GB1355704A - Process for the dehydration of diols - Google Patents
Process for the dehydration of diolsInfo
- Publication number
- GB1355704A GB1355704A GB2724471*A GB2724471A GB1355704A GB 1355704 A GB1355704 A GB 1355704A GB 2724471 A GB2724471 A GB 2724471A GB 1355704 A GB1355704 A GB 1355704A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrophosphate
- sodium
- lithium
- prepared
- barium
- 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
- 230000018044 dehydration Effects 0.000 title abstract 3
- 238000006297 dehydration reaction Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 150000002009 diols Chemical class 0.000 title abstract 2
- 235000011180 diphosphates Nutrition 0.000 abstract 10
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 abstract 9
- 239000002244 precipitate Substances 0.000 abstract 9
- 229940048084 pyrophosphate Drugs 0.000 abstract 9
- 239000000243 solution Substances 0.000 abstract 7
- 238000001354 calcination Methods 0.000 abstract 5
- 238000001035 drying Methods 0.000 abstract 5
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 abstract 4
- VVNXEADCOVSAER-UHFFFAOYSA-N lithium sodium Chemical compound [Li].[Na] VVNXEADCOVSAER-UHFFFAOYSA-N 0.000 abstract 4
- 229910052751 metal Inorganic materials 0.000 abstract 4
- 239000002184 metal Substances 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 abstract 3
- 238000009835 boiling Methods 0.000 abstract 3
- 230000007935 neutral effect Effects 0.000 abstract 3
- 239000011734 sodium Substances 0.000 abstract 3
- VZWGHDYJGOMEKT-UHFFFAOYSA-J sodium pyrophosphate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O VZWGHDYJGOMEKT-UHFFFAOYSA-J 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 229910052788 barium Inorganic materials 0.000 abstract 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 2
- IWOUKMZUPDVPGQ-UHFFFAOYSA-N barium nitrate Chemical compound [Ba+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O IWOUKMZUPDVPGQ-UHFFFAOYSA-N 0.000 abstract 2
- RCUAPGYXYWSYKO-UHFFFAOYSA-J barium(2+);phosphonato phosphate Chemical compound [Ba+2].[Ba+2].[O-]P([O-])(=O)OP([O-])([O-])=O RCUAPGYXYWSYKO-UHFFFAOYSA-J 0.000 abstract 2
- 229910052744 lithium Inorganic materials 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical class [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 abstract 2
- 229910052712 strontium Inorganic materials 0.000 abstract 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 abstract 2
- DHEQXMRUPNDRPG-UHFFFAOYSA-N strontium nitrate Chemical compound [Sr+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O DHEQXMRUPNDRPG-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 abstract 1
- 229910002651 NO3 Inorganic materials 0.000 abstract 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 1
- KWVFUTDPKIKVQW-UHFFFAOYSA-N [Sr].[Na] Chemical compound [Sr].[Na] KWVFUTDPKIKVQW-UHFFFAOYSA-N 0.000 abstract 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- LYSTYSFIGYAXTG-UHFFFAOYSA-L barium(2+);hydrogen phosphate Chemical compound [Ba+2].OP([O-])([O-])=O LYSTYSFIGYAXTG-UHFFFAOYSA-L 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000002091 cationic group Chemical group 0.000 abstract 1
- -1 cationic metals Chemical class 0.000 abstract 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 abstract 1
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 abstract 1
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229940048086 sodium pyrophosphate Drugs 0.000 abstract 1
- MVGWWCXDTHXKTR-UHFFFAOYSA-J tetralithium;phosphonato phosphate Chemical compound [Li+].[Li+].[Li+].[Li+].[O-]P([O-])(=O)OP([O-])([O-])=O MVGWWCXDTHXKTR-UHFFFAOYSA-J 0.000 abstract 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 abstract 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 abstract 1
- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by elimination of -OH groups, e.g. by dehydration
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
- B01J27/18—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr with metals other than Al or Zr
- B01J27/1802—Salts or mixtures of anhydrides with compounds of other metals than V, Nb, Ta, Cr, Mo, W, Mn, Tc, Re, e.g. phosphates, thiophosphates
- B01J27/1806—Salts or mixtures of anhydrides with compounds of other metals than V, Nb, Ta, Cr, Mo, W, Mn, Tc, Re, e.g. phosphates, thiophosphates with alkaline or alkaline earth metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/14—Phosphorus; Compounds thereof
- C07C2527/16—Phosphorus; Compounds thereof containing oxygen
- C07C2527/167—Phosphates or other compounds comprising the anion (PnO3n+1)(n+2)-
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S585/00—Chemistry of hydrocarbon compounds
- Y10S585/8995—Catalyst and recycle considerations
- Y10S585/906—Catalyst preservation or manufacture, e.g. activation before use
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7013791A FR2087011A5 (enExample) | 1970-04-16 | 1970-04-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1355704A true GB1355704A (en) | 1974-06-05 |
Family
ID=9054073
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2724471*A Expired GB1355704A (en) | 1970-04-16 | 1971-04-19 | Process for the dehydration of diols |
| GB5805373A Expired GB1355705A (en) | 1970-04-16 | 1971-04-19 | Process for preparing dehydration catalysts suitable for use in the dehydration of diols |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5805373A Expired GB1355705A (en) | 1970-04-16 | 1971-04-19 | Process for preparing dehydration catalysts suitable for use in the dehydration of diols |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3781222A (enExample) |
| JP (1) | JPS549148B1 (enExample) |
| AT (2) | AT313861B (enExample) |
| BE (1) | BE765090A (enExample) |
| CA (1) | CA975383A (enExample) |
| CS (1) | CS161903B2 (enExample) |
| DE (1) | DE2117444C3 (enExample) |
| FR (1) | FR2087011A5 (enExample) |
| GB (2) | GB1355704A (enExample) |
| LU (1) | LU62940A1 (enExample) |
| NL (1) | NL157883B (enExample) |
| RO (1) | RO57596A (enExample) |
| SE (1) | SE372512B (enExample) |
| SU (2) | SU555832A3 (enExample) |
| ZA (1) | ZA712362B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0015318A1 (de) * | 1979-02-07 | 1980-09-17 | Chemische Werke Hüls Ag | Verfahren zur Herstellung von reinen alpha,omega-C6-bis C20-Alkenolen |
| EP0195943A3 (en) * | 1985-03-23 | 1988-03-23 | Huls Aktiengesellschaft | Catalytic system and process for the preparation of alpha-omega c4 to c20 alkenols |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3957900A (en) * | 1970-04-16 | 1976-05-18 | Compagnie Francaise De Raffinage | Method for the dehydration of diols |
| US3862964A (en) * | 1971-04-09 | 1975-01-28 | Raffinage Cie Francaise | Dehydration catalysts, particularly for the dehydration of diols |
| US3957897A (en) * | 1974-05-28 | 1976-05-18 | The Dow Chemical Company | Method of oxydehydrogenation of alkyl aromatic compounds |
| US4081488A (en) | 1975-12-24 | 1978-03-28 | Fmc Corporation | Process for preparing 1,1-dihalo-4-methyl-1,3-pentadienes |
| JPS5940057B2 (ja) * | 1979-05-31 | 1984-09-27 | 日揮化学株式会社 | エタノ−ルからのエチレン製造用触媒 |
| RU2447049C1 (ru) * | 2010-12-30 | 2012-04-10 | Общество с ограниченной ответственностью "УНИСИТ" (ООО "УНИСИТ") | Способ переработки полупродуктов синтеза изопрена |
| RU2446138C1 (ru) * | 2010-12-30 | 2012-03-27 | Общество с ограниченной ответственностью "УНИСИТ" (ООО "УНИСИТ") | Способ получения изопрена |
| CN103998399B (zh) * | 2011-12-15 | 2016-08-24 | 陶氏环球技术有限责任公司 | 使用基于卤素的催化剂将连位化合物非还原性脱羟基为烯烃 |
| US20130274518A1 (en) | 2012-04-11 | 2013-10-17 | The Procter & Gamble Company | Purification Of Bio Based Acrylic Acid To Crude And Glacial Acrylic Acid |
| US9452967B2 (en) | 2012-04-11 | 2016-09-27 | The Procter & Gamble Company | Process for production of acrylic acid or its derivatives |
| US20130273384A1 (en) | 2012-04-11 | 2013-10-17 | The Procter & Gamble Company | Poly(Acrylic Acid) From Bio-Based Acrylic Acid And Its Derivatives |
| US20130274517A1 (en) | 2012-04-11 | 2013-10-17 | The Procter & Gamble Company | Process For Production Of Acrylic Acid Or Its Derivatives |
| JP5931781B2 (ja) * | 2013-03-11 | 2016-06-08 | 三井化学株式会社 | 共役ジエンの製造方法 |
| WO2015037580A1 (ja) * | 2013-09-12 | 2015-03-19 | 東レ株式会社 | ブタジエンの製造方法 |
| EP2952498A1 (en) | 2014-08-11 | 2015-12-09 | LANXESS Deutschland GmbH | Dehydration of 2,3-butanediole |
| KR101706449B1 (ko) * | 2015-04-01 | 2017-02-15 | 지에스칼텍스 주식회사 | 활성이 개선된 폴리나트륨인산염 담지 촉매 및 이를 이용하여 2,3-부탄디올로부터 메틸에틸케톤과 1,3-부타디엔을 제조하는 방법 |
| JP6574305B2 (ja) * | 2015-08-28 | 2019-09-11 | ザ プロクター アンド ギャンブル カンパニーＴｈｅ Ｐｒｏｃｔｅｒ ＆ Ｇａｍｂｌｅ Ｃｏｍｐａｎｙ | ヒドロキシプロピオン酸及びその誘導体の脱水用触媒 |
| BR112018004032B1 (pt) * | 2015-08-28 | 2021-09-21 | The Procter & Gamble Company | Catalisadores para a desidratação de ácido hidróxi propiônico e seus derivados |
| US10919030B2 (en) | 2016-09-30 | 2021-02-16 | Regents Of The University Of Minnesota | Forming dienes from cyclic ethers and diols, including tetrahydrofuran and 2-methyl-1,4-butanediol |
-
1970
- 1970-04-16 FR FR7013791A patent/FR2087011A5/fr not_active Expired
-
1971
- 1971-03-31 BE BE765090A patent/BE765090A/xx unknown
- 1971-04-06 LU LU62940D patent/LU62940A1/xx unknown
- 1971-04-08 DE DE2117444A patent/DE2117444C3/de not_active Expired
- 1971-04-09 US US00132892A patent/US3781222A/en not_active Expired - Lifetime
- 1971-04-09 CS CS2587A patent/CS161903B2/cs unknown
- 1971-04-14 AT AT316171A patent/AT313861B/de not_active IP Right Cessation
- 1971-04-14 AT AT395472A patent/AT318548B/de not_active IP Right Cessation
- 1971-04-14 CA CA110,313A patent/CA975383A/en not_active Expired
- 1971-04-14 ZA ZA712362A patent/ZA712362B/xx unknown
- 1971-04-15 SE SE7104912A patent/SE372512B/xx unknown
- 1971-04-15 SU SU1640619A patent/SU555832A3/ru active
- 1971-04-16 NL NL7105151.A patent/NL157883B/xx unknown
- 1971-04-16 RO RO66603A patent/RO57596A/ro unknown
- 1971-04-16 JP JP2396071A patent/JPS549148B1/ja active Pending
- 1971-04-19 GB GB2724471*A patent/GB1355704A/en not_active Expired
- 1971-04-19 GB GB5805373A patent/GB1355705A/en not_active Expired
-
1973
- 1973-08-20 SU SU1949761A patent/SU562191A3/ru active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0015318A1 (de) * | 1979-02-07 | 1980-09-17 | Chemische Werke Hüls Ag | Verfahren zur Herstellung von reinen alpha,omega-C6-bis C20-Alkenolen |
| US4250343A (en) * | 1979-02-07 | 1981-02-10 | Chemische Werke Huls Aktiengesellschaft | Process for the preparation of pure α,ω-C6 - to C20 -a |
| EP0195943A3 (en) * | 1985-03-23 | 1988-03-23 | Huls Aktiengesellschaft | Catalytic system and process for the preparation of alpha-omega c4 to c20 alkenols |
Also Published As
| Publication number | Publication date |
|---|---|
| AT318548B (de) | 1974-10-25 |
| US3781222A (en) | 1973-12-25 |
| SU562191A3 (ru) | 1977-06-15 |
| GB1355705A (en) | 1974-06-05 |
| DE2117444B2 (de) | 1977-07-28 |
| AT313861B (de) | 1974-03-11 |
| SU555832A3 (ru) | 1977-04-25 |
| FR2087011A5 (enExample) | 1971-12-31 |
| RO57596A (enExample) | 1975-04-15 |
| LU62940A1 (enExample) | 1971-08-26 |
| NL7105151A (enExample) | 1971-10-19 |
| DE2117444C3 (de) | 1978-03-23 |
| SE372512B (enExample) | 1974-12-23 |
| DE2117444A1 (de) | 1971-10-28 |
| CS161903B2 (enExample) | 1975-06-10 |
| ZA712362B (en) | 1972-01-26 |
| BE765090A (fr) | 1971-09-30 |
| CA975383A (en) | 1975-09-30 |
| JPS549148B1 (enExample) | 1979-04-21 |
| NL157883B (nl) | 1978-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |