GB2024224A - Production of peroxydicarbonates - Google Patents
Production of peroxydicarbonates Download PDFInfo
- Publication number
- GB2024224A GB2024224A GB7922900A GB7922900A GB2024224A GB 2024224 A GB2024224 A GB 2024224A GB 7922900 A GB7922900 A GB 7922900A GB 7922900 A GB7922900 A GB 7922900A GB 2024224 A GB2024224 A GB 2024224A
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- GB
- United Kingdom
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- percent
- chloroformate
- hydrogen peroxide
- weight
- alkali metal
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
- C07C407/003—Separation; Purification; Stabilisation; Use of additives
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A peroxydicarbonate represented by the formula R-OCO-OO-OCO-R, wherein R is an organic radical derived from a C1-18 monohydric alcohol is obtained by reacting, at a temperature of from -10 DEG C to 30 DEG C, a chloroformate of the formula R-OCO-Cl with an aqueous solution of hydrogen peroxide containing from 10 to 35 percent by weight of hydrogen perioxide and with an aqueous solution of alkali metal hydroxide containing 20 to 40 percent by weight of the hydroxide, sufficient of each of the peroxide and the hydroxide solutions being used to provide at least a 4 percent stoichiometric excess of the peroxide and at least a 1 percent stoichiometric excess of the hydroxide.
Description
SPECIFICATION
Production of peroxydicarbonates Pernxydicarbonates of the formula R-OCO-OO-OCO
R, wherein R is an organic radical derived from monohydric alcohols of the type ROH, are widely used as initiators in the polymerization of unsaturated monomers as described, for example, in U.S.
Patent 2,464,062.
The peroxydicarbonates are typically prepared by the so-called "peroxide slurry method" wherein a chloroformate of the formula R-OCO-CI (wherein R is as above defined) is reacted with a concentrated aqueous slurry of sodium peroxide as described, for example, in U.S. Patent 2,370,588.
It has been found, however, that during the addition of the sodium peroxide slurry to the reaction mixture, the reaction product tends to hydrolyze to form the corresponding alcohol resulting in an impure product having a reduced peroxydicarbonate assay. In addition, hydrolysis of the reaction product reduces the net yield of peroxydicarbonate.
Since the lower molecular weight alcohols, for example, ethanol, isopropanol, n-propanol,t- butanol, sec-butanol, and the like are relatively water soluble, such lower molecular weight alcoholic impurities can be readily removed from the peroxyicarbonate by washing with water However, since the water solubility of alcohols generally decreases with increasing molecular weight, the higher molcular weight alcoholic impurities such as, for example, 2-ethylhexanol, are not readily removed from the peroxydicarbonate by typical product purification means, e.g. water washing.
Regardless of the ease of removal of the alcoholic impurity formed by hydrolysis of the reaction product upon addition of the sodium peroxide slurry, the yield of peroxydicarbonate is reduced in proportion to the extent of hydrolysis.
We have found that high purity peroxydicarbonate can be produced in high yield by reacting a mixture containing chloroformate and dilute aqueous hydrogen peroxide with a dilute aqueous alkali metal hydroxide solution.
According to the present invention there is provided a process for preparing peroxydicarbonate represented by the formula R-OCO-OO-OCO-R, wherein R is an organic radical derived from a monohydric alcohol containing up to 18 carbon atoms, comprising reacting, at a temperature of from -10"C to 30"C, a chloroformate of the formula
R-OCO-CI wherein R is as defined above with an aqueous solution of hydrogen peroxide containing from about 10 percentto about 35 percent by weight of hydrogen peroxide and with an aqueous solution of alkali metal hydroxide containing about 20 percent to about 40 percent by weight of the hyrodoxide, sufficient of each of the peroxide and the hydroxide solutions being used as to provide at least a 4 percent stoichiometric excess of the peroxide and at least a 1 percent stoichiometric excess of the hydroxide, the excesses being based on the quantity of chloroformate, and recovering peroxydicarbonate from the reaction mixture.
