NO138140B - PROCEDURE FOR THE PREPARATION OF 4,4`-DITERT.BUTYL-BENZOYL PEROXIDE - Google Patents
PROCEDURE FOR THE PREPARATION OF 4,4`-DITERT.BUTYL-BENZOYL PEROXIDE Download PDFInfo
- Publication number
- NO138140B NO138140B NO2741/73A NO274173A NO138140B NO 138140 B NO138140 B NO 138140B NO 2741/73 A NO2741/73 A NO 2741/73A NO 274173 A NO274173 A NO 274173A NO 138140 B NO138140 B NO 138140B
- Authority
- NO
- Norway
- Prior art keywords
- butyl
- benzoyl peroxide
- tert
- reaction
- temperature
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 239000004342 Benzoyl peroxide Substances 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title abstract description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- WNLMYNASWOULQY-UHFFFAOYSA-N 4-tert-butylbenzoyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)C=C1 WNLMYNASWOULQY-UHFFFAOYSA-N 0.000 claims description 5
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 claims 1
- 230000007717 exclusion Effects 0.000 claims 1
- UPIWXMRIPODGLE-UHFFFAOYSA-N butyl benzenecarboperoxoate Chemical compound CCCCOOC(=O)C1=CC=CC=C1 UPIWXMRIPODGLE-UHFFFAOYSA-N 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- -1 alkylaryl sulphonate Chemical compound 0.000 description 3
- 239000012933 diacyl peroxide Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/32—Peroxy compounds the —O—O— group being bound between two >C=O groups
- C07C409/34—Peroxy compounds the —O—O— group being bound between two >C=O groups both belonging to carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
- Polymerization Catalysts (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
Abstract
Fremgangsmåte for fremstilling av 4,4'-ditert. butyl-benzoylperoksyd.Process for the preparation of 4,4'-ditert. butyl benzoyl peroxide.
Description
Oppfinnelsen vedrører en ny fremgangsmåte for fremstilling av 4 ,4'-ditert,.butyl-benzoylperoksyd ut fra 4-tert.-butyl-benzosyreklorid. The invention relates to a new process for the production of 4,4'-di-tert-butyl-benzoyl peroxide from 4-tert-butyl-benzoic acid chloride.
4-tert.butyl-benzosyreklorid, som fremstilles i indust-rien, er allerede blitt anvendt for fremstilling av 4 ,4'-ditert.-butyl-benzoylperoksyd. Den vanlige metode som anvendes, består i å behandle 4-tert.butyl-benzosyreklorid i løsning i et hydro-karbon, med en vandig løsning av natriumperoksyd, ved en temperatur rundt 0°C. Utbyttene som oppnås ved denne metode, er alltid meget dårlige, av størrelsesorden 10 %. 4-tert-butyl-benzoic acid chloride, which is produced in industry, has already been used for the production of 4,4'-di-tert-butyl-benzoyl peroxide. The usual method used consists in treating 4-tert.butyl-benzoic acid chloride in solution in a hydrocarbon, with an aqueous solution of sodium peroxide, at a temperature around 0°C. The yields obtained by this method are always very poor, of the order of 10%.
Fra tysk utlegningsskrift nr. 1 643 151 er det kjent It is known from German specification document no. 1 643 151
å fremstille diacylperoksyder ved omsetning av et syreklorid med en vandig basisk hydrogenperoksydoppløsning i nærvær av et overflateaktivt middel. Fremstillingen av disse forbindelser fore- to prepare diacyl peroxides by reacting an acid chloride with an aqueous basic hydrogen peroxide solution in the presence of a surfactant. The production of these compounds pre-
tas ved lav temperatur, nemlig ca. 0°C. taken at a low temperature, namely approx. 0°C.
Fra britisk patentskrift nr. 496 214 er det kjent å fremstille diacylperoksyder ved omsetning av et syreklorid med en vandig basisk hydrogenperoksydoppløsning i fravær av oppløsnings-middel og i nærvær av et overflateaktivt middel, hvor reaksjonsme-diet er avkjølt. Det må således antas at den anvendte fremgangsmåte er den klassiske fremgangsmåte ved lav temperatur, mens man ved fremgangsmåten ifølge oppfinnelsen,som anført nedenunder, an-vender en relativt høy temperatur, nemlig 30-35°C. From British patent no. 496 214 it is known to prepare diacyl peroxides by reacting an acid chloride with an aqueous basic hydrogen peroxide solution in the absence of a solvent and in the presence of a surfactant, where the reaction medium is cooled. It must therefore be assumed that the method used is the classic method at a low temperature, while in the method according to the invention, as stated below, a relatively high temperature is used, namely 30-35°C.
