CN1493575A - Method of preparing phosphite ester - Google Patents
Method of preparing phosphite ester Download PDFInfo
- Publication number
- CN1493575A CN1493575A CNA021466076A CN02146607A CN1493575A CN 1493575 A CN1493575 A CN 1493575A CN A021466076 A CNA021466076 A CN A021466076A CN 02146607 A CN02146607 A CN 02146607A CN 1493575 A CN1493575 A CN 1493575A
- Authority
- CN
- China
- Prior art keywords
- acid ester
- ammonium
- phosphorous acid
- salt
- phosphoric acid
- 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 description 21
- 150000008301 phosphite esters Chemical class 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims abstract description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 9
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 235000019270 ammonium chloride Nutrition 0.000 claims abstract description 5
- WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 claims abstract description 5
- -1 phosphorous acid ester Chemical class 0.000 claims description 38
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 27
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 23
- 239000011259 mixed solution Substances 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 238000005886 esterification reaction Methods 0.000 claims description 16
- JDRJCBXXDRYVJC-UHFFFAOYSA-N OP(O)O.N.N.N Chemical compound OP(O)O.N.N.N JDRJCBXXDRYVJC-UHFFFAOYSA-N 0.000 claims description 10
- 239000012043 crude product Substances 0.000 claims description 8
- 230000032050 esterification Effects 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 abstract description 8
- 238000001816 cooling Methods 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 abstract description 5
- FNDXFUBHPXBGMD-UHFFFAOYSA-N OP(O)O.OP(O)(O)=O Chemical compound OP(O)O.OP(O)(O)=O FNDXFUBHPXBGMD-UHFFFAOYSA-N 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 17
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 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 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 238000012797 qualification Methods 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000021050 feed intake Nutrition 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003987 organophosphate pesticide Substances 0.000 description 1
- CDXVUROVRIFQMV-UHFFFAOYSA-N oxo(diphenoxy)phosphanium Chemical compound C=1C=CC=CC=1O[P+](=O)OC1=CC=CC=C1 CDXVUROVRIFQMV-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 02146607 CN1212326C (en) | 2002-10-28 | 2002-10-28 | Method of preparing phosphite ester |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 02146607 CN1212326C (en) | 2002-10-28 | 2002-10-28 | Method of preparing phosphite ester |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1493575A true CN1493575A (en) | 2004-05-05 |
CN1212326C CN1212326C (en) | 2005-07-27 |
Family
ID=34232805
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 02146607 Expired - Lifetime CN1212326C (en) | 2002-10-28 | 2002-10-28 | Method of preparing phosphite ester |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1212326C (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100374450C (en) * | 2006-07-21 | 2008-03-12 | 申厚宝 | Triethyl phosphite production process |
CN100376589C (en) * | 2006-07-21 | 2008-03-26 | 申厚宝 | Trimethyl phosphite production process |
CN101775033B (en) * | 2010-01-19 | 2012-08-29 | 青岛大学 | Preparation method of phosphite ester by using dividing wall tower reaction rectification technique |
CN103224529A (en) * | 2013-04-09 | 2013-07-31 | 天津市联瑞阻燃材料有限公司 | Preparation method of triphenyl phosphite |
CN103801400A (en) * | 2014-03-07 | 2014-05-21 | 中国天辰工程有限公司 | Process for synthesizing mono-phosphite metal coordination catalyst by coupling reactive distillation and magnetically-stabilized bed |
-
2002
- 2002-10-28 CN CN 02146607 patent/CN1212326C/en not_active Expired - Lifetime
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100374450C (en) * | 2006-07-21 | 2008-03-12 | 申厚宝 | Triethyl phosphite production process |
CN100376589C (en) * | 2006-07-21 | 2008-03-26 | 申厚宝 | Trimethyl phosphite production process |
CN101775033B (en) * | 2010-01-19 | 2012-08-29 | 青岛大学 | Preparation method of phosphite ester by using dividing wall tower reaction rectification technique |
CN103224529A (en) * | 2013-04-09 | 2013-07-31 | 天津市联瑞阻燃材料有限公司 | Preparation method of triphenyl phosphite |
CN103801400A (en) * | 2014-03-07 | 2014-05-21 | 中国天辰工程有限公司 | Process for synthesizing mono-phosphite metal coordination catalyst by coupling reactive distillation and magnetically-stabilized bed |
CN103801400B (en) * | 2014-03-07 | 2015-12-02 | 中国天辰工程有限公司 | A kind of reactive distillation synthesizes the technique of single phosphite ester Metal complex catalysts with magnetic stablizing bed coupling |
Also Published As
Publication number | Publication date |
---|---|
CN1212326C (en) | 2005-07-27 |
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Legal Events
Date | Code | Title | Description |
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C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: SICHUAN LESHAN FUHUA AGRICULTURAL SCIENCE INVESTM Free format text: FORMER OWNER: LIU DELIANG Effective date: 20070803 |
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C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20070803 Address after: Wutongqiao District Qiao Gou Zhen 614800 Sichuan city of Leshan Province Patentee after: Sichuan Leshan Fuhua Agricultural Science Investment Group Co.,Ltd. Address before: 052260, Hebei City, Jinzhou Province North Little Village White Secretary Patentee before: Liu Deliang |
|
ASS | Succession or assignment of patent right |
Owner name: FUHUA TONGDA PESTICIDE SCIENCE AND TECHNOLOGY CO. Free format text: FORMER OWNER: SICHUAN LESHAN FUHUA AGRICULTURAL SCIENCE INVESTMENT GROUP CO., LTD. Effective date: 20080822 |
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C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20080822 Address after: Wutongqiao District Bridge Town Sichuan city of Leshan Province Patentee after: Sichuan Leshan Fuhua Tongda Pesticide Technology Co.,Ltd. Address before: Wutongqiao District Bridge Town Sichuan city of Leshan Province Patentee before: Sichuan Leshan Fuhua Agricultural Science Investment Group Co.,Ltd. |
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CX01 | Expiry of patent term |
Granted publication date: 20050727 |
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CX01 | Expiry of patent term |