CA1307761C - Production of dialkyl maleate from a mixture comprising a mondalkyl maleate - Google Patents
Production of dialkyl maleate from a mixture comprising a mondalkyl maleateInfo
- Publication number
- CA1307761C CA1307761C CA000543541A CA543541A CA1307761C CA 1307761 C CA1307761 C CA 1307761C CA 000543541 A CA000543541 A CA 000543541A CA 543541 A CA543541 A CA 543541A CA 1307761 C CA1307761 C CA 1307761C
- Authority
- CA
- Canada
- Prior art keywords
- maleate
- fraction
- distillation column
- maleic anhydride
- stream
- 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.)
- Expired - Lifetime
Links
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 title claims abstract description 103
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 title claims abstract description 90
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 19
- 239000000203 mixture Substances 0.000 title description 21
- 238000004821 distillation Methods 0.000 claims abstract description 148
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 claims abstract description 63
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 claims abstract description 63
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 63
- 238000000034 method Methods 0.000 claims abstract description 60
- 239000002253 acid Substances 0.000 claims abstract description 25
- 238000010924 continuous production Methods 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 95
- 238000010992 reflux Methods 0.000 claims description 44
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 claims description 34
- XLYMOEINVGRTEX-ARJAWSKDSA-N Ethyl hydrogen fumarate Chemical group CCOC(=O)\C=C/C(O)=O XLYMOEINVGRTEX-ARJAWSKDSA-N 0.000 claims description 32
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 17
- 238000009833 condensation Methods 0.000 claims description 16
- 230000005494 condensation Effects 0.000 claims description 16
- 238000006386 neutralization reaction Methods 0.000 claims description 13
- 238000011084 recovery Methods 0.000 claims description 8
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 7
- 238000005886 esterification reaction Methods 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 230000032050 esterification Effects 0.000 description 32
- 239000000047 product Substances 0.000 description 26
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 18
- 239000007788 liquid Substances 0.000 description 17
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 14
- 239000011976 maleic acid Substances 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 11
- 238000009835 boiling Methods 0.000 description 9
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000002688 maleic acid derivatives Chemical class 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 6
- 239000001530 fumaric acid Substances 0.000 description 5
- 239000002699 waste material Substances 0.000 description 5
- 238000010586 diagram Methods 0.000 description 4
- -1 maleic acid diester Chemical class 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical compound CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000498 cooling water Substances 0.000 description 2
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229940074369 monoethyl fumarate Drugs 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- 241000518994 Conta Species 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
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- UEKQGZQLUMSLNW-UHFFFAOYSA-N Propyl isome Chemical compound C1=C2C(C(=O)OCCC)C(C(=O)OCCC)C(C)CC2=CC2=C1OCO2 UEKQGZQLUMSLNW-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- RSRICHZMFPHXLE-WAYWQWQTSA-N bis(2-methylpropyl) (z)-but-2-enedioate Chemical compound CC(C)COC(=O)\C=C/C(=O)OCC(C)C RSRICHZMFPHXLE-WAYWQWQTSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- MWJNGKOBSUBRNM-FPLPWBNLSA-N dibutan-2-yl (z)-but-2-enedioate Chemical compound CCC(C)OC(=O)\C=C/C(=O)OC(C)CC MWJNGKOBSUBRNM-FPLPWBNLSA-N 0.000 description 1
- FNMTVMWFISHPEV-WAYWQWQTSA-N dipropan-2-yl (z)-but-2-enedioate Chemical compound CC(C)OC(=O)\C=C/C(=O)OC(C)C FNMTVMWFISHPEV-WAYWQWQTSA-N 0.000 description 1
- MSJMDZAOKORVFC-UAIGNFCESA-L disodium maleate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C/C([O-])=O MSJMDZAOKORVFC-UAIGNFCESA-L 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000011144 upstream manufacturing Methods 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
- C07C69/593—Dicarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/60—Maleic acid esters; Fumaric acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- 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
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- 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
- Y10S203/20—Power plant
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Glass Compositions (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868618892A GB8618892D0 (en) | 1986-08-01 | 1986-08-01 | Process |
| GB8618892 | 1986-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1307761C true CA1307761C (en) | 1992-09-22 |