I motsetning til de ovennevnte skrifter beskriver fransk patentskrift nx. 1 329 593 fremstillingen av diacylperoksyder ved behandling av et syreklorid med en vandig basisk hydrogenperoksyd-oppløsning ved høy temperatur,, hvor man arbeider i fravær av opp-løsningsmiddel .(eksempel 7). Det er i patentskriftet angitt at lave temperaturer gir gunstige betingelser for gjennomføring av fremgangsmåten, men at man kan arbeide ved en høyere temperatur for å oppnå en kortere reaksjonstid. De anvendte temperaturer er. mellom 40 og 65°C, fortrinnsvis mellom 50 og 60°C. Når man Ifølge dette patentskrift arbeider i fravær av oppløsningsmiddel, er reaksjonstiden mellom 30 sekunder og 5 minutter, og reaktantene avkjøles derpå hurtig til omgivelsestemperaturen. I eksempel 7, som angår fremstillingen av benzoylperoksyd, er temperaturen 50°C, og reaksjonstiden 2 minutter, hvorpå reaktantene avkjøles hurtig» In contrast to the above documents, French patent document nx. 1 329 593 the production of diacyl peroxides by treating an acid chloride with an aqueous basic hydrogen peroxide solution at high temperature, where one works in the absence of solvent (example 7). It is stated in the patent that low temperatures provide favorable conditions for carrying out the method, but that one can work at a higher temperature to achieve a shorter reaction time. The temperatures used are between 40 and 65°C, preferably between 50 and 60°C. When working in the absence of solvent according to this patent, the reaction time is between 30 seconds and 5 minutes, and the reactants are then rapidly cooled to ambient temperature. In example 7, which relates to the preparation of benzoyl peroxide, the temperature is 50°C and the reaction time 2 minutes, after which the reactants are cooled rapidly"
Det ses således av dette at anvendelsen av en høy temperatur nødvendiggjør en oppvarmningstid, som er begrenset til It can thus be seen from this that the use of a high temperature necessitates a heating time, which is limited to
noen minutter, hvis ikke produktene skal dekomponeres. a few minutes, if the products are not to decompose.
Det er således hverken på bakgrunn av dette patentskrift eller de øvrige patentskrifter mulig å forutse at man ved fremgangsmåten ifølge oppfinnelsen ved å anvende en så høy temperatur som 30-35°C og en så lang reaksjonstid som 105 minutter allikevel kunne oppnå så høye utbytter som 99 % av 4,4'-ditert.-butyl-benzoylperoksyd med en særdeles god renhet. It is thus neither on the basis of this patent document nor the other patent documents possible to predict that with the method according to the invention, by using a temperature as high as 30-35°C and a reaction time as long as 105 minutes, yields as high as 99% of 4,4'-di-tert-butyl-benzoyl peroxide with an extremely good purity.
Oppfinnelsen tilveiebringer således en fremgangsmåte for fremstilling av 4,4'-ditert.butyl-benzoylperoksyd ved omsetning av 4-tert.butyl-benzosyreklorid med en vandig, basisk hydrogenperoksydløsning under utelukkelse av oppløsningsmiddel og i nærvær av et overflateaktivt middel, og fremgangsmåten er karakterisert ved at omsetningen utføres ved en temperatur mellom 30 og 35°C under anvendelse av et alkylarylsulfonat som overflateaktivt middel. strukturformelen for 4,4'-ditert.butyl-benzoylperoksyd er som følger: The invention thus provides a method for the production of 4,4'-di-tert-butyl-benzoyl peroxide by reacting 4-tert-butyl-benzoic acid chloride with an aqueous, basic hydrogen peroxide solution while excluding solvent and in the presence of a surface-active agent, and the method is characterized in that the reaction is carried out at a temperature between 30 and 35°C using an alkylaryl sulphonate as surfactant. the structural formula for 4,4'-di-tert.butyl-benzoyl peroxide is as follows:
Høyere temperaturer enn 35°C er uheldige på grunn av faren for en dekomponering av hydrogenperoksyd og det ved reaksjonen dannede peroksyd. Higher temperatures than 35°C are unfavorable due to the danger of a decomposition of hydrogen peroxide and the peroxide formed by the reaction.