In one embodiment of the present invention a process for preparing peroxydicarbonate separated by the formula R-OCO-OO-OCO-R wherein R is an organic radical derived from a monohydric alcohol containing-up to 18 carbon atoms is provided comprising reacting, at-a temperature of from -10"C to 300C an aqueous mixture containing a chioroformate of the formula R-OCO-CI wherein R is as defined above and at least about 4 percent stoichiometric excess of hydrogen peroxide based on the quantity of chloroformate, said mixture having a hydrogen peroxide content of from about 10 percent to about 35 percent by weight based on the quantity of water, with an at least 1 percent stoichiometric excess of alkali metal hydroxide based on the quantity of chloroformate, said alkali metal hydroxide being in the form of an aqueous solution containing from about 20 percent to about 40 percent by weight alkali metal hydroxide, and recovering peroxydicarbonate from the reaction mixture.
The invention is particularly applicable to producing di-n-propyl peroxydicarbonate (NPP), diisopropyl peroxydiearbonate (IPP), di-sec-butyl peroxydicarbonate (SBP), and di(2-ethylhexyl) peroxydicarbonate (EHP), although in its broadest aspects the invention contemplates the production of other peroxydicarbonates in addition to the preferred NPP,
IPP, SBP, and EHP.
Thus, although in the above formulae R preferably represents n-propyl, isopropyl, sec-butyl, and 2ethylhexyl, R may represent other linear or branched, substituted or unsubstituted alkyl or cycloalkyl radicals derived from a monohydric alcohol and containing up to about 18 carbon atoms. Other organic radicals of which R is representative include, for example, ethyl,butyl, n-butyl, isobutyl, t-butyl, hexyl, cyclohexyl, benzyl, 2-phenoxy ethyl, cetyl, allyl, tetradecyl, amyl, lauryl, and the like.
The chloroformate aqueous hydrogen peroxide mixture contains from aout 10 percent to 35 percent by weight and preferably from about 14 percent to about 30 percent by weight hydrogen peroxide based on the weight of water, with sufficient hydrogen peroxide being present to provide at least about a 4 percent stoichiometric excess and preferably an 8 percent to 12 percent stoichiometric excess of hydrogen peroxide based on the quantity of chloroformate.
The chloroformate aqueous hydrogen peroxide mixture may also contain from about 5 percent to about 15 percent, preferably about 10 percent by weight, based on the weight of chloroformate, of a lower alcohol or mixture of lower alcohols, such as, for example, methanol, ethanol, isopropanol, npropanol, or the like. The inclusion of a lower alcohol has been found to enable better reaction tempera ture cdntrol.
In order to produce high purity, i.e., 98 percent or higher, peroxydicarbonate, the chloroformate starting material, should, of course, be as pure as possible. Chloroformate having an assay of at least 99 percent is preferred for use in accordance with the invention.
The aqueous alkali metal hydroxide solution contains from about 20 percent to 40 percent by weight, preferably from about 25 percent to 35 percent by weight alkali metal hydroxide, sufficient of said solution being used for reaction with the chloroformate/hydrogen peroxide mixture to provide at least about a 1 percent and preferably from about 2 to 10 percent stoichiometric excess of alkali metal hydroxide based on the quantity of chloroformate.
The alkali metal hydroxide may be sodium hydroxide or potassium hydroxide as each has been found to give substantially equivalent results.
The reaction between the hydrogen peroxide/ chloroformate mixture and the alkali metal hydroxide solution is conducted with continuous stirring at a temperature of from about 0 C, to not more than about 30"C., preferably not more than about 1 5 C.
The alkali metal hydroxide solution is preferably added, with continuous stirring, to the hydrogen peroxide/chloroform ate mixture incrementally over a period of about 10 minutes to one hour, usually not more than about 30 minutes. Following the addition of the alkali metal hydroxide solution, the mixture is usually stirred for an additional period typically not more than about 30 minutes and usually not more than about 0 to 15 minutes to assure substantially complete conversion of chloroformate to peroxydicarbonate.
At the completion of the reaction, the liquid or solid peroxydicarbonate is recovered by any suitable conventional means, such as, for example, centrifugation as described in U.S. Patent 3,950,375. After recovery, the peroxydicarbonate is washed in known fashion with cold water to remove soluble impurities and dried; in the case of a iiquid prioxydicarbonate drying may be effected by contact with an inert drying agent, for example, magnesium sulfate, sodium sulphate, or the like.
