DD157463A5 - Verfahren zur umsetzung von alkoholen und/oder phenolen mit phosphorpentasulfid - Google Patents

Verfahren zur umsetzung von alkoholen und/oder phenolen mit phosphorpentasulfid Download PDF

Info

Publication number: DD157463A5
Authority: DD; German Democratic Republic
Prior art keywords: acid; phosphorus pentasulfide; yield; general formula; reaction
Prior art date: 1980-03-22

Application number

DD81228458A

Other languages

German (de)

English (en)

Inventor

Werner Krause

Juergen Grosse

Werner Klose

Original Assignee

Hoechst Ag

Priority date (The priority date 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 date listed.)

1980-03-22

Filing date

1981-03-19

Publication date

1982-11-10

1981-03-19 Application filed by Hoechst Ag filed Critical Hoechst Ag

1982-11-10 Publication of DD157463A5 publication Critical patent/DD157463A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 38
150000001298 alcohols Chemical class 0.000 title claims abstract description 11
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 title 1
239000002253 acid Substances 0.000 claims abstract description 74
238000006243 chemical reaction Methods 0.000 claims abstract description 42
239000003054 catalyst Substances 0.000 claims abstract description 37
150000002989 phenols Chemical class 0.000 claims abstract description 9
125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
125000003118 aryl group Chemical group 0.000 claims abstract description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
239000002184 metal Substances 0.000 claims abstract description 3
229910052751 metal Inorganic materials 0.000 claims abstract description 3
150000007522 mineralic acids Chemical class 0.000 claims abstract description 3
150000007524 organic acids Chemical class 0.000 claims abstract description 3
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
239000001301 oxygen Substances 0.000 claims abstract description 3
WSANLGASBHUYGD-UHFFFAOYSA-N sulfidophosphanium Chemical class S=[PH3] WSANLGASBHUYGD-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
239000011593 sulfur Substances 0.000 claims abstract description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 5
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
229910017604 nitric acid Inorganic materials 0.000 claims description 2
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 2
239000012433 hydrogen halide Substances 0.000 claims 1
229910000039 hydrogen halide Inorganic materials 0.000 claims 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract description 90
150000003863 ammonium salts Chemical class 0.000 abstract description 3
150000004714 phosphonium salts Chemical class 0.000 abstract description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
229910052757 nitrogen Inorganic materials 0.000 description 12
150000007513 acids Chemical class 0.000 description 9
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 8
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 8
239000002002 slurry Substances 0.000 description 8
229960004592 isopropanol Drugs 0.000 description 7
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 6
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
230000009257 reactivity Effects 0.000 description 6
238000003756 stirring Methods 0.000 description 6
RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 6
238000004821 distillation Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
238000006136 alcoholysis reaction Methods 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
238000000746 purification Methods 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000000126 substance Substances 0.000 description 3
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
238000004140 cleaning Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
LYVQWBGUSKLGLM-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO.CCCCCCCCCCCCO LYVQWBGUSKLGLM-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
MGTZOBYVRMIWNK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO MGTZOBYVRMIWNK-UHFFFAOYSA-N 0.000 description 2
ATKIGFUAOXHQMV-UHFFFAOYSA-N octan-1-ol Chemical compound CCCCCCCCO.CCCCCCCCO ATKIGFUAOXHQMV-UHFFFAOYSA-N 0.000 description 2
FTDXCHCAMNRNNY-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1 FTDXCHCAMNRNNY-UHFFFAOYSA-N 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000010517 secondary reaction Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000007711 solidification Methods 0.000 description 2
230000008023 solidification Effects 0.000 description 2
OXIKLRTYAYRAOE-CMDGGOBGSA-N (e)-3-(1-benzyl-3-pyridin-3-ylpyrazol-4-yl)prop-2-enoic acid Chemical compound N1=C(C=2C=NC=CC=2)C(/C=C/C(=O)O)=CN1CC1=CC=CC=C1 OXIKLRTYAYRAOE-CMDGGOBGSA-N 0.000 description 1
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
QAPFPOOLEMZROC-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO.CCCCC(CC)CO QAPFPOOLEMZROC-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
206010011469 Crying Diseases 0.000 description 1
OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000004455 differential thermal analysis Methods 0.000 description 1
LRMLWYXJORUTBG-UHFFFAOYSA-N dimethylphosphorylmethane Chemical compound CP(C)(C)=O LRMLWYXJORUTBG-UHFFFAOYSA-N 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
-1 dithiophosphoric acid diesters Chemical class 0.000 description 1
QNALZNMQKPAXNA-UHFFFAOYSA-M dodecyl(trimethyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCC[P+](C)(C)C QNALZNMQKPAXNA-UHFFFAOYSA-M 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
TUDUDQJRUPFUMA-UHFFFAOYSA-M ethyl(trioctyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCC[P+](CC)(CCCCCCCC)CCCCCCCC TUDUDQJRUPFUMA-UHFFFAOYSA-M 0.000 description 1
238000005188 flotation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
GQHMIIJVTOFEIM-UHFFFAOYSA-N hydroxy-octylperoxy-phenylsulfanyl-sulfanylidene-lambda5-phosphane Chemical compound C(CCCCCCC)OOP(SC1=CC=CC=C1)(O)=S GQHMIIJVTOFEIM-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
210000003141 lower extremity Anatomy 0.000 description 1
239000003879 lubricant additive Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 1
229910017464 nitrogen compound Inorganic materials 0.000 description 1
150000002830 nitrogen compounds Chemical class 0.000 description 1
AFIOSAZNYSKVIC-UHFFFAOYSA-N octan-1-ol;phenol Chemical compound OC1=CC=CC=C1.CCCCCCCCO AFIOSAZNYSKVIC-UHFFFAOYSA-N 0.000 description 1
PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
SIPZWDFRFRNPRN-UHFFFAOYSA-M sodium;dimethyl-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Na+].CP(C)([S-])=S SIPZWDFRFRNPRN-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
AXTXARBFPWQUQA-UHFFFAOYSA-M tetraoctylphosphanium;chloride Chemical compound [Cl-].CCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CCCCCCCC AXTXARBFPWQUQA-UHFFFAOYSA-M 0.000 description 1
KTFAZNVGJUIWJM-UHFFFAOYSA-N trimethyl(sulfanylidene)-$l^{5}-phosphane Chemical compound CP(C)(C)=S KTFAZNVGJUIWJM-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/17—Esters of thiophosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
- 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
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds

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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD81228458A 1980-03-22 1981-03-19 Verfahren zur umsetzung von alkoholen und/oder phenolen mit phosphorpentasulfid DD157463A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19803011085 DE3011085A1 (de)	1980-03-22	1980-03-22	Verfahren zur umsetzung von alkoholen und/oder phenolen mit phosphorpentasulfid

Publications (1)

Publication Number	Publication Date
DD157463A5 true DD157463A5 (de)	1982-11-10

Family

ID=6097984

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD81228458A DD157463A5 (de)	1980-03-22	1981-03-19	Verfahren zur umsetzung von alkoholen und/oder phenolen mit phosphorpentasulfid

Country Status (7)

Country	Link
US (1)	US4397791A (da)
EP (1)	EP0036485B1 (da)
JP (1)	JPS56145296A (da)
CA (1)	CA1156667A (da)
DD (1)	DD157463A5 (da)
DE (2)	DE3011085A1 (da)
DK (1)	DK166086C (da)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5178782A (en) *	1985-03-12	1993-01-12	The Lubrizol Corporation	Metal salts of mixed aromatic/aliphatic phosphorodithioic acids
CA1271777A (en) *	1985-04-29	1990-07-17	The Lubrizol Corporation	Metal salts of mixed aromatic/aliphatic phosphorodithioic acids
US5001249A (en) *	1987-03-30	1991-03-19	Ici Americas Inc.	Catalytic process for preparing dialkyl phosphorodithioic acids
US7368596B2 (en)	2003-11-06	2008-05-06	Afton Chemical Corporation	Process for producing zinc dialkyldithiophosphates exhibiting improved seal compatibility properties
DE102006061536A1 (de) *	2006-12-27	2008-07-03	Bayer Materialscience Ag	Verfahren zur Konditionierung von Isocyanaten
EP2125839A4 (en) *	2007-01-31	2012-05-02	Vanderbilt Co R T	DITHIOPHOSPHATE COMPOSITION AND USE OF RUBBER
CN113372381A (zh) *	2021-05-13	2021-09-10	西北矿冶研究院	烃基二硫代磷酸硫醚酯的合成方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1228528A (da) *	1968-04-10	1971-04-15
FR2187799B1 (da) *	1972-06-07	1974-07-26	Ugine Kuhlmann
US4083899A (en) *	1972-06-07	1978-04-11	Produits Chimiques Ugine Kuhlmann	Accelerated process of alcoholysis or phenolysis of phosporus pentasulfide
US4116871A (en) *	1977-06-29	1978-09-26	Chevron Research Company	Preparation of phosphorus-containing acids and salts
DE2828721A1 (de)	1978-06-30	1980-01-10	Ceag Licht & Strom	Ausgangsuebertrager fuer wechselrichter

