DE3229084A1 - Verfahren zur herstellung von vicinalen diolen und deren formiaten - Google Patents
Verfahren zur herstellung von vicinalen diolen und deren formiatenInfo
- Publication number
- DE3229084A1 DE3229084A1 DE19823229084 DE3229084A DE3229084A1 DE 3229084 A1 DE3229084 A1 DE 3229084A1 DE 19823229084 DE19823229084 DE 19823229084 DE 3229084 A DE3229084 A DE 3229084A DE 3229084 A1 DE3229084 A1 DE 3229084A1
- Authority
- DE
- Germany
- Prior art keywords
- radicals
- formic acid
- formula
- olefins
- carbon atoms
- 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.)
- Granted
Links
- 150000002009 diols Chemical group 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 9
- 150000004675 formic acid derivatives Chemical group 0.000 title abstract description 13
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 35
- 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 abstract description 17
- 150000001336 alkenes Chemical class 0.000 claims abstract description 17
- 235000019253 formic acid Nutrition 0.000 claims abstract description 17
- 230000003197 catalytic effect Effects 0.000 claims abstract description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 claims 1
- 230000006324 decarbonylation Effects 0.000 abstract description 4
- 238000006606 decarbonylation reaction Methods 0.000 abstract description 4
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- -1 alkyl radical Chemical group 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- DCYPPXGEIQTVPI-UHFFFAOYSA-N cycloheptane-1,2-diol Chemical compound OC1CCCCCC1O DCYPPXGEIQTVPI-UHFFFAOYSA-N 0.000 description 2
- VCVOSERVUCJNPR-UHFFFAOYSA-N cyclopentane-1,2-diol Chemical compound OC1CCCC1O VCVOSERVUCJNPR-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PKXHXOTZMFCXSH-UHFFFAOYSA-N 3,3-dimethylbut-1-ene Chemical compound CC(C)(C)C=C PKXHXOTZMFCXSH-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N Benzylformate Chemical class O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-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
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical class CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- HUSOFJYAGDTKSK-UHFFFAOYSA-N cyclooctane-1,2-diol Chemical compound OC1CCCCCCC1O HUSOFJYAGDTKSK-UHFFFAOYSA-N 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
-
- 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
- C07C29/04—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 by hydration of carbon-to-carbon double bonds
-
- 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
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
- C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823229084 DE3229084A1 (de) | 1982-08-04 | 1982-08-04 | Verfahren zur herstellung von vicinalen diolen und deren formiaten |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823229084 DE3229084A1 (de) | 1982-08-04 | 1982-08-04 | Verfahren zur herstellung von vicinalen diolen und deren formiaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3229084A1 true DE3229084A1 (de) | 1984-02-09 |
| DE3229084C2 DE3229084C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-06-20 |
Family
ID=6170091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823229084 Granted DE3229084A1 (de) | 1982-08-04 | 1982-08-04 | Verfahren zur herstellung von vicinalen diolen und deren formiaten |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3229084A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999016733A1 (de) * | 1997-09-29 | 1999-04-08 | Basf Aktiengesellschaft | Verfahren zur herstellung von vicinalen diolen oder polyolen |
| US7385092B2 (en) | 2004-12-15 | 2008-06-10 | Degussa Ag | Process for preparing alkanediols and alkanetriols having a vicinal diol group |
| WO2019029808A1 (en) * | 2017-08-09 | 2019-02-14 | Symrise Ag | 1,2-ALKANEDIOLS AND PROCESSES FOR PRODUCING THE SAME |
| EP3878832A1 (de) | 2020-03-11 | 2021-09-15 | Evonik Operations GmbH | Verfahren zur desodorisierung von 1,2-alkandiolen durch destillation |
| EP3878833A1 (de) | 2020-03-11 | 2021-09-15 | Evonik Operations GmbH | Verfahren zur desodorisierung von 1,2-alkandiolen durch destillation |
| EP3878834A1 (de) | 2020-03-11 | 2021-09-15 | Evonik Operations GmbH | Verfahren zur desodorisierung von 1,2-alkandiolen durch destillation |
| DE202017007679U1 (de) | 2017-08-09 | 2024-03-15 | Symrise Ag | 1,2-Alkandiole |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2844637B1 (de) * | 1978-10-13 | 1980-01-03 | Ruhrchemie Ag | Verfahren zur Herstellung von 2,3-Dimethyl-2,3-butandiol |
| DE2937831C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1979-09-19 | 1989-04-27 | Henkel Kgaa, 4000 Duesseldorf, De |
-
1982
- 1982-08-04 DE DE19823229084 patent/DE3229084A1/de active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2844637B1 (de) * | 1978-10-13 | 1980-01-03 | Ruhrchemie Ag | Verfahren zur Herstellung von 2,3-Dimethyl-2,3-butandiol |
| DE2937831C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1979-09-19 | 1989-04-27 | Henkel Kgaa, 4000 Duesseldorf, De |
Non-Patent Citations (1)
| Title |
|---|
| J. Org. Chem. 35 (1970) 1694 * |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999016733A1 (de) * | 1997-09-29 | 1999-04-08 | Basf Aktiengesellschaft | Verfahren zur herstellung von vicinalen diolen oder polyolen |
| US6281394B1 (en) * | 1997-09-29 | 2001-08-28 | Basf Aktiengesellschaft | Method for producing vicinal diols or polyols |
| US7385092B2 (en) | 2004-12-15 | 2008-06-10 | Degussa Ag | Process for preparing alkanediols and alkanetriols having a vicinal diol group |
| WO2019029808A1 (en) * | 2017-08-09 | 2019-02-14 | Symrise Ag | 1,2-ALKANEDIOLS AND PROCESSES FOR PRODUCING THE SAME |
| CN109384650A (zh) * | 2017-08-09 | 2019-02-26 | 西姆莱斯股份公司 | 1,2-链烷二醇及其制备方法 |
| JP2019055931A (ja) * | 2017-08-09 | 2019-04-11 | シムライズ アーゲー | １，２−アルカンジオールおよびそれらの製造方法 |
| EP4331684A2 (en) | 2017-08-09 | 2024-03-06 | Symrise AG | 1,2-alkanediols |
| DE202017007679U1 (de) | 2017-08-09 | 2024-03-15 | Symrise Ag | 1,2-Alkandiole |
| EP4331684A3 (en) * | 2017-08-09 | 2024-05-29 | Symrise AG | 1,2-alkanediols |
| EP3878832A1 (de) | 2020-03-11 | 2021-09-15 | Evonik Operations GmbH | Verfahren zur desodorisierung von 1,2-alkandiolen durch destillation |
| EP3878833A1 (de) | 2020-03-11 | 2021-09-15 | Evonik Operations GmbH | Verfahren zur desodorisierung von 1,2-alkandiolen durch destillation |
| EP3878834A1 (de) | 2020-03-11 | 2021-09-15 | Evonik Operations GmbH | Verfahren zur desodorisierung von 1,2-alkandiolen durch destillation |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3229084C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-06-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: HUELS TROISDORF AG, 5210 TROISDORF, DE |
|
| 8127 | New person/name/address of the applicant |
Owner name: HUELS AG, 4370 MARL, DE |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |