CH617660A5 - - Google Patents
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- Publication number
- CH617660A5 CH617660A5 CH1520775A CH1520775A CH617660A5 CH 617660 A5 CH617660 A5 CH 617660A5 CH 1520775 A CH1520775 A CH 1520775A CH 1520775 A CH1520775 A CH 1520775A CH 617660 A5 CH617660 A5 CH 617660A5
- Authority
- CH
- Switzerland
- Prior art keywords
- carbonate
- carbonates
- lewis acids
- aryloxy
- phenyl ethyl
- Prior art date
Links
- -1 aromatic carbonates Chemical class 0.000 claims 7
- 238000006243 chemical reaction Methods 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 239000002841 Lewis acid Substances 0.000 claims 6
- 150000007517 lewis acids Chemical class 0.000 claims 6
- 239000010936 titanium Substances 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims 4
- YCNSGSUGQPDYTK-UHFFFAOYSA-N ethyl phenyl carbonate Chemical compound CCOC(=O)OC1=CC=CC=C1 YCNSGSUGQPDYTK-UHFFFAOYSA-N 0.000 claims 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 229910052719 titanium Inorganic materials 0.000 claims 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 claims 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 150000003623 transition metal compounds Chemical class 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims 1
- LYQCTTBHFKYWQY-UHFFFAOYSA-N dimethyl carbonate;hexane Chemical compound CCCCCC.COC(=O)OC LYQCTTBHFKYWQY-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 229920000515 polycarbonate Polymers 0.000 claims 1
- 239000004417 polycarbonate Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Description
6176«)
Claims (4)
- RIVENDICAZIONI 1. Processo per la preparazione di carbonati aromatici di formula generale- 0(1-5)(1-5)nella quale R è un sostituente scelto tra i gruppi alchili, al-cossi, arili, arilossi o N02 caratterizzato dall'operazione di metter in contatto un composto di formula generale'(1-5)dove R ha i significati di cui sopra ed Rl è un gruppo alchi-lico non terziario, con un sistema catalitico scelto fra gli acidi di Lewis ed i composti dei metalli di transizione dai quali gli acidi di Lewis possono essere generati.
- 2. Processo secondo la rivendicazione 1, caratterizzato dal fatto che il catalizzatore viene particolarmente scelto tra A1X3) TìX3, VX,, TiX4, VOX,, VX5, ZnX2, SnX4 ove X è alogeno, acetossi, alcossi o arilossi.
- 3. Processo secondo le rivendicazioni 1 e 2-, caratterizzato dal fatto che la reazione viene effettuata in presenza di un catalizzatore costituito da un addotto dei composti sopra definiti con molecole organiche.
- 4. Processo secondo le rivendicazioni 1, 2 e 3, caratterizzato dal fatto che la reazione è effettuata a temperature comprese fra 25 e 360°C e pressioni fra 0,1 e 100 ata.La presente invenzione concerne un processo per la preparazione di carbonati aromatici di formula generaleOCO - 0(1-5)nella quale R è un sostituente scelto fra i gruppi alchile, alcossi, arile, arilossi o N02, detto processo essendo caratterizzato dall'operazione di mettere in contatto10-C0 ORdove R1 è un gruppo alchilico non terziario, con un sistema catalitico scelto fra gli acidi di Lewis ed i composti dei metalli di transizione da cui gli acidi di Lewis possono essere generati.5 E' noto che i diaril-carbonati vengono preparati a partire dai rispettivi fenoli con fosgene mediante una tecnologia complessa che comporta notevoli rischi e che implica la formazione come coprodotto di acido cloridrico. I carbonati aromatici hanno un notevole interesse industriale perchè vento gono impiegati quali intermedi nella produzione di policarbo-nati aromatici e nella sintesi di alcuni isocianati. E' stato ora trovato e ciò costituisce oggetto della presente invenzione, che è possibile ottenere con elevate rese e selettività diaril-carbonati facendo reagire fenil alchil carbonati in presenza di op-15 portuni catalizzatori. Dalla reazione si ottengono accanto ai diaril carbonati in quantità equimolecolare i dialchilcarbonati.Secondo una preferita forma di esecuzione del processo, la reazione viene condotta in fase liquida con o senza solventi a temperature comprese fra 25 e 350°C e preferibilmente 20 fra 80 e 250°C a pressioni fra 0,1 e 100 ata e preferibilmente fra 1 e 25 Ata. Sono efficienti catalizzatori di formula A1X3, Ti X3, UX4, Ti X4, VO X3, VX5, Zn X2, Fe X3, Sn X4 ove X è alogeno, acetossi, alcossi, arilossi e in genere acidi di Lewis, o i composti di metalli di transizione che li generano. 25 Gli acidi di Lewis possono essere impiegati da soli, od in miscela tra loro, oppure si possono impiegare addotti degli stessi con molecole organiche.Vengono riportati qui di seguito alcuni pratici esempi di esecuzione.30Esempio 1Si sono fatti reagire a 180°C per quattro ore una mole di fenil-etil carbonato e 0,023 moli di tetrafenato di titanio. 35 Si è ottenuta una conversione del fenil etil carbonato del 40% con selettività a difenil carbonato e dietil carbonato superiori a 95% essendosi formate anche piccole quantità di fenil etil etere.40455055R(1-JEsempio 2Si sono fatti reagire a 180°C per 4 ore 60 g di fenilmetil carbonato e 1,5 gr di titanio tetrametilato in presenza di 50 cc di normal esano distillando in continuo l'azeotropo di-metil carbonato-esano a rapporto di riflusso 20/1.Si è avuta una conversione del fenil metilcarbonato del 63% con selettività superiore al 95% a DFC (difenil carbonato) e dimetil carbonato, essendo presenti piccole quantità di anisolo.Esempio 3Si sono fatti reagire per quattro ore a 180°C, 60 gr di fenil etil carbonato, 3,5 gr di titanio tetrafenato e 60 cc di etil cicloesano distillando in continuo l'azeotropo dietil carbonato-idrocarburo a rapporto di riflusso 20/1.Si è avuta una conversione del fenil-etilcarbonato del 70% con selettività superiore al 95 % a DFC e dietil carbonato con piccole quantità di fenil etil etere.v
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT7429773A IT1025961B (it) | 1974-11-25 | 1974-11-25 | Processo per la preparazione di carbonati aromatici |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH617660A5 true CH617660A5 (it) | 1980-06-13 |
Family
ID=11228414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1520775A CH617660A5 (it) | 1974-11-25 | 1975-11-24 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4045464A (it) |
| JP (1) | JPS5848537B2 (it) |
| AT (1) | AT347428B (it) |
| BE (1) | BE835820A (it) |
| CA (1) | CA1058203A (it) |
| CH (1) | CH617660A5 (it) |
| DD (1) | DD122373A5 (it) |
| DE (1) | DE2552907C3 (it) |
| DK (1) | DK154135C (it) |
| FR (1) | FR2291967A1 (it) |
| GB (1) | GB1481920A (it) |
| HU (1) | HU171210B (it) |
| IL (1) | IL48542A (it) |
| IT (1) | IT1025961B (it) |
| LU (1) | LU73853A1 (it) |
| NO (1) | NO143900C (it) |
| SE (1) | SE426391B (it) |
| YU (1) | YU36006B (it) |
| ZA (1) | ZA757112B (it) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4182726A (en) * | 1974-06-25 | 1980-01-08 | Snamprogetti, S.P.A. | Process for the preparation of aromatic carbonates |
| JPS52156960A (en) * | 1976-06-24 | 1977-12-27 | Sanei Kagaku Kogyo Kk | Cooked frozen meat food |
| DE2736063A1 (de) * | 1977-08-10 | 1979-02-22 | Bayer Ag | Verfahren zur herstellung aromatischer kohlensaeureester |
| DE2736062A1 (de) * | 1977-08-10 | 1979-02-22 | Bayer Ag | Verfahren zur herstellung aromatischer kohlensaeureester |
| US4533504A (en) * | 1982-01-08 | 1985-08-06 | General Electric Company | Process for the preparation of diaryl carbonates |
| US4410464A (en) * | 1982-03-15 | 1983-10-18 | General Electric Company | Diaryl carbonate process |
| US4509537A (en) * | 1983-04-04 | 1985-04-09 | Philip Morris Incorporated | Smoking compositions |
