PL85B1 - The method of obtaining perylene. - Google Patents
The method of obtaining perylene. Download PDFInfo
- Publication number
- PL85B1 PL85B1 PL85A PL8519A PL85B1 PL 85 B1 PL85 B1 PL 85B1 PL 85 A PL85 A PL 85A PL 8519 A PL8519 A PL 8519A PL 85 B1 PL85 B1 PL 85B1
- Authority
- PL
- Poland
- Prior art keywords
- perylene
- obtaining
- dinaphthyl
- naphthalene
- heated
- Prior art date
Links
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 title claims description 11
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000012320 chlorinating reagent Substances 0.000 claims description 2
- 230000001698 pyrogenic effect Effects 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Description
Dotychczasowe syntezy perylenu (Ber. 48s. 2202) z naftalin — a-dinaftylu albo pochodnych dawalynieznaczna wydajnosc.Okazalo sie obecnie, ze wydajnosc znacznie sie powieksza, jezeli [3-pochodne naftaliny albo a-dinaftylu traktuje sie srodkami chlorujacemi, jak zwiazki chloru z fosforem, antymonem, arsenem, glinem i t. p., przyczem powstaja [3-chloropo- chodne naftaliny, albo takiez zwiazki a-dinaftylu, które nastepnie w znany sposób naprz., chlorkiem glinu, albo na drodze pyrogenicznej moga byc przepro¬ wadzone w perylen. Poleca sie jedno¬ czesnie stosowanie srodków redukujacych jak kwas fosforawy. Reakcja moze sie odbywac w ten sposób, ze, wychodzac z substytuowanych p-pochodnych naftaliny albo a-dinaftylu przeprowadza sie izolacje substytuowanej (3 - halogenopochodnych tego weglowodoru albo nie przeprowadza sie. Mozna równiez wychodzic z (3-halo- geno a-dinaftylów, otrzymanych na do¬ wolnej drodze.PRZYKLADY: 1. 1 kg p-dinaftolu ogrzewa sie predko z 1 kg kwasu fosforawego przy jednoczesnem dodawaniu 1 kg trój¬ chlorku fosforu. Reakcj a odbywa sie przy silnem pienieniu sie i wydzie¬ laniu fosforowodoru, który sie sam przez sie zapala. Po ukonczeniu wydzielania tego gazu produkt pod¬ daje sie czastkowej destylacji i wten sposób oddziela od jednoczesnie powstajacych tlenków dinaftylu.Wydajnosc czystego technicznego perylenu wynosi 60% materjalu wyjsciowego. Przytern produkt mo-ze byc wykrystalizowany z benzolu albo lodowatego kwasu octowego i otrzymuje sie czysty perylen, w ilosci okolo 80% technicznego perylenu. 2. Jezeli sie wychodzi z [3-dichloro a-dinaftylu, to reakcje mozna prze¬ prowadzic albo bez powyzej wspom¬ nianych srodków plynnych albo przy ich pomocy. Jezeli sie reakcje prowadzi pyrogenicznie bez srod¬ ków plynnych, to wydajnosc jest gorsza. a) 1 kg (3-dicbloro a-dinaftylu ogrze¬ wa sie do 500 — 600° i produkt reakcji obrabia, jak w przykladzie 1.Wydajnosc technicznie czystego perylenu wynosi 20% materjalu wyjsciowego. b) 1 kg (3-dichloro a-dinaftylu ogrzewa sie przy dodaniu 1 kg kwasu fos¬ forawego do 500° i produkt reak¬ cji obrabia sie, jak w przykladzie 1; otrzymuje sie wtedy czysty tech¬ nicznie perylen w ilosci 75% ma¬ terjalu wyjsciowego. 3. Jezeli sie postepuje jak w przy¬ kladzie 1, ale mieszanine w tych samych stosunkach ogrzewa sie do nizszej temperatury, niz podane w przykladzie 1, i produkt wystyga bez poprzedniej destylacji, to po wygotowaniu ochlodzonego pro¬ duktu z lugiem sodowym, albo potasowym, mozna oddzielic ciemno zabarwiona substancje, która nie krystalizuje i z tego powodu nie moze byc dokladnie oznaczona.Substancja ta przy ogrzaniu do wysokiej temperatury, albo jeszcze lepiej przy ogrzaniu z takiemi srodkami, jak chlorek glinu prze¬ chodzi w perylen. Wydajnosc przy zastosowaniu chlorku glinowego wynosi okolo 25%, a'e moze byc wypadkowo wyzsza.W powyzszych przykladach wykona¬ nia zamiast chlorku glinu moga byc uzyte inne odpowiednie zwiazki chlorowców7 i równiez moga byc stosowane" zamiast kwasu fosforawego inne kwasy fosforu. PL PLPrevious syntheses of perylene (Ber. 48s. 2202) from naphthalene - a-dinaphthyl or derivatives gave a slight yield, but it has now been found that the yield is significantly increased when [3-naphthalene or a-dinaphthyl derivatives are treated with chlorinating agents, such as chlorine compounds With phosphorus, antimony, arsenic, aluminum and the like, [3-chloro naphthalene derivatives or such α-dinaphthyl compounds are formed, which can then be converted into perylene by a known method, for example, with aluminum chloride or by pyrogenic means. It is also recommended to use reducing agents such as phosphorous acid. The reaction may take place in such a way that, starting from the substituted β-derivatives of naphthalene or α-dinaphthyl, the isolation of the substituted (3-halogen of this hydrocarbon, or it is not carried out. It is also possible to start with (3-halogena-α-dinaphtyl, by any means. EXAMPLES: 1. 