SU278690A1 - Method of producing phosphorus-containing isocyanates - Google Patents
Method of producing phosphorus-containing isocyanatesInfo
- Publication number
- SU278690A1 SU278690A1 SU1335257A SU1335257A SU278690A1 SU 278690 A1 SU278690 A1 SU 278690A1 SU 1335257 A SU1335257 A SU 1335257A SU 1335257 A SU1335257 A SU 1335257A SU 278690 A1 SU278690 A1 SU 278690A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- isocyanates
- producing phosphorus
- carried out
- nco
- containing isocyanates
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 239000012948 isocyanate Substances 0.000 title claims description 8
- 150000002513 isocyanates Chemical class 0.000 title claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 4
- 239000011574 phosphorus Substances 0.000 title claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 4
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 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 claims description 2
- 230000003993 interaction Effects 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- -1 dialkyl ether salts Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction 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
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Изобретение относитс к синтезу фосфорсодержащих изоцианатов общей формулыThis invention relates to the synthesis of phosphorus-containing isocyanates of the general formula
ГгYy
NCONCO
NHCOPOfOR)NHCOPOfOR)
где R и R-алкил, которые могут служить мономерами дл получени фосфорилированных полиуретанов и других разнообразных фосфорорганических соединений.where R and R-alkyl, which can serve as monomers for the preparation of phosphorylated polyurethanes and other various organophosphorus compounds.
Известен способ получени фосфорсодержащих изоцианатов взаимодействием солей диалкиловых эфиров дитиофосфорной КИСЛОТЫ или триалкилфосфитов с хлоралкилизоцианатами.A known method for the preparation of phosphorus-containing isocyanates is the interaction of the dialkyl ether salts of dithiophosphoric acid or trialkylphosphites with chloro-isyl isocyanates.
Дл повышени выхода конечных продуктов , а также расширени сырьевой базы предложено получать соединени взаимодействием толуилендиизоцианата с диалкилфосфористой кислотой в среде инертного органического растворител в присутствии катализатора, например металлического натри , с последующим выделением целевого продукта известными методами. Процесс лучше вести при нагревании до 50-60°С и эквимолекул рном количестве реагентов.To increase the yield of the final products, as well as expand the raw material base, it has been proposed to prepare compounds by reacting toluylene diisocyanate with dialkyl phosphorous acid in an inert organic solvent medium in the presence of a catalyst, for example metallic sodium, followed by isolation of the target product using known methods. The process is best carried out when heated to 50-60 ° C and an equimolar amount of reagents.
Пример. Реакции провод т с эквимолекул рным количеством 2,4-толуилендиизоцианата и диалкилфосфористых кислот. К раствору толуилендиизоцианата в безводном гексане при перемешивании прикапывают дналкилфосфористую кислоту, в которой предварительно растворен металлический натрий. Реакци начинаетс при 20°С н идет с незначительным разогреванием. Дл окончани реакции смесь нагревают на вод ной бане при 50-60°С в течение 1 час.Example. The reactions are carried out with an equimolar amount of 2,4-toluene diisocyanate and dialkyl phosphorous acids. To a solution of toluene diisocyanate in anhydrous hexane with stirring, drop alkyl phosphoric acid, in which sodium metal is previously dissolved, is added dropwise. The reaction starts at 20.degree. C. and takes place with a slight warming. To complete the reaction, the mixture is heated in a water bath at 50-60 ° C for 1 hour.
Продукт реакции выпадает в осадок, который при СТОЯНИИ кристаллизуетс . Полученные продукты легко раствор ютс в бензоле,The reaction product precipitates, which, upon STANDING, crystallizes. The products obtained are readily soluble in benzene,
ацетоне, диоксане. Их очищают перекристаллизацией из смеси бензола с гексаном. Константы и аналитические данные синтезированных изоцианатов представлены в таблице.acetone, dioxane. They are purified by recrystallization from a mixture of benzene and hexane. Constants and analytical data of the synthesized isocyanates are presented in the table.
Предмет изобретени Subject invention
Claims (3)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU278690A1 true SU278690A1 (en) |
Family
ID=
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