Det har overraskende vist seg at tilstedeværelsen av det karbonhydrid-løsningsmiddel som ble anvendt ved noen av de kjente fremgangsmåter, hadde en nedsettende virkning på utbyttet. It has surprisingly turned out that the presence of the hydrocarbon solvent used in some of the known methods had a reducing effect on the yield.
Mengden av hydrogenperoksyd som anvendes ved fremgangsmåten i henhold til oppfinnelsen, er vanligvis over den støkio-metriske mengde, for å unngå en eventuell spaltning under reaksjonen. Dette overskudd kan f.eks. være 20 til 30 %. Mengden av alkalisk substans som anvendes, er slik at blandingens pH-verdi er basisk eller nøytral ved slutten av reaksjonen. De alkaliske substanser som foretrekkes, er uorganiske baser, f.eks. natriumhydroksyd og kaliumhydroksyd- The amount of hydrogen peroxide used in the method according to the invention is usually above the stoichiometric amount, in order to avoid any decomposition during the reaction. This surplus can e.g. be 20 to 30%. The amount of alkaline substance used is such that the pH value of the mixture is basic or neutral at the end of the reaction. The alkaline substances which are preferred are inorganic bases, e.g. sodium hydroxide and potassium hydroxide
Ved fremgangsmåten ifølge oppfinnelsen utføres reaksjonen i nærvær av en liten mengde overflateaktivt middel av typen alkylarylsulfonat, hvorved man effektivt forhindrer agglomerering av peroksydpartiklene. In the method according to the invention, the reaction is carried out in the presence of a small amount of surfactant of the alkylaryl sulphonate type, whereby agglomeration of the peroxide particles is effectively prevented.
4,4'-ditert.butyl-benzoylperoksyd anvendes spesielt 4,4'-di-tert-butyl-benzoyl peroxide is used in particular
som polymerisasjonskatalysator. Dets varmestabilitet/som er noe lavere enn for benzoylperoksyd, gjør det meget anvendelig for polymerisasjoner ved lav temperatur (polyestere, polystyren osv.). as polymerization catalyst. Its thermal stability/which is somewhat lower than that of benzoyl peroxide, makes it very useful for polymerizations at low temperature (polyesters, polystyrene, etc.).
Det følgende eksempel gis for å belyse fremgangsmåten The following example is given to illustrate the procedure
i henhold til oppfinnelsen. according to the invention.
EKSEMPEL EXAMPLE
I en glasskolbe på 250 cm 3, avkjølt utvendig av is og utstyrt med røreverk, termometer og en brom-ampulle, anbringes 14,5 g 30 % hydrogenperoksyd (0,128 mol) og 37 g vann. Man til-setter langsomt (i Jøpet av ca. 15 minutter, ved en temperatur under 10°C) 24,2 -g av en 35 % løsning av natriumhydroksyd (0,212 mol) og deretter 1 cm<3> av en 1 % løsning av alkylarylsulfonat av handelsvaren "Erganol". Man omrører kraftig i reaksjonsblandin-gen og innfører langsomt 0,2 mol 4-tert.butyl-b<p>n^osyreklorid14.5 g of 30% hydrogen peroxide (0.128 mol) and 37 g of water are placed in a 250 cm 3 glass flask, cooled on the outside by ice and equipped with a stirrer, thermometer and a bromine ampoule. 24.2 g of a 35% solution of sodium hydroxide (0.212 mol) and then 1 cm<3> of a 1% solution are added slowly (over a period of approx. 15 minutes, at a temperature below 10°C) of alkylaryl sulphonate of the trade name "Erganol". The reaction mixture is stirred vigorously and 0.2 mol of 4-tert-butyl-b<p>n^oic acid chloride is slowly introduced
(30 minutter, idet temperaturen er mellom 30 og 35°C). Etter til-setningen fortsettes omrøringen i 75 minutter. Man filtrerer så. Man avslutter med to vaskinger på 30 minutter med 200 cm 3 vann, filtrerer og tørker under vakuum. (30 minutes, the temperature being between 30 and 35°C). After the addition, stirring is continued for 75 minutes. You then filter. Finish with two 30-minute washes with 200 cm 3 of water, filter and dry under vacuum.
