CA1304757C - Process for the production of polyglycerines - Google Patents
Process for the production of polyglycerinesInfo
- Publication number
- CA1304757C CA1304757C CA000594196A CA594196A CA1304757C CA 1304757 C CA1304757 C CA 1304757C CA 000594196 A CA000594196 A CA 000594196A CA 594196 A CA594196 A CA 594196A CA 1304757 C CA1304757 C CA 1304757C
- Authority
- CA
- Canada
- Prior art keywords
- mixture
- glycerols
- solution
- glycerol
- temperature
- 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
- 238000000034 method Methods 0.000 title claims abstract description 39
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 78
- 239000000203 mixture Substances 0.000 claims abstract description 37
- 229920000223 polyglycerol Polymers 0.000 claims abstract description 34
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims abstract description 24
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 11
- 239000011541 reaction mixture Substances 0.000 claims abstract description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000460 chlorine Substances 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 claims abstract description 7
- 238000004821 distillation Methods 0.000 claims abstract description 3
- 238000004508 fractional distillation Methods 0.000 claims abstract description 3
- 235000011187 glycerol Nutrition 0.000 claims description 45
- 150000002314 glycerols Chemical class 0.000 claims description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 230000008929 regeneration Effects 0.000 claims description 8
- 238000011069 regeneration method Methods 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 3
- 238000011033 desalting Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000004438 BET method Methods 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims 5
- 229920005989 resin Polymers 0.000 claims 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 239000003957 anion exchange resin Substances 0.000 claims 2
- 239000003729 cation exchange resin Substances 0.000 claims 2
- 125000000129 anionic group Chemical group 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 108091006522 Anion exchangers Proteins 0.000 abstract description 10
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 238000012958 reprocessing Methods 0.000 abstract description 2
- 150000003945 chlorohydrins Chemical class 0.000 abstract 1
- 150000001923 cyclic compounds Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- JYKSTGLAIMQDRA-UHFFFAOYSA-N tetraglycerol Chemical compound OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO JYKSTGLAIMQDRA-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 1
- -1 aliphatic alcohols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- 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
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/04—Processes using organic exchangers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
- C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3809882A DE3809882A1 (de) | 1988-03-24 | 1988-03-24 | Verfahren zur herstellung von polyglycerinen |
| DEP.3809882.2 | 1988-03-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1304757C true CA1304757C (en) | 1992-07-07 |
Family
ID=6350540
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000594196A Expired - Lifetime CA1304757C (en) | 1988-03-24 | 1989-03-20 | Process for the production of polyglycerines |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4960953A (enExample) |
| EP (1) | EP0333984B1 (enExample) |
| JP (1) | JP2786235B2 (enExample) |
| KR (1) | KR960008647B1 (enExample) |
| AT (1) | ATE87898T1 (enExample) |
| AU (1) | AU608136B2 (enExample) |
| CA (1) | CA1304757C (enExample) |
| DE (2) | DE3809882A1 (enExample) |
| ES (1) | ES2053823T3 (enExample) |
| GR (1) | GR3008142T3 (enExample) |