| US4609501A (en) * | 1983-12-27 | 1986-09-02 | General Electric Company | Process for the preparation of aromatic carbonates |
| US5166393A (en) * | 1987-10-05 | 1992-11-24 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing diaryl carbonate |
| US5034557A (en) * | 1988-04-16 | 1991-07-23 | Mitsui Petrochemical Industries, Ltd. | Process for production of aromatic carbonate compound |
| JP2540590B2 (ja) * | 1988-04-16 | 1996-10-02 | 三井石油化学工業株式会社 | 芳香族カ―ボネ―ト化合物を製造する方法 |
| US5167946A (en) * | 1990-12-27 | 1992-12-01 | The Dow Chemical Company | Diaryl carbonate process |
| GB2255972A (en) * | 1991-04-12 | 1992-11-25 | Davy Res & Dev Ltd | Production of diaryl carbonates. |
| WO1992018459A1 (fr) * | 1991-04-18 | 1992-10-29 | Yoshitomi Pharmaceutical Industries, Ltd. | Compose d'ester benzoique et procede de production |
| US5252771A (en) * | 1991-05-28 | 1993-10-12 | The Dow Chemical Company | Aluminum trifluoride catalyst for production of diaryl carbonates |
| US5380909A (en) * | 1991-06-24 | 1995-01-10 | The Dow Chemical Company | Captive carbonyl halide process for production of diaryl carbonates |
| US5239105A (en) * | 1992-01-30 | 1993-08-24 | The Dow Chemical Company | Catalytic formation of diarylcarbonates |
| DE4207853A1 (de) * | 1992-03-12 | 1993-09-16 | Bayer Ag | Verfahren zur herstellung von aromatischen carbonaten |
| US5380908A (en) * | 1992-10-08 | 1995-01-10 | Daicel Chemical Industries, Ltd. | Continuous production of aromatic carbonates |
| DE4301899A1 (de) * | 1993-01-25 | 1994-07-28 | Bayer Ag | Verfahren zur kontinuierlichen Herstellung von Arylcarbonaten |
| TW310322B (it) * | 1994-05-25 | 1997-07-11 | Nippon Catalytic Chem Ind | |
| IT1282363B1 (it) * | 1996-01-16 | 1998-03-20 | Enichem Spa | Procedimento continuo per la preparazione di fenil metil carbonato |
| US5980445A (en) * | 1996-11-22 | 1999-11-09 | Mitsubishi Gas Chemical Company, Inc. | Process for producing diaryl carbonate |
| US5962720A (en) * | 1997-05-29 | 1999-10-05 | Wilson Greatbatch Ltd. | Method of synthesizing unsymmetric organic carbonates and preparing nonaqueous electrolytes for alkali ion electrochemical cells |
| US7417161B2 (en) * | 2002-02-05 | 2008-08-26 | Lg Chem. Ltd. | Continuous method for preparing aromatic carbonate using a heterogeneous catalyst and a reaction apparatus for the same |
| US7919644B2 (en) | 2004-06-17 | 2011-04-05 | Asahi Kasei Chemicals Corporation | Process for producing an aromatic carbonate |
| BRPI0512524A (pt) * | 2004-06-25 | 2008-03-11 | Asahi Kasei Chemicals Corp | processo para a produção de um carbonato aromático, processo para a produção industrial do mesmo, carbonato aromático, e, coluna de destilação contìnua de múltiplos estágios |
| EP1762560A4 (en) * | 2004-06-25 | 2008-05-07 | Asahi Kasei Chemicals Corp | PROCESS FOR PRODUCING AROMATIC CARBONATE AT THE INDUSTRIAL SCALE |
| US20070219387A1 (en) | 2004-07-13 | 2007-09-20 | Asahi Kasei Chemicals Corporation | Industrial Process for Producing an Aromatic Carbonate |
| EP1775280B1 (en) | 2004-07-13 | 2013-09-11 | Asahi Kasei Chemicals Corporation | Industrial process for producing aromatic carbonate |
| JP4224104B2 (ja) | 2004-07-14 | 2009-02-12 | 旭化成ケミカルズ株式会社 | 芳香族カーボネート類を工業的に製造する方法 |
| EP1767517A4 (en) | 2004-07-14 | 2008-08-20 | Asahi Kasei Chemicals Corp | INDUSTRIAL PROCESS FOR PREPARING AN AROMATIC CARBONATE |
| EA010066B1 (ru) | 2004-08-25 | 2008-06-30 | Асахи Касеи Кемикалз Корпорейшн | Способ производства высокочистого дифенилкарбоната в промышленном масштабе |
| US20070260083A1 (en) * | 2004-09-02 | 2007-11-08 | Shinsuke Fukuoka | Industrial Process for Production of High-Purity Diphenyl Carbonate |
| JP4292211B2 (ja) * | 2004-09-03 | 2009-07-08 | 旭化成ケミカルズ株式会社 | 高純度ジアリールカーボネートの工業的製造方法 |
| EP1795522A4 (en) * | 2004-09-27 | 2008-08-06 | Asahi Kasei Chemicals Corp | PROCESS FOR THE MANUFACTURE OF AROMATIC CARBONATE IN INDUSTRIAL STANDARD |
| WO2006041075A1 (ja) * | 2004-10-14 | 2006-04-20 | Asahi Kasei Chemicals Corporation | 高純度ジアリールカーボネートの製造方法 |
| TWI321561B (en) | 2004-12-21 | 2010-03-11 | Asahi Kasei Chemicals Corp | Method for producing aromatic carbonate |
| CA2595125C (en) | 2004-12-24 | 2011-11-08 | Asahi Kasei Chemicals Corporation | Process for production of aromatic carbonate |
| US7378540B2 (en) * | 2005-10-21 | 2008-05-27 | Catalytic Distillation Technologies | Process for producing organic carbonates |
| EP2178820A1 (en) * | 2007-08-20 | 2010-04-28 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of a diaryl carbonate |
| US8110698B2 (en) | 2008-02-11 | 2012-02-07 | Shell Oil Company | Process for producing diphenyl carbonate |
| US7851645B2 (en) * | 2008-02-11 | 2010-12-14 | Catalytic Distillation Technologies | Process for continuous production of organic carbonates or organic carbamates and solid catalysts therefore |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3517029A (en) * | 1964-08-17 | 1970-06-23 | Eastman Kodak Co | Cyclic polymethylene monothiolcarbonates and their preparation |
| DE1770329A1 (de) * | 1967-05-05 | 1970-08-20 | Inst Tworzyw Sztucznych | Verfahren zur Herstellung von Polycarbonaten |
| US3655626A (en) * | 1968-10-02 | 1972-04-11 | United States Steel Corp | Interpolycarbonates from 9 10 - bis (hydroxymethyl) - s - octahydroanthracene-bis (alkyl or aryl carbonates) |
-
1974
- 1974-11-25 IT IT7429773A patent/IT1025961B/it active
-
1975
- 1975-11-12 ZA ZA00757112A patent/ZA757112B/xx unknown
- 1975-11-18 GB GB47551/75A patent/GB1481920A/en not_active Expired
- 1975-11-21 BE BE162077A patent/BE835820A/xx not_active IP Right Cessation
- 1975-11-21 DK DK526875A patent/DK154135C/da not_active IP Right Cessation
- 1975-11-24 YU YU2980/75A patent/YU36006B/xx unknown
- 1975-11-24 CH CH1520775A patent/CH617660A5/it not_active IP Right Cessation
- 1975-11-24 NO NO75753959A patent/NO143900C/no unknown
- 1975-11-24 AT AT891775A patent/AT347428B/de not_active IP Right Cessation
- 1975-11-24 LU LU73853A patent/LU73853A1/xx unknown
- 1975-11-24 CA CA240,327A patent/CA1058203A/en not_active Expired
- 1975-11-24 FR FR7535832A patent/FR2291967A1/fr active Granted
- 1975-11-24 HU HU75AI00000248A patent/HU171210B/hu unknown
- 1975-11-25 JP JP50140312A patent/JPS5848537B2/ja not_active Expired
- 1975-11-25 IL IL7548542A patent/IL48542A/xx unknown
- 1975-11-25 DE DE2552907A patent/DE2552907C3/de not_active Expired
- 1975-11-25 SE SE7513239A patent/SE426391B/xx unknown
- 1975-11-25 DD DD189676A patent/DD122373A5/xx unknown
- 1975-12-01 US US05/636,604 patent/US4045464A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DK154135B (da) | 1988-10-17 |
| DE2552907C3 (de) | 1978-08-17 |
| DE2552907A1 (de) | 1976-05-26 |
| IT1025961B (it) | 1978-08-30 |
| ZA757112B (en) | 1976-10-27 |
| BE835820A (fr) | 1976-05-21 |
| NO143900B (no) | 1981-01-26 |
| ATA891775A (de) | 1978-05-15 |
| HU171210B (hu) | 1977-12-28 |
| SE426391B (sv) | 1983-01-17 |
| AU8679375A (en) | 1977-05-26 |
| DK526875A (da) | 1976-05-26 |
| US4045464A (en) | 1977-08-30 |
| GB1481920A (en) | 1977-08-03 |
| NO143900C (no) | 1981-05-06 |
| IL48542A0 (en) | 1976-01-30 |
| LU73853A1 (it) | 1976-06-11 |
| JPS5848537B2 (ja) | 1983-10-28 |
| YU298075A (en) | 1981-02-28 |
| FR2291967B1 (it) | 1979-02-02 |
| DE2552907B2 (de) | 1977-12-08 |
| NO753959L (it) | 1976-05-26 |
| FR2291967A1 (fr) | 1976-06-18 |
| DK154135C (da) | 1989-03-06 |
| AT347428B (de) | 1978-12-27 |
| JPS5175044A (it) | 1976-06-29 |
| SE7513239L (sv) | 1976-05-26 |
| YU36006B (en) | 1981-11-13 |
| DD122373A5 (it) | 1976-10-05 |
| CA1058203A (en) | 1979-07-10 |
| IL48542A (en) | 1978-08-31 |
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