CS202090B2 - Method of producing organo silicon compounds containing sulphur and phophorus - Google Patents

Method of producing organo silicon compounds containing sulphur and phophorus Download PDF

Info

Publication number: CS202090B2
Authority: CS; Czechoslovakia
Prior art keywords: acid; phenyl; formula; rubber; carbon atoms
Prior art date: 1976-12-23

Application number

CS778709A

Other languages

Czech (cs)

English (en)

Inventor

Hans-Dieter Pletka

Gerd Zezulka

Original Assignee

Degussa

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.)

1976-12-23

Filing date

1977-12-22

Publication date

1980-12-31

1977-12-22 Application filed by Degussa filed Critical Degussa

1980-12-31 Publication of CS202090B2 publication Critical patent/CS202090B2/cs

Links

150000003961 organosilicon compounds Chemical class 0.000 title claims description 6
238000000034 method Methods 0.000 title claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title description 6
239000005864 Sulphur Substances 0.000 title 1
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims abstract 2
-1 phosphorus halide Chemical class 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 5
239000012433 hydrogen halide Substances 0.000 claims description 3
229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
229910052698 phosphorus Inorganic materials 0.000 claims description 3
239000011574 phosphorus Substances 0.000 claims description 3
TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
QCJQWJKKTGJDCM-UHFFFAOYSA-N [P].[S] Chemical compound [P].[S] QCJQWJKKTGJDCM-UHFFFAOYSA-N 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
ZHCAAFJSYLFLPX-UHFFFAOYSA-N nitrocyclohexatriene Chemical group [O-][N+](=O)C1=CC=C=C[CH]1 ZHCAAFJSYLFLPX-UHFFFAOYSA-N 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
229920001971 elastomer Polymers 0.000 abstract description 29
239000000203 mixture Substances 0.000 abstract description 29
239000005060 rubber Substances 0.000 abstract description 29
150000001875 compounds Chemical class 0.000 abstract description 15
239000000945 filler Substances 0.000 abstract description 12
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 abstract description 4
239000006229 carbon black Substances 0.000 abstract description 3
125000002947 alkylene group Chemical group 0.000 abstract description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 abstract 1
239000012744 reinforcing agent Substances 0.000 abstract 1
239000002253 acid Substances 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
229910052717 sulfur Inorganic materials 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 8
WVPKAWVFTPWPDB-UHFFFAOYSA-N dichlorophosphinic acid Chemical compound OP(Cl)(Cl)=O WVPKAWVFTPWPDB-UHFFFAOYSA-N 0.000 description 7
238000000921 elemental analysis Methods 0.000 description 7
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
229910000077 silane Inorganic materials 0.000 description 6
239000002904 solvent Substances 0.000 description 6
150000002148 esters Chemical class 0.000 description 5
150000004760 silicates Chemical class 0.000 description 5
229910052710 silicon Inorganic materials 0.000 description 5
239000010703 silicon Substances 0.000 description 5
239000011593 sulfur Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
235000012239 silicon dioxide Nutrition 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000370 acceptor Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229920003052 natural elastomer Polymers 0.000 description 3
229920001194 natural rubber Polymers 0.000 description 3
150000004756 silanes Chemical class 0.000 description 3
238000004073 vulcanization Methods 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
101001022148 Homo sapiens Furin Proteins 0.000 description 2
101000701936 Homo sapiens Signal peptidase complex subunit 1 Proteins 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
102100030313 Signal peptidase complex subunit 1 Human genes 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000011521 glass Substances 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
QLFFCLRSMTUBEZ-UHFFFAOYSA-N phosphoric acid;sodium Chemical compound [Na].[Na].OP(O)(O)=O QLFFCLRSMTUBEZ-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
239000010453 quartz Substances 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000008117 stearic acid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
229920003051 synthetic elastomer Polymers 0.000 description 2
239000005061 synthetic rubber Substances 0.000 description 2
239000011787 zinc oxide Substances 0.000 description 2
FHYZZROHOBOTES-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5-(2,3,4,5-tetrachlorophenyl)sulfanylbenzene Chemical compound ClC1=C(Cl)C(Cl)=CC(SC=2C(=C(Cl)C(Cl)=C(Cl)C=2)Cl)=C1Cl FHYZZROHOBOTES-UHFFFAOYSA-N 0.000 description 1
OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
NVJUHMXYKCUMQA-UHFFFAOYSA-N 1-ethoxypropane Chemical compound CCCOCC NVJUHMXYKCUMQA-UHFFFAOYSA-N 0.000 description 1
125000004806 1-methylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
125000004809 1-methylpropylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])[*:2] 0.000 description 1
GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical group CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 1
YLZYSVYZMDJYOT-UHFFFAOYSA-N 2-methoxypyrimidine Chemical compound COC1=NC=CC=N1 YLZYSVYZMDJYOT-UHFFFAOYSA-N 0.000 description 1
125000004807 2-methylethylene group Chemical group [H]C([H])([H])C([H])([*:2])C([H])([H])[*:1] 0.000 description 1
125000004810 2-methylpropylene group Chemical group [H]C([H])([H])C([H])(C([H])([H])[*:2])C([H])([H])[*:1] 0.000 description 1
VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
IDWYWYMYFZSZEE-UHFFFAOYSA-N 3-ethylsulfanylpropane-1-thiol Chemical compound CCSCCCS IDWYWYMYFZSZEE-UHFFFAOYSA-N 0.000 description 1
UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
239000004604 Blowing Agent Substances 0.000 description 1
229910001369 Brass Inorganic materials 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
MQHMYPUFYARQMN-UHFFFAOYSA-N ClOP(=O)OCl Chemical compound ClOP(=O)OCl MQHMYPUFYARQMN-UHFFFAOYSA-N 0.000 description 1
GEFGGQVURBPVSA-UHFFFAOYSA-N ClP(Cl)(Cl)Cl Chemical compound ClP(Cl)(Cl)Cl GEFGGQVURBPVSA-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
244000043261 Hevea brasiliensis Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
101100386510 Mus musculus Dazap2 gene Proteins 0.000 description 1
101100498930 Mus musculus Degs1 gene Proteins 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
OFSMWILHURPCLG-UHFFFAOYSA-N OC(C(S(C=C1Cl)(Cl)(Cl)Cl)=C1Cl)=O Chemical compound OC(C(S(C=C1Cl)(Cl)(Cl)Cl)=C1Cl)=O OFSMWILHURPCLG-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004115 Sodium Silicate Substances 0.000 description 1
239000004902 Softening Agent Substances 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
102000036435 Zincins Human genes 0.000 description 1
108091007139 Zincins Proteins 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000012190 activator Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000002318 adhesion promoter Substances 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
230000003712 anti-aging effect Effects 0.000 description 1
230000002929 anti-fatigue Effects 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000010425 asbestos Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000010951 brass Substances 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
ZSCCOCBYYJPSBX-UHFFFAOYSA-N bromo-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(Br)=S ZSCCOCBYYJPSBX-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 0.000 description 1
HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 description 1
238000013016 damping Methods 0.000 description 1
CQLVUNOSFSDETA-UHFFFAOYSA-N dibromo-(4-nitrophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound [O-][N+](=O)C1=CC=C(OP(Br)(Br)=S)C=C1 CQLVUNOSFSDETA-UHFFFAOYSA-N 0.000 description 1
RJALBHUNPRJDIE-UHFFFAOYSA-N dichloro-(4-nitrophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound [O-][N+](=O)C1=CC=C(OP(Cl)(Cl)=S)C=C1 RJALBHUNPRJDIE-UHFFFAOYSA-N 0.000 description 1
OOFVSLAKBNBEEH-UHFFFAOYSA-N dichloro-hydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(Cl)(Cl)=S OOFVSLAKBNBEEH-UHFFFAOYSA-N 0.000 description 1
ODPZLWXUWFTSEA-UHFFFAOYSA-N dichloro-phenoxy-sulfanylidene-$l^{5}-phosphane Chemical compound ClP(Cl)(=S)OC1=CC=CC=C1 ODPZLWXUWFTSEA-UHFFFAOYSA-N 0.000 description 1
TXFOLHZMICYNRM-UHFFFAOYSA-N dichlorophosphoryloxybenzene Chemical compound ClP(Cl)(=O)OC1=CC=CC=C1 TXFOLHZMICYNRM-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
QVKQJEWZVQFGIY-UHFFFAOYSA-N dipropyl hydrogen phosphate Chemical compound CCCOP(O)(=O)OCCC QVKQJEWZVQFGIY-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 0.000 description 1
238000010891 electric arc Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
VDTIMXCBOXBHER-UHFFFAOYSA-N hydroxy-bis(sulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound OP(S)(S)=S VDTIMXCBOXBHER-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
229910000464 lead oxide Inorganic materials 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
208000024714 major depressive disease Diseases 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
238000003801 milling Methods 0.000 description 1
230000000051 modifying effect Effects 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052756 noble gas Inorganic materials 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
OTYNBGDFCPCPOU-UHFFFAOYSA-N phosphane sulfane Chemical compound S.P[H] OTYNBGDFCPCPOU-UHFFFAOYSA-N 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
239000000049 pigment Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000012758 reinforcing additive Substances 0.000 description 1
230000003014 reinforcing effect Effects 0.000 description 1
239000012779 reinforcing material Substances 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
238000007789 sealing Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
125000005624 silicic acid group Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
229910052911 sodium silicate Inorganic materials 0.000 description 1
HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical group [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910001928 zirconium oxide Inorganic materials 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/1411—Esters of phosphorous acids with hydroxyalkyl compounds with 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
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/548—Silicon-containing compounds containing sulfur
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes

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)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Compositions Of Macromolecular Compounds (AREA)

CS778709A 1976-12-23 1977-12-22 Method of producing organo silicon compounds containing sulphur and phophorus CS202090B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2658368A DE2658368C2 (de)	1976-12-23	1976-12-23	Schwefel und Phosphor enthaltende Organosiliciumverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung

Publications (1)

Publication Number	Publication Date
CS202090B2 true CS202090B2 (en)	1980-12-31

Family

ID=5996356

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS778709A CS202090B2 (en)	1976-12-23	1977-12-22	Method of producing organo silicon compounds containing sulphur and phophorus

Country Status (10)

Country	Link
US (2)	US4152347A (pl)
JP (1)	JPS5379823A (pl)
BE (1)	BE862222A (pl)
BR (1)	BR7708476A (pl)
CS (1)	CS202090B2 (pl)
DD (1)	DD135494A5 (pl)
DE (1)	DE2658368C2 (pl)
FR (1)	FR2375243A1 (pl)
GB (1)	GB1581079A (pl)
NL (1)	NL7713152A (pl)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5796048A (en) *	1980-12-05	1982-06-15	Fujikura Ltd	Low-temperature curing (vulcanizing) method of halogen-containing polymer and crosslinkable halogen-containing polymeric composition used therefor
EP0537006A3 (en) *	1991-10-10	1993-06-16	Elastochem, Inc.	Fluxed composites
CA2194638A1 (en) *	1996-03-06	1997-09-06	Giorgio Agostini	Asymmetrical siloxy compounds
US5750197A (en)	1997-01-09	1998-05-12	The University Of Cincinnati	Method of preventing corrosion of metals using silanes
ATE239737T1 (de) *	1997-08-21	2003-05-15	Crompton Corp	Blockierte merkaptosilane als kupplungsmittel für gefüllte kautschukzusammensetzung
US6162547A (en) *	1998-06-24	2000-12-19	The University Of Cinncinnati	Corrosion prevention of metals using bis-functional polysulfur silanes
US6416869B1 (en) *	1999-07-19	2002-07-09	University Of Cincinnati	Silane coatings for bonding rubber to metals
US6827981B2 (en)	1999-07-19	2004-12-07	The University Of Cincinnati	Silane coatings for metal
DE19954815C1 (de) *	1999-11-13	2001-06-07	Degussa	Verfahren zur Herstellung von schwefel- und phosphorhaltigen Organosiliziumverbindungen
US6441070B1 (en) *	2000-07-14	2002-08-27	The Goodyear Tire & Rubber Company	Rubber compositions containing a trivalent phosphorous compound-silica complex
DE10122269A1 (de) *	2001-05-08	2002-11-21	Degussa	Silanmodifizierter biopolymerer, biooligomerer, oxidischer oder silikatischer Füllstoff, Verfahren zu seiner Herstellung und seine Verwendung
US7301042B2 (en) *	2002-04-23	2007-11-27	Cruse Richard W	Blocked mercaptosilane hydrolyzates as coupling agents for mineral-filled elastomer compositions
AU2003249019A1 (en) *	2002-07-09	2004-01-23	Momentive Performance Materials Inc.	Silica-rubber mixtures having improved hardness
CN100341881C (zh) *	2002-11-04	2007-10-10	通用电气公司	封端巯基硅烷偶合剂的制备方法
DE10354616A1 (de)	2003-11-21	2005-06-23	Degussa Ag	Kautschukmischungen
US20050245753A1 (en) *	2004-05-03	2005-11-03	Cruse Richard W	Cyclic diol-derived blocked mercaptofunctional silane compositions
US7531588B2 (en) *	2004-07-30	2009-05-12	Momentive Performance Materials Inc.	Silane compositions, processes for their preparation and rubber compositions containing same
US7928258B2 (en) *	2004-08-20	2011-04-19	Momentive Performance Materials Inc.	Cyclic diol-derived blocked mercaptofunctional silane compositions
US7510670B2 (en) *	2006-02-21	2009-03-31	Momentive Performance Materials Inc.	Free flowing filler composition based on organofunctional silane
US7919650B2 (en) *	2006-02-21	2011-04-05	Momentive Performance Materials Inc.	Organofunctional silanes and their mixtures
US7504456B2 (en) *	2006-02-21	2009-03-17	Momentive Performance Materials Inc.	Rubber composition containing organofunctional silane
US7718819B2 (en) *	2006-02-21	2010-05-18	Momentive Performance Materials Inc.	Process for making organofunctional silanes and mixtures thereof
US8008519B2 (en)	2006-08-14	2011-08-30	Momentive Performance Materials Inc.	Process for making mercapto-functional silane
US8097744B2 (en) *	2006-08-14	2012-01-17	Momentive Performance Materials Inc.	Free flowing filler composition comprising mercapto-functional silane
US7550540B2 (en) *	2006-08-14	2009-06-23	Momentive Performance Materials Inc.	Rubber composition and articles therefrom both comprising mercapto-functional silane
US7368584B2 (en) *	2006-08-14	2008-05-06	Momentive Performance Materials Inc.	Mercapto-functional silane
US7737202B2 (en) *	2006-12-28	2010-06-15	Momentive Performance Materials Inc.	Free-flowing filler composition and rubber composition containing same
US7968636B2 (en) *	2006-12-28	2011-06-28	Continental Ag	Tire compositions and components containing silated cyclic core polysulfides
US7960460B2 (en) *	2006-12-28	2011-06-14	Momentive Performance Materials, Inc.	Free-flowing filler composition and rubber composition containing same
US7696269B2 (en)	2006-12-28	2010-04-13	Momentive Performance Materials Inc.	Silated core polysulfides, their preparation and use in filled elastomer compositions
US7968635B2 (en) *	2006-12-28	2011-06-28	Continental Ag	Tire compositions and components containing free-flowing filler compositions
US8592506B2 (en) *	2006-12-28	2013-11-26	Continental Ag	Tire compositions and components containing blocked mercaptosilane coupling agent
US7968634B2 (en) *	2006-12-28	2011-06-28	Continental Ag	Tire compositions and components containing silated core polysulfides
US7968633B2 (en)	2006-12-28	2011-06-28	Continental Ag	Tire compositions and components containing free-flowing filler compositions
US7687558B2 (en) *	2006-12-28	2010-03-30	Momentive Performance Materials Inc.	Silated cyclic core polysulfides, their preparation and use in filled elastomer compositions
US7781606B2 (en) *	2006-12-28	2010-08-24	Momentive Performance Materials Inc.	Blocked mercaptosilane coupling agents, process for making and uses in rubber
US7816435B2 (en) *	2007-10-31	2010-10-19	Momentive Performance Materials Inc.	Halo-functional silane, process for its preparation, rubber composition containing same and articles manufactured therefrom
US20240141146A1 (en) *	2022-10-26	2024-05-02	Samuel H. Creelan	Biodegradable tire and tire composition

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1254590B (de)	1965-01-29	1967-11-23	Siemens Ag	Verfahren zum tiegelfreien Zonenschmelzen von Halbleitermaterial, insbesondere von Silicium
GB1189441A (en) *	1966-03-21	1970-04-29	Albright & Wilson Mfg Ltd	Organic Compositions containing Oxidation Retarders
US3697474A (en) *	1969-10-30	1972-10-10	Freeport Sulphur Co	Organo-clay-polymer compositions
US3978103A (en) *	1971-08-17	1976-08-31	Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler	Sulfur containing organosilicon compounds
BE790735A (fr) *	1971-11-03	1973-02-15	Dynamit Nobel Ag	Application de phosphoro-organosilanes comme promoteurs d'adhesion
SU580840A3 (ru) *	1974-02-07	1977-11-15	Дегусса (Фирма)	Способ получени серосодержащих кремнийорганических соединений
US3949140A (en) *	1974-05-06	1976-04-06	Owens-Corning Fiberglas Corporation	Organo silicon derivatives coated on glass fibers
US4044037A (en) *	1974-12-24	1977-08-23	Union Carbide Corporation	Sulfur containing silane coupling agents

