FI106196B - Menetelmä metyylimetakrylaattimonomeerin valmistamiseksi asetosyaanihydriinistä - Google Patents

Menetelmä metyylimetakrylaattimonomeerin valmistamiseksi asetosyaanihydriinistä Download PDF

Info

Publication number: FI106196B
Authority: FI; Finland
Prior art keywords: process according; purification; amount; ammonia; methyl methacrylate
Prior art date: 1992-03-16

Application number

FI931108A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI931108L (fi

FI931108A0 (fi

Inventor

Alessandro Fabris

Dario Giudici

Original Assignee

Atochem Elf Italia

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.)

1992-03-16

Filing date

1993-03-12

Publication date

2000-12-15

1993-03-12 Application filed by Atochem Elf Italia filed Critical Atochem Elf Italia

1993-03-12 Publication of FI931108A0 publication Critical patent/FI931108A0/fi

1993-09-17 Publication of FI931108L publication Critical patent/FI931108L/fi

2000-12-15 Application granted granted Critical

2000-12-15 Publication of FI106196B publication Critical patent/FI106196B/fi

Links

VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 title claims abstract description 29
238000000034 method Methods 0.000 title claims abstract description 25
WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 title description 5
238000002360 preparation method Methods 0.000 title description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 41
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 39
229910021529 ammonia Inorganic materials 0.000 claims abstract description 19
239000003112 inhibitor Substances 0.000 claims abstract description 19
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 16
239000007800 oxidant agent Substances 0.000 claims abstract description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
230000032050 esterification Effects 0.000 claims abstract description 15
238000005886 esterification reaction Methods 0.000 claims abstract description 15
238000005406 washing Methods 0.000 claims abstract description 14
238000000746 purification Methods 0.000 claims abstract description 11
150000001412 amines Chemical class 0.000 claims abstract description 8
238000006243 chemical reaction Methods 0.000 claims abstract description 8
NTQWADDNQQUGRH-UHFFFAOYSA-N hydrogen sulfate;2-methylprop-2-enoylazanium Chemical compound OS(O)(=O)=O.CC(=C)C(N)=O NTQWADDNQQUGRH-UHFFFAOYSA-N 0.000 claims abstract description 8
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims abstract description 5
MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 claims abstract 2
230000017105 transposition Effects 0.000 claims abstract 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 13
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 12
239000000178 monomer Substances 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 10
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 8
230000001590 oxidative effect Effects 0.000 claims description 8
239000012074 organic phase Substances 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 7
239000012071 phase Substances 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 3
239000007864 aqueous solution Substances 0.000 claims description 3
229950000688 phenothiazine Drugs 0.000 claims description 3
239000011541 reaction mixture Substances 0.000 claims description 3
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 2
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
230000002829 reductive effect Effects 0.000 claims description 2
238000010790 dilution Methods 0.000 claims 1
239000012895 dilution Substances 0.000 claims 1
230000008030 elimination Effects 0.000 claims 1
238000003379 elimination reaction Methods 0.000 claims 1
150000003141 primary amines Chemical class 0.000 claims 1
150000003335 secondary amines Chemical class 0.000 claims 1
150000003512 tertiary amines Chemical class 0.000 claims 1
238000004821 distillation Methods 0.000 abstract description 5
235000011149 sulphuric acid Nutrition 0.000 abstract 1
239000001117 sulphuric acid Substances 0.000 abstract 1
238000000605 extraction Methods 0.000 description 10
238000006116 polymerization reaction Methods 0.000 description 9
239000000243 solution Substances 0.000 description 7
239000000047 product Substances 0.000 description 5
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
229910052921 ammonium sulfate Inorganic materials 0.000 description 3
239000001166 ammonium sulphate Substances 0.000 description 3
235000011130 ammonium sulphate Nutrition 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
230000008929 regeneration Effects 0.000 description 3
238000011069 regeneration method Methods 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000007865 diluting Methods 0.000 description 2
-1 hydrogen peroxide ions Chemical class 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000010410 layer Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-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
XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
150000003973 alkyl amines Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
238000004945 emulsification Methods 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000009413 insulation Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
229960000907 methylthioninium chloride Drugs 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
229940079877 pyrogallol Drugs 0.000 description 1
150000004053 quinones Chemical class 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000004065 semiconductor Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
239000002699 waste 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
- C07C67/18—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group
- C07C67/22—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group from nitriles
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

FI931108A 1992-03-16 1993-03-12 Menetelmä metyylimetakrylaattimonomeerin valmistamiseksi asetosyaanihydriinistä FI106196B (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ITMI920602A IT1257282B (it)	1992-03-16	1992-03-16	Processo migliorato per la produzione di metilmetacrilato monomero da acetoncianidrina
ITMI920602		1992-03-16

Publications (3)

Publication Number	Publication Date
FI931108A0 FI931108A0 (fi)	1993-03-12
FI931108L FI931108L (fi)	1993-09-17
FI106196B true FI106196B (fi)	2000-12-15

Family

ID=11362440

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI931108A FI106196B (fi)	1992-03-16	1993-03-12	Menetelmä metyylimetakrylaattimonomeerin valmistamiseksi asetosyaanihydriinistä

Country Status (7)

Country	Link
EP (1)	EP0561264B1 (fr)
AT (1)	ATE141253T1 (fr)
DE (1)	DE69303950T2 (fr)
ES (1)	ES2093298T3 (fr)
FI (1)	FI106196B (fr)
IT (1)	IT1257282B (fr)
NO (1)	NO179511C (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19803658A1 (de) *	1998-01-30	1999-08-05	Basf Ag	Verwendung von anionischen Flockungsmitteln bei der organisch-wässrigen Phasentrennung
DE102006058250A1 (de) *	2006-12-08	2008-06-12	Evonik Röhm Gmbh	Integriertes Verfahren und Vorrichtung zur Herstellung von Methacrylsäureestern aus Aceton und Blausäure
DE102006058251A1 (de) *	2006-12-08	2008-06-12	Evonik Röhm Gmbh	Verfahren und Vorrichtung zur Herstellung von Methacrylsäurealkylestern
JP5432852B2 (ja) *	2009-09-30	2014-03-05	ロームアンドハースカンパニー	メタクリル酸メチルの精製によって生じる流れから価値のある化合物を回収する方法
EP2635549B1 (fr) *	2010-11-04	2017-03-15	Rohm and Haas Company	Procédé de production de méthacrylate de méthyle ayant une teneur en biacétyle réduite
EP3212604B1 (fr)	2014-10-27	2020-11-25	Rohm and Haas Company	Procédé pour la production de méthacrylate de méthyle avec réduction d'encrassement
EP3212603B1 (fr) *	2014-10-27	2020-11-25	Rohm and Haas Company	Procédé à encrassement réduit pour la production de méthacrylate de méthyle
GB201704729D0 (en)	2017-03-24	2017-05-10	Lucite Int Uk Ltd	Method of producing methyl methacrylate or methacrylic acid

1992
- 1992-03-16 IT ITMI920602A patent/IT1257282B/it active IP Right Grant
1993
- 1993-03-10 AT AT93103810T patent/ATE141253T1/de not_active IP Right Cessation
- 1993-03-10 ES ES93103810T patent/ES2093298T3/es not_active Expired - Lifetime
- 1993-03-10 EP EP93103810A patent/EP0561264B1/fr not_active Expired - Lifetime
- 1993-03-10 DE DE69303950T patent/DE69303950T2/de not_active Expired - Lifetime
- 1993-03-11 NO NO930900A patent/NO179511C/no not_active IP Right Cessation
- 1993-03-12 FI FI931108A patent/FI106196B/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
FI931108L (fi)	1993-09-17
NO179511C (no)	1996-10-23
NO179511B (no)	1996-07-15
ES2093298T3 (es)	1996-12-16
EP0561264A3 (en)	1993-10-20
DE69303950D1 (de)	1996-09-19
NO930900D0 (no)	1993-03-11
IT1257282B (it)	1996-01-12
ATE141253T1 (de)	1996-08-15
FI931108A0 (fi)	1993-03-12
ITMI920602A1 (it)	1993-09-16
NO930900L (no)	1993-09-17
DE69303950T2 (de)	1997-02-27
EP0561264B1 (fr)	1996-08-14
ITMI920602A0 (it)	1992-03-16
EP0561264A2 (fr)	1993-09-22

Legal Events

Date	Code	Title	Description
2013-04-10	MA	Patent expired

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