SU482948A3 - The method of obtaining 2-chloroethane phosphonic acid - Google Patents
The method of obtaining 2-chloroethane phosphonic acidInfo
- Publication number
- SU482948A3 SU482948A3 SU1724411A SU1724411A SU482948A3 SU 482948 A3 SU482948 A3 SU 482948A3 SU 1724411 A SU1724411 A SU 1724411A SU 1724411 A SU1724411 A SU 1724411A SU 482948 A3 SU482948 A3 SU 482948A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hydrogen chloride
- carried out
- phosphonic acid
- obtaining
- dichloroethane
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 title claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 14
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- LUVCTYHBTXSAMX-UHFFFAOYSA-N tris(2-chloroethyl) phosphite Chemical compound ClCCOP(OCCCl)OCCCl LUVCTYHBTXSAMX-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 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)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
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)
Description
(54) СПОСОБ ПОЛУЧЕНИЯ 2-ХЛОРЭТАНФОСФОНОВОЙ(54) METHOD FOR OBTAINING 2-CHLORETHANPHOSPHONE
КИСЛОТЫACIDS
введением хлористого водорода. Увлекаемое при этом количество хлористого водорода составл ет 20-100% необходимого дл расщеплени количества.the introduction of hydrogen chloride. The amount of hydrogen chloride entrained therewith is 20-100% of the amount required for cleavage.
По окончании реакции, которое определ ют по прекращению поглощени хлористого водорода и образовани дихлорэтана, реакционную смесь охлаждают до 70-80°С, снимают избыточное давление и обрабатывают по известной методике. Если дихлорэтан не отгон ют во врем реакции, то реакционна смесь расслаиваетс . Верхний слой состоит практически из чистого дихлорэтана. Нагреванием в вакууме из нижнего сло можно отогнать еще небольшое количество дихлорэтана, при этом остающа с 2-хлорэтанфосфонова кислота застывает в почти бесцветные кристаллы с точкой застывани 63-70°С.At the end of the reaction, which is determined by stopping the absorption of hydrogen chloride and the formation of dichloroethane, the reaction mixture is cooled to 70-80 ° C, the excess pressure is removed and treated according to a known method. If dichloroethane is not distilled off during the reaction, the reaction mixture is stratified. The top layer consists practically of pure dichloroethane. By heating in vacuum from the lower layer, a small amount of dichloroethane can be distilled off, while the remaining 2-chloroethane phosphonic acid solidifies into almost colorless crystals with a solidification point of 63-70 ° C.
Предлолсенный согласно изобретению способ сокращает расход хлористого водорода приблизительио до стехиометрического количества . Степень чистоты 2-хлорэтанфосфоновой кислоты, полученной этим способом, составл ет 95% и больще-и позвол ет использовать ее без дальнейшей очистки как ускоритель созревани . При этом в качестве исходного продукта может быть использован сырой продукт перегруппировки трис-(хлорэтил )-фосфита по Арбузову, содержащей более 50% неперегон емого поликонденсата.The process described in accordance with the invention reduces the consumption of hydrogen chloride to approximately stoichiometric amount. The purity of 2-chloro-ethanephosphonic acid obtained by this method is 95% and is more-and allows it to be used without further purification as a maturation accelerator. At the same time, as a starting product, a raw product of rearrangement of tris (chloroethyl) phosphite by Arbuzov containing more than 50% of non-distilled polycondensate can be used.
Следующие примеры показывают возможности осуществлени способа по предложенному изобретению.The following examples show the possibilities of carrying out the method according to the invention.
Пример 1. 3 кг сырого бис-2-хлорэтилового эфира 2-хлорэтанфосфоновой кислоты, содержащего 53% неперегон емых частей, нагревают до 150-160°С в эмалированном автоклаве емкостью 4 л с мешалкой, соединенном через вентиль и трубку из высококачественной стали с баллоном с хлористым водородом. При этом при перемешивании введением хлористого водорода поддерживают давление между 18 и 20 ати до тех пор пока поглощаетс хлористый водород (около 7 час).Example 1. 3 kg of crude 2-chloro-ethanephosphonic acid bis-2-chloroethyl ester containing 53% non-distillable parts is heated to 150-160 ° C in a 4 l enameled autoclave with an agitator connected through a valve and a stainless steel tube with a balloon with hydrogen chloride. At the same time, while stirring with the introduction of hydrogen chloride, the pressure is maintained between 18 and 20 atm until hydrogen chloride is absorbed (about 7 hours).
После удалени избыточного хлористого водорода реакционную смесь охлаждают до 70-80°С. Верхнюю фазу (1800 г), состо щую из 99% дихлорэтана, отдел ют низшую фазу весом 2196 г нагревают под вакуумом в течение 1 час на паровой бане. При этом в охлажденных до низких температур ловушках конденсируют еще 486 г 1,2-дихлорэтана. В остатке получают 1630 г 2-хлорэтаифосфоновой кислоты с температурой кристаллизации 68-69°С и степенью чистоты 96%.After removal of excess hydrogen chloride, the reaction mixture is cooled to 70-80 ° C. The upper phase (1800 g), consisting of 99% dichloroethane, is separated and the lower phase weighing 2196 g is heated under vacuum for 1 hour on a steam bath. At the same time, another 486 g of 1,2-dichloroethane is condensed in traps cooled to low temperatures. The residue gives 1630 g of 2-chloro-etyphosphonic acid with a crystallization temperature of 68-69 ° C and a purity of 96%.
Пример 2. В эмалированном, предназначенном дл эксплуатационного рабочего давлени 6 ати котле с мешалкой, соединенном через входной вентиль с баллоном с хлористым водородом и через выходной вентиль с пр мым холодильником, нагревают при перемешивании 84 кг сырого бис-2-хлорэтилового эфира 2-хлорэтанфосфоиовой кислоты, содержащего 53% неперегон емых частей, доExample 2. In an enameled, designed for operating working pressure of 6 bar, an agitated boiler connected through an inlet valve with a hydrogen chloride balloon and an outlet valve with a direct condenser, heated with stirring 84 kg of crude bis-2-chloroethyl ether 2-chloro-ethan-phosphoic acid, containing 53% non-distillable parts, to
150-160°С. Введением хлористого водорода создают давление 5-6 ати. Немного открыва выходной вентиль, пропусканием слабого тока хлористого водорода отгон ют образовавщийс во врем реакции 1,2-дихлорэтан, поддержива то же давление.150-160 ° C. The introduction of hydrogen chloride creates a pressure of 5-6 MPa. Slightly opening the outlet valve, passing 1,2-dichloroethane formed during the reaction to disperse a weak current of hydrogen chloride, while maintaining the same pressure.
Образование 1,2-дихлорэтана заканчиваетс через 16 час. Реакционную смесь нагревают еще в течение 1 час до около 160°С при 6 ати и затем охлаждают. После сн ти давлени The formation of 1,2-dichloroethane ends after 16 hours. The reaction mixture is heated for 1 hour to about 160 ° C at 6 ati and then cooled. After relieving pressure
содержащийс еще в реакционном продукте хлористый водород удал ют, пропуска азот при 100-160°С в течение 1 час, нагрева затем в течение 0,5 час в вакууме. Общее потребление хлористого водорода составл ет 42 кг. Получают 67 кг 1,2-дихлорэтана и 46 кг 2-хлорэтанфосфоновой кислоты с т. крист. 69°С и степенью чистоты 94-97%.the hydrogen chloride contained in the reaction product is removed, nitrogen is passed at 100-160 ° C for 1 hour, then heated for 0.5 hour in vacuum. The total consumption of hydrogen chloride is 42 kg. Get 67 kg of 1,2-dichloroethane and 46 kg of 2-chloroethane phosphonic acid with t. Cryst. 69 ° C and a degree of purity of 94-97%.
Предмет изобретени Subject invention
Claims (4)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2156284A DE2156284C3 (en) | 1971-11-12 | 1971-11-12 | Production of 2-chloroethane phosphonic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU482948A3 true SU482948A3 (en) | 1975-08-30 |
Family
ID=5824947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1724411A SU482948A3 (en) | 1971-11-12 | 1971-12-10 | The method of obtaining 2-chloroethane phosphonic acid |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5946960B2 (en) |
| AT (1) | AT309465B (en) |
| BE (1) | BE776736A (en) |
| CA (1) | CA942766A (en) |
| CH (1) | CH561224A5 (en) |
| CS (1) | CS164917B2 (en) |
| DE (1) | DE2156284C3 (en) |
| FR (1) | FR2159845A5 (en) |
| GB (1) | GB1356688A (en) |
| IL (1) | IL38341A (en) |
| IT (1) | IT943887B (en) |
| NL (1) | NL7116982A (en) |
| RO (1) | RO63331A (en) |
| SU (1) | SU482948A3 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1085870A (en) * | 1976-12-20 | 1980-09-16 | Robert J. Kiesel | Preparation of haloalylphosphonic acid |
| JPS6247576U (en) * | 1985-09-10 | 1987-03-24 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3787486A (en) * | 1969-10-17 | 1974-01-22 | Gaf Corp | Preparation of haloethane phosphonic acids |
-
1971
- 1971-11-12 DE DE2156284A patent/DE2156284C3/en not_active Expired
- 1971-12-08 CS CS8550A patent/CS164917B2/cs unknown
- 1971-12-10 SU SU1724411A patent/SU482948A3/en active
- 1971-12-10 CH CH1812171A patent/CH561224A5/xx not_active IP Right Cessation
- 1971-12-10 GB GB5746871A patent/GB1356688A/en not_active Expired
- 1971-12-10 NL NL7116982A patent/NL7116982A/xx unknown
- 1971-12-13 IL IL38341A patent/IL38341A/en unknown
- 1971-12-13 IT IT32310/71A patent/IT943887B/en active
- 1971-12-13 AT AT1067271A patent/AT309465B/en not_active IP Right Cessation
- 1971-12-14 RO RO7100069051A patent/RO63331A/en unknown
- 1971-12-14 FR FR7144826A patent/FR2159845A5/fr not_active Expired
- 1971-12-14 CA CA130,082A patent/CA942766A/en not_active Expired
- 1971-12-14 JP JP46100790A patent/JPS5946960B2/en not_active Expired
- 1971-12-15 BE BE776736A patent/BE776736A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AT309465B (en) | 1973-08-27 |
| IT943887B (en) | 1973-04-10 |
| CH561224A5 (en) | 1975-04-30 |
| DE2156284B2 (en) | 1979-12-06 |
| DE2156284A1 (en) | 1973-05-17 |
| GB1356688A (en) | 1974-06-12 |
| CA942766A (en) | 1974-02-26 |
| RO63331A (en) | 1978-08-15 |
| DE2156284C3 (en) | 1980-08-07 |
| JPS5946960B2 (en) | 1984-11-15 |
| CS164917B2 (en) | 1975-11-28 |
| IL38341A0 (en) | 1972-02-29 |
| FR2159845A5 (en) | 1973-06-22 |
| IL38341A (en) | 1974-06-30 |
| JPS4857929A (en) | 1973-08-14 |
| NL7116982A (en) | 1973-05-15 |
| BE776736A (en) | 1972-06-15 |
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