid esters Download PDF

Info

Publication number: SK21497A3
Authority: SK; Slovakia
Prior art keywords: distillation; acrylic ester; ppmw; acrylic; distillation column
Prior art date: 1994-08-18

Application number

SK214-97A

Other languages

English (en)

Slovak (sk)

Inventor

Peter Arnoldy

Eric Kragtwijk

Antoon P M Kremers

Original Assignee

Shell Int Research

Priority date (The priority date 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 date listed.)

1994-08-18

Filing date

1995-08-15

Publication date

1997-11-05

1995-08-15 Application filed by Shell Int Research filed Critical Shell Int Research

1997-11-05 Publication of SK21497A3 publication Critical patent/SK21497A3/sk

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 8
125000005396 acrylic acid ester group Chemical group 0.000 title claims description 13
239000003112 inhibitor Substances 0.000 claims abstract description 37
-1 acrylic ester Chemical class 0.000 claims abstract description 26
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims abstract description 25
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 21
229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 16
239000001301 oxygen Substances 0.000 claims abstract description 16
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 15
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims abstract description 7
238000004821 distillation Methods 0.000 claims description 62
QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 37
238000000034 method Methods 0.000 claims description 28
239000003054 catalyst Substances 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
239000003446 ligand Substances 0.000 claims description 9
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 6
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 4
150000001450 anions Chemical class 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
239000002815 homogeneous catalyst Substances 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 4
230000001476 alcoholic effect Effects 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
239000007789 gas Substances 0.000 claims description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 2
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 2
WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 claims description 2
229940017219 methyl propionate Drugs 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 19
239000004926 polymethyl methacrylate Substances 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
238000006116 polymerization reaction Methods 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 9
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 8
229910052763 palladium Inorganic materials 0.000 description 8
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 7
229920000642 polymer Polymers 0.000 description 5
239000000047 product Substances 0.000 description 5
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
238000005810 carbonylation reaction Methods 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000013256 coordination polymer Substances 0.000 description 3
238000001514 detection method Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000012043 crude product Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001183 hydrocarbyl group Chemical group 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
MCVVUJPXSBQTRZ-ONEGZZNKSA-N methyl (e)-but-2-enoate Chemical compound COC(=O)\C=C\C MCVVUJPXSBQTRZ-ONEGZZNKSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
229950000688 phenothiazine Drugs 0.000 description 2
238000000746 purification Methods 0.000 description 2
CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
GPASWZHHWPVSRG-UHFFFAOYSA-N 2,5-dimethylbenzene-1,4-diol Chemical compound CC1=CC(O)=C(C)C=C1O GPASWZHHWPVSRG-UHFFFAOYSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
238000005602 Reppe reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000001944 continuous distillation Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
SVABQOITNJTVNJ-UHFFFAOYSA-N diphenyl-2-pyridylphosphine Chemical compound C1=CC=CC=C1P(C=1N=CC=CC=1)C1=CC=CC=C1 SVABQOITNJTVNJ-UHFFFAOYSA-N 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
125000005397 methacrylic acid ester group Chemical group 0.000 description 1
125000005395 methacrylic acid group Chemical class 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
150000005217 methyl ethers Chemical class 0.000 description 1
239000000178 monomer Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
230000037361 pathway Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 1
238000011282 treatment Methods 0.000 description 1
230000000007 visual effect Effects 0.000 description 1

Classifications

- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
- C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond
- 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)
Crystallography & Structural Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SK214-97A 1994-08-18 1995-08-15 Process for preparing refined acrylic acid esters SK21497A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP94202354		1994-08-18
PCT/EP1995/003246 WO1996006066A1 (en)	1994-08-18	1995-08-15	Process for preparing refined acrylic esters

Publications (1)

Publication Number	Publication Date
SK21497A3 true SK21497A3 (en)	1997-11-05

Family

ID=8217104

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK214-97A SK21497A3 (en)	1994-08-18	1995-08-15	Process for preparing refined acrylic acid esters

Country Status (13)