Peroxydicarbonate assaying in excess of 98 percent with substantially quantitative conversion of chloroformate can routinely be obtained by the practice of this invention.
Although the invention has been described with particular reference to a preferred embodiment, it is evident that variations may be made therein without departing from the spirit and scope thereof. For example, it has been found that satisfactory results obtain by simultaneously adding a dilute aqueous hydrogen peroxide solution along with a dilute aqueous alkali metal hydroxide solution to the chloroformate. The respective strengths of said solutions and the stoichiometric excesses of hydrogen peroxide and alkali metal hydroxide are the same as described hereinabove with respect to the preferred manner of practicing the invention, i.e., by adding the alkali metal hydroxide solution to the hydrogen peroxide/chloroformate mixture.
The process of this invention enables the production of higher yields of higher purity peroxydicarbonate in a shorter reaction time with better reaction temperature control than the heretofore used peroxide slurry method.
The invention is further illustrated by the following examples.
Example 1
The reactor used consisted of a 1,000 milliliter capacity round bottom, three-neck flask. The flask was fitted with a pH electrode, a type "J" thermocouple, and a stirring rod having a TEFLONs paddle powered by a variable speed mixer. The temperature of the reactor was controlled by pumping ice water through a spay ring positioned around the reactor.
96.3 grams (0.5 mole) 2-ethylhexyl chloroformate, 65.1 grams of 14.1 weight percent aqueous hydrogen peroxide solution (0.27 mole H202), and 9.63 grams of isopropanol were added to the reactor. 81 grams of 25.7 weight percent aqueous sodium hydroxide solution (0.52 mole NaOH) were added to the reactor over a 25 minute period. After completion of the sodium hydroxide addition, the mixture was permitted to react for an additional 30 minutes.
Throughout the sodium hydroxide solution addition period and reaction period, the reactor contents were continuously stirred and maintained at a temperature of 15"C.
At the completion of the reaction, stirring was discontinued and the reaction mixture was permitted to phase separate. The organic phase was withdrawn, washed with cold water, dried with sodium sulphate, and submitted for analysis. Dit2- ethylhexyl) peroxydicarbonate product assaying at 99.3 percent was obtained.
Example 2
136.5 grams (1 mole) of sec-butyl chloroformate, 62 grams of 30.5 weight percent aqueous hydrogen peroxide solution (0.56 mole H2O2), and 13.65 grams ispropanol were added to the reactor described in
Example 1. 109 grams of 40.4 weight percent aqueous sodium hydroxide solution (1.1 moles
NaOH) were added to the reactor over a 30 minutes period and the reaction mixture was permitted to react an additional 30 minutes. The reactor contents were continuously stirred and maintained at a temperature of 15"C. throughout the addition of the sodium hydroxide solution and the reaction period.
At the completion of the reaction, stirring was discontinued, the reaction mixture was permitted to phase separate, the organic phase was withdrawn, washed with cold water, dried with sodium sulphate, and submitted for analysis. Di-sec-butyl peroxydicarbonate assaying at 99.2 percent was obtained.
Example 3
122.5 grams (1 mole) oushydroofisopropyl chloroformate and 91.3 grams of 20.5 weight percent aqueous hydrogen peroxide solution (0.55 moles
H202) were added to the reactor described in Example 1. 130 grams of 32.2 weight percent aqueous .
sodium hydroxide solution (1.05 moles NaOH) were added to the reactor over a 34 minute period and the reaction mixture was permitted to react over a 34 minute period and the reaction mixture was permitted to react an additional 30 minutes. The contents of the reactor were continuously stirred and maintained at a temperature of 1 5"C. throughout the addition of the sodium hydroxide solution and the reaction period.
At the completion of the reaction, stirring was discontinued, the reaction product was phase separated, the organic phase was withdrawn, washed with cold water, dried with sodium sulphate, and submitted for analysis. Diisopropyl peroxydicarbonate assaying at 99.0 percent was obtained.
