DE2802922C2 - Verfahren zur Herstellung von Aldehyden durch Hydroformylierung von α-Olefinen - Google Patents
Verfahren zur Herstellung von Aldehyden durch Hydroformylierung von α-OlefinenInfo
- Publication number
- DE2802922C2 DE2802922C2 DE2802922A DE2802922A DE2802922C2 DE 2802922 C2 DE2802922 C2 DE 2802922C2 DE 2802922 A DE2802922 A DE 2802922A DE 2802922 A DE2802922 A DE 2802922A DE 2802922 C2 DE2802922 C2 DE 2802922C2
- Authority
- DE
- Germany
- Prior art keywords
- rhodium
- carbon monoxide
- catalyst
- reaction
- hydroformylation
- 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
Links
- 238000000034 method Methods 0.000 title claims description 30
- 238000007037 hydroformylation reaction Methods 0.000 title claims description 27
- 150000001299 aldehydes Chemical class 0.000 title claims description 24
- 239000004711 α-olefin Substances 0.000 title claims description 11
- 239000010948 rhodium Substances 0.000 claims description 57
- 239000003054 catalyst Substances 0.000 claims description 49
- 229910052703 rhodium Inorganic materials 0.000 claims description 45
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 44
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 32
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 32
- 239000003446 ligand Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 239000012429 reaction media Substances 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 239000007789 gas Substances 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 230000009918 complex formation Effects 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 39
- TUJWIYZCAPMHSA-UHFFFAOYSA-N dipentylphosphoryloxybenzene Chemical compound CCCCCP(=O)(CCCCC)OC1=CC=CC=C1 TUJWIYZCAPMHSA-UHFFFAOYSA-N 0.000 description 27
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 22
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical class CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 19
- 230000000694 effects Effects 0.000 description 16
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 14
- 150000001336 alkenes Chemical class 0.000 description 13
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000007859 condensation product Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 11
- AJRJPORIQGYFMT-RMOCHZDMSA-N 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine Chemical compound C\C=C1\N(C)C(C)CC1(C=1C=CC=CC=1)C1=CC=CC=C1 AJRJPORIQGYFMT-RMOCHZDMSA-N 0.000 description 10
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- AAXGWYDSLJUQLN-UHFFFAOYSA-N diphenyl(propyl)phosphane Chemical compound C=1C=CC=CC=1P(CCC)C1=CC=CC=C1 AAXGWYDSLJUQLN-UHFFFAOYSA-N 0.000 description 9
- 231100000614 poison Toxicity 0.000 description 9
- 239000002574 poison Substances 0.000 description 9
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
- -1 BH 2 S Chemical class 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000009849 deactivation Effects 0.000 description 4
- WUOIAOOSKMHJOV-UHFFFAOYSA-N ethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CC)C1=CC=CC=C1 WUOIAOOSKMHJOV-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000011027 product recovery Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000036632 reaction speed Effects 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- FQSDTIQFGVAWNS-UHFFFAOYSA-N rhodium;(triphenyl-$l^{5}-phosphanylidene)methanone Chemical compound [Rh].C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C=O)C1=CC=CC=C1 FQSDTIQFGVAWNS-UHFFFAOYSA-N 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 231100000765 toxin Toxicity 0.000 description 2
