US3595892A - Process for the production of alkylor cycloalkyl tin halides - Google Patents
Process for the production of alkylor cycloalkyl tin halides Download PDFInfo
- Publication number
- US3595892A US3595892A US744701A US3595892DA US3595892A US 3595892 A US3595892 A US 3595892A US 744701 A US744701 A US 744701A US 3595892D A US3595892D A US 3595892DA US 3595892 A US3595892 A US 3595892A
- Authority
- US
- United States
- Prior art keywords
- tin
- antimony
- alkyl
- halides
- butyl
- 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
- -1 cycloalkyl tin halides Chemical class 0.000 title abstract description 41
- 238000000034 method Methods 0.000 title abstract description 30
- 230000008569 process Effects 0.000 title abstract description 29
- 238000004519 manufacturing process Methods 0.000 title abstract description 12
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract description 44
- 238000006243 chemical reaction Methods 0.000 abstract description 32
- 239000000203 mixture Substances 0.000 abstract description 20
- 239000003054 catalyst Substances 0.000 abstract description 12
- 150000004820 halides Chemical class 0.000 abstract description 6
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 abstract description 5
- 125000000217 alkyl group Chemical group 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229910052787 antimony Inorganic materials 0.000 description 10
- 150000001350 alkyl halides Chemical class 0.000 description 9
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 9
- BXJWDOYMROEHEN-UHFFFAOYSA-N tributylstibane Chemical compound CCCC[Sb](CCCC)CCCC BXJWDOYMROEHEN-UHFFFAOYSA-N 0.000 description 8
- YMLFYGFCXGNERH-UHFFFAOYSA-K butyltin trichloride Chemical class CCCC[Sn](Cl)(Cl)Cl YMLFYGFCXGNERH-UHFFFAOYSA-K 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 125000000962 organic group Chemical group 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 3
- 150000001347 alkyl bromides Chemical class 0.000 description 3
- 150000001348 alkyl chlorides Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- FAWGZAFXDJGWBB-UHFFFAOYSA-N antimony(3+) Chemical compound [Sb+3] FAWGZAFXDJGWBB-UHFFFAOYSA-N 0.000 description 3
- ZDINGUUTWDGGFF-UHFFFAOYSA-N antimony(5+) Chemical compound [Sb+5] ZDINGUUTWDGGFF-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- WUOBERCRSABHOT-UHFFFAOYSA-N diantimony Chemical class [Sb]#[Sb] WUOBERCRSABHOT-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 235000011150 stannous chloride Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 3
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- OWPAOTUJVBAUBW-UHFFFAOYSA-M bromo(dibutyl)stibane Chemical compound CCCC[Sb](Br)CCCC OWPAOTUJVBAUBW-UHFFFAOYSA-M 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- QSHZUFRQHSINTB-UHFFFAOYSA-L dibutyltin(2+);dibromide Chemical compound CCCC[Sn](Br)(Br)CCCC QSHZUFRQHSINTB-UHFFFAOYSA-L 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000004694 iodide salts Chemical class 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- QPBYLOWPSRZOFX-UHFFFAOYSA-J tin(iv) iodide Chemical compound I[Sn](I)(I)I QPBYLOWPSRZOFX-UHFFFAOYSA-J 0.000 description 2
- 125000005425 toluyl group Chemical group 0.000 description 2
- BYQWEYFCJKJRHO-UHFFFAOYSA-K tribromo(butyl)stannane Chemical compound CCCC[Sn](Br)(Br)Br BYQWEYFCJKJRHO-UHFFFAOYSA-K 0.000 description 2
- FVRKTAOFDKFAMI-UHFFFAOYSA-M tributylstannanylium;bromide Chemical compound [Br-].CCCC[Sn+](CCCC)CCCC FVRKTAOFDKFAMI-UHFFFAOYSA-M 0.000 description 2
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 2
- UWLHSHAHTBJTBA-UHFFFAOYSA-N 1-iodooctane Chemical compound CCCCCCCCI UWLHSHAHTBJTBA-UHFFFAOYSA-N 0.000 description 1
- PTBXOARBTPRBHN-UHFFFAOYSA-N 4-oxo-7h-thieno[2,3-b]pyridine-5-carboxylic acid Chemical compound O=C1C(C(=O)O)=CNC2=C1C=CS2 PTBXOARBTPRBHN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000428198 Lutrinae Species 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- RPJGYLSSECYURW-UHFFFAOYSA-K antimony(3+);tribromide Chemical compound Br[Sb](Br)Br RPJGYLSSECYURW-UHFFFAOYSA-K 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CJVDZIUUPSJIHH-UHFFFAOYSA-M bromo-bis(ethenyl)stibane Chemical compound C(=C)[Sb](C=C)Br CJVDZIUUPSJIHH-UHFFFAOYSA-M 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QOUGGLDEJWUQFA-UHFFFAOYSA-N butyl(methyl)tin Chemical class CCCC[Sn]C QOUGGLDEJWUQFA-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- SSXPEHBFLFUZCU-UHFFFAOYSA-M chloro(diphenyl)stibane Chemical compound C=1C=CC=CC=1[Sb](Cl)C1=CC=CC=C1 SSXPEHBFLFUZCU-UHFFFAOYSA-M 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 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 1
- LIVZJRZLOSWBSE-UHFFFAOYSA-K cyclohexyltin(3+);tribromide Chemical class Br[Sn](Br)(Br)C1CCCCC1 LIVZJRZLOSWBSE-UHFFFAOYSA-K 0.000 description 1
- HNJUOMOFQQQJAS-UHFFFAOYSA-L dibromo(butyl)stibane Chemical compound C(CCC)[Sb](Br)Br HNJUOMOFQQQJAS-UHFFFAOYSA-L 0.000 description 1
- OUIYOIUXAQHPIX-UHFFFAOYSA-L dibromo(phenyl)stibane Chemical compound Br[Sb](Br)C1=CC=CC=C1 OUIYOIUXAQHPIX-UHFFFAOYSA-L 0.000 description 1
- TVNLJOAPGNUGKE-UHFFFAOYSA-L dibromo(tributyl)-$l^{5}-stibane Chemical compound CCCC[Sb](Br)(Br)(CCCC)CCCC TVNLJOAPGNUGKE-UHFFFAOYSA-L 0.000 description 1
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 1
- UELMXNATZOHQOV-UHFFFAOYSA-N dibutyl(ethyl)stibane Chemical compound C(C)[Sb](CCCC)CCCC UELMXNATZOHQOV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- JVFNASPYONXEIE-UHFFFAOYSA-M tetrabutylstibanium;bromide Chemical compound CCCC[Sb](Br)(CCCC)(CCCC)CCCC JVFNASPYONXEIE-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CUDGTZJYMWAJFV-UHFFFAOYSA-N tetraiodogermane Chemical compound I[Ge](I)(I)I CUDGTZJYMWAJFV-UHFFFAOYSA-N 0.000 description 1
- CTNFMWSFOVTSNU-UHFFFAOYSA-N tetraphenylantimony Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CTNFMWSFOVTSNU-UHFFFAOYSA-N 0.000 description 1
- RTIPRBMUMNKBRW-UHFFFAOYSA-M tetraphenylstibanium;iodide Chemical compound C=1C=CC=CC=1[Sb](C=1C=CC=CC=1)(I)(C=1C=CC=CC=1)C1=CC=CC=C1 RTIPRBMUMNKBRW-UHFFFAOYSA-M 0.000 description 1
- JTDNNCYXCFHBGG-UHFFFAOYSA-L tin(ii) iodide Chemical compound I[Sn]I JTDNNCYXCFHBGG-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- BMRKNRNFWARTTN-UHFFFAOYSA-K tribromo(octyl)stannane Chemical class CCCCCCCC[Sn](Br)(Br)Br BMRKNRNFWARTTN-UHFFFAOYSA-K 0.000 description 1
- WCESUTSPHBVTRG-UHFFFAOYSA-N tributyl(diethyl)-$l^{5}-stibane Chemical compound CCCC[Sb](CC)(CC)(CCCC)CCCC WCESUTSPHBVTRG-UHFFFAOYSA-N 0.000 description 1
- YSCVYRUCAPMZFG-UHFFFAOYSA-K trichlorotin Chemical compound Cl[Sn](Cl)Cl YSCVYRUCAPMZFG-UHFFFAOYSA-K 0.000 description 1
- AVYPTBDUFIEJDP-UHFFFAOYSA-N tricyclohexylstibane Chemical compound C1CCCCC1[Sb](C1CCCCC1)C1CCCCC1 AVYPTBDUFIEJDP-UHFFFAOYSA-N 0.000 description 1
- KKOFCVMVBJXDFP-UHFFFAOYSA-N triethylstibane Chemical compound CC[Sb](CC)CC KKOFCVMVBJXDFP-UHFFFAOYSA-N 0.000 description 1
- ZHNFFTWMBZYWNF-UHFFFAOYSA-N trioctylstibane Chemical compound CCCCCCCC[Sb](CCCCCCCC)CCCCCCCC ZHNFFTWMBZYWNF-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