1 kg of p-dinaphthol is heated quickly with 1 kg of phosphorous acid while adding 1 kg of phosphorus trichloride. The reaction takes place with a high foaming and formation of phosphine, which is It ignites by itself. After the evolution of this gas has ceased, the product is subjected to a partial distillation and thus separated from the concurrently formed dinaphthyl oxides. The yield of pure technical perylene is 60% of the starting material. Alternatively, the product may be crystallized from benzol or glacial acetic acid. and you get pure perylene in an amount of about 80% technical perylene. run either without or with the aid of the above-mentioned liquids. If the reactions are carried out pyrogenically without liquids, the yield is poorer. a) 1 kg of (3-dicbloro α-dinaphthyl is heated to 500-600 ° C and the reaction product is treated as in Example 1. The yield of technically pure perylene is 20% of the starting material. b) 1 kg (3-dichloro a- of dinaphthyl is heated to 500 ° C with the addition of 1 kg of phosphorous acid, and the reaction product is worked up as in Example 1, the result is technically pure perylene in the amount of 75% of the starting material. in example 1, but the mixture is heated in the same ratios to a lower temperature than those given in example 1, and the product cools without previous distillation, after boiling the cooled product with sodium or potassium liquor, dark-colored substances can be separated which does not crystallize and therefore cannot be accurately determined. When heated to high temperatures, or even better when heated with agents such as aluminum chloride, this substance is converted to perylene. It is about 25% or so may accidentally be higher. In the above embodiments, other suitable halogen compounds7 may be used in place of aluminum chloride, and also other phosphorus acids may be used in place of phosphorous acid. PL PL
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL85B1 true PL85B1 (en) | 1924-05-26 |
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2376008A (en) | Production of lutidine-urea compounds | |
| PL85B1 (en) | The method of obtaining perylene. | |
| US1726647A (en) | Substituted dithiocarbamates and method of making same | |
| US1891843A (en) | Signobs to imperial chemical industries limited | |
| US2210320A (en) | Manufacture of methacrylonitrile | |
| US2616899A (en) | Chlorinated epoxy compounds | |
| US1726648A (en) | Substituted dithiocarbamates and method of making same | |
| US1858659A (en) | Tri-diphenyl phosphate | |
| US2143816A (en) | Dithiohydantoins | |
| US3465037A (en) | Production of meso 2,3-dibromosuccinic acid | |
| US1384615A (en) | Fritz hansgirg | |
| US1596325A (en) | Process for the separation of ortho-chlorotoluene and parachlorotoluene | |
| US1431394A (en) | Process of purifying naphthalene | |
| US1887396A (en) | Aromatic halogen-methyl compound and alpha process of preparing it | |
| Le Fèvre et al. | CCLXXIV.—Orientation effects in the diphenyl series. Part III. The mononitro-4: 4′-dihalogenodiphenyls and some allied compounds | |
| US2748161A (en) | Method of forming phthalaldehydic acid from pentachloroxylene | |
| US1639658A (en) | Improved process for the manufacture of perylene | |
| US1840335A (en) | Process of manufacturing triaryl phosphates | |
| Worrall | Studies in the Biphenyl Series. IV. Some 0-Biphenyl Derivatives of Phosphorus, Arsenic and Antimony | |
| US3000936A (en) | 4,4-dinitro 1,7-heptanedioylchloride and method of making it | |
| US1814146A (en) | Process for the preparation of 4-halogen-beta-phenyl-anthraquinone | |
| US697994A (en) | Process of making thymol. | |
| AT200579B (en) | Process for the preparation of the new 5-dibenzo [b, f] azepines | |
| US3387936A (en) | Process for the manufacture of tetraphosphorus disulfide | |
| Rule et al. | 369. Bromo-and nitro-derivatives of naphthalic acid |