| IL (1) | IL89692A (enExample) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3842692A1 (de) * | 1988-12-19 | 1990-06-21 | Solvay Werke Gmbh | Verfahren zur herstellung von polyglycerinen |
| CA2063214A1 (en) * | 1991-03-19 | 1992-09-20 | George C. Blytas | Method of preparing polyethercyclicpolyols |
| US5198532A (en) * | 1991-03-19 | 1993-03-30 | Shell Oil Company | Polycondensation of epihalohydrin and polyhydric alcohols and thermal condensation to form polyethercyclicpolyols |
| US5302728A (en) * | 1991-03-19 | 1994-04-12 | Shell Oil Company | Polycondensation of phenolic hydroxyl-containing compounds and polyhydric alcohols and thermal condensation to form polyethercyclipolyols |
| US5302695A (en) * | 1991-03-19 | 1994-04-12 | Shell Oil Company | Polycondensation of epoxy alcohols with polyhydric alcohols and thermal condensation to form polyethercyclicpolyols |
| US5233055A (en) * | 1991-03-19 | 1993-08-03 | Shell Oil Company | Copolymerization of polyethercyclicpolyols with epoxy resins |
| US5338870A (en) * | 1991-03-19 | 1994-08-16 | Shell Oil Company | Thermal condensation of polyhydric alcohols to form polyethercyclicpolyols |
| US5371244A (en) * | 1991-03-19 | 1994-12-06 | Shell Oil Company | Polycondensation of dihydric alcohols and polyhydric alcohols and thermal condensation to form polyethercyclicpolyols |
| US5204444A (en) * | 1991-03-19 | 1993-04-20 | Shell Oil Company | Polycondensation of epoxy alcohols with polyhdric alcohols and thermal condensation to form polyethercyclicpolyols |
| DE4132171A1 (de) * | 1991-09-27 | 1993-04-01 | Solvay Werke Gmbh | Verfahren zur herstellung von diglycerin und/oder polyglycerin |
| US5349094A (en) * | 1992-06-12 | 1994-09-20 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of oligoglycerol mixtures of increased diglycerol content |
| DE4228147A1 (de) * | 1992-08-25 | 1994-03-03 | Solvay Fluor & Derivate | Verfahren und Vorrichtung zur Herstellung von Diglycerin |
| US5371243A (en) * | 1992-10-13 | 1994-12-06 | Shell Oil Company | Polyethercyclicpolyols from epihalohydrins, polyhydric alcohols, and metal hydroxides |
| US5428178A (en) * | 1992-10-13 | 1995-06-27 | Shell Oil Company | Polyethercyclipolyols from epihalohydrins, polyhydric alcohols, and metal hydroxides or epoxy alcohols and optionally polyhydric alcohols with thermal condensation |
| US5286882A (en) * | 1992-10-13 | 1994-02-15 | Shell Oil Company | Polyethercyclicpolyols from epihalohydrins, polyhydric alcohols and metal hydroxides or epoxy alcohol and optionally polyhydric alcohols with addition of epoxy resins |
| US5579769A (en) * | 1992-12-02 | 1996-12-03 | Shiseido Company, Ltd. | Coupling medium for probe of ultrasonograph |
| US6620904B2 (en) | 2000-11-06 | 2003-09-16 | Lonza Inc. | Processes for preparing linear polyglycerols and polyglycerol esters |
| US6770264B2 (en) * | 2001-11-13 | 2004-08-03 | Noville, Inc. | Chewing gum compositions comprising diglycerol |
| US6723304B2 (en) | 2001-11-13 | 2004-04-20 | Noville, Inc. | Oral care compositions comprising diglycerol |
| KR100877445B1 (ko) * | 2003-11-20 | 2009-01-09 | 솔베이(소시에떼아노님) | 에폭시 수지의 제조 방법 |
| EP2253609A1 (en) * | 2003-11-20 | 2010-11-24 | SOLVAY (Société Anonyme) | Process for producing organic compounds from glycerol, the glycerol coming from renewable raw material |
| KR20080037613A (ko) | 2005-05-20 | 2008-04-30 | 솔베이(소시에떼아노님) | 폴리히드록실화 지방족 탄화수소의 클로로히드린으로의전환 방법 |
| EP1885676A2 (fr) * | 2005-05-20 | 2008-02-13 | Solvay SA | Procede de conversion d'hydrocarbures aliphatiques poly hydroxyles en chlorhydrines |
| MY142392A (en) | 2005-10-26 | 2010-11-30 | Malaysian Palm Oil Board | A process for preparing polymers of polyhydric alcohols |
| CN102219644B (zh) * | 2005-11-08 | 2013-11-06 | 索尔维公司 | 通过甘油的氯化制备二氯丙醇的方法 |
