GB823235A - Preparation of a zinc dialkyl dithiophosphate product - Google Patents
Preparation of a zinc dialkyl dithiophosphate productInfo
- Publication number
- GB823235A GB823235A GB8965/56A GB896556A GB823235A GB 823235 A GB823235 A GB 823235A GB 8965/56 A GB8965/56 A GB 8965/56A GB 896556 A GB896556 A GB 896556A GB 823235 A GB823235 A GB 823235A
- Authority
- GB
- United Kingdom
- Prior art keywords
- zinc
- reaction product
- product
- alkanol
- dialkyl dithiophosphate
- 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 title abstract 4
- 239000011701 zinc Substances 0.000 title abstract 4
- 229910052725 zinc Inorganic materials 0.000 title abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 4
- 239000007795 chemical reaction product Substances 0.000 abstract 4
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 2
- 239000000654 additive Substances 0.000 abstract 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 abstract 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 abstract 2
- 239000010687 lubricating oil Substances 0.000 abstract 2
- 238000006386 neutralization reaction Methods 0.000 abstract 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 abstract 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 2
- 150000003752 zinc compounds Chemical class 0.000 abstract 2
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 230000000996 additive effect Effects 0.000 abstract 1
- 230000032683 aging Effects 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 239000002518 antifoaming agent Substances 0.000 abstract 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052788 barium Inorganic materials 0.000 abstract 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003599 detergent Substances 0.000 abstract 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- 229920002545 silicone oil Polymers 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 229940007718 zinc hydroxide Drugs 0.000 abstract 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 abstract 1
- 239000011787 zinc oxide Substances 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric 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)
- Lubricants (AREA)
Abstract
A zinc dialkyl dithiophosphate product particularly adapted for use as an improvement agent for lubricating oils is obtained by reacting phosphorus pentasulphide in a molar ratio of substantially 1 to 4 with an alcohol ROH wherein R is a higher alkyl radical of 6 to 18 carbon atoms at elevated temperature to form a reaction product containing a dialkyl dithiophosphoric acid, treating the reaction product with an alcohol having the formula R1OH wherein R1 is a lower alkyl radical having up to 4 carbon atoms at about 170 DEG F. to about 200 DEG F. for from about 1/2 to about 2 1/2 hours, neutralizing the product with a compound containing zinc to form a reaction product containing the zinc dialkyl dithiophosphate and ageing said reaction product by subjecting it to a temperature within the range of from about 140 DEG F. to 195 DEG F. for from about 1/2 to 6 hours. Specified higher alcohols are 4-methyl-2-pentanol (methylisobutylcarbinol), n-hexanol, n-octanol, iso-octanol, dodecanol, hexadecanol and octadecanol and specified lower alkanols are methanol, ethanol, propanol, isopropanol and butanol. The amount of lower alkanol may be from about 5 to 25% of the weight of the higher alkanol originally reacted with the phosphorus pentasulphide. The neutralization with the zinc compound may be effected by adding up to 150% of the theoretical excess of a zinc compound such as zinc oxide or hydroxide until a hydrogen sulphide test is negative. The neutralized, aged product may be blended with other additives such as silicone oil anti-foam agents, detergents such as sodium or barium petroleum sulphonate, dropped to a still, stripped, and then filtered. A blending oil (hydrocarbon lubricating oil) may be added before or during the neutralization or after the stripping or filtering to bring the concentration of the additive to a desired range. In the examples given, methyl isobutyl carbinol is used as the higher alkanol and ethanol, isopropanol and n-butanol respectively as the lower alkanol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US507984A US2837549A (en) | 1955-05-12 | 1955-05-12 | Zinc dialkyl dithiophosphates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB823235A true GB823235A (en) | 1959-11-11 |
Family
ID=24020906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8965/56A Expired GB823235A (en) | 1955-05-12 | 1956-03-22 | Preparation of a zinc dialkyl dithiophosphate product |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2837549A (en) |
| GB (1) | GB823235A (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3121687A (en) * | 1958-06-30 | 1964-02-18 | Sinclair Research Inc | Lubricating oil compositions containing sulfonates |
| US2983742A (en) * | 1959-03-11 | 1961-05-09 | Gulf Oil Corp | Decolorizing and improving metal salts of partial esters of dithiophosphoric acids |
| US2990297A (en) * | 1959-12-21 | 1961-06-27 | California Research Corp | Flameroofing of wood and article |
| GB1089463A (en) * | 1965-02-24 | 1967-11-01 | Exxon Research Engineering Co | Improvements in or relating to grease compositions |
| US3514476A (en) * | 1966-09-28 | 1970-05-26 | Monsanto Co | Making basic zinc double salts of o,o-dialkyl phosphorodithioic acids |
| US4215067A (en) * | 1978-12-29 | 1980-07-29 | Standard Oil Company (Indiana) | Process for the preparation of zinc salts of dihydrocarbyldithiophosphoric acids |
| US5569643A (en) * | 1991-03-07 | 1996-10-29 | Nippon Oil Co., Ltd. | Grease composition for constant velocity joint |
| JP2799634B2 (en) * | 1991-03-07 | 1998-09-21 | 日本石油株式会社 | Grease composition for constant velocity joints |
| US20080125337A1 (en) * | 2006-11-29 | 2008-05-29 | Guinther Gregory H | Lubricant formulations and methods |
| US8084403B2 (en) * | 2009-05-01 | 2011-12-27 | Afton Chemical Corporation | Lubricant formulations and methods |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2368000A (en) * | 1941-12-04 | 1945-01-23 | American Cyanamid Co | Lubricating compositions |
| US2344393A (en) * | 1942-02-18 | 1944-03-14 | American Cyanamid Co | Lubricating oil composition |
| US2358305A (en) * | 1942-07-30 | 1944-09-19 | American Cyanamid Co | Lubricating composition |
| US2466408A (en) * | 1946-01-26 | 1949-04-05 | American Cyanamid Co | Lubricating composition |
| BE510012A (en) * | 1951-03-29 |
-
1955
- 1955-05-12 US US507984A patent/US2837549A/en not_active Expired - Lifetime
-
1956
- 1956-03-22 GB GB8965/56A patent/GB823235A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US2837549A (en) | 1958-06-03 |
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