DE2230794C3 - Verfahren zur Trennung von Orthophosphorsäuremono- und di'estern - Google Patents
Verfahren zur Trennung von Orthophosphorsäuremono- und di'esternInfo
- Publication number
- DE2230794C3 DE2230794C3 DE19722230794 DE2230794A DE2230794C3 DE 2230794 C3 DE2230794 C3 DE 2230794C3 DE 19722230794 DE19722230794 DE 19722230794 DE 2230794 A DE2230794 A DE 2230794A DE 2230794 C3 DE2230794 C3 DE 2230794C3
- Authority
- DE
- Germany
- Prior art keywords
- solvent
- monoester
- resin
- ionic
- diester
- 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
- 150000005690 diesters Chemical class 0.000 title claims description 35
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 17
- 235000011007 phosphoric acid Nutrition 0.000 title claims description 13
- 238000000926 separation method Methods 0.000 title description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- 239000003456 ion exchange resin Substances 0.000 claims description 10
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 10
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims 1
- 150000003014 phosphoric acid esters Chemical class 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 239000011347 resin Substances 0.000 description 23
- 229920005989 resin Polymers 0.000 description 23
- 235000019441 ethanol Nutrition 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000001174 ascending effect Effects 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- YZBOVSFWWNVKRJ-UHFFFAOYSA-M 2-butoxycarbonylbenzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1C([O-])=O YZBOVSFWWNVKRJ-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- BNMJSBUIDQYHIN-UHFFFAOYSA-N butyl dihydrogen phosphate Chemical compound CCCCOP(O)(O)=O BNMJSBUIDQYHIN-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000002031 ethanolic fraction Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000002044 hexane fraction Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- WRKCIHRWQZQBOL-UHFFFAOYSA-N octyl dihydrogen phosphate Chemical compound CCCCCCCCOP(O)(O)=O WRKCIHRWQZQBOL-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008961 swelling Effects 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
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
- C07F9/025—Purification; Separation; Stabilisation; Desodorisation of organo-phosphorus compounds
-
- 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
- C07F9/09—Esters of phosphoric acids
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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7125420A FR2145782A5 (https=) | 1971-07-12 | 1971-07-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2230794A1 DE2230794A1 (de) | 1973-01-18 |
| DE2230794B2 DE2230794B2 (https=) | 1973-12-13 |
| DE2230794C3 true DE2230794C3 (de) | 1974-07-25 |
Family
ID=9080223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722230794 Expired DE2230794C3 (de) | 1971-07-12 | 1972-06-23 | Verfahren zur Trennung von Orthophosphorsäuremono- und di'estern |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5536676B1 (https=) |
| BE (1) | BE786114A (https=) |
| CA (1) | CA977364A (https=) |
| DE (1) | DE2230794C3 (https=) |
| FR (1) | FR2145782A5 (https=) |
| GB (1) | GB1381534A (https=) |
| IT (1) | IT964459B (https=) |
| NL (1) | NL7209582A (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3046631A1 (de) * | 1980-12-11 | 1982-07-22 | Hoechst Ag, 6000 Frankfurt | Verfahren zur trennung eines phosphorsaeurealkylestergemisches durch extraktion |
-
1971
- 1971-07-12 FR FR7125420A patent/FR2145782A5/fr not_active Expired
-
1972
- 1972-06-23 DE DE19722230794 patent/DE2230794C3/de not_active Expired
- 1972-07-04 IT IT6914472A patent/IT964459B/it active
- 1972-07-10 GB GB3213672A patent/GB1381534A/en not_active Expired
- 1972-07-11 NL NL7209582A patent/NL7209582A/xx not_active Application Discontinuation
- 1972-07-11 CA CA146,878A patent/CA977364A/en not_active Expired
- 1972-07-11 BE BE786114A patent/BE786114A/xx unknown
- 1972-07-11 JP JP6873272A patent/JPS5536676B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA977364A (en) | 1975-11-04 |
| FR2145782A5 (https=) | 1973-02-23 |
| BE786114A (fr) | 1972-11-03 |
| DE2230794A1 (de) | 1973-01-18 |
| NL7209582A (https=) | 1973-01-16 |
| JPS5536676B1 (https=) | 1980-09-22 |
| DE2230794B2 (https=) | 1973-12-13 |
| GB1381534A (en) | 1975-01-22 |
| IT964459B (it) | 1974-01-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |