US3067225A - Process of preparing tetraaryl tin - Google Patents
Process of preparing tetraaryl tin Download PDFInfo
- Publication number
- US3067225A US3067225A US708748A US70874858A US3067225A US 3067225 A US3067225 A US 3067225A US 708748 A US708748 A US 708748A US 70874858 A US70874858 A US 70874858A US 3067225 A US3067225 A US 3067225A
- Authority
- US
- United States
- Prior art keywords
- tin
- aryl
- tetraaryl
- alkali metal
- grams
- 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 - Lifetime
Links
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims description 13
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 12
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 12
- 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 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- -1 diaryl-tin halide Chemical class 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 description 3
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 1
- PLOSSHSFATUNTF-UHFFFAOYSA-N [K]C1=CC=CC=C1 Chemical compound [K]C1=CC=CC=C1 PLOSSHSFATUNTF-UHFFFAOYSA-N 0.000 description 1
- MKZIXXFZWGUNJM-UHFFFAOYSA-L bis(4-methylphenyl)tin(2+);dichloride Chemical compound C1=CC(C)=CC=C1[Sn](Cl)(Cl)C1=CC=C(C)C=C1 MKZIXXFZWGUNJM-UHFFFAOYSA-L 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07F7/22—Tin compounds
- C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen
Definitions
- the present invention relates to a process leading to much more favorable yields of 85-90% of the theoretical yield calculated upon the tin tetrahalide used.
- the process is based on the surprising observation that an aryl-tin halide, particularly diaryl-tin halide, but also triaryl-tin monohalide or monoaryl-tin trihalide, reacts in a more favorable manner with aryl alkali metal than tin tetrahalide.
- a part of the tin tetraaryl compound, the desired end product disproportionates with tin tetrahalide to give an aryl-tin halide (cf. Kocheshkov, Ber.
- the first reaction phase viz. the disproportionation of the tetraaryl tin
- the second phase viz. the reaction of the aryl-tin halide with aryl alkali metal to yield the tin tetraaryl compound, takes place at temperatures between 20 C. and +80 C., preferably between +4 C. and +5 C. In this case it is advisable to apply the aryl alkali metal in an excess of -25%.
- alkali metal aryl compounds may be used aryllithium and aryl-potassium.
- Example 1 1st phase: 1280 grams of tetraphenyl tin are slowly heated with 782 grams of tin tetrachloride to 220-230 C. and maintained for 2 hours at this temperature. After cooling, the reaction product is dissolved in 1200 cc. of benzene;
- Example 2 instead of the phenyl sodium used in Example 1, there may also be used phenyl potassium that is obtained by reaction of 1820 grams of chlorobenzene with potassium.
- Example 1 The method of working and the starting materials used a are the same as indicated in Example 1.
- Example 3 967 grams of tetra-para-tolyl-tin are reacted within 3 hours at 240 C. with 532 grams of tin tetrachloride to mainly di-para-tolyl-tin-dichloride and the reaction product is dissolved in 800 cc. of benzene. To this solution is slowly added, while stirring and permanently cooling to +5 C., a suspension of para-tolyl-sodium obtained from 460 grams of sodium, 1365 grams of para-chlorotoluene or 1845 grams of para-bromotoluene and 1800 cc. of benzene. After a reaction period of about 3 hours the reaction mixture is refluxed for about 30 minutes. The tetra-para-tolyl-tin thus obtained is worked up as described in Example 1. There are obtained 1750 grams of tetra-para-tolyl-tin melting at 235-236 C.
- a method of raising the yield of tetraaryl tin to at least 80%, calculated upon the tin tetrachloride used which comprises combining in a first step at a temperature between 200 and 230 C. tin tetrachloride and tetraaryl tin to form an aryl-tin chloride, and reacting in a second step the aryltin chloride so obtained with aryl alkali metal at a temperature between +4 and +5 C. to form tetraaryl tin, said aryl being a member selected from the group consisting of phenyl and tolyl, and said alkali metal being a member selected from the group consisting of sodium, potassium and lithium.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF22163A DE1027669B (de) | 1957-01-18 | 1957-01-18 | Verfahren zur Herstellung von Tetraarylzinn |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3067225A true US3067225A (en) | 1962-12-04 |
Family
ID=7090342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US708748A Expired - Lifetime US3067225A (en) | 1957-01-18 | 1958-01-14 | Process of preparing tetraaryl tin |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3067225A (fr) |
| BE (1) | BE564074A (fr) |
| DE (1) | DE1027669B (fr) |
| FR (1) | FR1197949A (fr) |
| GB (1) | GB861459A (fr) |
| NL (2) | NL106537C (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3454610A (en) * | 1966-05-26 | 1969-07-08 | Dow Chemical Co | Synthesis of organometallic halides by redistribution |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2431038A (en) * | 1944-07-24 | 1947-11-18 | Monsanto Chemicals | Tin hydrocarbon compounds and process for making same |
| US2570686A (en) * | 1948-05-04 | 1951-10-09 | Metal & Thermit Corp | Process for making tin hydrocarbons |
| US2599557A (en) * | 1948-03-24 | 1952-06-10 | Metal & Thermit Corp | Process for making organotin halides |
-
0
- NL NL223989D patent/NL223989A/xx unknown
- NL NL106537D patent/NL106537C/xx active
- BE BE564074D patent/BE564074A/xx unknown
-
1957
- 1957-01-18 DE DEF22163A patent/DE1027669B/de active Pending
-
1958
- 1958-01-14 US US708748A patent/US3067225A/en not_active Expired - Lifetime
- 1958-01-17 FR FR1197949D patent/FR1197949A/fr not_active Expired
- 1958-01-17 GB GB1765/58A patent/GB861459A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2431038A (en) * | 1944-07-24 | 1947-11-18 | Monsanto Chemicals | Tin hydrocarbon compounds and process for making same |
| US2599557A (en) * | 1948-03-24 | 1952-06-10 | Metal & Thermit Corp | Process for making organotin halides |
| US2570686A (en) * | 1948-05-04 | 1951-10-09 | Metal & Thermit Corp | Process for making tin hydrocarbons |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3454610A (en) * | 1966-05-26 | 1969-07-08 | Dow Chemical Co | Synthesis of organometallic halides by redistribution |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1197949A (fr) | 1959-12-03 |
| NL106537C (fr) | 1900-01-01 |
| NL223989A (fr) | 1900-01-01 |
| BE564074A (fr) | 1900-01-01 |
| GB861459A (en) | 1961-02-22 |
| DE1027669B (de) | 1958-04-10 |
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