CA1055013A - Process for producing steroidal compounds - Google Patents
Process for producing steroidal compoundsInfo
- Publication number
- CA1055013A CA1055013A CA232,932A CA232932A CA1055013A CA 1055013 A CA1055013 A CA 1055013A CA 232932 A CA232932 A CA 232932A CA 1055013 A CA1055013 A CA 1055013A
- Authority
- CA
- Canada
- Prior art keywords
- steroidal
- hydrocarbon
- dien
- methyl
- 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
Links
- 230000003637 steroidlike Effects 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title claims abstract description 35
- 150000001875 compounds Chemical class 0.000 title claims abstract description 23
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 52
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 52
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 49
- 238000006243 chemical reaction Methods 0.000 claims description 48
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 24
- 238000000197 pyrolysis Methods 0.000 claims description 17
- 150000003431 steroids Chemical class 0.000 claims description 17
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 16
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 claims description 13
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical group OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 claims description 13
- 239000003350 kerosene Substances 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003921 oil Substances 0.000 claims description 8
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- 239000002480 mineral oil Substances 0.000 claims description 6
- 235000010446 mineral oil Nutrition 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- LUJVUUWNAPIQQI-QAGGRKNESA-N androsta-1,4-diene-3,17-dione Chemical group O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 LUJVUUWNAPIQQI-QAGGRKNESA-N 0.000 claims description 5
- 239000011551 heat transfer agent Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 4
- 239000001273 butane Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 4
- 239000001294 propane Substances 0.000 claims description 4
- 229940058172 ethylbenzene Drugs 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- WTRRIQCGCGCMQA-CBZIJGRNSA-N 3-Hydroxyestra-1,3,5(10),6-tetraen-17-one Chemical group OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3C=CC2=C1 WTRRIQCGCGCMQA-CBZIJGRNSA-N 0.000 claims 1
- DKVSUQWCZQBWCP-QAGGRKNESA-N androsta-1,4,6-triene-3,17-dione Chemical group O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3C=CC2=C1 DKVSUQWCZQBWCP-QAGGRKNESA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 19
- 229960003399 estrone Drugs 0.000 description 12
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000012295 chemical reaction liquid Substances 0.000 description 8
- 239000000571 coke Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 230000035611 feeding Effects 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- WGFQJPRCLLMHRT-XZIMXZIZSA-N (8r,9s,10r,13s,14s)-17-hydroxy-10,13-dimethyl-8,9,11,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)O)[C@@H]4[C@@H]3C=CC2=C1 WGFQJPRCLLMHRT-XZIMXZIZSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- CHNXZKVNWQUJIB-CEGNMAFCSA-N ethisterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 CHNXZKVNWQUJIB-CEGNMAFCSA-N 0.000 description 2
- 229960000445 ethisterone Drugs 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012495 reaction gas Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229940127234 oral contraceptive Drugs 0.000 description 1
- 239000003539 oral contraceptive agent Substances 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0059—Estrane derivatives substituted in position 17 by a keto group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49096350A JPS5126865A (en) | 1974-08-22 | 1974-08-22 | 33 hidorokishi 199 noru 1*3*5 * 10 * torienkeisuteroidono seizoho |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1055013A true CA1055013A (en) | 1979-05-22 |
Family
ID=14162541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA232,932A Expired CA1055013A (en) | 1974-08-22 | 1975-08-06 | Process for producing steroidal compounds |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3994938A (enExample) |
| JP (1) | JPS5126865A (enExample) |
| CA (1) | CA1055013A (enExample) |
| CH (1) | CH620224A5 (enExample) |
| DE (1) | DE2537254C3 (enExample) |
| FR (1) | FR2282433A1 (enExample) |
| GB (1) | GB1498746A (enExample) |
| MX (1) | MX3008E (enExample) |
| NL (1) | NL167170C (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3931820A1 (de) * | 1989-09-20 | 1991-03-28 | Schering Ag | Verfahren zur herstellung von 3-hydroxyl-1,3,5(10)-estratrien-17-on |
| RU2170740C1 (ru) * | 2000-02-22 | 2001-07-20 | Закрытое акционерное общество "ПЕНТКРОФТ ФАРМА" | Способ получения d-эстра-1,3,5(10)-триен-3-ол-17-она (эстрона) |
-
1974
- 1974-08-22 JP JP49096350A patent/JPS5126865A/ja active Granted
-
1975
- 1975-08-06 CA CA232,932A patent/CA1055013A/en not_active Expired
- 1975-08-08 US US05/602,810 patent/US3994938A/en not_active Expired - Lifetime
- 1975-08-21 GB GB34752/75A patent/GB1498746A/en not_active Expired
- 1975-08-21 NL NL7509927.A patent/NL167170C/xx not_active IP Right Cessation
- 1975-08-21 FR FR7525900A patent/FR2282433A1/fr active Granted
- 1975-08-21 CH CH1086775A patent/CH620224A5/de not_active IP Right Cessation
- 1975-08-21 DE DE2537254A patent/DE2537254C3/de not_active Expired
- 1975-08-22 MX MX002038U patent/MX3008E/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2537254A1 (de) | 1976-03-04 |
| NL167170B (nl) | 1981-06-16 |
| NL7509927A (nl) | 1976-02-24 |
| NL167170C (nl) | 1981-11-16 |
| CH620224A5 (enExample) | 1980-11-14 |
| MX3008E (es) | 1980-01-28 |
| JPS5331155B2 (enExample) | 1978-08-31 |
| US3994938A (en) | 1976-11-30 |
| FR2282433B1 (enExample) | 1979-05-18 |
| FR2282433A1 (fr) | 1976-03-19 |
| DE2537254B2 (de) | 1978-06-15 |
| JPS5126865A (en) | 1976-03-05 |
| GB1498746A (en) | 1978-01-25 |
| DE2537254C3 (de) | 1979-02-08 |
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