Det.oppnådde 4,4'-ditert.butyl-benzoylperoksyd har en renhet på 99,5 %. Utbyttet, regnet på syrekloridet, er 99 %. The obtained 4,4'-di-tert-butyl-benzoyl peroxide has a purity of 99.5%. The yield, calculated on the acid chloride, is 99%.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7224372A FR2190800B1 (en) | 1972-07-05 | 1972-07-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO138140B true NO138140B (en) | 1978-04-03 |
| NO138140C NO138140C (en) | 1978-07-12 |
Family
ID=9101406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO274173A NO138140C (en) | 1972-07-05 | 1973-07-04 | PROCEDURE FOR THE PREPARATION OF 4,4`-DITERT.BUTYL-BENZOYL PEROXIDE |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS4951240A (en) |
| BE (1) | BE801709A (en) |
| CH (1) | CH573908A5 (en) |
| DE (1) | DE2334269C3 (en) |
| DK (1) | DK134987B (en) |
| ES (1) | ES416599A1 (en) |
| FR (1) | FR2190800B1 (en) |
| GB (1) | GB1429212A (en) |
| IE (1) | IE37863B1 (en) |
| IT (1) | IT994081B (en) |
| LU (1) | LU67920A1 (en) |
| NL (1) | NL7309298A (en) |
| NO (1) | NO138140C (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3038164A1 (en) * | 1980-10-09 | 1982-05-06 | Peroxid-Chemie GmbH, 8023 Höllriegelskreuth | METHOD FOR THE CONTINUOUS PRODUCTION OF DIALKYL PEROXYDICARBONATES |
| CN118530152B (en) * | 2024-05-14 | 2024-12-10 | 滨化技术有限公司 | Method for preparing dibenzoyl peroxide by TS-1 catalysis |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE934592C (en) * | 1936-07-03 | 1955-10-27 | Hoechst Ag | Process for the preparation of acyl peroxides |
-
1972
- 1972-07-05 FR FR7224372A patent/FR2190800B1/fr not_active Expired
-
1973
- 1973-06-29 BE BE132949A patent/BE801709A/en not_active IP Right Cessation
- 1973-07-02 IE IE109673A patent/IE37863B1/en unknown
- 1973-07-02 LU LU67920A patent/LU67920A1/xx unknown
- 1973-07-03 JP JP7517073A patent/JPS4951240A/ja active Pending
- 1973-07-03 IT IT5120273A patent/IT994081B/en active
- 1973-07-03 CH CH968273A patent/CH573908A5/xx not_active IP Right Cessation
- 1973-07-04 DK DK370373A patent/DK134987B/en unknown
- 1973-07-04 NL NL7309298A patent/NL7309298A/xx active Search and Examination
- 1973-07-04 NO NO274173A patent/NO138140C/en unknown
- 1973-07-05 ES ES416599A patent/ES416599A1/en not_active Expired
- 1973-07-05 DE DE19732334269 patent/DE2334269C3/en not_active Expired
- 1973-07-05 GB GB3213173A patent/GB1429212A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2190800B1 (en) | 1975-03-07 |
| NO138140C (en) | 1978-07-12 |
| DK134987B (en) | 1977-02-21 |
| DK134987C (en) | 1977-07-18 |
| DE2334269B2 (en) | 1978-05-18 |
| JPS4951240A (en) | 1974-05-18 |
| NL7309298A (en) | 1974-01-08 |
| DE2334269C3 (en) | 1983-11-24 |
| DE2334269A1 (en) | 1974-01-31 |
| IE37863L (en) | 1974-01-05 |
| FR2190800A1 (en) | 1974-02-01 |
| GB1429212A (en) | 1976-03-24 |
| BE801709A (en) | 1974-01-02 |
| IT994081B (en) | 1975-10-20 |
| LU67920A1 (en) | 1974-01-18 |
| CH573908A5 (en) | 1976-03-31 |
| ES416599A1 (en) | 1976-03-01 |
| IE37863B1 (en) | 1977-10-26 |
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