| EP2043984A1 (en) * | 2006-06-14 | 2009-04-08 | Solvay S.A. | Crude glycerol-based product, process for its purification and its use in the manufacture of dichloropropanol |
| FR2913421B1 (fr) * | 2007-03-07 | 2009-05-15 | Solvay | Procede de fabrication de dichloropropanol. |
| FR2913684B1 (fr) * | 2007-03-14 | 2012-09-14 | Solvay | Procede de fabrication de dichloropropanol |
| TW200911740A (en) * | 2007-06-01 | 2009-03-16 | Solvay | Process for manufacturing a chlorohydrin |
| TW200911693A (en) | 2007-06-12 | 2009-03-16 | Solvay | Aqueous composition containing a salt, manufacturing process and use |
| TW200911773A (en) | 2007-06-12 | 2009-03-16 | Solvay | Epichlorohydrin, manufacturing process and use |
| CN101896262A (zh) * | 2007-10-02 | 2010-11-24 | 索尔维公司 | 含硅的组合物用于改进容器的抗腐蚀性的用途 |
| FR2925045B1 (fr) | 2007-12-17 | 2012-02-24 | Solvay | Produit a base de glycerol, procede pour son obtention et son utilisation dans la fabrication de dichloropropanol |
| TWI478875B (zh) | 2008-01-31 | 2015-04-01 | Solvay | 使水性組成物中之有機物質降解之方法 |
| TWI448449B (zh) * | 2008-04-03 | 2014-08-11 | Solvay | 含甘油的組成物、彼之製法及彼於製造二氯丙醇上的用途 |
| FR2935968B1 (fr) * | 2008-09-12 | 2010-09-10 | Solvay | Procede pour la purification de chlorure d'hydrogene |
| JP5502349B2 (ja) * | 2009-03-13 | 2014-05-28 | 出光興産株式会社 | 水系潤滑剤 |
| US8101045B2 (en) * | 2010-01-05 | 2012-01-24 | Nalco Company | Modifying agent for yankee coatings |
| JP6049087B2 (ja) | 2010-09-30 | 2016-12-21 | ソルヴェイ（ソシエテ アノニム） | 天然起源のエピクロロヒドリンの誘導体 |
| JP2019523311A (ja) | 2016-05-20 | 2019-08-22 | ステパン カンパニー | 洗濯洗剤のためのポリエーテルアミン組成物 |
| WO2018140447A1 (en) * | 2017-01-24 | 2018-08-02 | Cargill, Incorporated | Polyglycerol compositions |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE510422C (de) * | 1925-12-19 | 1930-10-18 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von Oxalkylaethern des Glycerins |
| US2520670A (en) * | 1946-10-24 | 1950-08-29 | Gen Mills Inc | Polyglycerols |
| US4053525A (en) * | 1976-11-01 | 1977-10-11 | Shell Oil Company | Process for production of glycerine |
| DE3410520A1 (de) * | 1984-03-22 | 1985-09-26 | Deutsche Solvay-Werke Gmbh, 5650 Solingen | Verfahren zur herstellung von polyglycerinen durch reinigung und trennung einer waessrigen loesung eines polyglycerinhaltigen produktes |
-
1988
- 1988-03-24 DE DE3809882A patent/DE3809882A1/de not_active Withdrawn
-
1989
- 1989-01-17 ES ES89100700T patent/ES2053823T3/es not_active Expired - Lifetime
- 1989-01-17 EP EP89100700A patent/EP0333984B1/de not_active Expired - Lifetime
- 1989-01-17 DE DE8989100700T patent/DE58903995D1/de not_active Expired - Lifetime
- 1989-01-17 AT AT89100700T patent/ATE87898T1/de not_active IP Right Cessation
- 1989-03-08 KR KR89002863A patent/KR960008647B1/ko not_active Expired - Fee Related
- 1989-03-20 CA CA000594196A patent/CA1304757C/en not_active Expired - Lifetime
- 1989-03-21 IL IL89692A patent/IL89692A/xx unknown
- 1989-03-22 AU AU31624/89A patent/AU608136B2/en not_active Expired
- 1989-03-23 JP JP1069430A patent/JP2786235B2/ja not_active Expired - Lifetime
- 1989-03-24 US US07/328,316 patent/US4960953A/en not_active Expired - Lifetime
-
1993
- 1993-06-15 GR GR920403221T patent/GR3008142T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0333984A2 (de) | 1989-09-27 |
| AU608136B2 (en) | 1991-03-21 |
| JP2786235B2 (ja) | 1998-08-13 |
| IL89692A0 (en) | 1989-09-28 |
| KR890014419A (ko) | 1989-10-23 |
| DE3809882A1 (de) | 1989-10-05 |
| ATE87898T1 (de) | 1993-04-15 |
| KR960008647B1 (en) | 1996-06-28 |
| EP0333984A3 (en) | 1990-06-13 |
| ES2053823T3 (es) | 1994-08-01 |
| DE58903995D1 (de) | 1993-05-13 |
| EP0333984B1 (de) | 1993-04-07 |
| AU3162489A (en) | 1989-09-28 |
| IL89692A (en) | 1993-02-21 |
| GR3008142T3 (enExample) | 1993-09-30 |
| US4960953A (en) | 1990-10-02 |
| JPH01283246A (ja) | 1989-11-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |