GB455014A - Process for the manufacture of esters of phosphoric acid - Google Patents
Process for the manufacture of esters of phosphoric acidInfo
- Publication number
- GB455014A GB455014A GB11500/35A GB1150035A GB455014A GB 455014 A GB455014 A GB 455014A GB 11500/35 A GB11500/35 A GB 11500/35A GB 1150035 A GB1150035 A GB 1150035A GB 455014 A GB455014 A GB 455014A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphorus
- phosphates
- retorts
- production
- mixture
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 title 1
- 150000002148 esters Chemical class 0.000 title 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 6
- 229910019142 PO4 Inorganic materials 0.000 abstract 5
- 235000021317 phosphate Nutrition 0.000 abstract 5
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 5
- -1 ethylphenyl Chemical group 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- RLBGTSMUBPSZKC-UHFFFAOYSA-N OP(O)O.Cl.Cl Chemical class OP(O)O.Cl.Cl RLBGTSMUBPSZKC-UHFFFAOYSA-N 0.000 abstract 2
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 229930003836 cresol Natural products 0.000 abstract 2
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 2
- 239000011261 inert gas Substances 0.000 abstract 2
- 230000007935 neutral effect Effects 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000002485 combustion reaction Methods 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 abstract 1
- 230000005484 gravity Effects 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- 238000011084 recovery Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B64—AIRCRAFT; AVIATION; COSMONAUTICS
- B64C—AEROPLANES; HELICOPTERS
- B64C17/00—Aircraft stabilisation not otherwise provided for
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Aviation & Aerospace Engineering (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)
Abstract
<PICT:0455014/IV/1> Organic hydroxy compounds are converted into their phosphates by passing a mixture of the hydroxy compound with phosphorus oxychloride, phosphorus pentachloride or phosphorus trichloride and chlorine through a series of zones of progressively increasing temperature. Catalysts such as aluminium chloride or zinc chloride may be present, and the reaction is preferably effected, when using phosphorus oxychloride, under high vacuum or in the presence of an inert gas. When using phosphorus pentachloride or phosphorus trichloride and chlorine, phosphite dichlorides are formed which require hydrolysis to the phosphates. The process is applicable to the production of neutral phosphates containing the same or different alkyl or aryl radicles; the aryl radicles may contain an ether substituent. Products mentioned are tributyl, triphenyl, tricresyl, trixylenyl, tri-(p-tert-amylphenyl), tri (ethylphenyl), tri-(methoxyethylphenyl), di(p-tert-amylphenyl)-monocresyl, mono(p - tert - amylphenyl)-monocresyl - mono (methoxyethyl) and di-(butylphenyl)-monophenyl phosphates. The preparation of tricresyl phosphate by passing a mixture of 3 mols of cresylic acid and 1 mol of phosphorus oxychloride through three retorts maintained at 150, 225 and 300 DEG C. respectively is described. The mixture passes by gravity from a mixing tank 11 to a preheater 13, thence through a flow meter 22 to three interconnected closed retorts 24, 27 and 28 arranged in series and located at different levels, and finally to a condenser 41. Each retort, which is heated by a combustion chamber 25, is divided by baffle plates 26 and is provided with a pipe 53 for the supply of carbon dioxide or other inert gas. Reflux condensers 43, 44 are connected to each retort and also to the preheater 13 for the return of condensible products while permitting the escape of hydrochloric acid gas to the flue 51 for recovery. The flue is preferably fitted with a suction device in order to reduce the pressure in the retorts. Reference is also made to the production of tricresyl phosphate by leading a mixture of 3 mols of cresol with 1 mol of phosphorus pentachloride through 3 retorts heated to temperatures of 50 DEG C., 75--100 DEG C., and 100--125 DEG C. respectively, and hydrolyzing the resulting tricresyl phosphite dichloride by treatment with water or caustic soda. Specification 450,454 is referred to. The Specification as open to inspection under Sect. 91 describes also the production of phosphites using phosphorus trichloride and refers to the preparation of tricresyl phosphite from cresol and phosphorus trichloride. It also refers to the production of neutral phosphates containing alkoxyalkyl radicles, e.g. ethoxyethyl. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US455014XA | 1912-10-08 | 1912-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB455014A true GB455014A (en) | 1936-10-12 |
Family
ID=21938251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11500/35A Expired GB455014A (en) | 1934-04-13 | 1935-04-13 | Process for the manufacture of esters of phosphoric acid |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR455014A (en) |
| GB (1) | GB455014A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2450903A (en) * | 1945-01-17 | 1948-10-12 | Standard Oil Dev Co | Phosphorus acid esters of petroleum phenols |
| US2694083A (en) * | 1950-02-20 | 1954-11-09 | Douglas Aircraft Co Inc | Tri-(fluoralkyl phenyl) phosphates and method for producing them |
| FR2306210A1 (en) * | 1974-04-01 | 1976-10-29 | Hoechst Ag | PROCESS FOR PREPARATION OF ESTERS CONTAINING PHOSPHORUS |
| CN116983926A (en) * | 2023-09-22 | 2023-11-03 | 天津凯莱英医药科技发展有限公司 | Continuous production device and method for ethephon intermediate |
-
1913
- 1913-03-04 FR FR455014A patent/FR455014A/en not_active Expired
-
1935
- 1935-04-13 GB GB11500/35A patent/GB455014A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2450903A (en) * | 1945-01-17 | 1948-10-12 | Standard Oil Dev Co | Phosphorus acid esters of petroleum phenols |
| US2694083A (en) * | 1950-02-20 | 1954-11-09 | Douglas Aircraft Co Inc | Tri-(fluoralkyl phenyl) phosphates and method for producing them |
| FR2306210A1 (en) * | 1974-04-01 | 1976-10-29 | Hoechst Ag | PROCESS FOR PREPARATION OF ESTERS CONTAINING PHOSPHORUS |
| CN116983926A (en) * | 2023-09-22 | 2023-11-03 | 天津凯莱英医药科技发展有限公司 | Continuous production device and method for ethephon intermediate |
Also Published As
| Publication number | Publication date |
|---|---|
| FR455014A (en) | 1913-07-21 |
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