Country	Link
US (1)	US5968322A (de)
EP (1)	EP0804407B1 (de)
JP (1)	JPH10504553A (de)
KR (1)	KR970704662A (de)
AU (1)	AU3384395A (de)
BR (1)	BR9508592A (de)
CA (1)	CA2197666A1 (de)
DE (1)	DE69514839T2 (de)
ES (1)	ES2143067T3 (de)
MX (1)	MX9701236A (de)
SK (1)	SK21497A3 (de)
TW (1)	TW360637B (de)
WO (1)	WO1996006066A1 (de)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19746689A1 (de) *	1997-10-22	1999-04-29	Basf Ag	Verfahren zur Herstellung von (Meth)acrylsäure
JP4143218B2 (ja) *	1999-04-23	2008-09-03	株式会社日本触媒	薄膜式蒸発装置における重合防止方法および薄膜式蒸発装置
FR2801306B1 (fr)	1999-11-24	2001-12-28	Atofina	Procede de purification des monomeres (meth) acryliques par distillation
TWI250149B (en) *	2000-10-23	2006-03-01	Nippon Catalytic Chem Ind	Composition of vinyl ether group-containing (meth)acrylic acid ester and production method thereof
TWI288756B (en) *	2001-12-24	2007-10-21	Ind Tech Res Inst	Catalyst composition for living free radical polymerization and process for polymerizing (meth)acrylic, vinyl, vinylidene, and diene monomers using the catalyst composition
BRPI0416962A8 (pt) *	2003-11-28	2017-12-19	Mitsubishi Chem Corp	Método de purificação de ácido (met) acrílico
JPWO2005102984A1 (ja) *	2004-04-26	2008-03-13	ダイキン工業株式会社	含フッ素アクリル酸エステルの製造方法
KR100601392B1 (ko)	2004-11-09	2006-07-13	한국화학연구원	에틸렌글리콜디(메타)아크릴레이트의 제조방법
US20080021241A1 (en) *	2004-11-12	2008-01-24	Carlson Curtis I Jr	Process for production of methacrylic acid
CN104557539A (zh) *	2014-12-23	2015-04-29	安徽助成信息科技有限公司	一种丙烯酸甲酯（ma）与丙酸甲酯（mp）的分离方法
RU2723556C2 (ru) *	2015-04-09	2020-06-16	Дайкин Индастриз, Лтд.	Композиция, содержащая производную акриловой кислоты, и способ стабилизации производной акриловой кислоты
CN117203249A (zh)	2021-04-28	2023-12-08	三菱化学株式会社	含有甲基丙烯酸甲酯的组合物
KR20230175270A (ko)	2021-04-28	2023-12-29	미쯔비시 케미컬 주식회사	메타크릴산 메틸 함유 조성물 및 메타크릴산 메틸 중합체의 제조 방법
EP4332124A4 (de)	2021-04-28	2025-03-05	Mitsubishi Chemical Corporation	Methylmethacrylathaltige zusammensetzung und verfahren zur herstellung von methylmethacrylatpolymer
BR112023022410A2 (pt)	2021-04-28	2023-12-26	Mitsubishi Chem Corp	Composição contendo metacrilato de metila e método de produção de polímero de metacrilato de metila
BR112023022353A2 (pt)	2021-04-28	2023-12-26	Mitsubishi Chem Corp	Composição contendo metacrilato de metila e método para produzir polímero de metacrilato de metila
EP4442677A4 (de)	2021-11-30	2025-03-26	Mitsubishi Chemical Corporation	Methylmethacrylathaltige zusammensetzung, speicherverfahren für methylmethacrylathaltige zusammensetzung und herstellungsverfahren für methylmethacrylatpolymer
EP4469513A1 (de) *	2022-01-28	2024-12-04	Basf Se	Lagerung und/oder transport ethylenisch ungesättigter verbindungen
EP4610284A4 (de)	2022-10-28	2026-02-25	Mitsubishi Chem Corp	Monomerzusammensetzung, methacrylharzzusammensetzung und herstellungsverfahren dafür sowie formharzobjekt

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA768651A (en) *		1967-10-03	J. Humphrey William	Process for the preparation of acrylic acid esters
US908001A (en) *	1908-05-12	1908-12-29	Wilhelm Herbst	Fireproof floor construction.
GB920353A (en) *	1959-12-10	1963-03-06	Knapsack Ag	Process for stabilizing acrylic acid alkyl esters
US3666794A (en) *	1969-01-22	1972-05-30	Toyo Soda Mfg Co Ltd	Stabilization of acrylic acid or esters thereof
JPS4915153B1 (de) *	1969-06-06	1974-04-12
GB1307582A (en) *	1969-06-10	1973-02-21	Rohm & Haas	Inhibition of polymerization of acrylic acids
US3812175A (en) *	1970-01-26	1974-05-21	Nat Lead Co	Multiple stage carbonylation process
BE787750A (fr) *	1971-08-20	1973-02-19	Union Carbide Corp	Procede pour inhiber la polymerisation d'acrylates et methacrylates pendant leur distillation
US3988213A (en) *	1972-09-25	1976-10-26	Nippon Shokubai Kagaku Kogyo Co., Ltd.	Method of distilling vinyl compounds
FR2201275A1 (en) *	1972-09-29	1974-04-26	Nippon Catalytic Chem Ind	Distillation of (meth)acrylic monomers - in presence of polymerisation inhibitor in column with perforated plates, and without overflow tube
US4021310A (en) *	1972-12-22	1977-05-03	Nippon Shokubai Kagaku Kogyo Co., Ltd.	Method for inhibiting the polymerization of acrylic acid or its esters
JPS52125116A (en) *	1976-04-12	1977-10-20	Mitsubishi Rayon Co Ltd	Stabilization of methyl methacrylate
JPS59219252A (ja) *	1983-05-30	1984-12-10	Nippon Oil & Fats Co Ltd	アクリル酸エステルまたはメタクリル酸エステルの精製法
GB8432376D0 (en) *	1984-12-21	1985-02-06	Shell Int Research	Carbonylation of acetylenically unsaturated compounds
DE3543115A1 (de) *	1985-12-06	1987-06-11	Degussa	Verfahren zur herstellung von tetrahydrofurfuryl-(2)-methacrylat und dazu geeigneter katalysator
ES2082118T3 (es) *	1991-10-30	1996-03-16	Shell Int Research	Procedimiento para la preparacion de esteres de metacrilato.
EP0571044B1 (de) *	1992-05-20	1997-04-09	Shell Internationale Researchmaatschappij B.V.	Wiedergewinnung von Carbonsäureesterreaktionsprodukten
JP3684582B2 (ja) *	1993-08-09	2005-08-17	三菱化学株式会社	（メタ）アクリル酸又は（メタ）アクリル酸エステルの重合防止方法

1995
- 1995-08-15 JP JP8507767A patent/JPH10504553A/ja active Pending
- 1995-08-15 ES ES95930466T patent/ES2143067T3/es not_active Expired - Lifetime
- 1995-08-15 BR BR9508592A patent/BR9508592A/pt not_active Application Discontinuation
- 1995-08-15 EP EP95930466A patent/EP0804407B1/de not_active Expired - Lifetime
- 1995-08-15 MX MX9701236A patent/MX9701236A/es unknown
- 1995-08-15 SK SK214-97A patent/SK21497A3/sk unknown
- 1995-08-15 AU AU33843/95A patent/AU3384395A/en not_active Abandoned
- 1995-08-15 CA CA002197666A patent/CA2197666A1/en not_active Abandoned
- 1995-08-15 WO PCT/EP1995/003246 patent/WO1996006066A1/en not_active Ceased
- 1995-08-15 KR KR1019970700980A patent/KR970704662A/ko not_active Withdrawn
- 1995-08-15 DE DE69514839T patent/DE69514839T2/de not_active Expired - Fee Related
- 1995-09-25 TW TW084109981A patent/TW360637B/zh active
1997
- 1997-11-26 US US08/979,264 patent/US5968322A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US5968322A (en)	1999-10-19
CA2197666A1 (en)	1996-02-29
AU3384395A (en)	1996-03-14
MX9701236A (es)	1997-05-31
KR970704662A (ko)	1997-09-06
JPH10504553A (ja)	1998-05-06
EP0804407A1 (de)	1997-11-05
TW360637B (en)	1999-06-11
DE69514839D1 (de)	2000-03-02
DE69514839T2 (de)	2000-06-15
ES2143067T3 (es)	2000-05-01
BR9508592A (pt)	1997-12-23
WO1996006066A1 (en)	1996-02-29
EP0804407B1 (de)	2000-01-26

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