Family
ID=10602124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000543541A Expired - Lifetime CA1307761C (en) | 1986-08-01 | 1987-07-31 | Production of dialkyl maleate from a mixture comprising a mondalkyl maleate |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4765869A (forum.php) |
| EP (1) | EP0255401B1 (forum.php) |
| JP (1) | JPH0813783B2 (forum.php) |
| KR (1) | KR950013080B1 (forum.php) |
| CN (1) | CN1014235B (forum.php) |
| AT (1) | ATE81844T1 (forum.php) |
| AU (1) | AU600290B2 (forum.php) |
| CA (1) | CA1307761C (forum.php) |
| DE (1) | DE3782370T2 (forum.php) |
| ES (1) | ES2035864T3 (forum.php) |
| GB (1) | GB8618892D0 (forum.php) |
| GR (2) | GR3001824T3 (forum.php) |
| IN (1) | IN170061B (forum.php) |
| MX (1) | MX168899B (forum.php) |
| NZ (1) | NZ221287A (forum.php) |
| RU (1) | RU2007383C1 (forum.php) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4740272A (en) * | 1987-03-31 | 1988-04-26 | Davy Mckee (London) Limited | Separation of monoalkyl maleate from dialkyl maleate |
| GB8717993D0 (en) * | 1987-07-29 | 1987-09-03 | Davy Mckee Ltd | Process |
| DE4423355A1 (de) | 1994-07-04 | 1996-01-11 | Bayer Ag | Verfahren zur Herstellung von Maleinsäuredialkylestern |
| BRPI0900867A2 (pt) * | 2009-04-16 | 2010-12-28 | Inst Presbiteriano Mackenzie | processo de obtenção de membranas hidrofìlicas a partir de poli (n-vinil-2-pirrolidona) pvp |
| CN114933531A (zh) * | 2022-06-07 | 2022-08-23 | 中建安装集团有限公司 | 一种悬浮催化精馏制备顺丁烯二酸二甲酯的方法及装置 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2333666A (en) * | 1940-09-14 | 1943-11-09 | American Cyanamid Co | Dialkyl esters of unsaturated dicarboxylic acids as insecticides |
| US2938837A (en) * | 1957-07-11 | 1960-05-31 | Standard Oil Co | Process for the purification of an aromatic dicarboxylic acid lower alkyl ester |
| FR1575909A (forum.php) * | 1968-06-12 | 1969-07-25 | ||
| US3979443A (en) * | 1972-08-25 | 1976-09-07 | Petro-Tex Chemical Corporation | Process for the preparation of esters of maleic acid with monohydric alcohols |
| US4032458A (en) * | 1975-08-08 | 1977-06-28 | Petro-Tex Chemical Corporation | Production of 1,4-butanediol |
| JPS6033098B2 (ja) * | 1977-07-26 | 1985-08-01 | 株式会社日本触媒 | 高純度マレイン酸モノアルコ−ル類エステルの製造法 |
| DE3106819A1 (de) * | 1981-02-24 | 1982-09-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 1,4-butandiol |
| GB8331793D0 (en) * | 1983-11-29 | 1984-01-04 | Davy Mckee Ltd | Process |
| DE3346134A1 (de) * | 1983-12-21 | 1985-07-04 | Basf Ag, 6700 Ludwigshafen | Verfahren zur kontinuierlichen abscheidung von maleinsaeureanhydrid aus gasfoermigen reaktionsgemischen |
| EP0204730A1 (en) * | 1984-11-21 | 1986-12-17 | DAVY McKEE (LONDON) LIMITED | Process for the production of butane-1,4-diol |
| SU1245568A1 (ru) * | 1985-02-11 | 1986-07-23 | Всесоюзный Научно-Исследовательский И Проектный Институт Мономеров | Способ получени ди- @ - @ -алкиловых эфиров малеиновой кислоты |
| GB8514001D0 (en) * | 1985-06-04 | 1985-07-10 | Davy Mckee Ltd | Process |
-
1986
- 1986-08-01 GB GB868618892A patent/GB8618892D0/en active Pending
-
1987
- 1987-07-31 AU AU76387/87A patent/AU600290B2/en not_active Ceased
- 1987-07-31 DE DE8787306807T patent/DE3782370T2/de not_active Expired - Lifetime
- 1987-07-31 CA CA000543541A patent/CA1307761C/en not_active Expired - Lifetime
- 1987-07-31 CN CN87105385A patent/CN1014235B/zh not_active Expired
- 1987-07-31 KR KR1019870008397A patent/KR950013080B1/ko not_active Expired - Lifetime
- 1987-07-31 ES ES198787306807T patent/ES2035864T3/es not_active Expired - Lifetime
- 1987-07-31 EP EP87306807A patent/EP0255401B1/en not_active Expired - Lifetime
- 1987-07-31 MX MX007548A patent/MX168899B/es unknown
- 1987-07-31 US US07/080,058 patent/US4765869A/en not_active Expired - Lifetime
- 1987-07-31 RU SU874203045A patent/RU2007383C1/ru active
- 1987-07-31 AT AT87306807T patent/ATE81844T1/de not_active IP Right Cessation
- 1987-07-31 NZ NZ221287A patent/NZ221287A/xx unknown
- 1987-08-01 JP JP62193633A patent/JPH0813783B2/ja not_active Expired - Lifetime
- 1987-08-31 IN IN553/MAS/87A patent/IN170061B/en unknown
-
1991
- 1991-04-23 GR GR91400232T patent/GR3001824T3/el unknown
-
1992
- 1992-12-24 GR GR920403145T patent/GR3006682T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1014235B (zh) | 1991-10-09 |
| CN87105385A (zh) | 1988-04-27 |
| NZ221287A (en) | 1989-07-27 |
| GR3001824T3 (en) | 1992-11-23 |
| KR880002798A (ko) | 1988-05-11 |
| RU2007383C1 (ru) | 1994-02-15 |
| ATE81844T1 (de) | 1992-11-15 |
| DE3782370T2 (de) | 1993-03-11 |
| GB8618892D0 (en) | 1986-09-10 |
| EP0255401A2 (en) | 1988-02-03 |
| AU600290B2 (en) | 1990-08-09 |
| IN170061B (forum.php) | 1992-02-01 |
| US4765869A (en) | 1988-08-23 |
| GR3006682T3 (forum.php) | 1993-06-30 |
| EP0255401A3 (en) | 1989-08-02 |
| JPS6388158A (ja) | 1988-04-19 |
| EP0255401B1 (en) | 1992-10-28 |
| MX168899B (es) | 1993-06-14 |
| JPH0813783B2 (ja) | 1996-02-14 |
| KR950013080B1 (ko) | 1995-10-24 |
| ES2035864T3 (es) | 1993-05-01 |
| DE3782370D1 (de) | 1992-12-03 |
| AU7638787A (en) | 1988-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |