CA1125780A - Methode pour l'obtention d'alpha-omega- diacyloxysiloxanes - Google Patents

Methode pour l'obtention d'alpha-omega- diacyloxysiloxanes

Info

Publication number: CA1125780A
Authority: CA; Canada
Prior art keywords: omega; groups; acid; diacyloxysiloxanes; alpha
Prior art date: 1977-10-28
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

CA360,251A

Other languages

English (en)

Inventor

Eugene R. Martin

Richard N. Lewis

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.)

Wacker Chemical Corp

Original Assignee

Wacker Chemical 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.)

1977-10-28

Filing date

1980-09-15

Publication date

1982-06-15

1977-10-28 Priority claimed from CA289,796A external-priority patent/CA1115726A/fr

1980-09-15 Application filed by Wacker Chemical Corp filed Critical Wacker Chemical Corp

1980-09-15 Priority to CA360,251A priority Critical patent/CA1125780A/fr

1982-06-15 Application granted granted Critical

1982-06-15 Publication of CA1125780A publication Critical patent/CA1125780A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 15
239000002253 acid Substances 0.000 claims abstract description 14
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 8
239000004927 clay Substances 0.000 claims abstract description 7
238000011067 equilibration Methods 0.000 claims abstract description 7
150000008065 acid anhydrides Chemical class 0.000 claims abstract description 6
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 6
238000010438 heat treatment Methods 0.000 claims abstract description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 4
229920002554 vinyl polymer Polymers 0.000 claims abstract description 4
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 3
229930195733 hydrocarbon Natural products 0.000 claims abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
-1 cyclic siloxanes Chemical class 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 abstract description 4
229920002379 silicone rubber Polymers 0.000 abstract description 3
239000004945 silicone rubber Substances 0.000 abstract description 3
239000007864 aqueous solution Substances 0.000 abstract description 2
239000012530 fluid Substances 0.000 abstract description 2
238000004519 manufacturing process Methods 0.000 abstract 1
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
230000007062 hydrolysis Effects 0.000 description 10
238000006460 hydrolysis reaction Methods 0.000 description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
238000009833 condensation Methods 0.000 description 6
230000005494 condensation Effects 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 5
239000000463 material Substances 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229960001407 sodium bicarbonate Drugs 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
235000017550 sodium carbonate Nutrition 0.000 description 5
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
125000004423 acyloxy group Chemical group 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000003054 catalyst Substances 0.000 description 3
LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
229910000077 silane Inorganic materials 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
IDXCKOANSQIPGX-UHFFFAOYSA-N (acetyloxy-ethenyl-methylsilyl) acetate Chemical compound CC(=O)O[Si](C)(C=C)OC(C)=O IDXCKOANSQIPGX-UHFFFAOYSA-N 0.000 description 1
AWFOOUAPWFZKQK-UHFFFAOYSA-N (acetyloxy-methyl-phenylsilyl) acetate Chemical compound CC(=O)O[Si](C)(OC(C)=O)C1=CC=CC=C1 AWFOOUAPWFZKQK-UHFFFAOYSA-N 0.000 description 1
VMAWODUEPLAHOE-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 VMAWODUEPLAHOE-UHFFFAOYSA-N 0.000 description 1
LTIUDPOSFOYSKA-UHFFFAOYSA-N 2-ethenyl-2,4,4,6,6,8,8-heptamethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C=C)O[Si](C)(C)O1 LTIUDPOSFOYSKA-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
238000012935 Averaging Methods 0.000 description 1
RQVFGTYFBUVGOP-UHFFFAOYSA-N [acetyloxy(dimethyl)silyl] acetate Chemical compound CC(=O)O[Si](C)(C)OC(C)=O RQVFGTYFBUVGOP-UHFFFAOYSA-N 0.000 description 1
CNOSLBKTVBFPBB-UHFFFAOYSA-N [acetyloxy(diphenyl)silyl] acetate Chemical compound C=1C=CC=CC=1[Si](OC(C)=O)(OC(=O)C)C1=CC=CC=C1 CNOSLBKTVBFPBB-UHFFFAOYSA-N 0.000 description 1
PGYGJYORWXDDMZ-UHFFFAOYSA-N [dihydroxy(methyl)silyl]oxy-[[dimethyl(trimethylsilyloxy)silyl]oxy-dimethylsilyl]oxy-dimethylsilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(O)O PGYGJYORWXDDMZ-UHFFFAOYSA-N 0.000 description 1
WDRCWISGZGOZPY-UHFFFAOYSA-N [dihydroxy(methyl)silyl]oxy-[dimethyl(trimethylsilyloxy)silyl]oxy-dimethylsilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(O)O WDRCWISGZGOZPY-UHFFFAOYSA-N 0.000 description 1
QLTIQRMARFXIDD-UHFFFAOYSA-N [dihydroxy(methyl)silyl]oxy-dimethyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(O)O QLTIQRMARFXIDD-UHFFFAOYSA-N 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 1
YLJJAVFOBDSYAN-UHFFFAOYSA-N dichloro-ethenyl-methylsilane Chemical compound C[Si](Cl)(Cl)C=C YLJJAVFOBDSYAN-UHFFFAOYSA-N 0.000 description 1
GNEPOXWQWFSSOU-UHFFFAOYSA-N dichloro-methyl-phenylsilane Chemical compound C[Si](Cl)(Cl)C1=CC=CC=C1 GNEPOXWQWFSSOU-UHFFFAOYSA-N 0.000 description 1
OLLFKUHHDPMQFR-UHFFFAOYSA-N dihydroxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](O)(O)C1=CC=CC=C1 OLLFKUHHDPMQFR-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000004756 silanes Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000031 sodium sesquicarbonate Inorganic materials 0.000 description 1
235000018341 sodium sesquicarbonate Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
WCTAGTRAWPDFQO-UHFFFAOYSA-K trisodium;hydrogen carbonate;carbonate Chemical compound [Na+].[Na+].[Na+].OC([O-])=O.[O-]C([O-])=O WCTAGTRAWPDFQO-UHFFFAOYSA-K 0.000 description 1

Landscapes

Silicon Polymers (AREA)

CA360,251A 1977-10-28 1980-09-15 Methode pour l'obtention d'alpha-omega- diacyloxysiloxanes Expired CA1125780A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA360,251A CA1125780A (fr)	1977-10-28	1980-09-15	Methode pour l'obtention d'alpha-omega- diacyloxysiloxanes

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CA289,796A CA1115726A (fr)	1977-10-28	1977-10-28	Procede d'obtention d'alpha, omega-siloxanediols
CA360,251A CA1125780A (fr)	1977-10-28	1980-09-15	Methode pour l'obtention d'alpha-omega- diacyloxysiloxanes

Publications (1)

Publication Number	Publication Date
CA1125780A true CA1125780A (fr)	1982-06-15

Family

ID=25668594

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA360,251A Expired CA1125780A (fr)	1977-10-28	1980-09-15	Methode pour l'obtention d'alpha-omega- diacyloxysiloxanes

Country Status (1)

Country	Link
CA (1)	CA1125780A (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN111690138A (zh) *	2020-07-16	2020-09-22	江西蓝星星火有机硅有限公司	低粘度乙烯基羟基硅油及其制备方法
CN112010888A (zh) *	2019-05-28	2020-12-01	赢创运营有限公司	制备带乙酰氧基的硅氧烷的方法
CN112011054A (zh) *	2019-05-28	2020-12-01	赢创运营有限公司	乙酰氧基体系
CN112010887A (zh) *	2019-05-28	2020-12-01	赢创运营有限公司	制备带乙酰氧基的硅氧烷的方法
EP3744753A1 (fr) *	2019-05-28	2020-12-02	Evonik Operations GmbH	Procédé de purification d'acétoxysiloxanes
CN113754888A (zh) *	2020-06-02	2021-12-07	赢创运营有限公司	线性含乙酰氧基的硅氧烷及派生产物
CN114430757A (zh) *	2019-09-27	2022-05-03	赢创运营有限公司	硅酮(甲基)丙烯酸酯、其制备方法及其在可固化组合物中的用途
US11795275B2 (en)	2018-12-04	2023-10-24	Evonik Operations Gmbh	Reactive siloxanes

1980
- 1980-09-15 CA CA360,251A patent/CA1125780A/fr not_active Expired

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US11795275B2 (en)	2018-12-04	2023-10-24	Evonik Operations Gmbh	Reactive siloxanes
US11066429B2 (en)	2019-05-28	2021-07-20	Evonik Operations Gmbh	Process for producing acetoxy-bearing siloxanes
US11286351B2 (en)	2019-05-28	2022-03-29	Evonik Operations Gmbh	Process for producing acetoxy-bearing siloxanes
CN112010887A (zh) *	2019-05-28	2020-12-01	赢创运营有限公司	制备带乙酰氧基的硅氧烷的方法
EP3744755A1 (fr) *	2019-05-28	2020-12-02	Evonik Operations GmbH	Procédé de production de siloxanes portant des groupes acétoxy
EP3744753A1 (fr) *	2019-05-28	2020-12-02	Evonik Operations GmbH	Procédé de purification d'acétoxysiloxanes
EP3744754A1 (fr) *	2019-05-28	2020-12-02	Evonik Operations GmbH	Procédé de production de siloxanes portant des groupes acétoxy
CN112011054A (zh) *	2019-05-28	2020-12-01	赢创运营有限公司	乙酰氧基体系
CN112010888A (zh) *	2019-05-28	2020-12-01	赢创运营有限公司	制备带乙酰氧基的硅氧烷的方法
CN112011054B (zh) *	2019-05-28	2023-09-29	赢创运营有限公司	乙酰氧基体系
US11472822B2 (en)	2019-05-28	2022-10-18	Evonik Operations Gmbh	Process for purifying acetoxysiloxanes
EP3744756A1 (fr) *	2019-05-28	2020-12-02	Evonik Operations GmbH	Systèmes acétoxy
US11420985B2 (en)	2019-05-28	2022-08-23	Evonik Operations Gmbh	Acetoxy systems
CN114430757A (zh) *	2019-09-27	2022-05-03	赢创运营有限公司	硅酮(甲基)丙烯酸酯、其制备方法及其在可固化组合物中的用途
CN113754888A (zh) *	2020-06-02	2021-12-07	赢创运营有限公司	线性含乙酰氧基的硅氧烷及派生产物
EP3919550A1 (fr) *	2020-06-02	2021-12-08	Evonik Operations GmbH	Siloxanes linéaires transportant des groupes acetoxy et produits dérivés
CN111690138A (zh) *	2020-07-16	2020-09-22	江西蓝星星火有机硅有限公司	低粘度乙烯基羟基硅油及其制备方法

Legal Events

Date	Code	Title	Description
1999-06-15	MKEX	Expiry

Publication	Publication Date	Title
US4066680A (en)	1978-01-03	Process for making alpha,omega-siloxanediols
US4029629A (en)	1977-06-14	Solvent resistant room temperature vulcanizable silicone rubber composition
US5162480A (en)	1992-11-10	Self-curing ceramicizable polysiloxanes
US5220033A (en)	1993-06-15	Siloxane compounds and their preparation
US4529752A (en)	1985-07-16	Solvent resistant vulcanizable silicone rubber composition
US5446185A (en)	1995-08-29	Alkylhydrido siloxanes
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US4260715A (en)	1981-04-07	Process for the production of siliconfunctional polyorganosiloxanes
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US20030144449A1 (en)	2003-07-31	Preparation of linear organosiloxane polymers
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US3992426A (en)	1976-11-16	Quadripolymer siloxanes containing Si-H bonds
US4933413A (en)	1990-06-12	Process for synthesis of acylamino organosilicon compounds
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