EP0000531A1 - Procédé de préparation de dialcoxyphosphonoalcoylcarbamates. - Google Patents
Procédé de préparation de dialcoxyphosphonoalcoylcarbamates. Download PDFInfo
- Publication number
- EP0000531A1 EP0000531A1 EP78100416A EP78100416A EP0000531A1 EP 0000531 A1 EP0000531 A1 EP 0000531A1 EP 78100416 A EP78100416 A EP 78100416A EP 78100416 A EP78100416 A EP 78100416A EP 0000531 A1 EP0000531 A1 EP 0000531A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- group
- carbamates
- alkenyl
- alkyl
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- -1 alkyl carbamates Chemical class 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title abstract description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 9
- 150000002978 peroxides Chemical class 0.000 claims abstract description 9
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 8
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 8
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 7
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 claims description 7
- 239000011261 inert gas Substances 0.000 claims description 4
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 description 15
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- OCAAZRFBJBEVPS-UHFFFAOYSA-N prop-2-enyl carbamate Chemical compound NC(=O)OCC=C OCAAZRFBJBEVPS-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- MNPKKYZUEZVQNJ-UHFFFAOYSA-N 2-methylprop-2-enyl carbamate Chemical compound CC(=C)COC(N)=O MNPKKYZUEZVQNJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OSSWQQQGZCWHIJ-UHFFFAOYSA-N C(N)(OCCCP(=O)(OOC)OOC)=O Chemical compound C(N)(OCCCP(=O)(OOC)OOC)=O OSSWQQQGZCWHIJ-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- UFFAFBPZFGAMJJ-UHFFFAOYSA-N (2-methoxy-4,6-dimethylphenyl)boronic acid Chemical compound COC1=CC(C)=CC(C)=C1B(O)O UFFAFBPZFGAMJJ-UHFFFAOYSA-N 0.000 description 1
- KMBSSXSNDSJXCG-UHFFFAOYSA-N 1-[2-(2-hydroxyundecylamino)ethylamino]undecan-2-ol Chemical compound CCCCCCCCCC(O)CNCCNCC(O)CCCCCCCCC KMBSSXSNDSJXCG-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- UZEFVQBWJSFOFE-UHFFFAOYSA-N dibutyl hydrogen phosphite Chemical compound CCCCOP(O)OCCCC UZEFVQBWJSFOFE-UHFFFAOYSA-N 0.000 description 1
- IXLIDZMVNVBMIT-UHFFFAOYSA-N ethyl methyl hydrogen phosphite Chemical compound CCOP(O)OC IXLIDZMVNVBMIT-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
Definitions
- Dialkoxyphosphonoalkylcarbamates are important as flame retardants for textile goods, especially those based on natural or regenerated cellulose.
- a technically interesting process for the preparation of these phosphorus-containing products consists in the reaction of dialkyl phosphites with alkenyl carbamates in the presence of peroxides as catalysts (DT-QSen 20 24 280 and 23 12 090).
- the dialkyl phosphites in excess namely in 2 - 4 times (DT-OS 20 24 280) or 1.5 - 5 times (DT-OS 23 12 090) molar amount -
- the DT-Open Nos len in the A us outsbeispie- the peroxidic catalysts in amounts of about 10 - 20 wt .-%, based on the carbamate used.
- Dialkyl phosphites of the formula (III) used for the process according to the invention are, for example, dimethyl phosphite, methyl ethyl phosphite, diethyl phosphite, dipropyl phosphite and di-butyl phosphite etc.; are preferred.
- Dimethyl and D iäthylphosphit are, for example, dimethyl phosphite, methyl ethyl phosphite, diethyl phosphite, dipropyl phosphite and di-butyl phosphite etc.
- alkyl carbamates (IV) examples include in question: allyl carbamate, methallyl carbamate, 2-methylbutene- (1) -yl-carbamate, butene- (1) -yl-carbamate, N, N'-ethylene-bis- (allyl carbamate). Allyl and methallyl carbamate, in particular allyl carbamate, are preferred.
- reaction temperatures are expediently chosen in the interval from approximately 120 ° to 170 ° C., preferably approximately 130 ° to 150 ° C.
- Peroxide catalysts are e.g. in question: di-tert-butyl peroxide, tert-butyl peroxybenzoate, 2,5-dimethyl bis-2,5- (peroxybenzoate), benzoyl peroxide.