Example 4
The procedure of Example 3 was followed except that n-propyl chloroformate was used in place of isopropyl chloroformate. Di-n-propyl peroxydicarbonate assaying at 99.4 percent was obtained.
Example 5
96.3 grams of 2-ethylhexyl chloroformate, 9.63 grams of isopropanol, and 25 grams of water were added to the reactor described in Example 1.40.94 grams of 50.8 percent aqueous sodium hydroxide solution was diluted with 25 grams of water. 18.18 grams of 50.5 percent aqueous hydrogen peroxide solution was diluted with 40 grams of water. Each solution had a volume of 53 milliliters. Each solution was added separately but simultaneously to the reactor via a dual-head Master Flex pump over a period of about 33 minutes. After completion of addition of the sodium hydroxide and hydrogen peroxide solutions, the mixture was permitted to react for an additional 30 minutes. Throughout the solution addition period and reaction period, the reactor contents were continuously stirred and maintained at a temperature of 15 C.
At the completion of the reaction, stirring was discontinued, the reaction mixture was permitted to phase separate, the organic phase was withdrawn, washed with cold water, dried with sodium sulphate, and submitted for analysis. Di(2-ethylhexyl) peroxydicarbonate assaying at 99.1 percent was obtained.
Although the invention has been described with specific references and specific details of embodiments thereof, it is to be understood that it is not intended to be so limited since changes and altera tionstherein may be made by those skilled in the art which are within the full intended scope of this invention as defined by the appended claims.
Claims (29)
1. A process for preparing peroxydicarbonate represented by the formula R-OCO-OO-OCO-R, wherein R is an organic radical derived from a monohydric alcohol containing up to 18 carbon atoms, comprising reacting, at a temperature of from -10 C to 30"C a chloroformate of the formula
R-OCO-CI wherein R is as defined above with an aqueous solution of hydrogen peroxide. containing from about 10 percent to about 35 percent by weight of hydrogen peroxide and with an aqueous solution of alkali metal hydroxide containing about 20 percent to about 40 percent by weight of the hydroxide, sufficient of each of the peroxide and the hydroxide solutions being used as to provide at least a 4 percent stoichiometric excess of the peroxide and at least a 1 percent stoichiometric excess of the hydroxide, the excesses being based on the quantity of chloroformate, and recovering peroxydicarbonate from the reaction mixture.
2. A process for preparing perioxydicarbonate represented by the formula R-OCO- OO-OCO-R, wherein R is an organic radical derived from a monohydric alcohol containing up to 18 carbon atoms, comprising reacting, at a temperature of from -10 C to 30"C an aqueous mixture containing a chloroformate of the formula R-OCO-CI wherein R is as defined above and at least about 4 percent stoichiometric excess of hydrogen peroxide based on the quantity of chloroformate, said mixture having a hydrogen peroxide content of from about 10 percent to about 35 percent by weight based on the quantity of water, with an at least 1 percent stoichiometric excess of alkali metal hydroxide based on the quantity of chloroformate, said alkali metal hydroxide being in the form of an aqueous solution containing from about 20 percent to about 40 percent by weight alkali metal hydroxide, and recovering perioxydicarbonate from the reaction mixture.
3. A process as claimed in claim 2, wherein the aqueous mixture contains from about 14 percent to about 30 percent by weight of hydrogen peroxide based on the quantity of water.
4. A process as claimed in claim 2 or 3, wherein the amount of hydrogen peroxide is sufficient to provide 4 percent to 12 percent stoichiometric excess based on the quantity of chloroformate.
5. A process as claimed in claim 4, wherein the amount of hydrogen peroxide is sufficient to provide an 8 percent to 12 percent stoichiometric excess based on the quantity of chloroformate.
6. A process as claimed in any of claims 2 to 5 wherein the chloroformate is n-propyl chloroformate, isopropyl chloroformate, sec-butyl chloroformate, or 2-ethylhexyl chloroformate.
7. A process as claimed in claim 6, wherein the chloroformate is sec-butyl chloroformate or 2ethylhexyl chloroformate and the chloroformatel hydrogen peroxide mixture contains from about 5 to about 15 percent by weight of a lower alcohol based on the weight of chloroformate.
8. A process as claimed in claim 7, wherein the amount of the alcohol is about 10 percent by weight based on the weight of chloroformate.
9. A process as claimed in claim 7 or 8, wherein the lower alcohol is methanol, ethanol, n-propanol, isopropanol, ort-butanol.
10. A process as claimed in any of claims 2 to 9, wherein the alkali metal hydroxide solution is added to the chloroformate/hydrogen peroxide mixture over a period of about 10 minutes to one hour.
11. A process as claimed in any of claims 2 to 10, wherein the alkali metal hydroxide solution contains from about 25 percent to about 35 percent by weight alkali metal hydroxide.
12. A process as claimed in any of claims 2 to 11, wherein sufficient alkali metal hydroxide is used so as to provide a 2 to 10 percent stoichiometric excess based on the quantity of chloroformate.
13. A process as claimed in any of claims 2 to 12, wherein the alkali metal hydroxide is sodium hydroxide or potassium hydroxide.
14. A process as claimed in any of claims 2 to 13, wherein the reaction is effected at a temperature of not more than about 15"C.
15. A process for preparing peroxydicarbonate represented by the formula R-OCO-OO-OCO-R, wherein R is an organic radical derived from an monohydricalcohol containing upto 18 carbon atoms, comprising reacting, at a temperature of from -10 C. to 30"C., a chloroformate of the formula
R-OCO-CI, wherein R is as defined above, with hydrogen peroxide and an alkali metal hydroxide, an aqueous solution containing from about 20 percent to 40 percent by weight of the alkali metal hydroxide and an aqueous solution containing from about 10 percent to 35 percent by weight of the hydrogen peroxide being added simultaneously and incrementally to the chloroformate, sufficient of each of said solutions being used so as to provide at last a 4 percent stoichiometric excess of hydrogen peroxide and at least a 1 percent stoichiometric excess of alkali metal hydroxide, said excesses being based on the quantity of chloroformate, and recovering peroxydicarbonate from the reaction mixture.
16. A process as claimed in claim 15, wherein the aqueous hydrogen peroxide solution contains from about 14 percent to about 30 percent by weight of hydrogen peroxide.
17. A process as claimed in claim 15 or 16, wheren the amount of hydrogen peroxide is sufficlient to provide a 4 percent to 12 percent stoichiomeetric excess based on the quantity of chloroformate.
18. A process as claimed in claim 17, wherein the amount of hydrogen peroxide is sufficient to provide an 8 to 12 percent stoichiometric excess based on the quantity of chloroformate.
19. A process as claimed in any of claims 15 to 18, wherein the chloroformate is n-propyl chloroformate, isopropyl chloroformate, sec-butyl chloroformate or 2-ethylhexyl chloroformate.
20. A process as claimed in claim 11, wherein the chloroformate is sec-butyl chloroformate or 2ethylhexyl chloroformate, and contains from about 5 percent to 15 percent by weight of a lower alcohol.
21. A process as claimed in claim 20, wherein the amount of the alcohol is about 10 percent by weight based on the weight of the chloroformate.
22. A process as claimed in claim 20 or 21, wherein the lower alcohol is methanol, ethanol, n-propanol, ispropanol or t-butanol.
23. A process as claimed in any of claims 15 to 22, wherein the alkali metal hydroxide solution and the hydrogen peroxide solution'are added to the chloroformate over a period of 10 minutes to one hour.
24. A process as claimed in any of claims 15 to 23, wherein the alkali metal hydroxide solution contains from about 25 percent to about 35 percent by weight alkali metal hydroxide.
25. A process as claimed in any of claims 15 to 24, wherein sufficient alkali metal hydroxide is used so as to provide 2 to 10 percent stoichiometric excess based on the quantity of chloroformate.
26. A process as claimed in any of claims 15 to 25, wherein the alkali metal hydroxide is sodium hydroxide or potassium hydroxide.
27. A process as claimed in any of claims 15 to 26, wherein the reaction is effected at a temperature of not more than about 15"C.
