CA1040644A - Synthese de composes de silazane - Google Patents

Synthese de composes de silazane

Info

Publication number: CA1040644A
Authority: CA; Canada
Prior art keywords: ammonia; diamine; halosilane; product; alkylene diamine
Prior art date: 1974-02-13
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

Application number

CA192,419A

Other languages

English (en)

Inventor

Frank D. Mendicino

George M. Omietanski

Robert P. Boersma

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Union Carbide Corp

Original Assignee

Union Carbide Corp

Priority date (The priority date 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 date listed.)

1974-02-13

Filing date

1974-02-13

Publication date

1978-10-17

1974-02-13 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1974-02-13 Priority to CA192,419A priority Critical patent/CA1040644A/fr

1978-10-17 Application granted granted Critical

1978-10-17 Publication of CA1040644A publication Critical patent/CA1040644A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 36
150000001875 compounds Chemical class 0.000 title claims abstract description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 83
229910021529 ammonia Inorganic materials 0.000 claims abstract description 48
125000005263 alkylenediamine group Chemical group 0.000 claims abstract description 26
238000006243 chemical reaction Methods 0.000 claims description 30
239000007788 liquid Substances 0.000 claims description 28
229910000039 hydrogen halide Inorganic materials 0.000 claims description 19
239000012433 hydrogen halide Substances 0.000 claims description 19
239000012071 phase Substances 0.000 claims description 19
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 13
239000007791 liquid phase Substances 0.000 claims description 11
125000002947 alkylene group Chemical group 0.000 claims description 9
238000000926 separation method Methods 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
AOZQTURTLIEFNQ-UHFFFAOYSA-N n,n'-bis(trimethylsilyl)ethane-1,2-diamine Chemical group C[Si](C)(C)NCCN[Si](C)(C)C AOZQTURTLIEFNQ-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical group C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical group CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
229920002554 vinyl polymer Polymers 0.000 claims description 2
239000005046 Chlorosilane Substances 0.000 claims 1
125000003916 ethylene diamine group Chemical group 0.000 claims 1
239000000047 product Substances 0.000 description 33
239000006227 byproduct Substances 0.000 description 22
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 9
238000013019 agitation Methods 0.000 description 9
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 8
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 8
229910000077 silane Inorganic materials 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
238000010908 decantation Methods 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
-1 alkoxy radicals Chemical class 0.000 description 5
230000008901 benefit Effects 0.000 description 5
HCFPRFJJTHMING-UHFFFAOYSA-N ethane-1,2-diamine;hydron;chloride Chemical class [Cl-].NCC[NH3+] HCFPRFJJTHMING-UHFFFAOYSA-N 0.000 description 5
239000005051 trimethylchlorosilane Substances 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
150000004985 diamines Chemical class 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000012808 vapor phase Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 3
238000011084 recovery Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
229910000069 nitrogen hydride Inorganic materials 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
238000013022 venting Methods 0.000 description 2
GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
229910007161 Si(CH3)3 Inorganic materials 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
ZZRGHKUNLAYDTC-UHFFFAOYSA-N ethoxy(methyl)silane Chemical compound CCO[SiH2]C ZZRGHKUNLAYDTC-UHFFFAOYSA-N 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
GFMUAWWLXMJVRV-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine;hydrochloride Chemical compound [Cl-].C[NH+](C)CCN GFMUAWWLXMJVRV-UHFFFAOYSA-N 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1

CA192,419A 1974-02-13 1974-02-13 Synthese de composes de silazane Expired CA1040644A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA192,419A CA1040644A (fr)	1974-02-13	1974-02-13	Synthese de composes de silazane

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA192,419A CA1040644A (fr)	1974-02-13	1974-02-13	Synthese de composes de silazane

Publications (1)

Publication Number	Publication Date
CA1040644A true CA1040644A (fr)	1978-10-17

Family

ID=4099177

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA192,419A Expired CA1040644A (fr)	1974-02-13	1974-02-13	Synthese de composes de silazane

Country Status (1)

Country	Link
CA (1)	CA1040644A (fr)

1974
- 1974-02-13 CA CA192,419A patent/CA1040644A/fr not_active Expired

Publication	Publication Date	Title
US3809713A (en)	1974-05-07	Process for producing silazane compounds
US4276424A (en)	1981-06-30	Methods for the production of organic polysilanes
EP1644387B1 (fr)	2008-05-14	Procede de preparation de silane thiocarboxylate
JPH01163187A (ja)	1989-06-27	高沸点残渣中のポリシラン類の再分配法
US2566363A (en)	1951-09-04	Tertiary alkoxy amino silanes
JPH0312073B2 (fr)	1991-02-19
US4032557A (en)	1977-06-28	Process for preparing organosiloxanes
US3099672A (en)	1963-07-30	Reduction of halogen-containing silicon compounds
DE69418783T2 (de)	1999-10-14	Umsetzung von hochsiedenden Rückständen der Direktsynthese aus Chlorsilanmonomere in Gegenwart von Chlor
US2566364A (en)	1951-09-04	Method for preparing organic polysilicates stable against hydrolysis
US2629727A (en)	1953-02-24	Organosilyl alcohols
US3755397A (en)	1973-08-28	Silylating agent
CA1040644A (fr)	1978-10-17	Synthese de composes de silazane
US2698861A (en)	1955-01-04	Method of preparing alkoxysilicon compounds
US3499020A (en)	1970-03-03	Reduction of substituted silanes
US4252569A (en)	1981-02-24	Process for preparing alkali metal siliconates
US5434286A (en)	1995-07-18	Process for the preparation of dimethylchlorosilane
JPS6011715B2 (ja)	1985-03-27	オルガノシロキサンの製造方法
US2626273A (en)	1953-01-20	Preparation of alkoxy hydrosilanes
US3358009A (en)	1967-12-12	Process for preparing mixed cyclic organosiloxanes
GB2204041A (en)	1988-11-02	Cyclic silethynyl polymers and a method for making them
US3009827A (en)	1961-11-21	Method of preparing silica pigment
US3334122A (en)	1967-08-01	Method of preparing arylsilanes
US4348532A (en)	1982-09-07	Monoorganosiloxy containing siloxane fluids
US4060536A (en)	1977-11-29	Method of preparing N,N'-bis-trimethylsilylurea