1976
- 1976-12-23 DE DE2658368A patent/DE2658368C2/de not_active Expired
1977
- 1977-11-29 NL NL7713152A patent/NL7713152A/xx not_active Application Discontinuation
- 1977-12-02 GB GB50306/77A patent/GB1581079A/en not_active Expired
- 1977-12-12 US US05/859,968 patent/US4152347A/en not_active Expired - Lifetime
- 1977-12-20 BR BR7708476A patent/BR7708476A/pt unknown
- 1977-12-20 DD DD77202809A patent/DD135494A5/xx unknown
- 1977-12-20 FR FR7738391A patent/FR2375243A1/fr active Granted
- 1977-12-22 BE BE6046283A patent/BE862222A/xx not_active IP Right Cessation
- 1977-12-22 CS CS778709A patent/CS202090B2/cs unknown
- 1977-12-23 JP JP15549777A patent/JPS5379823A/ja active Granted
1978
- 1978-12-08 US US05/967,577 patent/US4222930A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
JPS6115877B2 (pl)	1986-04-26
JPS5379823A (en)	1978-07-14
US4152347A (en)	1979-05-01
GB1581079A (en)	1980-12-10
DD135494A5 (de)	1979-05-09
US4222930A (en)	1980-09-16
FR2375243B1 (pl)	1980-09-19
BE862222A (fr)	1978-06-22
FR2375243A1 (fr)	1978-07-21
NL7713152A (nl)	1978-06-27
DE2658368A1 (de)	1978-07-06
BR7708476A (pt)	1978-08-08
DE2658368C2 (de)	1982-09-23

Publication	Publication Date	Title
CS202090B2 (en)	1980-12-31	Method of producing organo silicon compounds containing sulphur and phophorus
US2768193A (en)	1956-10-23	Organosilicon compounds containing phosphorus
US3853935A (en)	1974-12-10	Aralkyl silanes substituted in the nucleus
JP2001348394A (ja)	2001-12-18	オルガノ珪素化合物、その製造方法、その使用、およびオルガノ珪素化合物を含有するゴム混合物
US5210260A (en)	1993-05-11	Process for obtaining bis(2,4-di-tert-butylphenyl) halophosphites
CN111433287A (zh)	2020-07-17	硅烷混合物及其制备方法
KR102728622B1 (ko)	2024-11-12	실란 혼합물 및 그의 제조 방법
CN102822183A (zh)	2012-12-12	制备含硅的偶氮二甲酰胺的方法
JP7268025B2 (ja)	2023-05-02	シラン混合物およびその製造方法
KR101803591B1 (ko)	2017-11-30	실릴기로 보호된 2급 아미노기를 갖는 오르가녹시실란 화합물 및 그의 제조 방법
US2934564A (en)	1960-04-26	Organohalophosphines
CN111386315B (zh)	2023-01-10	硅烷混合物及其制备方法
US4032602A (en)	1977-06-28	Process for the production of phosphite chlorides
JPS6024114B2 (ja)	1985-06-11	オルガノシクロテトラシロキサン
US2482063A (en)	1949-09-13	Preparation of organic phosphates
US4079103A (en)	1978-03-14	Process for the production of phosphite chlorides
US3642960A (en)	1972-02-15	Method of producing thiono- or dithio-phosphonic acid esters
US5648549A (en)	1997-07-15	Process for the preparation of secondary arylphosphines
Bockholt et al.	2009	Neutral and Cationic Silicon Species Containing Aryl‐OCO‐or Aryl‐SCS‐Type Pincer Ligands: Synthesis, Structure, Bonding, and Comparison with Aryl‐NCN Systems
US4290978A (en)	1981-09-22	Production of phosphoro chloride thiolates
US3031489A (en)	1962-04-24	Halophosphorus compounds and a method for making them
US2615043A (en)	1952-10-21	Method of preparing ethyl dichlorophosphine
US3928463A (en)	1975-12-23	Process for the preparation of tertiary methyl-phosphine oxides
Michalski et al.	1970	Organophosphorus compounds. Part CXXXVI. Thiopyrophosphate synthesis by condensation of oxophosphoranesulphenyl chlorides with trialkyl phosphites and their structural analogues
US20040254269A1 (en)	2004-12-16	Organosilicon compounds that can be used as a coupling agent