- 239000003053 toxin Substances 0.000 description 2
- 108700012359 toxins Proteins 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical class C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- VVIGJTLLPPTWRI-UHFFFAOYSA-N bis(4-methoxyphenyl)-propylphosphane Chemical compound C=1C=C(OC)C=CC=1P(CCC)C1=CC=C(OC)C=C1 VVIGJTLLPPTWRI-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WXMZPPIDLJRXNK-UHFFFAOYSA-N butyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCCC)C1=CC=CC=C1 WXMZPPIDLJRXNK-UHFFFAOYSA-N 0.000 description 1
- VYQRNVGDIRYDME-UHFFFAOYSA-N butyl-bis(2-methylphenyl)phosphane Chemical compound C=1C=CC=C(C)C=1P(CCCC)C1=CC=CC=C1C VYQRNVGDIRYDME-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- STJREGJFVITWMO-UHFFFAOYSA-N dinaphthalen-1-yl(propyl)phosphane Chemical compound C1=CC=C2C(P(C=3C4=CC=CC=C4C=CC=3)CCC)=CC=CC2=C1 STJREGJFVITWMO-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- ZZJQJNACQREUFM-UHFFFAOYSA-N methyl(dinaphthalen-1-yl)phosphane Chemical compound C1=CC=C2C(P(C=3C4=CC=CC=C4C=CC=3)C)=CC=CC2=C1 ZZJQJNACQREUFM-UHFFFAOYSA-N 0.000 description 1
- UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DMEUUKUNSVFYAA-UHFFFAOYSA-N trinaphthalen-1-ylphosphane Chemical compound C1=CC=C2C(P(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 DMEUUKUNSVFYAA-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- UYUUAUOYLFIRJG-UHFFFAOYSA-N tris(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1P(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 UYUUAUOYLFIRJG-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76233577A | 1977-01-25 | 1977-01-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2802922A1 DE2802922A1 (de) | 1978-07-27 |
| DE2802922C2 true DE2802922C2 (de) | 1984-03-01 |
Family
ID=25064756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2802922A Expired DE2802922C2 (de) | 1977-01-25 | 1978-01-24 | Verfahren zur Herstellung von Aldehyden durch Hydroformylierung von α-Olefinen |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5392707A (en, 2012) |
| AR (1) | AR230744A1 (en, 2012) |
| AT (1) | AT364346B (en, 2012) |
| AU (1) | AU519322B2 (en, 2012) |
| BE (1) | BE863267R (en, 2012) |
| BR (1) | BR7800397A (en, 2012) |
| CA (1) | CA1106407A (en, 2012) |
| DE (1) | DE2802922C2 (en, 2012) |
| ES (1) | ES466267A1 (en, 2012) |
| FR (1) | FR2377991A2 (en, 2012) |
| GB (1) | GB1599921A (en, 2012) |
| IN (2) | IN147429B (en, 2012) |
| IT (1) | IT1158444B (en, 2012) |
| MX (1) | MX147988A (en, 2012) |
| NL (1) | NL186237C (en, 2012) |
| SE (1) | SE444932B (en, 2012) |
| ZA (1) | ZA78146B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2459683A1 (fr) | 1979-06-22 | 1981-01-16 | Ugine Kuhlmann | Procede de stabilisation et de regeneration du catalyseur d'hydroformylation du propene |
| US4283562A (en) * | 1979-10-26 | 1981-08-11 | Union Carbide Corporation | Hydroformylation process using stable rhodium catalyst |
| US4687874A (en) * | 1980-02-12 | 1987-08-18 | Exxon Research And Engineering Company | Selective hydroformylation process using alkyl diaryl phosphine rhodium carbonyl hydride catalysts |
| DE3639172A1 (de) * | 1986-11-15 | 1988-05-26 | Webasto Ag Fahrzeugtechnik | Verfahren zum betreiben eines brennstoffbetriebenen heizgeraets und anordnung zur durchfuehrung des verfahrens |
| US4731486A (en) * | 1986-11-18 | 1988-03-15 | Union Carbide Corporation | Hydroformylation using low volatile phosphine ligands |
| KR950000635B1 (ko) * | 1988-07-14 | 1995-01-26 | 유니온 카바이드 케미칼즈 앤드 플라스틱스 캄파니 인코포레이티드 | 비수성 하이드로포르밀화 반응 생성물 조성물로부터 알데히드 생성물을 분리회수하는 방법 |
| JP4523411B2 (ja) | 2002-08-31 | 2010-08-11 | エボニック オクセノ ゲゼルシャフト ミット ベシュレンクテル ハフツング | 環状炭酸エステルの存在下でのオレフィン性不飽和化合物、特にオレフィンのヒドロホルミル化法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3855307A (en) * | 1967-02-20 | 1974-12-17 | Monsanto Co | Catalysis |
| US3527809A (en) * | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
| US3572809A (en) * | 1968-11-26 | 1971-03-30 | Arlo T Buland | Expansible mobile home and fittings therefore |
| CA918673A (en) * | 1969-12-22 | 1973-01-09 | L. Pruett Roy | Hydroformylation process |
| GB1338225A (en) * | 1969-12-31 | 1973-11-21 | Johnson Matthey Co Ltd | Catalytic reactions |
| JPS50123611A (en, 2012) * | 1974-03-12 | 1975-09-29 | ||
| JPS511687A (en) * | 1974-06-27 | 1976-01-08 | Sadao Ukita | Tenpura hanbaagunadono nenseizairyono katakeiseinisaishiteno atsumichoseisochi |
| JPS516124A (en) * | 1974-07-05 | 1976-01-19 | Hitachi Chemical Co Ltd | Kikinzoku oyobi ryusandono kaishuhoho |
| IN146241B (en, 2012) * | 1976-04-08 | 1979-03-31 | Union Carbide Corp |
-
1978
- 1978-01-10 ZA ZA00780146A patent/ZA78146B/xx unknown
- 1978-01-19 CA CA295,303A patent/CA1106407A/en not_active Expired
- 1978-01-23 AU AU32628/78A patent/AU519322B2/en not_active Expired
- 1978-01-24 JP JP589378A patent/JPS5392707A/ja active Granted
- 1978-01-24 GB GB2906/78A patent/GB1599921A/en not_active Expired
- 1978-01-24 DE DE2802922A patent/DE2802922C2/de not_active Expired
- 1978-01-24 BE BE184599A patent/BE863267R/xx not_active IP Right Cessation
- 1978-01-24 ES ES466267A patent/ES466267A1/es not_active Expired
- 1978-01-24 FR FR7801866A patent/FR2377991A2/fr active Granted
- 1978-01-24 IN IN95/CAL/78A patent/IN147429B/en unknown
- 1978-01-24 IN IN94/CAL/78A patent/IN146408B/en unknown
- 1978-01-24 BR BR7800397A patent/BR7800397A/pt unknown
- 1978-01-24 SE SE7800871A patent/SE444932B/sv not_active IP Right Cessation
- 1978-01-24 MX MX172154A patent/MX147988A/es unknown
- 1978-01-24 AT AT0049278A patent/AT364346B/de not_active IP Right Cessation
- 1978-01-24 NL NLAANVRAGE7800855,A patent/NL186237C/xx not_active IP Right Cessation
- 1978-01-24 AR AR270818A patent/AR230744A1/es active
- 1978-01-24 IT IT7819577A patent/IT1158444B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1599921A (en) | 1981-10-07 |
| JPS5761336B2 (en, 2012) | 1982-12-23 |
| CA1106407A (en) | 1981-08-04 |
| ES466267A1 (es) | 1978-10-01 |
| NL7800855A (nl) | 1978-07-27 |
| SE444932B (sv) | 1986-05-20 |
| JPS5392707A (en) | 1978-08-15 |
| IT1158444B (it) | 1987-02-18 |
| SE7800871L (sv) | 1978-09-18 |
| FR2377991A2 (fr) | 1978-08-18 |
| AU3262878A (en) | 1979-08-02 |
| AU519322B2 (en) | 1981-11-26 |
| IN147429B (en, 2012) | 1980-02-23 |
| IN146408B (en, 2012) | 1979-05-26 |
| AR230744A1 (es) | 1984-06-29 |
| FR2377991B2 (en, 2012) | 1984-02-03 |
| BR7800397A (pt) | 1978-08-22 |
| MX147988A (es) | 1983-02-22 |
| BE863267R (fr) | 1978-07-24 |
| NL186237C (nl) | 1990-10-16 |
| NL186237B (nl) | 1990-05-16 |
| AT364346B (de) | 1981-10-12 |
| ATA49278A (de) | 1981-03-15 |
| ZA78146B (en) | 1978-12-27 |
| DE2802922A1 (de) | 1978-07-27 |
| IT7819577A0 (it) | 1978-01-24 |
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