DE2937831C2 - - Google Patents
Info
- Publication number
- DE2937831C2 DE2937831C2 DE2937831A DE2937831A DE2937831C2 DE 2937831 C2 DE2937831 C2 DE 2937831C2 DE 2937831 A DE2937831 A DE 2937831A DE 2937831 A DE2937831 A DE 2937831A DE 2937831 C2 DE2937831 C2 DE 2937831C2
- Authority
- DE
- Germany
- Prior art keywords
- olefin
- formic acid
- diol
- hydrogen peroxide
- weight
- 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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 45
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 39
- 150000001336 alkenes Chemical class 0.000 claims description 36
- 150000002009 diols Chemical class 0.000 claims description 32
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 22
- 235000019253 formic acid Nutrition 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000007127 saponification reaction Methods 0.000 claims description 7
- 230000033444 hydroxylation Effects 0.000 claims description 5
- 238000005805 hydroxylation reaction Methods 0.000 claims description 5
- 150000004675 formic acid derivatives Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 238000005191 phase separation Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 150000000180 1,2-diols Chemical class 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DWANEFRJKWXRSG-UHFFFAOYSA-N 1,2-tetradecanediol Chemical compound CCCCCCCCCCCCC(O)CO DWANEFRJKWXRSG-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- -1 for example Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 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
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 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
- C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
-
- 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
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792937831 DE2937831A1 (de) | 1979-09-19 | 1979-09-19 | Herfahren zur hydroxylierung olefinisch ungesaettigter verbindungen |
| AU61446/80A AU534924B2 (en) | 1979-09-19 | 1980-08-14 | Hydroxylating olefinically unsaturated compounds |
| ES494319A ES494319A0 (es) | 1979-09-19 | 1980-08-18 | Procedimiento para la ludroxilacion de compuesto olefinica- mente insaturados |
| AT80105407T ATE1992T1 (de) | 1979-09-19 | 1980-09-10 | Verfahren zur hydroxylierung olefinisch ungesaettigter verbindungen. |
| EP80105407A EP0025940B1 (de) | 1979-09-19 | 1980-09-10 | Verfahren zur Hydroxylierung olefinisch ungesättigter Verbindungen |
| BR8005815A BR8005815A (pt) | 1979-09-19 | 1980-09-11 | Processo para a hidroxilacao de compostos olefinicos nao saturados |
| JP12807180A JPS5651427A (en) | 1979-09-19 | 1980-09-17 | Hydroxylation of olefinic unsaturated compound |
| CA000360467A CA1177095A (en) | 1979-09-19 | 1980-09-18 | Process for hydroxylating olefinically unsaturated compounds |
| AR22703382D AR227033A1 (es) | 1979-09-19 | 1982-01-01 | Procedimiento para hidroxilar compuestos olefinicos no saturados con 4 hasta 36 atomos de carbono |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792937831 DE2937831A1 (de) | 1979-09-19 | 1979-09-19 | Herfahren zur hydroxylierung olefinisch ungesaettigter verbindungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2937831A1 DE2937831A1 (de) | 1981-05-21 |
| DE2937831C2 true DE2937831C2 (en:Method) | 1989-04-27 |
Family
ID=6081252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792937831 Granted DE2937831A1 (de) | 1979-09-19 | 1979-09-19 | Herfahren zur hydroxylierung olefinisch ungesaettigter verbindungen |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0025940B1 (en:Method) |
| JP (1) | JPS5651427A (en:Method) |
| AR (1) | AR227033A1 (en:Method) |
| AT (1) | ATE1992T1 (en:Method) |
| AU (1) | AU534924B2 (en:Method) |
| BR (1) | BR8005815A (en:Method) |
| CA (1) | CA1177095A (en:Method) |
| DE (1) | DE2937831A1 (en:Method) |
| ES (1) | ES494319A0 (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3229084A1 (de) * | 1982-08-04 | 1984-02-09 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur herstellung von vicinalen diolen und deren formiaten |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2145076A (en) * | 1983-08-13 | 1985-03-20 | Ciba Geigy Ag | A process for producing 1,2-alkanediols |
| US4479021A (en) * | 1983-08-30 | 1984-10-23 | Ciba-Geigy Corporation | Continuous process for producing 1,2-alkanediols |
| MY144973A (en) * | 1998-09-29 | 2011-11-30 | Malaysian Palm Oil Board | Preparation of dihydroxy compound from unsaturated raw materials |
| MY142614A (en) | 2004-04-21 | 2010-12-15 | Malaysian Palm Oil Board | Palm-based hydroxy fatty acid |
