DE1518741C2 - Verfahren zur Herstellung von aliphatischen Diacylperoxiden mit 8 bis 18 Kohlenstoffatomen je Acylrest - Google Patents
Verfahren zur Herstellung von aliphatischen Diacylperoxiden mit 8 bis 18 Kohlenstoffatomen je AcylrestInfo
- Publication number
- DE1518741C2 DE1518741C2 DE1518741A DEE0028487A DE1518741C2 DE 1518741 C2 DE1518741 C2 DE 1518741C2 DE 1518741 A DE1518741 A DE 1518741A DE E0028487 A DEE0028487 A DE E0028487A DE 1518741 C2 DE1518741 C2 DE 1518741C2
- Authority
- DE
- Germany
- Prior art keywords
- percent
- hydrogen peroxide
- weight
- carboxylic acid
- reaction
- 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 18
- 239000012933 diacyl peroxide Substances 0.000 title claims description 11
- 125000001931 aliphatic group Chemical group 0.000 title claims 4
- 125000004432 carbon atom Chemical group C* 0.000 title claims 3
- 238000002360 preparation method Methods 0.000 title claims 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 12
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 9
- 239000000839 emulsion Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 6
- -1 carboxylic acid chlorides Chemical class 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000003995 emulsifying agent Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 239000006260 foam Substances 0.000 claims description 3
- 238000005187 foaming Methods 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 5
- 150000008065 acid anhydrides Chemical class 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 238000009835 boiling Methods 0.000 claims 2
- 238000000354 decomposition reaction Methods 0.000 claims 2
- 230000035484 reaction time Effects 0.000 claims 2
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 1
- 230000002411 adverse Effects 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000001804 emulsifying effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008149 soap solution Substances 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 8
- 150000002978 peroxides Chemical class 0.000 description 6
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- NWADXBLMWHFGGU-UHFFFAOYSA-N dodecanoic anhydride Chemical compound CCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCC NWADXBLMWHFGGU-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- NGEZPLCPKXKLQQ-VOTSOKGWSA-N (e)-4-(3-methoxyphenyl)but-3-en-2-one Chemical compound COC1=CC=CC(\C=C\C(C)=O)=C1 NGEZPLCPKXKLQQ-VOTSOKGWSA-N 0.000 description 1
- 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 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
- QMXBAGNATMRETP-UHFFFAOYSA-N hexadecanoyl hexadecaneperoxoate Chemical compound CCCCCCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCCCCCC QMXBAGNATMRETP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- XNTUJOTWIMFEQS-UHFFFAOYSA-N octadecanoyl octadecaneperoxoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCCCCCCCC XNTUJOTWIMFEQS-UHFFFAOYSA-N 0.000 description 1
- WVJVHUWVQNLPCR-UHFFFAOYSA-N octadecanoyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCC WVJVHUWVQNLPCR-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 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 1
- LPWCRLGKYWVLHQ-UHFFFAOYSA-N tetradecanoyl chloride Chemical compound CCCCCCCCCCCCCC(Cl)=O LPWCRLGKYWVLHQ-UHFFFAOYSA-N 0.000 description 1
- SLFUZVJZPBHLAQ-UHFFFAOYSA-N tetradecanoyl tetradecaneperoxoate Chemical compound CCCCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCCCC SLFUZVJZPBHLAQ-UHFFFAOYSA-N 0.000 description 1
- RCRYHUPTBJZEQS-UHFFFAOYSA-N tetradecanoyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCC RCRYHUPTBJZEQS-UHFFFAOYSA-N 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
Classifications
-
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0028487 | 1965-01-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1518741B1 DE1518741B1 (de) | 1975-10-30 |
| DE1518741C2 true DE1518741C2 (de) | 1980-06-19 |
Family
ID=7092900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1518741A Expired DE1518741C2 (de) | 1965-01-08 | 1965-01-08 | Verfahren zur Herstellung von aliphatischen Diacylperoxiden mit 8 bis 18 Kohlenstoffatomen je Acylrest |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE1518741C2 (en, 2012) |
| FR (1) | FR1462909A (en, 2012) |
| GB (1) | GB1135372A (en, 2012) |
| NL (1) | NL6517064A (en, 2012) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11976034B2 (en) | 2019-06-12 | 2024-05-07 | Nouryon Chemicals International B.V. | Process for the production of diacyl peroxides |
| US11976035B2 (en) | 2019-06-12 | 2024-05-07 | Nouryon Chemicals International B.V. | Process for the production of diacyl peroxides |
| US12209065B2 (en) | 2019-06-12 | 2025-01-28 | Nouryon Chemicals International B.V. | Process for the production of diacyl peroxides |
| US12215074B2 (en) | 2019-06-12 | 2025-02-04 | Nouryon Chemicals International B.V. | Process for the production of peroxyesters |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107250109A (zh) * | 2014-11-28 | 2017-10-13 | 联合创始人有限公司 | 用于制备粉末状的过氧化月桂酰的方法 |
| CN111393344B (zh) * | 2020-04-02 | 2022-02-25 | 鄂尔多斯市瀚博科技有限公司 | 一种过氧化二-（3,5,5-三甲基己酰）的制备方法 |
| CN116891429A (zh) * | 2023-07-27 | 2023-10-17 | 江苏强盛功能化学股份有限公司 | 一种过氧化月桂酰的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1718609A (en) * | 1929-06-25 | Amd vaman r | ||
| DE540588C (de) * | 1926-10-16 | 1932-01-04 | Ralph Harper Mckee | Verfahren zur Herstellung von Peroxyden organischer Saeuren |
| GB334531A (en) * | 1929-05-27 | 1930-08-27 | Pilot Lab Inc | Improvements in bleaching methods and compositions |
| DE934592C (de) * | 1936-07-03 | 1955-10-27 | Hoechst Ag | Verfahren zur Herstellung von Acylsuperoxyden |
| US2262431A (en) * | 1939-10-24 | 1941-11-11 | Armour & Co | Process of preparing high molecular weight fatty acid chlorides |
| NL270329A (en, 2012) * | 1960-10-31 |
-
1965
- 1965-01-08 DE DE1518741A patent/DE1518741C2/de not_active Expired
- 1965-12-29 NL NL6517064A patent/NL6517064A/xx unknown
-
1966
- 1966-01-06 FR FR45042A patent/FR1462909A/fr not_active Expired
- 1966-01-07 GB GB90266A patent/GB1135372A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11976034B2 (en) | 2019-06-12 | 2024-05-07 | Nouryon Chemicals International B.V. | Process for the production of diacyl peroxides |
| US11976035B2 (en) | 2019-06-12 | 2024-05-07 | Nouryon Chemicals International B.V. | Process for the production of diacyl peroxides |
| US12209065B2 (en) | 2019-06-12 | 2025-01-28 | Nouryon Chemicals International B.V. | Process for the production of diacyl peroxides |
| US12215074B2 (en) | 2019-06-12 | 2025-02-04 | Nouryon Chemicals International B.V. | Process for the production of peroxyesters |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1518741B1 (de) | 1975-10-30 |
| FR1462909A (fr) | 1966-12-16 |
| GB1135372A (en) | 1968-12-04 |
| NL6517064A (en, 2012) | 1966-07-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Publication of the examined application without previous publication of unexamined application | ||
| C2 | Grant after previous publication (2nd publication) |