1980
- 1980-03-22 DE DE19803011085 patent/DE3011085A1/de not_active Withdrawn
1981
- 1981-02-17 DE DE8181101094T patent/DE3160145D1/de not_active Expired
- 1981-02-17 EP EP81101094A patent/EP0036485B1/de not_active Expired
- 1981-03-02 CA CA000372042A patent/CA1156667A/en not_active Expired
- 1981-03-13 US US06/243,613 patent/US4397791A/en not_active Expired - Lifetime
- 1981-03-19 DD DD81228458A patent/DD157463A5/de unknown
- 1981-03-20 JP JP3969181A patent/JPS56145296A/ja active Granted
- 1981-03-20 DK DK126281A patent/DK166086C/da active

Also Published As

Publication number	Publication date
DK166086B (da)	1993-03-08
EP0036485B1 (de)	1983-04-06
DK126281A (da)	1981-09-23
CA1156667A (en)	1983-11-08
DE3160145D1 (en)	1983-05-11
JPS6411030B2 (da)	1989-02-23
EP0036485A1 (de)	1981-09-30
DE3011085A1 (de)	1981-10-01
DK166086C (da)	1993-08-23
US4397791A (en)	1983-08-09
JPS56145296A (en)	1981-11-11

Publication	Publication Date	Title
DE3445553A1 (de)	1985-07-04	Verbessertes verfahren zur herstellung von aromatischen carbonaten
DD157463A5 (de)	1982-11-10	Verfahren zur umsetzung von alkoholen und/oder phenolen mit phosphorpentasulfid
DE1815999C3 (de)	1978-06-08	B-Chloräthanpyrophosphonsäure und ihre Verwendung als Pflanzenwachstumshormon
EP0150739B1 (de)	1989-03-08	Verfahren zur Herstellung alkanphosphoniger Säuren
DE69821307T2 (de)	2004-11-18	Verfahren zur Herstellung von Polysulfidsilanen
DE2636270C2 (de)	1983-06-09	Verfahren zur Herstellung von Phosphorigsäureesterchloriden und Phosphonigsäureesterchloriden
EP0090213A1 (de)	1983-10-05	Verfahren zur Herstellung von Derivaten der Vinylphosphon- oder Vinylpyrophosphonsäure
DE3541603C2 (de)	1994-05-11	Verfahren zur Herstellung von Diorganomonothiophosphinaten
EP0008366A1 (de)	1980-03-05	Verfahren zur Herstellung neutraler Phosphorsäureester nach dem Phasengrenzflächenverfahren und nach diesem Verfahren hergestellte Verbindungen
EP0130439B1 (de)	1987-04-15	Verfahren zur Herstellung von Derivaten der Vinylphosphon-, oder Vinylpyrophosphonsäure
DE3779772T2 (de)	1993-02-11	Verfahren zur herstellung von 0,0-di-niedrig-alkyl-chlorothiophosphaten.
DD139716A5 (de)	1980-01-16	Verfahren zur herstellung von dialkyl-phosphorchloridothionaten
DE2527650B2 (de)	1981-04-23	Verfahren zur Herstellung von Phenylthiophosphonyl-dichlorid
EP0085347A1 (de)	1983-08-10	Herstellung von Dialkylcarbonaten
DD206363A1 (de)	1984-01-25	Verfahren zur herstellung reiner phosphoriger saeure
DE2601532A1 (de)	1976-08-05	Verfahren zur herstellung von o,o-dialkyl-s-benzyl-thiophosphaten
DD228722A1 (de)	1985-10-23	Herstellung von gemischen aus bis(dialkoxythiophosphoryl)sulfanen
DE1543883C (de)	1971-09-16	Verfahren zur Herstellung von 1,3,2 Benzodioxaphosphoran 2 thionen
DE2354601C3 (de)	1984-08-02	Verfahren zur Herstellung von Chlorthiophosphorsäuredialkylestern
DE1939469C3 (de)	1978-09-14	Verfahren zur Herstellung von Thiophenolen
CH629501A5 (de)	1982-04-30	Verfahren zur herstellung von 2-dialkoxyphosphinylimino-1,3-dithietanen.
DE3238910A1 (de)	1984-04-26	Verfahren zur herstellung von 1-hydroxyalkan-1-phosphonsaeuren
CH633295A5 (de)	1982-11-30	Verfahren zur herstellung von 2-dialkoxyphosphinylimino-1,3-dithietanen.
DE1198374B (de)	1965-08-12	Verfahren zur Herstellung von Thionophosphor-saeure-O-phenyl-O, O-dialkylestern mit niederen Alkylgruppen
DE2134019A1 (de)	1973-01-25	Substituierte phosphazophosphonylverbindungen