| DE102004060541A1 (de) * | 2004-12-15 | 2006-06-29 | Degussa Ag | Verfahren zur Herstellung von Alkandiolen und Alkantriolen mit einer vicinalen Diol-Gruppe |
| CN113861013A (zh) * | 2021-11-10 | 2021-12-31 | 邢台德贵纳米材料科技有限公司 | 一种多羟基脂肪酸的制备及其在纳米碳酸钙包覆中的应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB634118A (en) * | 1942-02-09 | 1950-03-15 | Bataafsche Petroleum | A process for the catalytic hydroxylation of olefinic compounds |
| US2492201A (en) * | 1946-06-07 | 1949-12-27 | Swern Daniel | Hydroxylation process |
| FR1047126A (fr) * | 1951-12-27 | 1953-12-11 | Gustave Maubec Ets | Préparation de polyols gras à faible indice d'acide |
| DE956505C (de) * | 1953-01-18 | 1957-01-17 | Ruhrchemie Ag | Verfahren zur Herstellung von Tricyclo-(5, 2, 1, 0)-dekantriol-(3, 4, 8) bzw. -(3, 4, 9) |
| NL180307C (en:Method) * | 1978-10-13 | Ruhrchemie Ag |
-
1979
- 1979-09-19 DE DE19792937831 patent/DE2937831A1/de active Granted
-
1980
- 1980-08-14 AU AU61446/80A patent/AU534924B2/en not_active Ceased
- 1980-08-18 ES ES494319A patent/ES494319A0/es active Granted
- 1980-09-10 AT AT80105407T patent/ATE1992T1/de active
- 1980-09-10 EP EP80105407A patent/EP0025940B1/de not_active Expired
- 1980-09-11 BR BR8005815A patent/BR8005815A/pt unknown
- 1980-09-17 JP JP12807180A patent/JPS5651427A/ja active Granted
- 1980-09-18 CA CA000360467A patent/CA1177095A/en not_active Expired
-
1982
- 1982-01-01 AR AR22703382D patent/AR227033A1/es active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3229084A1 (de) * | 1982-08-04 | 1984-02-09 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur herstellung von vicinalen diolen und deren formiaten |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0224808B2 (en:Method) | 1990-05-30 |
| EP0025940B1 (de) | 1982-12-15 |
| AU6144680A (en) | 1981-03-26 |
| JPS5651427A (en) | 1981-05-09 |
| ES8104980A1 (es) | 1981-05-16 |
| AU534924B2 (en) | 1984-02-23 |
| ATE1992T1 (de) | 1982-12-15 |
| ES494319A0 (es) | 1981-05-16 |
| BR8005815A (pt) | 1981-03-24 |
| DE2937831A1 (de) | 1981-05-21 |
| AR227033A1 (es) | 1982-09-15 |
| CA1177095A (en) | 1984-10-30 |
| EP0025940A1 (de) | 1981-04-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE882987C (de) | Verfahren zur Herstellung von tert.-Alkylbenzolcarbonsaeuren | |
| EP0048804B1 (de) | Verfahren zur Herstellung von Cycloocten-4-ol-1 aus Cyclooctadien-1,5 | |
| DE2937831C2 (en:Method) | ||
| DE875356C (de) | Verfahren zur Herstellung von aliphatischen und cycloaliphatischen Hydroperoxyden | |
| EP0010236B1 (de) | Verfahren zur Herstellung von 2,3-Dimethyl-2,3-butandiol | |
| DE3744212A1 (de) | Verfahren zur herstellung von 2-methylbutanal | |
| EP0075238B1 (de) | Verfahren zur Herstellung von 3-Alkyl-3-acyloxy-4-hydroxy-1-butenen | |
| DE2917779C2 (de) | Verfahren zur Herstellung von 2,3-Dimethylbuten-2 | |
| EP0033110B1 (de) | Verfahren zur Herstellung von Epoxyalkanen | |
| EP0979220B1 (de) | Einstufiges verfahren zur herstellung von alpha-hydroxyethern durch oxidation c=c-ungesättigter verbindungen mit hydroperoxiden | |
| DE3811039A1 (de) | Verfahren zur gewinnung von 2-methylalkanalen aus gemischen isomerer aldehyde | |
| DE4301554C1 (de) | Verfahren zur Herstellung von Diethoxymethan | |
| DE3811059A1 (de) | Verfahren zur trennung von butanol und butoxyacetaldehyd | |
| DE1950434C3 (de) | Verfahren zur kontinuierlichen Herstellung von 1-Methyl-3-phenylindanen | |
| DE1064941B (de) | Verfahren zur Herstellung von Gemischen aus gesaettigten aliphatischen oder cycloaliphatischen Monocarbonsaeurealkylestern | |
| DE2448231C2 (de) | Verfahren zur Herstellung von Alkylnaphthalinen | |
| DE1068255B (de) | Verfahren zur Herstellung von cyclischen Carbonsäuren und bzw. oder deren Estern aus Cyclododecatrienen-(1,5,9) | |
| DE898893C (de) | Verfahren zur Abtrennung aliphatischer Alkohole aus Produkten der katalytischen Kohlenoxydhydrierung | |
| EP0564979B1 (de) | Verfahren zur Herstellung von Dixylylpropan | |
| DE1643617B2 (en:Method) | ||
| DE1919495A1 (de) | Verfahren zur Herstellung von Trioxan | |
| DE1668966C (de) | Verfahren zur gleichzeitigen Herstellung von 2,6-Dimethyl-phenol und 4-tert-Butylphenol | |
| DE1099520B (de) | Verfahren zur Herstellung von Monoglyceriden von Fettsaeuren mit 8 bis 22 Kohlenstoffatomen | |
| EP0032989A1 (de) | Verfahren zur Herstellung von alpha-Epoxiden mit 11 bis 24 Kohlenstoffatomen | |
| DE2202249A1 (de) | Isolierung von alpha-Cedren aus Zedernholzoelkohlenwasserstoffen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8365 | Fully valid after opposition proceedings | ||
| 8339 | Ceased/non-payment of the annual fee |