28. A process for preparing peroxydicarbonate substantially as hereinbefore described and with reference to any of the Examples.
29. Peroxydicarbonate whenever prepared by a process as claimed in any of claims 1 to 28.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92088678A | 1978-06-30 | 1978-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2024224A true GB2024224A (en) | 1980-01-09 |
Family
ID=25444566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7922900A Withdrawn GB2024224A (en) | 1978-06-30 | 1979-07-02 | Production of peroxydicarbonates |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS559067A (en) |
| DE (1) | DE2925868C2 (en) |
| FR (1) | FR2429785A1 (en) |
| GB (1) | GB2024224A (en) |
| NL (1) | NL7905039A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997027229A1 (en) * | 1996-01-25 | 1997-07-31 | Solvay (Societe Anonyme) | Process for the suspension polymerisation of vinyl chloride |
| CN102584663A (en) * | 2011-12-26 | 2012-07-18 | 淄博正华助剂股份有限公司 | Preparation method of solvent type peroxydicarbonate di-(2- ethylhexyl) ester with mass percent being 75 percent |
| CN102659960A (en) * | 2011-12-26 | 2012-09-12 | 淄博正华助剂股份有限公司 | Preparation method of solvent-type di-(2-ethylhexyl)peroxydicarbonate with mass fraction of 60% |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6433208B1 (en) * | 1999-11-04 | 2002-08-13 | Oxy Vinyls Lp | Method for producing stable, dilute, aqueous, emulsified peroxydicarbonates by homogenization |
| JP4940598B2 (en) * | 2004-08-27 | 2012-05-30 | 旭硝子株式会社 | Method for producing organic peroxide |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD62834A (en) * | ||||
| GB762183A (en) * | 1953-08-07 | 1956-11-28 | Ici Ltd | Improvements in or relating to the production of organic peroxides |
| JPS5147160B2 (en) * | 1972-08-22 | 1976-12-13 | ||
| JPS5287119A (en) * | 1976-01-12 | 1977-07-20 | Pennwalt Corp | Process for continuously manufacturing peroxydicarbonate |
-
1979
- 1979-06-26 JP JP8065879A patent/JPS559067A/en active Pending
- 1979-06-27 DE DE19792925868 patent/DE2925868C2/en not_active Expired
- 1979-06-28 NL NL7905039A patent/NL7905039A/en not_active Application Discontinuation
- 1979-06-29 FR FR7917062A patent/FR2429785A1/en not_active Withdrawn
- 1979-07-02 GB GB7922900A patent/GB2024224A/en not_active Withdrawn
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997027229A1 (en) * | 1996-01-25 | 1997-07-31 | Solvay (Societe Anonyme) | Process for the suspension polymerisation of vinyl chloride |
| US6258906B1 (en) | 1996-01-25 | 2001-07-10 | Solvay | Process for manufacture of a solution of dialkyl peroxydicarbonate |
| US6617408B2 (en) | 1996-01-25 | 2003-09-09 | Solvay (Societe Anonyme) | Process for polymerization of vinyl chloride |
| US6878840B2 (en) | 1996-01-25 | 2005-04-12 | Solvay (Societe Anonyme) | Process for polymerization of vinyl chloride |
| CN102584663A (en) * | 2011-12-26 | 2012-07-18 | 淄博正华助剂股份有限公司 | Preparation method of solvent type peroxydicarbonate di-(2- ethylhexyl) ester with mass percent being 75 percent |
| CN102659960A (en) * | 2011-12-26 | 2012-09-12 | 淄博正华助剂股份有限公司 | Preparation method of solvent-type di-(2-ethylhexyl)peroxydicarbonate with mass fraction of 60% |
| CN102659960B (en) * | 2011-12-26 | 2014-08-20 | 淄博正华助剂股份有限公司 | Preparation method of solvent-type di-(2-ethylhexyl)peroxydicarbonate with mass fraction of 60% |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2925868C2 (en) | 1982-09-30 |
| JPS559067A (en) | 1980-01-22 |
| FR2429785A1 (en) | 1980-01-25 |
| DE2925868A1 (en) | 1980-01-03 |
| NL7905039A (en) | 1980-01-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |