USRE23270E - X-dimethyl-z - Google Patents
X-dimethyl-z Download PDFInfo
- Publication number
- USRE23270E USRE23270E US23270DE USRE23270E US RE23270 E USRE23270 E US RE23270E US 23270D E US23270D E US 23270DE US RE23270 E USRE23270 E US RE23270E
- Authority
- US
- United States
- Prior art keywords
- compound
- dimethyl
- jour
- chem
- vol
- 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
- 150000001875 compounds Chemical class 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 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 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- RJCTVFQQNCNBHG-UHFFFAOYSA-N chloromethyl-dimethyl-phenylsilane Chemical compound ClC[Si](C)(C)C1=CC=CC=C1 RJCTVFQQNCNBHG-UHFFFAOYSA-N 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- -1 methyl Grignard reagent Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920001558 organosilicon polymer Polymers 0.000 description 1
- 238000000746 purification 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
Definitions
- the compound of this invention may be prepared by a condensation reaction between chlorophenyltrimethylsilane and in the presence of sodium.
- the latter compound may be obtained by reacting a methyl Grignard reagent with the compound C13SiCH2SiC13 and purification by distillation.
- the condensation reaction proceeds according to the equation
- the compound of this invention is a clear oil having a viscosity of 23.3 cs. at 25 C., a boiling point of 171 C. at 1 mm, a freezing point of 54 C., a refractive index of 1.5113 at 25 C. and a density of 0.923 at 25 C.
- This material is stable when heated at a temperature of 365 C. in the absence of oxygen and is stable at temperatures up to 200 C. in the presence of oxygen.
- the compound performs satisfactorily when used to lubricate the bearing surfaces of moving metallic parts. It is also a good vacuum diffusion pump fluid as is shown by the following tests.
- a sample of the compound was placed in a single stage diffusion pump and operated at 135 C. with a fore pressure of 30 microns. A vacuum of 8.1x 1() mm. was. obtained. During the operation of the pump the material showed no Sign of deterioration.
- a method of preparing Ha] Ha CH3 which comprises reacting chlorophenyltrimethyl-- silane and Cl(CH3) 2SiCH2Si(CH3) 201 by contacting a mixture thereof with'metallic sodium.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Description
Reissuecl Sept. 26, 1950 2,4 -DIME THYL-ZA-TRIMETHYLSILYL PHENYL- ZA-DISILAPENTAN E Harold A. Clark, Midland, Mich., assignor to Dow Corning Corporation, Midland, Mich., a corporation of Michigan No Drawing. Original No. 2,507,514, dated May 16, 1950, Serial No. 77,989, February 23, 1949. Application for reissue June 22, 1950, Serial No.
2 Claims.
Matter enclosed in heavy brackets E 1 appears in the original patent but forms no part of this reissue specification; matter printed in italics indicates the additions made by reissue This invention relates to an organo silicon polymer.
It is an object of this invention to prepare a thermally stable compound which is of particular utility as a lubricant and a vacuum diffusion pump fluid. Other objects and advantage will be apparent from the following description.
This invention relates to the compound The compound of this invention may be prepared by a condensation reaction between chlorophenyltrimethylsilane and in the presence of sodium. The latter compound may be obtained by reacting a methyl Grignard reagent with the compound C13SiCH2SiC13 and purification by distillation. The condensation reaction proceeds according to the equation The compound of this invention is a clear oil having a viscosity of 23.3 cs. at 25 C., a boiling point of 171 C. at 1 mm, a freezing point of 54 C., a refractive index of 1.5113 at 25 C. and a density of 0.923 at 25 C. This material is stable when heated at a temperature of 365 C. in the absence of oxygen and is stable at temperatures up to 200 C. in the presence of oxygen. The compound performs satisfactorily when used to lubricate the bearing surfaces of moving metallic parts. It is also a good vacuum diffusion pump fluid as is shown by the following tests.
A sample of the compound was placed in a single stage diffusion pump and operated at 135 C. with a fore pressure of 30 microns. A vacuum of 8.1x 1() mm. was. obtained. During the operation of the pump the material showed no Sign of deterioration.
In order that this invention may be better understood, recourse should be had to the following example, which should be considered as illustrative only.
EXAMPLE then filtered and the toluene was removed at reduced pressure. The residue was a clear oil which distilled at 171 C. at 1 mm. pressure. The compound was found to have a molar refraction of 141.77.
That which is claimed is:
(0H3)381C5HASlCHZSiCBH4Sl GH3 3 Ha H 2. A method of preparing Ha] Ha CH3 which comprises reacting chlorophenyltrimethyl-- silane and Cl(CH3) 2SiCH2Si(CH3) 201 by contacting a mixture thereof with'metallic sodium.
HAROLD A. CLARK.
REFERENCES CITED The following references are of record in the file of this patent or the original patent:
Goodwin: Jour. Am. Chem. $00., vol. 69 (194'?) page 2247.
Sommer: Jour. Am. Chem. Soc, vol. 69 (1947) page 980.
Bluestein: "Jour. Am. Chem. $00., vol. 70 (1948) pages 3068-3071.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77989A US2507514A (en) | 1949-02-23 | 1949-02-23 | 2, 4-dimethyl-2, 4-trimethylsilylphenyl-2, 4-disilapentane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USRE23270E true USRE23270E (en) | 1950-09-26 |
Family
ID=22141197
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US23270D Expired USRE23270E (en) | 1949-02-23 | X-dimethyl-z | |
| US77989A Expired - Lifetime US2507514A (en) | 1949-02-23 | 1949-02-23 | 2, 4-dimethyl-2, 4-trimethylsilylphenyl-2, 4-disilapentane |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US77989A Expired - Lifetime US2507514A (en) | 1949-02-23 | 1949-02-23 | 2, 4-dimethyl-2, 4-trimethylsilylphenyl-2, 4-disilapentane |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US2507514A (en) |
| DE (1) | DE854518C (en) |
| FR (1) | FR1008404A (en) |
| GB (1) | GB669178A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2689860A (en) * | 1950-08-08 | 1954-09-21 | Montclair Res Corp | Polysilyl derivatives |
| US3139448A (en) * | 1961-10-31 | 1964-06-30 | Ici Ltd | Chlorophenyl substituted di-and trisilaalkanes |
| US5013872A (en) * | 1989-05-12 | 1991-05-07 | Masco Building Products Corp. | Cable clamp |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1149837B1 (en) * | 2000-04-25 | 2007-03-14 | Shin-Etsu Chemical Co., Ltd. | Organosilicon compounds |
-
0
- US US23270D patent/USRE23270E/en not_active Expired
-
1949
- 1949-02-23 US US77989A patent/US2507514A/en not_active Expired - Lifetime
-
1950
- 1950-01-16 GB GB1114/50A patent/GB669178A/en not_active Expired
- 1950-01-16 FR FR1008404D patent/FR1008404A/en not_active Expired
- 1950-09-24 DE DED6064A patent/DE854518C/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2689860A (en) * | 1950-08-08 | 1954-09-21 | Montclair Res Corp | Polysilyl derivatives |
| US3139448A (en) * | 1961-10-31 | 1964-06-30 | Ici Ltd | Chlorophenyl substituted di-and trisilaalkanes |
| US5013872A (en) * | 1989-05-12 | 1991-05-07 | Masco Building Products Corp. | Cable clamp |
Also Published As
| Publication number | Publication date |
|---|---|
| US2507514A (en) | 1950-05-16 |
| FR1008404A (en) | 1952-05-19 |
| GB669178A (en) | 1952-03-26 |
| DE854518C (en) | 1952-11-04 |
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