- tert-butyl peroxybenzoate shows a preferred and particularly pronounced catalytic activity.
- the catalysts are expediently used in an amount of approximately 1 to 5% by weight, preferably approximately 2 to 4% by weight, based on the weight of the alkenyl carbamate used.
- Inert solvents can be used. As such, e.g. Use alcohols and ether.
- the end product can also be used as a solvent. In general, however, work is carried out in the absence of solvents.
- Nitrogen, argon and carbon dioxide are particularly suitable as such inert gases.
- the process is expediently and particularly preferably carried out in such a way that the dialkyl phosphite is heated to the required reaction temperature under an inert gas atmosphere and the alkenyl carbamate, mixed with the peroxide, is then metered in.
- the reaction is complete after 2 to 6 hours.
- the turnover is then generally over 90% of theory. Th.
- the starting materials can be reacted in a conventional manner in a different order. However, heating the premixed components together is not recommended, as this can lead to decomposition not only in technical approaches.
- the process can be carried out batchwise or continuously.
- any solvents used are distilled off.
- unreacted portions of the starting materials can be distilled off up to an internal temperature of about 120-150 ° C. and at a pressure of about 0.1 to 5 Torr.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2734454 | 1977-07-30 | ||
| DE2734454A DE2734454C2 (de) | 1977-07-30 | 1977-07-30 | Verfahren zur Herstellung von Dialkoxyphosphonoalkylcarbamaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0000531A1 true EP0000531A1 (fr) | 1979-02-07 |
| EP0000531B1 EP0000531B1 (fr) | 1980-07-23 |
Family
ID=6015243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP78100416A Expired EP0000531B1 (fr) | 1977-07-30 | 1978-07-18 | Procédé de préparation de dialcoxyphosphonoalcoylcarbamates. |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0000531B1 (fr) |
| DE (2) | DE2734454C2 (fr) |
| IT (1) | IT1097780B (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005103522A1 (fr) | 2004-04-20 | 2005-11-03 | Knorr-Bremse Systeme für Nutzfahrzeuge GmbH | Dispositif de reglage pour freins a disque a actionnement pneumatique et frein a disque |
| WO2014154969A1 (fr) | 2013-03-26 | 2014-10-02 | Saint-Gobain Glass France | Vitrage anti-feu |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2220537A1 (fr) * | 1973-03-10 | 1974-10-04 | Basf Ag | |
| FR2229705A1 (fr) * | 1973-05-19 | 1974-12-13 | Bayer Ag | |
| FR2258390A1 (fr) * | 1974-01-17 | 1975-08-18 | Bayer Ag |
-
1977
- 1977-07-30 DE DE2734454A patent/DE2734454C2/de not_active Expired
-
1978
- 1978-07-18 DE DE7878100416T patent/DE2860062D1/de not_active Expired
- 1978-07-18 EP EP78100416A patent/EP0000531B1/fr not_active Expired
- 1978-07-28 IT IT26271/78A patent/IT1097780B/it active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2220537A1 (fr) * | 1973-03-10 | 1974-10-04 | Basf Ag | |
| FR2229705A1 (fr) * | 1973-05-19 | 1974-12-13 | Bayer Ag | |
| FR2258390A1 (fr) * | 1974-01-17 | 1975-08-18 | Bayer Ag |
Non-Patent Citations (1)
| Title |
|---|
| JOURNAL OF ORGANIC CHEMISTRY, 25, Seiten 665-666 (1960) * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005103522A1 (fr) | 2004-04-20 | 2005-11-03 | Knorr-Bremse Systeme für Nutzfahrzeuge GmbH | Dispositif de reglage pour freins a disque a actionnement pneumatique et frein a disque |
| WO2014154969A1 (fr) | 2013-03-26 | 2014-10-02 | Saint-Gobain Glass France | Vitrage anti-feu |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0000531B1 (fr) | 1980-07-23 |
| DE2734454B1 (de) | 1979-01-04 |
| DE2734454C2 (de) | 1979-09-13 |
| IT1097780B (it) | 1985-08-31 |
| IT7826271A0 (it) | 1978-07-28 |
| DE2860062D1 (en) | 1980-11-13 |
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