- This invention relates to an improved process for the production of alkylor cycloalkyl tin halides by the direct reaction of metallic tin with alkylor cycloalkyl halides, comprising carrying out the reaction in the presence of an organo-antimony compound, or a mixture consisting of organo-antimony compounds as a catalyst.
- the present invention relates to a process for the production of alkylor cycloalkyl tin halides, respectively, by the direction reaction of metallic tin with alkyland cycloalkyl halides, respectively, or mixtures of alkyland/or cycloalkyl halides.
- alkyl halides in which the alkyl group contains more than four carbon atoms.
- the reaction may be carried out in the presence of an alcohol, an ether, an ester or tetrahydrofuran and in the presence of certain metals and/or alkyl metal halides.
- specific solvents however, is a serious drawback of this known process.
- alkyl tin halides by direct reaction of metallic tin with alkyl halides, by means of which process both alkyl bromides and alkyl chlorides with lower alkyl groups, such as the ethyl-, propyland butyl compounds, and alkyl bromides and alkyl chlorides with higher alkyl groups, such as the hexyl-, heptyland octyl compounds, as well as cycloalkyl halides, such as the cyclohexyl compounds, can be converted to mixtures of the corresponding alkyland cycloalkyl tin halides, respectively, with good yields, and without the necessity of using specific solvents.
- the process for the production of alkyl or cycloalkyl tin halides by the direct reaction of metallic tin with alkylor cycloalkyl halides, respectively, or mixtures of alkyl and/or cycloalkyl halides at higher temperatures is characterised by the fact, that the reaction is carried out in the presence of a catalytic amount of an organo-antimony compound or a mixture consisting of organo-antimony compounds.
- dialkyland dicycloalkyl tin dihalides are obtained as the main product of the reaction
- monoalkyland monocycloalkyl tin trihalides are formed as by-products, as well as, most often in smaller quantities, the trialkyland tricycloalkyl tin monohalides, respectively.
- organo-antimony compound a compound of trivalent or pentavalent antimony, in which at least one alkyl-, alkenyl-, cycloalkyl-, aryl-, alkarylor aralkyl group is directly bonded to an antimony atom. If there are two or more of the said groups in the compound, these groups may diifer.
- Compounds of a more complex structure such as tetraorgano diantimony compounds or complexes of tetraorgano antimony with metal halides or with halogens, are also included in the above definition.
- organo-antimony compounds which may be used as catalysts according to this invention: triethyl antimony, tri-n-butyl antimony, tri-isobutyl antimony, di-n-butyl antimony bromide, dim-butyl antimony chloride, monobutyl antimony dibromide, ethyl dibutyl antimony, tetrabutyl antimony bromide, tri-butyl antimony dibromide, diethyl tributyl antimony, tri-n-octyl antimony, di-noctyl antimony bromide, divinyl antimony bromide, tricyclohexyl antimony, triphenyl antimony, diphenyl antimony chloride, phenyl antimony dibromide, tetraphenyl antimony bromide, tolyl antimony dibromide, tribenzyl antimony, tetraphenyl diantimony, bis(tetrabuty1 antimony
- the organoantimony compounds are mostly added in amounts varying from 1 to 8 mol. percent, calculated on the tin used, preferably in amounts from 3 to 5 mol. percent.
- an organo-antimony compound in which the organic group(s) is (are) the same as the alkylor cycloalkyl group, respectively, in the halide to be converted is advisable to use, as a catalyst, an organo-antimony compound in which the organic group(s) is (are) the same as the alkylor cycloalkyl group, respectively, in the halide to be converted.
- the iodide can also be added in the form of an alkylor cycloalkyl tin iodide, respectively, e.g. as dialkyl tin diiodide or tin tetraiodide.
- the process according to this invention may be carried out using the amounts of alkylor cycloalkyl halide, respectively, and tin in proportions which can be varied within wide limits.
- tin in proportions which can be varied within wide limits.
- the form and quality of the tin used as the starting material are not determinative for the carrying out of the process. In most cases, it is possible to achieve a very good reaction when using tin in the form of fine shavings but is is also possible to use fine or coarser powdered tin as the starting material.
- the reaction is carried out at temperatures between 130 and 210 C.; the reaction temperature is preferably chosen between 160 and 180 C.
- the process can be carried out both in a closed system under pressure and in an open system under atmospheric pressure, in which case the evaporating liquid is recycled by means of a reflux condenser.
- the reaction mixture obtained can be further processed and the alkylor cycloalkyl tin halides, respectively, can be purified according to known processes, e.g. by means of distillation.
- the alkylor cycloalkyl tin halides can be purified according to known processes, e.g. by means of distillation.
- For an analytical determination of the composition of the mixture good use can be made of the gas chromatographic method.
- alkylor cycloalkyl tin halides obtained according to the process of the present invention, in particular the dialkylor dicycloalkyl tin dihalides, constitute valuable intermediates for the preparation of alkylor cycloalkyl tin compounds, respectively, which are applied as plastics additives.
- EXAMPLE 1 6.0 g. pure tin in the form of fine shavings (0.1 to 0.3 mm. thick) and 21.0 g. n-butyl bromide are introduced into a Carius tube. After the air has been displaced by nitrogen 0.5 g. di-n-butyl antimony bromide is added and the tube is next heated under autogenous pressure at 180 C. for 16 hours, during which the tin completely goes into solution.
- reaction mixture is heated under autogenous pressure for 16 hours at180 C. in a Carius tube, in which the air has been displaced by nitrogen. After the experiment has been completed, the reaction mixture is further processed in the same way as described in Example 1.
- EXAMPLE 5 A mixture of the same composition as indicated in Example 4, in which the tri-n-butyl antimony is replaced by triphenyl antimony, after being heated at 180 C. for 16 hours gives the following yields based upon added tin: di-n-bu-tyl tin dichloride 53.8%, n-butyl tin trichloride 19.6% and tri-n-butyl tin chloride nil.
- EXAMPLE 7 A mixture of: G. Tin 6.0 n-Octyl bromide 24.9 n-Octyl iodide 2.0
- EXAMPLE 9 A mixture of: G. Tin (shavings of 0.1-0.3 mm.) 6.0 n-Octyl bromide 58.0
- the autoclave is introduced after the air in the autoclave has been replaced by nitrogen.
- the autoclave is next heated at 175 C. for three hours, whilst the stirrer is rotated at a velocity of 480 rotations/min. During the reaction the pressure rises to approx. 9 kg./cm.
- organo-antimony compound catalyst is present in an amount of from 3 mol percent to 5 mol percent.
- organo-antimony compound catalyst contains only alkyl or cycloalkyl groups corresponding to said organic halides selected from the group consisting of alkyl halides and cycloalkyl halides.
- part of said organoantimony compound catalyst is the antimony-containing distillation residues from a previous reaction.
