GB829064A - Catalysis of phosphosulfurization reactions - Google Patents
Catalysis of phosphosulfurization reactionsInfo
- Publication number
- GB829064A GB829064A GB9836/58A GB983658A GB829064A GB 829064 A GB829064 A GB 829064A GB 9836/58 A GB9836/58 A GB 9836/58A GB 983658 A GB983658 A GB 983658A GB 829064 A GB829064 A GB 829064A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphorus
- glycerine
- phenol
- alcohols
- alcohol
- 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
- 238000006555 catalytic reaction Methods 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 title 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 6
- 235000011187 glycerol Nutrition 0.000 abstract 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 4
- 150000001298 alcohols Chemical class 0.000 abstract 4
- -1 aliphatic alcohols Chemical class 0.000 abstract 4
- 230000003197 catalytic effect Effects 0.000 abstract 4
- 150000002989 phenols Chemical class 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 abstract 3
- 229930195733 hydrocarbon Natural products 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 150000005673 monoalkenes Chemical class 0.000 abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 2
- 229920002367 Polyisobutene Polymers 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000001569 carbon dioxide Substances 0.000 abstract 2
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052734 helium Inorganic materials 0.000 abstract 2
- 239000001307 helium Substances 0.000 abstract 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000003208 petroleum Substances 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical group S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 229920000098 polyolefin Polymers 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000004698 Polyethylene Substances 0.000 abstract 1
- 239000004743 Polypropylene Substances 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 238000004523 catalytic cracking Methods 0.000 abstract 1
- 235000019864 coconut oil Nutrition 0.000 abstract 1
- 239000003240 coconut oil Substances 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 239000010779 crude oil Substances 0.000 abstract 1
- 229920001519 homopolymer Polymers 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 239000010687 lubricating oil Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 229920000573 polyethylene Polymers 0.000 abstract 1
- 229920001155 polypropylene Polymers 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 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
- C07F9/04—Reaction products of phosphorus sulfur compounds with hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Hydrocarbons are phosphosulphurized by reacting them with a phosphorus sulphide or a mixture of phosphorus and sulphur at elevated temperature in the presence of a catalytic amount, in the range 0.001 to 0.1% by weight based on the total reactants, of glycerine or a compound which is an aliphatic alcohol or a phenol and has 4 to 32 carbon atoms. Suitable hydrocarbons are those having a molecular weight of 300 to 100,000, e.g. C2 to C10 monoolefin polymers (see Group IV(a)) and petroleum bright stocks boiling above 700 DEG F. The petroleum bright stocks may be obtained by topping crude oils and extracting or deasphalting the residues to obtain material having viscosities above 100 S.U.S. at 210 DEG F., viscosity indices above 80, and initial boiling points above 700 DEG F. Bright stocks from catalytic cracking cycle stocks may also be used. The alcohols and phenols (including alkylated phenols) may contain one or more hydroxy groups and may contain other substituent groups, e.g. -COOH, -NH2, or -NO2, that do not interfere with their catalytic properties. Specified hydroxy compounds are m-butyl alcohol, diethylene glycol, C10 to C18 aliphatic monohydric alcohols, glycerine, C32 Guerbet alcohol and phenol. The preferred phosphorus sulphide is phosphorus pentasulphide and phosphosulphurization is generally effected at between 350 DEG and 600 DEG F., preferably in a non-oxidizing atmosphere, e.g. under a blanket of nitrogen, carbon dioxide, or helium.ALSO:C2-C10 mono-olefin polymers having a molecular weight of 500 to 100,000, are phosphosulphurized by reacting them with a phosphorus sulphide, especially phosphorus pentasulphide, or a mixture of phosphorus and sulphur at elevated temperature in the presence of a catalytic amount, in the range of 0.001 to 0.1% by weight based on the total reactants, of glycerine or a compound which is an aliphatic alcohol or a phenol and has 4 to 32 carbon atoms. The alcohols and phenols (which include alkylated phenols) may contain one or more hydroxy groups and may contain other substituent groups, e.g. -COOH, -NH2, or -NO2, that do not interfere with their catalytic properties. Specified hydroxy compounds are n-butyl alcohol, C10 to C10 monohydric aliphatic alcohols, diethylene glycol, phenol, glycerine and C32 Guerbet alcohol. The mon-olefin polymer may be a homopolymer, or a copolymer of a mono-olefin and another olefin, e.g. a vinyl hydrocarbon such as styrene or a diolefine, e.g. isoprene. Specified polymers are polyethylene, polypropylene and polyisobutylene. The phosphosulphurization is generally effected at between 350 DEG and 600 DEG F., preferably in a nonoxidizing atmosphere, e.g. under a blanket of nitrogen, carbon dioxide or helium. An example is given in which polyisobutylene having a molecular weight of 100 (Staudinger) is reacted with P2S5 at 425 DEG F. in an atmosphere of nitrogen and in the presence of (1) a commercial mixture of C14, C12, C16, C18 and C10 alcohols obtained by hydrogenation of coconut oil, (2) n-butyl alcohol, (3) glycerine, (4) phenol, and (5) C32 Guerbet alcohol respectively. The products find application as lubricating oil additives.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US829064XA | 1957-04-25 | 1957-04-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB829064A true GB829064A (en) | 1960-02-24 |
Family
ID=22174210
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB9836/58A Expired GB829064A (en) | 1957-04-25 | 1958-03-27 | Catalysis of phosphosulfurization reactions |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB829064A (en) |
-
1958
- 1958-03-27 GB GB9836/58A patent/GB829064A/en not_active Expired
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