- a process for the production of n-butyl tin chlorides which consists essentially of reacting metallic tin with n-butyl chloride in a molecular ratio of 1:2 to 1:3 in the presence of from 3 mol percent to 5 mol percent, based on the amount of tin, of tri-n-butyl antimony and in the presence of from 0.5 mol percent to 10 mol percent, calculated on the amount of n -butyl chloride, of n-butyl iodide, at a temperature of between. 160 C. and 180 C and recovering said n-butyl tin chlorides.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL676709983A NL154742B (nl) | 1967-07-18 | 1967-07-18 | Werkwijze voor het bereiden van alkyl- of cycloalkyltinhalogeniden. |
| DE19681768914 DE1768914C (de) | 1967-07-18 | 1968-07-12 | Verfahren zur Herstellung von Alkyl oder Cycloalkylzinnhalogeniden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3595892A true US3595892A (en) | 1971-07-27 |
Family
ID=25755514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US744701A Expired - Lifetime US3595892A (en) | 1967-07-18 | 1968-07-15 | Process for the production of alkylor cycloalkyl tin halides |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3595892A (enrdf_load_stackoverflow) |
| BE (1) | BE718175A (enrdf_load_stackoverflow) |
| BR (1) | BR6800602D0 (enrdf_load_stackoverflow) |
| CH (1) | CH501673A (enrdf_load_stackoverflow) |
| FR (1) | FR1579116A (enrdf_load_stackoverflow) |
| GB (1) | GB1228810A (enrdf_load_stackoverflow) |
| NL (1) | NL154742B (enrdf_load_stackoverflow) |
| SE (1) | SE354283B (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3971817A (en) * | 1973-08-16 | 1976-07-27 | Ciba-Geigy Corporation | Process for the manufacture of monomethyl-tin trichloride |
| US20090131704A1 (en) * | 2005-07-12 | 2009-05-21 | Arkema Vlissingen | Process for the Preparation of Monoalkyltin Trihalides and Dialkyltin Dihalides |
| US20220332735A1 (en) * | 2021-04-13 | 2022-10-20 | Bnt Chemicals Gmbh | Method for cleaving alkyl tin halides |
-
1967
- 1967-07-18 NL NL676709983A patent/NL154742B/xx not_active IP Right Cessation
-
1968
- 1968-07-11 FR FR1579116D patent/FR1579116A/fr not_active Expired
- 1968-07-12 BR BR200602/68A patent/BR6800602D0/pt unknown
- 1968-07-15 US US744701A patent/US3595892A/en not_active Expired - Lifetime
- 1968-07-15 SE SE09703/68A patent/SE354283B/xx unknown
- 1968-07-15 CH CH1053668A patent/CH501673A/de not_active IP Right Cessation
- 1968-07-16 GB GB1228810D patent/GB1228810A/en not_active Expired
- 1968-07-17 BE BE718175D patent/BE718175A/xx unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3971817A (en) * | 1973-08-16 | 1976-07-27 | Ciba-Geigy Corporation | Process for the manufacture of monomethyl-tin trichloride |
| US20090131704A1 (en) * | 2005-07-12 | 2009-05-21 | Arkema Vlissingen | Process for the Preparation of Monoalkyltin Trihalides and Dialkyltin Dihalides |
| US7592472B2 (en) * | 2005-07-12 | 2009-09-22 | Arkema Vlissingen | Process for the preparation of monoalkyltin trihalides and dialkyltin dihalides |
| US20220332735A1 (en) * | 2021-04-13 | 2022-10-20 | Bnt Chemicals Gmbh | Method for cleaving alkyl tin halides |
| US11912732B2 (en) * | 2021-04-13 | 2024-02-27 | Bnt Chemicals Gmbh | Method for cleaving alkyl tin halides |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1579116A (enrdf_load_stackoverflow) | 1969-08-22 |
| BE718175A (enrdf_load_stackoverflow) | 1968-12-31 |
| SE354283B (enrdf_load_stackoverflow) | 1973-03-05 |
| CH501673A (de) | 1971-01-15 |
| GB1228810A (enrdf_load_stackoverflow) | 1971-04-21 |
| DE1768914A1 (de) | 1971-10-07 |
| NL154742B (nl) | 1977-10-17 |
| NL6709983A (enrdf_load_stackoverflow) | 1969-01-21 |
| BR6800602D0 (pt) | 1973-01-11 |
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